Chester MD Real Estate & Homes for Sale

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Beds:
2
Baths:
2.00
Sq.Ft.:
1,280
Status:
NEW LISTING
MLS#:
MDQA2015236
Type:
Condo
Subdivision:
Queens Landing
Year built:
1998
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

Professional pictures coming! This roomy 2 bedroom, 2.5 bathroom end unit has been completely painted in a beautiful neutral shade and has new carpet throughout, as will be getting new flooring in the kitchen. A propane fireplace highlights the great room for cozy chilly 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 to 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 great place to live!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,073
Status:
NEW LISTING
MLS#:
MDQA2015528
Type:
Condo
Subdivision:
Bayside
Year built:
1996
Courtesy: Maryland Residential Management Co 410-451-3300
View additional info

ADDITIONAL INFORMATION

Beautifully maintained first-floor condominium offering serene lake views and an open, inviting floor plan. This residence features two spacious bedrooms and two full bathrooms. The light-filled living and dining areas provide direct access to a private patio overlooking the lake, perfect for enjoying peaceful mornings. Located in a highly desirable community of Bayside, offering exceptional amenities including scenic walking trails, a clubhouse with a party room, fitness center, swimming pool, and tennis courts. Conveniently situated near shopping, dining, and major commuter routes, this home offers the perfect blend of comfort, convenience, and resort-style living.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,100
Status:
NEW LISTING
MLS#:
MDQA2015692
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:
6
Baths:
5.00
Sq.Ft.:
4,165
Status:
NEW LISTING
MLS#:
MDQA2015674
Type:
Single Family-Detached
Subdivision:
Gibsons Grant
Lot size:
0.17 Acres
Year built:
2010
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

Start the New Year as a resident of Gibson’s Grant!?Discover over 4,100 sq. ft. of high-end, custom elegance in this exceptional Eastern Shore home—perfectly located in one of Chester’s most sought-after waterfront communities. With 6 bedrooms, 4.5 baths, and designer touches at every turn, this residence offers the space, craftsmanship, and lifestyle today’s buyers crave. Step inside the welcoming foyer and take in the three-story staircase, striking wrought-iron railings, and extensive architectural details including wainscoting, custom trim, and three-piece crown molding throughout. Rich hand-scraped wide-plank hardwoods lead you through thoughtfully designed spaces, including a sitting room, private office, and formal dining room. The bright and beautiful gourmet kitchen features gleaming quartz, stainless steel appliances, double ovens, under-cabinet lighting, and custom designer touches at every turn. Storage and function abound, with walk-in spaces and built-ins ready for you! With six bedrooms and 4.5 baths, this home offers flexibility for multi-generational living, guests, work-from-home setups, or hobby spaces. The finished bonus room above the oversized three-car garage includes a full bath—ideal for an au pair suite, guest retreat, or studio. The third-floor loft, also complete with a full bath, adds yet another layer of functional, finished living space. Additional features include plantation shutters, a dedicated mudroom, & second-floor laundry, Outside, enjoy extensive hardscaping that creates a turnkey, low-maintenance lifestyle—perfect for relaxing after a day on the water or at work. All of this is just a short walk to Gibson’s Grant’s impressive amenities: pool, clubhouse, fitness center, pier, playground, bocce ball, and direct access to the Cross-Island Trail. The Bay Bridge only 5 minutes away, making work commutes, weekend escapes, or even a trip to the grocery store a piece of cake. A great opportunity in a highly sought-after neighborhood—don’t miss your chance to make Gibson’s Grant your new home!

Beds:
4
Baths:
2.00
Sq.Ft.:
1,980
Status:
NEW LISTING
MLS#:
MDQA2015672
Type:
Single Family-Detached
Subdivision:
Marling Farms
Lot size:
0.37 Acres
Year built:
1954
Courtesy: The KW Collective 443-574-1600
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ADDITIONAL INFORMATION

Welcome to 1701 Bayside Dr, a beautifully updated rancher offering direct, unobstructed waterviews of Crab Alley Bay. The main home features 3 bedrooms and 1 full bath, highlighted by LVP flooring throughout, a gorgeous updated kitchen with granite countertops, and spacious living and family rooms—each with water views. The primary bedroom is generously sized with two closets. Two generously sized bedrooms, a full bathroom, and a full laundry room complete the main house. Connected by a breezeway, the property also includes a 1-bedroom, 1-bath guest suite with a full kitchen, perfect for extended family or guests. Situated on a corner lot directly across from public water access, you’ll enjoy forever-protected views from your deck and patio plus access to the pier, ramp, playground, grills, and gazebo. Major updates in 2022 include the roof, ductless heating/AC, propane baseboard heating, and windows. One car garage with plenty of parking in the driveway! Enjoy the best of Eastern Shore living in this beautifully maintained waterfront gem!

Beds:
1
Baths:
1.00
Sq.Ft.:
724
Status:
NEW LISTING
MLS#:
MDQA2015650
Type:
Condo
Subdivision:
Queens Landing
Year built:
1983
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

WATERFRONT !!! Spectacular sunrise views on display over the Chester River from this cozy 1 bedroom, 1 bath condo in the popular community of Queens Landing. Known for its amenities, you are sure to enjoy living here whether as a full-time resident or just to have as a week-end getaway! Minutes from the Bay Bridge, you can be here without ever getting on route 50! Amenities are as follows: tennis courts, waterside pool, jogging path with easy access to the cross-island running/bike trail, racquet ball court, fitness center and more!! There is also a party room that you can use when you need more room to entertain guests! This condo unit has a very low condo fee of $189 per month! Not many of these units were built and definitely not many with the sunrise view of this one. Come see it...you will be glad you did! Also for rent on a short or long-term basis: MDQA2015652.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,747
Status:
NEW LISTING
MLS#:
MDQA2015644
Type:
Condo
Subdivision:
Bayside Marina
Year built:
1995
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

Welcome to Bayside on Kent Island! This meticulously maintained 3-level townhome offers beautiful pond views and numerous updates throughout. Main level features an open floorplan with hardwood bamboo floors and upgraded lighting, Bright kitchen with white shaker cabinets, granite counters (2019), and updated fixtures. Upper level includes an oversized Primary Suite with a spa-like bath (2018), large walk-in closet with California Closets (2024 – $12K), and ceiling fan. Second bedroom features a large closet and is adjacent to the updated hall bath. Entry-level 3rd bedroom/office offers custom built-ins (2024) and direct access to the patio with serene pond views. Enjoy outdoor living on the Trex deck (approx. 4 years old) overlooking the water. Community amenities include a pool, clubhouse, tennis courts, and walking paths. Walk to local restaurants and the marina, with boat slips available. Close to the Cross Island Trail, parks, and beaches. Move-in ready and perfectly positioned to enjoy all that Kent Island living has to offer!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,830
Status:
NEW LISTING
MLS#:
MDQA2015660
Type:
Single Family-Detached
Subdivision:
Marling Farms
Lot size:
0.54 Acres
Year built:
1973
Courtesy: Cottage Street Realty LLC 703-242-0005
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ADDITIONAL INFORMATION

Discover a true waterfront treasure on .54 acres with 110 feet of waterfront. This beautifully renovated 3-bedroom, 2.5 bath home offers an open-concept layout design to capture breathing taking water views that stretch endless across the horizon. Each evening brings magnificent, direct sunset views-- the kind that make you stop, breathe, and take it all in. New pier in 2020! Step inside to luxury plank flooring that flows throughout the home, complementing a bright, modern kitchen outfitted with brilliant white quartz countertops, all new stainless steel appliances, abundant white cabinetry, and generous workspace ideal for cooking and entertaining. The refined design continues into each bathroom, where matching quartz countertops and coordinated cabinetry create a polished, cohesive aesthetic. With its expansive lot, serene waterfront setting, and elegant interior updates, this is a rare opportunity to own a home that blends comfort, beauty, and unforgettable views.

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
View additional info

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
View additional info

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:
2
Baths:
2.00
Sq.Ft.:
1,993
Status:
Active
MLS#:
MDQA2015498
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.16 Acres
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The To Be Built Home offers effortless single-level living with thoughtful spaces designed for both comfort and style. Featuring 2 bedrooms, 2 baths, and a 2-car garage, this home blends functionality with refined details throughout. A private home office provides the perfect space for productivity, while the stylish kitchen—complete with a large center island and spacious pantry—flows seamlessly into the great room, ideal for entertaining or relaxing. Sliding doors open to a covered patio, extending your living space outdoors. The luxurious primary suite features an oversized walk-in closet and a palatial bath with split vanities for a truly spa-like retreat. A convenient HovHall off the garage helps keep the home organized and clutter-free, enhancing everyday ease. For a full list of included features, please contact our sales representatives. Photos are for illustrative purposes only and may not represent the exact home or finishes available. Welcome to a new luxury active adult 55+ community on Maryland's Chesapeake Bay. Discover the amenity-filled, resort-style experience within 45 miles of Washington DC and Baltimore. Residents can take advantage of the community's 24,000 sq. ft. clubhouse with indoor & outdoor pools, a state-of-the-art fitness center, and multiple tennis and pickleball courts. With a full-time lifestyle director on site the community also features a well-maintained calendar of activities such as walking club, indoor and outdoor yoga sessions, mahjong club, kayaking, pickleball and more. Kent Island life is about making friends and enjoying the company of people who have worked hard and now want to enjoy all that a luxury 55+ community has to offer. Located steps from the water and minutes from Annapolis, the location also offers quick access to Rt. 50. Enjoy the convenience of nearby dining and shopping options together with the quaint charm of a small town.

Beds:
3
Baths:
4.00
Sq.Ft.:
2,076
Status:
Active
MLS#:
MDQA2015460
Type:
Condo
Subdivision:
Bayside
Year built:
2001
Courtesy: TTR Sotheby's International Realty 410-673-3344
View additional info

ADDITIONAL INFORMATION

This beautifully maintained 3-bedroom, 3.5-bath marina-front townhouse with a 1-car garage offers the perfect blend of comfort, convenience, and Chesapeake lifestyle. Ideally located in the heart of Kent Island, you’ll enjoy stunning marina and Chester River views from multiple levels. The main floor features new luxury vinyl plank flooring, an open-concept kitchen, dining, and family room, and a gas fireplace. French doors open to a private deck where you can relax and watch the boats go by. Upstairs, the primary suite includes a walk-in closet, a spa-like bath with a jetted tub and separate shower, and a private balcony overlooking the water. A second bedroom on this level offers its own en-suite bath and new carpet throughout. The third-floor loft bedroom is a serene retreat with a closet, full en-suite bath, and sweeping marina views. The Bayside community offers resort-style amenities including a clubhouse, fitness center, pool, and tennis courts. Plus, Castle Marina is just steps away—keep your boat right out your back door and enjoy easy access to the Chester River and beyond. Experience low-maintenance, waterfront living at its best on Kent Island!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,550
Status:
Active
MLS#:
MDQA2014682
Type:
Condo
Subdivision:
Queens Landing
Year built:
1993
Courtesy: Taylor Properties 301-970-2447
View additional info

ADDITIONAL INFORMATION

Accepting backup contracts! Enjoy resort style living every day in the gorgeous waterfront condo. Watch the sun & moon rise as you sip your favorite beverage. This sought after townhome/condo has extensive view of the Chester River & Eastern Neck Island. The owner has updated & made this place like no other. Soundproof quiet rock, custom barn doors throughout, gourmet kitchen with granite counters, soft close maple cabinets, Acacia wood floors, newer HVAC, remote full blind for back windows (heat & light senses), custom plantation blinds, bathrooms boasts stone walls, custom ceramic, jacuzzi tub, walk in shower, keypad entry door, remote awning that senses wind, hardscapes to enjoy the views and so much more! The cross island bike/hike trail is nearby along with restaurants, medical and shopping. Come check out this amazing place! All reasonable offers considered.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,250
Status:
Active
MLS#:
MDQA2015496
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.28 Acres
Year built:
2025
Courtesy: Coldwell Banker Waterman Realty 410-643-5005
View additional info

ADDITIONAL INFORMATION

New home being built! Act now and pick all your colors! Finished models can be seen! Call agent for details.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,073
Status:
Active
MLS#:
MDQA2014614
Type:
Condo
Subdivision:
Bayside Marina
Year built:
2000
Courtesy: TTR Sotheby's International Realty 410-673-3344
View additional info

ADDITIONAL INFORMATION

Welcome to this bright and inviting 2-bedroom, 2-bathroom lower-level end unit condo, ideally located in a desirable water-oriented community on Kent Island! The open living and dining area flows seamlessly into a galley-style kitchen with a breakfast bar, now updated with new granite countertops and a new stainless steel stove. The Primary suite is your private retreat, complete with a walk-in closet and a brand-new custom spa-like shower in the en-suite bath. A second bedroom and full bath provide plenty of space for family, guests, or a home office. Updates within the past few years include laminate flooring in the living areas, hallway, and baths, fresh carpet in both bedrooms and the primary closet, a modern interior paint palette, plus a newer HVAC, refrigerator, and microwave for added comfort and peace of mind. Bayside residents enjoy resort-style amenities such as a pool, tennis courts, fitness center, and clubhouse with a large party room. The unaffiliated Queens Landing Marina—just steps away—keeps your boat close, while the scenic Kent Island Trail offers miles of walking, jogging, and biking. All of this adds to the relaxed, vacation-like lifestyle of Maryland’s beautiful Eastern Shore!

Beds:
3
Baths:
3.00
Sq.Ft.:
2,583
Status:
Active
MLS#:
MDQA2014400
Type:
Single Family-Detached
Subdivision:
Four Seasons At Kent Island
Lot size:
0.14 Acres
Year built:
2021
Courtesy: RE/MAX Executive 443-274-1900
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ADDITIONAL INFORMATION

10K price reduction!!! Better Than New – $175K+ in Upgrades and Lifestyle Ready Now Four Seasons at Kent Island – Killarney with Loft Model Why wait months—and spend thousands more—for a base-level new build when you can move into your dream home today? This beautifully enhanced Killarney with Loft model in sought-after Phase I delivers over $100K in builder upgrades plus $75K in custom renovations—a total investment of $175K+—all included. To replicate this home new through the builder would exceed $1 million. For added peace of mind, the sellers are including a two-year full-service home warranty, and an invisible fence is already installed and included. Exceptional Interior & Outdoor Living The gourmet kitchen is a showstopper with a 10’ white quartz island, dry bar, SMART stainless appliances, InstaHot water dispenser, and walk-in pantry. A marble-mantled electric fireplace anchors the open-concept living area and flows to the builder-upgraded screened porch overlooking a private backyard retreat. Entertain year-round on the expansive 40' × 15' paver patio with built-in gas fire pit, gas grill, and wood-burning pizza oven—all part of the $175K+ in thoughtful upgrades that make this home truly turnkey. The spa-inspired primary suite features a fully renovated bath (2025) with new flooring, lighting, towel warmer, and upgraded fixtures. Additional highlights include Pinnacle concrete coatings on the front and screened porches, a new front door, $5K+ in custom window treatments, all-new main-level lighting, a guest en-suite, and a loft with third bedroom and full bath. A Community & Lifestyle Second to None Four Seasons at Kent Island offers a 24,000 sq ft waterfront clubhouse with indoor and outdoor pools, a fitness center, yoga studio, game room, library, tiki bar, and outdoor amphitheater. Lighted pickleball and tennis courts, bocce, a dog park, a pier with transient slips, 4+ miles of walking trails, and direct access to the Cross Island Trail complete the resort experience. A full-time lifestyle director curates events from crab feasts and live music to holiday gatherings and fitness classes. The Smarter Choice: Waiting vs. Ready Skip construction delays, surprise upgrade costs, and months of dust and noise. This home is fully finished, beautifully landscaped, and move-in ready now. Proven resale strength in an established section of the neighborhood protects your equity and provides quiet streets and friendly neighbors from day one. This is the definition of turnkey luxury—offering comfort, style, and an unmatched Chesapeake Bay lifestyle today. Schedule your private showing and experience why this home is truly better than new.

Beds:
4
Baths:
2.00
Sq.Ft.:
2,035
Status:
Active
MLS#:
MDQA2014832
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.32 Acres
Year built:
1975
Courtesy: Taylor Properties 301-970-2447
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ADDITIONAL INFORMATION

REDUCED! Opportunity Knocks Welcome to Harbor View on Kent Island - Just 7 minutes from the Bay Bridge This oversized ranch style home boasts 4 Bedrooms and 2 Full baths and is located just one block from Cox Creek. The open concept floor plan features a formal living room, large main level bedroom, hardwood flooring throughout, a modern kitchen with ample cabinetry, center island, extra counter spaces and stainless appliances. Relax in the spacious and cozy extra family room with fireplace, hearth and convenient built-ins. The adjacent spare room is the perfect spot for a home office or gym and the home is equipped with a separate convenient laundry/mudroom. Plenty of parking for family and guests in the 5 car driveway. Harbor View offers easy access to great area amenities, recreation, waterfront dining and more.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,634
Status:
Active
MLS#:
MDQA2014660
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
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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:
2
Baths:
3.00
Sq.Ft.:
1,900
Status:
Active
MLS#:
MDQA2015436
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
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ADDITIONAL INFORMATION

The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for entertaining or casual gatherings. The kitchen is beautifully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and tile backsplash, all complemented by quartz countertops for a polished look. Laminate flooring runs throughout the main living areas, with tile in both full baths for easy maintenance. The owner’s bath features a walk-in shower with seat and handheld shower wand, double sinks, and elegant quartz countertops, creating a relaxing retreat. For a full list of included features, 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#:
MDQA2015438
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

The Chester blends modern design with everyday comfort in a thoughtfully designed layout perfect for both work and relaxation. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home offers stylish finishes and smart functionality throughout. Standout features include a home office with lited French doors, an electric fireplace that adds warmth and ambiance, and a convenient dry bar for entertaining or casual gatherings. The kitchen is beautifully equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and tile backsplash, all complemented by quartz countertops for a polished look. Laminate flooring runs throughout the main living areas, with tile in both full baths for easy maintenance. The owner’s bath features a walk-in shower with seat and handheld shower wand, double sinks, and elegant quartz countertops, creating a relaxing retreat. For a full list of included features, 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#:
MDQA2015138
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2025
Courtesy: KOVO Realty 240-375-5074
View additional info

ADDITIONAL INFORMATION

This beautifully designed Chester Model Home offers sophisticated comfort and modern convenience, ready for immediate move-in with a flexible month-to-month leaseback opportunity. Featuring 2 bedrooms, 2.5 baths, and a 1-car garage, this home blends style and function seamlessly. Thoughtful touches include a fully furnished interior, a dry bar perfect for entertaining, and an electric fireplace that adds warmth and ambiance. A dedicated home office with elegant lited French doors provides the ideal space for work or creativity. The gourmet kitchen is equipped with a single oven, microwave, gas cooktop, range hood, dishwasher, pendant lighting, and a tile backsplash, all accented by quartz countertops that continue into the full baths. Enjoy laminate flooring throughout for easy maintenance, complemented by tile in the full baths. The owner’s bath offers a walk-in shower with a seat and handheld shower wand, plus double sinks and quartz counters for a spa-like retreat. For a full list of included features, please contact our sales representatives.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,610
Status:
Active
MLS#:
MDQA2015066
Type:
Single Family-Detached
Subdivision:
Castle Marina
Lot size:
0.51 Acres
Year built:
1974
Courtesy: Coldwell Banker Realty 410-263-8686
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ADDITIONAL INFORMATION

Move-in ready and full of upgrades, this thoughtfully designed home offers a bright, open layout perfect for everyday living and entertaining. The renovated kitchen features quartz counters, a coastal tile backsplash, and opens to the dining and living areas with soaring ceilings and access to the deck and fenced yard. The fire pit and mature landscaping makes for a private, serene setting. A private path through the backyard connects directly to Four Seasons and the Cross Island Trail—ideal for walking, biking, or enjoying the outdoors. The main level includes a bedroom and bonus room/office, while upstairs offers three additional bedrooms including a spacious primary suite with attached bath. Additional highlights include a two-car garage with extra storage, side gardens, tankless water heater, paved driveway with bonus parking, and no HOA. All this in a prime Kent Island location, just minutes to local shopping, dining, trails, and Rt. 50 for easy commuting to Annapolis, St. Michaels, Washington, D.C., Baltimore, and beyond. Don’t miss this opportunity to own a conveniently located, beautifully updated home in Castle Marina! Schedule your tour today - you won't want to miss this conveniently located and move in ready gem on Kent Island.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,791
Status:
Active
MLS#:
MDQA2014922
Type:
Single Family-Detached
Subdivision:
Bentons Pleasure
Lot size:
1 Acres
Year built:
2002
Courtesy: Wilson Realty & Staging LLC 410-304-2250
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ADDITIONAL INFORMATION

ATTENTION BUYERS: VA ASSUMABLE RATE of 2.49% AVAILABLE!! Discover the charm of this stunning Colonial home nestled in the desirable Bentons Pleasure neighborhood. With 2,791 sq. ft. of thoughtfully designed living space, this residence boasts four spacious bedrooms and 2.5 baths, perfect for both relaxation and entertaining. The well equipped kitchen invites culinary creativity, while the semi open floor plan seamlessly connects the dining and living areas, highlighted by a cozy fireplace. Enjoy the luxury of a soaking tub in the master bath and the convenience of walk-in closets. The home features beautiful wood floors and ceiling fans throughout, ensuring comfort year-round. Step outside to your private oasis, complete with a personal pool, ideal for summer gatherings or tranquil evenings. Located just minutes from commuter lots and an airport, this home offers easy access to local amenities, parks, and shopping. With a generous 1-acre lot and a side-entry garage, this property combines space, style, and convenience. Solar panels, too! Don't miss your chance to make this dream home yours!

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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

    $689,900
    14.5%
    change since last quarter
  • # Active listings

    99
    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