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Coming Soon - You won't want to miss this one. Fully renovated home in the heart of Church Hill. New everything - new roof, windows, doors, flooring, kitchen, bathrooms, electric, plumbing and more! This is a must see. Professional photos coming soon.

227 New St, Church Hill

Listing courtesy of Compass. Contact:

$420,000

Welcome to 331 Utah Rd. This well-maintained home is being offered for the first time and is conveniently located so close to the water in Kent Island Estates. Featuring 3 bedrooms and 2 full bathrooms, the property includes an updated primary bedroom, spacious living room and dining room, and an inviting kitchen. The finished lower level provides additional living space and includes a woodstove for added warmth and comfort. Enjoy the outdoors year-round with a large lot and rear fence, as well as a sunroom and a screened porch—perfect for relaxing, entertaining, and enjoying the surrounding setting. Don’t miss the opportunity to make this your forever home.

Welcome to 331 Utah Rd. This well-maintained home is being offered for the first time and is conveniently located so close to the water in Kent Island Estates. Featuring 3 bedrooms and 2 full bathrooms, the property includes an updated primary bedroom, spacious living room and dining room, and an inviting kitchen. The finished lower level provides additional living space and includes a woodstove for added warmth and comfort. Enjoy the outdoors year-round with a large lot and rear fence, as well as a sunroom and a screened porch—perfect for relaxing, entertaining, and enjoying the surrounding setting. Don’t miss the opportunity to make this your forever home.

331 Utah Rd, Stevensville

Listing courtesy of Curtis Real Estate Company. Contact:

$979,990

Welcome to the Mykonos, a beautifully designed home that blends an open-concept floorplan with Classic-inspired style, creating the perfect balance of comfort and functionality. This spacious home features 4 bedrooms, 3.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight guests. Designed with versatility in mind, the inviting fireplace serves as a cozy focal point for the main living area, while the screened patio provides the perfect outdoor retreat for enjoying fresh air in comfort throughout the seasons. Thoughtful design and quality craftsmanship come together to create a home that is both stylish and functional. For a complete list of included features and finishes, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Welcome to the Mykonos, a beautifully designed home that blends an open-concept floorplan with Classic-inspired style, creating the perfect balance of comfort and functionality. This spacious home features 4 bedrooms, 3.5 bathrooms, and a 3-car garage, offering plenty of room for everyday living, entertaining, and hosting overnight guests. Designed with versatility in mind, the inviting fireplace serves as a cozy focal point for the main living area, while the screened patio provides the perfect outdoor retreat for enjoying fresh air in comfort throughout the seasons. Thoughtful design and quality craftsmanship come together to create a home that is both stylish and functional. For a complete list of included features and finishes, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

727 Warbler Way, Chester

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

$700,000

Welcome to 244 Warbler Way, a beautifully appointed Jenkins model built in 2025 and located in the sought-after 55+ community of Four Seasons at Kent Island. This thoughtfully designed 2-bedroom, 2-bath home offers stylish, low-maintenance living with upgrades throughout. Luxury vinyl plank flooring flows through the main living areas, leading to a bright, open-concept kitchen featuring upgraded finishes and a premium GE Café appliance package. The kitchen opens seamlessly to the dining and living spaces, creating an inviting layout perfect for both everyday living and entertaining. A beautiful propane fireplace anchors the living room, adding warmth and character to the heart of the home. Enjoy easy indoor-outdoor living from the screened porch or step outside to the hardscaped patio—an ideal setting for morning coffee, relaxing evenings, or entertaining friends. Built just last year, this home offers the benefits of newer construction without the wait. Located in Four Seasons at Kent Island, residents enjoy a vibrant 55+ lifestyle with resort-style amenities and a prime Eastern Shore location convenient to the Chesapeake Bay, shopping, dining, and the Bay Bridge. Move right in and enjoy everything this beautiful home and community have to offer!

2 Beds ⋅ 2 Baths

Welcome to 244 Warbler Way, a beautifully appointed Jenkins model built in 2025 and located in the sought-after 55+ community of Four Seasons at Kent Island. This thoughtfully designed 2-bedroom, 2-bath home offers stylish, low-maintenance living with upgrades throughout. Luxury vinyl plank flooring flows through the main living areas, leading to a bright, open-concept kitchen featuring upgraded finishes and a premium GE Café appliance package. The kitchen opens seamlessly to the dining and living spaces, creating an inviting layout perfect for both everyday living and entertaining. A beautiful propane fireplace anchors the living room, adding warmth and character to the heart of the home. Enjoy easy indoor-outdoor living from the screened porch or step outside to the hardscaped patio—an ideal setting for morning coffee, relaxing evenings, or entertaining friends. Built just last year, this home offers the benefits of newer construction without the wait. Located in Four Seasons at Kent Island, residents enjoy a vibrant 55+ lifestyle with resort-style amenities and a prime Eastern Shore location convenient to the Chesapeake Bay, shopping, dining, and the Bay Bridge. Move right in and enjoy everything this beautiful home and community have to offer!

244 Warbler Way, Chester

Listing courtesy of Samson Properties. Contact:

$499,900

A short stroll from the Eastern Bay front community center, this brand new home is complete and ready for you to move in before the holidays! One level living with LVP flooring throughout the entire home! Quartz countertops on classic white shaker cabinets and stainless steel appliances complete the modern farmhouse feel of this kitchen. Split floor plan gives flexibility to the two guest rooms which could be used as an office or sitting room as well. Master suite is on the rear of the home with a spacious walk in closet and luxurious bathroom with double vanities, tiled shower, and more. Two car garage and full front porch bring the perfect blend of utility and charm.

A short stroll from the Eastern Bay front community center, this brand new home is complete and ready for you to move in before the holidays! One level living with LVP flooring throughout the entire home! Quartz countertops on classic white shaker cabinets and stainless steel appliances complete the modern farmhouse feel of this kitchen. Split floor plan gives flexibility to the two guest rooms which could be used as an office or sitting room as well. Master suite is on the rear of the home with a spacious walk in closet and luxurious bathroom with double vanities, tiled shower, and more. Two car garage and full front porch bring the perfect blend of utility and charm.

214 Penny Ln, Stevensville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$559,900

Welcome to 200 Anchor Lane, where the charm of an established Kent Island neighborhood meets the convenience of a nearly new home! Situated on a spacious 0.42-acre corner lot with NO HOA, this 3-bedroom, 2-bath rancher offers approximately 1,640 square feet of thoughtfully redesigned living space. Originally built in 1977, the home underwent an extensive renovation in 2025, taken down to the studs and rebuilt with modern finishes and systems while preserving its original textured masonry façade and chimney. Step inside to discover a bright, open-concept layout where the dining area flows seamlessly into the kitchen and family room. The beautifully appointed kitchen features Samsung Bespoke appliances, a gas range, generous cabinetry and an oversized island offering plenty of space for meal preparation, gathering and entertaining. The spacious primary suite includes a walk-in closet, additional closet and private bath with a walk-in shower and double vanity. Two additional bedrooms offer generous closet space and share a thoughtfully updated hall bath. Beyond the cosmetic improvements, nearly every major component has been updated, including electrical, plumbing, HVAC, roof, insulation, windows and doors! Additional features include smart lighting, whole-home audio, an EV charger, generator hookup, interior fire sprinkler system, conditioned and encapsulated crawlspace, and a NEW well installed in 2026. Enjoy outdoor living on the patio with plenty of yard space for gardening, recreation or simply relaxing. Located in the desirable Castle Marina area of Chester, this property puts the Eastern Shore lifestyle within easy reach! Just a few houses down from Castle Marina and Freedom Boat Club, boating enthusiasts will appreciate the convenient proximity to the water. Enjoy nearby dining, the Cross Island Trail and easy access to Route 50 for commuting to Annapolis, Baltimore and beyond. An exceptional opportunity to enjoy the benefits of extensive modern renovations in an established Kent Island location!

Welcome to 200 Anchor Lane, where the charm of an established Kent Island neighborhood meets the convenience of a nearly new home! Situated on a spacious 0.42-acre corner lot with NO HOA, this 3-bedroom, 2-bath rancher offers approximately 1,640 square feet of thoughtfully redesigned living space. Originally built in 1977, the home underwent an extensive renovation in 2025, taken down to the studs and rebuilt with modern finishes and systems while preserving its original textured masonry façade and chimney. Step inside to discover a bright, open-concept layout where the dining area flows seamlessly into the kitchen and family room. The beautifully appointed kitchen features Samsung Bespoke appliances, a gas range, generous cabinetry and an oversized island offering plenty of space for meal preparation, gathering and entertaining. The spacious primary suite includes a walk-in closet, additional closet and private bath with a walk-in shower and double vanity. Two additional bedrooms offer generous closet space and share a thoughtfully updated hall bath. Beyond the cosmetic improvements, nearly every major component has been updated, including electrical, plumbing, HVAC, roof, insulation, windows and doors! Additional features include smart lighting, whole-home audio, an EV charger, generator hookup, interior fire sprinkler system, conditioned and encapsulated crawlspace, and a NEW well installed in 2026. Enjoy outdoor living on the patio with plenty of yard space for gardening, recreation or simply relaxing. Located in the desirable Castle Marina area of Chester, this property puts the Eastern Shore lifestyle within easy reach! Just a few houses down from Castle Marina and Freedom Boat Club, boating enthusiasts will appreciate the convenient proximity to the water. Enjoy nearby dining, the Cross Island Trail and easy access to Route 50 for commuting to Annapolis, Baltimore and beyond. An exceptional opportunity to enjoy the benefits of extensive modern renovations in an established Kent Island location!

200 Anchor Ln, Chester

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

$675,000

Designed for effortless, low-maintenance living, this beautifully appointed three-bedroom, 2.5-bath condominium offers approximately 2,600 square feet of thoughtfully designed living space, combining comfort, elegance, and an exceptional collection of resort-style amenities. The open-concept living, dining, and kitchen areas create a welcoming flow, ideal for both everyday living and entertaining. Expansive windows fill the home with natural light, while the inviting walk-out porch provides a peaceful setting overlooking ponds on two sides, with seasonal glimpses of the Chester River. The spacious primary suite is privately situated on one side of the residence and features a generous sitting room, two walk-in closets, and a comfortable retreat-like atmosphere. On the opposite side of the condominium, two additional private bedrooms, each with a walk-in closet, share a full bath, offering an ideal layout for family and guests. The well-appointed kitchen features 42-inch cabinetry, beautiful white quartz countertops with subtle gray veining, and a timeless neutral palette that provides the perfect canvas for your personal style. Located within the highly desirable Four Seasons community, residents enjoy an exceptional lifestyle with an impressive array of amenities. Highlights include indoor and outdoor swimming pools, tennis courts, playgrounds, fire pits, a community pier, kayak park with launch, and water access. The community also offers a spectacular 22,000-square-foot clubhouse, fitness facilities, inviting gathering rooms within each building, and multiple spaces designed for entertaining and socializing, including bar areas with televisions. Whether enjoying the peaceful pond views from your porch, taking advantage of the outstanding community amenities, or simply appreciating the ease of condominium living, this residence offers a wonderful opportunity to enjoy comfort, convenience, and a resort-inspired lifestyle. Walking trails bot in the community and right outside of community. Close commute to the bay bridge, shopping, churches and doctors and much more....

Designed for effortless, low-maintenance living, this beautifully appointed three-bedroom, 2.5-bath condominium offers approximately 2,600 square feet of thoughtfully designed living space, combining comfort, elegance, and an exceptional collection of resort-style amenities. The open-concept living, dining, and kitchen areas create a welcoming flow, ideal for both everyday living and entertaining. Expansive windows fill the home with natural light, while the inviting walk-out porch provides a peaceful setting overlooking ponds on two sides, with seasonal glimpses of the Chester River. The spacious primary suite is privately situated on one side of the residence and features a generous sitting room, two walk-in closets, and a comfortable retreat-like atmosphere. On the opposite side of the condominium, two additional private bedrooms, each with a walk-in closet, share a full bath, offering an ideal layout for family and guests. The well-appointed kitchen features 42-inch cabinetry, beautiful white quartz countertops with subtle gray veining, and a timeless neutral palette that provides the perfect canvas for your personal style. Located within the highly desirable Four Seasons community, residents enjoy an exceptional lifestyle with an impressive array of amenities. Highlights include indoor and outdoor swimming pools, tennis courts, playgrounds, fire pits, a community pier, kayak park with launch, and water access. The community also offers a spectacular 22,000-square-foot clubhouse, fitness facilities, inviting gathering rooms within each building, and multiple spaces designed for entertaining and socializing, including bar areas with televisions. Whether enjoying the peaceful pond views from your porch, taking advantage of the outstanding community amenities, or simply appreciating the ease of condominium living, this residence offers a wonderful opportunity to enjoy comfort, convenience, and a resort-inspired lifestyle. Walking trails bot in the community and right outside of community. Close commute to the bay bridge, shopping, churches and doctors and much more....

190 Harrier Way Unit 24, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

$1,775,000

Exceptional Wye River Waterfront Living – A Boater’s Paradise! An extraordinary opportunity to enjoy the very best of Wye River waterfront living! Perfectly positioned atop a bluff, this beautifully maintained home captures breathtaking panoramic water views and offers an exceptional setting for boating enthusiasts and those who appreciate the beauty of waterfront living. With approximately 6 feet of water at the pier and a boat lift with a 12,000-pound capacity, this property is ready for your boating adventures. The southeast-facing orientation provides beautiful natural light and stunning water views throughout the home. Spend your days fishing and crabbing on the Wye, cruising to St. Michaels, or taking your boat to one of the area's wonderful waterfront restaurants for a memorable lunch or dinner. Conveniently located approximately six miles from Route 50, the property offers the perfect balance of a peaceful waterfront setting and accessibility. There is living space of 3,990 of finished sq. feet and an additional 350 unfinished sq. footage for a total of 4,340 sq. ft. Inside, the home is thoughtfully designed across three levels, offering generous living spaces and exceptional flexibility. There are two primary suites, one on the main level and another on the second floor. Hardwood flooring extends throughout much of the first floor, where expansive, open living areas take full advantage of the beautiful water views. The updated kitchen, spacious sunroom, three fireplaces, and abundant natural light create a warm and inviting atmosphere. Many rooms enjoy beautiful water views, making the river a constant backdrop to everyday living. An especially desirable feature for the area is the full basement, approximately three-quarters finished. This versatile space offers excellent possibilities for a home office or business setup, recreation room, home gym, or additional entertainment space. The third level provides three additional bedrooms and two full bathrooms, with all three bedrooms enjoying water views. A walkout deck overlooking the water creates another wonderful place to relax and take in the peaceful surroundings. Outdoor living is equally impressive. A large brick patio along the waterfront offers an ideal setting for entertaining and is ready for your vision of an outdoor kitchen. The expansive, open lawn and beautifully maintained landscaping provide plenty of room to enjoy the outdoors, gather with family and friends, or simply appreciate the privacy and natural beauty of this exceptional property. Meticulously maintained and thoughtfully designed for both comfortable everyday living and gracious entertaining, this Wye River waterfront home offers an exceptional combination of panoramic views, boating amenities, generous living spaces, and a convenient location. Experience the Wye River lifestyle—where boating, entertaining, and spectacular waterfront living come together!

Exceptional Wye River Waterfront Living – A Boater’s Paradise! An extraordinary opportunity to enjoy the very best of Wye River waterfront living! Perfectly positioned atop a bluff, this beautifully maintained home captures breathtaking panoramic water views and offers an exceptional setting for boating enthusiasts and those who appreciate the beauty of waterfront living. With approximately 6 feet of water at the pier and a boat lift with a 12,000-pound capacity, this property is ready for your boating adventures. The southeast-facing orientation provides beautiful natural light and stunning water views throughout the home. Spend your days fishing and crabbing on the Wye, cruising to St. Michaels, or taking your boat to one of the area's wonderful waterfront restaurants for a memorable lunch or dinner. Conveniently located approximately six miles from Route 50, the property offers the perfect balance of a peaceful waterfront setting and accessibility. There is living space of 3,990 of finished sq. feet and an additional 350 unfinished sq. footage for a total of 4,340 sq. ft. Inside, the home is thoughtfully designed across three levels, offering generous living spaces and exceptional flexibility. There are two primary suites, one on the main level and another on the second floor. Hardwood flooring extends throughout much of the first floor, where expansive, open living areas take full advantage of the beautiful water views. The updated kitchen, spacious sunroom, three fireplaces, and abundant natural light create a warm and inviting atmosphere. Many rooms enjoy beautiful water views, making the river a constant backdrop to everyday living. An especially desirable feature for the area is the full basement, approximately three-quarters finished. This versatile space offers excellent possibilities for a home office or business setup, recreation room, home gym, or additional entertainment space. The third level provides three additional bedrooms and two full bathrooms, with all three bedrooms enjoying water views. A walkout deck overlooking the water creates another wonderful place to relax and take in the peaceful surroundings. Outdoor living is equally impressive. A large brick patio along the waterfront offers an ideal setting for entertaining and is ready for your vision of an outdoor kitchen. The expansive, open lawn and beautifully maintained landscaping provide plenty of room to enjoy the outdoors, gather with family and friends, or simply appreciate the privacy and natural beauty of this exceptional property. Meticulously maintained and thoughtfully designed for both comfortable everyday living and gracious entertaining, this Wye River waterfront home offers an exceptional combination of panoramic views, boating amenities, generous living spaces, and a convenient location. Experience the Wye River lifestyle—where boating, entertaining, and spectacular waterfront living come together!

377 Hemsley Dr, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

$550,000

Two Homes, Endless Possibilities, and a Chesapeake Bay Lifestyle! Discover a truly unique opportunity in Bay City! This one-of-a-kind property offers not just one, but two separate homes, a two-car garage, and an incredible entertainment space, creating the perfect setting for a family retreat, multigenerational living, hosting guests, or generating vacation rental income! The main residence welcomes you with a spacious living room featuring a cozy fireplace, along with a family room boasting a soaring vaulted ceiling, built-in bar, and atrium doors that open onto an expansive deck. The kitchen is centrally located and open to both the Living and Family rooms. With three generously sized bedrooms and two full baths, there's plenty of room for family and friends to relax and enjoy all the comforts of home. But that's just the beginning! Just next door, you'll discover a fully furnished guest house offering exceptional flexibility as an Airbnb, vacation rental, in-law suite, or private accommodations for overnight guests. This charming retreat features a spacious living room, a private bedroom, a well-appointed kitchen with a skylight above the island and seating for two, plus sliding glass doors leading to a partially private yard. A spacious full bath completes this inviting space. And there's still more to explore! The attached two-car garage has been transformed into an extraordinary entertainment destination! Connected to the guest house, this incredible recreation area is designed for fun and relaxation. Accommodations include two bunk beds sleeping up to six, a pool table, comfortable lounge areas, a game area, and a separate adult gathering space complete with a bar. You'll also find a half bath and laundry area, making this an ideal space for entertaining family and friends. Step outside to enjoy the patio and shared fire pit, perfect for gathering, unwinding, and making memories long after the sun goes down. And then there's Bay City! Enjoy the wonderful lifestyle of this water-privileged Chesapeake Bay community, offering residents access to a boat ramp, fishing pier, picnic pavilion, expansive playground, and picnic areas right along the beautiful, scenic Chesapeake Bay boast incredible sunsets overlooking Annapolis! Whether you're searching for a family getaway, a property with room for everyone, a multigenerational living arrangement, or an investment opportunity with vacation rental potential, this property delivers possibilities you won't find every day. Two homes. Endless entertainment. Chesapeake Bay living. Income-producing potential. Properties this unique rarely come along! Don't miss your opportunity to own this extraordinary Bay City retreat. Vacation rental financials are available for buyers interested in exploring the investment potential!

Two Homes, Endless Possibilities, and a Chesapeake Bay Lifestyle! Discover a truly unique opportunity in Bay City! This one-of-a-kind property offers not just one, but two separate homes, a two-car garage, and an incredible entertainment space, creating the perfect setting for a family retreat, multigenerational living, hosting guests, or generating vacation rental income! The main residence welcomes you with a spacious living room featuring a cozy fireplace, along with a family room boasting a soaring vaulted ceiling, built-in bar, and atrium doors that open onto an expansive deck. The kitchen is centrally located and open to both the Living and Family rooms. With three generously sized bedrooms and two full baths, there's plenty of room for family and friends to relax and enjoy all the comforts of home. But that's just the beginning! Just next door, you'll discover a fully furnished guest house offering exceptional flexibility as an Airbnb, vacation rental, in-law suite, or private accommodations for overnight guests. This charming retreat features a spacious living room, a private bedroom, a well-appointed kitchen with a skylight above the island and seating for two, plus sliding glass doors leading to a partially private yard. A spacious full bath completes this inviting space. And there's still more to explore! The attached two-car garage has been transformed into an extraordinary entertainment destination! Connected to the guest house, this incredible recreation area is designed for fun and relaxation. Accommodations include two bunk beds sleeping up to six, a pool table, comfortable lounge areas, a game area, and a separate adult gathering space complete with a bar. You'll also find a half bath and laundry area, making this an ideal space for entertaining family and friends. Step outside to enjoy the patio and shared fire pit, perfect for gathering, unwinding, and making memories long after the sun goes down. And then there's Bay City! Enjoy the wonderful lifestyle of this water-privileged Chesapeake Bay community, offering residents access to a boat ramp, fishing pier, picnic pavilion, expansive playground, and picnic areas right along the beautiful, scenic Chesapeake Bay boast incredible sunsets overlooking Annapolis! Whether you're searching for a family getaway, a property with room for everyone, a multigenerational living arrangement, or an investment opportunity with vacation rental potential, this property delivers possibilities you won't find every day. Two homes. Endless entertainment. Chesapeake Bay living. Income-producing potential. Properties this unique rarely come along! Don't miss your opportunity to own this extraordinary Bay City retreat. Vacation rental financials are available for buyers interested in exploring the investment potential!

709 Chesapeake Dr, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

$550,000

AN EXCEPTIONAL OPPORTUNITY IN PROSPECT BAY! Discover an attractively priced opportunity to enjoy the exceptional lifestyle of this sought-after waterfront and golf community. Offered at $550,000, this distinctive contemporary home is nestled on approximately one acre surrounded by mature trees and peaceful natural surroundings. Offering nearly 2,850 square feet of living space, the residence features three bedrooms, two-and-a-half baths, and a versatile floor plan with two main-level bedrooms. The impressive great room showcases soaring vaulted ceilings, a dramatic brick fireplace, and expansive glass doors opening to a spacious deck and tranquil wooded setting. Abundant natural light fills the interior, creating a wonderful connection between indoor and outdoor living. Overlooking the great room, a generously sized loft offers wonderful flexibility for a home office, creative studio, additional gathering space, or the potential for a fourth bedroom with appropriate modifications and approvals. The generously sized kitchen features abundant cabinetry, a center island, and an adjoining breakfast area, offering plenty of space and possibilities for personalization. Significant improvements include a roof and HVAC system replaced in 2021. Beyond the home, enjoy the exceptional amenities of Prospect Bay, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, private marina, and community boat ramp with access to the Chesapeake Bay. A wonderful opportunity to embrace the Prospect Bay lifestyle at an attractive price, with the freedom to make this home uniquely your own. Beyond the home, enjoy the exceptional amenities of Prospect Bay, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, private marina, and community boat ramp with access to the Chesapeake Bay. A wonderful opportunity to embrace the Prospect Bay lifestyle at an attractive price, with the freedom to make this home uniquely your own.

AN EXCEPTIONAL OPPORTUNITY IN PROSPECT BAY! Discover an attractively priced opportunity to enjoy the exceptional lifestyle of this sought-after waterfront and golf community. Offered at $550,000, this distinctive contemporary home is nestled on approximately one acre surrounded by mature trees and peaceful natural surroundings. Offering nearly 2,850 square feet of living space, the residence features three bedrooms, two-and-a-half baths, and a versatile floor plan with two main-level bedrooms. The impressive great room showcases soaring vaulted ceilings, a dramatic brick fireplace, and expansive glass doors opening to a spacious deck and tranquil wooded setting. Abundant natural light fills the interior, creating a wonderful connection between indoor and outdoor living. Overlooking the great room, a generously sized loft offers wonderful flexibility for a home office, creative studio, additional gathering space, or the potential for a fourth bedroom with appropriate modifications and approvals. The generously sized kitchen features abundant cabinetry, a center island, and an adjoining breakfast area, offering plenty of space and possibilities for personalization. Significant improvements include a roof and HVAC system replaced in 2021. Beyond the home, enjoy the exceptional amenities of Prospect Bay, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, private marina, and community boat ramp with access to the Chesapeake Bay. A wonderful opportunity to embrace the Prospect Bay lifestyle at an attractive price, with the freedom to make this home uniquely your own. Beyond the home, enjoy the exceptional amenities of Prospect Bay, including an 18-hole championship golf course, clubhouse restaurant, swimming pool, tennis and pickleball courts, private marina, and community boat ramp with access to the Chesapeake Bay. A wonderful opportunity to embrace the Prospect Bay lifestyle at an attractive price, with the freedom to make this home uniquely your own.

24 Fairway Is, Grasonville

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

$320,000

***COMING SOON*** Freshly painted, new kitchen cabinets, new carpet throughout. This spacious 3 bedroom, 2.5 bath, 2 story condo is move in ready and available immediately. More info to come.

***COMING SOON*** Freshly painted, new kitchen cabinets, new carpet throughout. This spacious 3 bedroom, 2.5 bath, 2 story condo is move in ready and available immediately. More info to come.

55 Queen Caroline Ct, Chester

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

$549,000

Experience the charm of Eastern Shore living at 618 Love Point Road, where timeless farmhouse character meets modern comfort in the heart of Stevensville. Just moments from historic downtown Stevensville, Old Love Point Park, and Kent Island High School, this beautifully restored home offers an inviting combination of character, convenience, and coastal lifestyle. Offering more than 2,300 square feet of thoughtfully updated living space, this three-bedroom, two-and-a-half-bath residence blends classic architectural details with modern finishes. Hardwood floors, abundant natural light, fresh interior paint, and new window treatments create a warm and welcoming atmosphere throughout. The main level flows effortlessly from the inviting living room into the dining area and beautifully appointed kitchen. Designed for both everyday living and entertaining, the kitchen features custom cabinetry, a classic farmhouse sink, and a built-in coffee bar with wine cooler. A newer roof and previously updated major utilities provide additional peace of mind. Upstairs, three comfortable bedrooms and two tastefully renovated bathrooms offer inviting private retreats. Outside, the expansive, level backyard provides a wonderful setting for entertaining, recreation, or simply relaxing. Beautiful landscaping and a charming gazebo create an inviting outdoor retreat, while a detached bonus space offers exceptional versatility for a home office, fitness studio, creative workspace, or additional recreational space. The location is equally appealing. Enjoy morning coffee on the front porch, take a leisurely stroll through Old Love Point Park, or walk or bike into historic downtown Stevensville to explore its restaurants, coffee shops, and boutiques. Convenient access to Route 50 and the Chesapeake Bay Bridge makes commuting to Annapolis and beyond a breeze. With its classic farmhouse appeal, modern updates, generous outdoor space, and desirable Kent Island location, 618 Love Point Road offers an exceptional opportunity to enjoy the relaxed lifestyle of Maryland’s Eastern Shore.

Experience the charm of Eastern Shore living at 618 Love Point Road, where timeless farmhouse character meets modern comfort in the heart of Stevensville. Just moments from historic downtown Stevensville, Old Love Point Park, and Kent Island High School, this beautifully restored home offers an inviting combination of character, convenience, and coastal lifestyle. Offering more than 2,300 square feet of thoughtfully updated living space, this three-bedroom, two-and-a-half-bath residence blends classic architectural details with modern finishes. Hardwood floors, abundant natural light, fresh interior paint, and new window treatments create a warm and welcoming atmosphere throughout. The main level flows effortlessly from the inviting living room into the dining area and beautifully appointed kitchen. Designed for both everyday living and entertaining, the kitchen features custom cabinetry, a classic farmhouse sink, and a built-in coffee bar with wine cooler. A newer roof and previously updated major utilities provide additional peace of mind. Upstairs, three comfortable bedrooms and two tastefully renovated bathrooms offer inviting private retreats. Outside, the expansive, level backyard provides a wonderful setting for entertaining, recreation, or simply relaxing. Beautiful landscaping and a charming gazebo create an inviting outdoor retreat, while a detached bonus space offers exceptional versatility for a home office, fitness studio, creative workspace, or additional recreational space. The location is equally appealing. Enjoy morning coffee on the front porch, take a leisurely stroll through Old Love Point Park, or walk or bike into historic downtown Stevensville to explore its restaurants, coffee shops, and boutiques. Convenient access to Route 50 and the Chesapeake Bay Bridge makes commuting to Annapolis and beyond a breeze. With its classic farmhouse appeal, modern updates, generous outdoor space, and desirable Kent Island location, 618 Love Point Road offers an exceptional opportunity to enjoy the relaxed lifestyle of Maryland’s Eastern Shore.

618 Love Point Rd, Stevensville

Listing courtesy of TTR Sotheby's International Realty. Contact:

$735,000

Experience the pinnacle of coastal luxury in this breathtaking top-floor penthouse at K. Hovnanian’s Four Seasons at Kent Island. This highly coveted "Chester" floor plan delivers unparalleled, sun-drenched resort-style living with spectacular water views from nearly every vantage point. The open-concept layout features a gourmet kitchen with stainless steel appliances, a spacious great room anchored by a cozy fireplace, and an elegant dry bar perfect for entertaining. Retreat to the pristine owner's suite, complete with a dramatic tray ceiling, spa-like bath, and direct access to an expansive waterside balcony where you can watch the boats glide by. Living here feels like a permanent vacation. Enjoy world-class community amenities, including a 24,000 sq. ft. clubhouse, indoor and outdoor pools with tiki huts, a state-of-the-art fitness center, tennis and pickleball courts, and a community pier. Complete with a private garage and dedicated storage, this lock-and-leave sanctuary offers the effortless Eastern Shore lifestyle you deserve.

2 Beds ⋅ 3 Baths

Experience the pinnacle of coastal luxury in this breathtaking top-floor penthouse at K. Hovnanian’s Four Seasons at Kent Island. This highly coveted "Chester" floor plan delivers unparalleled, sun-drenched resort-style living with spectacular water views from nearly every vantage point. The open-concept layout features a gourmet kitchen with stainless steel appliances, a spacious great room anchored by a cozy fireplace, and an elegant dry bar perfect for entertaining. Retreat to the pristine owner's suite, complete with a dramatic tray ceiling, spa-like bath, and direct access to an expansive waterside balcony where you can watch the boats glide by. Living here feels like a permanent vacation. Enjoy world-class community amenities, including a 24,000 sq. ft. clubhouse, indoor and outdoor pools with tiki huts, a state-of-the-art fitness center, tennis and pickleball courts, and a community pier. Complete with a private garage and dedicated storage, this lock-and-leave sanctuary offers the effortless Eastern Shore lifestyle you deserve.

121 Switchgrass Way Unit 42, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

$429,900

This charming ranch-style home, built in 1978, offers a serene retreat on a spacious 0.33-acre lot, perfect for those who appreciate the beauty of nature. With three cozy bedrooms and two full bathrooms, this residence is designed for comfort and ease. The inviting screened porch and deck provide ideal spaces for morning coffee or evening gatherings, allowing you to soak in the tranquil surroundings. The driveway accommodates four or more vehicles, ensuring convenience for you and your guests. Imagine evenings spent enjoying the gentle sounds of nature, or hosting barbecues on the deck. This home is not just a place to live it's where memories are made. Embrace the lifestyle you've always wanted in this delightful property that beautifully blends comfort with the allure of outdoor living. Updated Kitchen Cabinets and appliances. Fresh painting throughout and new carpeting in primary bedroom.

This charming ranch-style home, built in 1978, offers a serene retreat on a spacious 0.33-acre lot, perfect for those who appreciate the beauty of nature. With three cozy bedrooms and two full bathrooms, this residence is designed for comfort and ease. The inviting screened porch and deck provide ideal spaces for morning coffee or evening gatherings, allowing you to soak in the tranquil surroundings. The driveway accommodates four or more vehicles, ensuring convenience for you and your guests. Imagine evenings spent enjoying the gentle sounds of nature, or hosting barbecues on the deck. This home is not just a place to live it's where memories are made. Embrace the lifestyle you've always wanted in this delightful property that beautifully blends comfort with the allure of outdoor living. Updated Kitchen Cabinets and appliances. Fresh painting throughout and new carpeting in primary bedroom.

206 Penny Ln, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

$729,900

**Chesapeake Bay views, nearly new construction, and an opportunity to turn your coastal getaway into a potential income-producing investment!** Welcome to 335 South Carolina Road in Stevensville, where modern comfort meets the laid-back lifestyle of Maryland's Eastern Shore. Offering 4 bedrooms, 3.5 bathrooms, multiple living spaces, and THREE decks - 2 with expansive views of the Chesapeake Bay, this nearly new home delivers the perfect combination of space, comfort, and coastal charm. Step inside to discover luxury vinyl plank flooring throughout the main living areas and a beautifully appointed kitchen featuring quartz countertops, a spacious island with seating and additional storage, and plenty of room for gathering and entertaining. Multiple living spaces provide flexibility for relaxing, hosting overnight guests, working from home, or accommodating extended stays. But the real magic happens outside! Imagine starting your mornings with coffee overlooking the Chesapeake Bay, spending afternoons at the community beach, and ending your evenings gathered around the fire pit beneath the stars. With three decks, a spacious yard, and a storage shed, there's plenty of room to enjoy the outdoors and embrace the waterfront lifestyle. **Looking for a home that could work for you even when you're not there?** With its desirable Chesapeake Bay setting, generous accommodations, multiple outdoor entertaining areas, and access to the community beach, this property presents an exciting opportunity for buyers interested in exploring short-term rental income through platforms such as Airbnb or VRBO, subject to applicable regulations and approvals. Whether you're searching for a year-round residence, a weekend escape, a second home with potential rental income, or an investment opportunity, 335 South Carolina Road offers the flexibility to make your Eastern Shore dreams a reality. **Why just dream about life at the Bay when you could be living it—and potentially earning income from it, too?**Short-term rental use and income potential are subject to buyer verification of all applicable county regulations, licensing requirements, and community restrictions.

**Chesapeake Bay views, nearly new construction, and an opportunity to turn your coastal getaway into a potential income-producing investment!** Welcome to 335 South Carolina Road in Stevensville, where modern comfort meets the laid-back lifestyle of Maryland's Eastern Shore. Offering 4 bedrooms, 3.5 bathrooms, multiple living spaces, and THREE decks - 2 with expansive views of the Chesapeake Bay, this nearly new home delivers the perfect combination of space, comfort, and coastal charm. Step inside to discover luxury vinyl plank flooring throughout the main living areas and a beautifully appointed kitchen featuring quartz countertops, a spacious island with seating and additional storage, and plenty of room for gathering and entertaining. Multiple living spaces provide flexibility for relaxing, hosting overnight guests, working from home, or accommodating extended stays. But the real magic happens outside! Imagine starting your mornings with coffee overlooking the Chesapeake Bay, spending afternoons at the community beach, and ending your evenings gathered around the fire pit beneath the stars. With three decks, a spacious yard, and a storage shed, there's plenty of room to enjoy the outdoors and embrace the waterfront lifestyle. **Looking for a home that could work for you even when you're not there?** With its desirable Chesapeake Bay setting, generous accommodations, multiple outdoor entertaining areas, and access to the community beach, this property presents an exciting opportunity for buyers interested in exploring short-term rental income through platforms such as Airbnb or VRBO, subject to applicable regulations and approvals. Whether you're searching for a year-round residence, a weekend escape, a second home with potential rental income, or an investment opportunity, 335 South Carolina Road offers the flexibility to make your Eastern Shore dreams a reality. **Why just dream about life at the Bay when you could be living it—and potentially earning income from it, too?**Short-term rental use and income potential are subject to buyer verification of all applicable county regulations, licensing requirements, and community restrictions.

335 S Carolina Rd, Stevensville

Listing courtesy of Samson Properties. Contact:

$199,900

Attention Investors, Renovators, and Buyers Looking for Opportunity! Discover the potential of 406 Dominion Road in Chester, Maryland, situated in Queen Anne's County on desirable Kent Island. This property is being sold strictly AS-IS, presenting an opportunity for investors, contractors, and buyers looking to renovate, restore, or customize a home to their vision. Conveniently located near shopping, dining, recreational opportunities, and major commuter routes, including US Route 50/301, providing access to Annapolis. The property is its present AS-IS condition. The seller will make no repairs or improvements. Bring your contractor, your renovation plans, and your imagination to explore the possibilities this Kent Island property has to offer.

Attention Investors, Renovators, and Buyers Looking for Opportunity! Discover the potential of 406 Dominion Road in Chester, Maryland, situated in Queen Anne's County on desirable Kent Island. This property is being sold strictly AS-IS, presenting an opportunity for investors, contractors, and buyers looking to renovate, restore, or customize a home to their vision. Conveniently located near shopping, dining, recreational opportunities, and major commuter routes, including US Route 50/301, providing access to Annapolis. The property is its present AS-IS condition. The seller will make no repairs or improvements. Bring your contractor, your renovation plans, and your imagination to explore the possibilities this Kent Island property has to offer.

406 Dominion Rd, Chester

Listing courtesy of Sell Your Home Services. Contact:

$1,650,000

Set in a wonderfully private waterfront setting, this elegant traditional home combines timeless charm with impressive renovations and thoughtful modern updates. Offering five bedrooms, the home features a spacious first-floor primary suite with an updated bath and walk-in shower, along with a second-floor waterside bedroom suite. Beautiful hard wood floors flow throughout much of the home, complementing the generously sized rooms and creating an inviting atmosphere for both everyday living and entertainment. The fully renovated kitchen is a standout, featuring upscale appliances, a granite-topped center island, and a striking tile backsplash extending to the ceiling. Formal living and dining rooms, along with a classic library, offer elegant spaces for entertaining, relaxing, and working from home. At the heart of the home, an expansive addition featuring a family room and game room provides exceptional space for gatherings, celebrations, and relaxed waterfront living. Bamboo flooring and vaulted ceilings enhance the bright, open feel of this welcoming retreat. The waterfront setting is truly special, offering privacy, access to the bay, a completely replaced of dock, and a 10,000-pound boat lift. Water depth is approximately four to six feet at medium-low tide. Additional improvements include a painted brick exterior, and an architectural-shingle roof installed just three years ago. A detached, oversized two-car garage with a second floor provides abundant storage and exciting possibilities for a variety of uses. The swimming pool is being sold in as-is condition. Combining classic elegance, extensive living spaces, significant updates, and exceptional waterfront amenities, this distinctive property offers a wonderful opportunity to embrace the privacy and beauty of waterfront living.

5 Beds ⋅ 4 Baths

Set in a wonderfully private waterfront setting, this elegant traditional home combines timeless charm with impressive renovations and thoughtful modern updates. Offering five bedrooms, the home features a spacious first-floor primary suite with an updated bath and walk-in shower, along with a second-floor waterside bedroom suite. Beautiful hard wood floors flow throughout much of the home, complementing the generously sized rooms and creating an inviting atmosphere for both everyday living and entertainment. The fully renovated kitchen is a standout, featuring upscale appliances, a granite-topped center island, and a striking tile backsplash extending to the ceiling. Formal living and dining rooms, along with a classic library, offer elegant spaces for entertaining, relaxing, and working from home. At the heart of the home, an expansive addition featuring a family room and game room provides exceptional space for gatherings, celebrations, and relaxed waterfront living. Bamboo flooring and vaulted ceilings enhance the bright, open feel of this welcoming retreat. The waterfront setting is truly special, offering privacy, access to the bay, a completely replaced of dock, and a 10,000-pound boat lift. Water depth is approximately four to six feet at medium-low tide. Additional improvements include a painted brick exterior, and an architectural-shingle roof installed just three years ago. A detached, oversized two-car garage with a second floor provides abundant storage and exciting possibilities for a variety of uses. The swimming pool is being sold in as-is condition. Combining classic elegance, extensive living spaces, significant updates, and exceptional waterfront amenities, this distinctive property offers a wonderful opportunity to embrace the privacy and beauty of waterfront living.

312 Greenwood Point Rd, Grasonville

Listing courtesy of Coldwell Banker Realty. Contact:

$280,000

Welcome to 411 Merganser Court, a charming 2-bedroom, 2-bath condo in the sought-after Bayside community. This well-maintained home features a cozy gas fireplace, hardwood floors, newer carpet in bedrooms, an updated water heater within the last year and offers the perfect opportunity to enjoy the Eastern Shore lifestyle at an affordable price.Come and check out what this condo has to offer! Enjoy resort-style amenities including a community pool, tennis courts, and more, all just steps from your door. Plus, you're within walking distance to local marinas, waterfront restaurants, shopping, and entertainment. Whether you're looking for a year-round residence, weekend getaway, or low-maintenance living, this Bayside gem is ready for you!

2 Beds ⋅ 2 Baths

Welcome to 411 Merganser Court, a charming 2-bedroom, 2-bath condo in the sought-after Bayside community. This well-maintained home features a cozy gas fireplace, hardwood floors, newer carpet in bedrooms, an updated water heater within the last year and offers the perfect opportunity to enjoy the Eastern Shore lifestyle at an affordable price.Come and check out what this condo has to offer! Enjoy resort-style amenities including a community pool, tennis courts, and more, all just steps from your door. Plus, you're within walking distance to local marinas, waterfront restaurants, shopping, and entertainment. Whether you're looking for a year-round residence, weekend getaway, or low-maintenance living, this Bayside gem is ready for you!

411 Merganser Ct, Chester

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

$396,900

Beautifully and professionally renovated, this charming ranch-style home combines modern updates with the comfort and functionality of a traditional floor plan. Offering 3 bedrooms and 2 full baths, including a private ensuite bath in the primary bedroom, this move-in-ready home has been thoughtfully redesigned . The bright, sunny kitchen features abundant cabinet space, brand-new appliances, and luxury vinyl plank flooring. A sliding glass door opens to a spacious deck overlooking a lovely backyard with mature trees and backs to woods, creating the perfect setting for outdoor entertaining or quiet relaxation.The generous living room showcases beautifully refinished red oak hardwood floors that continue throughout all three bedrooms, adding warmth and timeless appeal. Both bathrooms have been completely renovated with new showers, vanities, sinks, toilets, and luxury vinyl plank flooring.For added peace of mind, major upgrades include a new HVAC system, PEX water lines, recessed lighting throughout, a new hot water heater, water softener, and well pump, all conveniently located in a heated mechanical room. Located in the established Harbor View community, this exceptional home is just minutes from shopping, urgent care, walking trails, and Resturants. Convenient to the Kent Narrows and Bay Bridge. Offering the perfect blend of modern convenience and Eastern Shore charm, 1837 Harbor Drive is truly better than new. Come discover a place you'll be proud to call home and enjoy everything the Eastern Shore lifestyle has to offer. See Floor Plan and Renovations to 1837 Harbor Dr in Documents.

Beautifully and professionally renovated, this charming ranch-style home combines modern updates with the comfort and functionality of a traditional floor plan. Offering 3 bedrooms and 2 full baths, including a private ensuite bath in the primary bedroom, this move-in-ready home has been thoughtfully redesigned . The bright, sunny kitchen features abundant cabinet space, brand-new appliances, and luxury vinyl plank flooring. A sliding glass door opens to a spacious deck overlooking a lovely backyard with mature trees and backs to woods, creating the perfect setting for outdoor entertaining or quiet relaxation.The generous living room showcases beautifully refinished red oak hardwood floors that continue throughout all three bedrooms, adding warmth and timeless appeal. Both bathrooms have been completely renovated with new showers, vanities, sinks, toilets, and luxury vinyl plank flooring.For added peace of mind, major upgrades include a new HVAC system, PEX water lines, recessed lighting throughout, a new hot water heater, water softener, and well pump, all conveniently located in a heated mechanical room. Located in the established Harbor View community, this exceptional home is just minutes from shopping, urgent care, walking trails, and Resturants. Convenient to the Kent Narrows and Bay Bridge. Offering the perfect blend of modern convenience and Eastern Shore charm, 1837 Harbor Drive is truly better than new. Come discover a place you'll be proud to call home and enjoy everything the Eastern Shore lifestyle has to offer. See Floor Plan and Renovations to 1837 Harbor Dr in Documents.

1837 Harbor, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

$589,900

Welcome to 305 N Brook Drive, where beautiful upgrades, thoughtful details, and a premium wooded setting come together in one of North Brook's most desirable locations! Situated on just under half an acre and backing to the woods, this exceptional home offers the perfect combination of privacy, space, and elevated living. Step inside to discover rich chocolate-toned, 5¼-inch wide plank engineered hardwood flooring throughout the main level, custom moldings, plantation shutters, and upgraded lighting and fixtures. The stunning white kitchen features premium Cambria quartz countertops, a subway tile backsplash, and stylish finishes that bring both elegance and functionality to the heart of the home. Upstairs, you'll find three spacious bedrooms, including a beautiful primary suite featuring a walk-in closet and double sink vanity. The outdoor living space is equally impressive! Enjoy relaxing evenings on the expansive 600 sqft paver patio featuring a gas fire pit. The fenced in yard, peaceful wooded backdrop, and storage shed add even more to this incredible property. The fully finished basement, completed in 2024, offers additional living space, a fourth bedroom, a full bathroom with a walk-in shower, and extra storage. A whole home water softener was also installed, providing added comfort and convenience. With its premium lot, extensive upgrades, and incredible indoor and outdoor living spaces, 305 N Brook Drive truly stands apart. Opportunities like this in North Brook don't come along often. Come experience everything this beautiful home has to offer!

Welcome to 305 N Brook Drive, where beautiful upgrades, thoughtful details, and a premium wooded setting come together in one of North Brook's most desirable locations! Situated on just under half an acre and backing to the woods, this exceptional home offers the perfect combination of privacy, space, and elevated living. Step inside to discover rich chocolate-toned, 5¼-inch wide plank engineered hardwood flooring throughout the main level, custom moldings, plantation shutters, and upgraded lighting and fixtures. The stunning white kitchen features premium Cambria quartz countertops, a subway tile backsplash, and stylish finishes that bring both elegance and functionality to the heart of the home. Upstairs, you'll find three spacious bedrooms, including a beautiful primary suite featuring a walk-in closet and double sink vanity. The outdoor living space is equally impressive! Enjoy relaxing evenings on the expansive 600 sqft paver patio featuring a gas fire pit. The fenced in yard, peaceful wooded backdrop, and storage shed add even more to this incredible property. The fully finished basement, completed in 2024, offers additional living space, a fourth bedroom, a full bathroom with a walk-in shower, and extra storage. A whole home water softener was also installed, providing added comfort and convenience. With its premium lot, extensive upgrades, and incredible indoor and outdoor living spaces, 305 N Brook Drive truly stands apart. Opportunities like this in North Brook don't come along often. Come experience everything this beautiful home has to offer!

305 N Brook Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact:

$559,900

Come discover Eastern Shore living in the sought-after Waterfront Community of Gibson's Grant! Tucked away on a peaceful cul-de-sac, this charming end-of-row townhouse offers 3 spacious Bedrooms, 2.5 Bathrooms, Office/Den and an inviting blend of comfort and refined style! Stunning Hardwood floors, extensive Crown Moldings and recessed lighting set an elegant tone throughout. The Gourmet Kitchen features upgraded Granite countertops, NEW Stainless Steel Refrigerator, Cooktop, Double Oven, 42"Cabinets and a generous Granite Island... opening seamlessly to the Family Room for effortless entertaining! A Fireplace creates a cozy gathering place, while the Primary Suite provides a private retreat with a walk-in closet and luxurious en-suite Bath. New washer and dryer in the laundry room and brand new carpet in 2 bedrooms and stairs. Two car garage for extra storage and a driveway for off street parking, makes life easier. Outside boasts an extensive brick patio which provides an attractive setting for alfresco dining, grilling and relaxation. The association handles lawn care and maintenance, leaving more time to enjoy Gibson's Grant's exceptional amenities, including a Clubhouse, Pool, Fitness Room, Fishing/Crabbing Pier, Pavilion, Trails, Kayak Storage and Playground! Convenient access to Macum Creek for canoeing and kayaking, plus nearby parks, beaches, boat ramps, boutique shopping, restaurants, outlets and highly regarded schools! This home delivers the ideal combination of water-oriented recreation, low-maintenance living and neighborhood charm!

Come discover Eastern Shore living in the sought-after Waterfront Community of Gibson's Grant! Tucked away on a peaceful cul-de-sac, this charming end-of-row townhouse offers 3 spacious Bedrooms, 2.5 Bathrooms, Office/Den and an inviting blend of comfort and refined style! Stunning Hardwood floors, extensive Crown Moldings and recessed lighting set an elegant tone throughout. The Gourmet Kitchen features upgraded Granite countertops, NEW Stainless Steel Refrigerator, Cooktop, Double Oven, 42"Cabinets and a generous Granite Island... opening seamlessly to the Family Room for effortless entertaining! A Fireplace creates a cozy gathering place, while the Primary Suite provides a private retreat with a walk-in closet and luxurious en-suite Bath. New washer and dryer in the laundry room and brand new carpet in 2 bedrooms and stairs. Two car garage for extra storage and a driveway for off street parking, makes life easier. Outside boasts an extensive brick patio which provides an attractive setting for alfresco dining, grilling and relaxation. The association handles lawn care and maintenance, leaving more time to enjoy Gibson's Grant's exceptional amenities, including a Clubhouse, Pool, Fitness Room, Fishing/Crabbing Pier, Pavilion, Trails, Kayak Storage and Playground! Convenient access to Macum Creek for canoeing and kayaking, plus nearby parks, beaches, boat ramps, boutique shopping, restaurants, outlets and highly regarded schools! This home delivers the ideal combination of water-oriented recreation, low-maintenance living and neighborhood charm!

227 Gibson Cir, Chester

Listing courtesy of RE/MAX Executive. Contact:

$699,000

Harbor View - This beautiful waterfront home has been completely remodeled in 2026, new siding, new kitchen, new bathrooms, new luxury vinyl flooring. Freshly painted and in move in ready condition.

Harbor View - This beautiful waterfront home has been completely remodeled in 2026, new siding, new kitchen, new bathrooms, new luxury vinyl flooring. Freshly painted and in move in ready condition.

2627 Cecil Dr, Chester

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

111 Beach Harbor Dr Unit 85 A, Grasonville

$129,200

Site contains a 2011 DutchPark tiny home style RV with an attached 200sqft sunroom. 2 decks, 8x8 shed, patio, deep shaded lot. The RV is 40ft long, with 2 large bump outs and has cathedral ceilings, a shingle roof and house type siding. Heating is propane forced air and central air conditioning. Has 1 queen br and Sleeps 6 with 2 queen size sleeper sofas. Located in Beach Harbor in Grasonville MD. Membership provides amenities including Clubhouse, Bathhouse, Swimming Pool and Hot Tub, Playground, Multipurpose courts, Boat Launch and Beach. Season runs March 15th through first Monday following Thanksgiving. Limited access during the off season.

1 Beds ⋅ 1 Baths

Site contains a 2011 DutchPark tiny home style RV with an attached 200sqft sunroom. 2 decks, 8x8 shed, patio, deep shaded lot. The RV is 40ft long, with 2 large bump outs and has cathedral ceilings, a shingle roof and house type siding. Heating is propane forced air and central air conditioning. Has 1 queen br and Sleeps 6 with 2 queen size sleeper sofas. Located in Beach Harbor in Grasonville MD. Membership provides amenities including Clubhouse, Bathhouse, Swimming Pool and Hot Tub, Playground, Multipurpose courts, Boat Launch and Beach. Season runs March 15th through first Monday following Thanksgiving. Limited access during the off season.

111 Beach Harbor Dr Unit 85 A, Grasonville

Listing courtesy of Century 21 Downtown. Contact:

$659,900

Ready to live your best “Shore Life”? Morning coffee on the screened porch, an afternoon out on Cox Creek, and evenings spent relaxing with friends—this is the kind of lifestyle that makes coming home to Kent Island so special. Located in charming Cox Creek Landing, this beautiful Colonial offers 4 spacious bedrooms, 2.5 baths, and inviting spaces to gather, unwind, and enjoy life both indoors and out. A cozy fireplace makes the living room a favorite spot on cooler evenings, while the deck and large screened porch with vaulted ceilings set the scene for summer dinners, lazy weekends, and lingering conversations. A beautifully landscaped yard and attached garage round out the package. Here, the water is part of everyday life. Head to the private community pier to fish, launch your kayak for a peaceful paddle, or spend the day exploring by boat. A separately deeded boat slip with a lift is also available for purchase at an additional cost—making it even easier to turn your boating plans into a regular routine. With maintained common grounds and a welcoming neighborhood setting, Cox Creek Landing brings together the comforts of home and the outdoor adventures that make Eastern Shore living so appealing. Come for the house… stay for the Shore Life.

4 Beds ⋅ 3 Baths

Ready to live your best “Shore Life”? Morning coffee on the screened porch, an afternoon out on Cox Creek, and evenings spent relaxing with friends—this is the kind of lifestyle that makes coming home to Kent Island so special. Located in charming Cox Creek Landing, this beautiful Colonial offers 4 spacious bedrooms, 2.5 baths, and inviting spaces to gather, unwind, and enjoy life both indoors and out. A cozy fireplace makes the living room a favorite spot on cooler evenings, while the deck and large screened porch with vaulted ceilings set the scene for summer dinners, lazy weekends, and lingering conversations. A beautifully landscaped yard and attached garage round out the package. Here, the water is part of everyday life. Head to the private community pier to fish, launch your kayak for a peaceful paddle, or spend the day exploring by boat. A separately deeded boat slip with a lift is also available for purchase at an additional cost—making it even easier to turn your boating plans into a regular routine. With maintained common grounds and a welcoming neighborhood setting, Cox Creek Landing brings together the comforts of home and the outdoor adventures that make Eastern Shore living so appealing. Come for the house… stay for the Shore Life.

220 Creeks End Ln, Stevensville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

$749,000

Friday, 5 o’clock. The week falls away the moment you turn down the lane. Sunlight flickers through the trees. The Chester glints on your left. Then the woods open up, the cottage comes into view, and there’s water on your right too. You’ve arrived at a point embraced by about 2,000 feet of tidal shoreline on 13.42 quiet, private acres. This 1950 Tidewater Cape was built by a father and son as a summer escape, and you can feel the years of happy weekends the moment you step inside. Warm hardwood floors underfoot. Built-ins crafted by hand. Exposed beams overhead and a fireplace waiting for cool autumn evenings. One bedroom, two full baths, and a lower level country kitchen and family room where the coffee pot is always on, and the table always has room for one more. Walk around back, and the house shows you its heart: three stories of classic Tidewater charm rising above the river, glowing in the late afternoon light. Saturday starts slow, with coffee on the porch and mist lifting off the water. The afternoon belongs to fishing, paddling, or wandering the woods. Evening brings the sunset, painting the river gold from the lower patio. And Sunday? Sunday comes far too soon. A detached garage and a workshop with electric stand ready for the kayaks, the fishing rods, and the weekend projects. The pier conveys as is and is ready for your vision. Some places you visit. This one you’ll count the days to come back to.

1 Beds ⋅ 1 Baths

Friday, 5 o’clock. The week falls away the moment you turn down the lane. Sunlight flickers through the trees. The Chester glints on your left. Then the woods open up, the cottage comes into view, and there’s water on your right too. You’ve arrived at a point embraced by about 2,000 feet of tidal shoreline on 13.42 quiet, private acres. This 1950 Tidewater Cape was built by a father and son as a summer escape, and you can feel the years of happy weekends the moment you step inside. Warm hardwood floors underfoot. Built-ins crafted by hand. Exposed beams overhead and a fireplace waiting for cool autumn evenings. One bedroom, two full baths, and a lower level country kitchen and family room where the coffee pot is always on, and the table always has room for one more. Walk around back, and the house shows you its heart: three stories of classic Tidewater charm rising above the river, glowing in the late afternoon light. Saturday starts slow, with coffee on the porch and mist lifting off the water. The afternoon belongs to fishing, paddling, or wandering the woods. Evening brings the sunset, painting the river gold from the lower patio. And Sunday? Sunday comes far too soon. A detached garage and a workshop with electric stand ready for the kayaks, the fishing rods, and the weekend projects. The pier conveys as is and is ready for your vision. Some places you visit. This one you’ll count the days to come back to.

200 Powers Ln, Millington

Listing courtesy of Keller Williams Select Realtors of Easton. Contact:

$1,895,000

Exceptional Waterfront Living in Queenstown, tucked away minutes off Route 50. Discover the perfect blend of luxury, privacy, and waterfront living at 100 Bryans Channel Way. Situated on nearly 3 acres with almost 300 feet of water frontage, this remarkable property offers an extraordinary Eastern Shore lifestyle with no HOA and just minutes from Routes 50 and 301. A circular driveway welcomes you to the residence, featuring a cedar shake roof, attached two-car garage, detached 3-car garage and thoughtfully designed living spaces. At the heart of the home, a stunning new gourmet kitchen showcases a six-burner range, double ovens, two dishwashers, pot filler, custom spice cabinets, and an oversized island with abundant storage. A spacious pantry and adjoining secondary kitchen/butler's pantry offer an additional oven, sink, freezer, and stacked washer and dryer. Waterfront dining and living rooms capture beautiful views, while an additional sitting room off the kitchen provides a comfortable space to relax or gather. Upstairs, two bedrooms share a full bathroom, complemented by additional attic storage and unfinished space offering the potential for another bedroom with a spacious walk-in closet. Outside, your private waterfront retreat awaits. An expansive deck with gazebo overlooks the water, while a saltwater pool with waterfall and surrounding paver patio creates an idyllic setting for entertaining. Boating enthusiasts will appreciate the private pier featuring two boat lifts and a dedicated jet ski lift. Adding exceptional versatility is a detached 30' x 40' garage with approximately 1,200 square feet of additional conditioned storage space above, offering ample room for seasonal items, recreational equipment, and more. The grounds also feature apple, peach, and pear trees, a storage shed, and fencing along the sides of the property. With nearly 3 acres of waterfront privacy, extraordinary amenities, this distinctive property offers a rare opportunity to experience the best of Maryland's Eastern Shore, with convenient access to Annapolis, the Bay Bridge, and beyond. Located in the private waterfront community of Wye Harbor with NO HOA or covenants and only twenty eight homes. Welcome home!

Exceptional Waterfront Living in Queenstown, tucked away minutes off Route 50. Discover the perfect blend of luxury, privacy, and waterfront living at 100 Bryans Channel Way. Situated on nearly 3 acres with almost 300 feet of water frontage, this remarkable property offers an extraordinary Eastern Shore lifestyle with no HOA and just minutes from Routes 50 and 301. A circular driveway welcomes you to the residence, featuring a cedar shake roof, attached two-car garage, detached 3-car garage and thoughtfully designed living spaces. At the heart of the home, a stunning new gourmet kitchen showcases a six-burner range, double ovens, two dishwashers, pot filler, custom spice cabinets, and an oversized island with abundant storage. A spacious pantry and adjoining secondary kitchen/butler's pantry offer an additional oven, sink, freezer, and stacked washer and dryer. Waterfront dining and living rooms capture beautiful views, while an additional sitting room off the kitchen provides a comfortable space to relax or gather. Upstairs, two bedrooms share a full bathroom, complemented by additional attic storage and unfinished space offering the potential for another bedroom with a spacious walk-in closet. Outside, your private waterfront retreat awaits. An expansive deck with gazebo overlooks the water, while a saltwater pool with waterfall and surrounding paver patio creates an idyllic setting for entertaining. Boating enthusiasts will appreciate the private pier featuring two boat lifts and a dedicated jet ski lift. Adding exceptional versatility is a detached 30' x 40' garage with approximately 1,200 square feet of additional conditioned storage space above, offering ample room for seasonal items, recreational equipment, and more. The grounds also feature apple, peach, and pear trees, a storage shed, and fencing along the sides of the property. With nearly 3 acres of waterfront privacy, extraordinary amenities, this distinctive property offers a rare opportunity to experience the best of Maryland's Eastern Shore, with convenient access to Annapolis, the Bay Bridge, and beyond. Located in the private waterfront community of Wye Harbor with NO HOA or covenants and only twenty eight homes. Welcome home!

100 Bryans Channel Way, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

$699,000

Step into a piece of Centreville's history with this distinctive Victorian, originally built in 1875, where timeless architectural charm meets thoughtful modern updates! Situated on approximately half an acre in the heart of town, this one-of-a-kind property welcomes you with a massive wraparound front porch and charming porch swing, the perfect place to relax and take in the beauty of your surroundings. Inside, you'll find impressive 10-foot ceilings on the main level, classic built-ins, beautiful wood floors, and character-filled spaces that reflect the home's historic roots. Offering 4 bedrooms, 3 full baths, and 1 half bath, plus a massive bonus room with the potential for a 5th bedroom, there is plenty of space to accommodate a variety of needs and lifestyles. This home blends its historic character with extensive improvements made over the years. The galley kitchen was fully renovated in 2024 with new cabinetry, countertops, flooring, and appliances, including a gas range, followed by a substantial kitchen expansion in 2025 that added a 12x12 breakfast nook, additional cabinetry and countertops, a second sink and refrigerator, and a wine cooler. A full bathroom on the main level was also part of the expansion, including tile flooring & radiant floor heat. Additionally, the primary bathroom on the second floor was renovated with a full-size tiled shower, new vanity, and toilet, with additional bathroom upgrades enhancing the secondary bathroom as well. Important system updates include a new high-efficiency furnace/boiler, mini-split systems serving all three second-floor bedrooms and the primary bathroom, removal of the original knob-and-tube wiring, a metal chimney liner, and replacement of the second-floor windows. The chimneys have been converted to gas logs, offering the ambiance of a fire with added convenience, while still keeping the character of the stunning fireplaces. Additional improvements include refinished wood floors, updated third-floor flooring and carpeting, and numerous other enhancements. A full list of improvements is available. Step outside and discover an enchanting setting with extensive, lush landscaping reminiscent of finding yourself strolling through a peaceful English garden, creating a beautiful backdrop for relaxing and entertaining. The fully fenced in-ground concrete, saltwater pool, less than four years old, provides a wonderful place to enjoy warm summer days, while the hardscape walkway connects the outdoor spaces. A distinctive carriage house, originally dating to 1906 and thoughtfully modified with a more modern feel, adds even more character and versatility. Featuring two garage doors with openers and a wide staircase leading to the second floor, this separate structure offers valuable garage and additional space. And the location? It's hard to beat! Enjoy a short walk to the Wharf, Doc's, and the heart of downtown Centreville, where local destinations and small-town charm are right outside your door. Historic character, extensive updates, enchanting gardens, a new pool, and a unique carriage house come together to create a truly special Eastern Shore property unlike anything else on the market! **More Photos & Video Coming Soon!**

Step into a piece of Centreville's history with this distinctive Victorian, originally built in 1875, where timeless architectural charm meets thoughtful modern updates! Situated on approximately half an acre in the heart of town, this one-of-a-kind property welcomes you with a massive wraparound front porch and charming porch swing, the perfect place to relax and take in the beauty of your surroundings. Inside, you'll find impressive 10-foot ceilings on the main level, classic built-ins, beautiful wood floors, and character-filled spaces that reflect the home's historic roots. Offering 4 bedrooms, 3 full baths, and 1 half bath, plus a massive bonus room with the potential for a 5th bedroom, there is plenty of space to accommodate a variety of needs and lifestyles. This home blends its historic character with extensive improvements made over the years. The galley kitchen was fully renovated in 2024 with new cabinetry, countertops, flooring, and appliances, including a gas range, followed by a substantial kitchen expansion in 2025 that added a 12x12 breakfast nook, additional cabinetry and countertops, a second sink and refrigerator, and a wine cooler. A full bathroom on the main level was also part of the expansion, including tile flooring & radiant floor heat. Additionally, the primary bathroom on the second floor was renovated with a full-size tiled shower, new vanity, and toilet, with additional bathroom upgrades enhancing the secondary bathroom as well. Important system updates include a new high-efficiency furnace/boiler, mini-split systems serving all three second-floor bedrooms and the primary bathroom, removal of the original knob-and-tube wiring, a metal chimney liner, and replacement of the second-floor windows. The chimneys have been converted to gas logs, offering the ambiance of a fire with added convenience, while still keeping the character of the stunning fireplaces. Additional improvements include refinished wood floors, updated third-floor flooring and carpeting, and numerous other enhancements. A full list of improvements is available. Step outside and discover an enchanting setting with extensive, lush landscaping reminiscent of finding yourself strolling through a peaceful English garden, creating a beautiful backdrop for relaxing and entertaining. The fully fenced in-ground concrete, saltwater pool, less than four years old, provides a wonderful place to enjoy warm summer days, while the hardscape walkway connects the outdoor spaces. A distinctive carriage house, originally dating to 1906 and thoughtfully modified with a more modern feel, adds even more character and versatility. Featuring two garage doors with openers and a wide staircase leading to the second floor, this separate structure offers valuable garage and additional space. And the location? It's hard to beat! Enjoy a short walk to the Wharf, Doc's, and the heart of downtown Centreville, where local destinations and small-town charm are right outside your door. Historic character, extensive updates, enchanting gardens, a new pool, and a unique carriage house come together to create a truly special Eastern Shore property unlike anything else on the market! **More Photos & Video Coming Soon!**

403 Chesterfield Ave, Centreville

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

$549,999

Enjoy the relaxed charm of Kent Island living at 216 Mainsail Drive in Stevensville! This inviting home offers comfortable one-level living with three bedrooms and two full bathrooms, including a primary bedroom with its own ensuite bath. A standout feature is the screened three-season room, an inviting spot to enjoy your morning coffee, unwind with a good book, or simply relax. Water views from the kitchen and a secondary bedroom add a special touch to the home's appeal. Recent improvements include a new roof and new windows, both completed in 2026. Inside, a gas fireplace adds warmth and character, while the fenced backyard, mature landscaping, and storage shed offer additional outdoor enjoyment and storage. The garage also features a ceiling-mounted retractable reel, an added convenience for hobbyists and DIY enthusiasts. Located in the Anchorage community, this property offers the opportunity to enjoy the Kent Island lifestyle, with community amenities and convenient access to local shopping, dining, and commuter routes. Come discover the possibilities and make this home your own!

Enjoy the relaxed charm of Kent Island living at 216 Mainsail Drive in Stevensville! This inviting home offers comfortable one-level living with three bedrooms and two full bathrooms, including a primary bedroom with its own ensuite bath. A standout feature is the screened three-season room, an inviting spot to enjoy your morning coffee, unwind with a good book, or simply relax. Water views from the kitchen and a secondary bedroom add a special touch to the home's appeal. Recent improvements include a new roof and new windows, both completed in 2026. Inside, a gas fireplace adds warmth and character, while the fenced backyard, mature landscaping, and storage shed offer additional outdoor enjoyment and storage. The garage also features a ceiling-mounted retractable reel, an added convenience for hobbyists and DIY enthusiasts. Located in the Anchorage community, this property offers the opportunity to enjoy the Kent Island lifestyle, with community amenities and convenient access to local shopping, dining, and commuter routes. Come discover the possibilities and make this home your own!

216 Mainsail Dr, Stevensville

Listing courtesy of Patterson-Schwartz-Newark. Contact:

$599,000

Don't miss this home in the Symphony Village at Centreville Active Adult Community. This home has so much to offer, starting with owned solar panels (please ask about extremely low electricity bills) and a battery backup system that both convey with the home. With a perfect blend of luxury and comfort, this home is designed to cater to your every need while providing a warm and inviting atmosphere. Spanning 2,684 square feet, this traditional-style detached home boasts three spacious bedrooms and three full bathrooms, ensuring ample space for relaxation and entertaining. The interior features are nothing short of spectacular, showcasing a gourmet kitchen equipped with high-end stainless steel appliances, including a built-in microwave, wall oven, and cooktop and upgraded counters. The elegant formal dining room provide the perfect backdrop for memorable meals, while the recessed lighting add a touch of sophistication throughout. The main living area featuring a built in serving bar with beverage cooler and wine cooler along with bar stools allow for a great space for entertaining and socializing. The master suite with his and her walk-in closets and the master bath are designed to enhance the primary resident's comfort. Enjoy the convenience of a main floor laundry. Also conveying with this home is a fitness room including a Peloton Bike and Treadmill. The upper level of this Gershwin model home features a gaming area including custom built pool table, foosball table, television and sleep sofa that all convey with the home. The third bedroom and third full bath are also located on the upper level. This home includes a dual zone HVAC system. Step outside to discover the meticulously landscaped exterior, featuring extensive hardscaping and underground lawn sprinklers that enhance the curb appeal. The piano shaped paver patio includes the patio furniture, propane connected grill and patio heater for the new owners enjoyment and relaxation. The attached two car garages features a hard-wired 64 amp high speed level 2 EV charger by Lucid that can charge vehicles that have a J1772 connector or with an adapter NACS (Tesla) style charging port. The community amenities are truly exceptional, including both indoor and outdoor pools, a fitness center, and a variety of recreational options such as pickleball courts, tennis courts, and walking paths. The clubhouse and bar/lounge offer perfect venues for socializing and relaxation. The community's association fee covers common area maintenance, lawn care, and snow removal, allowing you to enjoy a carefree lifestyle. Experience the exclusive lifestyle that Symphony Village at Centreville offers, where luxury meets comfort in a vibrant community designed for your enjoyment. This is more than just a home; it's a sanctuary where you can create lasting memories and embrace a fulfilling life. This home also includes a Cinch Home Warranty to cover the buyers for 1 year after settlement.