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227 Gibson Cir, Chester
$559,900
3 Beds ⋅ 3 Baths
*OPEN HOUSE SATURDAY 10/31/26 11am to 1pm!* 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 Gas 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:

21 Queen Victoria Way, Chester
$472,500
3 Beds ⋅ 3 Baths
Waterfront Living at Its Finest – Premier Marina Basin Location in Queen's Landing! Welcome to one of the most desirable waterfront locations in Queen's Landing! Perfectly positioned directly on the marina basin, this exceptional condominium features the **largest floor plan in the community, offering a true three-bedroom layout PLUS a spacious loft**, two-and-a-half baths, and three levels of comfortable living space. With beautiful, unobstructed marina views and the ability to see your own boat right from your home, this property offers the ultimate Kent Island waterfront lifestyle. Freshly painted and move-in ready, the home features a renovated kitchen, generously sized bedrooms, and luxury vinyl plank flooring installed just two years ago throughout the second and third levels. The HVAC system is less than a year old, providing added peace of mind. The spacious loft offers valuable additional living space, perfect for a home office, guest retreat, or recreation area. The waterfront setting is truly what sets this home apart! Step outside onto your private patio and enjoy expansive, unobstructed views of the marina basin. Unlike patios enclosed by eye-level privacy fencing, this outdoor space allows you to fully appreciate the beautiful waterfront scenery, passing boats, and marina activity without visual barriers. Enjoy the same picturesque setting from your deck and bedroom, where you can look out and see your own boat just steps away. Boating enthusiasts, this is an opportunity you won't want to miss. The seller is offering the option to include TWO boat slips with the purchase at no additional cost—a 25-foot slip equipped with a 10,000-pound boat lift AND an impressive 66-foot slip capable of accommodating a substantial vessel. Imagine waking up, looking out your bedroom window, and seeing your boat waiting in the marina! Whether you own a smaller powerboat, a larger yacht, or both, this rare opportunity offers incredible flexibility and convenience. Not a boater? No problem! Both slips are entirely optional. Queen's Landing offers an impressive collection of resort-style amenities, including a waterfront swimming pool overlooking the Chester River, clubhouse, fitness center, tennis and racquetball courts, community gathering spaces, and grilling areas. Enjoy easy access to the Kent Island Cross Island Trail, nearby marinas, waterfront dining, shopping, and all the recreation that makes Kent Island such a desirable place to call home. Conveniently located just minutes from the Chesapeake Bay Bridge, with easy access to Annapolis, Baltimore, and Washington, D.C., this waterfront retreat is equally suited for a primary residence or weekend escape.

21 Queen Victoria Way, Chester

Listing courtesy of RE/MAX Executive. Contact:

107 Widgeon Way, Chester
$349,900
3 Beds ⋅ 3 Baths
ASSUME A 2.875% FHA LOAN * $1777 MO PYMT *BAYSIDE IN CHESTER/KENT ISLAND * GARAGE TOWNHOME * PRICED TO SELL EXCELLENT OPPORTUNITY TO ASSUME AN FHA 2.875% FIXED INTEREST RATE * Qualified Owner Occupant Buyers: Take Advantage of this rare opportunity to assume this FHA Loan with approximately 25 years remaining * TOTAL PITI PAYMENT OF $1777.56 PER MONTH* You'll Be Way Ahead of the Interest Rate Game AND Own a Spacious 3 Level Garage Townhome in the Popular Community of Bayside with 3 Bedrooms, 2.5 Baths, Deck off Living Room & Propane Gas Fireplace. The Primary Bedroom has a walk-in closet, vaulted ceilings and an ensuite full bath with shower stall and skylight. The Main Level has a spacious open layout with bright and sunny front Kitchen featuring upgraded counters, stainless steel appliances, ample cabinet space and pass through to bar seating on the Dining Room side. The Living Room faces towards the back with Sliders to a Deck great for grilling. Bayside Offers Great Community Amenities to include outdoor pool, exercise room, tennis and volleyball, on-site management AND walking distance to Castle Harbor Marina.

107 Widgeon Way, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

100 Schooner Way, Chester
$545,000
3 Beds ⋅ 3 Baths
Beautiful 3BR/2.5BA Townhome nestled in the desirable waterfront community of Bayside Marina. Pull into your private driveway in front of the attached one-car garage, which offers convenient direct access into your home. Make your way to the covered front porch, open the door, and step inside a beautifully maintained, move-in-ready home. The main level welcomes you with an open-concept design, featuring beautiful wood-tone flooring, recessed lighting, elegant crown molding, abundant natural light, and a neutral color palette throughout. The spacious living room offers a cozy fireplace feature, creating a warm and inviting atmosphere while flowing seamlessly into the dining area and kitchen, making this an ideal space for everyday living and entertaining. The kitchen features abundant cabinetry accented with crown molding, a separate pantry closet, granite countertops, a complementary tiled backsplash, and stainless steel appliances. A center island with breakfast seating provides the perfect spot for casual dining or morning coffee. A conveniently located half bath completes the main level. Upstairs on the second floor, you'll find a spacious secondary bedroom featuring double closets, convenient access to a shared full bathroom, and second-floor laundry. Make your way upstairs to the second floor, where you'll find a spacious secondary bedroom featuring double closets and convenient access to a shared full bathroom. The grand-sized primary suite offers a relaxing retreat, complete with sliding glass doors that open to a private balcony overlooking the community, a large walk-in closet, and a private en suite featuring a jetted soaking tub and a separate walk-in shower. Continue to the third floor, where a generously sized bedroom provides flexible living space to suit your needs. Whether you envision a private home office, a child's playroom, or a comfortable guest bedroom, this versatile space offers endless possibilities. From the sliding glass doors on the main level, step outside onto a spacious covered deck, perfect for outdoor dining, entertaining, or simply relaxing while taking in the beautiful surrounding landscape and peaceful water sounds. The deck leads down to a green space, offering an inviting connection to the outdoors and the charm of waterfront community living. Beautifully maintained and move-in ready, this home offers comfort, versatility, and an inviting setting, all conveniently located near shopping, restaurants, and commuter routes.

100 Schooner Way, Chester

Listing courtesy of LPT Realty, LLC. Contact:

1 Queen Victoria Ct, Chester
$400,000
2 Beds ⋅ 2 Baths
Shore living doesn’t get much better than this! Wake up in this waterfront community perfectly tucked along the Chester River in the vibrant community of Queens Landing. Enjoy the easy, breezy coastal lifestyle with open living spaces, a sunlit kitchen, and a spacious primary suite with a private balcony and cozy fireplace.  Private balcony offers the perfect spot for your morning coffee or evening cocktails—all with peaceful pond views you’ll never get tired of and two patios for your own private peaceful time outdoors. This two bedroom two bath end unit has been fully updated with a beautiful kitchen.  Located just minutes from Route 50, this home is a commuter’s dream while still feeling like a vacation every day. Plus, you’ll have access to incredible amenities like a waterfront pool, marina, clubhouse, fitness center, walking trails, and tennis and pickleball courts—all part of the Queens Landing lifestyle. Easy walkable access to the Cross Island Trail that offers beautiful scenic views. Start living the Shore life you’ve always dreamed of—endless opportunities for boating, fishing, kayaking and crabbing. It's a perfect blend of small town charm, outdoor living, waterfront restaurants, marinas and easy access to Route 50 for a quick trip to Annapolis or DC or the beach! 100% Financing Options For Qualified Buyers!

1 Queen Victoria Ct, Chester

Listing courtesy of Douglas Realty LLC. 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:

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:

510 Auckland Way, Chester
$410,000
3 Beds ⋅ 3 Baths
Welcome home to this beautifully updated end-unit townhome in the desirable Bayside community, facing a peaceful row of trees. This spacious three-level home offers an open, inviting layout, beautiful hardwood floors, and numerous recent updates. Enter from the main-level foyer into a spacious bonus room—perfect for a family room, home office, gym, or additional entertaining space. Step directly outside to the back deck, where you can enjoy grilling and entertaining while overlooking the large grassy common area. Upstairs, the open-concept main living level features a spacious living room with a gas fireplace and access to a second deck, a dining area, and an updated kitchen, all complemented by beautiful hardwood flooring. A convenient updated half bath completes this level. The top floor offers three generously sized bedrooms. The primary suite features a beautiful custom accent wall and an updated primary bath, creating a comfortable and stylish retreat. The updated hall bathroom serves the additional bedrooms. Recent major updates include a new HVAC system (2025) and a new hot water heater (2026). Condo replaced roof and skylight (2025) & power-washed exterior (9/2026). All providing added peace of mind for the next owner. Enjoy all that the Bayside community has to offer, including an outdoor pool, hot tub, tennis/pickleball courts, clubhouse with meeting/party room, and exercise room. The location is ideal for an active lifestyle, with a short walk to the Chester River, a local pub, the Cross Island Trail, and a marina. You'll also enjoy easy access to the Bay Bridge, restaurants, shopping, and all that Kent Island and Maryland's Eastern Shore have to offer. Move-in ready, beautifully updated, and perfectly situated—this Bayside townhome is ready to welcome you home!

510 Auckland Way, Chester

Listing courtesy of Engel & Volkers Annapolis. Contact:

233 Keenan Way, Stevensville
$399,999
3 Beds ⋅ 4 Baths
Easy living and a convenient Kent Island location come together at 233 Keenan Way, an end-unit townhome in the sought-after Ellendale community. Offering three finished levels, 1,884 square feet of living space and a two-car garage, this light-filled home features a flexible floor plan designed for everyday living. The main level is bright and open, with abundant natural light enhanced by the additional windows of an end-unit location. The spacious kitchen features tile flooring, ample cabinetry and counter space, and a large center island with seating. Open to the dining area and adjacent living room with LVP flooring, the layout creates an easy flow for everyday living and entertaining. Step outside to the rear deck for grilling, dining al fresco or simply relaxing at the end of the day. Upstairs, two generously sized bedrooms each feature a private ensuite bath, offering the flexibility of dual primary suites. New carpet adds a fresh update to the upper level. The entry level provides an additional bedroom or flexible bonus space ideal for guests, a home office, fitness room or second living area. Life at Ellendale extends beyond the home, with community amenities including an outdoor pool, clubhouse, tot lot, fishing pier, kayak storage, boat storage and walking paths, with sidewalks and streetlights throughout the neighborhood. Located just minutes from the Bay Bridge and convenient to shopping, dining and everyday necessities at Kent Landing, 233 Keenan Way offers a great combination of space, community amenities and easy access to Annapolis, Baltimore, Washington, D.C. and the Eastern Shore.

233 Keenan Way, Stevensville

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

512 Auckland Way, Chester
$375,000
3 Beds ⋅ 4 Baths
Nestled in the prestigious Bayside community, this exquisite townhouse that was just updated and renovated in 2026 offers a harmonious blend of luxury and comfort, perfect for those seeking an elevated lifestyle. With renovations completed in 2026, this home boasts modern elegance and thoughtful design throughout its 1,899 square feet. Newer roof, HVAC and hot water heater. Step inside to discover a warm and inviting interior with all new luxury vinyl plank and ceramic tile flooring, featuring a floor plan that seamlessly connects the kitchen and living areas. The family room, conveniently located off the kitchen, is adorned with an electric fireplace, creating a cozy focal point for relaxation. The gourmet kitchen is a chef's dream that includes new quartz countertops, backsplash, new stainless steel appliances, built-in microwave, and a cooktop that promises culinary excellence. Ample storage and a spacious layout make meal preparation a delight. The home features three generously sized bedrooms, each designed with comfort in mind, including an updated primary suite with an luxurious walk-in shower, quartz countertops and new tile flooring. Enjoy the convenience of a fully finished basement with a walkout level, providing additional living space and easy access to the outdoors. The basement also includes garage access, ensuring practicality and ease of living. Step outside to your private deck, where the Chester River is just a short stroll away. The community offers an array of amenities, including a sparkling outdoor pool, tennis courts, and a clubhouse, fostering a vibrant social atmosphere. For those who enjoy an active lifestyle, bike trails and exercise rooms are readily available. Parking is a breeze with an attached garage and additional off-street spaces, ensuring ample room for guests. The meticulously maintained grounds, with included lawn care and snow removal, allow you to enjoy your surroundings without the hassle of upkeep. This property is not just a home; it's a lifestyle. Experience the tranquility of riverfront living while being part of a community that values both leisure and luxury. Embrace the opportunity to make this stunning townhouse your own and indulge in the exclusive lifestyle it offers.

512 Auckland Way, Chester

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

15 Qun Ann Way Unit E, Chester
$529,000
2 Beds ⋅ 3 Baths
Located in the beautiful Queens Landing community, this Spanish-style waterfront townhouse offers a luxurious lifestyle with stunning river views. The interior boasts an open floor plan, featuring a combination dining and living area with recessed lighting and a corner gas fireplace. The kitchen is equipped with upgraded countertops and high-end appliances, including a built-in microwave and new additional cabinet and countertop space. Upstairs you will find 2 spacious bedrooms both with private balconies, 2 full bathrooms, and a large loft space above the primary bedroom. Outside you can enjoy your private balcony or relax on the patio, surrounded by beautifully landscaped grounds. The community amenities include an in-ground pool, tennis courts, walking trails, and access to the Chester River. Come tour this waterfront property today!

15 Qun Ann Way Unit E, Chester

Listing courtesy of Benson & Mangold, LLC. Contact:

15 Mariners Way Unit A-1, Stevensville
$265,000
2 Beds ⋅ 2 Baths
Chesapeake Waterfront Lifestyle Without the Waterfront Price Tag! Welcome to a beautifully transformed retreat in Kent Cove, where easy coastal living meets the comfort and convenience of a thoughtfully updated home. This exceptional 2-bedroom, 1.5-bath townhouse offers a rare opportunity to enjoy water views, community water access, multiple docks, resort-style amenities, and expansive outdoor living—all in a peaceful Stevensville setting just one minute from Routes 301/50. From the moment you arrive, you'll notice that this isn't your typical townhouse. Extensively updated and lovingly maintained, the home received approximately $25,000 in improvements in 2018, including a complete kitchen renovation, updated bathrooms, new flooring throughout, stainless steel appliances, granite countertops, fresh paint, updated water-heater components, and a custom cabinet niche/coffee station in the dining area. An additional $3,000 in improvements was completed in 2026, keeping the home fresh and move-in ready. The heart of the outdoor experience is the new 8' x 22' Trex deck—a substantial private entertaining space designed for morning coffee, evening cocktails, outdoor dining, or simply enjoying the peaceful Kent Cove surroundings. A second front deck opens to a relaxing common area, while the semi-private common area behind the home creates an additional sense of privacy and space. And then there's the water. Enjoy water views and community access to the water, with three community docks providing opportunities to take in the scenery and enjoy the Eastern Shore lifestyle. Whether you're looking for a peaceful place to unwind after a long day, a weekend escape, or an easy-care home where you can enjoy the outdoors without the responsibilities of a larger property, Kent Cove delivers. The community's amenities add exceptional value and convenience. The $522 monthly HOA fee includes water and sewer, twice-weekly trash pickup, snow removal, maintenance of common areas, exterior townhouse maintenance, a community pool, and access to three docks. It's a lifestyle designed to let you spend less time maintaining a property and more time enjoying it. A detached one-car garage provides valuable storage and parking, while the two-level layout offers comfortable separation between living and private spaces. Best of all, you get the tranquility and character of Eastern Shore living while remaining incredibly convenient to major commuter routes. Routes 301/50 are just one minute away, putting the Bay Bridge, Annapolis, shopping, dining, and everything Stevensville has to offer within easy reach. Updated. Waterfront-oriented. Turnkey. Low maintenance. Convenient. If you've been waiting for an opportunity to enjoy the Kent Island lifestyle without taking on the price and upkeep of a detached waterfront home, this is the one to see. Come experience the views, the decks, the water, and the unique sense of community that make Kent Cove such a special place to call home.

15 Mariners Way Unit A-1, Stevensville

Listing courtesy of RE/MAX Plus. Contact:

1012 Auckland Way, Chester
$599,900
3 Beds ⋅ 4 Baths
KENT ISLAND WATERFRONT • GOURMET KITCHEN • TWO PRIVATE DECKS • LUXURIOUS PRIMARY SUITE • CLUBHOUSE + FITNESS CENTER • MARINA ACCESS Experience Kent Island waterfront living in this beautifully appointed townhome in sought-after Bayside of Chester. The open-concept interior offers abundant natural light, spacious living areas, and stylish finishes throughout. The gourmet kitchen is designed for both everyday living and entertaining, featuring generous cabinetry, ample counter space, and a large center island with seating that flows seamlessly into the dining and living areas. The spacious primary suite offers a walk-in closet and luxurious ensuite bath, while additional bedrooms and flexible spaces provide room for guests, a home office, or recreation. Enjoy TWO PRIVATE DECKS for outdoor dining, morning coffee, or relaxing in the peaceful surroundings. An attached garage, additional storage, and parking spaces across the street add convenience. Bayside amenities include a clubhouse, fitness center, pool, tennis courts, walking trails, and marina access. Castle Marina slips are available for short-term or annual rental, with select slips near Queens Landing potentially available for purchase. Close to waterfront dining, shopping, golf, and major commuter routes.

1012 Auckland Way, Chester

Listing courtesy of Redfin Corp. Contact:

53 Queen Caroline Ct, Chester
$329,000
2 Beds ⋅ 3 Baths
Nestled in the community of Queens Landing, this townhome offers a blend of coastal charm and contemporary elegance with carefree living. Boat slips with provisioned boats when available through marina along with Kayaking and storage. With 1,440 square feet of thoughtfully designed living space, this home is a sanctuary of comfort and style. Step inside to discover an inviting open floor plan that seamlessly connects the living and dining areas, creating an ideal space for entertaining or quiet evenings at home. The family room, conveniently located off the kitchen, features an electric fireplace, providing a cozy ambiance for gatherings. On the second level, are two bedrooms both with their private full bath. The most recent upgrades include; New HVAC, new electric fireplace, new kitchen appliances (GE Profile), updated bathroom, new shower, new carpeting and painted throughout. The community amenities include access to an outdoor swimming pool, tennis courts, and pickleball courts, all designed for an active and social lifestyle. The clubhouse and fitness center provide additional opportunities for relaxation and recreation. This home is conveniently located off of 301/50 and minutes from the Bay Bridge for an easy commute. to Annapolis/DC or Baltimore. NOTE; Community upgrade for Fios internet in process and a line of new trees is going behind the home this fall for added privacy as per HOA

53 Queen Caroline Ct, Chester

Listing courtesy of EXP Realty, LLC. Contact:

1010 Auckland Way, Chester
$595,000
3 Beds ⋅ 4 Baths
PANORAMIC CHESTER RIVER VIEWS! This fabulous END-UNIT townhome in Kent Island’s sought-after Bayside community offers a special WATERFRONT SETTING with sweeping views of the Chester River as it flows into the Chesapeake Bay. With approximately 2,100 square feet, an abundance of natural light, and water views from so many rooms, this home is all about enjoying the Eastern Shore lifestyle! Beautiful hardwood floors flow throughout the main level, where the kitchen, dining room and family room all take advantage of the spectacular water views. The modern kitchen opens to the living areas, while built-in bookcases and a gas fireplace add character and function to the family room. Step outside to one of two waterside decks and enjoy the ever-changing river views, passing boats and beautiful scenery. Upstairs, wake up each morning to endless WATER VIEWS from the Primary Suite, then step directly onto your private waterside deck with your morning coffee. Bedrooms feature the privacy and convenience of ensuite baths. A large upper-level Bonus Room with its own full bath provides wonderful flexibility—create a 3rd bedroom, spacious home office, a guest suite, den or whatever best fits your lifestyle. The views are even better from up here! Freshly painted and truly MOVE-IN READY, this light-filled end unit offers the combination everyone is looking for—beautiful interiors, flexible living space, two waterside decks and an exceptional location overlooking the Chester River. Bayside offers wonderful community amenities, including a swimming pool, party room, fitness center, tennis/pickleball courts and volleyball. The 38+ mile Cross Island Trail is just around the corner for walking, jogging and biking. You’re also conveniently located near restaurants, grocery shopping, outlet shopping and golf courses. Love boating? The marina bordering the community offers boat slips that may be available for rent or purchase, making it easy to enjoy everything the Chesapeake Bay and Eastern Shore have to offer. Come experience the Kent Island waterfront lifestyle—beautiful views, boating, recreation and convenience, all right outside your door!

1010 Auckland Way, Chester

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact:

208 Topside Dr Unit 211, Stevensville
$610,000
2 Beds ⋅ 2 Baths
Luxury, comfort, and resort-style living come together beautifully in this exceptional Bay Bridge Cove residence! This beautifully appointed home combines elegant finishes, spacious living areas, and an inviting indoor-outdoor lifestyle in a sought-after community. From the moment you step inside, you’ll appreciate the attention to detail. The spacious living room features beautiful crown molding, recessed lighting, and a cozy gas fireplace, creating the perfect setting for relaxing or entertaining. At the heart of the home is a gourmet kitchen designed to impress, featuring an abundance of cabinetry, stainless-steel appliances, generous counter space, and a large pantry providing exceptional storage and functionality. One of the home's most inviting features is the bright and spacious sunroom, surrounded by an abundance of windows that fill the room with natural light. A beautiful cathedral ceiling enhances the open, airy feel, creating the perfect space for morning coffee, casual entertaining, or simply enjoying the peaceful views throughout the seasons. The sunroom provides direct access to the screened porch, creating a seamless flow between the indoor and outdoor living spaces. The home offers two generously sized bedrooms, including a private primary suite with a walk-in closet and spa-inspired bathroom featuring a walk-in shower. Elegant details throughout—including chair railings, crown molding, and luxury vinyl plank flooring—create a sophisticated yet warm and comfortable ambiance. Step outside and enjoy the peaceful setting of a level lot backing to an open common area. The screened porch offers an ideal retreat for outdoor dining, entertaining, or relaxing with a good book while enjoying the tranquil surroundings. Meticulously maintained landscaping and a lawn sprinkler system add to the home's exceptional curb appeal. As a resident of Bay Bridge Cove, you’ll enjoy an impressive array of amenities designed for an active and social lifestyle. The community offers a clubhouse, fitness center, outdoor swimming pool, scenic jog/walk paths, game room, and recreational center—providing plenty of opportunities for fitness, relaxation, recreation, and connecting with neighbors. Additional highlights include an attached two-car garage with convenient interior access, exterior security cameras, and smoke detectors for added peace of mind. Location is another standout feature, with convenient access to major routes, shopping, dining, and restaurants, making commuting, errands, and enjoying the area's many amenities effortless. This is more than a home—it’s an opportunity to enjoy a refined, low-maintenance lifestyle in a vibrant community where comfort, convenience, and resort-style amenities come together. For an additional fee, the home is also available fully furnished, offering a convenient turnkey option for buyers seeking an effortless transition into their new home. Welcome home to Bay Bridge Cove! Schedule your private showing anytime!

208 Topside Dr Unit 211, Stevensville

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact:

1202 Oyster Cove Dr, Grasonville
$719,900
3 Beds ⋅ 4 Baths
Welcome to Oyster Cove Live the Oyster Cove lifestyle! Welcome to a beautifully maintained townhome in Oyster Cove, a gated waterfront community offering the perfect blend of elegance, convenience, and carefree living. Here, the grounds are maintained for you, giving you more time to enjoy the lifestyle you’ve worked for. Residents can take advantage of the community pool, waterfront surroundings, and peaceful, beautifully landscaped setting. Enjoy the best of Grasonville right outside your door—restaurants, shopping, marinas, entertainment, and everyday conveniences are all just minutes away and easily accessible by car, bike, or even a leisurely walk. Whether you’re looking for a full-time residence, a weekend retreat, or a low-maintenance home where you can simply lock the door and go, Oyster Cove offers an exceptional setting. This is more than a townhome—it’s a lifestyle. Come experience the charm, sophistication, and relaxed waterfront atmosphere of one of the area’s most desirable communities. This beautifully refreshed three-level townhouse is move-in ready and priced to sell at $719,900. Freshly painted throughout, featuring brand-new carpet and freshly refinished hardwood flooring, this home offers a clean, updated feel from the moment you walk in. Enjoy the spacious three-level layout with plenty of room for everyday living and entertaining. A private boat slip is included, adding exceptional value for boating and waterfront enthusiasts. Move right in and enjoy all that Oyster Cove has to offer. Don’t miss this opportunity to own a beautifully refreshed townhouse with a boat slip at an attractive price! Thoughtfully staged (virtual) to highlight the home's spacious rooms, functionality, and potential.

1202 Oyster Cove Dr, Grasonville

Listing courtesy of Coldwell Banker Waterman Realty. Contact:

43 Queen Neva Ct, Chester
$445,000
3 Beds ⋅ 3 Baths
Welcome to 43-A Queen Neva Court, a pristine 3-bedroom, 2.5-bath contemporary condo in the sought-after Queens Landing community overlooking the pond. Offering more than 2,000 square feet of living space, the largest model in the community, this spacious end unit features an open, sunlit floor plan that is perfect for everyday living and entertaining. The oversized kitchen provides abundant workspace and storage, while the inviting living area is highlighted by a cozy fireplace. The generous primary suite includes a private bath with a soaking tub and separate shower. Step outside to your patio and enjoy peaceful pond views, added privacy, and the benefits of end-unit living. Queens Landing offers an amenity-rich lifestyle with a community pool, clubhouse, fitness center, tennis courts, and much more. This one is truly a 10/10!

43 Queen Neva Ct, Chester

Listing courtesy of Anne Arundel Properties, Inc.. Contact:

314 Allison Jane Dr Unit H-2, Stevensville
$565,000
4 Beds ⋅ 4 Baths
This charming 4-bedroom, 4-bathroom townhouse in the desirable Ellendale community offers a perfect blend of modern comfort and inviting warmth. Built in 2023, this Baldwin built home features an open floor plan with luxury vinyl plank flooring and carpet in the bedrooms, ideal for both relaxation and entertaining. The spacious kitchen features a large center island and high-quality appliances, including a built-in microwave and dishwasher, making meal prep a delight. Large Deck off dining/kitchen area, too! Enjoy evenings by the fireplace or step out onto the balcony and deck to soak in the serene views of the garden and open common area. Nearby parks and walking paths invite outdoor adventures, while excellent schools and convenient access to commuter lots and the airport ensure a seamless daily routine. With an attached garage and driveway parking, this home is a true gem in a vibrant neighborhood, ready to welcome you home.

314 Allison Jane Dr Unit H-2, Stevensville

Listing courtesy of Wilson Realty & Staging LLC. Contact:

108 Blenny Ln, Chester
$364,900
3 Beds ⋅ 3 Baths
Owner Says Sell! Newly Reduced Price * Bayside Condo Townhomes in Chester * Kent Island - Located in the Popular Community of Bayside just minutes from the Bay Bridge, Castle Harbor Marina for Boaters and all -Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground, so all rooms have windows and the ground floor is a level walk out. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a Concrete Patio. The next level up opens to an Expansive Living Room/Dining Room combo with gleaming hardwood floors, propane gas Fireplace w mantle and sliding glass doors to a rear facing Deck. The Half Bath & L-Shaped Kitchen with pass thru are located in the front of the home, and the Kitchen is nicely updated to include stainless steel appliances, white cabinets, quartz counters, modern oversized sink with single lever faucet and wonderful wall of built-in storage/pantry space. The community of Bayside is a waterside community and conveniently located near Castle Harbor Marina which is a privately owned marina and within walking distance of this townhome. It has public water, public sewer, propane gas for fireplaces and is serviced by Breezeline & Talkie for Internet and Cable. The community amenities include Outdoor Pool + Hot Tub w Lifeguard, Clubhouse with Exercise Room, Upper-Level Party/Meeting Room, Tennis, Volleyball. It has an On-Site Property Manager. The community fees include: grass cutting, snow removal, roof, siding, decks, trash & recycle.

108 Blenny Ln, Chester

Listing courtesy of RE/MAX Leading Edge. Contact:

259 Topside Dr Unit 166, Stevensville
$650,000
3 Beds ⋅ 3 Baths
Welcome to 259 Topside Drive in Bay Bridge Cove, one of Kent Island’s most sought-after 55+ communities! This beautifully upgraded Oxford model offers the spacious, flexible floor plan buyers love, paired with a premium setting overlooking the community pond and fountain. Step inside to an open and inviting main level designed for both everyday living and entertaining. The gourmet kitchen is a standout, featuring beautiful light gray cabinetry, a custom backsplash that complements it perfectly, an upgraded appliance package, generous workspace and an easy flow into the main living areas. A cozy fireplace anchors the living room, while the expanded double sunroom fills the rear of the home with natural light and creates even more space to relax, entertain or simply enjoy the view. Step outside onto the deck and take in peaceful pond and fountain views—the perfect backdrop for morning coffee, an evening glass of wine or unwinding at the end of the day.The Oxford’s flexible design continues upstairs, where you'll find an additional bedroom and full bath along with a spacious loft and separate den featuring built-in shelving. Whether you need private guest accommodations, a home office, hobby space, reading room or an additional living area, this second level gives you options without sacrificing the convenience of main-level living. Located in the heart of Stevensville on Kent Island, Bay Bridge Cove offers an active, low-maintenance lifestyle with a clubhouse, fitness center, outdoor pool, recreational courts, walking and biking trails, and plenty of opportunities to connect with neighbors—all just minutes from shopping, dining, waterfront recreation and the Chesapeake Bay Bridge. This isn’t just an Oxford—it’s an Oxford with the upgrades, expanded living space and pond setting buyers wait for.

259 Topside Dr Unit 166, Stevensville

Listing courtesy of Samson Properties. Contact:

1107 Oyster Cove Dr, Grasonville
$759,000
3 Beds ⋅ 4 Baths
Nestled in the serene enclave of Oyster Cove, this stunning bayfront townhouse offers a harmonious blend of contemporary design and luxurious living. With three spacious bedrooms and three and a half bathrooms, this residence is perfect for those seeking comfort and style. The moment you step inside, you are greeted by an open floor plan that seamlessly connects the living and dining areas, enhanced by beautiful wood floors and abundant natural light. The living space features a cozy fireplace with glass doors, creating an inviting atmosphere for gatherings or quiet evenings at home. The heart of the home is the country-style kitchen, equipped with upgraded countertops and a suite of modern appliances, including a self-cleaning oven, dishwasher, and refrigerator. Enjoy casual meals in the eat-in kitchen or host dinner parties in the elegant dining area. The primary bedroom is a true retreat, boasting bayfront views, a walk-in closet, and a luxurious en-suite bathroom complete with a jetted tub and walk-in shower. Step outside to discover the community's exceptional amenities. Enjoy leisurely afternoons by the saltwater pool, take a stroll along the scenic jog/walk paths, or engage in friendly matches on the tennis and pickleball courts. The gated community ensures peace of mind, while the clubhouse and party room provide perfect venues for social gatherings. For those who love the outdoors, the nearby marina offers water access to the beautiful Eastern Bay, ideal for boating and fishing enthusiasts. Oyster Cove is not just a home; it's a lifestyle. The neighborhood is rich with common grounds, picnic areas, and a dog park, making it perfect for outdoor activities. With easy access to local shopping, dining, and entertainment, everything you need is just a short drive away. This property is not just a place to live; it's a sanctuary where you can unwind and enjoy the beauty of waterfront living. Don't miss the opportunity to make this exquisite townhouse your new home in Oyster Cove, where every day feels like a vacation. Experience the perfect blend of luxury, comfort, and community in this exceptional property.

1107 Oyster Cove Dr, Grasonville

Listing courtesy of Star Realty. Contact:

222 Moorings Cir Unit 126, Stevensville
$585,000
3 Beds ⋅ 3 Baths
Welcome to this stunning home in the picturesque 55+ Community of Bay Bridge Cove - the place for Kent Island living at its best, so close to the waters of the Chesapeake Bay. This 3-bedroom, 3-bath home offers so many upgraded features. Conveniently located across from the community center and backing up to quiet, tree-lined space, you are steps away from enjoying all the amenities the neighborhood has to offer. Welcoming you at the front of the home is your own private courtyard, with space to sit and relax or socialize with friends under the strings of cafe lights. Walk inside to the warm-toned luxury wood plank vinyl floors throughout the entire first floor; abundant light spills in to accent the paneled foyer with upper crown molding. The roomy kitchen features soft-close cabinets/drawers with lots of storage, pull-out trash and recycle bins, a corner cabinet with lazy-susan shelving, stainless steel appliances, premium countertops and backsplash, under-the-counter lighting, and updated cabinet knobs and pendant lights. The main level great room has plenty of space for a large dining table and your comfortable living room furniture, and features a cozy gas fireplace (and includes a convenient wall mount for your TV). Step into the bright and airy sunroom at the back of the home - make it your book nook, office, or a spot to enjoy your guests. The primary bedroom features a tray ceiling, 2 walk-in closets (one is huge!), and a private bath with tiled shower and ceramic tiled flooring. The 2nd bedroom on the first floor connects to the hall bath. A sizable laundry room includes upgraded Samsung appliances, shelving, and a storage closet. Upstairs you'll find a relaxing retreat with a large loft area, a bedroom with walk-in closet, and a full bath. A bonus feature of this home is the beautifully enhanced loft wall on each side with added railing, making this space safe for the little ones while maintaining the line of sight to the first floor. With ceiling fans throughout, added storm doors on the front and back with pull-down screens, unique custom blinds on all windows matched perfectly to the function of each room, and an irrigation system for low-maintenance gardening, this home may be the perfect one you've been looking for! This thriving community has it all - a calendar of activities and outings, bocce and pickleball, picnics at the crab shack, a pool, indoor gym, library, game rooms, community garden and fresh herb garden, walking paths around the beautifully landscaped ponds, and quick access to the Cross Island Trail right next to the neighborhood. There's so much to do here!

222 Moorings Cir Unit 126, Stevensville

Listing courtesy of The KW Collective. Contact:

310 Allison Jane Dr Unit H-1, Stevensville
$569,000
4 Beds ⋅ 5 Baths
Sellers of 310 Allison Jane are offering up to $16,000 toward buyer’s allowable closing costs, prepaid expenses, and/or a lender-approved interest-rate buydown with a mutually accepted contract on or before November 12, 2026. Buyers may alternatively negotiate a price reduction in lieu of the closing-cost credit. All incentives are subject to seller-approved price and terms, lender approval, and applicable loan-program limits. Like new and loaded with upgrades, this stunning end-unit Baldwin townhome is just three years young and offers the perfect blend of style, space, and convenience. Featuring 4 bedrooms, 4 full baths, and 1 half bath, this spacious home was thoughtfully designed for modern living. The heart of the home is the bright white gourmet kitchen complete with quartz countertops, abundant cabinetry, a large center island, and an expanded kitchen/dining bump-out that creates an open and inviting space for entertaining. The adjoining living areas boasts a shiplap focal wall with fireplace and is filled with natural light thanks to the premium end-unit location. Retreat to the luxurious owner's suite with a private bath, while additional bedrooms and baths provide flexibility for family, guests, or a home office. Take outdoor living to the next level on the incredible rooftop deck, perfect for relaxing, entertaining, or enjoying sunset views. Additional features include an attached garage, modern finishes throughout, and the peace of mind that comes with newer construction. Conveniently located in the Ellendale community that offers an outdoor pool, community center, playground, ponds and fishing pier with kayak launch. Close to shopping, dining, commuter routes, and everyday amenities, this turnkey home offers low-maintenance living without sacrificing space or style. This home is also available for rent at $3200/month.

310 Allison Jane Dr Unit H-1, Stevensville

Listing courtesy of Samson Properties. Contact:

111 Ryan Dorsey Ln, Stevensville
$414,989
3 Beds ⋅ 3 Baths
THE LOWEST-PRICED HOME CURRENTLY AVAILABLE IN ELLENDALE — AND NOW WITH AN ADDED BUYER INCENTIVE! Offered at $414,989, PLUS THE SELLER WILL PAY 3 MONTHS OF HOA FEES AT SETTLEMENT WITH AN ACCEPTABLE OFFER! This move-in-ready Kent Island home delivers exceptional value with approximately 1,900 sq. ft., 3 bedrooms, 2.5 baths and a 2-car garage. Two spacious bedrooms are located upstairs, while the finished lower level offers a third bedroom plus additional flexibility for a home office, guest space or gym. Vacant, easy to show and ready for a quick settlement! A recently replaced roof adds peace of mind, and the home is located directly across from the community pond. Enjoy Ellendale amenities including a community pool, clubhouse, pier and floating dock, walking trails, playground and boat storage. Convenient to Route 50 and the Bay Bridge. If you’ve been waiting for the right opportunity in Ellendale, this is one you need to see. Schedule your showing today and come see the value for yourself!

111 Ryan Dorsey Ln, Stevensville

Listing courtesy of Chaney Homes, LLC. Contact:

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