Chester MD Real Estate & Homes for Sale

98 Properties Found

Sort Results:
26–50 of 98 properties displayed
Refine Property Search
Page 1 | 2 | 3 | 4 of 4    Prev | Next
Beds:
6
Baths:
5.00
Sq.Ft.:
4,165
Status:
Active
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:
Active
MLS#:
MDQA2015672
Type:
Single Family-Detached
Subdivision:
Marling Farms
Lot size:
0.37 Acres
Year built:
1954
Courtesy: The KW Collective 443-574-1600
View additional info

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:
Active
MLS#:
MDQA2015650
Type:
Condo
Subdivision:
Queens Landing
Year built:
1983
Courtesy: Long & Foster Real Estate, Inc. 410-643-2244
View additional info

ADDITIONAL INFORMATION

EXCELLENT PRICE IMPROVEMENT ON THIS CHESTER RIVER WATERFRONT !!! Spectacular sunrise views on display over the river from this cozy 1 bedroom, 1 bath, 724 square foot, condo. Enter into an open, bright space that adjoins a well-laid out compact kitchen. The bedroom is on the waterside of the condo but either space, entry area or bedroom area, can be used as you wish. The owner chose to have the living area on the waterside. Sliding glass doors lead to a patio where you can relax with the beautiful Chester River as your view! The condo is in the popular community of Queens Landing, known for its many amenities. You are sure to enjoy living here whether as a full-time resident or just to have as a week-end or summer 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 view of this one! Come see it...you will be glad you did! Note: Conventional or conforming loans are not accepted. Freddie Mac and Fannie Mae are temporarily not approving financing loans in the community. Also for rent on a short or long-term basis: MDQA2015652. $2000 per month for year lease.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,830
Status:
Active
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
View additional info

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:
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:
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
View additional info

ADDITIONAL INFORMATION

MAJOR REDUCTION! 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
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:
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:
3
Baths:
3.00
Sq.Ft.:
2,600
Status:
Active
MLS#:
MDQA2014868
Type:
Condo
Subdivision:
Four Seasons At Kent Island
Year built:
2022
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

**** NICE VIEWS OF THE CHESTER RIVER**** ***** LOWEST PRICED SEVERN MODEL**** K Hovnanian's Four Seasons at Kent Island is an active 55+ community on Maryland's Chesapeake Bay, offering island resort-style and maintenance-free living at its finest! Shows Like a Model!!! The Severn design is a spacious and airy 3 bedroom, 2.5 bath end-unit boasting an expansive open floor plan with over 2600 square feet of luxurious living space. This home features a lavish gourmet kitchen and dining area, a huge great room with sliding door access to a large corner balcony. The centerpiece kitchen is equipped with GE Profile appliances and gas stove top. Also, quartz counters with under cabinet lighting, and oversized kitchen island. The fantastic owner's suite has an adjoining sitting room with access to the balcony, an owner's spa bath and 2 oversized walk-in closets. Two large secondary bedrooms are located in a separate wing of the home and each features a walk-in closet and share a Jack and Jill bath. There are 10 closets, and 18 windows. Additional features include a separate laundry room and powder room. Enhanced decorator details include luxury plank flooring, recessed lighting, a garage with adjoining driveway/parking space and a large personal storage room which is a few short steps from the elevator. ***** KEEP IN MIND THIS SEVERN MODEL, WITH OVER 2600 SQUARE FEET OF LUXURY LIVING SPACE, IS AVAILABLE TO YOU NOW. PRESENTLY, THERE IS A 6- 7 MONTH WAIT FOR THE COMPLETION OF NEWLY CONSTRUCTED SEVERN MODELS, BUT THIS UNIT IS MOVE-IN READY AT A MUCH LOWER PRICE WITH PLENTY OF HIGH-END DESIGNER FEATURES AND UPGRADES ALREADY INCLUDED***** Brand New 24,000 Square Foot Clubhouse with stunning Chester River Views! Fantastic amenities include an outdoor infinity pool, indoor pool with on-duty lifeguard, fitness center, library, game room, electric and wood burning fire pits, Tiki bar equipped with refrigerators, sinks and television monitors, pier with transient boat slips, paved walking paths that link to the Cross Island Trail, pickle ball & tennis courts, bocce, dog park, and an outdoor amphitheater for live music and movie nights. Easy walk from this home to the Clubhouse. The community lifestyle director will keep you busy with daily activities such as yoga, a variety of exercise classes and an assortment of clubs including biking, billiards, book club, baking, mahjong, environmental club, trivia night and more. In addition to the weekly and monthly activities, residents can enjoy crab feasts, oyster roasts, and holiday gatherings throughout the year. This development is an unrivaled, amenity-filled, resort-style experience with convenient access to Annapolis, DC, Baltimore, and BWI. Kent Island offers multiple dining and shopping options, a nearby outlet mall, and a 6.5 mile cross-island trail surrounded by views of the Chester River.

Beds:
4
Baths:
4.00
Sq.Ft.:
5,122
Status:
Active
MLS#:
MDQA2014738
Type:
Single Family-Detached
Subdivision:
Southwind
Lot size:
1.9 Acres
Year built:
1995
Courtesy: Long & Foster Real Estate, Inc. 410-721-1500
View additional info

ADDITIONAL INFORMATION

An impressive open two-story foyer welcomes you to this custom 4 BR, 3.5BA waterfront residence on 1.9 acres boasting an enchanting open space floorplan. A first floor Ensuite BR has a walk-in closet plus a separate jacuzzi and shower in the updated full bath. The sumptuous approximately 39'X26' Primary Suite with a large sitting room area offers front and rear balconies specifically designed by the Architect to enjoy the breathtaking sunrises, moonrises & sunsets lighting the Bay with bright pink and orange skies and brilliantly lit sparkling water. This second floor Primary Suite has a Cathedral ceiling, a 3-sided gas fireplace and a fully renovated Coastal style bath which includes a luxurious remote controlled floating Air Spa tub. Also upstairs is a large loft accessed by French doors boasting custom built-ins and extraordinary extensive water views overlooking the Bay and Pool. Walls of windows throughout the residence provide abundant natural light and endless broad views of Crab Alley Bay from almost every room. The Gourmand's Kitchen with its solid custom maple cabinetry is furnished with a Subzero refrigerator, double wall oven with Smart features, auto purified cold water spigot at the sink along with a 5-burner gas cooktop. A Subzero wine fridge is located in the island by the Dining Room for easy entertaining. The hardwood flooring is Canadian White Maple. A freestanding curved White Maple staircase enhances the beauty of the very generously sized 2-story Foyer. A two-story Great Room features a 2-sided gas FP and a custom wet bar that both open to a vast Morning Room area and seating space. Formal separate Dining and Living Rooms are open via knee-walls with columns for romantic dining and entertaining. The level outdoor living space includes a lighted inground 36x18' pool, a Pergola and a stone hardscape with a built-in Grill, outdoor rated refrigerator and a built-in gas fireplace for chilly waterfront evenings outdoors. Plentiful terracing affords a breathtaking, serene setting to relax and entertain friends and family while taking in the extraordinary and expansive water views. There is a private pier, a 3-car garage with built-in overhead storage and a driveway that can accommodate several more cars and there are multiple landscaping berms. The home has a whole house sound system & whole house attic fan. The cooking, 3 fireplaces and 3 zone HVAC are propane. The community of Southwind is a waterfront peninsula surrounding 97 custom homes and offering a waterfront Clubhouse, Tennis Court, walking trails along the Bay, a Boat Launch and a gated boat storage area. Welcome home to your year-round vacation! Furniture negotiable

Beds:
3
Baths:
3.00
Sq.Ft.:
2,399
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
View additional info

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:
3
Baths:
3.00
Sq.Ft.:
2,520
Status:
Active
MLS#:
MDQA2015440
Type:
Single Family-Detached
Subdivision:
Gibsons Grant
Lot size:
0.13 Acres
Year built:
2012
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

Beautiful Home in Gibson’s Grant with Elevator, Open Floor Plan & Two-Car Garage Welcome to this beautifully appointed home in the sought-after waterfront community of Gibson’s Grant on Kent Island. This residence offers a perfect blend of comfort, style, and convenience — featuring a spacious open floor plan and an attached two-car garage. No need to worry about stairs — a full elevator effortlessly transports you to the grand second-floor primary suite, complete with a cozy sitting area and private porch. Throughout the home, you’ll find thoughtful upgrades, including a gourmet kitchen with granite countertops, hardwood floors, custom trim, and elegant finishes that make this property truly special. Enjoy the charm of the screened side porch, a beautifully landscaped English-style yard with brick patio, gardens, and fencing that provides both beauty and privacy. With three bedrooms and a den that can easily serve as a fourth bedroom or home office, this home offers versatile living space for any lifestyle. You’ll also enjoy peekaboo water views and the exceptional amenities that make Gibson’s Grant so desirable. Established in 2007, this 280-home community is nestled between the Chester River and Macum Creek, offering a community pool, clubhouse, fitness center, bocce court, pier, kayak launch, and playground and much more. Conveniently located near shopping, Starbucks, restaurants, the Kent Island Cross Island Trail, and just minutes from the Bay Bridge, this home offers the best of Kent Island living.

Beds:
2
Baths:
1.00
Sq.Ft.:
832
Status:
Active
MLS#:
MDQA2015064
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.28 Acres
Year built:
1952
Courtesy: RE/MAX Executive 443-274-1900
View additional info

ADDITIONAL INFORMATION

Discover this charming 2-bedroom, 1-bath home in Harbor View featuring beautiful wood floors, a brand-new roof, updated windows, and a spacious rear deck overlooking a large fenced backyard—perfect for relaxing or entertaining while enjoying the Island lifestyle. Ideally located near restaurants, shopping, and easy access to Route 50 for commuting. Come See!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,073
Status:
Active
MLS#:
MDQA2014698
Type:
Condo
Subdivision:
Bayside
Year built:
1996
Courtesy: Engel & Volkers Ocean City 443-292-6767
View additional info

ADDITIONAL INFORMATION

This is a highly sought-after location on Kent Island, known for its limited availability. Sellers have updated shiplap in the living room, paint throughout the house. This second-floor condo offers breathtaking views of the pond. You will enjoy an updated backsplash in the kitchen, featuring granite countertops and stainless steel appliances. Hardwood flooring is throughout the house. The private deck provides additional storage closet. The HVAC system is only 2 years old,, and the association is professional managed. The updated clubhouse features a well-equipped fitness center, a second-floor party room with a kitchen, a fireplace, and decks offering beautiful views. Tennis and pickleball enthusiasts will enjoy access to two dedicated courts. Water lovers will appreciate the close proximity to Castle Marina, which provides boat slips and amenities with direct access to the river and the bay. Trail enthusiasts will also value the connection to the scenic Cross Island Trail via Castle Marina Road—a picturesque path stretching from the Chesapeake Bay to Kent Narrows, ideal for walking, biking, and enjoying the waterfront surroundings.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,728
Status:
Active
MLS#:
MDQA2015554
Type:
Single Family-Detached
Subdivision:
Harbor View
Lot size:
0.35 Acres
Year built:
1991
Courtesy: Coldwell Banker Realty 410-224-2200
View additional info

ADDITIONAL INFORMATION

Discover this beautifully updated 3-bedroom, 2 full and 1 half bathroom home located on a scenic 0.35-acre corner lot in the highly desirable Harbor View community, just two miles east of the Chesapeake Bay Bridge. Inside, enjoy a bright, modern kitchen with new countertops and backsplash, hardwood floors on the main and upstairs evels, and cathedral ceiling with skylights. Relax in the spacious lower-level family room plus a versatile bonus room/office/bedroom. Recent upgrades include a new roof (2019) with 50-year shingles, new windows, and a new vinyl pool liner with warranty. Step outside to your fully fenced back yard and private in-ground pool and deck, perfect for summer entertaining and relaxing. The community offers a one-acre community field with a pavilion and playground for events and gatherings. The location offers unbeatable convenience—just 20 minutes to Annapolis, 45 minutes to Baltimore, and 50–60 minutes to Washington, D.C. Enjoy the best of Kent Island living with easy access to Kent Narrows for waterfront dining, the Cross Island Trail (6.5 miles long) for walking and biking, and Queenstown Premium Outlets just five minutes away. This move-in-ready home offers the perfect blend of comfort, location, and lifestyle—don’t miss your chance to make it yours!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,440
Status:
Active
MLS#:
MDQA2015054
Type:
Condo
Subdivision:
Queens Landing
Year built:
1999
Courtesy: Douglas Realty, LLC 410-255-3690
View additional info

ADDITIONAL INFORMATION

Settlement possible for the Holidays & New Year! Enjoy low-maintenance living in the desirable waterfront community of Queen’s Landing, offering scenic views and direct access to the Chester River via Northeast Bay. This beautifully updated home features expansive pond and fountain views the moment you walk in, along with a brand new kitchen showcasing shaker-style cabinetry, quartz countertops, and stainless steel appliances. Brand new Living Room carpet. Upstairs offers two spacious en-suite bedrooms, including a primary suite with vaulted ceilings. A laundry area with brand new washer and dryer is conveniently located between the bedrooms. Light-filled interior with large windows and a screened-in porch perfect for relaxing evenings. Community amenities include a private marina, heated outdoor pool, renovated clubhouse, fitness center, tennis/pickleball courts, indoor racquetball, kayak launch/storage, and waterfront walking trails. Lawn care, snow removal, and exterior maintenance included. A boater’s dream and peaceful retreat—schedule your showing today!

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
View additional info

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:
4
Baths:
6.00
Sq.Ft.:
3,460
Status:
Active
MLS#:
MDQA2015546
Type:
Single Family-Detached
Subdivision:
Southwind
Lot size:
1 Acres
Year built:
1989
Courtesy: TTR Sotheby's International Realty 410-280-5600
View additional info

ADDITIONAL INFORMATION

Set within Southwind, one of Kent Island’s most sought-after waterfront communities, this exceptional residence offers an elegant blend of craftsmanship and comfort with 10 foot ceilings and beautiful crown molding. Perfectly sited on an acre overlooking Crab Alley Bay and Eastern Bay, the home’s peaceful setting is enhanced by sweeping water views, mature landscaping, and a private waterside pool that invites year-round enjoyment. Inside, timeless design meets modern refinement. The first-floor primary suite provides a serene retreat, joined by two additional guest suites on the main level—each with its own ensuite bath for privacy and comfort. Upstairs, a fourth bedroom and full bath accompany a spacious living area, ideal for extended family or guests. The heart of the home is a stunning, renovated kitchen featuring rich finishes, premium appliances, and an open layout perfect for gathering. Gleaming hardwood floors flow throughout, leading to a mahogany-lined library that exudes warmth and sophistication—a true sanctuary for work or quiet reflection. Outdoor living takes center stage with a screened porch that captures cooling Bay breezes and views of the pool and shimmering water beyond. Whether entertaining or simply savoring the stillness of the shoreline, every space in this home celebrates the beauty of the Chesapeake Bay lifestyle.

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
View additional info

ADDITIONAL INFORMATION

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: 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!

Refine Property Search
Page 1 | 2 | 3 | 4 of 4    Prev | Next
26–50 of 98 properties displayed
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

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.



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

    $692,400
    14.5%
    change since last quarter
  • # Active listings

    104
    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