Chester MD Real Estate & Homes for Sale

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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
Courtesy: The KW Collective 443-574-1600
View additional info

ADDITIONAL INFORMATION

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 410-263-8686
View additional info

ADDITIONAL INFORMATION

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.:
1,400
Status:
NEW LISTING
MLS#:
MDQA2016050
Type:
Condo
Subdivision:
Dundee Harbor
Year built:
2003
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

OPEN House Sunday May 17, 9-11am! Welcome home to this Amazingly priced townhome on Kent Island! Square foot pricing like this is very rare to see on the Island! A 3-bedroom, 2.5-bath, 1400 sf. home in Dundee Harbor Condo Townhouse Association which offers the perfect blend of comfort and coastal living. Enjoy water privileges with access to Piney Creek Lake, including a private community pier ideal for fishing, kayaking, paddleboarding, and more. Just minutes away, Kent Narrows delivers the full waterfront lifestyle—dining, boat ramps, marinas, tiki bars, and endless local charm. Conveniently located near shopping, with easy access to Route 50 for commuting. This home is perfectly positioned for both relaxation and everyday living. Don’t miss the opportunity to embrace the Island Life! Stay Tuned- Coming Soon!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,486
Status:
NEW LISTING
MLS#:
MDQA2016514
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.69 Acres
Year built:
1961
Courtesy: Cross Street Realtors LLC 410-778-3779
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ADDITIONAL INFORMATION

Harbor View Community Corner Lot Renovated Rancher with Room to Grow If you’ve been searching for a home where the work is already done and you can move in without worrying about repairs or updates, this one deserves your attention. This fully renovated home in Harbor View offers exactly what so many first-time buyers are looking for—low maintenance living now, with room to grow later. One of the standout features is the rare double lot, giving you space that most homes simply don’t offer. Whether your future plans include a detached garage, pole barn, boat storage, or RV parking, you have the flexibility to make it happen without outgrowing your property. Inside, the layout is just as practical. With three bedrooms, two full baths, and two separate living areas, you have options—create a space for large gatherings, a playroom for children, or simply enjoy having separate areas for relaxing and entertaining. With so many updates, this is the kind of home that allows you to start smart—move in with confidence knowing major updates have already been completed, while still having the ability to build equity and expand over time. If your goal is to find a move-in ready first home with space, flexibility, and long-term potential, this is one you’ll want to see. The Harbor View community is known for its friendly setting and outdoor amenities. Residents enjoy five miles of walkable neighborhood roads for biking, jogging, or casual strolls, along with a community field, playground, and pavilion. Just two miles from the Chesapeake Bay Bridge, you’ll also have quick access to Kent Narrows, the Cross Island Trail, Queenstown Outlets, and local restaurants.

Beds:
7
Baths:
9.00
Sq.Ft.:
9,974
Status:
NEW LISTING
MLS#:
MDQA2016472
Type:
Single Family-Detached
Subdivision:
Serenity Farms
Lot size:
2.58 Acres
Year built:
2005
Courtesy: TTR Sotheby's International Realty 410-280-5600
View additional info

ADDITIONAL INFORMATION

Designed to rival a private resort, the outdoor spaces were made for celebrating with family and friends. Sweeping water views set the stage for unforgettable gatherings. The waterfront pool features a cascading natural rock waterfall with a bench tucked underneath and a generous shallow sun shelf. A beautifully appointed pool house offers a covered summer kitchen, bar, seating area and full bath with AC. A curated firepit lounge is perfect for evenings under the stars, while expansive patios, balconies and a waterside screened porch provide seamless indoor and outdoor living for every occasion. At the shoreline, life on the Chesapeake begins. The newly expanded L shaped pier is engineered for serious boating, with dockage for a large yacht, a 24,000 lb. and 10,000 lb. lift, electric, R/O water, dual pedestals and decorative lighting along all 260 feet. Protected waters offer calm conditions for docking, fishing, crabbing and watersports, with direct Bay access and easy cruising to Annapolis, St. Michaels and beyond. Modern convenience is seamlessly integrated through fully connected app based control of lighting, HVAC, security, pool, spa, generator, music, locks and network. Fiberoptic 2.5GB internet with seventeen access points ensures everyone stays connected. A whole house reverse osmosis water system serves the residence and dock. A 60KW whole house generator ensures peace of mind around the clock. Inside, the builder's own custom residence combines unsurpassed woodwork with seamless flow and uninterrupted water views throughout. The great room features a soaring wall of glass and fireplace. The chef's kitchen is appointed with Wolf and Sub Zero appliances, custom cabinetry, a fireplace, conversation bar, pantry and breakfast nook. The dining room seats 12 or more, ready for every holiday feast and dinner party. The primary suite is a private waterfront retreat with sitting area, fireplace, custom built ins and a spa bath with heated floors, soaking tub and multi jetted shower. The waterfront game room with fireplace, wet bar and large TV and the private theatre with a 100 inch screen and seating for 8 make this home the destination for family and friends. Upstairs, five architecturally unique bedrooms including three ensuite and a large activity room open to a deck overlooking the pool, dock, creek and bay. A fully equipped in law or guest suite features a separate entrance, kitchen, living area, bedroom, fireplace and attached two car garage. A separate four car garage with porcelain tile and custom cabinetry serves as studio, workshop and gym. Tucked along a quiet private road with easy access to the Bay Bridge, Annapolis and Washington D.C., this is waterfront vacation living designed to be experienced every day. Serenity Lane describes how you feel, not just where you are. Welcome Home!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,839
Status:
NEW LISTING
MLS#:
MDQA2017004
Type:
Single Family
Subdivision:
Gibsons Grant
Lot size:
0.08 Acres
Year built:
2017
Courtesy: Coldwell Banker Realty 410-263-8686
View additional info

ADDITIONAL INFORMATION

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:
3.00
Sq.Ft.:
2,602
Status:
NEW LISTING
MLS#:
MDQA2017086
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2023
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

Built for a low-maintenance lifestyle, this beautiful condo offers comfort, space, and resort-style amenities. Featuring 3 bedrooms, 2.5 baths, and 2,600 square feet, the home has an amazing layout with open living, dining, and kitchen areas perfect for entertaining. Enjoy a beautiful porch with peaceful views of three ponds and limited views of the Chester River. The kitchen features 42-inch cabinets and white quartz countertops with gray veining. The neutral color palette makes it easy to add your own style. The spacious primary suite is privately located on one side of the condo and includes an owner’s sitting room. Each bedroom offers a walk-in closet. The Four Seasons community offers incredible amenities, including tennis courts, playgrounds, indoor and outdoor pools, fire pits, a pier, bars with TVs, gathering rooms in each building, and a 22,000-square-foot clubhouse for fitness, entertaining, and relaxation.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,100
Status:
NEW LISTING
MLS#:
MDQA2016718
Type:
Condo
Subdivision:
Bayside
Year built:
1996
Courtesy: Long & Foster Real Estate, Inc. 410-263-3400
View additional info

ADDITIONAL INFORMATION

Just minutes over the Chesapeake Bay Bridge, this beautifully maintained end-unit townhome in Bayside offers the perfect Eastern Shore escape. Spectacular water views overlooking Castle Harbor Marina, the home features multiple decks, updated finishes, and, if you choose Castle Harbor Marina, easy access to your boat slip, only steps away. With approximately 2,100 square feet on three finished levels, highlights include a gourmet kitchen with granite counters, a center island with prep sink, gas cooking, double ovens, an expanded great room with fireplace and hardwood floors, a spacious primary suite with a deck and sitting area, and a versatile top level with a great room, living area that has plenty of room for bunk beds and more. Water views again from your picture window. Community amenities include a clubhouse, pool, tennis courts, and volleyball courts.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,440
Status:
NEW LISTING
MLS#:
MDQA2017082
Type:
Condo
Subdivision:
Queens Landing
Year built:
1998
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

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:
2.00
Sq.Ft.:
2,016
Status:
NEW LISTING
MLS#:
MDQA2017056
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.35 Acres
Year built:
1973
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

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:
4
Baths:
3.00
Sq.Ft.:
2,791
Status:
Active
MLS#:
MDQA2016506
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2026
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

Welcome to the Simone, a beautifully designed home offering 4 bedrooms, 3 baths, and a 2-car garage. Scheduled for settlement in July 2026, 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.:
2,789
Status:
Active
MLS#:
MDQA2016408
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2026
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. Scheduled for settlement in July 2026, 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:
3
Baths:
3.00
Sq.Ft.:
2,276
Status:
Active
MLS#:
MDQA2017106
Type:
Single Family-Detached
Subdivision:
Gibsons Grant
Lot size:
0.17 Acres
Year built:
2011
Courtesy: Samson Properties 703-378-8810
View additional info

ADDITIONAL INFORMATION

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:
5.00
Sq.Ft.:
4,208
Status:
Active
MLS#:
MDQA2016982
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.35 Acres
Year built:
2006
Courtesy: Chesapeake Real Estate Associates, LLC 410-476-2201
View additional info

ADDITIONAL INFORMATION

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.:
3,225
Status:
Active
MLS#:
MDQA2016404
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2026
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

Welcome to the Tuscaloosa, a spacious and thoughtfully designed home offering 5 bedrooms, 4.5 baths, and a 3-car garage. Scheduled for settlement in July 2026, this home delivers the perfect combination of comfort, functionality, and modern design. The main living area features a cozy fireplace with mantel and hearth, creating a warm focal point for gathering. A dedicated home office provides a quiet and productive workspace, while the screened patio extends the living area outdoors—perfect for relaxing or entertaining. Practical touches such as a utility sink add convenience to everyday living. The kitchen is designed 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 countertops are also featured in the primary bath for a cohesive and elegant finish. Luxury vinyl plank flooring runs throughout the foyer, extended foyer, HovHall, kitchen, dining area, great room, home office, extra suite, primary suite, and loft. Tile flooring is featured in the full baths and laundry room, while carpet provides comfort in bedrooms 3, 4, and 5. The primary bath offers a spa-like retreat with a freestanding tub, a walk-in shower with seat and handheld shower wand, and a double-sink vanity. 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:
5.00
Sq.Ft.:
4,413
Status:
Active
MLS#:
MDQA2016942
Type:
Single Family-Detached
Subdivision:
Southwind
Lot size:
1.25 Acres
Year built:
1996
Courtesy: Wilson Realty & Staging LLC 410-304-2250
View additional info

ADDITIONAL INFORMATION

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:
3
Baths:
2.00
Sq.Ft.:
1,804
Status:
Active
MLS#:
MDQA2017062
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.27 Acres
Year built:
1992
Courtesy: EXP Realty, LLC 888-860-7369
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ADDITIONAL INFORMATION

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:
3
Baths:
3.00
Sq.Ft.:
1,536
Status:
Active
MLS#:
MDQA2016908
Type:
Single Family-Detached
Subdivision:
Waterman's Cove
Lot size:
0.24 Acres
Year built:
2020
Courtesy: Coldwell Banker Realty 410-263-8686
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ADDITIONAL INFORMATION

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:
4
Baths:
3.00
Sq.Ft.:
2,791
Status:
Active
MLS#:
MDQA2017038
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2026
Courtesy: KOVO Realty 240-375-5074
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ADDITIONAL INFORMATION

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.:
2,000
Status:
Active
MLS#:
MDQA2017018
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.24 Acres
Year built:
2026
Courtesy: Coldwell Banker Waterman Realty 410-643-5005
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ADDITIONAL INFORMATION

Just completed brand new home! Energy efficient! The comfort of knowing that everything is new! One year warranty included! The fully finished daylight basement offers additional space for recreation or relaxation, enhancing the home's versatility. Composite deck, paved driveway, LVP flooring throughout, stainless steel appliances, and may other upgrades are found at this home. All you have to do is move in! There are no projects that need to be done except for putting your personal touch on making this new construction house, your home! Nestled in a vibrant neighborhood, residents enjoy easy access to local park/playground. Walk around the neighborhood and catch plenty of creek views as the community is situated on Cox Creek. This property features an attached garage and a gracious amount of off-street parking for convenience. Embrace the warmth and comfort of this exceptional home, where community spirit and modern living harmoniously blend.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,296
Status:
Active
MLS#:
MDQA2016754
Type:
Single Family-Detached
Subdivision:
Chester
Lot size:
0.28 Acres
Year built:
2017
Courtesy: Samson Properties 703-378-8810
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ADDITIONAL INFORMATION

Welcome to 200 Newtown Road, a charming home perfectly suited for those looking to enjoy Eastern Shore living. The inviting front porch offers the perfect spot to relax and unwind, while the screened porch provides additional space to enjoy the outdoors in comfort. Inside, you’ll find a generously sized kitchen with room for a table for six, ideal for everyday living and entertaining. A sliding door leads to the fenced backyard, offering both convenience and privacy. Enjoy peaceful water views and the freedom of no HOA restrictions. Located just around the corner from Public Landing, this home is perfect for those who love being on the water—bring your boat and take advantage of nearby access. With 3 bedrooms, 2.5 bathrooms, and a price of $445,000, this home offers an excellent opportunity to own near the water in a desirable location.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,800
Status:
Active
MLS#:
MDQA2017002
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.41 Acres
Year built:
1977
Courtesy: Century 21 Downtown 410-547-1116
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ADDITIONAL INFORMATION

Property is a combination of an Estate Sale (being sold As-Is) and a pre-approved short sale. 3Bd/2ba rancher on approximately .4 acres. Well and septic. Livrm, dinrm, famrm w/electric fireplace and kitchen. Off of the kitchen there is an enclosed room, concrete patio, and an additional screened-in patio. Backyard is partially fenced and has an in-ground pool (drained and in as-is condition) Convenient to Rte 50, Bay Bridge, and Annapolis. PR requests property be on the market for 7 days before reviewing any offer(s). PR and Asset Manager prefer using Gemini Title.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2016714
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2024
Courtesy: Samson Properties 240-630-8689
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ADDITIONAL INFORMATION

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:
3
Baths:
4.00
Sq.Ft.:
1,899
Status:
Active
MLS#:
MDQA2016002
Type:
Condo
Subdivision:
Bayside Marina
Year built:
1999
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

SO MUCH NEW HERE!! Welcome Home to this beautifully upgraded 4BR END UNIT Townhome with 2 full and 2 half baths, thoughtfully refreshed from top to bottom! Step inside to find the main level that boasts new carpet and new LVP flooring, a new half bath, new paint, a spacious laundry room and a large bedroom that could be used as another family room, toy/game room, den space, home office and more! Get ready to be wowed by the rich walnut stained hardwood flooring throughout the 2nd level where the living room, gas fireplace, new half bath and kitchen are located. The brand-new kitchen finishes are sure to please with new white quartz counter tops, new SS Appliances, fresh neutral paint and white cabinetry! Upstairs hosts the huge Primary En-Suite, 2 more bedrooms all with NEW Carpet and another full bathroom with brand new tiled shower, new toilet and new quartz sink! With three generous levels, a deck overlooking the pond, a cozy patio and a charming front porch, there’s space for everyone to relax and have their own space! Pull right into your own garage and your own driveway which makes life easy not to have to look for parking! The community offers fantastic amenities to enjoy like the inground and life-guarded pool, volleyball & tennis courts, fitness gym and direct access to the Cross Island Trail! Very close to the Castle Harbor Marina, many Beaches, Parks & Playgrounds and just a short stroll to local restaurants along the waters edge! Truly turn-key living in an unbeatable location on the desired Eastern Shore of Maryland! Come see what Kent Island living is all about! SUMMER is ALMOST here!

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 443-988-0483
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ADDITIONAL INFORMATION

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. Experience the warmth and comfort of Bayside Marina-your new sanctuary awaits!

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

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Chester 21619 Real Estate

Chester is located in Maryland. Chester, Maryland 21619has a population of 4,371. Chester 21619 is less family-centric than the surrounding county with 23.42% of the households containing married families with children. The county average for households married with children is 31.88%.

The median household income in Chester, Maryland 21619 is $84,835. The median household income for the surrounding county is $99,597 compared to the national median of $69,021. The median age of people living in Chester 21619 is 43.9 years.

Chester Weather

The average high temperature in July is 87 degrees, with an average low temperature in January of 28.3 degrees. The average rainfall is approximately 46.2 inches per year, with 12.7 inches of snow per year.

Chester Map

Chester Real Estate Market Conditions

  • Median sales price

    $476,250
    14.5%
    change since last quarter
  • # Active listings

    70
    30-day change

Chester Schools and Demographics

Education near Chester, MD

City County
High School Graduates 92.01 92.87
College Degree - 2 year 9.35 7.89
College Degree - 4 year 31.36 36.96
Graduate Degree 8.55 10.55
Expenditures per Student 15,198 15,198
Students per Teacher 14.4 14.4

Elementary Schools near Chester, MD

Grades Students P/T Ratio ZIP
Bayside Elementary School 03 - 05 402 16.1 21666
Cape St. Claire Elementary KG - 05 646 15.9 21409
Grasonville Elementary School PK - 05 494 15.9 21638
Kent Island Elementary School PK - 02 469 16.2 21666
Matapeake Elementary School PK - 05 493 15.4 21666
Rock Hall Elementary School PK - 05 187 14.3 21661
Windsor Farm Elementary School KG - 05 608 17 21409

Middle Schools near Chester, MD

Grades Students P/T Ratio ZIP
Matapeake Middle School 06 - 08 416 15.4 21666
Stevensville Middle School 06 - 08 474 13.5 21666

High Schools near Chester, MD

Grades Students P/T Ratio ZIP
Broadneck High School 09 - 12 2,104 18.4 21409
Kent Island High School 09 - 12 1,194 15.5 21666

Demographics near Chester, MD 21619

Zip Code City
Neighborhood Type Small town
Population 4,371 49,702
Population Density 835 134
Median Age 43.9 44.7
People per Household 2.4 2.6
Median Household Income 84,835 99,597
Average Income per Capita 53,406 49,178

Real estate near Chester