Chester MD Real Estate & Homes for Sale

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Beds:
4
Baths:
3.00
Sq.Ft.:
2,870
Status:
Active
MLS#:
MDQA2016140
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.14 Acres
Year built:
2025
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

Huge Price Reduction on this beautiful, less than 1 year old home in the sought after community of Four Seasons at Kent Island. This Simone model home with loft features 4 bedrooms and 3 full baths is awaiting it's next owner and priced well below the new construction models. With recent improvements including paint and Plantation Shutters, this home is move in ready so that you can enjoy this community and the upcoming Spring and Summer on fabulous Kent Island. Situated on a premium lot with close proximity to the 24,000 sq. ft. club house, indoor and outdoor pools, you won't be disappointed in touring this home. The gourmet kitchen with the "Farmhouse Collection" design features stainless appliances including both a gas stove and built in wall oven to impress the most pampered chef with the oven and stove never used. The master suite is beautifully designed with a master bath which includes a large walk-in shower, double vanity sink and large walk-in closet. The 2nd bedroom and 2nd full bath are located on the main level and the 3rd and 4th bedrooms along with the 3rd full bath are located on the 2nd level. As you pass through the main living area including the propane fireplace, you may eventually choose to relax on the rear screened patio to enjoy some of the outdoor living that the area offers. This home also includes a Rinnai Tankless Water Heater.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,634
Status:
Active
MLS#:
MDQA2015732
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.21 Acres
Year built:
2024
Courtesy: TTR Sotheby's International Realty 410-280-5600
View additional info

ADDITIONAL INFORMATION

Welcome to 132 Kestrel Lane, an exceptional home in the premier waterfront community of Four Seasons at Kent Island. Offering over 3,600 square feet of thoughtfully designed living space, this residence combines elegant design, modern functionality, and a lifestyle centered around comfort, connection, and the natural beauty of the Chesapeake Bay. From the moment you arrive, the covered front porch and charming curb appeal set the tone for what awaits inside. The grand two-story foyer opens to soaring ceilings, wide plank wood flooring, and light-filled spaces dressed in timeless plantation shutters. The main level is designed for easy living, with 10-foot ceilings that create a sense of openness and flow. At the heart of the home, the great room features cathedral ceilings, crown molding, and a gas fireplace, providing a warm gathering place for both intimate evenings and lively entertaining. The designer kitchen blends beauty and function with a large island, stainless steel appliances, a gas range, backlit cabinetry, and a beautifully lit backsplash that adds a touch of sophistication. The open-concept design extends into the breakfast area, making mornings and casual meals a delight. A screened-in porch and fenced patio create a seamless transition from indoor living to outdoor enjoyment, perfect for entertaining or simply savoring quiet moments surrounded by nature. The first-floor primary suite is a true retreat, complete with a spacious walk-in closet outfitted with built-ins and a spa-inspired bath designed with relaxation in mind. A second bedroom with its own private bathroom on the main level offers comfort and privacy for family or overnight guests, while a dedicated office provides the flexibility to work from home with ease. The convenience of a mudroom with built-ins and a first-floor laundry adds to the thoughtful design of this home. Upstairs, a large loft-style living area can serve as a media or game room, offering additional space for recreation, relaxation, or hobbies, while two generously sized bedrooms share a well-appointed bathroom. A large two-car garage with an extra storage and workshop area provides ample space for all your needs—including the perfect spot to store multiple kayaks. Every detail of this home has been carefully curated, from the crown molding to the custom finishes, creating a space that feels both refined and welcoming. Beyond the home itself, life at Four Seasons at Kent Island offers an unparalleled resort-style experience. Residents enjoy exclusive access to the Chester House Clubhouse, where a ballroom, bar and lounge, gathering spaces, and a demonstration kitchen set the stage for community and celebration. Fitness and wellness are at the forefront with indoor and outdoor pools, a state-of-the-art fitness center, yoga room, and walking paths. Outdoor amenities abound, from tennis, pickleball, and bocce courts to a kayak launch, fishing pier, and dog park. Evenings can be spent at the fire pit, tiki bar, or amphitheater, creating countless opportunities to connect with neighbors and enjoy the Chesapeake lifestyle. Perfectly situated on Kent Island, this home is more than just a place to live—it’s a way of life. Here, every day feels like a retreat, with the Chesapeake Bay as your backdrop and a vibrant community at your doorstep. Welcome to 132 Kestrel Lane, where luxury, comfort, and lifestyle meet.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2016336
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2020
Courtesy: Real Broker, LLC 855-450-0442
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ADDITIONAL INFORMATION

This rare, luxurious Severn penthouse in Four Seasons at Kent Island is available immediately and offers a lifestyle that blends comfort, elegance, and natural beauty. Built in 2020 and beautifully maintained, the residence features an open floor plan with abundant windows that fill the home with natural light, creating a warm, inviting atmosphere. At the heart of the home is a stunning kitchen with a generous island and water views of the Chester River and Macum Creek, paired with high-end gourmet appliances that make everyday living and entertaining a pleasure. The spacious living areas are designed for easy flow and connection, while the three bedrooms provide peaceful retreats, and the 2.5 baths offer convenience and privacy for residents and guests. This exceptional property offers direct access to Macum Creek, a pond, and sweeping views of the Chester River. Enjoy watching wildlife from your private balcony or take a short walk to the two nearby creekbank trailheads, behind buildings 1 & 3, with 2 kayak launch points, and picnic areas. Enjoy peaceful moments by the water, whether it’s kayaking, simply soaking in the serene views by the picnic tables of duck and Tundra Swans, or watching the deer graze, and the Osprey and local eagles soar from the sanctuary of your balcony. Brace yourself for brilliant sunrises that flood the interior with crisp light until late morning, year-round, as well as the westerly incandescence of sunsets whose warm light stretches lazily across Macum Creek at dusk to illuminate the far wooded bank. Phase One living offers peace, privacy, and an unmatched setting with no construction disruption and expansive natural views instead of nearby buildings. The oversized attached garage with inside access provides secure parking, extra room for maneuverability, and additional storage, while the secure interior storage room on the main level adds even more practicality. Residents enjoy access to the impressive 24,000 square foot clubhouse with a billiards room, casual lounge, library, fitness center, party and meeting rooms, and an indoor heated pool and spa. Outdoor amenities include a resort-style pool, tiki bar, concert space, fishing pier, day docking, kayak launches, trails connecting to the Cross Island Trail, tennis and pickleball courts, and dog parks. Please view the 360 Video Tour to walk through this desirable penthouse condo virtually.

Beds:
1
Baths:
1.00
Sq.Ft.:
724
Status:
Active
MLS#:
MDQA2016442
Type:
Condo
Subdivision:
Queens Landing
Year built:
1983
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

Queens Landing - One bedroom condo with living room overlooking kitchen, good for entertaining. Private patio off bedroom with secured storage. Laundry is stackable located in bedroom. You will enjoy the Queen's Landing community clubhouse, marina, tennis court and pool and well as the trails in the community. Call today for your private showing.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2016122
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2024
Courtesy: Long & Foster Real Estate, Inc. 410-544-4000
View additional info

ADDITIONAL INFORMATION

Rare resale condo, turnkey! Your dream retreat awaits in this stunning luxury condo, where modern elegance meets breathtaking natural beauty. This exquisite residence features two spacious bedrooms, each with its own en-suite bath, and an additional half bath for guests. The thoughtfully designed office boasts custom built-in cabinets, providing both functionality and style.--Step into the heart of the home, where the stylish gray kitchen cabinets perfectly complement the stunning quartz countertops and stainless steel appliances. The expansive kitchen island invites culinary creativity and social gatherings, making it the perfect space for entertaining. --Relax in the cozy ambiance of the decorative fireplace, or step out onto the private balcony to soak in the serene water views and observe the vibrant wildlife in the surrounding marsh and river. With bright, airy spaces and a neutral decor palette, this condo is a canvas to suit every design.--As part of a vibrant community, you'll enjoy access to a gorgeous community center featuring every amenity imaginable. Dive into the zero entry pool, host gatherings in one of multiple outdoor entertaining areas, or conduct meetings in the indoor meeting rooms. The grand ballroom is perfect for celebrations, while the state-of-the-art fitness center caters to your wellness needs. For pet owners, a dog park and scenic walking trail await, along with a picturesque pier for leisurely strolls. --Experience the perfect blend of luxury living and natural serenity in this exceptional condo that truly has it all. Don’t miss your chance to claim this remarkable property as your own!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2016358
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2026
Courtesy: KOVO Realty 240-375-5074
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ADDITIONAL INFORMATION

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

Beds:
2
Baths:
3.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
MDQA2016230
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2022
Courtesy: EXP Realty, LLC 888-860-7369
View additional info

ADDITIONAL INFORMATION

Welcome to 1000 Herons Nest Way, where you can live the good life at an great price. This immaculate two bedroom condo, with two and a half baths and additional flex space, provides turn key convenience and resort style amenities. This home is a MUST SEE! This FORMER MODEL is like new and includes features that other condos won’t - including decorator upgrades, custom designed closets, plantation shutters, and a wireless sound system for multi-room audio streaming right from your phone or television. Step inside to discover an open floor plan that connects space to create an inviting atmosphere for gatherings and everyday living. The large living room opens to a large balcony with EXCEPTIONAL PRIVACY that you won’t find in many other locations. With no buildings or homes behind yours, you can watch the sunrise while sipping morning coffee and enjoying views of nature. The flex space has custom built ins that are great for displaying pictures and keepsakes. The flex space can adapt to your changing needs and could serve as an office, craft room, reading area, place to work out, or provide additional sleeping space. All rooms feature luxury vinyl plank flooring, custom light fixtures, and recessed lighting. The kitchen is equipped with upgraded appliances, a gas stove top, built in microwave, quartz counters, beautiful upgraded cabinetry with lighting, and an oversized kitchen island. The primary suite has a luxury owner's bath, two spacious closets upgraded by California Closets, and additional access to the balcony. The bright and airy 2nd bedroom has a unique designer accent wall, a full bath, and an additional walk-in closet. Windows in both bedrooms bring in lots of natural light and are upgraded with the clean look of plantation shutters. The separate laundry room is equipped with an oversized washer and dryer. Off the foyer is a half bath for family and guests. This home also has a garage and an additional storage room on the first floor. The condo has a desirable second floor location, near the elevator, and steps from the building’s furnished "Club Room" which provides quiet space to relax, read, or meet with friends. The HOA includes building maintenance, repairs, and access to all that Four Seasons has to offer - you can enjoy the activities worry free. The recent surge in utility pricing is less of a concern here, as the owner’s combined gas and electric bills over the past 12 months has averaged about $140. Water and sewer is included in the condo HOA. This may be a separate charge at other locations. There is something for everyone in this community. Fantastic amenities include an amazing clubhouse with an indoor pool and hot tub, fitness center, library, and game room. Outdoors you find a riverside infinity pool, gas fire pits, tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, walking paths that link to the Cross Island Trail, pickleball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. You can also enjoy daily activities such as yoga, exercise classes and clubs for biking, billiards, books, baking, cards, mahjong, and more. This unit is just a short walk to community kayak racks with launch access. The owner paid for the kayak rental space for 2026.

Beds:
5
Baths:
4.00
Sq.Ft.:
3,250
Status:
Active
MLS#:
MDQA2016194
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.43 Acres
Year built:
2007
Courtesy: Coldwell Banker Realty 410-263-8686
View additional info

ADDITIONAL INFORMATION

Price improvement! Motivated sellers. This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning room transitions seamlessly into a sunroom, providing flexible space for dining, relaxing, or working from home. The gourmet eat-in kitchen offers granite countertops, a substantial center island, pantry, and an open-concept design that opens into the family room and sunroom. The primary suite is generously sized, featuring a tray ceiling and a well-designed bath with custom tile shower and double vanity. The remaining four bedrooms share two jack-and-jill style bathrooms offering convenience for family and guests. Outdoor living is equally appealing, with an 800-square-foot wraparound deck ideal for entertaining. The property also offers space for a potential in-ground pool (buyer to verify with Planning & Zoning). Additional features include custom hardwood and tile flooring run throughout, tailored Roman blinds and wood shutters, new HVAC system, finished garage, and dedicated laundry room with new washer, dryer, and utility sink. A rare 1,820-square-foot crawl space with 4-foot ceilings, finished concrete floor, and indoor access provides plenty of additional storage. Built by local builder Lacrosse Homes with numerous upgrades, this well-maintained home offers immediate value in one of the most popular areas on the Eastern Shore - all with no HOA. Schedule your tour today.

Beds:
3
Baths:
2.00
Sq.Ft.:
2,200
Status:
Active
MLS#:
MDQA2016206
Type:
Single Family-Detached
Subdivision:
Dominion
Lot size:
0.99 Acres
Year built:
1896
Courtesy: Coldwell Banker Realty 410-224-2200
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ADDITIONAL INFORMATION

Start living the watermen dream! This charming home offers a thoughtfully designed layout with an open, airy flow and spacious rooms throughout. Situated on nearly one acre, you’ll enjoy both comfort and room to roam. The oversized living area is filled with natural sunlight streaming through the windows, creating a warm and inviting atmosphere. The first floor recently fresh coat of paint. Step outside to the private side deck — perfect for entertaining, hosting summer barbecues, or simply relaxing with friends and family. Featuring three bedrooms and 1.5 baths, this home includes a generously sized primary bedroom with vaulted ceilings and a walk-in closet. A storage shed provides extra space for tools and equipment, while the expansive yard offers endless possibilities for outdoor fun, gardening, or future enhancements. Bring your personal touches and make this home truly your own!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2016096
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2026
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Chester offers a thoughtfully designed open floorplan with a projected settlement date of October 2026. Ideal for modern living, this home features 2 bedrooms, 2.5 baths, and a 1-car garage. The main living area is anchored by an electric fireplace, while a dry bar adds both function and style for entertaining. A dedicated home office with lighted French doors provides a flexible space perfect for working from home or quiet retreat. The kitchen is equipped with a single oven, microwave, gas cooktop with range hood, dishwasher, pendant lighting, and a tile backsplash, all complemented by quartz countertops for a polished finish. Luxury vinyl plank flooring flows throughout the home, with tile flooring in the two full baths for added durability. The owner’s bath features a walk-in shower with a seat and handheld shower wand, double sinks, and quartz countertops, creating a spa-inspired retreat. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Beds:
1
Baths:
1.00
Sq.Ft.:
724
Status:
Active
MLS#:
MDQA2016014
Type:
Condo
Subdivision:
Queens Landing
Year built:
1983
Courtesy: Coldwell Banker Realty 410-263-8686
View additional info

ADDITIONAL INFORMATION

Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a waterfront condominium community on Kent Island located minutes from Rt. 50 and a short walk to local dining and the Cross Island Trail. The community offers a club house, marina, pool, fitness center, pickleball, tennis, and racquetball courts, and social activities throughout the year. Schedule your tour today!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,602
Status:
Active
MLS#:
MDQA2016080
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2026
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Severn is thoughtfully designed for comfort and everyday entertaining, with a projected settlement of November 2026. This home offers 3 bedrooms, 2.5 baths, and a 1-car garage, all wrapped in a smart, functional layout. Inside, you’ll find stylish touches like an electric fireplace and a built-in dry bar, perfect for hosting or winding down at home. The owner’s suite is a true retreat, complete with a private sitting room and large walk-in closets. The spa-inspired owner’s bath features a walk-in shower with seat and handheld wand, double sinks, and quartz countertops. The kitchen is equipped with a gas cooktop, single oven, microwave, range hood, dishwasher, pendant lighting, and a tile backsplash, all anchored by quartz countertops. Laminate flooring flows throughout the home, with tile in both full bathrooms for a polished finish. For a full list of features for this home, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available.

Beds:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2015800
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2021
Courtesy: RE/MAX Leading Edge 410-224-3200
View additional info

ADDITIONAL INFORMATION

Four Seasons @ Kent Island - 55+ Community - Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas cooktop with range hood, wall oven + microwave combo and a huge Island that accommodates plenty of bar seating. Spacious Bedroom suites each with private full baths and generous closet spaces. The Primary bath has His 'n Her's double sinks with Moen fixtures, comfort height vanities, large vanity mirrors, medicine cabinets and a walk-in tiled shower with seat. The Primary bedroom features 2 closets; one walk-in-closet and one generous wall closet, a ceiling fan and a single French door to access the balcony. The 2nd Bedroom is large enough to hold a traditional sized bedroom set and features a tub/shower combo in the bath. The open Great Room is large, bright and has serene pond views and winter water views of Macum Creek with oversized sliders to a covered balcony. You will love the convenient laundry room located off the foyer area that accommodates the included full-sized GE washer and dryer. Elevator down to the Lobby level to your private garage and a just a few steps down the corridor is your private, keyed storage closet. This condo building features a secure lobby entrance and is impeccably decorated and maintained. Additionally, the 2nd floor has a common Club Room/Meeting Room great for socializing with your neighbors or as additional entertainment space. It features Public Water, Public Sewer, individually metered propane gas heat and cooking. All residents have access to the community amenities which include a huge 20,000 sf Club House with Billiards Room, Casual Lounge Area, Fitness Center, Party and Meeting rooms, and fabulous Indoor Heated Pool & Spa. Outside awaits a resort-like Pool, Cabana House, Private Beach Area, Outdoor Concert Space, Pier for Fishing and taking in the magnificent Chester River views & Kayak launch and Walking Trails. Pickle Ball enthusiasts you are in luck as there are Tennis Courts and Pickle Ball Courts for all, and grand kids can be entertained at a small Playground Area. Come tour today and see why this is THE place to be in Kent Island for 55+ living!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,750
Status:
Active
MLS#:
MDQA2015604
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.28 Acres
Year built:
1988
Courtesy: Five Star Real Estate 240-222-3200
View additional info

ADDITIONAL INFORMATION

*PRICE IMPROVEMENT!* Welcome to this beautifully renovated ranch-style home offering 4 bedrooms, 2 full bathrooms, and a spacious open floor plan designed for modern living. Completely remodeled from top to bottom, this move-in ready property combines style, comfort, and functionality in every detail. The stunning kitchen features sleek quartz countertops, stainless steel appliances, and a large pantry, making it perfect for everyday living and entertaining alike. The open layout flows seamlessly into the main living areas, creating a bright and inviting space for gatherings. Both full bathrooms have been thoughtfully updated with ceramic tile flooring, spacious showers, and top-of-the-line vanities. The primary suite offers a private retreat with a luxurious dual vanity sink, ceramic tile flooring, and an oversized stand-up shower. Step outside to enjoy the huge backyard with endless possibilities for entertaining, gardening, play, or simply relaxing outdoors. Conveniently located near the Chesapeake Bay, you’ll have easy access to boat ramps, beaches, parks, and countless recreational opportunities. This fully remodeled gem is the perfect blend of modern upgrades and coastal lifestyle—don’t miss your chance to call it home! Schedule your showing before it's too late!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDQA2015236
Type:
Condo
Subdivision:
Queens Landing
Year built:
1998
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

Owners have lowered the price by $10,000 and are willing to look at offers! Nothing to do but move in! Be in this spring to enjoy all that summer offers on the shore!! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout the living areas and new vinyl flooring in the kitchen. A propane fireplace highlights the great room turning chilly nights into cozy nights! On warm days, enjoy relaxing in the enclosed patio/porch or just being outside. Being an end-unit it offers lots of privacy. Any and all assessments have been paid by the owner, so you are ready to go and enjoy all the amenities that Queens Landing is known for...beautiful waterside pool, the club house with a party room, racquet ball court, exercise room, tennis courts, jogging trail, and more! Close to the cross-island trail, the Matapeake Dog Park, restaurants, schools, library...it is a wonderful place to live! Whether you are looking for a place to use as a vacation or weekend home, or as a year-round residence, this will suit both needs. It's situated in a great location...minutes to the Bay Bridge for any commuters to the western shore, and many airports, and an easy drive to the MD and DE beaches! Note: 3 pictures have been Virtually Enhanced!

Beds:
3
Baths:
4.00
Sq.Ft.:
2,930
Status:
Active
MLS#:
MDQA2015636
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2022
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Franklin Model Home offers a beautifully designed open-concept layout enriched with elevated designer finishes—available now for immediate settlement with a rent-back opportunity. With 3 bedrooms, 3.5 baths, and a 2-car garage, this home provides a refined blend of comfort, versatility, and modern style. Standout features include a dedicated home office, a cozy fireplace, and a screened patio that extends your living space outdoors. Thoughtful design details—such as barn doors, crown molding, and a custom feature wall—add character and craftsmanship throughout. As an added bonus, all model home furniture is included, offering a seamless move-in-ready experience. The beautifully appointed kitchen features a range, single oven, microwave, range hood, dishwasher, French door refrigerator, stylish pendant lighting, and a coordinating tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a fresh, integrated design. LVP flooring extends across the main level for durability and style, with tile in all full baths and carpet in Bedrooms 2 and 3 for added comfort. The owner’s bath offers a spa-inspired shower with a built-in seat, handheld shower wand, and double sinks—creating a relaxing and functional daily retreat. For a full list of included features, please contact our sales representatives. 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#:
MDQA2015634
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2022
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Kerr Model Home offers a beautifully crafted layout enhanced with elevated designer finishes throughout—available now for immediate settlement with a rent-back opportunity. Thoughtfully designed with 3 bedrooms, 3 baths, and a 3-car garage, this home blends spacious living, refined styling, and everyday functionality. Standout features include a dedicated home office, an inviting fireplace, and professionally designed details such as a feature wall, crown molding, and sliding barn doors that add custom character to each space. As an added benefit, all model home furniture is included, providing a fully move-in-ready experience. The gourmet kitchen is equipped with a Profile range, single oven, microwave, range hood, dishwasher, side-by-side refrigerator, elegant pendant lighting, and a designer tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a clean, cohesive finish. Hardwood flooring extends across the main level, with tile in all full baths and carpet in Bedroom 2 and the loft for added comfort. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a spa-inspired retreat designed for everyday ease. For a full list of included features, please contact our sales representatives. 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:
2
Baths:
2.00
Sq.Ft.:
1,993
Status:
Active
MLS#:
MDQA2015632
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2022
Courtesy: KOVO Realty 240-375-5074
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ADDITIONAL INFORMATION

The Jenkins Model Home offers a beautifully crafted open-concept layout paired with high-end designer finishes throughout—now available for immediate settlement with a rent-back opportunity. Thoughtfully designed with 2 bedrooms, 2 baths, and a 2-car garage, this home blends comfort, sophistication, and convenience. Standout features include a dedicated home office, a cozy fireplace, and a screened patio ideal for indoor–outdoor living. Elevated design moments—such as feature walls, ceiling beams, and barn doors—bring custom flair to each space. As a true bonus, all model home furniture is included, offering a completely move-in-ready experience. The chef-inspired kitchen showcases a Café range, single oven, microwave, range hood, dishwasher, side-by-side refrigerator, stylish pendant lighting, and a designer tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a cohesive, upscale look. Hardwood flooring extends across the main level, with tile in all full baths and carpet in Bedroom 2 for added warmth. The owner’s bath features a shower with seat, handheld shower wand, and double sinks, creating a comfortable and functional retreat. For a full list of included features, please contact our sales representatives. 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:
5
Baths:
5.00
Sq.Ft.:
3,225
Status:
Active
MLS#:
MDQA2015638
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2022
Courtesy: KOVO Realty 240-375-5074
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ADDITIONAL INFORMATION

The Tuscaloosa Model Home offers an exceptional open-concept design enriched with high-end finishes and thoughtful upgrades throughout. Available for immediate settlement with a rent-back opportunity, this expansive home features 5 bedrooms, 4.5 baths, and a 3-car garage, delivering both space and sophistication. Standout features include a dedicated home office, an inviting fireplace, and a screened patio perfect for indoor–outdoor living. Custom design elements—such as barn doors, ceiling beams, and a striking feature wall—bring warmth, character, and craftsmanship to every corner. As a premium bonus, all model home furniture is included, providing a fully move-in-ready lifestyle. The chef-inspired kitchen showcases a Profile range, single oven, microwave, range hood, dishwasher, French door refrigerator, elegant pendant lighting, and a stylish tile backsplash. Quartz countertops elevate both the kitchen and the owner’s bath for a clean, cohesive look. Hardwood flooring spans the main level for timeless appeal, with tile in all full baths and carpet in Bedroom 2, the loft, and Bedrooms 4 and 5 for added comfort. The owner’s bath features a luxurious shower with a built-in seat, handheld shower wand, and double sinks—creating a serene, spa-like retreat. For a full list of included features, please contact our sales representatives. 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.:
2,795
Status:
Active
MLS#:
MDQA2015026
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.18 Acres
Year built:
2020
Courtesy: Real Broker, LLC - Annapolis 855-450-0442
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ADDITIONAL INFORMATION

If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities. But what really sold them was the way this home made everyday life feel easy, peaceful, and a little bit indulgent. From the moment you walk through the front door, the open layout just flows. The gourmet kitchen is the heart of the home—with a massive island, double ovens, gas cooktop, and more cabinet space than you’ll know what to do with. It opens to a sunny dining area and a living room that invites you to sink in and stay awhile. Downstairs, you’ll find two spacious bedrooms, including a primary suite that feels like a retreat. The spa-like bathroom, walk-in closet, and tray ceiling add a touch of everyday luxury. There’s also a den that can flex into a home office, reading room, or whatever you need it to be. Upstairs is a private guest suite with a third bedroom, full bath, and a bonus loft space that’s perfect for movie nights or extra living space. But the magic continues outside. The oversized patio was made for entertaining—complete with a built-in firepit, gas line for your grill , and even a five-person Thermospa hot tub. Whether it’s coffee in the morning or wine after sunset, this is where you’ll want to be. Other thoughtful touches? There’s a heated and cooled garage with extra space for a third vehicle or golf cart, and a sky basement for bonus storage. Throughout the home, you'll find upgrades like luxury vinyl plank flooring, under-cabinet kitchen lighting, custom bathroom finishes, recessed lighting, and so much more. And then there’s the community. Four Seasons at Kent Island is truly one-of-a-kind. Want to start your day with yoga? Go for a paddle on the river? Meet friends at the outdoor bar to catch the game by the firepit? It's all here. There’s a 24,000 sq ft clubhouse, both indoor and outdoor pools, a state-of-the-art gym, game room, pickleball and tennis courts, walking and biking trails, a pier for fishing and boating, a kayak launch, and even a dog park. The community is tucked away, peaceful and private—but you're just minutes from restaurants, wineries, breweries, and shops. And if you ever need a city fix, Annapolis and Easton are an easy 20-30 minute drive away. The best way to describe this home and community? It’s a place where life slows down in the best way. Where neighbors become friends. Where the to-do list gets a lot shorter—and the “want-to-do” list gets a whole lot longer. So if you're looking for more than just a new house—if you're ready for a new chapter filled with connection, ease, and everyday joy—135 Nauset Lane might be exactly what you’ve been waiting for.

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
MDQA2014542
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.55 Acres
Courtesy: Keller Williams Flagship 410-729-7700
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ADDITIONAL INFORMATION

*****Immediate Delivery*****WATERFRONT DEEP WATER ****Schedule showoing today! The Blue Heron is a new home design offered by Lacrosse Homes. The single family design features now one but TWO decks -- one from the second floor great room and the second from the third level primary bedroom suite. Take in all the beautiful sights and sounds of a Coastal Maryland lifestyle in this home built for entertaining and an enhanced lifestyle! There is room for everyone in this home, starting with a main level 2-car garage, rec room area, full bath & exercise/office -- this is your fun zone or whatever zone! The second level is light-filled and open with island kitchen featuring upgraded finishes, dining area, powder bath and great room with deck. You can ADD another deck on the rear of the home off the dining area if you're looking for more outdoor space. The third level features a laundry, three bedrooms including the spacious primary bedroom with updated bath and another stunning deck. The Blue Heron is a beautiful home and will serve a multitude of lifestyles. Explore your options today!

Beds:
2
Baths:
3.00
Sq.Ft.:
2,003
Status:
Active
MLS#:
MDQA2015222
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2021
Courtesy: Coldwell Banker Realty 410-263-8686
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ADDITIONAL INFORMATION

A price improvement has been made with an additional seller paid $5,000.00 closing assistance to a qualified buyer's settlement fees. This unit has approximately $55,000.00 in upgrades and shows like a model home. Love Where You Live! Experience resort-style living that blends comfort, luxury, and convenience—just steps from the waterfront. Enjoy peaceful mornings without the disruption of construction nearby. This highly sought-after first-floor condo is move-in ready and has been meticulously maintained, featuring numerous upgrades throughout. Step inside to an open, light-filled layout enhanced by crown molding, recessed lighting, and direct views of the lush greenspace with seasonal water glimpses. The gourmet kitchen and dining area are ideal for entertaining, offering a spacious island with seating, quartz countertops/bar, sleek wifi enabled appliances, and seamless flow into the living room. Unwind by the cozy fireplace or open the double sliding glass doors to your private patio—perfect for watching the sunrise, morning coffee, reading, or simply enjoying the peaceful natural setting. The owner’s suite offers both a walk-in and secondary closet, private patio access, and a luxurious en-suite bath with dual sinks and a spa-inspired frameless glass shower. The guest suite is bright and spacious, complete with its own en-suite bath, custom tilework, and large vanity. A bonus room with upgraded frosted glass doors provides the perfect space for a home office, workout area, or reading nook. Additional highlights include: LVP flooring throughout the entire home, interior access to a private one-car garage, and a secure storage unit. From your patio, take a stroll along the walking trail where you can take in the sights and sounds of nature to discover tranquil views and your kayak launch. The community also has direct access to the Kent Island Cross Island Trail. Many extra amenities to enjoy including an indoor heated pool, outdoor infinity pool, firepits, pickleball and tennis courts, dog park, and beautiful walking and biking trails. Live every day like you’re on vacation—this stunning condo offers the lifestyle you’ve been waiting for and is a must see to experience all of the upgrades! Water and sewer fees are already included in the owners monthly COA.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
MDQA2014528
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2023
Courtesy: Long & Foster Real Estate, Inc. 410-546-3211
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ADDITIONAL INFORMATION

Welcome to Luxury Condo Living at The Four Seasons at Kent Island, An active 55+ Community packed with tons of amenities . Move -in to this turn key luxury condo with plenty of natural light with "Perfect Fit" planation shutters and ample privacy on all windows and doors. The kitchen has a gourmet package including quartz countertops and a large island with space for barstool eating, subway tile backsplash, staggered cabinets, and stainless steel modern appliances. The great room has a seasonal view of the Chester River and a traditional electric fire place with shiplap accents fostering a feeling of warmth and tranquility. The primary bedroom/bathroom is spacious with two sizeable walk-in closets. The primary bedroom also includes attached sitting room with water-view and access to the balcony overlooking a pond that attracts wildlife. All bedrooms of this Severn Model offer custom closets designed and constructed by "Chesapeake Closets". The unit comes with a first floor assigned one car garage and an assigned climate-controlled storage closet. Come join the easy life! Call for your private showing!

Beds:
2
Baths:
1.00
Sq.Ft.:
764
Status:
Active
MLS#:
MDQA2014252
Type:
Single Family-Detached
Subdivision:
None Available
Lot size:
0.17 Acres
Year built:
1926
Courtesy: The Parker Group 302-217-6692
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ADDITIONAL INFORMATION

This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details. Please note that access to 1405 Little Creek Rd is via 104 Little Creek Ct, followed by a left turn. Do not use or enter any neighboring driveways or properties as they are privately owned and clearly marked with “No Trespassing” signs. For safety reasons, please respect these boundaries.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,248
Status:
Active
MLS#:
MDQA2011168
Type:
Single Family-Detached
Subdivision:
Marling Farms
Lot size:
0.35 Acres
Year built:
1971
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

PRICE Improvement...Discover the charm of this fully updated ranch in a serene, water-privileged community! With a spacious yard and an inviting open floor plan, this home features a stunning new kitchen complete with a large white granite island, sleek white cabinets, and stainless steel appliances. Sunlight floods the dining area through new sliding doors, while the generous living room is accented with stylish shiplap walls. There's Nothing Like NEW! Step onto the new flooring that leads you to three roomy bedrooms and two beautifully renovated full baths. Every detail has been attended to, with all-new windows, siding, plumbing, fixtures, electrical panel, light switches, septic work, water heater, doors, drywall, and a new HVAC system. With a recent roof and a dehumidified crawl space featuring a vapor barrier, this home is move-in ready—no worries, just settle in! The community enhances your lifestyle with access to four beaches, three boat ramps, a playground, ball fields, a basketball court, a picnic pavilion, a fishing pier, and plenty of opportunities for gatherings. This is the perfect place to create lasting memories!

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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

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

    77
    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