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Sean Monahan
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Chester MD Real Estate & Homes for Sale

66 Properties Found

The median home value in Chester, MD is $499,000. This is higher than the county median home value of $395,500. The national median home value is $308,980. The average price of homes sold in Chester, MD is $499,000. Approximately 71% of Chester homes are owned, compared to 19% rented, while 10% are vacant. Chester real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chester real estate agent to arrange a tour today!
Learn more about Chester Real Estate.


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Beds:
3
Baths:
3.00
Sq.Ft.:
1,302
Status:
NEW LISTING
MLS#:
MDQA2017340
Type:
Townhouse
Subdivision:
BRIDGEPOINTE
Year built:
1993
Courtesy: Rosendale Realty
View additional info
Beds:
3
Baths:
2.00
Sq.Ft.:
1,160
Status:
NEW LISTING
MLS#:
MDQA2017080
Type:
Single Family
Subdivision:
CHESTER
Lot size:
0.16 Acres
Year built:
1961
Courtesy: Thurston Wyatt Real Estate, LLC
View additional info

You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying opportunity. Property is owned by the US Dept. of HUD. All HUD Homes are sold AS-IS . This property is HUD Case # 244-032645. Information and Disclosures available at hudhomestore website. property Insurability code is: IE. Bids may only be submitted by HUD Registered Agents/Agencies. Buyers are responsible for Dewints/Rewints coordination/expenses. LBP (Lead-Based Paint) may be present. Seller makes no representations or warranties as to property condition.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,119
Status:
NEW LISTING
MLS#:
MDQA2017258
Type:
Single Family
Subdivision:
GIBSONS GRANT
Lot size:
0.08 Acres
Year built:
2016
Courtesy: Samson Properties
View additional info

Welcome to 265 Evelyne Street in the sought-after waterfront community of Gibsons Grant! Offering nearly 2,200 square feet of living space, this beautifully maintained home combines coastal charm with modern comfort. Inside, you'll find hardwood floors, a spacious open-concept layout, and a beautifully appointed kitchen featuring a large island, gas stove, double oven, and plenty of space for gathering and entertaining. The flexible floor plan includes a spacious family room above the two-car garage - perfect for a media room, playroom, home office, or guest retreat. The primary suite offers a relaxing escape with a double vanity, soaking tub, and walk-in shower. Additional highlights include a Rinnai tankless hot water heater, welcoming front porch, and thoughtful upgrades throughout. Enjoy all that Gibsons Grant has to offer, including a community pool, clubhouse, fitness center, kayak launch, walking trails, playgrounds, waterfront access, and scenic open spaces - all conveniently located just minutes from the Bay Bridge, shopping, dining, and everything Kent Island has to offer. Coastal living at its best!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,789
Status:
NEW LISTING
MLS#:
MDQA2017256
Type:
Single Family
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.16 Acres
Year built:
2026
Courtesy: KOVO Realty
View additional info

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened patio extends the living area outdoors - perfect for entertaining or relaxing. The kitchen is equipped for both style and performance, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner's bath for a cohesive, elegant finish. Hardwood flooring flows throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, bedrooms 2, the primary suite, loft, and second floor, while tile is featured in all full baths and the laundry room. The primary bath includes a walk-in shower with seat and handheld shower wand and a double-sink vanity for added convenience and luxury. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Beds:
4
Baths:
5.00
Sq.Ft.:
4,717
Status:
NEW LISTING
MLS#:
MDQA2017210
Type:
Single Family
Subdivision:
SOUTHWIND
Lot size:
2.3 Acres
Year built:
1997
A broker reciprocity listing Courtesy: Coldwell Banker Realty
View additional info

Sited on Cox Creek with 369 feet of waterfront, this elegant contemporary residence offers 2.3 private acres, spectacular western exposure, and breathtaking sunset views. Thoughtfully designed to maximize water vistas from nearly every room, the home features 4 bedrooms, 3 full baths and 2 half baths, and approximately 4,717 square feet of refined living space. The gourmet kitchen is appointed with rich custom cabinetry, granite countertops, upgraded stainless steel appliances, and a gas cooktop, creating an ideal setting for both everyday living and entertaining. Custom hardwood flooring spans the main level, complemented by two fireplaces and timeless architectural details throughout. The luxurious main-level primary suite offers serene water views, multiple walk-in closets, and a recently renovated spa-inspired bath. A beautiful three-season room overlooks the creek, providing the perfect space to relax and enjoy the tranquil setting. There is also ample room to add a pool. Upstairs, three additional bedrooms and two full baths provide comfortable accommodations for family and guests, with three of the four bedrooms enjoying water views. The upper level has been recently updated with luxury vinyl plank flooring in place of carpet. Additional highlights include mature professional landscaping, a temperature-controlled wine room, a 3-car garage, a new roof, private pier with electric and water, boat lift, jet ski lifts, and riprap shoreline protection. Located in the desirable Southwind community, residents enjoy amenities including a boat launch, boat storage area, tennis courts, walking trails, and a clubhouse - all conveniently located near shopping, dining, and more.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
NEW LISTING
MLS#:
MDQA2017086
Type:
Condo
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2023
A broker reciprocity listing Courtesy: Coldwell Banker Realty
View additional info

Built for low-maintenance living, this beautiful 3-bedroom, 2.5-bath condo offers 2,600 square feet of comfort, space, and resort-style amenities. The open living, dining, and kitchen layout is ideal for everyday living and entertaining. Enjoy peaceful views of three ponds from the beautiful porch, with limited views of the Chester River. The kitchen features 42-inch cabinets, white quartz countertops with gray veining, and a neutral color palette ready for your personal style. The spacious primary suite is privately situated on one side of the condo and includes an owner's sitting room. Each bedroom offers a walk-in closet. Located in the desirable Four Seasons community, residents enjoy tennis courts, playgrounds, indoor and outdoor pools, fire pits, a pier, bars with TVs, gathering rooms in each building, a 22,000-square-foot clubhouse, fitness spaces, entertaining areas, a kayak park with launch, water access, and more.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,639
Status:
NEW LISTING
MLS#:
MDQA2017202
Type:
Condo
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2023
A broker reciprocity listing Courtesy: The KW Collective
View additional info

Impeccably finished and immediately available, this corner residence provides the ease and comfort of luxury condo living surrounded by the natural beauty of the Chesapeake Bay landscape. Windows on three sides fill more than 2600 square feet with natural light, while the peaceful pond-to-river setting creates a backdrop of fountains, wildlife, and winter water views beyond. Secure building access and elevator service lead to the unit level, where a residents-only club room provides additional gathering space just steps from the home. Inside, wide-plank luxury vinyl flooring, decorator-selected paint colors, and plantation shutters throughout reflect the care and attention given to making this home feel welcoming, polished, and customized far beyond typical builder-grade finishes. The well-appointed kitchen features crisp white cabinetry, white quartz countertops, under-cabinet lighting, stainless steel appliances, gas cooking, and a seamless 8-foot island with breakfast bar seating for up to eight. A separate beverage center adds additional serving and storage space between the kitchen and dining area. The open floorplan extends to the spacious living and dining areas, anchored by crown molding, upgraded lighting, and a stacked stone fireplace with French sliders leading to the balcony with a peaceful, private view of the immaculately kept landscape and tree-lined shore. Privately positioned at the rear of the residence, the oversized primary suite includes a separate sitting room with balcony access, two large walk-in closets, and a spacious spa-style bath with dual vanities, step-in shower, private water closet, and generous storage. Bedrooms two and three each include two walk-in closets and share a Jack-and-Jill bath with dual vanities and tub shower. Four additional closets, a powder room, a large laundry room with built-ins, a climate controlled storage room on the garage level, an attached one-car garage, and keyless entry to the unit and garage make day-to-day living feel remarkably effortless, organized, and secure. The Four Seasons at Kent Island lifestyle centers around resort-style amenities, waterfront living, outdoor recreation, and community gatherings that make this one of the Eastern Shore's most active 55+ communities. Residents enjoy a 24,000 square foot waterfront clubhouse with indoor heated pool and spa, fitness center, lounge, ballroom, library, gathering spaces, and an outdoor beach-entry pool and lounge overlooking the Chester River. Outdoor amenities include pickleball, tennis, basketball, and bocce courts, walking and biking trails, kayak and paddleboard launch and storage, a fishing pier and boat dock, dog park, beachy fire pits, tiki bar, and a waterfront amphitheater for concerts and events. A full-time activities director coordinates clubs, fitness classes, social events, and community celebrations throughout the year. All of this is moments from the Cross Island Trail, Kent Narrows waterfront dining and marinas, and easy access to Annapolis, Baltimore, Washington, and the Eastern Shore. Easy living, thoughtful entertaining, and everyday connection to the Chesapeake waterfront come together in a home designed for comfort without compromise. More photos and videos are available at the virtual tour link.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,312
Status:
NEW LISTING
MLS#:
MDQA2017164
Type:
Condo
Subdivision:
QUEENS LANDING
Year built:
1995
Courtesy: Coldwell Banker Realty
View additional info

This charming townhouse in Queens Landing offers a perfect blend of comfort and community amenities. Step inside to discover a traditional floor plan featuring a cozy living room off the eat-in kitchen, with a separate family room ideal for gatherings. The home boasts two spacious bedrooms and 2.5 baths, including a primary bath for added convenience. Updates include new flooring throughout; LED lighting, granite counters, newer windows and HVAC system. Enjoy modern amenities with a suite of appliances, including a built-in microwave, dishwasher, electric range, washer and dryer. Outside, the community shines with well-maintained sidewalks, streetlights, and a variety of recreational facilities. Take advantage of the clubhouse, outdoor pool, tennis courts, and scenic waterfront jogging paths. The nearby Chester River provides a serene backdrop for leisurely strolls and outdoor activities, with access to the Cross Island Trail connecting waterfront features at Terrapin Park and The Narrows. Located within a vibrant neighborhood, residents benefit from access to parks and essential public services. This home is not just a place to live; it's a gateway to a fulfilling lifestyle in a welcoming community. Some photos displayed used AI and may not be 100% accurate. Please schedule an in-person tour to view this beautiful property.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
MDQA2017146
Type:
Condo
Subdivision:
QUEENS LANDING
Year built:
1998
Courtesy: Island Realty, LLC
View additional info

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
MDQA2017082
Type:
Condo
Subdivision:
QUEENS LANDING
Year built:
1998
A broker reciprocity listing Courtesy: Long & Foster Real Estate, Inc.
View additional info

Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters, and backsplash, 3 new bathrooms, all new flooring throughout, new washer and dryer and freshly painted. Nestled in the serene enclave of Queens Landing, this exquisite remodeled in 2026 Colonial townhouse offers a harmonious blend of luxury and comfort. Spanning 1,440 square feet, the open floor plan invites you to experience a seamless flow between the combination dining and living areas, perfect for both intimate gatherings and entertaining. The family room, conveniently located off the kitchen, creates a warm atmosphere where cherished memories are made. Indulge in the elegance of three spacious bedrooms all on the same level and two and a half beautifully recently remodeled bathrooms, designed for relaxation and rejuvenation. The inviting ambiance is enhanced by the cozy fireplace, providing a perfect backdrop for cozy evenings at home. Step outside to discover the community's stunning outdoor pool, where you can unwind under the sun or enjoy leisurely afternoons by the water. With direct access to the Chester River, water enthusiasts will appreciate the navigable waters, ideal for kayaking or simply soaking in the tranquil views. Queens Landing boasts an array of amenities, including a clubhouse, exercise room, and scenic bike trails, fostering an active and vibrant lifestyle. The meticulously maintained common grounds offer a picturesque setting for leisurely strolls or social gatherings. This property is not just a home; it's a lifestyle choice that embodies luxury, comfort, and community. Experience the best of waterfront living in this exceptional residence, where every detail has been thoughtfully curated for your enjoyment. Schedule your tour today!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,276
Status:
Active
MLS#:
MDQA2017106
Type:
Single Family
Subdivision:
GIBSONS GRANT
Lot size:
0.17 Acres
Year built:
2011
Courtesy: Samson Properties
View additional info

Welcome to 126 Claiborne Street in the sought-after Gibson's Grant community on Kent Island - a beautifully crafted Covell-built Sawgrass model offering the perfect blend of coastal charm and comfortable with peaceful pond and park views right outside your door This thoughtfully designed home features 3 bedrooms, 2.5 baths, and a desirable main-level primary suite complete with a private en suite bath for easy everyday living. The heart of the home is the updated kitchen, showcasing quartz countertops, stainless steel appliances, and timeless hardwood floors that continue throughout the main living spaces. Upstairs, you'll find two additional bedrooms, a full bath, and a spacious rec room that provides the perfect second living area, home office, or guest retreat. Enjoy outdoor living with a covered front porch, a screened porch for relaxing evenings, and an additional open porch overlooking the fenced side yard - ideal for entertaining or enjoying the peaceful surroundings. A rear-entry 2-car garage adds both convenience and curb appeal. Residents of Gibson's Grant enjoy exceptional resort-style amenities, including a community pool, clubhouse, fitness center, kayak launch, fishing and crabbing pier, waterfront pavilion, and direct access to the Cross Island Trail - all just minutes from the dining, marinas, and attractions of Kent Narrows.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,804
Status:
Active
MLS#:
MDQA2017062
Type:
Single Family
Subdivision:
HARBOR VIEW
Lot size:
0.27 Acres
Year built:
1992
Courtesy: EXP Realty, LLC
View additional info

Don't miss this charming Cape Cod-style home in the highly desirable Harbor View neighborhood of Chester. Thoughtfully designed and move-in ready, this home offers the perfect blend of comfort, style, and functionality. The main level features luxury vinyl plank flooring and a bright, open-concept layout ideal for everyday living and entertaining. The spacious kitchen boasts granite countertops, a center island, and ample cabinetry, flowing seamlessly into the dining area and inviting family room with a cozy fireplace. A main level bedroom and full bath provide flexible living options, while an additional versatile space can serve as a home office, gym, or potential fourth bedroom. Upstairs, you'll find two generously sized bedrooms, including one with direct access to the hall full bath. Situated on a large, fenced rear yard, the outdoor space is perfect for relaxing or entertaining, complete with a spacious deck and a storage shed for added convenience. Located across from a large vacant lot, the home enjoys an added sense of privacy. Centrally located and truly turnkey, this home offers easy living in a sought-after community. Don't miss your opportunity to make it yours!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,791
Status:
Active
MLS#:
MDQA2017038
Type:
Single Family
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.16 Acres
Year built:
2026
Courtesy: KOVO Realty
View additional info

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. This home combines thoughtful design with comfortable living spaces ideal for both everyday life and entertaining. The main living area features a cozy one-story fireplace, creating a warm and inviting focal point. A dedicated home office provides a private space for work or study, while the screened patio extends your living area outdoors - perfect for relaxing or hosting guests. The kitchen is designed for both style and function, featuring a single oven, microwave, gas cooktop with range hood, dishwasher, French door refrigerator, pendant lighting, tile backsplash, and quartz countertops. Quartz is also featured in the owner's bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, kitchen, dining area, great room, bedroom 2, owner's suite, HovHall, loft/second floor, and bedrooms 3 and 4. Tile flooring is featured in all full baths and the laundry room. The owner's bath includes a walk-in shower with a seat and handheld shower wand, along with a double-sink vanity for added comfort and convenience. For a full list of features for this home please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,839
Status:
Active
MLS#:
MDQA2017004
Type:
Townhouse
Subdivision:
GIBSONS GRANT
Lot size:
0.08 Acres
Year built:
2017
Courtesy: Coldwell Banker Realty
View additional info

Welcome home to this beautifully maintained three-bedroom, two-and-a-half-bath home in the sought-after waterfront community of Gibson's Grant, where lifestyle and a prime Kent Island location come together effortlessly. A welcoming front porch sets the tone, leading into an open-concept main level designed for both everyday living and entertaining. The spacious living room with propane fireplace flows seamlessly into the dining area and kitchen featuring stainless steel appliances, propane stove with double oven, granite countertops, and ample cabinetry. Rich wood flooring extends throughout the main level, adding warmth and continuity. Just inside off the one-car garage, you'll find a convenient powder room and two additional storage closets. Step outside to a fenced brick paver patio just off the kitchen, an ideal setting for outdoor dining, gardening, or simply relaxing in a private, low-maintenance space. Upstairs, the primary suite offers a peaceful retreat with walk-in closets complete with built-ins and a spacious en suite bath featuring a large jetted tub, double vanities, shower, and a private water closet. Two additional bedrooms, a full bathroom with double sinks, and a dedicated laundry area complete the second level. Additional highlights include a one-car garage with built-in storage and a generous parking pad accessible from the rear alley. Enjoy all that Gibson's Grant has to offer, including a nearby community pier with grills, fire pits, and covered seating - perfect for waterfront evenings and neighborhood gatherings. Just down the street, you'll find access to the community small craft launch/storage area and direct access to the scenic Cross Island Trail, while community amenities such as the clubhouse, fitness center, pool, playground, and bocce court provide a resort-style living experience year-round. This is coastal community living at its finest - thoughtfully designed, beautifully maintained, and ideally located off Route 50 for quick access to Annapolis, Washington DC, Baltimore, Saint Michaels, and beyond.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,016
Status:
Active
MLS#:
MDQA2017056
Type:
Single Family
Subdivision:
HARBOR VIEW
Lot size:
0.35 Acres
Year built:
1973
A broker reciprocity listing Courtesy: RE/MAX Executive
View additional info

Spacious and beautifully updated ranch-style home offering over 2,000 square feet of comfortable one-level living. This versatile layout features 3 bedrooms and 2 full baths, including a large bonus room that can easily function as a fourth bedroom, home office, or second living area. A welcoming front porch sets the tone, while the screened back porch provides the perfect space to relax or entertain. The renovated kitchen (2018) is a standout with gorgeous quartz countertops, a large center island, and more recently updated appliances. Lots of updates in 2022 include HVAC, hot water heater , washer and dryer. The roof, siding, windows and floors were completed in 2018. Situated on a large, level lot, the outdoor space offers a fire pit and a dedicated vegetable and herb garden perfect for enjoying time outside. Located on a quiet, dead-end street with a serene setting, this home is just steps from the community park and ideally positioned to enjoy nearby boating, kayaking, and a variety of water sports, along with some of the area's best waterfront dining and shopping. Move-in ready with major updates already completed, this home offers space, flexibility, and a lifestyle that is easy to love. Harbor View is a residential community of 450 homes located on Cox Creek two miles east of the Chesapeake Bay Bridge. Easy commute to Annapolis (20 min), Baltimore (45 min) and Washington D.C. (50 min to 1 hr). With just a few steps out your door you can be at the Kent Narrows for local food, Cross Island Trail for a walk and run or head five minutes east to Queenstown and shop at the Prime Outlets. Harbor View offers five miles of neighborhood roads for casual biking, walking and running, a one acre field with a pavilion and playground for our community events and your enjoyment. Each year the community comes together for an Easter Egg Hunt, Community Picnic and two yard sales.

Beds:
3
Baths:
5.00
Sq.Ft.:
4,208
Status:
Active
MLS#:
MDQA2016982
Type:
Single Family
Subdivision:
HARBOR VIEW
Lot size:
0.35 Acres
Year built:
2006
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Escape the ordinary in this one-of-a-kind waterfront masterpiece on Cox Creek. Designed for those who refuse to settle for "cookie-cutter," this residence seamlessly blends sophisticated daily living with an unparalleled entertaining layout. The ground-level "Party Zone" is a showstopper, featuring a full bar and lounge with dual garage doors that open directly to a private oasis complete with a pool, hot tub, and patio. Just steps away, your private dock awaits, equipped with two boat lifts, water, and electric. Inside, the craftsmanship shines through extensive custom built-ins and exquisite trim work. The heart of the home is the chef's kitchen, recently remodeled with stunning Taj Mahal Quartzite, marble backsplash, and a hidden wine cellar. The top-floor primary retreat is a destination of its own, boasting a private viewing deck, a spa-like bath with a rain shower/jetted tub, a massive custom closet, and a dedicated morning bar (fridge/microwave/laundry) for ultimate convenience. With two additional ensuite guest suites and a flexible loft space, this home offers luxury at every turn. Live the life you've imagined - schedule your private tour today.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,353
Status:
Active
MLS#:
MDQA2016936
Type:
Single Family
Subdivision:
FOUR SEASONS AT KENT ISLAND
Lot size:
0.14 Acres
Year built:
2025
Courtesy: Samson Properties
View additional info

Welcome to luxury coastal living in the highly desirable Four Seasons at Kent Island 55+ community in Chester. Built in 2025, this practically new home offers the perfect blend of elegance, comfort, and convenience - without the wait for new construction. Ideally situated on coveted Kingfisher Lane, this exceptional Tuscaloosa model offers over 3,200 square feet of beautifully designed living space with 5 bedrooms and 4.5 baths. The upgraded stone-and-shake exterior creates stunning curb appeal, while the covered front porch offers peaceful peek-a-boo water views - the perfect place to enjoy your morning coffee at sunrise. Inside, the open-concept main level showcases a thoughtfully upgraded interior with classic cabinetry, glass display cabinets, and professional-grade GE Caf appliances in the kitchen. The spacious living area is anchored by a dramatic stone gas fireplace, while custom wall detailing and molding upgrades in the foyer and primary suite add warmth and sophistication throughout the home. Norman shutters on every window, upgraded carpet with premium padding, and carefully selected finishes elevate every room. The main-level primary suite offers a private retreat with elegant trim details and a spa-inspired en suite bath featuring a luxurious soaking tub designed for relaxation. Additional upgrades include a screened porch for outdoor enjoyment, epoxy garage flooring, painted garage walls, and a dedicated EV charging station for modern convenience. Located just a short distance from the community dog park, playground, pickleball and tennis courts, and the state-of-the-art clubhouse, this home offers not only exceptional design but also an unmatched lifestyle. Residents of Four Seasons at Kent Island enjoy resort-style amenities including indoor and outdoor pools, a fitness center, walking trails, social spaces, and activities designed to support an active and vibrant coastal lifestyle. All of this is ideally located just minutes from the Chesapeake Bay Bridge, offering convenient access to Washington and Baltimore, while also being close to shopping at the Queenstown Premium Outlets and an array of local waterfront dining and everyday conveniences.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2016914
Type:
Condo
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2026
Courtesy: KOVO Realty
View additional info

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

Beds:
2
Baths:
3.00
Sq.Ft.:
1,425
Status:
Active
MLS#:
MDQA2016898
Type:
Condo
Subdivision:
QUEENS LANDING
Year built:
1999
Courtesy: Jorge A. Zea
View additional info

Experience "Paradise" in Queen's Landing. This rare, end-unit waterfront gem offers an unparalleled living experience overlooking the serene Lake Amleto. Boasting a 2019 full-gut renovation by a custom contractor, this 1,425 sq. ft. residence (including a 145 sq. ft. sunroom) blends sophisticated design with resort-style tranquility. The interior showcases master-level craftsmanship: solid hickory wood floors, custom solid wood doors, custom maple cabinetry with ingenious storage solutions (toe-kick and spice & utensil drawers), and Calacatta Gold marble adorning both the kitchen and the gas fireplace surround. The open floor plan is optimized with structural improvements, including a pantry with a pocket door, a custom staircase with integrated storage, and a hidden Murphy door. Extensive recessed lighting on main floor with 3 dimmable picture wall accent lighting. Luxury finishes abound, from Emtek brass hardware and crown molding in every room to Monogram premium appliances and custom window treatments with a hidden railing system. Both upper-level bedrooms feature ensuites and are private retreats; one features a Travertine shower and floor with antique bronze hardware, while the other offers elegant Italian tile. Relax year-round in the sunroom, constructed with heavy-duty UV-protected glass, to watch herons and waterfowl against a backdrop of lake fountains. A remote-controlled full patio width awning installed to control the amount of sunlight coming into the home. Modern peace of mind is provided by an under- warranty Carrier HVAC system (with humidifier/air cleaner), Homeguard water softener, and updated roof, windows, and stucco. The Queen's Landing lifestyle includes a renovated clubhouse, heated outdoor pool, fitness center, pickleball and tennis, racquetball, community marina, kayak launch and racks. Unique Opportunity: The owner is also offering a 70-foot deep-water boat slip for separate purchase - a rare find for the avid mariner. Features List: Renovation: Total gut-renovation (2019) including structural optimizations. Kitchen: Custom Maple cabinetry, Calacatta Gold Marble counter tops and backsplash, Monogram/Blomberg appliances. Mechanicals: Carrier HVAC w/ humidifier, Homeguard softener, LG HE Washer/Dryer. Extra insulation in the attic with insulated access cover. Sound proofing insulation between the first and second floor was added during the remodel. WellSys water dispenser: tied to home plumbing and includes cold and hot water. This is an optional rental unit and is contained within the kitchen cabinet. Exterior: New Roof (2021), New Stucco (2017), New Windows/Front Door (2017). Parking/Storage: Storage room off sunroom; ample community parking. Boating: 70' deep-water slip available.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,536
Status:
Active
MLS#:
MDQA2016908
Type:
Single Family
Subdivision:
WATERMAN'S COVE
Lot size:
0.24 Acres
Year built:
2020
Courtesy: Coldwell Banker Realty
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Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman's Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience. An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite deck, built by Lundberg Builders, perfect for relaxing or entertaining. The home sits adjacent to community open space, offering added privacy with no direct neighbor next door. Inside, you'll find hardwood flooring and an open-concept layout designed for modern living. The living room flows seamlessly into the dining area and kitchen, which features granite countertops, stainless steel appliances, and a beautiful tile backsplash. Sliding doors off the dining area lead to the composite deck and a lush, partially fenced yard, creating an ideal space for indoor-outdoor living. The kitchen also provides convenient interior access to the attached one-car garage. Upstairs, the primary suite offers a well-appointed bath, two additional bedrooms, a second full bath, and a laundry room for added convenience. Located just one mile from Route 50 on Cox Neck Road, this home offers quick access to shopping, dining, commuter routes to Washington DC and Baltimore, and the Chesapeake Bay Bridge. The intimate Waterman's Cove community consists of just nine homes, with HOA services that include lawn care and trash removal - making for easy, low-maintenance living. Enjoy the peaceful lifestyle of Maryland's Eastern Shore, with water views and privacy in a highly convenient location.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,069
Status:
Active
MLS#:
MDQA2016968
Type:
Condo
Subdivision:
BAYSIDE MARINA
Year built:
1999
Courtesy: Benson & Mangold, LLC
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Nestled in the charming Bayside Marina community, this 2nd floor condo offers a perfect blend of comfort and modern living. Built in 1999, this contemporary gem features an open floor plan that seamlessly connects the living with vaulted ceilings, dining, and kitchen areas, creating an inviting space for relaxation and entertaining. The kitchen boasts ENERGY STAR appliances, including a refrigerator and electric range, ensuring efficiency without sacrificing style. Enjoy cozy evenings by the gas fireplace, or unwind in the spacious primary suite with a walk-in closet and a luxurious bathroom featuring a tub shower. Step outside to discover beautifully maintained common grounds, complete with sidewalks and street lights that enhance the neighborhood's charm. The community amenities are a true highlight, offering a clubhouse, outdoor pool, exercise room, and pickleball courts for active lifestyles. Just a short stroll away, the serene Chester River awaits, perfect for leisurely walks or enjoying the calming sounds of water fountains. With convenient access to public services and a welcoming atmosphere, this home is not just a place to live, but a place to thrive. Cross trail path is just steps away, fine dining and casual dining waterside, fishing, crabbing and numerous water sports plus cultural activities just a short distance and 3 international airports minutes from Bayside. Experience the warmth and comfort of Bayside Marina-your new sanctuary awaits!

Beds:
3
Baths:
5.00
Sq.Ft.:
4,413
Status:
Active
MLS#:
MDQA2016942
Type:
Single Family
Subdivision:
SOUTHWIND
Lot size:
1.25 Acres
Year built:
1996
A broker reciprocity listing Courtesy: Wilson Realty & Staging LLC
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Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring upgraded countertops and a spacious island, flows seamlessly into the family room, perfect for entertaining. Relax in the primary suite with a lavish bath or unwind in the inviting family room by the fireplace with views out to Crab Alley. Three additional bedrooms (or two bedrooms and an office) and two baths round out the main level that offers sweeping scenic views from every vantage point. Step outside to discover a private oasis on 1.25 acres, complete with extensive hardscaping, a heated in-ground pool, and a soothing hot tub. Enjoy picturesque water views out the front and back, with access for kayaking and boating. The community amenities, including a beach, clubhouse, and tennis courts, elevate your living experience. This home is not just a residence; it's a lifestyle waiting to be embraced and enjoyed. Start living your best 'Shore Life' at 2855 Cox Neck Rd.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2016820
Type:
Condo
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2020
A broker reciprocity listing Courtesy: RE/MAX Executive
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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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2016714
Type:
Condo
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2024
A broker reciprocity listing Courtesy: Samson Properties
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A rare blend of coastal proximity and refined living unfolds within this beautifully appointed corner residence in the sought-after 55+ waterfront community of Four Seasons at Kent Island. Built in 2024 and impeccably maintained , this like-new residence offers the comfort of immediate enjoinment without the wait for new construction. Positioned near a tranquil creek leading to the Chesapeake Bay, the home offers a lifestyle deeply connected to the water without the demands of direct waterfront ownership. Sunlight fills the open-concept layout through the residence's desirable corner positioning, highlighting soaring ceilings, luxury vinyl plank flooring, and thoughtfully selected finishes throughout. The gourmet kitchen flows seamlessly into the dining and living areas, creating an inviting space for both quiet evenings and entertaining. Just beyond, a private balcony offers peaceful green surroundings with subtle water views, extending the home's living space into a serene outdoor setting. The spacious primary suite serves as a private retreat with walk-in closets and a beautifully finished en-suite bath, while two additional bedrooms provide flexibility for guests, hobbies, or a home office. Residents of Four Seasons at Kent Island enjoy access to resort-style amenities including indoor and outdoor pools, fitness center, clubhouse spaces, pickleball and tennis courts, scenic walking trails, kayak launch, and fishing pier. Conveniently located near Kent Narrows, Annapolis, and Route 50, this exceptional residence offers a refined Eastern Shore lifestyle with easy access to dining, recreation, and waterfront experiences.

Beds:
2
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2016724
Type:
Condo
Subdivision:
FOUR SEASONS AT KENT ISLAND
Year built:
2024
Courtesy: Coldwell Banker Realty
View additional info

Rare penthouse unit with year-round water views perfectly positioned to capture stunning sunrises every morning. This home has been owned and meticulously maintained by the original owner who spared no expense and opted for every builder upgrade that was offered, over $60,000.00 in options. The open concept design seamlessly connects the living room, dining area, and kitchen areas, all enhanced by expansive windows letting in an abundant amount of natural light. Experience resort style living in the highly sought after Four Seasons at Kent Island, a premier 55+ waterfront community. Residents enjoy access to world class amenities, including indoor and outdoor pools, walking trails, a Chester River pier. Ideally located just minutes from waterfront dining, shopping, and the Chesapeake Bay Bridge, this home offers the perfect blend of relaxation, convenience and low maintenance living at its finest. Additional interior photos coming soon!

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.

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