5,119

Chester, MD Homes

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  • 47 D Queen Anne Way, Chester, MD 21619
    47 D Queen Anne Way, Chester, MD 21619
    47 D Queen Anne Way, Chester, MD 21619
    /45

    $595,500 Open Sun 12PM - 3PM

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

    47 D Queen Anne Way, Chester, MD 21619

    OPEN HOUSE Sunday Sept 21, 12-3pm. Enjoy resort style living every day in the gorgeous waterfront condo. 42' boat slip w/ water/electric & 25K lb magnum lift conveys - WOW!! Watch the sun & moon rise as you sip your favorite beverage or entertain as everyone will want to come visit you now. This sought after townhome/condo has extensive view of the Chester River & Eastern Neck Island. The owner

    Agent Photo

    Brenda Fornos

    Taylor Properties

    (410) 623-7650

    47 D Queen Anne Way, Chester, MD 21619
  • 137 Warbler Way, Chester, MD 21619
    137 Warbler Way, Chester, MD 21619
    137 Warbler Way, Chester, MD 21619
    /81

    $4,300 per month

    • 2 Beds
    • 2 Baths
    • 2,147 Sq Ft
    • House for Rent

    137 Warbler Way, Chester, MD 21619

    Ready to "try-on" coveted 'Four Seasons'? Treat yourself to this STUNNING beauty- Boasting soaring ceilings, flooded with natural light, spacious, open-floor plan nearly 2200 SF, with generously-sized primary suite & spa-like bath with walk-in-closet, double sinks & walk-in-shower. 2nd bedroom & bath across home offers privacy for guests. Custom barn doors open to bonus space- easily used for 3rd

    Jennifer Chaney Chaney Homes, LLC

    137 Warbler Way, Chester, MD 21619
  • 112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    112 Harbour Sound Dr, Chester, MD 21619
    /40

    $540,656 Sold Sep 19, 2025

    • 2,131 Sq Ft
    • $254/SF
    • 86 Days On Market
    • 2 Beds
    • 3.5 Baths
    • Built 1989

    112 Harbour Sound Dr, Chester, MD 21619

    Resort Living at it's best!! Available furnished or unfurnished. Enjoy stunning, unobstructed water views in the highly sought after community of Bayside! Many recent upgrades and improvements to this home include renovated bathrooms (2024) , New garage door, with fresh sealing floor paint (2023) New Kitchen cabinets (2022), New Double Oven (2022) , New Quartz Countertops (2022) New flooring

    Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619
    • 136 Evelyne St, Chester, MD 21619
      136 Evelyne St, Chester, MD 21619
      136 Evelyne St, Chester, MD 21619
      /81

      Est $851,790 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,771 Sq Ft

      136 Evelyne St, Chester, MD 21619

      136 Evelyne St, Chester, MD 21619
  • 204 Skipper Ln, Chester, MD 21619
    204 Skipper Ln, Chester, MD 21619
    204 Skipper Ln, Chester, MD 21619
    /106

    $624,900 Under Contract

    • 6 Beds
    • 3 Baths
    • 3,760 Sq Ft

    204 Skipper Ln, Chester, MD 21619

    Welcome home to spacious comfort and thoughtful design in this inviting six-bedroom, three-bath residence nestled on a quiet lane in Chester. With over 3,700 square feet of interior living space, there’s room here for everyone—and maybe even that home office or gym you’ve been dreaming about.Step inside to find an updated kitchen ready for your culinary adventures, featuring modern

    Agent Photo

    Andy Schweigman

    Douglas Realty, LLC

    (410) 324-6571

    204 Skipper Ln, Chester, MD 21619
  • 1606 Howard Rd, Chester, MD 21619
    1606 Howard Rd, Chester, MD 21619
    1606 Howard Rd, Chester, MD 21619
    /54

    $5,000 per month

    • 3 Beds
    • 2 Baths
    • 1,755 Sq Ft
    • House for Rent

    1606 Howard Rd, Chester, MD 21619

    Welcome to Crab Alley Bay, Chester, MDThis cherished waterfront home offers one of the most captivating settings on the Eastern Shore—perched on a point with sweeping 270-degree panoramic views of Crab Alley Bay. Resting on approximately three-quarters of an acre, the property is as peaceful and restorative as it is beautiful, providing a rare opportunity to enjoy true waterfront

    Lisa Barton Coldwell Banker Realty

    1606 Howard Rd, Chester, MD 21619
  • 211 Switchgrass Way Unit 1523, Chester, MD 21619
    211 Switchgrass Way Unit 1523, Chester, MD 21619
    211 Switchgrass Way Unit 1523, Chester, MD 21619
    /88

    $534,900 Sold Sep 19, 2025

    • 1,900 Sq Ft
    • $282/SF
    • 16 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    211 Switchgrass Way Unit 1523, Chester, MD 21619

    The Chester home design offers a spacious and inviting living experience, combining an open floorplan with timeless Legacy design elements. With a projected settlement date in September 2025, this home features two bedrooms, two and a half bathrooms, and a one-car garage, providing a comfortable layout perfect for families or those who love extra space.Key features of the Chester include

    Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1523, Chester, MD 21619
    • 326 Thomas White Blvd, Chester, MD 21619
      326 Thomas White Blvd, Chester, MD 21619
      326 Thomas White Blvd, Chester, MD 21619
      /44

      Est $882,689 Not Listed For Sale

      • 4 Beds
      • 3.5 Baths
      • 3,225 Sq Ft

      326 Thomas White Blvd, Chester, MD 21619

      326 Thomas White Blvd, Chester, MD 21619
  • 131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
    /27

    $848,900 New Construction

    • 3 Beds
    • 3.5 Baths
    • 2,930 Sq Ft

    Franklin Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Formal dining room off foyer for entertaining guests. Stylish kitchen with plenty of cabinet space and large island. Open and airy great room with slider to covered patio. Luxurious primary suite with triple windows. Private primary bath with optional freestanding tub. Convenient 2-car garage with storage space.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • 121 Wheelhouse Way Unit 32, Chester, MD 21619
    121 Wheelhouse Way Unit 32, Chester, MD 21619
    121 Wheelhouse Way Unit 32, Chester, MD 21619
    /26

    $679,900 Sold Sep 18, 2025

    • 1,900 Sq Ft
    • $358/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    121 Wheelhouse Way Unit 32, Chester, MD 21619

    Gourmet kitchen with central island for prep & dining.Home office with double doors adds privacy & style.Dining area enhanced by a convenient dry bar.Great room centered around an electric fireplace.Balcony extends living space off the great room.Owner’s suite with private balcony access for relaxation.Spa-like owner’s bath with dual sinks & sleek

    K. Hovnanian Homes

    121 Wheelhouse Way Unit 32, Chester, MD 21619
    • 237 Evelyne St, Chester, MD 21619
      237 Evelyne St, Chester, MD 21619
      237 Evelyne St, Chester, MD 21619
      /59

      Est $881,501 Not Listed For Sale

      • 4 Beds
      • 2.5 Baths
      • 2,840 Sq Ft

      237 Evelyne St, Chester, MD 21619

      237 Evelyne St, Chester, MD 21619
  • 131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    131 Flycatcher Way Unit 36466218, Chester, MD 21619
    /24

    $663,900 New Construction

    • 2 Beds
    • 2 Baths
    • 1,993 Sq Ft

    Jenkins II Plan at K. Hovnanian’s® Four Seasons at Kent Island - River Series, Chester, MD 21619

    Private home office for working from home. Stylish kitchen with large center island and spacious pantry. Spacious great room with slider to covered patio. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with split vanities. Convenient HovHall off garage for keeping home tidy.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36466218, Chester, MD 21619
  • 629 Warbler Way, Chester, MD 21619
    629 Warbler Way, Chester, MD 21619
    629 Warbler Way, Chester, MD 21619
    /11

    $709,900 Sold Sep 18, 2025

    • 2,791 Sq Ft
    • $254/SF
    • 4 Beds
    • 3 Baths
    • Built 2025

    629 Warbler Way, Chester, MD 21619

    Open kitchen, dining area, and great room. Kitchen with Statuary Classique quartz central island. Great room with fireplace for cozy gatherings. Screened patio off great room extends living space. Primary suite with elegant ceiling treatment. Primary bath with dual freestanding vanities. Private home office tucked away from main living areas.

    K. Hovnanian Homes

    629 Warbler Way, Chester, MD 21619
    • 334 Thomas White Blvd, Chester, MD 21619
      334 Thomas White Blvd, Chester, MD 21619
      334 Thomas White Blvd, Chester, MD 21619
      /69

      Est $789,775 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,400 Sq Ft

      334 Thomas White Blvd, Chester, MD 21619

      334 Thomas White Blvd, Chester, MD 21619
  • 131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    131 Flycatcher Way Unit 36469043, Chester, MD 21619
    /26

    $811,900 New Construction

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

    Kerr Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite perfect for overnight guests. Private home office off foyer for working from home. Spacious great room with slider to covered patio. Stylish kitchen with island and large pantry. Luxurious primary suite with triple windows. Relaxing primary bath with split vanities and walk-in closet. Convenient 3-car tandem garage for additional storage space.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36469043, Chester, MD 21619
  • 208 Ringneck Ct, Chester, MD 21619
    208 Ringneck Ct, Chester, MD 21619
    208 Ringneck Ct, Chester, MD 21619
    /66

    $330,000 Sold Sep 16, 2025

    • 1,747 Sq Ft
    • $189/SF
    • 98 Days On Market
    • 2 Beds
    • 2.5 Baths
    • Built 1995

    208 Ringneck Ct, Chester, MD 21619

    208 Ringneck Court is a great home for the smart buyer! The 2 bedroom, 2 1/2 bathroom GARAGE town-home, located in the Bayside community on the Chester River, underwent a MAJOR RENOVATION within the past 3 years. As you enter the south-facing home, you'll notice that the floor plan is a bit different than others...the kitchen has been reconfigured to create an open concept design which

    Phyllis Endrich Long & Foster Real Estate, Inc.

    208 Ringneck Ct, Chester, MD 21619
    • 163 Claiborne St, Chester, MD 21619
      163 Claiborne St, Chester, MD 21619
      163 Claiborne St, Chester, MD 21619
      /46

      Est $661,029 Not Listed For Sale

      • 2 Beds
      • 2.5 Baths
      • 1,824 Sq Ft

      163 Claiborne St, Chester, MD 21619

      163 Claiborne St, Chester, MD 21619
  • 131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
    /40

    $840,900 New Construction

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft

    Tuscaloosa Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Extra Suite with full bath for overnight guests. Private home office off foyer for working from home. Spacious great room with adjacent dining area. Beautiful kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 211 Switchgrass Way Unit 1534, Chester, MD 21619
    211 Switchgrass Way Unit 1534, Chester, MD 21619
    211 Switchgrass Way Unit 1534, Chester, MD 21619
    /88

    $705,250 Sold Sep 16, 2025

    • 2,602 Sq Ft
    • $271/SF
    • 56 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2024

    211 Switchgrass Way Unit 1534, Chester, MD 21619

    The Severn home design offers a spacious and inviting living experience, combining an open floorplan with timeless Legacy design elements. With a projected settlement date in June 2025, this home features three bedrooms, two and a half bathrooms, and a one-car garage, providing a comfortable layout perfect for families or those who love extra space.Key features of the Severn include a

    Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1534, Chester, MD 21619
    • 121 Henry Stoupe Way, Chester, MD 21619
      121 Henry Stoupe Way, Chester, MD 21619
      121 Henry Stoupe Way, Chester, MD 21619
      /38

      Est $693,677 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,320 Sq Ft

      121 Henry Stoupe Way, Chester, MD 21619

      121 Henry Stoupe Way, Chester, MD 21619
  • 131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    131 Flycatcher Way Unit 36493007, Chester, MD 21619
    /12

    $474,990 New Construction

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

    Magothy Plan at K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos, Chester, MD 21619

    Open airy floorplan on the first floor with private patio. Large gourmet kitchen and dining area, great for entertaining. Wonderful home office for your telecommuting needs. Sumptuous owner’s suite with spa bath . Fantastic great room with large windows for your viewing pleasure. Large secondary bedroom with opt. door to access patio. Pricing is inclusive of an average location premium.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36493007, Chester, MD 21619
  • 121 John Gibson Dr, Chester, MD 21619
    121 John Gibson Dr, Chester, MD 21619
    121 John Gibson Dr, Chester, MD 21619
    /50

    $812,500 Sold Sep 15, 2025

    • 2,760 Sq Ft
    • $294/SF
    • 7 Days On Market
    • 4 Beds
    • 2.5 Baths
    • Built 2010

    121 John Gibson Dr, Chester, MD 21619

    Welcome home to 121 John Gibson Drive in the waterfront community of Gibson's Grant on Kent Island. This beautifully maintained 4-bedroom, 2.5-bath home offers the perfect blend of charm, functionality, and comfort. Step inside to discover a bright and open floor plan featuring a cozy gas fireplace, ideal for relaxing evenings or entertaining guests. The heart of the home is the gorgeous offering

    Tara Trout Keller Williams Flagship

    121 John Gibson Dr, Chester, MD 21619
    • 215 John Gibson Dr, Chester, MD 21619
      215 John Gibson Dr, Chester, MD 21619
      215 John Gibson Dr, Chester, MD 21619
      /60

      Est $577,928 Not Listed For Sale

      • 3 Beds
      • 4 Baths
      • 2,240 Sq Ft

      215 John Gibson Dr, Chester, MD 21619

      215 John Gibson Dr, Chester, MD 21619
  • 131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    131 Flycatcher Way Unit 36474700, Chester, MD 21619
    /10

    $744,900 New Construction

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

    Taylor Plan at K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series, Chester, MD 21619

    Secluded bedroom 2 and bath off foyer for overnight guests. Stylish home office off foyer for working from home. Open & airy great room with adjacent dining area. Striking kitchen with island & tons of cabinet space. Luxurious primary suite with oversized walk-in closet. Palatial primary bath with roomy shower. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36474700, Chester, MD 21619
  • 121 Wheelhouse Way Unit 42, Chester, MD 21619
    121 Wheelhouse Way Unit 42, Chester, MD 21619
    121 Wheelhouse Way Unit 42, Chester, MD 21619
    /32

    $779,900 Sold Sep 11, 2025

    • 1,900 Sq Ft
    • $410/SF
    • 2 Beds
    • 2.5 Baths
    • Built 2025

    121 Wheelhouse Way Unit 42, Chester, MD 21619

    Charming gourmet kitchen featuring designer cabinets & center island.Connected dining area & great room for seamless flow.Convenient dry bar & electric firepelace in main living spaces.Peaceful owner's suite & bath with walk-in closet.Organized home office for leisure activities.Versatile balcony for outdoor enjoyment.

    K. Hovnanian Homes

    121 Wheelhouse Way Unit 42, Chester, MD 21619
    • 2629 Cecil Dr, Chester, MD 21619
      2629 Cecil Dr, Chester, MD 21619
      2629 Cecil Dr, Chester, MD 21619
      /20

      Est $535,500 Not Listed For Sale

      2629 Cecil Dr, Chester, MD 21619

      2629 Cecil Dr, Chester, MD 21619
  • 131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
    /12

    $876,900 New Construction

    • 4 Beds
    • 3.5 Baths
    • 3,512 Sq Ft

    Mykonos Plan at K. Hovnanian’s® Four Seasons at Kent Island - 60' Island Series, Chester, MD 21619

    Private home office off foyer for working from home. Formal dining room off foyer for entertaining guests. Open and airy floorplan with spacious great room. Striking kitchen with large center island. Luxurious primary suite with oversized walk-in closet. Relaxing primary bath with optional freestanding tub. Convenient 3-car tandem garage for additional storage.

    Builder Photo

    K. Hovnanian Homes

    Builder

    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • 330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    330 Macum Creek Dr, Chester, MD 21619
    /55

    $989,000 Sold Sep 11, 2025

    • 3,949 Sq Ft
    • $250/SF
    • 27 Days On Market
    • 4 Beds
    • 3.5 Baths
    • Built 2015

    330 Macum Creek Dr, Chester, MD 21619

    Great price on this home with tons of upgrades! Sellers have found Home of Choice. Welcome home to luxurious living Gibson's Grant! This stunning home offers a perfect blend of luxury and functionality, featuring extensive upgrades throughout. The backyard is an entertainer’s dream with a custom patio, covered outdoor kitchen, bonus grassy area for pets or play, and a fully fenced yard. A former

    Biana Arentz Coldwell Banker Realty

    330 Macum Creek Dr, Chester, MD 21619
    • 2510 Roberta Dr, Chester, MD 21619
      2510 Roberta Dr, Chester, MD 21619
      2510 Roberta Dr, Chester, MD 21619
      /12

      Est $485,943 Not Listed For Sale

      2510 Roberta Dr, Chester, MD 21619

      2510 Roberta Dr, Chester, MD 21619
  • 54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    54A Queen Caroline Ct, Chester, MD 21619
    /43

    $415,000

    • 2 Beds
    • 2.5 Baths
    • 1,280 Sq Ft

    54A Queen Caroline Ct, Chester, MD 21619

    Price Improvement...End Unit in Sought-After Queens Landing – A Waterfront Lifestyle Awaits!Don’t miss this spacious end unit in the highly desirable Queens Landing community! Featuring two primary bedroom suites with private baths, this home offers the perfect blend of comfort and functionality. The expansive kitchen is a chef’s dream, boasting granite countertops, stainless steel

    Darlene Winegardner RE/MAX Executive

    54A Queen Caroline Ct, Chester, MD 21619
  • 211 Switchgrass Way Unit 1531, Chester, MD 21619
    211 Switchgrass Way Unit 1531, Chester, MD 21619
    211 Switchgrass Way Unit 1531, Chester, MD 21619
    /88

    $734,900 Sold Sep 10, 2025

    • 2,602 Sq Ft
    • $282/SF
    • 27 Days On Market
    • 3 Beds
    • 2.5 Baths
    • Built 2025

    211 Switchgrass Way Unit 1531, Chester, MD 21619

    Discover effortless living in the Chester, a well-appointed 3-bedroom, 2.5-bath home with a 1-car garage, thoughtfully designed for both everyday comfort and style. This home blends clean lines with upgraded finishes to create a welcoming and functional retreat.Enjoy cozy evenings by the electric fireplace, or entertain with ease thanks to a built-in dry bar—perfect for hosting or

    Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1531, Chester, MD 21619
    • 55 Queen Caroline Ct, Chester, MD 21619
      55 Queen Caroline Ct, Chester, MD 21619
      55 Queen Caroline Ct, Chester, MD 21619
      /48

      Est $330,039 Not Listed For Sale

      • 2 Beds
      • 2 Baths
      • 1,370 Sq Ft

      55 Queen Caroline Ct, Chester, MD 21619

      55 Queen Caroline Ct, Chester, MD 21619
  • 170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    170 Harrier Way Unit 11, Chester, MD 21619
    /71

    $499,000

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

    170 Harrier Way Unit 11, Chester, MD 21619

    ***Redfin powered by Rocket Mortgage Preferred Pricing*** Enjoy with a 1% lower interest rate for your initial year or potential savings of up to $6,000 on your closing costs when you finance with Rocket Mortgage*** Move-In Ready 2-Bedroom Condo in Four Seasons at Kent Island! Discover this stunning 2-bedroom, 2.5-bath condo in the sought-after 55+ community of Four Seasons at Kent

    Scott Swahl Redfin Corp

    170 Harrier Way Unit 11, Chester, MD 21619
  • 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
    • 104 John Gibson Dr, Chester, MD 21619
      104 John Gibson Dr, Chester, MD 21619
      104 John Gibson Dr, Chester, MD 21619
      /34

      Est $656,246 Not Listed For Sale

      • 4 Beds
      • 3 Baths
      • 2,464 Sq Ft

      104 John Gibson Dr, Chester, MD 21619

      104 John Gibson Dr, Chester, MD 21619
  • 157 John Gibson Dr, Chester, MD 21619
    157 John Gibson Dr, Chester, MD 21619
    157 John Gibson Dr, Chester, MD 21619
    /76

    $700,000

    • 4 Beds
    • 2.5 Baths
    • 2,252 Sq Ft

    157 John Gibson Dr, Chester, MD 21619

    Welcome to this stunning colonial, in the amenity-rich and highly sought-after community of Gibson’s Grant! This 4-bedroom, 2.5-bath colonial offers the perfect blend of comfort, style, and functionality—all just minutes from the Bay Bridge. The main level features an inviting open floor plan with tile flooring, hardwoods in the dining room, and a dedicated office with custom built-in shelving.

    Ryan Briggs Anne Arundel Properties, Inc.

    157 John Gibson Dr, 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
    • 243 Evelyne St, Chester, MD 21619
      243 Evelyne St, Chester, MD 21619
      243 Evelyne St, Chester, MD 21619
      /55

      Est $675,915 Not Listed For Sale

      • 3 Beds
      • 2.5 Baths
      • 2,386 Sq Ft

      243 Evelyne St, Chester, MD 21619

      243 Evelyne St, Chester, MD 21619
  • 141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    141 Switchgrass Way Unit 34, Chester, MD 21619
    /61

    $684,950

    • 3 Beds
    • 2.5 Baths
    • 2,600 Sq Ft

    141 Switchgrass Way Unit 34, Chester, MD 21619

    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

    Ralph Kennedy RE/MAX Executive

    141 Switchgrass Way Unit 34, 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

Showing Results 1 - 40, Page 1 of 18

Maryland Queen Annes County Chester

Real Estate & Homes

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 43 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 $599,900, up 4% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$599,900
Median Single Family Sale Price
$649,000
Median Townhouse Sale Price
$420,000
Median 2 Bedroom Sale Price
$524,900
Median 1 Bedroom Sale Price
$306,500
Average Price Per Sq Ft
$294
Number of Homes for Sale
65
Last 12 months Home Sales
183
Months of Supply
4.30
Median List Price
$595,000
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
4%
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