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117 River Run, Queenstown
$1,300,000
4 Beds ⋅ 3 Baths
Wye River Waterfront Living at Its Best! If you love boating, fishing, crabbing, and being on the water, this Cape Cod-style home on the Wye River may be just what you have been waiting for. Situated on 1.46 private acres with more than 250 feet of waterfront, this property offers a peaceful setting surrounded by mature trees, beautiful landscaping, and plenty of privacy. The Wye River is well known for its excellent boating, fishing, and crabbing, along with its deep water that makes it especially appealing to boaters. Whether you are looking for a full-time residence, a second home, or an investment opportunity, this property offers tremendous possibilities. Enjoy the outdoors from the private screened porch, the perfect place to relax, entertain, and take in the peaceful surroundings. Inside, the home offers four bedrooms and two and a half baths, with generously sized rooms throughout. The first-floor primary suite provides the convenience of one-level living and makes the home well suited for those looking to remain in the home long term. Upstairs are three spacious bedrooms and a full bath, providing plenty of room for family and guests. The light-filled family room features a beautiful fireplace and offers a comfortable space for both relaxing and entertaining. A separate game room provides even more flexibility for gatherings, hobbies, or recreation. Recent improvements include new flooring, a new septic system, and a new roof, giving you a great foundation to add your own personal touches. The property also offers excellent versatility. It could potentially be used as a second home or rental property, and the layout lends itself to possibilities such as an in-law suite or caretaker accommodations, depending on your needs and applicable approvals. With its private setting, mature trees, extensive waterfront, deep-water boating potential, and flexible floor plan, this four-bedroom Cape Cod with a two-car-plus garage is a rare opportunity to enjoy the Wye River lifestyle. Bring your boat, fishing gear, crab pots, and your vision—and make this special waterfront property your own!

117 River Run, Queenstown

Listing courtesy of Coldwell Banker Realty. Contact:

153 White Tail Ct, Centreville
$725,000
5 Beds ⋅ 3 Baths
Welcome home to this sanctuary that beautifully blends modern comfort with warm Eastern Shore charm. Nestled at the end of a quiet cul-de-sac in the desirable Willow Branch East community, this property offers a sprawling 1.61-acre lot with * 5 BEDROOMS * A welcoming front porch leads into a dramatic two-story open foyer featuring an elegant staircase. The main level boasts a bright, flexible formal dining room or home office and a spacious living room. At the heart of the home is a spacious kitchen fully equipped with Silestone countertops, 42" Maple Toffee cabinetry, and brand-new stainless steel appliances, plus a generous keeping room perfect for large gatherings. Transition effortlessly through the cozy family/sunroom—complete with a stylish barn door—to the rear stone paver patio for seamless indoor-outdoor entertaining. Upstairs, the private primary suite serves as a true sanctuary, showcasing a spacious sitting room and a spa-like en-suite bath with a jetted soaking tub. Four additional bedrooms and a full hall bath provide ample space for family and guests. Premium Andersen windows flood the home with natural light, while upgrades like a Rinnai tankless water heater, reverse osmosis, a water softener, and recent two-zone heat pumps (2023 & 2025) ensure modern comfort. Bonus feature: Light up the neighborhood effortlessly with a built-in, interior holiday light switch wired directly to the front elevation!! Located just minutes from historic Centreville, enjoy peaceful, private living with convenient commuter access to Route 301, Annapolis, Easton, and the Chesapeake Bay Bridge.

153 White Tail Ct, Centreville

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

228 Prospect Bay Dr W, Grasonville
$1,495,000
5 Beds ⋅ 4 Baths
Some homes are simply places to live. This is a lifestyle. Welcome to 228 Prospect Bay Dr W, an exceptionally maintained and thoughtfully updated home where beautiful water views, resort-style outdoor living, and the coveted Prospect Bay community come together in one unforgettable property. From the moment you arrive, the setting makes an impression. Mature landscaping, a gracious exterior and glimpses of the water create a sense of arrival that feels distinctly Eastern Shore. Step inside and you’ll quickly see that this home has been meticulously cared for and intentionally improved, blending timeless coastal character with sophisticated, modern updates. Hardwood floors extend throughout both levels, while custom trim work, designer wall treatments, updated lighting and carefully selected finishes give each space its own personality. The beautifully updated kitchen is designed for both everyday living and entertaining, featuring new countertops and backsplash, an enhanced island with additional storage, pull-out cabinetry and under-cabinet lighting. Just beyond, the sunroom provides a light-filled retreat overlooking the pool and outdoor living spaces. Formal living and dining areas offer an elevated place to gather, while the family room centers around a striking shiplap accent wall, electric fireplace and quartz hearth. Upstairs, the primary suite feels like a private escape, complete with water views, a masonry fireplace, expanded custom closet and beautifully remodeled spa-like bath with a tiled shower, marble seat, soaking tub and dual vanities. Three additional bedrooms and a well-appointed guest bath provide plenty of room for family and guests, while the bonus space over the garage offers flexibility for an office, studio, additional sleeping space or storage. Outside is where the Prospect Bay lifestyle truly comes alive. The backyard has been transformed into a private resort with a large inground pool, extensive hardscaping, Trex decking, hot tub, pergola and lush landscaping, all surrounded by mature trees for privacy. Steps from the pool, the charming separate guest house creates an incredible space for extended stays, offering its own bedroom, full bath, kitchenette and living area. And while the beauty of this home is immediately apparent, what sets it apart is the level of care behind the scenes. Major improvements include a new roof and gutters in 2024, three high-efficiency heat pumps in 2023, an encapsulated crawlspace in 2023, generator hookup, upgraded electrical service, repaved driveway, updated garage, new washer and dryer in 2026, fresh paint and new landscaping in 2026, along with extensive improvements throughout the kitchen, bathrooms, lighting, flooring, trim and outdoor spaces. All of this is set within Prospect Bay, one of the Eastern Shore’s most sought-after golf course communities, where residents enjoy an 18-hole golf course, clubhouse with restaurant and bar, driving range, tennis and pickleball, community pool, playground, private boat launch and more. Spend summer afternoons by your pool, host friends in the guest house, enjoy quiet mornings overlooking the water, play a round of golf, or launch the boat and spend the day exploring the Eastern Shore. 228 Prospect Bay Dr W isn’t simply a beautifully updated home, it’s the opportunity to live the Prospect Bay lifestyle every single day.

228 Prospect Bay Dr W, Grasonville

Listing courtesy of RE/MAX Executive. Contact:

515 Baxter Rd, Sudlersville
$465,000
3 Beds ⋅ 2 Baths
Welcome home to this 3-bedroom, 2-bath home situated on .75 acres along a peaceful road backing to mature trees and farmland. Inside, you'll find an inviting open kitchen and living area featuring a charming brick wood-burning fireplace, creating a warm and comfortable gathering space. Step outside to the oversized back deck, perfect for entertaining, relaxing, or enjoying the private country setting. The backyard is ready for summer with a fenced 18' x 36' in-ground saltwater pool, offering plenty of space for outdoor fun and gatherings. Adding even more versatility to the property is the 30' x 40' detached garage, approximately five years old, complete with a half bath and 220V electrical service for electric vehicle charging—ideal for vehicles, hobbies, a workshop, or additional storage. Recent updates include a new heat pump in 2026, new furnace in 2025 and roof 5 years old. With plenty of outdoor space, a pool, an impressive detached garage, and peaceful views, this property offers a great combination of comfort, functionality, and country living.

515 Baxter Rd, Sudlersville

Listing courtesy of Benson & Mangold, LLC. Contact:

830 Warbler Way Unit 2843, Chester
$779,990
2 Beds ⋅ 3 Baths
Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. 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.

830 Warbler Way Unit 2843, Chester

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

111 Marshgrass Way Unit 43, Chester
$744,900
2 Beds ⋅ 3 Baths
Every season brings a new perspective from this exceptional top-floor penthouse at Four Seasons at Kent Island. Set within one of the Eastern Shore’s premier 55+ communities, this beautifully appointed residence offers Chester River views from every room, creating a remarkable backdrop from sunrise through sunset. Gently enjoyed as a seasonal retreat, the home reflects a refined coastal aesthetic with custom shiplap accent walls, curated designer lighting, elegant trimmed tray ceilings, and every premium builder upgrade offered. These include GE Monogram appliances, quartz countertops, LVP flooring, electric fireplace, and dry bar glass cabinetry. The sophisticated open-concept design seamlessly connects the spacious living room, gracious dining area, and chef-inspired kitchen, creating an inviting setting for entertaining or simply relaxing.  Beyond the residence, Four Seasons at Kent Island offers an exceptional resort-style lifestyle. Enjoy the heated indoor and outdoor pools, scenic Chester River walking trails just steps from the property, and a vibrant Clubhouse featuring fitness and exercise classes, pickleball, tennis and bocce courts. wellness lectures, mahjong and other board games, numerous social gatherings, and an array of activities designed to bring neighbors together. With the ease of low-maintenance condo living, beautiful waterfront surroundings, convenient access to local marinas, and easy connectivity to the Bay Bridge and points beyond, this penthouse captures the very best of the Eastern Shore lifestyle—elevated, effortless, and truly exceptional

111 Marshgrass Way Unit 43, Chester

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

129 Anna Carol Dr, Stevensville
$650,000
4 Beds ⋅ 3 Baths
Coastal charm, exceptional living spaces, and a coveted main-level primary suite come together beautifully in this standout Ellendale at Kent Island home. Mature landscaping and an expansive covered front porch create an inviting first impression, while inside, hardwood floors, crown molding, chair rail, and thoughtful architectural details give the home warmth and character from the moment you enter. At the heart of the home, the kitchen and family room form a spacious, open gathering area designed for both everyday living and entertaining. The beautifully appointed kitchen features granite countertops, stainless steel appliances, gas cooking, recessed lighting, and pendant lighting above a generous center island with breakfast bar seating. Open to the kitchen, the family room is enhanced by a soaring cathedral ceiling and offers plenty of space to gather, while direct access to the screened porch extends the living area outdoors, creating an easy flow for entertaining. A separate open dining area provides a dedicated setting for meals and gatherings, while a phenomenal butler’s pantry is equally accessible from both the dining area and kitchen. More than simply additional storage, this thoughtfully designed space features granite countertops, a wine refrigerator, and a double-door pantry, allowing it to function beautifully as a beverage station, serving area, additional prep space, and pantry, all while providing a natural connection between the kitchen and dining area. Privately positioned away from the main gathering spaces, the main-level primary suite offers an inviting retreat with an oversized walk-in closet and a spacious en suite bath featuring dual vanities and a tiled walk-in shower. A powder room and conveniently located laundry room complete the main level. Upstairs, an exceptionally spacious open landing overlooks the family room and leads to three bright bedrooms and a well-appointed full hall bath with ceramic tile flooring and a tiled shower. One bedroom connects to a separate finished sitting room or study, creating an especially versatile suite with space for a private office, reading room or hobby space. Large windows fill the upper level with natural light, while charming coved ceilings and wide baseboard molding add another layer of architectural character. Storage is another standout feature. An interior staircase provides convenient walk-down access to an expansive, storage area beneath the home, offering an unusually generous place for seasonal décor and household items. At the rear, an alley leads to the driveway and two-car garage, discreetly positioning parking away from the front of the home and preserving its charming streetscape. Adding to the home’s everyday efficiency, the solar panels are owned outright, providing the opportunity for substantial savings on electricity with no solar lease to assume. Ellendale at Kent Island completes the package with a clubhouse, community pool, tot lot, and recreational amenities in a setting that combines the relaxed character of Maryland’s Eastern Shore with exceptional accessibility. Located approximately one mile from the Chesapeake Bay Bridge, the community is convenient to historic Stevensville, Kent Narrows, Terrapin Nature Park, and public water access at Thompson Creek. Boating, waterfront dining, walking and biking trails, and the natural beauty of Kent Island are close at hand, while Annapolis and destinations throughout the greater Washington-Baltimore region remain within easy reach—a remarkable combination of coastal living and everyday convenience.

129 Anna Carol Dr, Stevensville

Listing courtesy of Northrop Realty. Contact:

325 Rings End Rd, Millington
$589,000
5 Beds ⋅ 3 Baths
Discover an exceptional investment opportunity with this stunning Colonial-style residence operating as a guest favorite on Airbnb. Perfectly positioned just 16 feet from the serene Chester River. Step inside to find an inviting open floor plan that seamlessly connects the family room to the kitchen, creating a warm and welcoming atmosphere. The home is adorned with built-ins and window treatments that enhance its charm, while the cozy carpet and wood floors add a touch of elegance throughout. The property features two fireplaces, providing a cozy ambiance during cooler months, and an attic for additional storage or potential expansion. The upper-floor laundry adds convenience, making this home not only beautiful but functional as well. Outside, the allure continues with a personal in-ground pool, perfect for relaxation and recreation. The expansive 1.43-acre lot offers ample space for outdoor activities, while the breathtaking water views create a tranquil backdrop for your daily life. With water access just steps away, you can enjoy kayaking, fishing, or simply soaking in the natural beauty of the Chester River. From an investment perspective, this property stands out with its excellent condition and desirable features. The combination of spacious living areas, modern amenities, and proximity to water activities makes it highly attractive for potential renters or future buyers. The growing demand for waterfront properties ensures that your investment will appreciate over time, providing both immediate enjoyment and long-term financial benefits. This residence is not just a home; it's a lifestyle choice that offers the perfect blend of comfort, luxury, and investment potential. Don't miss your chance to own a piece of paradise that promises both personal enjoyment and financial growth. Seize this opportunity today!

325 Rings End Rd, Millington

Listing courtesy of Hostetter Realty. Contact:

101 Chestnut Rd, Stevensville
$455,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully maintained and thoughtfully designed home, ideally situated on a desirable corner lot with a fully fenced backyard. Offering an excellent combination of comfort, functionality, and style, this property is an ideal opportunity for a first-time buyer, growing family, or anyone looking for a move-in-ready home. Step inside and you’ll immediately appreciate the inviting traditional floor plan, enhanced by beautiful new wood flooring, recessed lighting, upgraded countertops, and an abundance of natural light. The spacious family room flows seamlessly from the kitchen, creating a comfortable and welcoming space for everyday living and entertaining. The well-appointed kitchen offers an abundance of workspace and storage, featuring a center island, pantry, eat-in area, table space, upgraded countertops, built-in microwave, built-in range, self-cleaning oven, dishwasher, and exhaust fan. Whether you’re preparing a quick breakfast or hosting family and friends, this kitchen provides the convenience and functionality today’s homeowners desire. The home offers two full bathrooms, including one with a convenient walk-in shower. Generously sized bedrooms provide comfortable living spaces, while walk-in closets offer excellent storage. Ceiling fans and window treatments throughout the home add comfort and convenience. The main-level laundry area makes everyday living simple and efficient, with a washer and electric dryer included. Additional features include storm doors, double-hung windows, an electric alarm system, an owned water-conditioning system, a water-treatment system, and a water heater. The crawl space has also received important improvements. All cavities and walls have been fully insulated and sealed, and a dedicated dehumidifier system has been installed to help maintain a cleaner, drier, and more controlled environment beneath the home. Outside, the spacious corner-lot setting and fully fenced backyard provide plenty of room for outdoor enjoyment, entertaining, gardening, play, or simply relaxing. The backyard offers the privacy, flexibility, and functionality many buyers are looking for, making it an ideal space for families and outdoor activities. With its comfortable living spaces, practical upgrades, excellent storage, and inviting outdoor setting, this home offers an exceptional opportunity to establish roots and enjoy years of comfortable living. Whether you’re purchasing your first home, looking for additional space for your family, or simply searching for a well-maintained property in a desirable setting, this home is one you won’t want to miss.

101 Chestnut Rd, Stevensville

Listing courtesy of EXP Realty, LLC. Contact:

1616 Postal Rd, Chester
$600,000
Let your home business dreams become a reality! Zoned mixed use residential/commercial! This charming traditional home, offers a perfect blend of comfort and functionality. With 2,818 square feet of thoughtfully designed living space, this residence features five spacious bedrooms and two and a half bathrooms, ensuring ample room for relaxation and privacy. Step inside to discover a cozy family room with wood burning fireplace that seamlessly connects to the kitchen, creating an inviting space for gatherings and everyday living. The kitchen boasts a gorgeous quartz island, perfect for casual meals or entertaining guests as well as a tastefully designed formal dining room. As you move upstairs, you'll find four spacious bedrooms and 2 full bathrooms including a primary suite. Enjoy the luxury of a soaking tub in the primary bathroom, providing a serene escape after a long day. The 3rd floor features an oversized bedroom or recreation room. The possibilities are endless, create a home gym, theatre or gaming room or office space. Outside, the property features a side-entry garage with additional storage space, ensuring convenience and organization. The 0.27-acre lot provides a lovely fenced in outdoor area for gardening or simply enjoying the fresh air. This home is not just a place to live; it's a place to create lasting memories. Experience the perfect blend of style, comfort, and functionality in this delightful residence. Multi-use zoning allows your home business dreams to come true. Zoned residential and commercial.

1616 Postal Rd, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

205 Dominion Ln, Chester
$300,000
3 Beds ⋅ 2 Baths
Opportunity on Kent Island! Welcome to 205 Dominion Lane in Chester, a detached home situated on a 0.27-acre lot with plenty of potential for the right buyer. Currently used as a rental, this property offers an opportunity for homeowners, investors, or buyers looking to make a home their own. While the property could benefit from some updates and TLC, it provides a chance to add value through improvements and personal touches. Whether you're looking for a primary residence, an investment property, or your next renovation project, this home offers flexibility in a desirable Kent Island location. Enjoy convenient access to shopping, dining, local amenities, and Route 50 for commuting. Bring your vision, explore the possibilities, and schedule your showing today!

205 Dominion Ln, Chester

Listing courtesy of LPT Realty, LLC. Contact:

1509 Calvert Rd, Chester
$1,350,000
4 Beds ⋅ 3 Baths
Coastal elegance meets effortless waterfront living on the sunrise side of Prospect Bay. From the moment you arrive, this exceptional home feels special. Ideally positioned on a picturesque jut of land, the setting offers a bit of additional protection while showcasing beautiful, ever-changing water views and spectacular sunrises. A circular driveway leads to a charming courtyard entrance framed by lush perennial gardens. Inside, the views immediately take center stage. An open, coastal elegant floor plan bring the beauty of Prospect Bay into every living space. Coffered ceilings elevate the spacious family and dining rooms, while substantial crown molding and elegant finishes add timeless character throughout. The expansive kitchen is as beautiful as it is functional, featuring a 9-foot island with seating, stainless steel appliances, wine cooler, accent lighting, soft-close cabinetry and drawers, and a pantry. And the views? Simply fabulous. Large sliders open to the heated and cooled sunroom, where walls of windows create a spectacular connection to the water. Designed for both entertaining and relaxing, this may quickly become your favorite room in the house. The custom bar is an exceptional conversation piece, crafted with mahogany and other wood from a 1963 Chris-Craft. The primary suite offers a private retreat with water views and direct access to the waterside patio. A generous, customized walk-in closet leads to the beautifully appointed primary bath, featuring double sinks, a private water closet, and an extraordinary L-shaped tiled walk-in shower with showerheads on two walls. Two bedrooms are thoughtfully positioned on the opposite wing of the home with 1 additional bed and full bath on primary wing. Outside, waterfront living truly comes alive. Enjoy morning coffee and evening gatherings on the Trex deck, or head down to the private pier where two boat lifts await, including an impressive 12,000-pound lift. A spacious shed provides convenient additional storage. And the community setting adds even more to the lifestyle, with a boat ramp, waterfront children's playground, picnic area, and kayak launch—all offering easy ways to get outside and enjoy. This home is designed for waterfront living.

1509 Calvert Rd, Chester

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

1007 Oyster Cove Dr, Grasonville
$1,199,000
3 Beds ⋅ 4 Baths
SPECTACULAR WATERFRONT VIEWS OF A LIFETIME! Luxury and the Coveted "BIG SIX" Rare to Come on the Market * Full Water Access * Deeded 40' Deep Water Boat Slip * Attached Garage * 3 Waterside Decks * Experience the epitome of Luxury Living in this exquisite waterfront townhouse nestled in the prestigious Oyster Cove community. This stunning 3-bedroom, 3.5-bath plus a spacious bonus room with it's own private walk out deck gives you that flexible space for a bedroom suite, a home office, or a game room! An open floor plan on the main level is adorned with rich hickory wood floors, recessed lighting, the ambiance of a wood burning fireplace, and a gourmet kitchen featuring upgraded countertops and new stainless steel appliances. Panoramic Bay Views from your open family room, dining room and waterside deck!! Indulge in the primary suite with Breathtaking Bay Views, a walk-in closet, and a spa-like bathroom complete with a whirlpool tub and walk-in shower. Step outside to your private oasis, where a walk out deck off your bonus room invites you to unwind while overlooking the serene Eastern Bay. Enjoy exclusive access to community amenities, including a saltwater pool, tennis/ pickleball courts, a dog park and a 1 1/2 mile trail that connects to the 38+ mile Cross Island Trail! With a gated entrance and meticulously maintained grounds, this home offers a feeling of both tranquility and security. Located just steps from many local restaurants, coffee shops, tiki bars, and dessert spots! You are just minutes to premier golf courses and designer outlet shopping! Move right in and start enjoying an elevated Waterfront Lifestyle!

1007 Oyster Cove Dr, Grasonville

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

34 Queen Anne Way Unit A, Chester
$570,000
2 Beds ⋅ 2 Baths
The view is the main event. Homes throughout Queens Landing sit at varying distances from the waterfront, and it is hard to get closer than this. Positioned directly along the Chester River, this end unit delivers huge, panoramic water views that immediately set it apart. The windows are perfectly positioned to take full advantage of the setting, giving you a front-row seat to passing boats, changing skies, and some of the most beautiful views on Kent Island. Inside, the home offers a bright, open floor plan with **dual primary suites**, including one conveniently located on the main level—no steps needed for everyday living. The layout ideal for guests, multigenerational living, or simply having a private retreat on each floor. The main level features luxury vinyl plank flooring, an updated kitchen with stainless steel appliances and granite countertops, and a separate bar area with a wine refrigerator. Shiplap accents bring in just the right amount of coastal character while keeping the space comfortable and inviting. Upstairs, the expanded loft has been thoughtfully enclosed, adding approximately 120 square feet of additional living space. There is plenty of room for a family room or media space along with a separate office, reading nook, or flex area. And even from the upper level, those incredible Chester River views remain front and center. Queens Landing offers a true waterfront lifestyle with a clubhouse, heated outdoor pool overlooking the marina and Chester River, fitness center, tennis and pickleball courts, and easy access to the Cross Island Trail. Restaurants, marinas, shopping, and everyday conveniences are nearby, with Route 50 providing easy access to Annapolis, Baltimore, Washington, D.C., and the beaches.

34 Queen Anne Way Unit A, Chester

Listing courtesy of RE/MAX Executive. Contact:

225 Hickory Ridge Dr, Queenstown
$1,195,000
4 Beds ⋅ 3 Baths
A Private Wye River Sanctuary! Some properties offer a home. Others offer a lifestyle. This exceptional Wye River retreat offers both.Set along one of the Eastern Shore’s most beautiful waterways, this beautifully updated ranch home is an invitation to slow down, entertain effortlessly, and enjoy waterfront living at its finest. From morning coffee on the screened porch to sunset swims in the Gunite pool, every day here feels like a getaway.The light-filled, open interior provides an inviting backdrop for relaxed gatherings and everyday living, while a versatile additional living area offers the flexibility for an in-law suite, private home office, game room, or guest retreat. The serene primary bedroom enjoys direct access to the screened porch, creating a private connection to the tranquil waterfront setting.The extensive improvements provide peace of mind while enhancing the home's appeal, including an architectural roof, vinyl siding, gutters, sophisticated hybrid heat pump/propane HVAC system, select updated flooring, and an updated BAT septic system.Outside is where this property truly shines. The Gunite pool features strategically placed bench seating, creating the perfect vantage point for unforgettable Wye River sunsets. The screened porch captures the river breezes and provides an ideal setting for morning coffee, afternoon cocktails, or long evenings with friends and family.For the boating enthusiast, the private dock features two electric boat lifts—8,000 and 12,000 pounds—and 2+ feet of mean low water, providing excellent access for boating and watersports. Spend the day on the river, catch crabs from the dock, or simply let the water set the pace.This is more than a waterfront home—it is a place to create traditions, host unforgettable gatherings, escape the ordinary, and experience the Wye River in a deeply personal way.Private waterfront. Private dock. Gunite pool. Sunset views. Exceptional outdoor living. A rare opportunity to make the Wye River your everyday retreat.

225 Hickory Ridge Dr, Queenstown

Listing courtesy of Pearson Smith Realty, LLC. Contact:

251 Prospect Bay Dr W, Grasonville
$1,550,000
4 Beds ⋅ 4 Baths
Enjoy broad water views and spectacular sunsets from this beautifully situated 1.02-acre waterfront property, with water views enjoyed throughout much of the home. Designed for comfortable one-level living, this spacious residence offers 4 bedrooms, 3.5 baths providing 3,137 square feet of living space. The bright kitchen features a skylight, center island with seating, and an open layout connecting seamlessly to the family room with fireplace. The waterfront primary suite takes full advantage of the views and includes a large walk-in closet, private bath with soaking tub, walk-in shower and dual vanities, plus primary has direct access to a semi-private deck. An additional guest bedroom features its own ensuite bath. Oversized 2 Car Garage. Outdoor living is a highlight, with a swimming pool, deck with awning, patio, generous backyard, riprapped shoreline, and a new pier completed in 2026, Roof New in 2021. This property offers an ideal setting for relaxing, entertaining, and enjoying life on the water. The community offers resort-style amenities, including an 18-hole championship golf course, clubhouse with restaurant/bar/grill, swimming pool, tennis and pickleball courts plus. With expansive water views, beautiful sunsets, one-level living, a private pool and pier, this exceptional property offers the Eastern Shore waterfront lifestyle at its best.

251 Prospect Bay Dr W, Grasonville

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

347 Claiborne Dr, Centreville
$549,900
3 Beds ⋅ 3 Baths
Welcome to 347 Claiborne Fields Drive, situated on an impressive 1.26 acre lot in the sought-after Claiborne Fields community of Centreville! With over 2,000 square feet of living space, this 3 bedroom, 2.5 bath home has been well maintained and cared for by the original owner for many years. Fresh paint and new carpet throughout give the home a clean, refreshed feel, making it ready for its next chapter. An attached two car garage provides added convenience and plenty of space for parking and storage. Enjoy plenty of room to spread out both inside and out, with a spacious lot backing to woods for added privacy and a peaceful setting. Located in an established community with convenient access to Centreville and Route 301, this home offers a wonderful combination of space, privacy, and location. Come see all that 347 Claiborne Fields Drive has to offer!

347 Claiborne Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact:

117 Harrier Way, Chester
$775,000
3 Beds ⋅ 2 Baths
Welcome to this beautifully upgraded Killarney model in Four Seasons at Kent Island, offering true one-level living with no steps, three spacious bedrooms, and the largest garage offered in the community. Unlike many Killarney models featuring two bedrooms and a loft, this home offers three true bedrooms, a dedicated laundry room, and an additional bump-out ideal for a home office or den. The open-concept interior features an Ultra Gourmet Kitchen with quartz countertops, upgraded cabinetry and appliances, double wall ovens, a French-door refrigerator, and a large center island perfect for entertaining. The spacious primary suite includes an Ultra Luxury Spa Bath with a walk-in shower and dual vanities. Tray ceilings, a fireplace, and custom window treatments add to the home's appeal. The oversized garage provides exceptional space for vehicles, a golf cart, and additional storage. Situated on a $55,000 premium homesite, the property enjoys a spacious backyard with generous separation from neighboring homes, offering a wonderful sense of privacy. An expansive custom hardscaped patio creates the perfect setting for outdoor dining, entertaining, and relaxation. Four Seasons at Kent Island offers resort-style 55+ living along the Chester River, featuring a 24,000-square-foot waterfront clubhouse, indoor and outdoor pools, a fitness center, pickleball and tennis courts, walking trails, a dog park, fishing pier, transient boat slips, waterfront Tiki Bar, and an active social calendar. With its desirable floor plan, premium homesite, exceptional garage space, and extensive upgrades, this Killarney presents a rare opportunity to enjoy the best of Four Seasons living.

117 Harrier Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

162 Kirwans Landing Ln, Chester
$1,160,000
5 Beds ⋅ 3 Baths
Enjoy the benefits of a direct water access property without the high price of a direct waterfront view lot. Completely reimagined in 2026, this professionally designed Kent Island retreat combines extensively renovated interior with 1.4 private flat acre lot, a saltwater pool, and a 90-foot pier with direct access to Kirwan Creek. Just five minutes from the Bay Bridge, this 5 bedroom, 3 bath home offer the best of Eastern Shore lifestyle. From the moment you arrive, the outdoor setting feels like a private resort. A sparkling saltwater pool is surrounded by a newly hardscaped stone terrace, mature lawn & landscaping, apple tree, fig tree, cypress tree, and even strawberries! The rear backs up to farmland creating a secluded, private feel. Walk out your front door, directly to the left of the house to access your own pier extends out offering direct access to Kirwan Creek for small boats, kayaking, paddle boarding, fishing, crabbing, wildlife and sunset watching. Moving inside the 3,000 square foot home, the original intent of the owner was to create coastal inspired retreat for anyone who walked through the front doors. Each space has been re-imagined with professional interior designer style throughout with coastal wallpaper, nautical colors, custom curtains, trim work, updated light fixtures and more. The main level heart of the home you'll find an updated kitchen with new light countertops, ceramic tile backsplash, and fresh hardware with a sweet breakfast table nook. Off the kitchen is a dedicated dining room space with gorgeous wallpaper and updated lighting overlooking the backyard. Step down to the airy main living room centered by electric fireplace and opening to a stunning all window sunroom overlooking your backyard paradise.  The main level front room has been converted to functional main level bedroom and the bathroom was updated to a full main level bathroom. Upstairs, the oversized primary suite is designed as a true private retreat, complete with a dedicated lounge area and dreamy spa inspired bathroom. The stunning bath features a freestanding soaking tub, double vanity, large-format tile, and a beautiful tiled shower with dual shower heads. Three additional bedrooms including a custom-designed bunk room with a beautifully renovated hall full bathroom, while a dedicated laundry space off the upstairs hallway adds everyday convenience. The garage was converted into a recreational space (2026) similar to what could be offered by a "finished basement" with versatility to be additional living room, game room, playroom, gym, or easily converted back to the 2 car garage for covered parking. Notable system updates: insulated and added vapor barrier to crawlspace (2026), installed HVAC in garage (2026), main house HVAC (2020), added mini split in sunroom (2022), hot water heater (2022), full primary bathroom renovation (2026), kitchen updated (2026), main level bathroom (2026), hallway renovation bathroom (2026), refinished/stained hardwood floors (2026), newer pool equipment, painted brick on exterior with special masonry paint (2026), and much more (see full list). Nestled within in close-knit community of Kirwans Landing on Kent Island, you are surrounded by homes on large, manicured lots with a strong sense of pride to the overall appearance of the neighborhood. You are walking distance to the community marina with access to private boat slip in deep water - only $400 a year for a slip! A truly turnkey opportunity. Professionally designed and furnished throughout, the home is ready to enjoy immediately. The seller is willing to negotiate a separate package, including furniture, décor, and housewares, allowing buyers to move in without the time or expense of decorating a home. Living on Kent Island offers a waterfront, relaxed lifestyle with a little more space than other waterfront areas in Maryland.

162 Kirwans Landing Ln, Chester

Listing courtesy of Next Step Realty. Contact:

168 Redstart Dr, Chester
$749,900
2 Beds ⋅ 3 Baths
* OPEN HOUSE Saturday, 11/14/2026 from 12-4PM * NEW $15,000 BUYER INCENTIVE -- Take it off the price OR use towards closing! Write it in your Offer! Gorgeous All On One Level Home in Premiere 55+ Community of Four Seasons @ Kent Island * Offering This Lovely Taylor Model w 2 Bedrooms + Den + 2.5 Baths and 3rd Car Tandem Garage * Walkable to Clubhouse * Gorgeous Light-Colored Laminated Wood Flooring * Impressive Island w Bar Overhang/Counter Seating + Added Optional Bank of Cabinets w Bonus Counter Space * Pantry * Gas Cooking * Tile Backsplash * Under Cabinet Lighting. This Turn-Key Taylor Model Offers a Comfortable 2014 sf of Living Space with Large Volume Ceilings and Flowing Ever Popular Kitchen-to-Dining-to-Family Room Floor Plan at the Center of the Home. The Bedrooms are Flanked with the 2nd Bedroom with En Suite Full Bath + Walk-In Closet at the Front of the Home and a Rear Facing Primary Bedroom with Tray Ceiling, Triple Windows + Walk-In Closet and En Suite Full Bath with Substantial His 'n Her Vanities and Easy Walk-In Shower. Off the Foyer there is a Versatile Flex Room Accented with Sliding Barn Doors Which Serves Nicely as a Den/Office/Additional Sleeping Area for the Grandkids and Serviced by the Foyer Powder Room Across the Hall. Around the Corner is a Built-In Coat Drop Station and Separate Laundry Room with New Full-Sized Front-Loading Washer and Dryer. The Garage is Spectacular Offering Coveted Additional Parking for a 3rd Car/Golf Cart OR Use it as Additional Storage/Workshop Area. This Home is Propane Gas Heat, Central A/C, Rinnai Tankless Gas Water Heater and Public Water, Public Sewer. At a Mere 1 Year Old, This Home Feels Brand New and Has Been Lightly Lived In and Lovingly Maintained. It Offers an Immediate Move-In Scenario for the Lucky Buyer. Don't Wait for the Builder and Be in by the Holidays! AGENTS: We Are Agent Friendly and We Split Transfer Taxes and Recordation Fees with the Buyer and Offer a Re-Issue Rate on the Title Insurance + Survey to Pass On. The Community of Four Seasons Offers Unparalleled Amenities and a Friendly, Neighborly Environment That All Enjoy and Gather at a 24,000 sf Club House Situated on the Chester River and is Home to a Community Space Where Vibrant Activities are Available to its Vibrant Neighbors and Provides Resort Style Gym, Yoga, Billard's Room, Library, Ballroom and Indoor Pool w Hot Tub + Infinity Outdoor Pool, Cabana, Lounge Areas, Amphitheatre, Fishing Pier, Dog Park, Pickle Ball, Tennis, Bocce Ball + Tot Lot. Homeowners Get Included Grass Cutting, Fertilization + Pesticide Spraying and Lawn Irrigation as a Part of the $315 Monthly HOA Fee Allowing You to Spend More Time Enjoying and Less Time Maintaining! Located 20 Minutes to Historic Downtown Annapolis and to the Regional Anne Arundel Medical Center with an Outpatient Pavilion in Kent Island. It is 30 minutes to Baltimore/Washington International Airport and there are numerous local airport shuttle services offering door to door service making travel easy and stress free for you and your visiting guests. Kent Island Offers a Variety of Wonderful Restaurants Featuring Local Seafood Cuisine + Numerous Marinas and a Freedom Boat Club Location. Four Seasons @ Kent Island is a Wonderful Year-Round or 2nd Home Location for Those Envisioning a Nautically Inspired Lifestyle Combined with a Beautiful, Maintenance Free Home. 168 Redstart Dr is Waiting For You! Call Helpful Lister for More Info.

168 Redstart Dr, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

225 Autumn Ln, Centreville
$499,000
4 Beds ⋅ 3 Baths
Welcome to this lovely 4-bedroom, 2.5-bath home tucked away on a quiet cul-de-sac in the private community of Heritage, right in the heart of Centreville! Inside, you’ll find beautiful hardwood floors throughout much of the main living area, along with carpeting that is only 1 year old. The spacious kitchen offers plenty of room to gather, featuring a large island and gas cooking, while the adjoining living room provides a cozy gas fireplace for relaxing on chilly evenings. A separate family room offers additional living space, as well as a separate dining room for larger gatherings. The convenient upper-level laundry is located right outside the bedrooms, all of which are very spacious. The primary bedroom features an updated shower. Recent improvements include a new water heater approximately 1 year old, a new backyard fence, and an HVAC compressor believed to be approximately 5 years old. Step outside to enjoy the large covered front porch, or relax in the Sunroom/3 Season Room with skylights, overlooking a private backyard that backs to protected trees. Seasonal winter views of the stream beyond the backyard add to the peaceful setting and natural backdrop. Ideally located close to Centreville’s schools, dining, shopping, parks and the Wharf, with easy access to major commuting routes, this home offers comfortable living in a convenient Centreville location.

225 Autumn Ln, Centreville

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

206 Melvin Ave, Grasonville
$464,900
3 Beds ⋅ 3 Baths
Welcome home to this beautifully maintained and fully updated 3-bedroom home, just 8 years young! Featuring like-new systems and roof, this home offers modern comfort and peace of mind. A 4-foot bump-out provides additional living space, while the upgraded kitchen boasts stainless steel appliances and sliding glass doors leading to a spacious 12x20 composite deck—perfect for entertaining. Enjoy outdoor living with an above-ground pool, fully fenced backyard with white vinyl privacy fencing, and a crushed stone patio that leads to a cozy fire pit area. The long gravel driveway and oversized two-car garage offer ample parking and storage. Inside, you’ll find a spacious primary bedroom with a private full bath, plus an additional family room on the lower level with a convenient half bath—ideal for extra living space, guests, or a home office. Perfectly maintained from the front door throughout, this hidden gem is conveniently located near Route 50, making it an excellent choice for commuters. Stairs have recently been painted pictures will be updated soon .No HOA!

206 Melvin Ave, Grasonville

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

105 E Brook Dr, Centreville
$549,000
4 Beds ⋅ 4 Baths
Welcome to 105 E Brook Drive, located in the sought-after North Brook community of Centreville, MD! Situated on an oversized corner lot with plenty of room to expand, this beautifully refreshed home offers 4 bedrooms, 3.5 bathrooms, and the space and flexibility today's buyers are looking for! Step inside to discover gorgeous refinished hardwood floors, fresh paint throughout, and new carpeting (2026), creating a bright and inviting atmosphere. The kitchen features brand-new appliances (2026), while a new tankless water heater (2026) adds modern efficiency and convenience. Upstairs, the spacious primary suite offers a relaxing retreat, complete with two closets and a private bathroom featuring tile floors, a soaking tub, and a separate stand-up shower. The fully finished basement provides incredible additional living space, perfect for a recreation room, home office, entertaining, or hosting guests. Outside, enjoy the patio overlooking the expansive backyard, offering endless possibilities for outdoor entertaining, play, or future improvements. Beyond the home, the North Brook lifestyle is just as inviting! Enjoy a community designed for outdoor living and connection, featuring scenic walking paths, peaceful ponds, a community pavilion, playground, and soccer field. Whether you're enjoying an evening stroll, spending time outdoors, or gathering with neighbors, North Brook offers the perfect blend of neighborhood charm and everyday convenience. With thoughtful updates, generous living space, an exceptional corner lot, and a community you'll love coming home to, 105 E Brook Drive offers more than just a home, it's a lifestyle! Don't miss your opportunity to make it yours!

105 E Brook Dr, Centreville

Listing courtesy of RE/MAX Executive. Contact:

231 Dominion Rd, Chester
$599,000
Unique opportunity to own a versatile three-unit property situated on approximately one-half acre in Chester. The property features a main residence with 2 bedrooms, 1 full bathroom, and a full basement, offering comfortable living space for an owner-occupant or tenant. A separate building on the property includes two additional rental units: a ground-level 1-bedroom efficiency apartment and an upper-level unit with 2 bedrooms and 1 full bathroom. This setup provides excellent income-producing potential while maintaining privacy between residences. Conveniently located near shopping, dining, and everyday amenities, this property is ideal for investors or buyers seeking a live-in rental opportunity with multiple income streams.

231 Dominion Rd, Chester

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

231 Dominion Rd, Chester
$599,000
5 Beds ⋅ 3 Baths
A rare opportunity to own a property that combines comfortable living with income-producing potential. The primary residence features 2 bedrooms, 1 full bathroom, and a full basement, offering ample storage and living space. Behind the main home is a separate building with two additional rental units. The lower-level unit is a cozy 1-bedroom efficiency apartment, while the upper-level unit offers 2 bedrooms and 1 full bathroom, providing excellent options for rental income or multi-generational living. Situated on approximately one-half acre in Chester, this property offers a convenient location close to shopping, dining, and everyday amenities. Whether you're looking to offset your mortgage with rental income or invest in a versatile property, this unique opportunity is not to be missed.

231 Dominion Rd, Chester

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

129 Wheelhouse Way Unit 21, Chester
$1,399,000
3 Beds ⋅ 3 Baths
Experience exceptional waterfront living in this stunning 3-bedroom, 2.5-bath condominium offering what are arguably the best views in the community. Positioned to capture breathtaking panoramic views of the Chester River, this home provides a front-row seat to beautiful sunrises, and the peaceful beauty of the Chesapeake Bay lifestyle. The spacious primary suite is a true retreat featuring a private sitting room, walk-in closet, and a luxurious en-suite bath. The open-concept design showcases the incredible water views throughout the main living spaces, creating the perfect backdrop for everyday living and entertaining. One of the most desirable locations in the community, this home offers protected water views with no expected future obstruction, allowing you to enjoy the scenery for years to come. Enjoy the convenience of being able to walk to the community pool and amenities without having to drive to the clubhouse. Additional features include a one-car garage with an additional storage room, plus private driveway parking, providing both convenience and storage. Enjoy the ease of maintenance-free waterfront living in one of Kent Island's premier communities, with easy access to marinas, waterfront dining, shopping, and the Bay Bridge.

129 Wheelhouse Way Unit 21, Chester

Listing courtesy of Rise Real Estate, LLC. Contact:

7 Queen Victoria Way Unit B, Chester
$499,000
2 Beds ⋅ 3 Baths
Welcome to 7B Queen Victoria Way at Queen’s Landing, a beautifully renovated waterfront residence w/ spectacular views of the marina basin, marina fairway, and Chester River. The largest residence in Building 7, this spacious 2-bedroom, 2½-bath home with loft offers three levels of living and combines the ease of condominium ownership with the space and feel of a townhome. The extensive renovation creates a fresh, modern, move-in-ready interior featuring an open main level, wide-plank luxury vinyl flooring, refreshed baths, and an updated kitchen with white cabinetry, quartz countertops, stainless-steel appliances, pantry storage, and an eating bar. The waterfront primary bedroom enjoys beautiful views, while the versatile loft is ideal for a home office, guest area, reading retreat, or second sitting room. Step directly from the kitchen onto the gated walk-out waterfront patio and enjoy exceptional water and marina views, outdoor dining, entertaining, or simply watching the boats come and go. Multiple outdoor living areas provide even more opportunities to enjoy the waterfront setting. Queen’s Landing amenities include a waterfront pool and clubhouse, tennis and pickleball courts, fitness and racquetball facilities, scenic walking paths, kayak storage and launch areas, and a full-service marina with slips for sail and power boats. Major renovation, generous living space, outstanding views, and the Queen’s Landing waterfront lifestyle come together at 7B Queen Victoria Way. Offering the best of both worlds---condominium ownership with space, privacy, and multi-level layout of a townhome.

7 Queen Victoria Way Unit B, Chester

Listing courtesy of RE/MAX Allegiance. Contact:

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