209

Recently Sold Chester, MD Homes

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  • 121 Wheelhouse Way Unit 11, Chester, MD 21619
    121 Wheelhouse Way Unit 11, Chester, MD 21619
    121 Wheelhouse Way Unit 11, Chester, MD 21619
    /10

    $539,900 Sold Sep 08, 2025

    • 2,003 Sq Ft
    • $270/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    121 Wheelhouse Way Unit 11, Chester, MD 21619

    Home office with double doors near entry.Gourmet kitchen with central island for prep & dining.Dining area includes built-in dry bar.Great room features a sleek electric fireplace.Multi-slide glass doors open to rear patio.Owner’s suite with walk-in closet for storage.Spa-inspired owner’s bath with dual sinks.

    K. Hovnanian Homes

    121 Wheelhouse Way Unit 11, Chester, MD 21619
  • 202 Ringneck Ct, Chester, MD 21619
    202 Ringneck Ct, Chester, MD 21619
    202 Ringneck Ct, Chester, MD 21619
    /72

    $335,000 Sold Sep 05, 2025

    • 1,956 Sq Ft
    • $171/SF
    • 94 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1995

    202 Ringneck Ct, Chester, MD 21619

    PRICE IMPROVED.............Dont miss out, still time to enjoy summer near the water!Beautifully Updated End-Unit Townhouse in Sought-After Bayside Community!This spacious 2-bedroom, 2.5-bath end-unit townhome with a 1-car garage offers the perfect blend of comfort, style, and convenience. Step inside to discover a beautifully remodeled kitchen and updated bathrooms that add a

    Sheila Washburn Benson & Mangold, LLC

    202 Ringneck Ct, Chester, MD 21619
  • 1771 Harbor Dr, Chester, MD 21619
    1771 Harbor Dr, Chester, MD 21619
    1771 Harbor Dr, Chester, MD 21619
    /51

    $735,000 Sold Sep 05, 2025

    • 2,564 Sq Ft
    • $287/SF
    • 195 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 1986

    1771 Harbor Dr, Chester, MD 21619

    This beautifully crafted waterfront home boasts five spacious bedrooms and 2.5 baths, offering ample space for comfortable living. The expansive layout includes multiple living areas, ideal for both relaxation and entertainment. The sunroom, with its wall-to-wall sliding doors, provides stunning views of the water, while the family room features a cozy fireplace. A separate formal living room and

    Dee Dee McCracken Coldwell Banker Realty

    1771 Harbor Dr, Chester, MD 21619
  • 211 Switchgrass Way Unit 1512, Chester, MD 21619
    211 Switchgrass Way Unit 1512, Chester, MD 21619
    211 Switchgrass Way Unit 1512, Chester, MD 21619
    /49

    $484,900 Sold Sep 05, 2025

    • 2,000 Sq Ft
    • $242/SF
    • 30 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2024

    211 Switchgrass Way Unit 1512, Chester, MD 21619

    This Magothy home design offers a modern, open floorplan that blends seamlessly with Legacy design elements, creating a space that feels both expansive and inviting. Set to be available for settlement in September 2025, this home features 2 bedrooms and 2.5 baths, perfect for those looking for comfort and style. A standout feature of the Magothy is its dedicated home office, ideal for remote work

    Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1512, Chester, MD 21619
  • 211 Switchgrass Way Unit 1511, Chester, MD 21619
    211 Switchgrass Way Unit 1511, Chester, MD 21619
    211 Switchgrass Way Unit 1511, Chester, MD 21619
    /55

    $500,900 Sold Sep 05, 2025

    • 2,000 Sq Ft
    • $250/SF
    • 12 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2024

    211 Switchgrass Way Unit 1511, Chester, MD 21619

    The Magothy home design is a thoughtfully crafted residence that combines an open floorplan with the timeless elegance of Legacy design. With a projected settlement date in October 2025, this home offers a perfect blend of modern living and classic style. It features two bedrooms, two and a half bathrooms, and a one-car garage, providing a spacious and comfortable living environment.The

    Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1511, Chester, MD 21619
  • 31C Queen Anne Way, Chester, MD 21619
    31C Queen Anne Way, Chester, MD 21619
    31C Queen Anne Way, Chester, MD 21619
    /46

    $322,500 Sold Sep 04, 2025

    • 1,104 Sq Ft
    • $292/SF
    • 26 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1983

    31C Queen Anne Way, Chester, MD 21619

    Welcome to 31-C Queen Anne Way, a beautifully updated two-bedroom, 1.5-bath located in Condo located in the desirable waterfront community of Queens Landing. This well-maintained unit offers 1,104 square feet of thoughtfully designed living space spread across the second and third levels. Enjoy unobstructed views of Lake Amletto and the community water tower, along with partial but striking

    Julia Stevens Realty Navigator

    31C Queen Anne Way, Chester, MD 21619
  • 24 D Queen Elizabeth Ct, Chester, MD 21619
    24 D Queen Elizabeth Ct, Chester, MD 21619
    24 D Queen Elizabeth Ct, Chester, MD 21619
    /86

    $545,000 Sold Sep 04, 2025

    • 1,680 Sq Ft
    • $324/SF
    • 36 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1985

    24 D Queen Elizabeth Ct, Chester, MD 21619

    Welcome to 24D Queen Elizabeth Ct, a beautifully updated 2-bedroom waterfront condo with a spacious loft that easily serves as a third bedroom, office, or bonus space. Nestled in the highly desirable Queens Landing community, this home offers spectacular front and back water views — enjoy both peaceful sunrises and vibrant sunsets every day. Boat slip is negotiable with sale.Inside, the

    The Williams Home Team JPAR Maryland Living

    24 D Queen Elizabeth Ct, Chester, MD 21619
  • 203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    203 Riverside Dr, Chester, MD 21619
    /8

    $185,000 Sold Sep 02, 2025

    • Land
    • 0.21 Acre
    • $880,952 per Acre
    • 319 Days On Market

    203 Riverside Dr, Chester, MD 21619

    Waterfront lot on Crab Alley Creek! Build your dream home and start enjoying the Island Life! Conservation lands are across the creek. Relax by the water and enjoy watching mother nature at her finest. Large sized lot that drains well. Tax Records are incorrect, the lot is 14,733 s.f. (.338 acres), see Survey in Documents. Public sewer hook up is available. Close to local shopping, restaurants,

    Rick Parreco RE/MAX Executive

    203 Riverside Dr, Chester, MD 21619
  • 223 Broadwater Dr, Chester, MD 21619
    223 Broadwater Dr, Chester, MD 21619
    223 Broadwater Dr, Chester, MD 21619
    /56

    $837,000 Sold Aug 30, 2025

    • 2,745 Sq Ft
    • $305/SF
    • 11 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2022

    223 Broadwater Dr, Chester, MD 21619

    ****************Welcome to Your Dream Home at Four Seasons on Kent Island*******************Step into refined elegance and low-maintenance luxury living with this stunning Killarney w/Loft model, the most sought-after floor plan in the exclusive Four Seasons at Kent Island community. This single family home blends style, comfort, and functionality, in one of the Eastern Shore's premier 55+

    Ralph Kennedy RE/MAX Executive

    223 Broadwater Dr, Chester, MD 21619
  • 1773 Harbor Dr, Chester, MD 21619
    1773 Harbor Dr, Chester, MD 21619
    1773 Harbor Dr, Chester, MD 21619
    /44

    $610,000 Sold Aug 29, 2025

    • 2,142 Sq Ft
    • $285/SF
    • 8 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1987

    1773 Harbor Dr, Chester, MD 21619

    Custom built waterfront home in Harbor View! Come on in and make it your own! Excellent views of the water from every room in the house! Kitchen with lots of storage and counter space opens to two-story living room with floor to ceiling windows! Main level bedroom that could be converted into a primary suite! Upstairs primary suite has excellent views of the water, overlooks living area, and has

    Jessica Busch Keller Williams Flagship

    1773 Harbor Dr, Chester, MD 21619
  • 7C Queen Victoria Way, Chester, MD 21619
    7C Queen Victoria Way, Chester, MD 21619
    7C Queen Victoria Way, Chester, MD 21619
    /68

    $237,000 Sold Aug 29, 2025

    • 724 Sq Ft
    • $327/SF
    • 128 Days On Market
    • Studio
    • 1 Bath
    • Built 1983

    7C Queen Victoria Way, Chester, MD 21619

    Price Improvement!! Discover the charm of waterfront living with this unique studio condominium in the sought-after community of Queen’s Landing. Priced attractively, this open-floor-plan oasis offers no ordinary view – gaze out from a generous patio as boats drift by and the sun sets in a spectacular display, arguably one of the best on Kent Island.Perfect as a year-round vacation

    Julia Stevens Realty Navigator

    7C Queen Victoria Way, Chester, MD 21619
  • 509 Warbler Way, Chester, MD 21666
    509 Warbler Way, Chester, MD 21666
    509 Warbler Way, Chester, MD 21666
    /22

    $699,900 Sold Aug 28, 2025

    • 1,993 Sq Ft
    • $351/SF
    • 2 Beds
    • 2 Baths
    • Built 2025

    509 Warbler Way, Chester, MD 21666

    Polished kitchen featuring Brellin White cabinets & Statuary Classique quartz countertops.Spacious great room with high vaulted ceiling & cozy fireplace.Organized home office for studying or reading.Lavish primary suite & bath featuring dual vanities & walk-in closet.Versatile screened patio for relaxing with friends.Functional 2-car garage for vehicles & tools.

    K. Hovnanian Homes

    509 Warbler Way, Chester, MD 21666
  • 35 F Queen Anne Way, Chester, MD 21619
    35 F Queen Anne Way, Chester, MD 21619
    35 F Queen Anne Way, Chester, MD 21619
    /60

    $355,000 Sold Aug 28, 2025

    • 1,440 Sq Ft
    • $247/SF
    • 52 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1994

    35 F Queen Anne Way, Chester, MD 21619

    Welcome to 35F Queen Anne Way in Queens Landing! This lakefront updated home offers 2 bedrooms and 2 full bathrooms. Updates include a spacious kitchen and both bathrooms. Wake up to lakefront views from the spacious primary bedroom and enjoy a cup of coffee or a glass of wine on the back patio or three season room while gazing over the lake. A stones throw away is the scenic Chester River

    Lawrence Doyle Long & Foster Real Estate, Inc.

    35 F Queen Anne Way, Chester, MD 21619
  • 103 John Gibson Dr, Chester, MD 21619
    103 John Gibson Dr, Chester, MD 21619
    103 John Gibson Dr, Chester, MD 21619
    /62

    $789,000 Sold Aug 27, 2025

    • 2,602 Sq Ft
    • $303/SF
    • 120 Days On Market
    • 4 Beds
    • 3 Baths
    • Built 2012

    103 John Gibson Dr, Chester, MD 21619

    PRICE REDUCED!!!! Freshly painted and ready to go! Take a tour of this beautiful home in the sought after community of Gibsons Grant on Kent Island. This home rests just minutes from the Chesapeake Bay Bridge, Annapolis, Baltimore or DC. Everything in this home has been meticulously cared for. You will find ceramic tile flooring as you enter transitioning to beautiful plank flooring

    Edward Beres RE/MAX Executive

    103 John Gibson Dr, Chester, MD 21619
  • 327 Kingfisher Ln, Chester, MD 21619
    327 Kingfisher Ln, Chester, MD 21619
    327 Kingfisher Ln, Chester, MD 21619
    /38

    $949,900 Sold Aug 26, 2025

    • 3,225 Sq Ft
    • $295/SF
    • 5 Beds
    • 4.5 Baths
    • Built 2025

    327 Kingfisher Ln, Chester, MD 21619

    Charming kitchen featuring Winstead Birch Quill cabinets.Open concept living spaces with vaulted ceiling & cozy fireplace.Relaxing primary suite & bath with generous walk-in closet.Productive home office for working remotely.Secluded Extra Suite, ideal for overnight guests.Versatile screened patio for spending time with friends.Attached 3-car tandem garage for vehicles & storage.

    K. Hovnanian Homes

    327 Kingfisher Ln, Chester, MD 21619
  • 602 Dominion Rd, Chester, MD 21619
    602 Dominion Rd, Chester, MD 21619
    602 Dominion Rd, Chester, MD 21619
    /34

    $226,000 Sold Aug 25, 2025

    • 1,800 Sq Ft
    • $126/SF
    • 49 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 1900

    602 Dominion Rd, Chester, MD 21619

    BUYERS FINANCING FELL THROUGH. THEIR LOSS YOUR GAIN!! **INVESTOR ALERT!!** Multi-unit home. First floor features a mud room, full kitchen with laundry connections, living space, full bathroom, and room for a bedroom- Could be used as an efficiency apartment. Second floor, with separate entrance, features a kitchen, living area, full bathroom, bedroom and finished attic/additional living space.

    Janice O'Donnell Chaney Homes, LLC

    602 Dominion Rd, Chester, MD 21619
  • 2008 Palm Dr, Chester, MD 21619
    2008 Palm Dr, Chester, MD 21619
    2008 Palm Dr, Chester, MD 21619
    /51

    $500,000 Sold Aug 22, 2025

    • 2,283 Sq Ft
    • $219/SF
    • 64 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1997

    2008 Palm Dr, Chester, MD 21619

    New Price Improvement! Cape Cod with spacious wrap around porch! Upon entering, you will be greeted with hardwood floors throughout most of the main level. The focal point once inside is the beautiful open family room with a wood burning fireplace with stacked stone soaring to the vaulted ceiling and two ceiling fans when cooling off in the warmer months! The gourmet kitchen opens up into the

    Marilyn Hendley EXP Realty, LLC

    2008 Palm Dr, Chester, MD 21619
  • 241 Warbler Way, Chester, MD 21619
    241 Warbler Way, Chester, MD 21619
    241 Warbler Way, Chester, MD 21619
    /54

    $629,900 Sold Aug 21, 2025

    • 1,993 Sq Ft
    • $316/SF
    • 4 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2024

    241 Warbler Way, Chester, MD 21619

    Jenkins Home Design - Projected Settlement Date: June 2025Welcome to the Jenkins, a beautifully designed home located on Lot 374, offering both comfort and style in a thoughtfully planned layout. This home features 2 bedrooms, 2 full bathrooms, and a 2-car garage, making it perfect for easy living with modern flair.Highlights Include:Dedicated Home Office – ideal for remote

    Mary Anne Kowalewski KOVO Realty

    241 Warbler Way, Chester, MD 21619
  • 201 Switchgrass Way Unit 43, Chester, MD 21619
    201 Switchgrass Way Unit 43, Chester, MD 21619
    201 Switchgrass Way Unit 43, Chester, MD 21619
    /25

    $784,900 Sold Aug 20, 2025

    • 1,900 Sq Ft
    • $413/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    201 Switchgrass Way Unit 43, Chester, MD 21619

    Private home office with double doors for a quiet workspace.Central island anchors the gourmet kitchen with wall oven.Great room with a warm electric fireplace & balcony access.Dining area includes a dry bar, perfect for hosting.Owner’s suite offers a retreat with private balcony entry.Spa-like owner’s bath with dual vanities & modern

    K. Hovnanian Homes

    201 Switchgrass Way Unit 43, Chester, MD 21619
  • 201 Switchgrass Way Unit 42, Chester, MD 21619
    201 Switchgrass Way Unit 42, Chester, MD 21619
    201 Switchgrass Way Unit 42, Chester, MD 21619
    /25

    $784,900 Sold Aug 20, 2025

    • 1,900 Sq Ft
    • $413/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    201 Switchgrass Way Unit 42, Chester, MD 21619

    Home office with elegant double-door entry.Gourmet kitchen with wall oven & oversized island.Dining area includes a built-in dry bar for entertaining.Great room with an electric fireplace & natural light.Access to the balcony from both the great room & owner’s suite.Dual vanities in the owner’s spa bath for a luxe feel.Smartly designed floorplan

    K. Hovnanian Homes

    201 Switchgrass Way Unit 42, Chester, MD 21619
  • 121 Wheelhouse Way Unit 21, Chester, MD 21619
    121 Wheelhouse Way Unit 21, Chester, MD 21619
    121 Wheelhouse Way Unit 21, Chester, MD 21619
    /18

    $719,900 Sold Aug 20, 2025

    • 2,602 Sq Ft
    • $277/SF
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    121 Wheelhouse Way Unit 21, Chester, MD 21619

    Beautiful gourmet kitchen overlooks open concept living spaces.Spacious great room with warm fireplace.Sun-lit dining area with drybar, perfect for hosting dinner parties.Lavish owner's suite & bath featuring dual walk-in closets & sitting room.Convenient laundry room located near secondary bedrooms.Lovely balcony for outdoor relaxation.

    K. Hovnanian Homes

    121 Wheelhouse Way Unit 21, Chester, MD 21619
  • 132 Wheelhouse Way Unit 21, Chester, MD 21619
    132 Wheelhouse Way Unit 21, Chester, MD 21619
    132 Wheelhouse Way Unit 21, Chester, MD 21619
    /87

    $989,000 Sold Aug 18, 2025

    • 2,602 Sq Ft
    • $380/SF
    • 27 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2023

    132 Wheelhouse Way Unit 21, Chester, MD 21619

    Don't wait for New Construction! This nearly NEW luxury condo is available NOW! Welcome to 132 Wheelhouse Way Unit 21, an extraordinary residence where elegance meets ease. This impeccably designed 3-bedroom, 2.5-bath corner unit in the coveted Four Seasons at Kent Island offers over 2,600 square feet of refined single-level living with unparalleled panoramic views of the Chester River. From the

    Kathleen Higginbotham Keller Williams Flagship

    132 Wheelhouse Way Unit 21, Chester, MD 21619
  • 360 Macum Creek Dr, Chester, MD 21619
    360 Macum Creek Dr, Chester, MD 21619
    360 Macum Creek Dr, Chester, MD 21619
    /71

    $915,000 Sold Aug 15, 2025

    • 3,225 Sq Ft
    • $284/SF
    • 3 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2012

    360 Macum Creek Dr, Chester, MD 21619

    Welcome to 360 Macum Creek Drive – where charm, space, and style come together in the sought-after waterfront community of Gibson’s Grant.Situated on a prime corner lot, this beautifully maintained home offers over 3,200 square feet of versatile living space with 3 bedrooms, 2.5 bathrooms, and a third-floor recreation room that can easily function as a fourth bedroom, home office, or

    Tara Trout Keller Williams Flagship

    360 Macum Creek Dr, Chester, MD 21619
  • 1809 Stevens Dr, Chester, MD 21619
    1809 Stevens Dr, Chester, MD 21619
    1809 Stevens Dr, Chester, MD 21619
    /33

    $445,000 Sold Aug 14, 2025

    • 1,896 Sq Ft
    • $235/SF
    • 41 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 1975

    1809 Stevens Dr, Chester, MD 21619

    Best deal on Kent Island! Beautiful 4 Bedroom 2 1/2 bath Cape on over 1/2 acre in peaceful Harbor View. Airy and spacious, this terrific home boasts 2 Bedrooms plus Full bath on the Main level with all new hardwood flooring and separate light -filled and cozy living and dining spaces. The gorgeous just updated kitchen features fabulous quartz countertops, all modern stainless steel

    Greg Koch Taylor Properties

    1809 Stevens Dr, Chester, MD 21619
  • 194 Sailcloth Way, Chester, MD 21619
    194 Sailcloth Way, Chester, MD 21619
    194 Sailcloth Way, Chester, MD 21619
    /61

    $790,000 Sold Aug 13, 2025

    • 2,453 Sq Ft
    • $322/SF
    • 72 Days On Market
    • 3 Beds
    • 3 Baths
    • Built 2021

    194 Sailcloth Way, Chester, MD 21619

    Welcome to your dream home situated on a coveted premium lot that backs to the woods giving you endless views of wildlife. The first-floor living is ideal for all homeowners and offers you a large primary bedroom, an office/2nd bedroom and a completely open concept on the main level. The kitchen boasts custom cabinets, stainless steel appliances, double oven, gas range with exhaust hood and

    Ross Hunsberger Coldwell Banker Realty

    194 Sailcloth Way, Chester, MD 21619
  • 211 Golden Eye Ct, Chester, MD 21619
    211 Golden Eye Ct, Chester, MD 21619
    211 Golden Eye Ct, Chester, MD 21619
    /34

    $285,000 Sold Aug 08, 2025

    • 1,073 Sq Ft
    • $266/SF
    • 10 Days On Market
    • 2 Beds
    • 2 Baths
    • Built 2000

    211 Golden Eye Ct, Chester, MD 21619

    Discover this impeccably cared-for 2-bedroom, 2-bathroom condo, offering the ultimate in low-maintenance living within one of Kent Island’s most desirable neighborhoods. This second floor unit boasts an open-concept living and dining area that creates a warm, inviting space perfect for both relaxing and entertaining. Enjoy peace and tranquility on your personal balcony. The Bayside community

    Brendan Noone Coldwell Banker Realty

    211 Golden Eye Ct, Chester, MD 21619
  • 133 Henry Stoupe Way, Chester, MD 21619
    133 Henry Stoupe Way, Chester, MD 21619
    133 Henry Stoupe Way, Chester, MD 21619
    /72

    $960,000 Sold Aug 08, 2025

    • 3,541 Sq Ft
    • $271/SF
    • 4 Days On Market
    • 6 Beds
    • 4.5 Baths
    • Built 2011

    133 Henry Stoupe Way, Chester, MD 21619

    Welcome to your dream home in the sought-after waterfront community of Gibson’s Grant! Situated on one of the largest corner lots in the neighborhood, this spacious 6-bedroom, 4.5-bathroom home offers over 3,500 square feet of beautifully designed living space — perfect for comfortable everyday living and effortless entertaining.Step into your own backyard oasis featuring a 520 sq ft

    Tara Trout Keller Williams Flagship

    133 Henry Stoupe Way, Chester, MD 21619
  • 203 Anchor Ln, Chester, MD 21619
    203 Anchor Ln, Chester, MD 21619
    203 Anchor Ln, Chester, MD 21619
    /27

    $499,000 Sold Aug 06, 2025

    • 1,890 Sq Ft
    • $264/SF
    • 40 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 1977

    203 Anchor Ln, Chester, MD 21619

    HOT OFF THE PRESS! Seller is offering to pay down mortgage rate by 1 point for any accepted offer by June 20th! Plus the listing agent will provide a home warranty! WE INVITE YOU TO TAKE A 2nd LOOK!! Staged and re-freshed you'll wonder why you didn't scoop this one up earlier! This adorable rancher has the traditional 3 bedrooms and 2 baths and so much more including a large dining area,

    Tricia Wilson Wilson Realty & Staging LLC

    203 Anchor Ln, Chester, MD 21619
  • 2707 Cox Neck Rd, Chester, MD 21619
    2707 Cox Neck Rd, Chester, MD 21619
    2707 Cox Neck Rd, Chester, MD 21619
    /47

    $435,000 Sold Aug 04, 2025

    • 1,568 Sq Ft
    • $277/SF
    • 34 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 1995

    2707 Cox Neck Rd, Chester, MD 21619

    Welcome to Harborview, a long established community on Maryland's eastern shore, home of some of the best seafood on the eastern seaboard! Come see everything that living on "The Shore" has to offer. Fantastic dining on the Kent Narrows, shopping at the outlets, the new pickleball courts in nearby Stevensville and Grasonville, the dog park and of course the new skate park! The Cross Island trail

    Samantha Hernandez Douglas Realty, LLC

    2707 Cox Neck Rd, Chester, MD 21619
  • 2614 Ellicott Dr, Chester, MD 21619
    2614 Ellicott Dr, Chester, MD 21619
    2614 Ellicott Dr, Chester, MD 21619
    /43

    $495,000 Sold Jul 31, 2025

    • 1,400 Sq Ft
    • $354/SF
    • 2 Days On Market
    • 3 Beds
    • 2 Baths
    • Built 2023

    2614 Ellicott Dr, Chester, MD 21619

    Like-New Construction | Turn-Key Living | Prime Chester Location. Welcome to 2614 Ellicott Drive, a stunning 2023-built home that blends modern design with everyday comfort — all nestled in the heart of Kent Island. Move-in ready and in absolute mint condition, this beautifully appointed property offers the perfect blend of style, space, and location. Step inside to discover rich, wide-plank

    Wendy Oliver Coldwell Banker Realty

    2614 Ellicott Dr, Chester, MD 21619
  • 412 Hanna Ct, Chester, MD 21619
    412 Hanna Ct, Chester, MD 21619
    412 Hanna Ct, Chester, MD 21619
    /51

    $485,000 Sold Jul 31, 2025

    • 1,840 Sq Ft
    • $264/SF
    • 15 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2001

    412 Hanna Ct, Chester, MD 21619

    Welcome to 412 Hanna Court, Chester, MD – DID YOU KNOW THIS HOME HAS AN 2.75% ASSUMABLE VA MORTGAGE of $294K!!! Nestled at the end of a quiet cul-de-sac in the highly sought-after Claybourne Woods community, this beautifully maintained 4-bedroom, 2.5-bath home blends modern upgrades with everyday comfort in an ideal Eastern Shore location. Enjoy a quick 30-minute commute to Downtown

    Sarah Miller Hubble Bisbee Christie's International Real Estate

    412 Hanna Ct, Chester, MD 21619
  • 15G Queen Anne Way, Chester, MD 21619
    15G Queen Anne Way, Chester, MD 21619
    15G Queen Anne Way, Chester, MD 21619
    /27

    $340,000 Sold Jul 31, 2025

    • 1,104 Sq Ft
    • $308/SF
    • 34 Days On Market
    • 2 Beds
    • 1.5 Baths
    • Built 1983

    15G Queen Anne Way, Chester, MD 21619

    Welcome to Queens Landing - Easy Living in this 2 bed 1.5 bath Waterfront Townhome ! Home features private balcony and patio overlooking the Chester River. Open floor plan with dining/living combo and main level powder room. So many amenities including Club House, In-ground heated pool, fitness center, and tennis and pickleball courts. Enjoy marina views and biking and walking trails. You'll

    Mackenzie Hoffer CENTURY 21 New Millennium

    15G Queen Anne Way, Chester, MD 21619
  • 218 Switchgrass Way Unit 1732, Chester, MD 21619
    218 Switchgrass Way Unit 1732, Chester, MD 21619
    218 Switchgrass Way Unit 1732, Chester, MD 21619
    /55

    $829,900 Sold Jul 30, 2025

    • 1,900 Sq Ft
    • $437/SF
    • 17 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    218 Switchgrass Way Unit 1732, Chester, MD 21619

    Experience the perfect blend of form and function in the Chester, a thoughtfully designed 2-bedroom, 2.5-bath home with a 1-car garage and smart upgrades throughout. Whether you're looking for a comfortable everyday retreat or a low-maintenance second home, this property offers it all.Enjoy the warmth of an electric fireplace, the convenience of a built-in dry bar, and the flexibility of

    Mary Anne Kowalewski KOVO Realty

    218 Switchgrass Way Unit 1732, Chester, MD 21619
  • 34B Queen Anne Way Unit B, Chester, MD 21619
    34B Queen Anne Way Unit B, Chester, MD 21619
    34B Queen Anne Way Unit B, Chester, MD 21619
    /24

    $320,000 Sold Jul 30, 2025

    • 800 Sq Ft
    • $400/SF
    • 79 Days On Market
    • 1 Bed
    • 1 Bath
    • Built 1983

    34B Queen Anne Way Unit B, Chester, MD 21619

    EXCELLENT PRICE reduction!! Waterfront...waterfront! Super one bedroom/bathroom condo. Largest of the one-bedroom units. Absolutely gorgeous view across the Chester River from the living area . Private patio on waterside. Luxury vinyl wood-look flooring throughout! The condo is quite roomy and easy to take care of! No outstanding assessments on it! Low condo fee, as well! Community has wonderful

    Mary Stevens Long & Foster Real Estate, Inc.

    34B Queen Anne Way Unit B, Chester, MD 21619
  • 121 Wheelhouse Way Unit 12, Chester, MD 21619
    121 Wheelhouse Way Unit 12, Chester, MD 21619
    121 Wheelhouse Way Unit 12, Chester, MD 21619
    /10

    $541,900 Sold Jul 28, 2025

    • 2,003 Sq Ft
    • $271/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    121 Wheelhouse Way Unit 12, Chester, MD 21619

    Efficient gourmet kitchen featuring vast center island & designer cabinets.Cozy electric fireplace adds character & warmth to great room.Refined dining area featuring convenient dry bar.Lavish owner's suite & spa bath with walk-in closet.Productive home office with double doors.Inviting covered patio for relaxing outdoors.

    K. Hovnanian Homes

    121 Wheelhouse Way Unit 12, Chester, MD 21619
  • 320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    /63

    $775,000 Sold Jul 28, 2025

    • 2,331 Sq Ft
    • $332/SF
    • 1 Day On Market
    • 3 Beds
    • 2 Baths
    • Built 2021

    320 Bayberry Dr, Chester, MD 21619

    Have it all at 320 Bayberry Drive in the award-winning Four Seasons at Kent Island! This stunning 2021-built home sits on a premium lot adjacent to open space, offering exceptional privacy and abundant natural light. Beautifully upgraded throughout, the home features 10-foot ceilings, a gourmet kitchen with upgraded cabinetry and tile, designer lighting, luxury flooring, and a cozy gas fireplace.

    Melanie Wood Berkshire Hathaway HomeServices PenFed Realty

    320 Bayberry Dr, Chester, MD 21619
  • 1614 Postal Rd, Chester, MD 21619
    1614 Postal Rd, Chester, MD 21619
    1614 Postal Rd, Chester, MD 21619
    /43

    $595,000 Sold Jul 28, 2025

    • 2,656 Sq Ft
    • $224/SF
    • 59 Days On Market
    • 5 Beds
    • 2.5 Baths
    • Built 2003

    1614 Postal Rd, Chester, MD 21619

    Welcome to this Lovingly and Well-Maintained Colonial Style Home! Looking for a Home based business? This one is it, as it offers a rare opportunity with incredible versatility with Town Center Zoning, making it perfect for a private residence, bed & breakfast, Airbnb, or the opportunity to live where you work. Nestled on a Large Lot backing to Woods offers both Privacy and Charm! Spanning

    Pamela Ackermann-Doll RE/MAX Executive

    1614 Postal Rd, Chester, MD 21619
  • 211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    211 Switchgrass Way Unit 31, Chester, MD 21619
    /19

    $739,900 Sold Jul 24, 2025

    • 2,602 Sq Ft
    • $284/SF
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    211 Switchgrass Way Unit 31, Chester, MD 21619

    Striking gourmet kitchen with designer cabinets & chef-worthy island.Elegant dining area featuring fancy dry bar.Refined great room featuring stunning fireplace.Serene owner's suite with maginificnet sitting room & walk-in closets.Owner's spa bath with dual sinks and lavish shower.Wonderful balcony for relaxing outdoors.

    K. Hovnanian Homes

    211 Switchgrass Way Unit 31, Chester, MD 21619
  • 107 Lee Rd, Chester, MD 21619
    107 Lee Rd, Chester, MD 21619
    107 Lee Rd, Chester, MD 21619
    /11

    $259,000 Sold Jul 24, 2025

    • 960 Sq Ft
    • $270/SF
    • 160 Days On Market
    • 3 Beds
    • 1 Bath
    • Built 1984

    107 Lee Rd, Chester, MD 21619

    OPEN HOUSE, Saturday, May 24, from 11am to 1pm...Best 3 Br buy on Kent Island! Recent upgrades! Hurry!

    Darlene Winegardner RE/MAX Executive

    107 Lee Rd, Chester, MD 21619
  • 416 Warbler Way, Chester, MD 21619
    416 Warbler Way, Chester, MD 21619
    416 Warbler Way, Chester, MD 21619
    /17

    $669,900 Sold Jul 23, 2025

    • 1,993 Sq Ft
    • $336/SF
    • 2 Beds
    • 2 Baths
    • Built 2025

    416 Warbler Way, Chester, MD 21619

    Well-equipped kitchen featuring Brellin White cabinets & Statuary Classique quartz countertops.Spacious great room featuring vaulted ceiling.Functional dining area for mealtime enjoyment.Productive home office for working remotely.Lavish primary suite & bath with dual vanities & walk-in closet.Versatile screened patio for relaxation.

    K. Hovnanian Homes

    416 Warbler Way, Chester, MD 21619

Showing Results 1 - 40, Page 1 of 6

Maryland Queen Annes County Chester

Recently Sold Real Estate & Homes 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 $607,310.
What is the average time to sell a house in Chester, MD?
The houses for sale in Chester, MD spend an average of 44 days on the market.
What is the number of active homes for sale in Chester, MD?
There are 59 active homes for sale in Chester, MD.
How many homes have sold over the last 12 months in Chester, MD?
173 homes have sold in Chester, MD over the last 12 months.

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 44 days on the market compared to the national average of 52 days. The median sale price for homes in Chester, MD over the last 12 months is $595,000, up 3% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$595,000
Median Single Family Sale Price
$644,450
Median Townhouse Sale Price
$425,000
Median 2 Bedroom Sale Price
$524,900
Median 1 Bedroom Sale Price
$306,500
Average Price Per Sq Ft
$296
Number of Homes for Sale
59
Last 12 months Home Sales
173
Months of Supply
4.10
Median List Price
$602,400
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
3%
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