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$1,439,999
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:

$585,000
2 Beds ⋅ 3 Baths
Priced well below market value! The builder can not compete with this price. Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury, convenience, and resort-style living come together in a way that few homes in the community can offer. This beautifully upgraded first-floor Magothy model is not only one of the closest residences to the Chester River, but also enjoys a premium location just one building away from the community clubhouse and only steps from the outdoor and indoor pools. One of the most unique advantages of this first-floor residence is its size. Unlike the second, third, and fourth-floor Magothy models, first-floor units offer approximately 100 additional square feet of living space, creating a more spacious and comfortable layout. Combined with more than $30,000 in post-purchase upgrades, this condo stands apart from the moment you walk through the door. By far the most impressive feature, however, is the extraordinary access to the waterfront. Step through your sliding glass doors and find yourself just moments from the Chester River. The peaceful setting allows you to enjoy water views, wildlife, and gentle river breezes from your private patio while offering one of the most coveted locations within the community. Whether you're taking a morning stroll along the shoreline or relaxing outdoors with a cup of coffee, the river feels like an extension of your backyard. Inside, luxury vinyl plank flooring flows throughout the home, complementing the bright, open floor plan filled with natural light from oversized windows and soaring ceilings. The gourmet kitchen is designed for both everyday living and entertaining, featuring a large center island, under-cabinet lighting, abundant cabinetry, and a custom dry bar area. The adjoining dining and living spaces create a seamless gathering area, highlighted by recessed lighting and a cozy electric fireplace. The spacious primary suite serves as a private retreat with dual closets and a beautifully upgraded bath featuring double vanities, custom tile work, a walk-in shower, and dual shower heads. A generous guest bedroom and adjacent full bath provide comfortable accommodations for family and visitors alike. Additional features include a private locked storage room, garage, custom finishes throughout, and a covered patio accented with stacked stone columns—an ideal place to unwind and enjoy the tranquil surroundings. With the clubhouse and pool just steps away, you'll enjoy unmatched convenience while still maintaining a peaceful and private setting. Residents of Four Seasons enjoy an exceptional resort-style lifestyle with a stunning clubhouse, indoor and outdoor pools, tennis and pickleball courts, fitness facilities, walking and biking trails, a community pier, and a full calendar of social activities coordinated by the community lifestyle director. Conveniently located near waterfront dining, marinas, golf courses, Annapolis, Baltimore, Washington, D.C., and BWI Airport, this is Eastern Shore living at its finest. Opportunities to own a first-floor waterfront-proximity unit in this location are exceptionally rare. With extra square footage, extensive upgrades, steps-to-the-pool convenience, and one of the closest locations in the community to the Chester River, this home offers a lifestyle that simply cannot be replicated.

129 Wheelhouse Way Unit 11, Chester

Listing courtesy of RE/MAX Executive. Contact:

$665,000
2 Beds ⋅ 3 Baths
Built in 2019, this coastal style cutie is BETTER than new & offers a bright open layout that includes 2 SPACIOUS BEDROOMS complete w/private ENSUITE BATHROOMS plus additional HOME OFFICE/DEN or spare bedroom & POWDER ROOM off foyer. There is a 22X10 BONUS storage space in the upgraded GARAGE LOFT/ “Sky-Basement” The stunning CHEF'S KITCHEN is the heart of this home & opens up to DINING AREA & GREAT ROOM. KITCHEN features upgraded CAFE by GE STAINLESS APPLIANCES, granite countertops, a plethora of custom 42" cabinets, huge CENTER ISLAND & PROFESSIONALLY appointed WALK-IN PANTRY. Dining area off kitchen flows seamlessly into the FAMILY/GREAT ROOM complete w/GAS FIREPLACE for cool fall evenings & SUNDAY-FUN-DAY Football gatherings! Enjoy the ease & luxury of a primary bath w/large CUSTOM WALK-IN SHOWER featuring built-in bench, & double vanities . Spacious walk-in closet (also custom-finished) includes a built-in safe for keeping valuables & important documents. And the crowning touch? PLANTATION SHUTTERS throughout--ABSOLUTELY STUNNING---and UNDENIABLY ELEVATED! An OVERSIZED 2-CAR GARAGE complete w/OPTIONAL 22x10 LOFT STORAGE offers a smart, tucked-away solution for everything you want close at hand-but out of sight. The meticulous exterior features a screened porch, & paver patio w/retractable awning providing additional space for entertaining or simply relaxing & enjoying the outdoors. The beautifully landscaped lot backs to trees and popular CROSS-ISLAND TRAIL as well as views of the scenic community water-features, & even has an invisible fence for your four-legged friend. The "Icing On The Cake" is definitely the ABUNDENT AMENITIES (including lawn-care!) covered by your reasonable monthly HOA dues....Stunning (WATERFRONT!) INDOOR & OUTDOOR SWIMMING POOLS, fitness center, DOG PARK, walking paths, fishing/crabbing pier, PICKLE & BOCCE BALL COURTS & SO MUCH MORE- there's always something to see & enjoy. The community also features a beautiful clubhouse with BALLROOM and various multi-purpose spaces for learning opportunities & social events. Located on the Chester River & Chesapeake Bay, you will be DAZZLED by the natural beauty of the area- -Of YOUR Community.... Literally a vacation without ever leaving town. Local medical facilities, shopping, restaurants & access to the DELMARVA beaches enhance the neighborhood's appeal, making it a wonderful place to call home. Experience the vibrant lifestyle and FRIENSHIPS & MEMORIES to be made in this exceptional community!

228 Bayberry Dr, Chester

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

$625,000
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!

208 Topside Dr Unit 211, Stevensville

Listing courtesy of Berkshire Hathaway Homeservice Homesale Realty. Contact:

$459,000
2 Beds ⋅ 2 Baths
Perfect location for an afternoon walk to the pool and clubhouse! New roof with a warranty that conveys with the purchase of this lovely home. The updated kitchen is one of the highlights with the light cherry cabinetry and Cambria Quartz counters, show off nicely against the mahogany flooring that extends thru out this home. Plantation shutters add character to the family room while the formal living and dining area reflect a more formal setting for entertaining. Owners suite in the rear of the home while a guest suite is in the front allows plenty of privacy for company or family. Enjoy relaxing outside on a large paver patio with a motorized retractable awning with new Sunbrella fabric. Overall, this is a lovely, well maintained home waiting for a new occupant to enjoy!   Symphony Village is a community of 395 houses, with mature trees, lush landscaping, and a magnificent clubhouse where myriad activities are available, including frequent social gatherings, holiday picnics, card games, mahjong, dance classes, billiards, a vibrant artisan group with  classes and shows, plus a quarterly reception for residents and friends to view the latest art creations. There are bocce courts, tennis and pickle ball courts, and a putting green with many keen players. The outdoor pool is open from May to September, and you can find several shady seating spots if you wish. The indoor heated pool is open year-round, and features a lift chair for those who need it. Water aerobics classes are offered weekdays indoors  or outdoors depending on the season.  Centreville is the Queen Anne County seat, with a historic courthouse, several restaurants, grocery stores, and other essential services. Easy drive to Easton, St. Michaels, Annapolis and Chestertown, and the beach is not too far away.

139 Harmony Way, Centreville

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

$749,000
4 Beds ⋅ 4 Baths
Experience the best of Kent Island living in this beautifully maintained coastal home, ideally situated in the highly desirable Water's Edge section of Gibson's Grant. Built in 2017, this exceptional residence enjoys unobstructed pond views from the welcoming covered front porch, where you can relax while watching blue herons and other native wildlife. Perfectly positioned just one block from the community's exceptional waterfront amenities, including the Chester River, clubhouse, pool, fitness center, kayak launch, fishing pier, and waterfront pavilion, this home offers the perfect blend of luxury, convenience, and the relaxed lifestyle of Maryland's Eastern Shore. Step inside to discover a bright, thoughtfully designed floor plan where beautiful flooring flows throughout the main level and abundant natural light fills every room. Designed for both everyday living and effortless entertaining, the main level offers exceptional versatility with a spacious flex room that is ideal as a home office, den, sitting room, or additional living space, along with a convenient powder room for guests. The heart of the home is the expansive open-concept living area, where the spacious family room, dining area, and beautifully appointed kitchen come together seamlessly. The kitchen features a large center island with abundant seating and workspace, while the family room is highlighted by a beautiful gas fireplace. Just beyond, the brand-new screened porch opens to your own private backyard oasis featuring a beautifully landscaped paver patio, a tranquil ornamental pond with a cascading waterfall, full privacy fencing perfect for pets, and an irrigation system to keep the grounds looking their best. Designed for the ease of first-floor living, the main level features a spacious primary suite privately situated at the rear of the home. The luxurious ensuite bath includes a relaxing Jacuzzi soaking tub, while a second main-level bedroom offers its own private full bath, making it ideal for guests or multigenerational living. The staircase to the upper level is thoughtfully tucked toward the rear of the home, enhancing the home's functional layout. Upstairs, you'll find two generously sized bedrooms and a beautifully appointed full bath, providing comfortable accommodations for family and guests. Completing the home is a spacious rear-entry two-car garage with plenty of room for parking and storage, plus a custom-built workspace perfect for DIY enthusiasts, hobbyists, or woodworking projects. An approximately four-foot-high conditioned crawl space with interior access provides exceptional additional storage. Recent improvements include a brand-new HVAC system, brand-new screened porch, one-year-old oven, and new washer and dryer, allowing you to move in with confidence. Residents of Gibson's Grant enjoy resort-style amenities, including a clubhouse, outdoor pool, fitness center, waterfront pavilion, kayak launch, fishing pier, water access, and direct access to the Cross Island Trail. Tucked behind a peaceful nature preserve just off Route 50, this sought-after waterfront community offers the perfect balance of tranquility and convenience. Located just moments from the Chesapeake Bay Bridge, the home provides an easy commute while placing you minutes from waterfront dining, marinas, shopping, parks, and local entertainment. Beautifully maintained, thoughtfully updated, and ideally located in one of Kent Island's most desirable neighborhoods, this exceptional home offers the perfect opportunity to embrace luxury coastal living on Maryland's Eastern Shore. Schedule your private showing today! Mortgage savings may be available for buyers of this listing.

134 Richard Ingle Way, Chester

Listing courtesy of Redfin Corp. Contact:

$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:

$595,000
2 Beds ⋅ 3 Baths
Beautiful fourth-floor condo offering nearly 2,000 square feet of living space, featuring two bedrooms, a home office, two full baths, and a half bath. Enjoy morning sun from the oversized porch, a spacious living room, and an open-concept layout designed for comfort and entertainment. Highlights include luxury flooring, a fireplace, and a beautifully appointed kitchen with an oversized center island and quartz countertops stainless steel appliances and much more. This unit also includes a one-car garage and private storage space. The community offers unparalleled amenities and gorgeous water views, creating the perfect Chesapeake Bay lifestyle. Enjoy walking trails, outdoor tennis courts, indoor and outdoor pools, and a 23,000-square-foot clubhouse with outdoor spaces, a ballroom, test kitchen, outdoor bar, and community pier, views of the Chester River.

1000 Herons Nest Way Unit 43, Chester

Listing courtesy of Coldwell Banker Realty. Contact:

$575,000
3 Beds ⋅ 3 Baths
*BIG PRICE IMPROVEMENT ON THIS BEAUTY* SELLER IS ALSO OFFERING CLOSING ASSISTANCE!Welcome to Bay Bridge Cove, an active adult 55+ community designed for comfort, convenience, and low-maintenance living. Residents enjoy exceptional amenities including a clubhouse with outdoor pool, fitness center, lounge, library, meeting space, and game room, along with walking trails, scenic ponds, pickleball and bocce courts, a crab shack, and community vegetable and herb gardens. Ideally located near Historic Annapolis, shopping, dining, recreation, and major commuter routes including Rt. 50, Rt. 97, the Bay Bridge, Washington, D.C., Baltimore, and the Eastern Shore. This beautifully upgraded Easton model by award-winning McKee Builders offers quality craftsmanship, energy efficiency, and thoughtful design throughout. A private gated paver courtyard creates a warm welcome, while the spacious rear deck overlooks open green space and mature trees for a peaceful outdoor setting. Inside, this meticulously maintained home offers approximately 2,000 square feet with 3 bedrooms, 3 full baths, a versatile loft, and a 2-car garage. The gourmet kitchen is appointed with upgraded cabinetry featuring pull-out shelving and soft-close doors and drawers, granite countertops, decorative backsplash, Kohler undermount stainless sink, and upgraded stainless steel appliances. Additional improvements include upgraded flooring, renovated baths, and a tankless on-demand water heater. The open and airy interior is filled with natural light from two skylights in the main living area. Architectural details include crown molding, chair rail accents, soaring foyer ceilings, cathedral ceilings in the dining and family rooms, and a tray ceiling in the primary suite. The spacious primary retreat includes two closets and a beautifully updated bath. Two additional bedrooms and two full baths, with one bedroom and bath on each level, offer flexibility for guests or multigenerational living. The loft provides ideal space for a home office, den, or reading area. A large conditioned crawl space with interior access offers excellent storage. Please note: public records do not reflect the correct square footage. Approximate finished living area is 2,000 square feet. CALL ME TODAY FOR YOUR SHOWING!

324 Moorings Cir Unit 108, Stevensville

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

$299,900
3 Beds ⋅ 3 Baths
Motivated Seller now offering $5,000 closing help! This home is move in ready. Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring elegant quartz countertops—perfect for everyday living, relaxing weekends, and entertaining family and friends. Natural light fills the living spaces, while the seamless flow between the kitchen, dining, and living areas creates a warm and welcoming atmosphere throughout the home. Step outside to enjoy your private screened porch—ideal for morning coffee or evening unwinding—or host summer gatherings on the private patio designed for grilling and outdoor entertaining. Rare opportunities like this don’t come along often in Queen’s Landing, especially with the combination of three bedrooms, modern updates, and exceptional outdoor living spaces. Enjoy a true resort-style lifestyle with community amenities that include a swimming pool, fitness center, pickleball and tennis courts, and a private marina. Whether you’re looking for a full-time residence, weekend retreat, or low-maintenance coastal lifestyle, this home offers the perfect balance of relaxation and convenience. Ideally located in the heart of Chester, you are just minutes from waterfront dining, shopping, entertainment, and major commuter routes—making it easy to enjoy everything the Eastern Shore has to offer while staying connected to Annapolis, Baltimore, and Washington, D.C. Some photos are for illustrative purposes only.

54 Queen Caroline Ct, Chester

Listing courtesy of Island Realty, LLC. Contact:

$485,000
2 Beds ⋅ 3 Baths
BACK on the MARKET. GREAT OPPORTUNITY at THIS PRICE. This Chester model has scenic, seasonal views of Macum Creek, beautiful sunrises, and an incredible display of wildlife in all seasons. Easy walk to Kayak launch and creek. With nearly 2000 square feet of open living space this home has a great layout for entertaining family and friends. The spacious great room, adjacent to the dining area and kitchen, provide an open area for gatherings. The gourmet kitchen is equipped with upgrades from the stunning kitchen island with quartz counter tops, beautiful upgraded cabinetry to the GE Profile appliances. This kitchen is designed for everyday living as well as hosting the occasional dinner party. The primary bedroom, is a separate self-contained suite complete with two closets and a luxury owners' bath that includes double sinks, and quartz countertops. The bright and airy 2nd bedroom is also a separate suite with a full bath and an oversized walk-in closet. In addition to the two bedrooms, there is a home office with stylish French Doors and a powder room for guests. The separate laundry room is equipped with a GE washer and dryer. This home also has a garage with adjoining driveway/parking space and large personal storage room which is a few short steps from the elevator. This home is just a short walk to resident kayak racks with launch access to the Chester River. KEEP IN MIND THIS CHESTER MODEL, WITH PLENTY OF FEATURES AND UPGRADES INCLUDED, IS MOVE-IN READY AND PRICED TO SELL***** Award-winning 24,000 Square Foot Clubhouse with Stunning Chester River Views! Fantastic amenities include 4.3 miles of walking trails throughout the community, outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, gas and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, lighted pickle ball courts, tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

1000 Herons Nest Way Unit 22, Chester

Listing courtesy of RE/MAX Executive. Contact:

$375,000
2 Beds ⋅ 3 Baths
*100% Renovated* Welcome to this *BEAUTIFUL RENOVATED* 2-bedroom, 2.5-bath townhome nestled in a desirable condo community on Kent Island. This fully updated home shines with thoughtful upgrades and modern touches throughout — including new storm doors, 2025 heat pump, new water heater, upgraded electrical system, new blinds, a new Samsung washer and dryer, double-pane windows, and brand-new carpet on the stairs and upper level. The open-concept main floor flows effortlessly to a private outdoor deck, perfect for morning coffee or evening entertaining with a tranquil view. Upstairs, the spacious primary suite features its own private balcony overlooking Thompson Creek, creating a peaceful personal retreat. The second bedroom and beautifully renovated bathrooms provide a flexible living space for guests and family. Enjoy serene water views, a quiet and walkable neighborhood, and easy access to scenic community walking trails. Whether you’re savoring the outdoors or relaxing amid a fully renovated, stylish interior, this move-in-ready townhome perfectly blends comfort, convenience, and the best of Kent Island living. PLEASE REMOVE SHOES...THANK YOU.

1205 Marion Quimby Dr, Stevensville

Listing courtesy of Taylor Properties. Contact: