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Newest Homes for Sale in Chester, MD

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  • 807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    807 Auckland Way, Chester, MD 21619
    /47

    $425,500

    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    807 Auckland Way, Chester, MD 21619

    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

    David Moore Real Broker, LLC

    807 Auckland Way, Chester, MD 21619
  • 108 Carriage Heath, Chester, MD 21619
    108 Carriage Heath, Chester, MD 21619
    108 Carriage Heath, Chester, MD 21619
    /81

    $1,350,000

    Open Sat 12PM - 2PM
    • 5 Beds
    • 3.5 Baths
    • 4,334 Sq Ft

    108 Carriage Heath, Chester, MD 21619

    Welcome to this exceptional coastal retreat in the sought-after community of Gibson’s Grant on Kent Island, offering expansive views of the community pond and Macum Creek. Blending timeless architectural details with modern updates, this beautifully appointed home delivers luxury waterfront living in one of Kent Island’s most desirable neighborhoods.At the heart of the home, the open-concept

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 382-9517

    108 Carriage Heath, Chester, MD 21619
  • 232 Evelyne St, Chester, MD 21619
    232 Evelyne St, Chester, MD 21619
    232 Evelyne St, Chester, MD 21619
    /35

    $865,000

    • 4 Beds
    • 3.5 Baths
    • 3,312 Sq Ft

    232 Evelyne St, Chester, MD 21619

    Situated on one of the largest lots in sought-after Gibson’s Grant, this 4-bedroom, 3.5-bath home offers space, flexibility, and room to grow. High ceilings and an open layout create an airy feel, with an oversized kitchen flowing seamlessly into the family room and a separate main-level office for work or quiet retreat. The main level also features a formal dining room and living room. Upstairs,

    Courtney Chipouras TTR Sotheby's International Realty

    232 Evelyne St, Chester, MD 21619
  • 162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    162 Kirwans Landing Ln, Chester, MD 21619
    /103

    $1,325,000

    Open Sat 2PM - 4PM
    • 5 Beds
    • 3 Baths
    • 3,000 Sq Ft

    162 Kirwans Landing Ln, Chester, MD 21619

    Waterfront Living in Kirwan’s Landing! Set on 1.4 beautifully landscaped acres, this designer-renovated five-bedroom residence with pool and private pier blends elevated coastal style with resort-inspired outdoor living. The outdoor setting feels like a private resort, featuring an oversized saltwater pool with a newly hardscaped stone deck, mature landscaping, fruit trees, and peaceful water

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 446-1537

    162 Kirwans Landing Ln, Chester, MD 21619
  • 129 Wheelhouse Way Unit 11, Chester, MD 21619
    129 Wheelhouse Way Unit 11, Chester, MD 21619
    129 Wheelhouse Way Unit 11, Chester, MD 21619
    /42

    $585,000

    Coming Soon
    • 2 Beds
    • 2.5 Baths

    129 Wheelhouse Way Unit 11, Chester, MD 21619

    Professional photos coming! Welcome to one of the most desirable locations in Four Seasons at Kent Island, where luxury, convenience, and resort-style living come together in a way that few homes in the community can offer. This beautifully upgraded first-floor Chester model is not only one of the closest residences to the Chester River, but also enjoys a premium location just one building away

    Jennifer Thomas RE/MAX Executive

    129 Wheelhouse Way Unit 11, Chester, MD 21619
  • 2812 Harvest Ct, Chester, MD 21619
    2812 Harvest Ct, Chester, MD 21619
    2812 Harvest Ct, Chester, MD 21619
    /68

    $1,100,000

    Open Sat 10AM - 12PM
    • 4 Beds
    • 3 Baths
    • 3,017 Sq Ft

    2812 Harvest Ct, Chester, MD 21619

    Welcome to this pristine contemporary ranch in the coveted waterfront community of South Wind on Kent Island, where luxury, comfort, and resort-style living come together on 1.21 beautifully landscaped acres. From the moment you arrive, the home’s lush green lawn, vibrant gardens, and custom walkways create a picture-perfect setting worthy of a magazine cover. Inside, the open-concept floor plan

    Darlene Winegardner RE/MAX Executive

    2812 Harvest Ct, Chester, MD 21619
  • 106 Bodys Neck Rd, Chester, MD 21619
    106 Bodys Neck Rd, Chester, MD 21619
    106 Bodys Neck Rd, Chester, MD 21619
    /17

    $435,000

    • 3 Beds
    • 2.5 Baths
    • 1,595 Sq Ft

    106 Bodys Neck Rd, Chester, MD 21619

    Welcome to Bayside, where coastal living and resort-style amenities come together in one of the area’s most desirable waterfront communities. This 3-bedroom, 2.5-bath condo offers a relaxing marina-side setting with both upper and lower decks overlooking the marina, creating the perfect backdrop for morning coffee, evening sunsets, and everything in between. Inside, you’ll find a spacious layout

    Bill Longest Realty Navigator

    106 Bodys Neck Rd, Chester, MD 21619
  • 121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    121 Kinglet Ct, Chester, MD 21619
    /41

    $969,990

    New Construction $130K PRICE DROP
    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    121 Kinglet Ct, Chester, MD 21619

    Efficient kitchen featuring white cabinetry & quartz countertops.Open concept living area with vaulted ceiling & cozy fireplace.Pristine primary suite with stylish feature wall & ceiling treatment.Refreshing primary bath featuring a freestanding tub & brushed nickel finishes.Private Extra Suite & home office off foyer.Inviting screened patio for relaxing with

    K. Hovnanian Homes Builder
    121 Kinglet Ct, Chester, MD 21619
  • 307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    307 Kingfisher Ln, Chester, MD 21619
    /29

    $899,990

    New Construction $80K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    307 Kingfisher Ln, Chester, MD 21619

    Welcoming foyer leads to beautiful open concept floorplan.Inviting kitchen featuring white cabinetry, quartz countertops, & center island.Spacious great room with cozy fireplace, perfect for spending time with family.Tranquil primary suite featuring detailed ceiling treatment.Polished primary bath with brushed nickel finishes & generous walk-in closet.Convenient Extra Suite &

    K. Hovnanian Homes Builder
    307 Kingfisher Ln, Chester, MD 21619
  • 711 Warbler Way, Chester, MD 21619
    711 Warbler Way, Chester, MD 21619
    711 Warbler Way, Chester, MD 21619
    /15

    $789,990

    New Construction $82K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,791 Sq Ft

    711 Warbler Way, Chester, MD 21619

    Beautiful kitchen with white cabinetry & glass-front uppers.Vast island & countertops for preparing meals.Elegant dining area for hosting special dinners.Incredible great room featuring stunning fireplace.Serene primary suite with gorgeous ceiling moulding.Lavish primary bath featuring freestanding white vanities.Screened patio off the great room extends living space

    K. Hovnanian Homes Builder
    711 Warbler Way, Chester, MD 21619
  • 719 Warbler Way, Chester, MD 21619
    719 Warbler Way, Chester, MD 21619
    719 Warbler Way, Chester, MD 21619
    /15

    $829,990

    New Construction $60K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,807 Sq Ft

    719 Warbler Way, Chester, MD 21619

    Polished kitchen with white cabinets & glass-front uppers.Vast island & quartz countertops for prep & dining.Welcoming great room featuring elegant fireplace.Screened patio with direct access to the great room.Charming dining area for mealtime enjoyment.Lavish primary suite & bath with dual vanities & feature wall.Private home office for leisure activities.

    K. Hovnanian Homes Builder
    719 Warbler Way, Chester, MD 21619
  • 132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    132 Wheelhouse Way Unit 11, Chester, MD 21619
    /29

    $780,000

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    132 Wheelhouse Way Unit 11, Chester, MD 21619

    Experience everything Four Seasons has to offer without the wait. This meticulously maintained home shows like new and is located just steps from the community amenities and vibrant social spaces that make Four Seasons so desirable. 132 Wheelhouse Way is arguably one of the most sought-after locations in the community, offering fantastic water views and convenient ground-level access. Simply step

    Matthew Arnold Real Broker, LLC

    132 Wheelhouse Way Unit 11, Chester, MD 21619
  • 212 Switchgrass Way Unit 34, Chester, MD 21619
    212 Switchgrass Way Unit 34, Chester, MD 21619
    212 Switchgrass Way Unit 34, Chester, MD 21619
    /40

    $770,000

    • 3 Beds
    • 2.5 Baths

    212 Switchgrass Way Unit 34, Chester, MD 21619

    Professional photos coming! Experience elevated Eastern Shore living in this beautifully appointed corner residence overlooking the Chester River in the sought-after 55+ waterfront community of K. Hovnanian’s Four Seasons at Kent Island. Just one year old and impeccably maintained, this spacious three-bedroom, two-and-a-half-bath home offers more than 2,600 square feet of upscale living with the

    Jennifer Thomas RE/MAX Executive

    212 Switchgrass Way Unit 34, Chester, MD 21619
  • 5011 Bridgepointe Dr, Chester, MD 21619
    5011 Bridgepointe Dr, Chester, MD 21619
    5011 Bridgepointe Dr, Chester, MD 21619
    /46

    $374,900

    • 3 Beds
    • 2.5 Baths
    • 1,302 Sq Ft

    5011 Bridgepointe Dr, Chester, MD 21619

    Nestled in the heart of Kent Island, this charming 3 Bedroom, 2 Full Bathroom townhome with Bonus Room, offers the perfect blend of comfort, convenience, and peaceful surroundings. Located in the desirable Bridgepointe community, this home features major updates including a newer roof, HVAC system, and water heater providing peace of mind for years to come. Enjoy a private backyard setting that

    Nick Waldner Keller Williams Realty Centre

    5011 Bridgepointe Dr, Chester, MD 21619
  • 102 Boatswain Way Unit 44, Chester, MD 21619
    102 Boatswain Way Unit 44, Chester, MD 21619
    102 Boatswain Way Unit 44, Chester, MD 21619
    /19

    $1,069,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 44, Chester, MD 21619

    Stylish kitchen finished with designer cabinetry & a spacious island.Light-filled great room highlighted by an electric fireplace.Dining space made for hosting, complete with a convenient dry bar.Owner’s suite featuring a separate sitting room & two walk-in closets for added storage.Owner’s spa bath showcasing dual sinks & a sleek frameless shower enclosure.Private balcony

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 44, Chester, MD 21619
  • 102 Boatswain Way Unit 31, Chester, MD 21619
    102 Boatswain Way Unit 31, Chester, MD 21619
    102 Boatswain Way Unit 31, Chester, MD 21619
    /20

    $1,019,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 31, Chester, MD 21619

    Chef-inspired gourmet kitchen showcasing designer cabinetry & a statement center island.Open great room anchored by an electric fireplace for everyday comfort.Dining area enhanced by a built-in dry bar for effortless entertaining.Private owner’s retreat with an adjoining sitting room & dual walk-in closets.Spa-style owner’s bath featuring dual sinks & a frameless shower

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 31, Chester, MD 21619
  • 102 Boatswain Way Unit 24, Chester, MD 21619
    102 Boatswain Way Unit 24, Chester, MD 21619
    102 Boatswain Way Unit 24, Chester, MD 21619
    /20

    $819,990

    New Construction
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 24, Chester, MD 21619

    Beautiful gourmet kitchen with designer cabinetry & center island.Electric fireplace adds warmth to spacious great room.Charming dining area featuring convenient dry bar.Peaceful owner's suite with cozy sitting room & walk-in closets.Refreshing owner's spa bath with dual sinks & frameless shower door.Inviting balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 24, Chester, MD 21619
  • 102 Boatswain Way Unit 43, Chester, MD 21619
    102 Boatswain Way Unit 43, Chester, MD 21619
    102 Boatswain Way Unit 43, Chester, MD 21619
    /31

    $929,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 43, Chester, MD 21619

    Beautiful gourmet kitchen featuring designer cabinetry & an efficient layout for everyday living.Bright great room with an electric fireplace adding warmth & character.Dining area complemented by a convenient dry bar for easy entertaining.Private owner’s suite with walk-in closet & direct access to the spa bath.Home office with double doors ideal for work or quiet

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 43, Chester, MD 21619
  • 1331 Calvert Rd, Chester, MD 21619
    1331 Calvert Rd, Chester, MD 21619
    1331 Calvert Rd, Chester, MD 21619
    /48

    $479,900

    $20K PRICE DROP
    • 4 Beds
    • 3 Baths
    • 2,542 Sq Ft

    1331 Calvert Rd, Chester, MD 21619

    Welcome to this spacious 4 bedroom, 3 bathroom split-level home in Chester, MD, filled with natural light and offering a flexible layout perfect for everyday living. The first floor features a comfortable living area, large utility room, full bathroom, and two bedrooms. Upstairs, you’ll find a large kitchen with plenty of cabinet space, a dining room located just off the kitchen, and a bright

    Pamela Price Berkshire Hathaway HomeServices PenFed Realty

    1331 Calvert Rd, Chester, MD 21619
  • 536 Warbler Way, Chester, MD 21619
    536 Warbler Way, Chester, MD 21619
    536 Warbler Way, Chester, MD 21619
    /9

    $849,990

    New Construction
    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft

    536 Warbler Way, Chester, MD 21619

    Polished kitchen featuring white cabinetry, quartz countertops, & center island.Open concept living areas with a vaulted ceiling & cozy fireplace.Private primary suite featuring a stylish ceiling treatment & walk-in closet.Refreshing primary bath with dual vanities & matte black finishes.Formal home office offers a quiet space for working.Versatile screened patio for relaxing

    K. Hovnanian Homes Builder
    536 Warbler Way, Chester, MD 21619
  • 540 Warbler Way, Chester, MD 21619
    540 Warbler Way, Chester, MD 21619
    540 Warbler Way, Chester, MD 21619
    /26

    $949,990

    New Construction $21K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 2,772 Sq Ft

    540 Warbler Way, Chester, MD 21619

    Elegant kitchen featuring white cabinetry & glass-front uppers.Vast center island, perfect for prepping family meals.Stunning fireplace adds character & warmth to spacious great room.Lavish primary suite & bath featuring bath barn door.Secluded Extra Suite for overnight guests.Functional home office for leisure activities.Cozy screened patio for outdoor relaxation.

    K. Hovnanian Homes Builder
    540 Warbler Way, Chester, MD 21619
  • 6005 Bridgepointe Dr, Chester, MD 21619
    6005 Bridgepointe Dr, Chester, MD 21619
    6005 Bridgepointe Dr, Chester, MD 21619
    /38

    $362,900

    • 3 Beds
    • 2.5 Baths
    • 1,302 Sq Ft

    6005 Bridgepointe Dr, Chester, MD 21619

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

    Megan Rosendale Rosendale Realty

    6005 Bridgepointe Dr, Chester, MD 21619
  • 108 Price Rd, Chester, MD 21619
    108 Price Rd, Chester, MD 21619
    108 Price Rd, Chester, MD 21619
    /10

    $240,000

    • 3 Beds
    • 2 Baths
    • 1,160 Sq Ft

    108 Price Rd, Chester, MD 21619

    You wouldn't think it but the property offers 3 bedroom and 2 full baths. Patio right off kitchen for the summer cookouts! Easy yard maintenance here, not much grass to manage, leaves plenty of time for those cookouts. Close to Route 8 for easy east/west access. Property sold as is, no repairs will be made by seller. HUD CASE 244-032645, reach out for more information on this unique buying

    Dana Byrd Thurston Wyatt Real Estate, LLC

    108 Price Rd, Chester, MD 21619
  • 265 Evelyne St, Chester, MD 21619
    265 Evelyne St, Chester, MD 21619
    265 Evelyne St, Chester, MD 21619
    /54

    $640,000

    Open Sat 4PM - 6PM
    • 3 Beds
    • 2.5 Baths
    • 2,119 Sq Ft

    265 Evelyne St, Chester, MD 21619

    Welcome to 265 Evelyne Street in the sought-after waterfront community of Gibsons Grant! Offering nearly 2,200 square feet of living space, this beautifully maintained home combines coastal charm with modern comfort. Inside, you’ll find hardwood floors, a spacious open-concept layout, and a beautifully appointed kitchen featuring a large island, gas stove, double oven, and plenty of space for

    Kathleen Higginbotham Samson Properties

    265 Evelyne St, Chester, MD 21619
  • 54 D Queen Caroline Ct, Chester, MD 21619
    54 D Queen Caroline Ct, Chester, MD 21619
    54 D Queen Caroline Ct, Chester, MD 21619
    /38

    $365,000

    $19K PRICE INCREASE
    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54 D Queen Caroline Ct, Chester, MD 21619

    Discover refined waterfront community living in this beautifully updated and rarely available 3-bedroom, 2.5-bath condo in the highly desirable Queen’s Landing community. Thoughtfully designed with both comfort and style in mind, this spacious home offers fresh interior paint, an inviting open layout, and a beautifully updated kitchen featuring elegant quartz countertops—perfect for everyday

    Michelle DiDonato Island Realty, LLC

    54 D Queen Caroline Ct, Chester, MD 21619
  • 45G Queen Neva Ct, Chester, MD 21619
    45G Queen Neva Ct, Chester, MD 21619
    45G Queen Neva Ct, Chester, MD 21619
    /40

    $349,500

    • 2 Beds
    • 2.5 Baths
    • 1,312 Sq Ft

    45G Queen Neva Ct, Chester, MD 21619

    Seller is offering closing cost assistance for qualified buyers! This charming townhouse in Queens Landing offers a perfect blend of comfort and community amenities. Step inside to discover a traditional floor plan featuring a cozy living room off the eat-in kitchen, with a separate family room ideal for gatherings. The home boasts two spacious bedrooms and 2.5 baths, including a primary bath for

    John Freeman Coldwell Banker Realty

    45G Queen Neva Ct, Chester, MD 21619
  • 190 Harrier Way Unit 21, Chester, MD 21619
    190 Harrier Way Unit 21, Chester, MD 21619
    190 Harrier Way Unit 21, Chester, MD 21619
    /73

    $649,900

    • 3 Beds
    • 2.5 Baths
    • 2,639 Sq Ft

    190 Harrier Way Unit 21, Chester, MD 21619

    Impeccably finished and immediately available, this corner residence provides the ease and comfort of luxury condo living surrounded by the natural beauty of the Chesapeake Bay landscape. Windows on three sides fill more than 2600 square feet with natural light, while the peaceful pond-to-river setting creates a backdrop of fountains, wildlife, and winter water views beyond. Secure building

    Timothy McIntyre The KW Collective

    190 Harrier Way Unit 21, Chester, MD 21619
  • 330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    330 Serenity Ln, Chester, MD 21619
    /50

    $5,900,000

    • 7 Beds
    • 9 Baths
    • 9,974 Sq Ft

    330 Serenity Ln, Chester, MD 21619

    Designed to rival a private resort, the outdoor spaces were made for celebrating with family and friends. Sweeping water views set the stage for unforgettable gatherings. The waterfront pool features a cascading natural rock waterfall with a bench tucked underneath and a generous shallow sun shelf. A beautifully appointed pool house offers a covered summer kitchen, bar, seating area and full bath

    Brad Kappel TTR Sotheby's International Realty

    330 Serenity Ln, Chester, MD 21619
  • 110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    110 Boatswain Way Unit 42, Chester, MD 21619
    /32

    $789,990

    New Construction $70K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    110 Boatswain Way Unit 42, Chester, MD 21619

    Gourmet kitchen with designer cabinetry & vast center island. Inviting great room featuring a cozy electric fireplace. Dry bar creates a polished space for serving & entertaining. Peaceful owner's suite with stylish tray ceiling & private bath. Home office with double doors offers a quiet, flexible workspace. Balcony extends the living space outdoors for relaxing or unwinding.

    K. Hovnanian Homes Builder
    110 Boatswain Way Unit 42, Chester, MD 21619
  • 102 Boatswain Way Unit 21, Chester, MD 21619
    102 Boatswain Way Unit 21, Chester, MD 21619
    102 Boatswain Way Unit 21, Chester, MD 21619
    /21

    $869,990

    New Construction $32K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 21, Chester, MD 21619

    Gourmet kitchen with spacious central island & sleek finishes. Dining area with built-in dry bar for easy entertaining. Bright great room with electric fireplace & open layout. Private balcony just off the great room. Owner’s suite with dual walk-in closets for added storage. Sitting room in owner’s suite with direct balcony access. Spa-inspired owner’s bath with dual sinks & glass-enclosed

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 21, Chester, MD 21619
  • 102 Boatswain Way Unit 42, Chester, MD 21619
    102 Boatswain Way Unit 42, Chester, MD 21619
    102 Boatswain Way Unit 42, Chester, MD 21619
    /33

    $929,990

    New Construction $33K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 42, Chester, MD 21619

    Home office with lighted French doors creates a private workspace. Gourmet kitchen with spacious central island anchors the layout. Dining area with dry bar keeps entertaining within easy reach. Great room with electric fireplace draws the space together. Balcony just off the great room offers easy outdoor access. Owner’s suite also connects to the balcony for a private outdoor retreat. Owner’s

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 42, Chester, MD 21619
  • 540 Warbler Way, Stevensville, MD 21666
    540 Warbler Way, Stevensville, MD 21666
    540 Warbler Way, Stevensville, MD 21666
    /51

    $949,990

    New Construction
    • 3 Beds
    • 3 Baths
    • 2,789 Sq Ft

    540 Warbler Way, Stevensville, MD 21666

    Welcome to the Kerr, a beautifully designed home offering 3 bedrooms, 3 baths, and a 3-car garage. This home combines an open-concept layout with thoughtful design for both comfort and functionality. The main living area features a cozy fireplace with mantel and hearth, creating a warm and inviting focal point. A dedicated home office provides a private space for productivity, while the screened

    Mary Anne Kowalewski KOVO Realty

    540 Warbler Way, Stevensville, MD 21666
  • 102 Boatswain Way Unit 12, Chester, MD 21619
    102 Boatswain Way Unit 12, Chester, MD 21619
    102 Boatswain Way Unit 12, Chester, MD 21619
    /12

    $629,990

    New Construction $34K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft

    102 Boatswain Way Unit 12, Chester, MD 21619

    Open home office for flexible work or study. Gourmet kitchen with central island at the heart of the home. Dining area with dry bar for easy entertaining. Great room with electric fireplace for a cozy focal point. Patio off the great room with direct access to the owner's suite. Owner's suite with dual closets for added storage. Owner's bath with dual sinks & glass shower enclosure. Bedroom 2

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 12, Chester, MD 21619
  • 102 Boatswain Way Unit 34, Chester, MD 21619
    102 Boatswain Way Unit 34, Chester, MD 21619
    102 Boatswain Way Unit 34, Chester, MD 21619
    /20

    $969,990

    New Construction $34K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    102 Boatswain Way Unit 34, Chester, MD 21619

    Stylish gourmet kitchen centered around a large island. Dining space with convenient dry bar for hosting. Open great room featuring an electric fireplace. Balcony extending from the main living area. Owner’s suite with two spacious walk-in closets. Private sitting area in owner’s suite with balcony connection. Owner’s bath with dual sinks & glass shower enclosure.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 34, Chester, MD 21619
  • 102 Boatswain Way Unit 32, Chester, MD 21619
    102 Boatswain Way Unit 32, Chester, MD 21619
    102 Boatswain Way Unit 32, Chester, MD 21619
    /35

    $829,990

    New Construction $35K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 32, Chester, MD 21619

    Elegant gourmet kitchen with designer cabinetry & center island. Spacious great room featuring electric fireplace. Charming dining area with dry bar for efficient serving. Serene owner's suite & spa bath with frameless shower door. Convenient home office for working remotely. Peaceful balcony for outdoor relaxation.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 32, Chester, MD 21619
  • 102 Boatswain Way Unit 33, Chester, MD 21619
    102 Boatswain Way Unit 33, Chester, MD 21619
    102 Boatswain Way Unit 33, Chester, MD 21619
    /30

    $829,990

    New Construction $33K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    102 Boatswain Way Unit 33, Chester, MD 21619

    Private home office with elegant French doors. Chef-worthy gourmet kitchen with sprawling island. Formal dining area with dry bar, perfect for entertaining. Gorgeous great room with cozy electric fireplace. Sophisticated owner's suite with triple windows. Stunning owner's spa bath featuring split vanities. Beautiful balcony has access through primary suite & great room.

    K. Hovnanian Homes Builder
    102 Boatswain Way Unit 33, Chester, MD 21619
  • 190 Harrier Way Unit 24, Chester, MD 21619
    190 Harrier Way Unit 24, Chester, MD 21619
    190 Harrier Way Unit 24, Chester, MD 21619
    /81

    $650,000

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft

    190 Harrier Way Unit 24, Chester, MD 21619

    Built for low-maintenance living, this beautiful 3-bedroom, 2.5-bath condo offers 2,600 square feet of comfort, space, and resort-style amenities. The open living, dining, and kitchen layout is ideal for everyday living and entertaining.Enjoy peaceful views of three ponds from the beautiful porch, with limited views of the Chester River. The kitchen features 42-inch cabinets, white quartz

    Dee Dee McCracken Coldwell Banker Realty

    190 Harrier Way Unit 24, Chester, MD 21619
  • 54F Queen Caroline Ct, Chester, MD 21619
    54F Queen Caroline Ct, Chester, MD 21619
    54F Queen Caroline Ct, Chester, MD 21619
    /46

    $375,000

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft

    54F Queen Caroline Ct, Chester, MD 21619

    Completely remodeled in 2026 with a new kitchen to include new appliances, quartz counters, and backsplash, 3 new bathrooms, all new flooring throughout, new washer and dryer and freshly painted. Nestled in the serene enclave of Queens Landing, this exquisite remodeled in 2026 Colonial townhouse offers a harmonious blend of luxury and comfort. Spanning 1,440 square feet, the open floor plan

    Lawrence Doyle Long & Foster Real Estate, Inc.

    54F Queen Caroline Ct, Chester, MD 21619
  • 1906 Stevens Dr, Chester, MD 21619
    1906 Stevens Dr, Chester, MD 21619
    1906 Stevens Dr, Chester, MD 21619
    /49

    $464,000

    • 3 Beds
    • 2 Baths
    • 2,016 Sq Ft

    1906 Stevens Dr, Chester, MD 21619

    Spacious and beautifully updated ranch-style home offering over 2,000 square feet of comfortable one-level living. This versatile layout features 3 bedrooms and 2 full baths, including a large bonus room that can easily function as a fourth bedroom, home office, or second living area. A welcoming front porch sets the tone, while the screened back porch provides the perfect space to relax or

    Terri Murray RE/MAX Executive

    1906 Stevens Dr, Chester, MD 21619
  • 126 Claiborne St, Chester, MD 21619
    126 Claiborne St, Chester, MD 21619
    126 Claiborne St, Chester, MD 21619
    /44

    $787,900

    Open Sat 4PM - 6PM
    • 3 Beds
    • 2.5 Baths
    • 2,276 Sq Ft

    126 Claiborne St, Chester, MD 21619

    Welcome to 126 Claiborne Street in the sought-after Gibson's Grant community on Kent Island — a beautifully crafted Covell-built Sawgrass model offering the perfect blend of coastal charm and comfortable with peaceful pond and park views right outside your door This thoughtfully designed home features 3 bedrooms, 2.5 baths, and a desirable main-level primary suite complete with a private en suite

    Tara Trout Samson Properties

    126 Claiborne St, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 3

Maryland Queen Anne's County Chester

Newest Listings for Sale in Chester, MD

Frequently Asked Questions

What is the average home price in Chester, MD?
Homes for sale in Chester, MD have an average home price of $678,128.
How many homes have sold over the last 12 months in Chester, MD?
219 homes have sold in Chester, MD over the last 12 months.
Is Chester, MD a safe city?
In general, the safest neighborhood in Chester, MD with lower crime scores is Kent Narrows.
What are the most popular zip codes in Chester, MD?
The most popular zip codes in Chester, MD include 21619, 21666, 21638, 21658 and 21409.
What are the most popular neighborhoods in Chester, MD?
The most popular neighborhood in Chester, MD with the most homes for sale is Kent Narrows.
How much do you need to make to afford a house in Chester?
The median home price in Chester is $679,900. If you put a 20% down payment of $136,000 and had a 30-year fixed mortgage with an interest rate of 6.53%, your estimated principal and interest payment would be $3,450 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $148K a year to afford the median home price in Chester. Learn how much home you can afford with our Home Affordability Calculator.
How are the schools in Chester, MD?
Chester, MD has highly rated public and private schools. Some of the best schools in Chester based on Niche Grades are Bayside Elementary School, Matapeake Middle School and Kent Island Elementary School. The neighborhood in Chester with the highest rated schools is Kent Narrows. Browse all the schools in Chester, MD to learn more.

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 302 days on the market compared to the national average of 58 days. The median sale price for homes in Chester, MD over the last 12 months is $649,900, up 12% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$649,900
Median Single Family Sale Price
$700,995
Median Townhouse Sale Price
$365,000
Median 2 Bedroom Sale Price
$553,450
Median 1 Bedroom Sale Price
$269,000
Average Price Per Sq Ft
$301
Number of Homes for Sale
86
Last 12 months Home Sales
219
Months of Supply
4.70
Median List Price
$679,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
12%
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