5,230

Chester, MD Homes

Section Image Section Image Section Image
  • 126 Watermans Cove Ln, Chester, MD 21619
    126 Watermans Cove Ln, Chester, MD 21619
    126 Watermans Cove Ln, Chester, MD 21619
    /44

    $559,000

    $20K PRICE DROP
    • 3 Beds
    • 3 Baths
    • 1,536 Sq Ft

    126 Watermans Cove Ln, Chester, MD 21619

    Welcome to this beautifully maintained 3-bedroom, 2.5-bathroom home in the Waterman’s Cove community in Chester. Nestled on a quiet street along scenic Cox Creek, this charming property offers the perfect blend of comfort, style, and convenience.An inviting front porch welcomes you home, while water views greet you upon arrival and can also be enjoyed from the spacious rear composite

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    126 Watermans Cove Ln, 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
    /53

    $4,000 Per Month

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Condo for Rent

    190 Harrier Way Unit 24, Chester, MD 21619

    Four Seasons @ Kent Island - A Premiere 55+ Community - Luxury, Upscale Rental Offered as Rent OR Rent with Option to Buy in Resort-Like Community - Largest Model Available, Severn Model, 2600sf, 2nd Floor End Unit, Elevator Building + Private Garage + Private Driveway + Bonus Conditioned, Lobby Level Storage Closet. Features 3 Bedrooms, 2.5 Baths, Unfurnished, Tons of Closet Space, Bright End

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    190 Harrier Way Unit 24, Chester, MD 21619
  • 203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    203 Barren Ridge Rd, Chester, MD 21619
    /53

    $475,000

    Sold Sep 29, 2025

    203 Barren Ridge Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 2,072 Sq Ft
    • Built 1988

    Last Sold Summary

    • $229/SF
    • 38 Days On Market

    Current Estimated Value $512,204

    Last Listing Agent Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619
    • 137 Warbler Way, Chester, MD 21619
      137 Warbler Way, Chester, MD 21619
      137 Warbler Way, Chester, MD 21619
      /81

      Not Listed For Sale

      137 Warbler Way, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 2,147 Sq Ft
      • Built 2024
      137 Warbler Way, Chester, MD 21619

      Last Sold Summary

      • 129 Days On Market

      Last Listing Agent Jennifer Chaney Chaney Homes, LLC

  • 2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    2855 Cox Neck Rd, Chester, MD 21619
    /78

    $1,125,000

    $125K PRICE DROP
    • 4 Beds
    • 4.5 Baths
    • 4,413 Sq Ft

    2855 Cox Neck Rd, Chester, MD 21619

    Located in the prestigious Southwind community, a penisula between Crab Alley Bay & Cox Creek, this elegant contemporary ranch-style home offers an unparalleled lifestyle of luxury and comfort. Spanning over 4,400 sq. ft. of finished space, the interior boasts elegant marble flooring, complemented by crown moldings and built-ins that enhance its sophisticated charm. The gourmet kitchen, featuring

    Agent Photo

    Tricia Wilson

    Wilson Realty & Staging LLC

    2855 Cox Neck Rd, Chester, MD 21619
  • 1540 Postal Rd Unit 210, Chester, MD 21619
    1540 Postal Rd Unit 210, Chester, MD 21619
    /2

    $1,950 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    1540 Postal Rd Unit 210, Chester, MD 21619

    Property Id: 2256460 SENIOR APTS 62+ AT VILLAGE AT CHESTER. ALL APTS ARE TWO BR, ONE BA. ALL APPLIANCES INCLUDED. PETS ALLOWED. STORAGE SPACE COMES WITH LEASE. ONE YEAR LEASE. ELECTRIC AND CABLE ARE TENANTS BILLS. CLOSE TO ALL YOUR NEEDS. AVAILABLE 10/1/2026. CALL TODAY TO ANSWER ANY QUESTIONS YOU HAVE. BLYTHE LARRIMORE OSM

    1540 Postal Rd Unit 210, Chester, MD 21619
  • 318 Old Point Rd, Chester, MD 21619
    318 Old Point Rd, Chester, MD 21619
    318 Old Point Rd, Chester, MD 21619
    /43

    $1,025,000

    Sold Nov 26, 2025

    318 Old Point Rd, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,656 Sq Ft
    • Built 2024

    Last Sold Summary

    • $619/SF
    • 6 Days On Market

    Current Estimated Value $1,062,317

    Last Listing Agent Annie Eaton Coldwell Banker Realty

    318 Old Point Rd, 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

      Not Listed For Sale

      211 Switchgrass Way Unit 1534, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2024
      211 Switchgrass Way Unit 1534, Chester, MD 21619

      Last Sold Summary

      • 56 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • 4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    4000 Herons Nest Way Unit 22, Chester, MD 21619
    /70

    $499,000

    $61K PRICE DROP
    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - Reduced! * Turn-key & Lovely 2nd Floor Condo in Elevator Building with 1 Car Garage plus 1 Car Outdoor Parking and Private, Secure Indoor Storage Area. This Chester Model offers 1900 sf with pond view and winter water views of Macum Creek. Enter to find an expansive, open floor plan featuring a beautiful white Kitchen with quartz counters, propane gas

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 4000 Herons Nest Way Unit 42, Chester, MD 21619
    4000 Herons Nest Way Unit 42, Chester, MD 21619
    4000 Herons Nest Way Unit 42, Chester, MD 21619
    /49

    $4,200 Per Month

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Condo for Rent

    4000 Herons Nest Way Unit 42, Chester, MD 21619

    Four Seasons @ Kent Island 55+ -- FULLY FURNISHED, LUXURY PENTHOUSE RENTAL, TURN-KEY, JUST BRING YOUR CLOTHES -- Fabulous Penthouse/4th Floor Unit, Elevator Building with Private Garage + Driveway Parking & Keyed Storage Closet. Fully Furnished Chester Model, 1900 sf, 2 Bedroom + Den/Office & 2.5 Baths. Balcony Access From Living Room + Primary Bedroom. This is the DREAM! Includes all Furnishings

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    4000 Herons Nest Way Unit 42, Chester, MD 21619
  • 1407 Calvert Rd, Chester, MD 21619
    1407 Calvert Rd, Chester, MD 21619
    /2

    $430,000

    Sold Jan 23, 2026

    1407 Calvert Rd, Chester, MD 21619

    • 3 Beds
    • 1.5 Baths
    • 1,693 Sq Ft
    • Built 1966

    Last Sold Summary

    • $254/SF
    • 2 Days On Market

    Current Estimated Value $451,186

    Last Listing Agent Dina Baxter Rosendale Realty

    1407 Calvert 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

      Not Listed For Sale

      211 Switchgrass Way Unit 1523, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2025
      211 Switchgrass Way Unit 1523, Chester, MD 21619

      Last Sold Summary

      • 16 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • 108 Blenny Ln, Chester, MD 21619
    108 Blenny Ln, Chester, MD 21619
    108 Blenny Ln, Chester, MD 21619
    /26

    $389,900

    • 3 Beds
    • 2.5 Baths
    • 1,899 Sq Ft

    108 Blenny Ln, Chester, MD 21619

    Bayside In Kent Island Located in the Popular Community of Bayside just minutes from the Bay Bridge and all Kent Island has to offer! This lovely End Unit Townhome with Garage is very well maintained and in move in condition. It features 3 levels above ground. Enter at ground level which includes Garage, Foyer, Laundry and a bright and sunny 1st floor Family Room with Sliding Glass Doors to a

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    108 Blenny Ln, Chester, MD 21619
  • 2201 Main St Unit 104, Chester, MD 21619
    2201 Main St Unit 104, Chester, MD 21619
    2201 Main St Unit 104, Chester, MD 21619
    /7

    $1,575 Per Month

    • 3 Beds
    • 1.5 Baths
    • 1,500 Sq Ft
    • Condo for Rent

    2201 Main St Unit 104, Chester, MD 21619

    Property Id: 2880993 1500 square feet, 3 bedrooms, 1.5 baths. Large rooms. Kitchen with pantry and full dining area. New carpet and laminate flooring. Secured entrance. Townhouse-style apartment (living space downstairs, bedrooms upstairs) located on the second and third floors of the Chester Centre building. Security deposit and first month's rent (or pro-rated amount) due at lease

    2201 Main St Unit 104, Chester, MD 21619
  • 1872 Harbor Dr, Chester, MD 21619
    1872 Harbor Dr, Chester, MD 21619
    /2

    $445,000

    Sold Jul 31, 2026

    1872 Harbor Dr, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,486 Sq Ft
    • Built 1961

    Last Sold Summary

    • 8% Below List Price
    • $299/SF
    • 49 Days On Market

    Current Estimated Value $452,572

    Last Listing Agent Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
    • 211 Switchgrass Way Unit 1524, Chester, MD 21619
      211 Switchgrass Way Unit 1524, Chester, MD 21619
      211 Switchgrass Way Unit 1524, Chester, MD 21619
      /88

      Not Listed For Sale

      211 Switchgrass Way Unit 1524, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2024
      211 Switchgrass Way Unit 1524, Chester, MD 21619

      Last Sold Summary

      • 147 Days On Market

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • 1010 Auckland Way, Chester, MD 21619
    1010 Auckland Way, Chester, MD 21619
    1010 Auckland Way, Chester, MD 21619
    /16

    $595,000

    Coming Soon Sep 25
    • 3 Beds
    • 3.5 Baths
    • 2,100 Sq Ft

    1010 Auckland Way, Chester, MD 21619

    Professional Photos Coming Soon - PANORAMIC CHESTER RIVER VIEWS! This fabulous END-UNIT townhome in Kent Island’s sought-after Bayside community offers a special WATERFRONT SETTING with sweeping views of the Chester River as it flows into the Chesapeake Bay. With approximately 2,100 square feet, an abundance of natural light, and water views from so many rooms, this home is all about enjoying the

    Agent Photo

    Lori Woods-Fortney

    Berkshire Hathaway HomeServices Homesale Realty

    1010 Auckland Way, Chester, MD 21619
  • 1540 Postal Rd Unit 107, Chester, MD 21619
    1540 Postal Rd Unit 107, Chester, MD 21619
    /2

    $1,750 Per Month

    • 2 Beds
    • 1 Bath
    • 850 Sq Ft
    • Condo for Rent

    1540 Postal Rd Unit 107, Chester, MD 21619

    Property Id: 2841646 Great location to fit all your needs. Restaurants, shopping, parks and the Bay are close. Great spot to hang your hat! Call today!

    1540 Postal Rd Unit 107, Chester, MD 21619
  • 117 Redstart Dr, Chester, MD 21619
    117 Redstart Dr, Chester, MD 21619
    117 Redstart Dr, Chester, MD 21619
    /8

    $849,990

    Sold Dec 10, 2025

    117 Redstart Dr, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,010 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $423/SF
    • 7 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Single Family

    117 Redstart Dr, 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

      Est $835,973

      Not Listed For Sale

      121 John Gibson Dr, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,760 Sq Ft
      • Built 2010
      121 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • 7 Days On Market

      Last Listing Agent Tara Trout Samson Properties

  • 231 Evelyne St, Chester, MD 21619
    231 Evelyne St, Chester, MD 21619
    /2

    $815,000

    Coming Soon Sep 30
    • 4 Beds
    • 2.5 Baths
    • 2,870 Sq Ft

    231 Evelyne St, Chester, MD 21619

    This beautiful coastal Colonial home in Gibsons Grant offers a perfect blend of comfort and style. With 4 spacious bedrooms and 2.5 bathrooms, the open floor plan invites warmth and connection. Enjoy cooking up your favorite feast in the upgraded kitchen featuring an island, built-in appliances, and endless countertops. The family room, complete with a propane fireplace, is perfect for gatherings

    Agent Photo

    Tricia Wilson

    Wilson Realty & Staging LLC

    231 Evelyne St, Chester, MD 21619
  • 107 Chessie Ct, Chester, MD 21619
    107 Chessie Ct, Chester, MD 21619
    107 Chessie Ct, Chester, MD 21619
    /9

    $2,600 Per Month

    • 4 Beds
    • 2.5 Baths
    • 1,840 Sq Ft
    • House for Rent

    107 Chessie Ct, Chester, MD 21619

    Nestled in the charming Clayborne Woods neighborhood, this delightful 4-bedroom, 2.5-bathroom Colonial home offers a perfect blend of comfort and style. With 1,840 sq. ft. of living space, the interior features plush carpeting, ceiling fans, and a spacious combination kitchen/dining area, ideal for gatherings. Enjoy the convenience of modern appliances, including a built-in microwave, dishwasher,

    Kevin Waterman Coldwell Banker Waterman Realty

    107 Chessie Ct, Chester, MD 21619
  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $787,500

    Sold Aug 07, 2026

    135 Nauset Ln, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 2,795 Sq Ft
    • Built 2020

    Last Sold Summary

    • 3% Below List Price
    • $282/SF
    • 230 Days On Market

    Current Estimated Value $804,439

    Last Listing Agent Riley White Real Broker, LLC - Annapolis

    135 Nauset Ln, Chester, MD 21619
    • 308 Dominion Rd, Chester, MD 21619
      308 Dominion Rd, Chester, MD 21619
      308 Dominion Rd, Chester, MD 21619
      /35

      Est $340,879

      Not Listed For Sale

      308 Dominion Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,280 Sq Ft
      • Built 1955
      308 Dominion Rd, Chester, MD 21619

      Last Sold Summary

      • 193 Days On Market

      Last Listing Agent Tyler Burch Burch Real Estate Group, LLC

  • 2882 Cox Neck Rd, Chester, MD 21619
    2882 Cox Neck Rd, Chester, MD 21619
    2882 Cox Neck Rd, Chester, MD 21619
    /93

    $2,400,000

    Under Contract
    • 4 Beds
    • 3.5 Baths
    • 4,331 Sq Ft

    2882 Cox Neck Rd, Chester, MD 21619

    Discover an exquisite Mediterranean-style residence nestled in the prestigious Southwind community, where luxury meets comfort while enjoying breathtaking sunset views. This stunning 4-bedroom, 3.5-bathroom home boasts 4,331 sq. ft. The gourmet kitchen features high-end stainless steel appliances, including a built-in microwave, wall oven, and a sleek cooktop, ensuring culinary excellence. Step

    Agent Photo

    Tricia Wilson

    Wilson Realty & Staging LLC

    2882 Cox Neck Rd, Chester, MD 21619
  • 321 Piney Narrows Rd Unit 1, Chester, MD 21619
    321 Piney Narrows Rd Unit 1, Chester, MD 21619
    321 Piney Narrows Rd Unit 1, Chester, MD 21619
    /16

    $2,000 Per Month

    • 2 Beds
    • 1 Bath
    • 950 Sq Ft
    • Townhouse for Rent

    321 Piney Narrows Rd Unit 1, Chester, MD 21619

    Everything Is brand new! This unique little apartment has been freshly created inside of a building right near a marina. Enjoy all that the Kent Island lifestyle has to offer. You are close to everything. This unit is offered furnished or not-your choice. Check out this bright, cheerful and newly renovated unit. Six month lease available for $2400/mo. This unit is also being offered as a

    Terri Gable Chesapeake Real Estate Associates, LLC

    321 Piney Narrows Rd Unit 1, Chester, MD 21619
  • 110 Boatswain Way Unit 41, Chester, MD 21619
    110 Boatswain Way Unit 41, Chester, MD 21619
    110 Boatswain Way Unit 41, Chester, MD 21619
    /18

    $949,990

    Sold Apr 22, 2026

    110 Boatswain Way Unit 41, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 9% Below List Price
    • $365/SF
    • 35 Days On Market

    K. Hovnanian Homes Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 41, 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

      Est $529,000

      Not Listed For Sale

      112 Harbour Sound Dr, Chester, MD 21619

      • 2 Beds
      • 3.5 Baths
      • 2,131 Sq Ft
      • Built 1989
      112 Harbour Sound Dr, Chester, MD 21619

      Last Sold Summary

      • 86 Days On Market

      Last Listing Agent Carlos Larraz Annapolis Properties LLC

  • 47 Queen Anne Way, Chester, MD 21619
    47 Queen Anne Way, Chester, MD 21619
    47 Queen Anne Way, Chester, MD 21619
    /52

    $550,000

    • 2 Beds
    • 2.5 Baths
    • 1,616 Sq Ft

    47 Queen Anne Way, Chester, MD 21619

    Set directly along the Chester River in desirable Queen’s Landing, this waterfront home puts the water at the center of everyday living, with incredible views from the main level, sunroom, patio, and both upstairs bedrooms. The shoreline feels remarkably close, creating a peaceful backdrop that can be enjoyed from nearly every principal living space. Renovations and upgrades throughout complement

    Agent Photo

    Debra Noone

    Northrop Realty

    47 Queen Anne Way, Chester, MD 21619
  • 1606 Postal Rd Unit C, Chester, MD 21619
    1606 Postal Rd Unit C, Chester, MD 21619
    1606 Postal Rd Unit C, Chester, MD 21619
    /17

    $2,200 Per Month

    • 4 Beds
    • 2 Baths
    • 5,128 Sq Ft
    • House for Rent

    1606 Postal Rd Unit C, Chester, MD 21619

    Apartment #C-Upstairs all on one level 4-bedroom, 2 bath unit, just painted and new LVP flooring & carpet added. Plenty of parking in building lot. Easy access to Rt 50, close to shopping, restaurants. Trash, parking, grounds maintenance and water sewer included in rent. One pet under 35lbs allowed with pet rent.

    Cindy Jacobs Maryland Residential Management Co

    1606 Postal Rd Unit C, Chester, MD 21619
  • 132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    132 Claiborne St, Chester, MD 21619
    /40

    $640,000

    Sold Jan 05, 2026

    132 Claiborne St, Chester, MD 21619

    • 3 Beds
    • 3.5 Baths
    • 2,400 Sq Ft
    • Built 2011

    Last Sold Summary

    • $267/SF
    • 20 Days On Market

    Current Estimated Value $679,188

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    132 Claiborne St, Chester, MD 21619
    • 208 Ringneck Ct, Chester, MD 21619
      208 Ringneck Ct, Chester, MD 21619
      208 Ringneck Ct, Chester, MD 21619
      /66

      Est $330,622

      Not Listed For Sale

      208 Ringneck Ct, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,747 Sq Ft
      • Built 1995
      208 Ringneck Ct, Chester, MD 21619

      Last Sold Summary

      • 98 Days On Market

      Last Listing Agent Phyllis Endrich Long & Foster Real Estate, Inc.

  • 320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    320 Bayberry Dr, Chester, MD 21619
    /90

    $859,900

    • 3 Beds
    • 2 Baths
    • 2,331 Sq Ft

    320 Bayberry Dr, Chester, MD 21619

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    320 Bayberry Dr, Chester, MD 21619
  • 215 Parks Rd, Chester, MD 21619
    215 Parks Rd, Chester, MD 21619
    215 Parks Rd, Chester, MD 21619
    /35

    $3,200 Per Month

    • 2 Beds
    • 1 Bath
    • 645 Sq Ft
    • House for Rent

    215 Parks Rd, Chester, MD 21619

    Craving a WATERFRONT rental with pier, 15,000 lb boat lift, jet-ski lift, nearly 200 feet of shoreline, & sandy beach area on .4 acres just 5 mins from Bay Bridge? Welcome home! Enjoy this 6-Month WATERFRONT playground! Nearly 200' of shoreline with Private, sandy beach, 120' Pier with Boat Lift AND Jet-ski lift, panoramic views of coveted Cox Creek. With generous water depth, ideal location with

    Jennifer Chaney Chaney Homes, LLC

    215 Parks Rd, Chester, MD 21619
  • 2008 Bridgepointe Dr, Chester, MD 21619
    2008 Bridgepointe Dr, Chester, MD 21619
    2008 Bridgepointe Dr, Chester, MD 21619
    /38

    $355,000

    Sold Aug 20, 2026

    2008 Bridgepointe Dr, Chester, MD 21619

    • 2 Beds
    • 2 Baths
    • 1,804 Sq Ft
    • Built 1990

    Last Sold Summary

    • 7% Below List Price
    • $197/SF
    • 111 Days On Market

    Current Estimated Value $380,759

    Last Listing Agent Crystal Smith RE/MAX Executive

    2008 Bridgepointe Dr, Chester, MD 21619
    • 136 Evelyne St, Chester, MD 21619
      136 Evelyne St, Chester, MD 21619
      136 Evelyne St, Chester, MD 21619
      /81

      Est $822,016

      Not Listed For Sale

      136 Evelyne St, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,771 Sq Ft
      • Built 2014
      136 Evelyne St, Chester, MD 21619

      Last Sold Summary

      • 102 Days On Market

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • 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

    $886,990

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

    Mykonos Plan at Four Seasons at Kent Island - Single Family, 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • 215 Kingfisher Ln, Chester, MD 21619
    215 Kingfisher Ln, Chester, MD 21619
    215 Kingfisher Ln, Chester, MD 21619
    /44

    $4,500 Per Month

    • 5 Beds
    • 4.5 Baths
    • 3,225 Sq Ft
    • House for Rent

    215 Kingfisher Ln, Chester, MD 21619

    Try Before You Buy in Four Seasons at Kent Island! Experience the resort-style lifestyle of one of Kent Island’s most sought-after 55+ communities before making a purchase commitment.This nearly new Tuscaloosa model offers 5 bedrooms, 4.5 baths, a bright open floor plan, premium Café appliances, custom closets and window treatments, an oversized garage, and peekaboo Chester River views from

    Jennifer Thomas RE/MAX Executive

    215 Kingfisher Ln, Chester, MD 21619
  • 1337 Queen Anne Dr, Chester, MD 21619
    1337 Queen Anne Dr, Chester, MD 21619
    1337 Queen Anne Dr, Chester, MD 21619
    /77

    $488,000

    Sold Apr 17, 2026

    1337 Queen Anne Dr, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,128 Sq Ft
    • Built 1973

    Last Sold Summary

    • 2% Above List Price
    • $229/SF
    • 15 Days On Market

    Current Estimated Value $489,113

    Last Listing Agent Caitlin Prossner Long & Foster Real Estate, Inc.

    1337 Queen Anne Dr, Chester, MD 21619
    • 232 Shopping Center Rd, Stevensville, MD 21666
      232 Shopping Center Rd, Stevensville, MD 21666
      /2

      Est $998,621

      Not Listed For Sale

      232 Shopping Center Rd, Stevensville, MD 21666

      • 1 Bed
      • 1 Bath
      • 1,000 Sq Ft
      • Built 2009
      232 Shopping Center Rd, Stevensville, MD 21666

Showing Results 1 - 40, Page 1 of 18

Maryland Queen Anne's County

Real Estate & Homes

Home Prices in Chester, MD

The median home sale price in Chester, MD is $689,450, up 15% year-over-year. Homes in Chester sell in 428 days on average, compared to the national average of 55 days.

Home Price Trends

Median Sale Price
$689,450
Median Single Family Sale Price
$749,990
Median Townhouse Sale Price
$372,400
Median 2 Bedroom Sale Price
$634,990
Median 1 Bedroom Sale Price
$338,000
Average Price Per Sq Ft
$309
Number of Homes for Sale
5,230
Last 12 months Home Sales
214
Months of Supply
4.70
Median List Price
$714,900
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
15%
How to Buy a Home How to Finance a Home How to Sell a Home

Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.

Homes.com Licensing Information

§ 442-H New York Standard Operating Procedures

New York Fair Housing Notice

TREC: Information about brokerage services, Consumer protection notice

California DRE #01937601

Contact Homes.com Brokerage

Copyright © 2026 CoStar Group