5,214

Chester, MD Homes

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  • 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

    $560,000

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

    4000 Herons Nest Way Unit 22, Chester, MD 21619

    Four Seasons @ Kent Island - 55+ Community - 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 cooktop

    Agent Photo

    Carol Tinnin

    RE/MAX Leading Edge

    (410) 390-0346

    4000 Herons Nest Way Unit 22, Chester, MD 21619
  • 8013 Bridgepointe Dr, Chester, MD 21619
    8013 Bridgepointe Dr, Chester, MD 21619
    8013 Bridgepointe Dr, Chester, MD 21619
    /17

    $2,500 Per Month

    • 2 Beds
    • 2 Baths
    • 1,285 Sq Ft
    • Condo for Rent

    8013 Bridgepointe Dr, Chester, MD 21619

    Welcome to your new home in Chester, MD! This charming property offers a comfortable living space in a welcoming community. Located conveniently nearby, you'll find fantastic restaurants perfect for enjoying meals out and socializing. Also convenient to Rt 50, golf and outlet shopping.Key property features include a large new deck that spans the length of the back of the house, central

    (443) 981-2425

    8013 Bridgepointe Dr, 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 $491,854

    Last Listing Agent Beth Bearinger Keller Williams Gateway LLC

    203 Barren Ridge Rd, Chester, MD 21619
    • 212 Switchgrass Way Unit 1641, Chester, MD 21619
      212 Switchgrass Way Unit 1641, Chester, MD 21619
      212 Switchgrass Way Unit 1641, Chester, MD 21619
      /56

      Not Listed For Sale

      212 Switchgrass Way Unit 1641, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2024
      212 Switchgrass Way Unit 1641, Chester, MD 21619

      Last Sold Summary

      • $390/SF
      • 1 Day On Market
      • Last Sold Price $1,014,900
      • Apr 28, 2025

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • 3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    3 D Queen Victoria Ct, Chester, MD 21619
    /9

    $269,000

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    3 D Queen Victoria Ct, Chester, MD 21619

    Welcome home to Queens Landing. One bedroom condo with open concept kitchen and living room. The spacious bedroom has plenty of closet space and access to a gated private courtyard with locked storage area. Laundry closet is conveniently situated off the bedroom. Move in ready with fresh paint throughout, new LVP floors in the living areas, and new carpet in the bedroom. Queens Landing is a

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (410) 888-0022

    3 D Queen Victoria Ct, 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: 2256460SENIOR 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 06/01/2026.CALL TODAY TO ANSWER ANY QUESTIONS YOU HAVE.BLYTHE LARRIMORE OSM

    (443) 569-4059

    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 $1,017,997

    Last Listing Agent Annie Eaton Coldwell Banker Realty

    318 Old Point Rd, Chester, MD 21619
    • 212 Switchgrass Way Unit 1642, Chester, MD 21619
      212 Switchgrass Way Unit 1642, Chester, MD 21619
      212 Switchgrass Way Unit 1642, Chester, MD 21619
      /48

      Not Listed For Sale

      212 Switchgrass Way Unit 1642, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,900 Sq Ft
      • Built 2024
      212 Switchgrass Way Unit 1642, Chester, MD 21619

      Last Sold Summary

      • $376/SF
      • 96 Days On Market
      • Last Sold Price $714,900
      • May 01, 2025

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

  • 1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    1868 Roberta Dr, Chester, MD 21619
    /42

    $744,500

    • 5 Beds
    • 3.5 Baths
    • 3,250 Sq Ft

    1868 Roberta Dr, Chester, MD 21619

    Price improvement! Motivated sellers. This custom built home offers the perfect opportunity to live just minutes away from the Chesapeake Bay Bridge and Route 50, offering partial water views and a layout designed for both everyday living and effortless entertaining. The main level features 12 foot ceilings and oversized 6 foot windows that create bright, open living spaces. A vaulted morning

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 446-2477

    1868 Roberta Dr, Chester, MD 21619
  • 6006 Bridgepointe Dr, Chester, MD 21619
    6006 Bridgepointe Dr, Chester, MD 21619
    6006 Bridgepointe Dr, Chester, MD 21619
    /25

    $2,600 Per Month

    • 2 Beds
    • 2 Baths
    • 1,232 Sq Ft
    • Condo for Rent

    6006 Bridgepointe Dr, Chester, MD 21619

    Suzanne Hitt Coldwell Banker Waterman Realty

    6006 Bridgepointe Dr, 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 $436,549

    Last Listing Agent Dina Baxter Rosendale Realty

    1407 Calvert Rd, Chester, MD 21619
    • 212 Switchgrass Way Unit 1644, Chester, MD 21619
      212 Switchgrass Way Unit 1644, Chester, MD 21619
      212 Switchgrass Way Unit 1644, Chester, MD 21619
      /56

      Not Listed For Sale

      212 Switchgrass Way Unit 1644, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,602 Sq Ft
      • Built 2024
      212 Switchgrass Way Unit 1644, Chester, MD 21619

      Last Sold Summary

      • $275/SF
      • 74 Days On Market
      • Last Sold Price $714,900
      • Apr 28, 2025

      Last Listing Agent Mary Anne Kowalewski KOVO Realty

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

    $579,000

    • 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 deck, built

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 222-1760

    126 Watermans Cove Ln, Chester, MD 21619
  • 2201 Main St Unit 105, Chester, MD 21619
    2201 Main St Unit 105, Chester, MD 21619
    2201 Main St Unit 105, Chester, MD 21619
    /12

    $1,950 Per Month

    • 2 Beds
    • 1.5 Baths
    • 1,200 Sq Ft
    • Chester Centre Apartments

    2201 Main St Unit 105, Chester, MD 21619

    2 bedroom, 1.5 bath townhouse style apartment on the 2nd and 3rd floors of the Chester Centre building. Approximately 1200 square feet. Secure entry door, ample parking, easy walk to restaurants.

    2201 Main St Unit 105, 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

    $624,900 Sold Sep 19, 2025

    211 Switchgrass Way Unit 1524, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 2,602 Sq Ft
    • Built 2024

    Last Sold Summary

    • $240/SF
    • 147 Days On Market

    Last Listing Agent Mary Anne Kowalewski KOVO Realty

    211 Switchgrass Way Unit 1524, Chester, MD 21619
    • 136 Evelyne St, Chester, MD 21619
      136 Evelyne St, Chester, MD 21619
      136 Evelyne St, Chester, MD 21619
      /81

      Est $805,208 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

      • 6% Above List Price
      • $274/SF
      • 102 Days On Market
      • Last Sold Price $760,000
      • Sep 25, 2023

      Last Listing Agent Kathleen Higginbotham Samson Properties

  • 134 Mchenny Ct, Chester, MD 21619
    134 Mchenny Ct, Chester, MD 21619
    134 Mchenny Ct, Chester, MD 21619
    /31

    $615,000

    • 3 Beds
    • 2.5 Baths
    • 1,839 Sq Ft

    134 Mchenny Ct, Chester, MD 21619

    Welcome home to this beautifully maintained three-bedroom, two-and-a-half-bath home in the sought-after waterfront community of Gibson’s Grant, where lifestyle and a prime Kent Island location come together effortlessly. A welcoming front porch sets the tone, leading into an open-concept main level designed for both everyday living and entertaining. The spacious living room with propane fireplace

    Agent Photo

    Biana Arentz

    Coldwell Banker Realty

    (667) 771-2810

    134 Mchenny Ct, Chester, MD 21619
  • 226 Bentons Pleasure Rd, Chester, MD 21619
    226 Bentons Pleasure Rd, Chester, MD 21619
    226 Bentons Pleasure Rd, Chester, MD 21619
    /49

    $4,500 Per Month

    • 4 Beds
    • 3 Baths
    • 2,876 Sq Ft
    • House for Rent

    226 Bentons Pleasure Rd, Chester, MD 21619

    Awesome water front living on Cox Creek! This wonderful, spacious Home is a must see on Kent Islands in popular Bentons Pleasure Neighborhood! HUGE GREAT ROOM AND PRIMARY BEDROOM/BATH ADDITION! Wonderful open concept kitchen/ dining room & great room combo w/stone fireplace, handsome built-in book cases, Brazilian cherry hardwood floors, recessed lighting, custom wet bar, wine cooler and water

    Michael Roenigk Chaney Homes, LLC

    226 Bentons Pleasure Rd, Chester, MD 21619
  • 1713 Bayside Dr, Chester, MD 21619
    1713 Bayside Dr, Chester, MD 21619
    1713 Bayside Dr, Chester, MD 21619
    /30

    $465,000 Sold Jun 10, 2025

    1713 Bayside Dr, Chester, MD 21619

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft
    • Built 1972

    Last Sold Summary

    • $235/SF
    • 42 Days On Market

    Current Estimated Value $481,043

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    1713 Bayside Dr, Chester, MD 21619
    • 316 Macum Creek Dr, Chester, MD 21619
      316 Macum Creek Dr, Chester, MD 21619
      316 Macum Creek Dr, Chester, MD 21619
      /79

      Est $846,617 Not Listed For Sale

      316 Macum Creek Dr, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,901 Sq Ft
      • Built 2015
      316 Macum Creek Dr, Chester, MD 21619

      Last Sold Summary

      • 5% Above List Price
      • $279/SF
      • 38 Days On Market
      • Last Sold Price $810,000
      • Oct 22, 2024

      Last Listing Agent Violeta Aguirre Long & Foster

  • 135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    135 Nauset Ln, Chester, MD 21619
    /81

    $799,999

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

    135 Nauset Ln, Chester, MD 21619

    If you’ve ever dreamed of waking up and feeling like you’re on vacation—but with the comforts of home—welcome to 135 Nauset Lane. Tucked into a quiet corner of Kent Island’s Four Seasons community, this home isn’t just beautiful—it’s part of a lifestyle that’s hard to find and even harder to leave. The sellers were first drawn here by the energy of the community and the resort-style amenities.

    Agent Photo

    Riley White

    Real Broker, LLC - Annapolis

    (667) 226-9287

    135 Nauset Ln, Chester, MD 21619
  • 1812 Main St Unit 202, Chester, MD 21619
    1812 Main St Unit 202, Chester, MD 21619
    1812 Main St Unit 202, Chester, MD 21619
    /32

    $1,650 Per Month

    • 1 Bed
    • 1 Bath
    • 926 Sq Ft
    • Condo for Rent

    1812 Main St Unit 202, Chester, MD 21619

    Modern, energy-efficient luxury apartment for lease offering 926 sq ft of thoughtfully designed living space. This oversized 1-bedroom, 1-bath unit stands apart from typical apartment living with an open, spacious layout and quality finishes throughout. Luxury vinyl flooring runs through the foyer, hallway, kitchen, dining, and family room. The well-appointed full-size kitchen features

    Jennifer Norfolk Coldwell Banker Waterman Realty

    1812 Main St Unit 202, 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 K. Hovnanian’s® Four Seasons at Kent Island - 40' Bay Series

    117 Redstart Dr, Chester, MD 21619
    • 163 Claiborne St, Chester, MD 21619
      163 Claiborne St, Chester, MD 21619
      163 Claiborne St, Chester, MD 21619
      /46

      Est $623,564 Not Listed For Sale

      163 Claiborne St, Chester, MD 21619

      • 2 Beds
      • 2.5 Baths
      • 1,824 Sq Ft
      • Built 2012
      163 Claiborne St, Chester, MD 21619

      Last Sold Summary

      • 4% Above List Price
      • $329/SF
      • 3 Days On Market
      • Last Sold Price $600,000
      • Oct 25, 2023

      Last Listing Agent Dave Luptak Long & Foster

  • 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 Coming Soon

    • 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

    Agent Photo

    Timothy McIntyre

    The KW Collective

    (667) 290-8908

    190 Harrier Way Unit 21, Chester, MD 21619
  • 29D Queen Mary Ct, Chester, MD 21619
    29D Queen Mary Ct, Chester, MD 21619
    29D Queen Mary Ct, Chester, MD 21619
    /37

    $2,700 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,440 Sq Ft
    • Townhouse for Rent

    29D Queen Mary Ct, Chester, MD 21619

    Wonderful Queens Landing on Kent Island! Totally updated kitchen area with center island and bar stools! *Hardwood floors on main living area! Enclosed sun-room with beautiful views of the lake. Spacious living room with fireplace and built in book cases. Kitchen with Breakfast Bar. Main Bedroom, with Main Bath, also over looks the lake. *This town home is a must see in Queens Landing* Community

    Michael Roenigk Chaney Homes, LLC

    29D Queen Mary Ct, 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 K. Hovnanian’s® Four Seasons at Kent Island - Luxury Condos

    110 Boatswain Way Unit 41, 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 $566,621 Not Listed For Sale

      215 John Gibson Dr, Chester, MD 21619

      • 3 Beds
      • 4 Baths
      • 2,240 Sq Ft
      • Built 2011
      215 John Gibson Dr, Chester, MD 21619

      Last Sold Summary

      • $252/SF
      • 25 Days On Market
      • Last Sold Price $565,000
      • Sep 10, 2024

      Last Listing Agent Catherine Watson - Bye RE/MAX

  • 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

    $848,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36476268, Chester, MD 21619
  • 11F Queen Elizabeth Ct, Chester, MD 21619
    11F Queen Elizabeth Ct, Chester, MD 21619
    11F Queen Elizabeth Ct, Chester, MD 21619
    /34

    $2,100 Per Month

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft
    • Condo for Rent

    11F Queen Elizabeth Ct, Chester, MD 21619

    Here is your chance to live in one of Kent Island's favorite neighborhoods!! Nicely renovated waterfront condo features spectacular sunrises & moonlit evenings! Separate bedroom on waterside. Neutral decor and new glass top range and granite counter top in kitchen. Mirrored wall in family room makes the room seem larger and more open! New wood-look vinyl flooring, ceramic tile and new tub/shower

    Mary Stevens Long & Foster Real Estate, Inc.

    11F Queen Elizabeth Ct, 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 $658,078

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    132 Claiborne St, Chester, MD 21619
    • 147 Carriage Heath, Chester, MD 21619
      147 Carriage Heath, Chester, MD 21619
      147 Carriage Heath, Chester, MD 21619
      /70

      Est $728,387 Not Listed For Sale

      147 Carriage Heath, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,148 Sq Ft
      • Built 2015
      147 Carriage Heath, Chester, MD 21619

      Last Sold Summary

      • 2% Above List Price
      • $333/SF
      • 20 Days On Market
      • Last Sold Price $715,000
      • Oct 15, 2024

      Last Listing Agent Yael Beckman Coldwell Banker (NRT-Southeast-MidAtlantic)

  • 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

    $858,990 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36451844, Chester, MD 21619
  • 101 Dundee Ave Unit 202, Chester, MD 21619
    101 Dundee Ave Unit 202, Chester, MD 21619
    101 Dundee Ave Unit 202, Chester, MD 21619
    /12

    $1,400 Per Month

    • 1 Bed
    • 1 Bath
    • 3,596 Sq Ft
    • Condo for Rent

    101 Dundee Ave Unit 202, Chester, MD 21619

    1 bedroom 1 bath apartment, second floor with balcony. Freshley painted, new LVP flooring. Reserved parking for 1 vehicle, overflow parking for one other vehicle. Water & sewer, trash removal and parking included. Small pets under 35lbs welcomed on a case-by-case basis. Secure building.

    Cindy Jacobs Maryland Residential Management Co

    101 Dundee Ave Unit 202, 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

    112 Harbour Sound Dr, Chester, MD 21619

    • 2 Beds
    • 3.5 Baths
    • 2,131 Sq Ft
    • Built 1989

    Last Sold Summary

    • $254/SF
    • 86 Days On Market

    Current Estimated Value $515,235

    Last Listing Agent Carlos Larraz Annapolis Properties LLC

    112 Harbour Sound Dr, Chester, MD 21619
    • 2629 Cecil Dr, Chester, MD 21619
      2629 Cecil Dr, Chester, MD 21619
      2629 Cecil Dr, Chester, MD 21619
      /20

      Not Listed For Sale

      2629 Cecil Dr, Chester, MD 21619

      2629 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 4,184% Above List Price
      • 114 Days On Market
      • Last Sold Price $12,500
      • Aug 17, 2023

      Last Listing Agent Gretchen Wichlinski Compass

  • 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 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.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36477689, Chester, MD 21619
  • 400 Schooner Way, Chester, MD 21619
    400 Schooner Way, Chester, MD 21619
    400 Schooner Way, Chester, MD 21619
    /40

    $2,600 Per Month

    • 3 Beds
    • 2.5 Baths
    • 1,747 Sq Ft
    • Townhouse for Rent

    400 Schooner Way, Chester, MD 21619

    **Live the Island Lifestyle**Bayside Town Home w/3 Levels**2 BR possible 3rd on Lower Level**Garage Parking**Looks out over Pond**Community Offers, Swimming Pool, Tennis Courts, Exercise Room**Close to Route 50 for Easy Access**$75.00 per Adult Processing Fee**Walk to Restaurants**

    Deborah Savoie Long & Foster Real Estate, Inc.

    400 Schooner Way, 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 $487,211

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

    1337 Queen Anne Dr, Chester, MD 21619
    • 26C Piney Narrows Rd, Chester, MD 21619
      26C Piney Narrows Rd, Chester, MD 21619
      26C Piney Narrows Rd, Chester, MD 21619
      /36

      Not Listed For Sale

      26C Piney Narrows Rd, Chester, MD 21619

      • 611 Sq Ft
      • Built 1981
      26C Piney Narrows Rd, Chester, MD 21619

      Last Sold Summary

      • $53/SF
      • 32 Days On Market
      • Last Sold Price $32,500
      • Apr 16, 2025

      Last Listing Agent Lisa Lynch Keller Williams Realty

Showing Results 1 - 40, Page 1 of 18

Maryland Queen Anne's County Chester

Real Estate & Homes

Home Trends in Chester, MD

On average, homes in Chester, MD sell after 251 days on the market compared to the national average of 57 days. The median sale price for homes in Chester, MD over the last 12 months is $641,500, up 9% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$641,500
Median Single Family Sale Price
$699,209
Median Townhouse Sale Price
$370,000
Median 2 Bedroom Sale Price
$557,000
Median 1 Bedroom Sale Price
$294,500
Average Price Per Sq Ft
$301
Number of Homes for Sale
77
Last 12 months Home Sales
216
Months of Supply
4.30
Median List Price
$663,917
Median Change From 1st List Price
0%
Median Home Sale Price YoY Change
9%
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