Chester MD Real Estate & Homes for Sale

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Beds:
3
Baths:
3.00
Sq.Ft.:
1,635
Status:
Active
MLS#:
MDQA2017430
Type:
Condo
Subdivision:
Bridgepointe
Year built:
1993
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

Adorable is the perfect word to describe this beautifully maintained townhome! Freshly painted and featuring a new roof and skylights (2025), this inviting home offers over 1,600 square feet of comfortable living space with three bedrooms, two full baths, and one-half bath. The main level showcases vaulted ceilings with skylights that fill the home with natural light, creating a bright and airy atmosphere. The open-air plan seamlessly connects the spacious living room and dining area, with room to comfortably accommodate four to six guests, making it ideal for both everyday living and entertaining. Step outside to the private porch overlooking a picturesque pond, where you can relax and enjoy the peaceful sound of the fountain. The main-level primary suite offers a walk-in closet, walk-in shower, and private access to the porch—your own tranquil retreat. The bright, open kitchen features abundant windows and space for a cozy breakfast table, creating the perfect spot to enjoy your morning coffee while taking in the views. Additional highlights include a one-car garage, convenient storage space off the porch, and low HOA fees compared to most communities. Ideally located just minutes from shopping, restaurants, churches, the Bay Bridge, and everyday conveniences, this charming townhome offers the perfect combination of comfort, style, and convenience. Don't miss the opportunity to make this wonderful home your own!

Beds:
3
Baths:
2.00
Sq.Ft.:
1,524
Status:
Active
MLS#:
MDQA2017690
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.41 Acres
Year built:
1974
Courtesy: Engel & Volkers Annapolis 443-292-6767
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ADDITIONAL INFORMATION

Coastal cottage charm meets waterfront living on picturesque Crab Alley Creek. Offering 120 feet of shoreline and direct access to the Eastern Bay, this beautifully maintained home combines privacy, convenience, and the very best of the Chesapeake lifestyle. A pier permit already in hand provides an exciting opportunity for the next owner to further enhance their waterfront experience. This move-in-ready residence features 3 bedrooms, 2 full baths, and a versatile bonus room that can serve as a home office, guest room, or potential 4th bedroom. Meticulously updated and lovingly maintained throughout, pride of ownership is evident at every turn. Thoughtful upgrades create a warm and inviting atmosphere, including under-cabinet lighting and dimmer switches throughout the home, allowing you to create the perfect ambiance for any occasion. The kitchen is both stylish and functional, featuring an additional beverage refrigerator, making entertaining family and friends a breeze. The bathrooms offer a touch of luxury with heated floors and built-in Bluetooth speakers, creating a spa-like retreat within your own home. Situated on a large, level waterfront lot, the property is designed for both relaxation and recreation. Across the creek, protected conservation land provides a peaceful, natural backdrop and exceptional privacy rarely found on the water. Raised garden beds offer the opportunity to grow your own herbs and vegetables, while the detached garage, two storage sheds, and attic provide ample space for tools, equipment, seasonal items, and all your waterfront essentials. Spend your evenings gathered around the fire pit overlooking the water, launch a kayak from your backyard, or cruise to one of the many waterfront restaurants accessible from the Eastern Bay. Whether you're entertaining guests or enjoying a quiet sunset, this property embraces the laid-back charm of coastal living. Conveniently located just 10 minutes from the Bay Bridge, 20 minutes from Annapolis, and approximately 90 minutes from the beach, you'll enjoy easy access to everything while feeling worlds away. A rare opportunity to own a turnkey waterfront retreat in one of Kent Island's most desirable locations, where every detail has been thoughtfully curated for comfort, convenience, and enjoyment.

Beds:
3
Baths:
3.00
Sq.Ft.:
3,434
Status:
Active
MLS#:
MDQA2017710
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.18 Acres
Year built:
2020
Courtesy: Wilson Realty & Staging LLC 410-304-2250
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ADDITIONAL INFORMATION

Welcome to luxury, comfort, and effortless living in the highly sought-after first section of Four Seasons at Kent Island. Offering a floor plan no longer available in the community's newer sections, this exceptional home combines thoughtful design with upscale finishes throughout. A spacious foyer welcomes you into an open and inviting layout that is perfect for both everyday living and entertaining. At the heart of the home is a stunning gourmet kitchen featuring an oversized center island that naturally becomes the gathering place for family and friends. Whether hosting indoors or enjoying the outdoors, you'll appreciate the seamless flow to the screened porch and beautifully designed patio complete with a built-in fire pit. The private primary suite is a true retreat, highlighted by an elegant tray ceiling, an impressive custom walk-in closet system, and a luxurious en-suite bath featuring a spacious walk-in shower, dual vanities, and a dedicated built-in makeup vanity. The main level also offers a second bedroom, full bath, private home office, and convenient laundry room, providing the ease of one-level living. Upstairs, guests will enjoy their own private space with an additional living area, bedroom, and full bath and access to the conditioned sky garage which is great for storage. Attached two car garage with epoxy flooring and inside access. Beyond the home, enjoy the award-winning lifestyle Four Seasons at Kent Island is known for. Residents have access to an impressive 24,000-square-foot clubhouse featuring indoor and outdoor pools, a state-of-the-art fitness center, tennis and pickleball courts, dog parks, walking trails, and an active calendar of social events—all designed for exceptional 55+ living.

Beds:
4
Baths:
3.00
Sq.Ft.:
1,979
Status:
Active
MLS#:
MDQA2017718
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.17 Acres
Year built:
2020
Courtesy: Douglas Realty LLC 866-987-3937
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ADDITIONAL INFORMATION

Gorgeous, like-new home on Kent Island! VA ASSUMABLE at 2.75% Interest!! Call for details!Fresh interior paint and new carpet throughout make this home truly move-in ready. The spacious living and dining areas offer plenty of room for relaxing and entertaining, while the inviting fireplace adds warmth and charm. The kitchen features a breakfast bar, pantry, abundant cabinetry, and plenty of storage. The spacious owner’s suite includes two walk-in closets and a private en-suite bath, creating a comfortable retreat at the end of the day. Step outside to enjoy the private backyard backing to trees—perfect for peaceful evenings or outdoor gatherings. Additional features include a water softener and convenient access to nearby boat ramps. Ideally located close to schools, shopping, golf, pickleball, restaurants, waterfront parks, walking trails, beaches, and local bars. This beautiful home shows exceptionally well and offers Kent Island living at its finest! virtual staging owner's suite/living room / dining room

Beds:
3
Baths:
2.00
Sq.Ft.:
1,192
Status:
Active
MLS#:
MDQA2017640
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.34 Acres
Year built:
1984
Courtesy: Compass 410-429-7425
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ADDITIONAL INFORMATION

Welcome to 2645 Cox Neck Road, a move-in ready home in the desirable Harbor View community of Chester. Offering 3 bedrooms, 1.5 baths, and situated on a spacious .34-acre lot, this well-maintained property combines comfort, convenience, and exceptional value at $399,500. Inside, you'll find a bright and inviting floor plan featuring a kitchen with a stylish tile backsplash, ample cabinetry, and luxury vinyl plank flooring. Thoughtfully maintained and updated over the years, this home offers peace of mind with a roof replaced within the last five years, replacement windows, siding, storm doors, and sliding glass door, as well as a recently replaced well pressure tank. Fresh interior paint and included appliances, including the washer and dryer, make moving in easy. Outdoor living is equally appealing with a charming front patio perfect for morning coffee and a large rear patio ideal for entertaining, grilling, or relaxing with family and friends. The beautifully maintained yard offers plenty of space for gardening, outdoor activities, or simply enjoying the outdoors. Two storage sheds provide ample room for tools, lawn equipment, and recreational gear. Located just minutes from Kent Island's popular restaurants, shopping, marinas, parks, and the Cross Island Trail, this home offers convenient access to everything the Eastern Shore lifestyle has to offer. Commuters will appreciate being less than 10 minutes from the Chesapeake Bay Bridge, while Harbor View residents enjoy a strong sense of community with neighborhood gatherings, holiday celebrations, yard sales, and other neighborhood events throughout the year. Whether you're searching for your first home, looking to downsize, or seeking a move-in ready property in a convenient Kent Island location, 2645 Cox Neck Road is an opportunity you won't want to miss.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2017542
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Lot size:
0.06 Acres
Year built:
2020
Courtesy: Real Broker, LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

Newly adjusted price. Please visit me at the OPEN HOUSE this Sunday from 1-3pm. Rarely available, this luxurious Severn penthouse in Four Seasons at Kent Island offers the perfect blend of waterfront beauty, comfort, and resort-style living. Built in 2020 and meticulously maintained, the home features an open-concept design filled with natural light and stunning views of Macum Creek and the Chester River. The gourmet kitchen is the heart of the home, showcasing a large island, premium appliances, and picturesque water views. Three spacious bedrooms, two-and-a-half baths, and inviting living spaces provide comfort and flexibility for everyday living and entertaining. Enjoy spectacular sunrises, abundant wildlife, and peaceful water views from your private balcony. Just steps away, you'll find creekside trails, kayak launches, picnic areas, and direct access to the natural beauty that makes Kent Island so special. Located in desirable Phase One, this penthouse offers enhanced privacy, mature surroundings, and freedom from nearby construction. Additional features include an oversized attached garage with interior access and a secure storage room. Residents enjoy access to Four Seasons' exceptional amenities, including a 24,000-square-foot clubhouse, indoor and outdoor pools, fitness center, pickleball and tennis courts, fishing pier, kayak launches, dog parks, walking trails, tiki bar, and more.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,832
Status:
Active
MLS#:
MDQA2017608
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2020
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

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

Beds:
2
Baths:
3.00
Sq.Ft.:
2,048
Status:
Active
MLS#:
MDQA2017526
Type:
Townhouse
Subdivision:
Gibsons Grant
Lot size:
0.09 Acres
Year built:
2009
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
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ADDITIONAL INFORMATION

Nestled in the charming community of Gibsons Grant, this exquisite townhouse offers a luxurious lifestyle with a perfect blend of comfort and elegance. Built in 2009, this Colonial-style residence spans 2,048 square feet and features two spacious bedrooms , with a another room that could be used for a 3rd bedroom and two and a half bathrooms, making it an ideal retreat for those seeking both style and functionality. Step inside to discover a thoughtfully designed interior that boasts hardwood and pine flooring, creating a warm and inviting atmosphere throughout. The combination kitchen and dining area is perfect for entertaining, featuring ample space for gatherings and culinary creations. Natural light floods the home, enhancing the inviting ambiance and highlighting the quality craftsmanship that defines this property. One year old HVAC and four year old hot water heater. The outdoor spaces are equally impressive, with a charming deck and porch that invite you to relax and enjoy the serene surroundings. Imagine sipping your morning coffee while taking in the gentle sounds of nature or hosting evening gatherings under the stars. The community pool and recreational facilities provide additional opportunities for leisure and relaxation, ensuring that every day feels like a vacation. Located just blocks from the Chester River, this property offers water-oriented living at its finest. Enjoy easy access to the river, perfect for kayaking or leisurely strolls along the waterfront. The community amenities, including a clubhouse, exercise room, and jogging paths, cater to an active lifestyle, while the meticulously maintained common grounds provide a picturesque backdrop for your daily activities. Parking is a breeze with a detached garage that offers additional storage space, ensuring that your home remains clutter-free. The association fee includes lawn care, snow removal, and trash services, allowing you to spend more time enjoying the luxurious lifestyle this community has to offer. Gibsons Grant is not just a place to live; it's a lifestyle choice that embraces the beauty of nature while providing modern conveniences. With its prime location, high-end features, and a strong sense of community, this townhouse is a rare gem that promises to be a cherished home for years to come. Experience the perfect blend of luxury and comfort in this stunning property, where every detail has been designed with your enjoyment in mind.

Beds:
5
Baths:
2.00
Sq.Ft.:
2,700
Status:
Active
MLS#:
MDQA2017588
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
1.65 Acres
Year built:
1948
Courtesy: Real Broker, LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

The locals called it Keister's Folly. In the mid-1940s, Dr. Keister built a barn on Kent Island overlooking Cox Creek, hoping to raise Black Angus cattle on 25 acres. The acreage was too small for the endeavor — but the barn he built was extraordinary. In the early 1960s, the developer of the Harbor View community converted it into a residence. The current owners' family purchased it in 1965 and has invested over $400,000 in improvements across sixty years of devoted stewardship. This property has never been publicly offered for sale — until now. Situated on 1.65 acres with 205 feet of protected waterfront on Cox Creek, this is one of the largest privately held waterfront parcels remaining in Harbor View. The 75-foot private pier extends into navigable tidal water with approximately 3.5 feet at mean low tide and two boat slips. Shoreline reinforced with professional rip-rap. Maps show Flood Zone X — outside 100-year and 500-year floodplains - buyer and agent should verify. The home offers 3,456 sq ft of living space across two levels including 700+ sq ft of unfinished second and third-level expansion space. Five bedrooms, two full baths. The upper-level primary suite features hardwood floors, panoramic water views, attached full bath, walk-in closet, private coffee bar with refrigerator, and a deck overlooking the creek. Updated kitchen with granite countertops, upgraded cabinetry, and high-end appliances, improvements throughout honor the building's barn heritage. Solid block construction. 200-amp electrical. Well water, public sewer. New Roof will be installed prior to settlement. Ideal for those who are seeking genuine Chesapeake waterfront with privacy, deep water access, and a property unlike anything else on the market. Be sure to download the Home Profile in the documents section for more details on the home including the history of the home.

Beds:
5
Baths:
5.00
Sq.Ft.:
3,225
Status:
Active
MLS#:
MDQA2016936
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.14 Acres
Year built:
2025
Courtesy: Samson Properties 703-378-8810
View additional info

ADDITIONAL INFORMATION

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 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:
3
Baths:
4.00
Sq.Ft.:
2,100
Status:
Active
MLS#:
MDQA2017442
Type:
Condo
Subdivision:
Bayside
Year built:
2000
Courtesy: Real Broker, LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

Exceptional value for this renovated 3-bedroom, 3.5-bath end-unit townhome in the premier Bayside waterfront community. Comparable properties in this Chester River community have recently sold for much more, making this an outstanding opportunity for buyers seeking turnkey condition with over $50,000 in premium upgrades. Welcome to Bayside living at its finest. This meticulously maintained home sits in one of Chester's most desirable waterfront communities, offering nearby water access for morning walks along the Chester River, resort-style outdoor pool for summer enjoyment, and professionally maintained grounds. Minutes from Route 50/301 for easy commuting, yet peacefully situated in a serene riverside setting close to shopping, dining, and recreational activities. The owners have transformed this residence with quality upgrades throughout. Real hardwood flooring spans the entire main and upper levels with no carpet anywhere in the home. The entry welcomes you with elegant slate tile while abundant natural light floods every room, creating bright and inviting spaces perfect for both daily living and entertaining. The completely renovated chef-inspired kitchen features top-tier stainless steel appliances including Thermador induction cooktop, GE Monogram wall oven, and Bosch dishwasher. Granite countertops, updated cabinetry, and recessed lighting complete this stunning space. The open-concept design connects seamlessly to the spacious living area, making entertaining effortless and family gatherings comfortable. Your main level living room centers around a cozy gas fireplace surrounded by built-in bookshelves, creating the perfect gathering spot year-round. Step outside to your private deck with retractable awning where you can enjoy winter water views of the Chester River. This outdoor space provides an ideal extension of your living area for morning coffee, evening relaxation, or weekend entertaining. The upper level primary suite serves as your personal retreat with a spacious walk-in closet and luxurious ensuite bathroom featuring a jetted soaking tub and separate shower. Your own private outdoor deck off the primary suite provides a serene escape for morning coffee or quiet evening moments. The second bedroom on this level includes its own attached full bathroom, offering privacy and comfort for family or guests. The versatile top-floor loft space features abundant natural light, two generous walk-in closets, and another full bathroom. Use this flexible area as a guest suite, home office, creative studio, or third bedroom based on your lifestyle needs. The possibilities are endless with this unique third-level retreat. Modern systems ensure comfort and efficiency throughout. The recently updated HVAC system provides year-round climate control while reducing energy costs. High-efficiency washer and dryer convey with the home for added value. The attached one-car garage offers protected parking and additional storage space, while the end-unit positioning provides enhanced privacy with no neighbors on one side. This home is completely turnkey and move-in ready. The combination of hardwood floors, premium Thermador and GE Monogram appliances, modern HVAC system, and updated finishes throughout means you can move in immediately and start enjoying your new lifestyle without any projects or renovations required. Low-maintenance living at its best. Your monthly Condo fee includes lawn maintenance, snow removal, community pool access, and recreation facilities, allowing you to spend your time enjoying the waterfront lifestyle rather than maintaining property. This is the perfect balance of Chester River community living with modern convenience and resort-style amenities. The value proposition is compelling. This home's aggressive positioning combined with over $50,000 in premium upgrades creates an exceptional opportunity for discerning buyers. The motivated seller situation, extensive recent improvements, prime end-unit location

Beds:
4
Baths:
4.00
Sq.Ft.:
3,312
Status:
Active
MLS#:
MDQA2017378
Type:
Single Family-Detached
Subdivision:
Gibsons Grant
Lot size:
0.22 Acres
Year built:
2012
Courtesy: TTR Sotheby's International Realty 410-673-3344
View additional info

ADDITIONAL INFORMATION

Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs, the spacious primary suite features a sitting area, two walk-in closets, and en-suite bath, alongside three additional bedrooms and two full bathrooms. The unfinished walkout basement includes a rough-in for a future bath. Outside, enjoy a fenced backyard complete with a patio and built-in fire pit—perfect for gathering year-round. Community amenities include swimming pool, clubhouse, fitness center, walking trails, community pier, picnic area, and kayak launch. Centrally located on Kent Island. Only 5 minutes to the Bay Bridge.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,595
Status:
Active
MLS#:
MDQA2017432
Type:
Condo
Subdivision:
Bayside
Year built:
1992
Courtesy: Realty Navigator 410-643-3404
View additional info

ADDITIONAL INFORMATION

Professional photos available July 2nd. Tenant is now out. Welcome to Bayside, where coastal living and resort-style amenities come together in one of the area’s most desirable waterfront communities. This 3-bedroom, 2.5-bath condo offers a relaxing marina-side setting with both upper and lower decks overlooking the marina, creating the perfect backdrop for morning coffee, evening sunsets, and everything in between. Inside, you’ll find a spacious layout designed for comfortable living, complete with a cozy gas fireplace, generous living spaces, and the convenience of a 1-car garage. Recent improvements include a new roof in 2023 and the front foot fee paid off in 2024, as well as a one-year home warranty for the buyer — adding additional value and peace of mind for the next owner. Life in Bayside is all about lifestyle. Residents enjoy access to resort-style amenities including a clubhouse, outdoor pool, fitness center, tennis courts, volleyball courts, and scenic walking and jogging trails — all just steps from the marina and moments from the Chesapeake Bay. Perfectly located near waterfront restaurants, local shops, and major commuter routes to Annapolis, Baltimore, and Washington D.C., this home offers the ideal blend of relaxation and accessibility. Whether you’re searching for a full-time residence or the perfect weekend waterfront escape, this Bayside condo captures the very best of Eastern Shore living.

Beds:
2
Baths:
3.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
MDQA2017364
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2023
Courtesy: Real Broker, LLC 855-450-0442
View additional info

ADDITIONAL INFORMATION

Adjusted price and ready for new owners!! Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four Seasons so desirable. 132 Wheelhouse Way is arguably one of the most sought-after locations in the community, offering fantastic water views and convenient ground-level access. Simply step out your patio door, turn right, and within moments you are at the resort-style amenities. No other location offers easier access to everything Four Seasons provides. With a $160,000 lot premium when this was built, its proximity to amenities is arguably the best in the community. The open-concept living and dining areas feature beautiful water views, an electric fireplace, and an inviting layout perfect for relaxing or entertaining. This condo has over $60,000 in builder upgrades and it shows. The gourmet kitchen includes quartz countertops, upgraded stainless steel appliances, GE Café double wall ovens, a large pantry, and luxury vinyl plank flooring throughout. The primary suite offers peaceful river and pond views, patio access, a walk-in closet, and an upgraded en-suite bath with a walk-in shower. A second bedroom suite with private bath and water views is ideal for guests, while the office with French doors provides flexible additional space. Additional highlights include elevator access, private storage, attached garage parking, cart storage, and a dedicated laundry area. Life at Four Seasons at Kent Island extends far beyond the home itself, offering a true resort-style lifestyle. Residents enjoy access to the Chester House Clubhouse, indoor and outdoor pools, a fitness center, walking trails, pickleball and tennis courts, a kayak launch, fishing pier, dog park, and more. Whether relaxing at the tiki bar and fire pit or connecting with neighbors at community events, every day feels like a getaway. Perfectly located on Kent Island with the Chesapeake Bay as the backdrop, this community offers the ideal blend of relaxation, recreation, and coastal living.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,302
Status:
Active
MLS#:
MDQA2017274
Type:
Condo
Subdivision:
Bridge Pointe
Year built:
1995
Courtesy: Keller Williams Realty Centre 410-312-0000
View additional info

ADDITIONAL INFORMATION

Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that backs to mature trees, creating a serene outdoor retreat, while being just steps from the community lake, walking paths, and boat parking lot! Inside, the functional layout offers spacious living areas, comfortable bedrooms, and plenty of natural light throughout. Whether you're looking for a primary residence, weekend getaway, or low-maintenance lifestyle near the Chesapeake Bay, this Kent Island gem is ideally situated close to shopping, dining, marinas, and commuter routes. Schedule your tour today!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,302
Status:
Active
MLS#:
MDQA2017340
Type:
Townhouse
Subdivision:
Bridgepointe
Year built:
1993
Courtesy: Rosendale Realty 410-758-0333
View additional info

ADDITIONAL INFORMATION

Low maintenance island living at its best! 6005 Bridgepointe Dr is freshly painted, deep cleaned, and ready for its new owners! All appliances new within the last two years, power washed & fresh paint on the deck with beautiful views of the pond. Easy access to RT50 - perfect for the commuter. Quiet neighborhood.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,160
Status:
Active
MLS#:
MDQA2017080
Type:
Single Family-Detached
Subdivision:
Chester
Lot size:
0.16 Acres
Year built:
1961
Courtesy: Thurston Wyatt Real Estate, LLC 410-320-6785
View additional info

ADDITIONAL INFORMATION

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.:
1,440
Status:
Active
MLS#:
MDQA2017146
Type:
Condo
Subdivision:
Queens Landing
Year built:
1998
Courtesy: Island Realty, LLC 410-643-4131
View additional info

ADDITIONAL INFORMATION

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

Beds:
3
Baths:
3.00
Sq.Ft.:
2,119
Status:
Active
MLS#:
MDQA2017258
Type:
Single Family-Detached
Subdivision:
Gibsons Grant
Lot size:
0.08 Acres
Year built:
2016
Courtesy: Samson Properties 703-378-8810
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ADDITIONAL INFORMATION

Save up to $390/month with a Lender Paid 1 Point Buy Down with Accepted Offer by 6/30/26 - ask Lender for Details! 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 engineered 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:
4
Baths:
5.00
Sq.Ft.:
4,717
Status:
Active
MLS#:
MDQA2017210
Type:
Single Family-Detached
Subdivision:
Southwind
Lot size:
2.3 Acres
Year built:
1997
Courtesy: Coldwell Banker Realty 410-224-2200
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ADDITIONAL INFORMATION

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:
2
Baths:
3.00
Sq.Ft.:
1,312
Status:
Active
MLS#:
MDQA2017164
Type:
Condo
Subdivision:
Queens Landing
Year built:
1995
Courtesy: Coldwell Banker Realty 410-263-8686
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ADDITIONAL INFORMATION

Seller is offering closing cost assistance for qualified buyers! 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:
7
Baths:
9.00
Sq.Ft.:
9,974
Status:
Active
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
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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.:
1,440
Status:
Active
MLS#:
MDQA2017082
Type:
Condo
Subdivision:
Queens Landing
Year built:
1998
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
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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:
4
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
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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:
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.

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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 Real Estate

Chester is located in Maryland. Chester, Maryland has a population of 4,371. Chester is less family-centric than the surrounding county with 25.7% 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 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 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

    $471,500
    14.5%
    change since last quarter
  • # Active listings

    53
    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

City County
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