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Welcome to a truly special Queenstown retreat, 108 Bullet Run Drive. Sweeping lake views, wide open farmland, and peaceful Eastern Shore living come together in this 1.234 acre property. Tucked away with views of picturesque cornfields, this beautifully maintained 3-bedroom, 2 bath rancher offers an unmatched sense of privacy, tranquility and space. Thoughtfully designed for effortless living, this home offers something for everyone. Whether you are a first time home-buyer starting a family, or a retiree looking to get rid of that colonial and HOA, this is the type of property people are seeking. As you enter, you will be blown away by the gorgeous vaulted ceilings, floor to ceiling stone fireplace and open floor plan. Complete with LVP flooring, stainless steel appliances, stunning white doweled drawer cabinetry with self close hinges, and a large granite kitchen island- this home not only feels cozy but has all the amenities to provide great entertaining as well. The primary suite flows perfectly off the rights side of the house, with the on suite bath, walk in closet, and separate laundry room; while the other two bedrooms and second bath were intentionally built on the left side of the house. The side loading two car garage and oversized driveway offers plenty of parking while the location is only minutes away from route 50, and only a short drive to Annapolis or Ocean City! Enjoy a fresh cup of coffee from your gorgeous front porch or soak in the serenity of the lake views under the pergola on your composite deck. Even the four legged friends give this one their stamp of approval. With a super convenient, but private location this home is everything you've been waiting for and more!

108 Bullet Run Dr, Queenstown

Listing courtesy of Keller Williams Realty. Contact:

$425,000

Welcome to this beautifully maintained `three-bedroom, two-bathroom home, built in 2021 and offering a like-new feeling. The thoughtfully designed interior features modern finishes throughout, including granite countertops, stainless steel appliances, tankless water heater, and the exterior features hardi-plank siding. Quality construction inside and out. This home is move-in ready and offers a perfect blend of modern comfort and small town living.

Welcome to this beautifully maintained `three-bedroom, two-bathroom home, built in 2021 and offering a like-new feeling. The thoughtfully designed interior features modern finishes throughout, including granite countertops, stainless steel appliances, tankless water heater, and the exterior features hardi-plank siding. Quality construction inside and out. This home is move-in ready and offers a perfect blend of modern comfort and small town living.

414 Church St, Sudlersville

Listing courtesy of Coldwell Banker Realty. Contact:

$450,000

Mixed-use commercial property offering exceptional exposure in a sought-after location. The first floor commercial space features about 1800+ sq' separated between a large retail space, office/kitchen , and storage space. The second floor includes a 2-bedroom, 1-bath apartment—ideal for owner occupancy or rental income. Seller financing may be available for buyers with 20% down, 5% interest, amortized at 15 years with a 5 year balloon. The building offers flexible layout potential and is truly ready for your vision. Downstairs can easily be divided into three sections to rent out separately. Situated on nearly a half-acre lot, the property boasts a generous parking area with 12+ spaces and room for future expansion. A rare opportunity for entrepreneurs, investors, or owner-operators looking to establish or grow their business in the heart of Centreville. Take advantage of the seller financing opportunity and 5% rate!

Mixed-use commercial property offering exceptional exposure in a sought-after location. The first floor commercial space features about 1800+ sq' separated between a large retail space, office/kitchen , and storage space. The second floor includes a 2-bedroom, 1-bath apartment—ideal for owner occupancy or rental income. Seller financing may be available for buyers with 20% down, 5% interest, amortized at 15 years with a 5 year balloon. The building offers flexible layout potential and is truly ready for your vision. Downstairs can easily be divided into three sections to rent out separately. Situated on nearly a half-acre lot, the property boasts a generous parking area with 12+ spaces and room for future expansion. A rare opportunity for entrepreneurs, investors, or owner-operators looking to establish or grow their business in the heart of Centreville. Take advantage of the seller financing opportunity and 5% rate!

305 E Water St, Centreville

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

$375,000

Country living with NO HOA fees. The home boasts excellent curb appeal and sits on a one acre parcel. The public record reflects the main floor square footage of 1440 with the home originally built with three bedrooms. The homeowner had an addition built, increasing the total square footage to approximately 1540 square feet with a modification of two bedrooms. The listing reflects the home presently having two bedrooms; however, the home could easily be converted back to three bedrooms if needed.

2 Beds ⋅ 2 Baths

Country living with NO HOA fees. The home boasts excellent curb appeal and sits on a one acre parcel. The public record reflects the main floor square footage of 1440 with the home originally built with three bedrooms. The homeowner had an addition built, increasing the total square footage to approximately 1540 square feet with a modification of two bedrooms. The listing reflects the home presently having two bedrooms; however, the home could easily be converted back to three bedrooms if needed.

224 Ewingtown Rd, Church Hill

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$669,900

ABSOLUTELY A MUST-SEE!...This stunning custom built home shows like a model and truly checks all the boxes! Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. It offers exceptional space, and the feel of a brand new home, just 2 years young and located in a newly developed community. Spanning over 2,400+ square feet on a 1-acre lot, this impressive home features 4 bedrooms and 3 full bathrooms with a crafted open layout. Step through the beautiful foyer with its impressive 8 ft wood entry door and into the designer gourmet kitchen, featuring a large island, sleek quartz countertops, stainless steel appliances, propane cooktop, wall oven, and gorgeous lighting. The kitchen also offers under cabinet lighting and a custom pantry with a cubby area, perfect for keeping shoes, coats, jackets, and hats organized. The kitchen and dining area seamlessly adjoin the inviting living room, featuring a cozy fireplace and elegant 8-foot French doors that flood the space with natural light while creating a seamless connection to the outdoors. It’s the perfect setting for both everyday living and entertaining. The first floor also offers a bedroom with a full bathroom, currently being used as an office, providing flexibility for work from home needs. Upstairs you'll be impressed by the abundance of space. The spacious primary suite features a beautiful en-suite bathroom with a double vanity and tiled walk-in shower. Two additional bedrooms and a full bathroom provide plenty of room for your family/or guests. And there's more!!! A large family/game room provides the perfect bonus space for movie nights, game days, hobbies, or simply spreading out and relaxing. Outside, enjoy both a welcoming front porch and spacious back porch, along with a paver patio area perfect for a fire pit, outdoor dining or just relaxing. The lush landscaping adds to the home's curb appeal, while a row of cypress trees lines the property and will provide beautiful privacy as they mature. Additional highlights include high ceilings, upscale lighting, LVP flooring and ceramic tile flooring. The home features an abundance of storage area throughout for organization. For ultimate convenience, the second floor laundry room comes fully equipped with a handy folding table and a hanging clothes rack. Rounding out this impressive property is an attached side entry garage that enhances the home's exterior profile. This home has it all, space, style, upgrades, privacy, and an incredible layout. Just a few miles from picturesque historic Chestertown and Centreville, easy commute to Easton, Annapolis and MD/DE beaches! Come enjoy the Eastern Shore -fishing, crabbing piers, playgrounds, bike/walking trails, parks and so much more! Don't delay!! Come see this beauty before someone else gets the opportunity to call it home. You will want this one to be yours!

ABSOLUTELY A MUST-SEE!...This stunning custom built home shows like a model and truly checks all the boxes! Showcasing outstanding craftsmanship, thoughtful design, and high-end finishes throughout, every detail has been carefully curated to create a home that is both elegant and inviting. It offers exceptional space, and the feel of a brand new home, just 2 years young and located in a newly developed community. Spanning over 2,400+ square feet on a 1-acre lot, this impressive home features 4 bedrooms and 3 full bathrooms with a crafted open layout. Step through the beautiful foyer with its impressive 8 ft wood entry door and into the designer gourmet kitchen, featuring a large island, sleek quartz countertops, stainless steel appliances, propane cooktop, wall oven, and gorgeous lighting. The kitchen also offers under cabinet lighting and a custom pantry with a cubby area, perfect for keeping shoes, coats, jackets, and hats organized. The kitchen and dining area seamlessly adjoin the inviting living room, featuring a cozy fireplace and elegant 8-foot French doors that flood the space with natural light while creating a seamless connection to the outdoors. It’s the perfect setting for both everyday living and entertaining. The first floor also offers a bedroom with a full bathroom, currently being used as an office, providing flexibility for work from home needs. Upstairs you'll be impressed by the abundance of space. The spacious primary suite features a beautiful en-suite bathroom with a double vanity and tiled walk-in shower. Two additional bedrooms and a full bathroom provide plenty of room for your family/or guests. And there's more!!! A large family/game room provides the perfect bonus space for movie nights, game days, hobbies, or simply spreading out and relaxing. Outside, enjoy both a welcoming front porch and spacious back porch, along with a paver patio area perfect for a fire pit, outdoor dining or just relaxing. The lush landscaping adds to the home's curb appeal, while a row of cypress trees lines the property and will provide beautiful privacy as they mature. Additional highlights include high ceilings, upscale lighting, LVP flooring and ceramic tile flooring. The home features an abundance of storage area throughout for organization. For ultimate convenience, the second floor laundry room comes fully equipped with a handy folding table and a hanging clothes rack. Rounding out this impressive property is an attached side entry garage that enhances the home's exterior profile. This home has it all, space, style, upgrades, privacy, and an incredible layout. Just a few miles from picturesque historic Chestertown and Centreville, easy commute to Easton, Annapolis and MD/DE beaches! Come enjoy the Eastern Shore -fishing, crabbing piers, playgrounds, bike/walking trails, parks and so much more! Don't delay!! Come see this beauty before someone else gets the opportunity to call it home. You will want this one to be yours!

458 Eagle Manor Dr, Church Hill

Listing courtesy of Clark & Co Realty, LLC. Contact:

$549,000

Favorable rates. Flawless timing. Finalize your move before the holidays. This move-in-ready home offers the perfect opportunity to lock in a lower rate and settle in before the holidays! Why wait to build? This beautifully finished 2026 home is complete, move-in ready, and situated on a spacious one-acre lot in Church Hill’s desirable Condor Manor community. Offering 2,016 square feet, 4 bedrooms, 2.5 baths, and a two-car garage, this home combines modern finishes, energy-efficient construction, and the outdoor space today’s buyers are looking for. Step inside to a bright, open first floor featuring durable luxury vinyl plank flooring and plenty of room for everyday living and entertaining. The kitchen is the heart of the home with granite countertops, stainless steel appliances, and 42” American Woodmark cabinetry. Two generous living areas and a dining space provide flexibility for entertaining, relaxing, a home office, or play space, with peaceful views of the backyard. Upstairs, upgraded wall-to-wall carpeting creates a comfortable retreat. The spacious primary suite features a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide plenty of room for family, guests, hobbies, or office space. Built with efficiency and convenience in mind, the home features enhanced insulation, Low-E windows and doors, energy-efficient mechanical systems, and a conditioned crawl space. The two-car garage is pre-wired for electric vehicle charging, and the large driveway provides ample additional parking. Enjoy your morning coffee on the covered front porch or entertain on the 12’ x 16’ rear deck overlooking the expansive backyard. With a full acre, there’s room for pets, gardening, recreation, outdoor entertaining, and future projects—or simply enjoy having more privacy and breathing room. Located just outside the town of Church Hill with convenient access to Routes 213 and 301, Condor Manor offers a peaceful Eastern Shore setting while keeping commuting routes within easy reach. Newly built. One full acre. Four bedrooms. Move-in ready. And now offered at a great new price. Schedule your private showing and see the value this home has to offer. This community consists of 26 homes/lots . NOTE: At the time of listing, the calculated taxes reflect the assessment on the property and do not yet include the newly built home/improvements. Buyers should verify future tax assessments.

Favorable rates. Flawless timing. Finalize your move before the holidays. This move-in-ready home offers the perfect opportunity to lock in a lower rate and settle in before the holidays! Why wait to build? This beautifully finished 2026 home is complete, move-in ready, and situated on a spacious one-acre lot in Church Hill’s desirable Condor Manor community. Offering 2,016 square feet, 4 bedrooms, 2.5 baths, and a two-car garage, this home combines modern finishes, energy-efficient construction, and the outdoor space today’s buyers are looking for. Step inside to a bright, open first floor featuring durable luxury vinyl plank flooring and plenty of room for everyday living and entertaining. The kitchen is the heart of the home with granite countertops, stainless steel appliances, and 42” American Woodmark cabinetry. Two generous living areas and a dining space provide flexibility for entertaining, relaxing, a home office, or play space, with peaceful views of the backyard. Upstairs, upgraded wall-to-wall carpeting creates a comfortable retreat. The spacious primary suite features a walk-in closet and private bath, while three additional bedrooms and a full hall bath provide plenty of room for family, guests, hobbies, or office space. Built with efficiency and convenience in mind, the home features enhanced insulation, Low-E windows and doors, energy-efficient mechanical systems, and a conditioned crawl space. The two-car garage is pre-wired for electric vehicle charging, and the large driveway provides ample additional parking. Enjoy your morning coffee on the covered front porch or entertain on the 12’ x 16’ rear deck overlooking the expansive backyard. With a full acre, there’s room for pets, gardening, recreation, outdoor entertaining, and future projects—or simply enjoy having more privacy and breathing room. Located just outside the town of Church Hill with convenient access to Routes 213 and 301, Condor Manor offers a peaceful Eastern Shore setting while keeping commuting routes within easy reach. Newly built. One full acre. Four bedrooms. Move-in ready. And now offered at a great new price. Schedule your private showing and see the value this home has to offer. This community consists of 26 homes/lots . NOTE: At the time of listing, the calculated taxes reflect the assessment on the property and do not yet include the newly built home/improvements. Buyers should verify future tax assessments.

334 Eagle Manor Dr, Church Hill

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$400,000

Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. NOTE: Manufactured home with skirting-- without a foundation- so it may impact financing approvals. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend retreat, full-time residence, recreational getaway, or potential future waterfront homesite, this property offers plenty of possibilities. Convenient access to US Route 301 provides easy travel to Delaware and surrounding Eastern Shore communities. Enjoy 7.19± acres of Chester River waterfront with hunting, fishing, and boating opportunities on Maryland’s Eastern Shore.

Secluded Riverfront Get-away. Rare opportunity to own 7.19± wooded acres along the Chester River in Queen Anne’s County. Tucked away at the end of a quiet cul-de-sac, the property features an approximately 1,100-square-foot manufactured home (1987) with a newer roof and windows, rear deck, private well, and BAT septic system approved for up to four bedrooms. NOTE: Manufactured home with skirting-- without a foundation- so it may impact financing approvals. Excellent lot opportunity to add a garage or pole barn. A natural beach area with 770' of riverfront (provides direct river access for fishing, kayaking, boating. Mature woods offer privacy, wildlife habitat, and hunting opportunities rarely found on a traditional waterfront homesite. Whether you're looking for a weekend retreat, full-time residence, recreational getaway, or potential future waterfront homesite, this property offers plenty of possibilities. Convenient access to US Route 301 provides easy travel to Delaware and surrounding Eastern Shore communities. Enjoy 7.19± acres of Chester River waterfront with hunting, fishing, and boating opportunities on Maryland’s Eastern Shore.

405 Rings End Rd, Millington

Listing courtesy of Whitetail Properties Real Estate, LLC. Contact:

$899,000

Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shore’s most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the community’s active social calendar. Ideally located on Maryland’s Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and community—all just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 10th green. Situated on a one-acre lot, the home offers over 3,000 square feet, 4–5 bedrooms, a three-car garage, and a comfortable, flexible floor plan designed for everyday living and entertaining. A dramatic two-story foyer leads to bright living spaces accented by tray and vaulted ceilings. The spacious kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, and opens to the family room with bamboo flooring, gas fireplace, custom built-ins, and access to the large deck. A separate dining room and main-level bedroom add versatility. The spacious primary suite offers a large walk-in closet and private bath with soaking tub, dual vanities, and walk-in shower. Enjoy beautiful golf course views from the deck or screened gazebo—perfect for relaxing, entertaining, or an Eastern Shore crab feast.

5 Beds ⋅ 3 Baths

Come experience the relaxed, resort-style lifestyle of Prospect Bay, one of the Eastern Shore’s most desirable golf course communities. Spend your days enjoying the 18-hole championship golf course, relaxing by the community pool, playing tennis or pickleball, or heading out on the water. Prospect Bay offers a community boat ramp and marina with access to navigable waters leading to Eastern Bay, putting St. Michaels, Kent Narrows, Annapolis, and other Chesapeake Bay destinations within reach by boat. Meet friends for dinner or drinks at the clubhouse restaurant, visit the pro shop, or take part in the community’s active social calendar. Ideally located on Maryland’s Eastern Shore, Prospect Bay offers a wonderful combination of golf, boating, recreation, and community—all just minutes from the Chesapeake Bay Bridge, approximately 25 minutes from Annapolis and one hour from BWI Airport. Set within this exceptional community, this beautiful custom home enjoys a prime setting overlooking the 10th green. Situated on a one-acre lot, the home offers over 3,000 square feet, 4–5 bedrooms, a three-car garage, and a comfortable, flexible floor plan designed for everyday living and entertaining. A dramatic two-story foyer leads to bright living spaces accented by tray and vaulted ceilings. The spacious kitchen features abundant cabinetry, a center island, pantry, and sunny morning room, and opens to the family room with bamboo flooring, gas fireplace, custom built-ins, and access to the large deck. A separate dining room and main-level bedroom add versatility. The spacious primary suite offers a large walk-in closet and private bath with soaking tub, dual vanities, and walk-in shower. Enjoy beautiful golf course views from the deck or screened gazebo—perfect for relaxing, entertaining, or an Eastern Shore crab feast.

14 Fairway Is, Grasonville

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

$279,999

Back on the market! Price Reduction! Amazing remodel! Home is a 3-bedroom, 1 bath home in Millington, MD with easy access to Rte. 301 for any daily commute! There is an additional room that could be used as a 4th bedroom or an office. Home sits on a half-acre of property with a huge side yard for any new buildings or storage needs. Home has well and septic so no quarterly water and sewer bills! Updates include a completely new kitchen with stainless steel appliances and quartz countertops, new wood style LPV flooring, new HVAC, metal roof, front porch, back deck, new ceiling fans, recessed lights, new water treatment system, newer septic, newer well pump and newer bladder tank. This place shines beautifully! Build equity! Pay a mortgage for less than you can pay rent! Make your appointment today and see all that this home has to offer. Call Lori for your private tour!

3 Beds ⋅ 1 Baths

Back on the market! Price Reduction! Amazing remodel! Home is a 3-bedroom, 1 bath home in Millington, MD with easy access to Rte. 301 for any daily commute! There is an additional room that could be used as a 4th bedroom or an office. Home sits on a half-acre of property with a huge side yard for any new buildings or storage needs. Home has well and septic so no quarterly water and sewer bills! Updates include a completely new kitchen with stainless steel appliances and quartz countertops, new wood style LPV flooring, new HVAC, metal roof, front porch, back deck, new ceiling fans, recessed lights, new water treatment system, newer septic, newer well pump and newer bladder tank. This place shines beautifully! Build equity! Pay a mortgage for less than you can pay rent! Make your appointment today and see all that this home has to offer. Call Lori for your private tour!

210 Groff Rd, Millington

Listing courtesy of RE/MAX Chesapeake. Contact:

$535,000

SPACE, PRIVACY, NO HOA & A LARGE DETACHED POLE BARN! Welcome to 639 Poplar School Road, Centreville, where peaceful Eastern Shore living meets comfort, convenience, and room to spread out! Situated on a beautifully landscaped 1-acre lot, this well-maintained 3-bedroom, 2-bath home offers the space and flexibility today's buyers are looking for, all within an easy drive of downtown Centreville and the Chesapeake Bay Bridge. Inside, you'll find a warm and inviting home featuring fresh professional paint, updated lighting and ceiling fans, and a thoughtfully designed floor plan. The kitchen offers granite countertops and custom cabinetry, while the bathrooms also feature granite countertops. Upstairs, a finished bonus room provides flexible space for a home office, den, or hobby room, with additional unfinished space offering potential for future expansion. Major updates provide added peace of mind, including replacement windows (2018), a newer heat pump (approx. 3 years old), a newer water heater (approx. 1 year old), and a high-end water treatment and softener system (2024). Four new storm doors and other thoughtful improvements add to the home's appeal. Outdoor living is equally inviting! Enjoy your morning coffee on the screened-in porch, entertain on the beautiful paver patio, or relax in the partially fenced backyard. The 29' x 28' Amish-built detached pole barn, complete with electricity and plumbing rough-ins, offers incredible versatility for a workshop, storage, hobbies, or recreational equipment. An attached two-car garage with a finished epoxy floor provides even more storage and convenience. No HOA, a full acre of land, and room for your hobbies and outdoor lifestyle! Conveniently located near historic downtown Centreville, local shops, restaurants, parks, and the Centreville Wharf, with easy access to Route 50 and approximately 20 minutes to the Chesapeake Bay Bridge. If you've been searching for a well-maintained home with acreage, a substantial outbuilding, and the freedom to enjoy Eastern Shore living, 639 Poplar School Road deserves a closer look!

SPACE, PRIVACY, NO HOA & A LARGE DETACHED POLE BARN! Welcome to 639 Poplar School Road, Centreville, where peaceful Eastern Shore living meets comfort, convenience, and room to spread out! Situated on a beautifully landscaped 1-acre lot, this well-maintained 3-bedroom, 2-bath home offers the space and flexibility today's buyers are looking for, all within an easy drive of downtown Centreville and the Chesapeake Bay Bridge. Inside, you'll find a warm and inviting home featuring fresh professional paint, updated lighting and ceiling fans, and a thoughtfully designed floor plan. The kitchen offers granite countertops and custom cabinetry, while the bathrooms also feature granite countertops. Upstairs, a finished bonus room provides flexible space for a home office, den, or hobby room, with additional unfinished space offering potential for future expansion. Major updates provide added peace of mind, including replacement windows (2018), a newer heat pump (approx. 3 years old), a newer water heater (approx. 1 year old), and a high-end water treatment and softener system (2024). Four new storm doors and other thoughtful improvements add to the home's appeal. Outdoor living is equally inviting! Enjoy your morning coffee on the screened-in porch, entertain on the beautiful paver patio, or relax in the partially fenced backyard. The 29' x 28' Amish-built detached pole barn, complete with electricity and plumbing rough-ins, offers incredible versatility for a workshop, storage, hobbies, or recreational equipment. An attached two-car garage with a finished epoxy floor provides even more storage and convenience. No HOA, a full acre of land, and room for your hobbies and outdoor lifestyle! Conveniently located near historic downtown Centreville, local shops, restaurants, parks, and the Centreville Wharf, with easy access to Route 50 and approximately 20 minutes to the Chesapeake Bay Bridge. If you've been searching for a well-maintained home with acreage, a substantial outbuilding, and the freedom to enjoy Eastern Shore living, 639 Poplar School Road deserves a closer look!

639 Poplar School Rd, Centreville

Listing courtesy of Compass. Contact:

$359,900

Open House, Sunday, 11/15 from 1-4PM * Owner Says Sell! Newly Reduced Price * Bayside Condo Townhomes in Chester * Kent Island - Located in the Popular Community of Bayside just minutes from the Bay Bridge, Castle Harbor Marina for Boaters and all -Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground, so all rooms have windows and the ground floor is a level walk out. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space. The community of Bayside is a waterside community and conveniently located near Castle Harbor Marina which is a privately owned marina and within walking distance of this townhome. It has public water, public sewer, propane gas for fireplaces and is serviced by Breezeline & Talkie for Internet and Cable. The community amenities include Outdoor Pool + Hot Tub w Lifeguard, Clubhouse with Exercise Room, Upper-Level Party/Meeting Room, Tennis, Volleyball. It has an On-Site Property Manager. The community fees include: grass cutting, snow removal, roof, siding, decks, trash & recycle.

Open House, Sunday, 11/15 from 1-4PM * Owner Says Sell! Newly Reduced Price * Bayside Condo Townhomes in Chester * Kent Island - Located in the Popular Community of Bayside just minutes from the Bay Bridge, Castle Harbor Marina for Boaters and all -Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground, so all rooms have windows and the ground floor is a level walk out. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space. The community of Bayside is a waterside community and conveniently located near Castle Harbor Marina which is a privately owned marina and within walking distance of this townhome. It has public water, public sewer, propane gas for fireplaces and is serviced by Breezeline & Talkie for Internet and Cable. The community amenities include Outdoor Pool + Hot Tub w Lifeguard, Clubhouse with Exercise Room, Upper-Level Party/Meeting Room, Tennis, Volleyball. It has an On-Site Property Manager. The community fees include: grass cutting, snow removal, roof, siding, decks, trash & recycle.

108 Blenny Ln, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

$565,000

Sellers of 624 Davol Rd are offering up to $15,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 20, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits.Welcome to 624 Davol Road, a beautifully updated 4-bedroom, 3.5-bath home offering nearly 2,500 square feet in the sought-after Cloverfields community. Recent 2026 improvements include updated flooring, a renovated kitchen, new lighting and a new roof, creating a fresh, move-in-ready feel throughout. Outside, you’ll appreciate the garage, large parking pad and fenced backyard with plenty of space to relax, entertain or play. Cloverfields offers an incredible Eastern Shore lifestyle with a community pool, private beach, playgrounds and marina with boat slips available for rent when offered. Conveniently located just off the first exit over the Bay Bridge, the home provides easy access to nearby trails, shopping, dining and everything Kent Island has to offer. Coming soon — stay tuned for your opportunity to see this spacious, updated Cloverfields home!

4 Beds ⋅ 4 Baths

Sellers of 624 Davol Rd are offering up to $15,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 20, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits.Welcome to 624 Davol Road, a beautifully updated 4-bedroom, 3.5-bath home offering nearly 2,500 square feet in the sought-after Cloverfields community. Recent 2026 improvements include updated flooring, a renovated kitchen, new lighting and a new roof, creating a fresh, move-in-ready feel throughout. Outside, you’ll appreciate the garage, large parking pad and fenced backyard with plenty of space to relax, entertain or play. Cloverfields offers an incredible Eastern Shore lifestyle with a community pool, private beach, playgrounds and marina with boat slips available for rent when offered. Conveniently located just off the first exit over the Bay Bridge, the home provides easy access to nearby trails, shopping, dining and everything Kent Island has to offer. Coming soon — stay tuned for your opportunity to see this spacious, updated Cloverfields home!

624 Davol Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

$450,000

Great setting in Kent Island 4 bedrooms and three bathrooms, First floor primary bedroom and then possibly a in-law suite. Located In the heart of farmland on Kent Island, with some water views and watch the sunsets on the bay. This property has beach access. Many great features in this home with vaulted ceilings updated kitchen with granite counters, two car garage fenced back yard nice deck off the back yard. 12-to-15-minute commute to Bay Bridge and shopping. idea for commuters, Enjoy the eastern shore living at its best.

Great setting in Kent Island 4 bedrooms and three bathrooms, First floor primary bedroom and then possibly a in-law suite. Located In the heart of farmland on Kent Island, with some water views and watch the sunsets on the bay. This property has beach access. Many great features in this home with vaulted ceilings updated kitchen with granite counters, two car garage fenced back yard nice deck off the back yard. 12-to-15-minute commute to Bay Bridge and shopping. idea for commuters, Enjoy the eastern shore living at its best.

107 Trequassin Dr, Stevensville

Listing courtesy of Coldwell Banker Realty. Contact:

$699,000

Welcome to your own private Eastern Shore retreat! Nestled on approximately 17.6 picturesque acres, this charming property offers the perfect blend of peaceful country living and everyday convenience. The home features comfortable one-level living with spacious gathering areas, a cozy wood stove, and beautiful views of the surrounding countryside. Whether you’re looking for room to garden, hunt, farm, enjoy outdoor recreation, or simply relax and take in the tranquility, this property provides endless possibilities. The expansive acreage offers privacy, open space, and the opportunity to create the lifestyle you’ve been dreaming of while still being just a short drive to shopping, dining, and major commuter routes.

Welcome to your own private Eastern Shore retreat! Nestled on approximately 17.6 picturesque acres, this charming property offers the perfect blend of peaceful country living and everyday convenience. The home features comfortable one-level living with spacious gathering areas, a cozy wood stove, and beautiful views of the surrounding countryside. Whether you’re looking for room to garden, hunt, farm, enjoy outdoor recreation, or simply relax and take in the tranquility, this property provides endless possibilities. The expansive acreage offers privacy, open space, and the opportunity to create the lifestyle you’ve been dreaming of while still being just a short drive to shopping, dining, and major commuter routes.

1520 John Brown Rd, Queenstown

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

$874,000

Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining. Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers an and additional bedroom, and a second family room. Don't miss the full walk in storage area above the garage that is partially finished. More storage is available in the oversized fully finished two car garage with room for a third car or golf cart. Off the dining area is a screened-in porch and paver patio with a fire pit and out door built in grilling area. Backing to the pond, no houses behind you and views of the fountain is what makes this truly an exceptional lot and setting. The community run irrigation system Is an added bonus to this community. You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience.

Welcome to 214 Bayberry at Four Seasons on Kent Island. Step into refined elegance and low-maintenance, luxury main-level living with this stunning Killarney model. This single family home with 10 foot ceilings blends style, comfort, and functionality, in Kent Island's premier 55+ resort-style community. Enjoy the convenience of a thoughtfully designed main level home featuring a spacious primary suite, guest bedroom, and a private home office - perfect for working from home or hosting visitors in a den setting. The Gourmet Kitchen is special, boasting upgraded appliances, expansive quartz counter tops, custom cabinetry, double wall ovens, stainless steel refrigerator with French doors, and a large island ideal for entertaining. Your primary suite includes a spa style bathroom complete with walk-in shower. The upper level of the home offers an and additional bedroom, and a second family room. Don't miss the full walk in storage area above the garage that is partially finished. More storage is available in the oversized fully finished two car garage with room for a third car or golf cart. Off the dining area is a screened-in porch and paver patio with a fire pit and out door built in grilling area. Backing to the pond, no houses behind you and views of the fountain is what makes this truly an exceptional lot and setting. The community run irrigation system Is an added bonus to this community. You will certainly enjoy the 24,000 square foot Clubhouse located directly on the Chester River. Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. This development is an unrivaled, amenity-filled, resort-style experience.

214 Bayberry Dr, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

$650,000

Sellers of 259 Topside are offering up to $18,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 24, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits.Welcome to 259 Topside Drive in Bay Bridge Cove, one of Kent Island’s most sought-after 55+ communities! This beautifully upgraded Oxford model offers the spacious, flexible floor plan buyers love, paired with a premium setting overlooking the community pond and fountain. Step inside to an open and inviting main level designed for both everyday living and entertaining. The gourmet kitchen is a standout, featuring beautiful light gray cabinetry, a custom backsplash that complements it perfectly, an upgraded appliance package, generous workspace and an easy flow into the main living areas. A cozy fireplace anchors the living room, while the expanded double sunroom fills the rear of the home with natural light and creates even more space to relax, entertain or simply enjoy the view. Step outside onto the deck and take in peaceful pond and fountain views—the perfect backdrop for morning coffee, an evening glass of wine or unwinding at the end of the day.The Oxford’s flexible design continues upstairs, where you'll find an additional bedroom and full bath along with a spacious loft and separate den featuring built-in shelving. Whether you need private guest accommodations, a home office, hobby space, reading room or an additional living area, this second level gives you options without sacrificing the convenience of main-level living. Located in the heart of Stevensville on Kent Island, Bay Bridge Cove offers an active, low-maintenance lifestyle with a clubhouse, fitness center, outdoor pool, recreational courts, walking and biking trails, and plenty of opportunities to connect with neighbors—all just minutes from shopping, dining, waterfront recreation and the Chesapeake Bay Bridge. This isn’t just an Oxford—it’s an Oxford with the upgrades, expanded living space and pond setting buyers wait for.

Sellers of 259 Topside are offering up to $18,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 24, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits.Welcome to 259 Topside Drive in Bay Bridge Cove, one of Kent Island’s most sought-after 55+ communities! This beautifully upgraded Oxford model offers the spacious, flexible floor plan buyers love, paired with a premium setting overlooking the community pond and fountain. Step inside to an open and inviting main level designed for both everyday living and entertaining. The gourmet kitchen is a standout, featuring beautiful light gray cabinetry, a custom backsplash that complements it perfectly, an upgraded appliance package, generous workspace and an easy flow into the main living areas. A cozy fireplace anchors the living room, while the expanded double sunroom fills the rear of the home with natural light and creates even more space to relax, entertain or simply enjoy the view. Step outside onto the deck and take in peaceful pond and fountain views—the perfect backdrop for morning coffee, an evening glass of wine or unwinding at the end of the day.The Oxford’s flexible design continues upstairs, where you'll find an additional bedroom and full bath along with a spacious loft and separate den featuring built-in shelving. Whether you need private guest accommodations, a home office, hobby space, reading room or an additional living area, this second level gives you options without sacrificing the convenience of main-level living. Located in the heart of Stevensville on Kent Island, Bay Bridge Cove offers an active, low-maintenance lifestyle with a clubhouse, fitness center, outdoor pool, recreational courts, walking and biking trails, and plenty of opportunities to connect with neighbors—all just minutes from shopping, dining, waterfront recreation and the Chesapeake Bay Bridge. This isn’t just an Oxford—it’s an Oxford with the upgrades, expanded living space and pond setting buyers wait for.

259 Topside Dr Unit 166, Stevensville

Listing courtesy of Samson Properties. Contact:

$759,000

Nestled in the serene enclave of Oyster Cove, this stunning bayfront townhouse offers a harmonious blend of contemporary design and luxurious living. With three spacious bedrooms and three and a half bathrooms, this residence is perfect for those seeking comfort and style. The moment you step inside, you are greeted by an open floor plan that seamlessly connects the living and dining areas, enhanced by beautiful wood floors and abundant natural light. The living space features a cozy fireplace with glass doors, creating an inviting atmosphere for gatherings or quiet evenings at home. The heart of the home is the country-style kitchen, equipped with upgraded countertops and a suite of modern appliances, including a self-cleaning oven, dishwasher, and refrigerator. Enjoy casual meals in the eat-in kitchen or host dinner parties in the elegant dining area. The primary bedroom is a true retreat, boasting bayfront views, a walk-in closet, and a luxurious en-suite bathroom complete with a jetted tub and walk-in shower. Step outside to discover the community's exceptional amenities. Enjoy leisurely afternoons by the saltwater pool, take a stroll along the scenic jog/walk paths, or engage in friendly matches on the tennis and pickleball courts. The gated community ensures peace of mind, while the clubhouse and party room provide perfect venues for social gatherings. For those who love the outdoors, the nearby marina offers water access to the beautiful Eastern Bay, ideal for boating and fishing enthusiasts. Oyster Cove is not just a home; it's a lifestyle. The neighborhood is rich with common grounds, picnic areas, and a dog park, making it perfect for outdoor activities. With easy access to local shopping, dining, and entertainment, everything you need is just a short drive away. This property is not just a place to live; it's a sanctuary where you can unwind and enjoy the beauty of waterfront living. Don't miss the opportunity to make this exquisite townhouse your new home in Oyster Cove, where every day feels like a vacation. Experience the perfect blend of luxury, comfort, and community in this exceptional property.

3 Beds ⋅ 4 Baths

Nestled in the serene enclave of Oyster Cove, this stunning bayfront townhouse offers a harmonious blend of contemporary design and luxurious living. With three spacious bedrooms and three and a half bathrooms, this residence is perfect for those seeking comfort and style. The moment you step inside, you are greeted by an open floor plan that seamlessly connects the living and dining areas, enhanced by beautiful wood floors and abundant natural light. The living space features a cozy fireplace with glass doors, creating an inviting atmosphere for gatherings or quiet evenings at home. The heart of the home is the country-style kitchen, equipped with upgraded countertops and a suite of modern appliances, including a self-cleaning oven, dishwasher, and refrigerator. Enjoy casual meals in the eat-in kitchen or host dinner parties in the elegant dining area. The primary bedroom is a true retreat, boasting bayfront views, a walk-in closet, and a luxurious en-suite bathroom complete with a jetted tub and walk-in shower. Step outside to discover the community's exceptional amenities. Enjoy leisurely afternoons by the saltwater pool, take a stroll along the scenic jog/walk paths, or engage in friendly matches on the tennis and pickleball courts. The gated community ensures peace of mind, while the clubhouse and party room provide perfect venues for social gatherings. For those who love the outdoors, the nearby marina offers water access to the beautiful Eastern Bay, ideal for boating and fishing enthusiasts. Oyster Cove is not just a home; it's a lifestyle. The neighborhood is rich with common grounds, picnic areas, and a dog park, making it perfect for outdoor activities. With easy access to local shopping, dining, and entertainment, everything you need is just a short drive away. This property is not just a place to live; it's a sanctuary where you can unwind and enjoy the beauty of waterfront living. Don't miss the opportunity to make this exquisite townhouse your new home in Oyster Cove, where every day feels like a vacation. Experience the perfect blend of luxury, comfort, and community in this exceptional property.

1107 Oyster Cove Dr, Grasonville

Listing courtesy of Star Realty. Contact:

$829,000

A must see home! NEW LIST PRICE Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home! Some virtual staging. Immediate upon settlement occupancy.

A must see home! NEW LIST PRICE Super floor plan! Wonderful hardwood floors! Custom fixtures and finishes throughout! The best Family/Great room ever with floor to ceiling fireplace with vaulted ceilings plus outside access to stone patio w/hot tub. Wonderful kitchen featuring oak cabinetry, upgraded appliances, crown moldings, tile & granite backsplash & countertops and eat in breakfast area. Formal Dining room, main level fourth bedroom or office with half bath and exterior entrance, perfect for occasional client or guest. Large 17x13 1st level Living Rm with hardwoods & display center. Inside entrance to the four car garage with additional built-in storage & shelving! Upper level primary bedroom suite featuring 2 walk in closets, gorgeous primary bath with double vanity, huge walk in shower, quartz counters and trim, jetted soaking tub and wainscoting & chair rail finishes. Bedroom #2 w/walk in closet & double entry full bath. Bedroom #3 w/walk in closet, ceiling fan and upper deck access. Upper level laundry area with washer, dryer, shelving and deep sink. Exterior features include 1 Acre lot, beautiful pool with adjoining deck, screen porch, patio w/hot tub and garden shed. Front porch with covered sitting area. Oversized driveway w/side parking area perfect for boat or RV storage. Exterior audio & video system currently in use but not included in the sale. Your super opportunity for a wonderful home! Some virtual staging. Immediate upon settlement occupancy.

113 Bentons Pleasure Rd, Chester

Listing courtesy of Cummings & Co. Realtors. Contact:

$285,000

Discover the charm of Thompson Creek Condos. This beautifully maintained 3-bedroom, 2-bathroom unit offers an inviting open floor plan, perfect for both relaxation and entertaining. Enjoy the warmth of an electric fireplace in the cozy living area, while the spacious eat in kitchen is equipped with essential appliances including a dishwasher and stacked washer/dryer. Step outside to your private balcony, where serene pond views create a tranquil retreat. The community boasts exceptional amenities, including a refreshing outdoor pool, a fitness center, and scenic jogging paths, ensuring an active lifestyle right at your doorstep. With sidewalks and street lights enhancing the neighborhood's charm, evening strolls become a delightful routine. Thompson Creek Condos is ideally situated near top-rated schools, lush parks, and essential public services, making it a prime location for convenience and community engagement. The association fee covers maintenance and insurance, allowing you to enjoy a worry-free lifestyle. Experience the best of both worlds-relaxation and recreation-within this vibrant community. Whether you're lounging by the pool or exploring the nearby river, this property offers a lifestyle that is both enriching and fulfilling. Don't miss your chance to call this stunning condo home!

Discover the charm of Thompson Creek Condos. This beautifully maintained 3-bedroom, 2-bathroom unit offers an inviting open floor plan, perfect for both relaxation and entertaining. Enjoy the warmth of an electric fireplace in the cozy living area, while the spacious eat in kitchen is equipped with essential appliances including a dishwasher and stacked washer/dryer. Step outside to your private balcony, where serene pond views create a tranquil retreat. The community boasts exceptional amenities, including a refreshing outdoor pool, a fitness center, and scenic jogging paths, ensuring an active lifestyle right at your doorstep. With sidewalks and street lights enhancing the neighborhood's charm, evening strolls become a delightful routine. Thompson Creek Condos is ideally situated near top-rated schools, lush parks, and essential public services, making it a prime location for convenience and community engagement. The association fee covers maintenance and insurance, allowing you to enjoy a worry-free lifestyle. Experience the best of both worlds-relaxation and recreation-within this vibrant community. Whether you're lounging by the pool or exploring the nearby river, this property offers a lifestyle that is both enriching and fulfilling. Don't miss your chance to call this stunning condo home!

1403 Marion Quimby Dr, Stevensville

Listing courtesy of Benson & Mangold, LLC. Contact:

$579,900

Please remove shoes or use shoe covers provided! Welcome to the rarely-available upgraded Hudson model at Perry's Retreat located at 106 Pixie Court. This beautiful unit offers the perfect blend of space, comfort, and modern design on a PREMIUM LOT. This home presents a rare opportunity to own one of the community's most desirable models in a cud-de-sac. The main level features an open concept design that seamlessly connects the kitchen, dining, and living areas, creating an ideal layout for both everyday living and entertaining. A private office with French doors provides the perfect work from home space, while an additional ensuite bedroom on this level offers endless possibilities as a guest room, or hobby space. The upgraded kitchen serves as the heart of the home, showcasing quartz countertops, stainless steel appliances, upgraded backsplash, additional wall oven, and a large island overlooking the spacious living room. Luxury vinyl plank flooring in most of the main level adds both style and durability. Upstairs, the spacious primary suite offers a relaxing retreat with a tray ceiling, two oversized walk-in closets, and a beautifully appointed en-suite bathroom featuring dual vanities, private water closet, and linen closet. Three additional bedrooms, a full bathroom with double sinks, and a convenient upper-level laundry room complete the second floor. Outside, enjoy a backyard that creates a setting for relaxation and entertaining. Community amenities include a playground, open green space for neighborhood events. Conveniently located just minutes from Route 50, residents enjoy easy access to Kent Island, Annapolis, Easton, St. Michaels, Oxford, Tilghman Island, Baltimore, and Washington, D.C. Directly across from the community, the Chesapeake Bay Environmental Center offers hiking trails, kayaking, wildlife viewing, educational programs, and summer camps, allowing you to fully embrace the Eastern Shore lifestyle. Professional photos coming soon!

5 Beds ⋅ 3 Baths

Please remove shoes or use shoe covers provided! Welcome to the rarely-available upgraded Hudson model at Perry's Retreat located at 106 Pixie Court. This beautiful unit offers the perfect blend of space, comfort, and modern design on a PREMIUM LOT. This home presents a rare opportunity to own one of the community's most desirable models in a cud-de-sac. The main level features an open concept design that seamlessly connects the kitchen, dining, and living areas, creating an ideal layout for both everyday living and entertaining. A private office with French doors provides the perfect work from home space, while an additional ensuite bedroom on this level offers endless possibilities as a guest room, or hobby space. The upgraded kitchen serves as the heart of the home, showcasing quartz countertops, stainless steel appliances, upgraded backsplash, additional wall oven, and a large island overlooking the spacious living room. Luxury vinyl plank flooring in most of the main level adds both style and durability. Upstairs, the spacious primary suite offers a relaxing retreat with a tray ceiling, two oversized walk-in closets, and a beautifully appointed en-suite bathroom featuring dual vanities, private water closet, and linen closet. Three additional bedrooms, a full bathroom with double sinks, and a convenient upper-level laundry room complete the second floor. Outside, enjoy a backyard that creates a setting for relaxation and entertaining. Community amenities include a playground, open green space for neighborhood events. Conveniently located just minutes from Route 50, residents enjoy easy access to Kent Island, Annapolis, Easton, St. Michaels, Oxford, Tilghman Island, Baltimore, and Washington, D.C. Directly across from the community, the Chesapeake Bay Environmental Center offers hiking trails, kayaking, wildlife viewing, educational programs, and summer camps, allowing you to fully embrace the Eastern Shore lifestyle. Professional photos coming soon!

106 Pixie Ct, Grasonville

Listing courtesy of HomeSmart. Contact:

$384,900

Price improvement! Welcome home to this beautifully maintained Colonial nestled in the desirable Meadows community of Church Hill. Ideally located between historic Chestertown and Centreville and within the sought-after Queen Anne's County School District, this home offers the perfect blend of comfort, convenience, and timeless style. Step inside through the impressive two-story foyer that welcomes you into a bright and inviting floor plan. The spacious primary suite serves as a private retreat, complete with a, separate shower, and relaxing soaking tub. The home has been exceptionally well cared for and features numerous updates, including a newer roof and HVAC system, providing peace of mind for years to come. New HVAC system installed and serviced by Dixieland energy January 2025, operated by Nest technology. New Roof in July 2025 installed by Economy Roofing with GAF Timberline HDX Lifetime Shingles. New 16x12 Trex Deck with a large poured concrete patio installed in 2024-2025. The partially finished full basement offers endless possibilities with plenty of room for a recreation area, home gym, office, or additional storage. Outside, you'll fall in love with the beautifully landscaped backyard oasis—perfect for entertaining, summer barbecues, or simply relaxing after a long day. Square footage including basement is roughly 2700 sq feet. With its outstanding condition, thoughtful updates, attached garage, and prime location just minutes from shopping, restaurants, and easy access to Route 301, this is a home that truly checks all the boxes. Schedule your private showing today and experience everything 116 Reeand Lane has to offer! Some photos have had personal items removed and have been staged with AI.

Price improvement! Welcome home to this beautifully maintained Colonial nestled in the desirable Meadows community of Church Hill. Ideally located between historic Chestertown and Centreville and within the sought-after Queen Anne's County School District, this home offers the perfect blend of comfort, convenience, and timeless style. Step inside through the impressive two-story foyer that welcomes you into a bright and inviting floor plan. The spacious primary suite serves as a private retreat, complete with a, separate shower, and relaxing soaking tub. The home has been exceptionally well cared for and features numerous updates, including a newer roof and HVAC system, providing peace of mind for years to come. New HVAC system installed and serviced by Dixieland energy January 2025, operated by Nest technology. New Roof in July 2025 installed by Economy Roofing with GAF Timberline HDX Lifetime Shingles. New 16x12 Trex Deck with a large poured concrete patio installed in 2024-2025. The partially finished full basement offers endless possibilities with plenty of room for a recreation area, home gym, office, or additional storage. Outside, you'll fall in love with the beautifully landscaped backyard oasis—perfect for entertaining, summer barbecues, or simply relaxing after a long day. Square footage including basement is roughly 2700 sq feet. With its outstanding condition, thoughtful updates, attached garage, and prime location just minutes from shopping, restaurants, and easy access to Route 301, this is a home that truly checks all the boxes. Schedule your private showing today and experience everything 116 Reeand Lane has to offer! Some photos have had personal items removed and have been staged with AI.

116 Reeand Ln, Church Hill

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

$355,000

*Investor and flipper special* Sitting on almost half an acre, this home offers exceptional value for those looking to build equity! This colonial style home has 2 bedrooms, with potential for 5 and 2 bathrooms with potential for a 3rd. It is districted with some of the best schools in QA County and has quick access to the bay bridge and route 50. This property is a **short sale** and is being sold AS IS. Don't miss the opportunity to own and tap into this homes equity!

*Investor and flipper special* Sitting on almost half an acre, this home offers exceptional value for those looking to build equity! This colonial style home has 2 bedrooms, with potential for 5 and 2 bathrooms with potential for a 3rd. It is districted with some of the best schools in QA County and has quick access to the bay bridge and route 50. This property is a **short sale** and is being sold AS IS. Don't miss the opportunity to own and tap into this homes equity!

123 Kentmorr Rd, Stevensville

Listing courtesy of Douglas Realty LLC. Contact:

$589,999

Experience coastal living at its finest in this stunning 2024-built home located in the sought-after Romancoke community, just steps from the Chesapeake Bay. This beautifully appointed 4-bedroom, 2.5-bath home offers the perfect combination of modern design, comfort, and convenience. The spacious open-concept floor plan is ideal for entertaining, featuring seamless flow between the living, dining, and kitchen areas. High-end custom window blinds add a touch of elegance throughout, while the fully fenced backyard creates the perfect private retreat for relaxing, hosting gatherings, or enjoying time with family and pets. Perfectly situated on a quiet private road, this home offers a peaceful setting with easy access to the bay, making it ideal for boating, fishing, kayaking, or simply enjoying breathtaking waterfront sunsets. Connected to public sewer and built in 2024, you'll enjoy the benefits of newer construction with the peace of mind that comes with modern systems and finishes. Don't miss this opportunity to own a like-new coastal retreat in one of Kent Island's most desirable waterfront communities!

Experience coastal living at its finest in this stunning 2024-built home located in the sought-after Romancoke community, just steps from the Chesapeake Bay. This beautifully appointed 4-bedroom, 2.5-bath home offers the perfect combination of modern design, comfort, and convenience. The spacious open-concept floor plan is ideal for entertaining, featuring seamless flow between the living, dining, and kitchen areas. High-end custom window blinds add a touch of elegance throughout, while the fully fenced backyard creates the perfect private retreat for relaxing, hosting gatherings, or enjoying time with family and pets. Perfectly situated on a quiet private road, this home offers a peaceful setting with easy access to the bay, making it ideal for boating, fishing, kayaking, or simply enjoying breathtaking waterfront sunsets. Connected to public sewer and built in 2024, you'll enjoy the benefits of newer construction with the peace of mind that comes with modern systems and finishes. Don't miss this opportunity to own a like-new coastal retreat in one of Kent Island's most desirable waterfront communities!

200 Ackerman Dr, Stevensville

Listing courtesy of Rise Real Estate, LLC. Contact:

$379,000

Charming Cape Cod home offering both residential comfort and commercial potential, beautifully updated with modern finishes while maintaining its classic character. This move-in-ready property features 2 bedrooms, 1 full bathroom, an inviting sunroom entry, and luxury vinyl plank flooring throughout. The updated kitchen showcases stainless steel appliances, an induction range, new refrigerator, granite countertops, and refreshed cabinetry. Recent improvements include the bathroom, double-pane windows, roof, siding, HVAC system, well system, electrical panel, and front entry door. The property also features an oversized detached garage with side entry and a spacious asphalt driveway for added convenience. Minutes to Kent Island, close to major hwy. A rare opportunity to own a versatile property with endless possibilities!

2 Beds ⋅ 1 Baths

Charming Cape Cod home offering both residential comfort and commercial potential, beautifully updated with modern finishes while maintaining its classic character. This move-in-ready property features 2 bedrooms, 1 full bathroom, an inviting sunroom entry, and luxury vinyl plank flooring throughout. The updated kitchen showcases stainless steel appliances, an induction range, new refrigerator, granite countertops, and refreshed cabinetry. Recent improvements include the bathroom, double-pane windows, roof, siding, HVAC system, well system, electrical panel, and front entry door. The property also features an oversized detached garage with side entry and a spacious asphalt driveway for added convenience. Minutes to Kent Island, close to major hwy. A rare opportunity to own a versatile property with endless possibilities!

3801 Main St, Grasonville

Listing courtesy of Fairfax Realty Select. Contact:

$869,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit 2943, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$769,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

102 Boatswain Way Unit 2932, Chester

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact:

$739,000

Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing. “Some photos are virtually staged”

4 Beds ⋅ 4 Baths

Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing. “Some photos are virtually staged”

134 Richard Ingle Way, Chester

Listing courtesy of Redfin Corp. Contact:

$585,000

Welcome to this stunning home in the picturesque 55+ Community of Bay Bridge Cove - the place for Kent Island living at its best, so close to the waters of the Chesapeake Bay. This 3-bedroom, 3-bath home offers so many upgraded features. Conveniently located across from the community center and backing up to quiet, tree-lined space, you are steps away from enjoying all the amenities the neighborhood has to offer. Welcoming you at the front of the home is your own private courtyard, with space to sit and relax or socialize with friends under the strings of cafe lights. Walk inside to the warm-toned luxury wood plank vinyl floors throughout the entire first floor; abundant light spills in to accent the paneled foyer with upper crown molding. The roomy kitchen features soft-close cabinets/drawers with lots of storage, pull-out trash and recycle bins, a corner cabinet with lazy-susan shelving, stainless steel appliances, premium countertops and backsplash, under-the-counter lighting, and updated cabinet knobs and pendant lights. The main level great room has plenty of space for a large dining table and your comfortable living room furniture, and features a cozy gas fireplace (and includes a convenient wall mount for your TV). Step into the bright and airy sunroom at the back of the home - make it your book nook, office, or a spot to enjoy your guests. The primary bedroom features a tray ceiling, 2 walk-in closets (one is huge!), and a private bath with tiled shower and ceramic tiled flooring. The 2nd bedroom on the first floor connects to the hall bath. A sizable laundry room includes upgraded Samsung appliances, shelving, and a storage closet. Upstairs you'll find a relaxing retreat with a large loft area, a bedroom with walk-in closet, and a full bath. A bonus feature of this home is the beautifully enhanced loft wall on each side with added railing, making this space safe for the little ones while maintaining the line of sight to the first floor. With ceiling fans throughout, added storm doors on the front and back with pull-down screens, unique custom blinds on all windows matched perfectly to the function of each room, and an irrigation system for low-maintenance gardening, this home may be the perfect one you've been looking for! This thriving community has it all - a calendar of activities and outings, bocce and pickleball, picnics at the crab shack, a pool, indoor gym, library, game rooms, community garden and fresh herb garden, walking paths around the beautifully landscaped ponds, and quick access to the Cross Island Trail right next to the neighborhood. There's so much to do here!

Welcome to this stunning home in the picturesque 55+ Community of Bay Bridge Cove - the place for Kent Island living at its best, so close to the waters of the Chesapeake Bay. This 3-bedroom, 3-bath home offers so many upgraded features. Conveniently located across from the community center and backing up to quiet, tree-lined space, you are steps away from enjoying all the amenities the neighborhood has to offer. Welcoming you at the front of the home is your own private courtyard, with space to sit and relax or socialize with friends under the strings of cafe lights. Walk inside to the warm-toned luxury wood plank vinyl floors throughout the entire first floor; abundant light spills in to accent the paneled foyer with upper crown molding. The roomy kitchen features soft-close cabinets/drawers with lots of storage, pull-out trash and recycle bins, a corner cabinet with lazy-susan shelving, stainless steel appliances, premium countertops and backsplash, under-the-counter lighting, and updated cabinet knobs and pendant lights. The main level great room has plenty of space for a large dining table and your comfortable living room furniture, and features a cozy gas fireplace (and includes a convenient wall mount for your TV). Step into the bright and airy sunroom at the back of the home - make it your book nook, office, or a spot to enjoy your guests. The primary bedroom features a tray ceiling, 2 walk-in closets (one is huge!), and a private bath with tiled shower and ceramic tiled flooring. The 2nd bedroom on the first floor connects to the hall bath. A sizable laundry room includes upgraded Samsung appliances, shelving, and a storage closet. Upstairs you'll find a relaxing retreat with a large loft area, a bedroom with walk-in closet, and a full bath. A bonus feature of this home is the beautifully enhanced loft wall on each side with added railing, making this space safe for the little ones while maintaining the line of sight to the first floor. With ceiling fans throughout, added storm doors on the front and back with pull-down screens, unique custom blinds on all windows matched perfectly to the function of each room, and an irrigation system for low-maintenance gardening, this home may be the perfect one you've been looking for! This thriving community has it all - a calendar of activities and outings, bocce and pickleball, picnics at the crab shack, a pool, indoor gym, library, game rooms, community garden and fresh herb garden, walking paths around the beautifully landscaped ponds, and quick access to the Cross Island Trail right next to the neighborhood. There's so much to do here!

222 Moorings Cir Unit 126, Stevensville

Listing courtesy of The KW Collective. Contact:

$769,990

Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in December 2026, this home combines modern comfort with functional and stylish living spaces. The main living area features a dry bar and an electric fireplace, creating a warm and inviting atmosphere perfect for both relaxing and entertaining. A dedicated home office with lited French doors provides a private and elegant workspace. The kitchen is designed for both everyday living and convenience, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, tile backsplash, and quartz countertops. Luxury vinyl plank flooring flows throughout the home, with tile flooring in both full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a comfortable and functional retreat. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.