5,186

Chester, MD Homes

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  • /2

    $205,000 Sold Dec 26, 2025

    1905 Keister Dr, Chester, MD 21619

    • 3 Beds
    • 1 Bath
    • 1,600 Sq Ft
    • Built 1968

    Last Sold Summary

    • $128/SF

    Current Estimated Value $321,034

    Last Listing Agent Elaina Bellas LPT Realty, LLC

    1905 Keister Dr, Chester, MD 21619
    • /35

      Est $404,634 Not Listed For Sale

      28A Queen Mary Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,260 Sq Ft
      • Built 1985
      28A Queen Mary Ct, Chester, MD 21619

      Last Sold Summary

      • 1% Above List Price
      • $317/SF
      • 15 Days On Market

      Last Sold Price $400,000

      Last Listing Agent Thomas Hennerty NetRealtyNow.com, LLC

  • /15

    $275,000

    • Land
    • 0.68 Acre
    • $404,412 per Acre

    0 Parks Rd, Chester, MD 21619

    Kent Island Waterfront on Cox Creek!! Public Sewer available, road frontage is 45ft. This is a flag lot with opening on the waterfront of 108 ft. This property does not have a pier, so please do not go on pier. This is the perfect lot to build your dream home. The natural environment has wildlife and waterfowl and as well as good fishing and crabbing. If you want a piece of the shore-life

    Linda Austin Long & Foster Real Estate, Inc.

    0 Parks Rd, Chester, MD 21619
  • /41

    $853,000 Sold Mar 10, 2026

    162 Kirwans Landing Ln, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,404 Sq Ft
    • Built 1988

    Last Sold Summary

    • $355/SF
    • 104 Days On Market

    Current Estimated Value $928,367

    Last Listing Agent Biana Arentz Coldwell Banker Realty

    162 Kirwans Landing Ln, Chester, MD 21619
    • /23

      Not Listed For Sale

      1437 Cox Neck Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,456 Sq Ft
      • Built 2009
      1437 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • $206/SF
      • 4 Days On Market

      Last Sold Price $300,000

      Last Listing Agent Petra Quinn Realty Navigator

  • /23

    $485,000 Open Sat 11AM - 1PM

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

    1872 Harbor Dr, Chester, MD 21619

    Harbor View Community | Corner Lot | Renovated Rancher with Room to GrowWelcome to 1872 Harbor Drive —a move-in ready ranch-style home that offers the space and updates today’s buyers are searching for. Located in the Matapeake Elementary School district, this home sits on a rare double corner lot with nearly three-quarters of an acre, making it a standout opportunity on Maryland’s Eastern

    Joelle Dolch Cross Street Realtors LLC

    1872 Harbor Dr, Chester, MD 21619
  • /19

    $949,990 Sold Mar 02, 2026

    110 Boatswain Way Unit 34, Chester, MD 21619

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

    Move in Ready Sold Summary

    • 3% Below List Price
    • $365/SF
    • 11 Days On Market

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

    110 Boatswain Way Unit 34, Chester, MD 21619
    • /57

      Est $492,585 Not Listed For Sale

      4E Queen Victoria Way, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,680 Sq Ft
      • Built 1984
      4E Queen Victoria Way, Chester, MD 21619

      Last Sold Summary

      • 7% Above List Price
      • $273/SF
      • 2 Days On Market

      Last Sold Price $459,000

      Last Listing Agent Christopher May Douglas Realty LLC

  • /33

    $499,990 New Construction

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

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

    Open floorplan with plenty of room for your family. Wonderful gourmet kitchen and formal dining area. Private home office for your personal space. Large great room off balcony with large windows to capture the day. Luxurious owner’s suite with spa bath and access to balcony. Large secondary bedroom with access to balcony. Pricing is inclusive of an average location premium.

    K. Hovnanian Homes Builder
    131 Flycatcher Way Unit 36493320, Chester, MD 21619
  • /55

    $565,000 Sold May 19, 2025

    1602 Calvert Rd, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,184 Sq Ft
    • Built 1978

    Last Sold Summary

    • $259/SF
    • 120 Days On Market

    Current Estimated Value $577,262

    Last Listing Agent Dina Baxter Rosendale Realty

    1602 Calvert Rd, Chester, MD 21619
    • /69

      Est $801,100 Not Listed For Sale

      215 Mcguckin St, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,914 Sq Ft
      • Built 2008
      215 Mcguckin St, Chester, MD 21619

      Last Sold Summary

      • 4% Above List Price
      • $264/SF
      • 81 Days On Market

      Last Sold Price $770,000

      Last Listing Agent Deborah Savoie Long & Foster

  • /29

    $525,000 Under Contract

    • 6 Beds
    • 3 Baths
    • 3,500 Sq Ft

    205 Anchor Ln, Chester, MD 21619

    Price Improvement! Need more room? This expansive home is ready to welcome your whole family! With 6 bedrooms, 3 full bathrooms and an over-sized, 4-car garage, there's plenty of space for everyone to spread out and enjoy their own privacy. You'll be delighted by a mix of formal and casual living spaces, including a bright formal living room, a cozy lower-level family room, and a huge screened

    Darlene Winegardner RE/MAX Executive

    205 Anchor Ln, Chester, MD 21619
  • /50

    $812,500 Sold Sep 15, 2025

    121 John Gibson Dr, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,760 Sq Ft
    • Built 2010

    Last Sold Summary

    • $294/SF
    • 7 Days On Market

    Current Estimated Value $816,581

    Last Listing Agent Tara Trout Samson Properties

    121 John Gibson Dr, Chester, MD 21619
    • /36

      Est $485,103 Not Listed For Sale

      1911 Keister Dr, Chester, MD 21619

      • 4 Beds
      • 2 Baths
      • 2,000 Sq Ft
      • Built 1998
      1911 Keister Dr, Chester, MD 21619

      Last Sold Summary

      • 5% Above List Price
      • $230/SF
      • 4 Days On Market

      Last Sold Price $460,000

      Last Listing Agent Charles Cockrill BHHS PenFed (actual)

  • /77

    $485,000 Under Contract

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

    1337 Queen Anne Dr, Chester, MD 21619

    Charming Renovated Ranch in Marling FarmsThis updated three-bedroom, two-and-a-half-bath home is located in water-privileged Marling Farms. Originally built in 1973 and thoughtfully renovated in 2017, the home blends classic architectural charm with modern updates, offering both comfort and timeless appeal.Inside, well-designed living spaces showcase distinctive details including

    Caitlin Prossner Long & Foster Real Estate, Inc.

    1337 Queen Anne Dr, Chester, MD 21619
  • /10

    $539,900 Sold Sep 08, 2025

    121 Wheelhouse Way Unit 11, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 2,003 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $270/SF
    • 40 Days On Market

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

    121 Wheelhouse Way Unit 11, Chester, MD 21619
    • /28

      Est $361,898 Not Listed For Sale

      206 Church St, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,368 Sq Ft
      • Built 1935
      206 Church St, Chester, MD 21619

      Last Sold Summary

      • 3% Below List Price
      • $274/SF
      • 52 Days On Market

      Last Sold Price $375,000

      Last Listing Agent Jim Keating Keller Williams Realty Centre

  • /12

    $519,900 New Construction

    • 1,250 Sq Ft

    0 Harbor Dr, Chester, MD 21619

    House is now substantially constructed. Builder has finished the lower level and included a bathroom! Lots of extra space and upgrades at this new home! Settle in 30-60 days. LVP floors, granite countertops, stainless steel appliances, etc.

    DJ Dauses Coldwell Banker Waterman Realty

    0 Harbor Dr, Chester, MD 21619
  • /53

    $367,500 Sold Mar 26, 2025

    2 A Queen Victoria, Chester, MD 21619

    • 3 Beds
    • 2 Baths
    • 1,763 Sq Ft
    • Built 1984

    Last Sold Summary

    • $208/SF
    • 88 Days On Market

    Last Listing Agent Jackie Ball Daley Northrop Realty

    2 A Queen Victoria, Chester, MD 21619
    • /55

      Est $1,090,973 Not Listed For Sale

      2802 Cox Neck Rd, Chester, MD 21619

      • 4 Beds
      • 3.5 Baths
      • 3,692 Sq Ft
      • Built 1997
      2802 Cox Neck Rd, Chester, MD 21619

      Last Sold Summary

      • 16% Above List Price
      • $255/SF
      • 57 Days On Market

      Last Sold Price $942,000

      Last Listing Agent Biana Arentz Coldwell Banker (NRT-Southeast-MidAtlantic)

  • /7

    $230,000

    • Land
    • 1.68 Acres
    • $136,905 per Acre

    0 Newtown Rd, Chester, MD 21619

    Looking for peace and serenity, look no further! You won't find a better opportunity on the eastern shore, total of just over 1.10 acres (per the tax record)! This acreage is a total of 2 tax ID numbers being sold as a package. Buyer to verify perc, well, engineering, specific lot lines and land survey. Seller will not.

    Rob Carter Douglas Realty, LLC

    0 Newtown Rd, Chester, MD 21619
  • /26

    $679,900 Sold Sep 18, 2025

    121 Wheelhouse Way Unit 32, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2025

    Move in Ready Sold Summary

    • $358/SF
    • 23 Days On Market

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

    121 Wheelhouse Way Unit 32, Chester, MD 21619
    • /45

      Est $618,113 Not Listed For Sale

      2608 Cecil Dr, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 2,336 Sq Ft
      • Built 1976
      2608 Cecil Dr, Chester, MD 21619

      Last Sold Summary

      • 6% Below List Price
      • $280/SF
      • 1 Day On Market

      Last Sold Price $655,000

      Last Listing Agent Violeta Aguirre Long & Foster

  • /52

    $799,990 Pending

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

    176 Flagstaff Way Unit 2433, Chester, MD 21619

    The Chester at Lot 2433 offers a thoughtfully designed open-concept layout with a projected settlement date of August 2026, making it an excellent opportunity for buyers planning ahead. This home features 2 bedrooms, 2.5 baths, and a 1-car garage, delivering comfort, functionality, and efficient use of space. Standout features include a dedicated home office with lighted French doors, a dry bar

    Mary Anne Kowalewski KOVO Realty

    176 Flagstaff Way Unit 2433, Chester, MD 21619
  • /29

    $829,990 Sold Mar 11, 2026

    176 Flagstaff Way Unit 33, Chester, MD 21619

    • 2 Beds
    • 2.5 Baths
    • 1,900 Sq Ft
    • Built 2026

    Move in Ready Sold Summary

    • 5% Below List Price
    • $437/SF
    • 5 Days On Market

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

    176 Flagstaff Way Unit 33, Chester, MD 21619
    • /37

      Est $754,058 Not Listed For Sale

      121 Mcguckin St, Chester, MD 21619

      • 4 Beds
      • 2.5 Baths
      • 2,914 Sq Ft
      • Built 2008
      121 Mcguckin St, Chester, MD 21619

      Last Sold Summary

      • 16% Above List Price
      • $223/SF
      • 125 Days On Market

      Last Sold Price $650,000

      Last Listing Agent Peggy Stancavage Long & Foster

  • /12

    $349,900 Open House 4/04

    • 1 Bed
    • 1 Bath
    • 724 Sq Ft

    34 Queen Anne Way Unit F, Chester, MD 21619

    Rare Opportunity in Queen’s Landing with Stunning Chester River Views Welcome to one of the few oversized one-bedroom condos in the highly desirable Queen’s Landing community. Immaculately maintained and thoughtfully designed, this larger-than-average unit offers gorgeous views of the Chester River and the added benefit of expanded living space rarely found in one-bedroom layouts. The larger

    Joelle Dolch Cross Street Realtors LLC

    34 Queen Anne Way Unit F, Chester, MD 21619
  • /39

    $36,000 Sold Mar 31, 2025

    9D Piney Narrows Rd, Chester, MD 21619

    • 703 Sq Ft
    • Built 1981

    Last Sold Summary

    • $51/SF
    • 3 Days On Market

    Current Estimated Value $35,116

    Last Listing Agent Lisa Lynch Keller Williams Realty

    9D Piney Narrows Rd, Chester, MD 21619
    • /61

      Est $722,698 Not Listed For Sale

      244 Bentons Pleasure Rd, Chester, MD 21619

      • 3 Beds
      • 2 Baths
      • 1,248 Sq Ft
      • Built 1948
      244 Bentons Pleasure Rd, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $561/SF
      • 72 Days On Market

      Last Sold Price $700,000

      Last Listing Agent John McGlannan Meredith Fine Properties

  • /37

    $519,900 Pending

    • 3 Beds
    • 2.5 Baths
    • 2,066 Sq Ft

    112 Chessie Ct, Chester, MD 21619

    Step inside and see this meticulously cared for home!This home features a first floor primary bedroom with an ensuite full bath.Just 5 minutes from the Chesapeake Bay Bridge and all the beaches, parks, boat ramps, and waterfront venues you love to visit...all within a few minutes drive.This single detached home has been thoughtfully improved throughout, with luxury vinyl plank floors,

    Carol Delayo Chaney Homes, LLC

    112 Chessie Ct, Chester, MD 21619
  • /63

    $365,000 Sold Oct 20, 2025

    1033 Dundee Ct Unit 5, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,360 Sq Ft
    • Built 2003

    Last Sold Summary

    • $268/SF
    • 14 Days On Market

    Current Estimated Value $363,605

    Last Listing Agent Erin Anderson Chesapeake Real Estate Associates, LLC

    1033 Dundee Ct Unit 5, Chester, MD 21619
    • /46

      Est $460,071 Not Listed For Sale

      915 Auckland Way, Chester, MD 21619

      • 3 Beds
      • 3.5 Baths
      • 2,100 Sq Ft
      • Built 2001
      915 Auckland Way, Chester, MD 21619

      Last Sold Summary

      • 8% Above List Price
      • $203/SF
      • 67 Days On Market

      Last Sold Price $427,000

      Last Listing Agent Jenn Bonk Cummings & Co. Realtors

  • /2

    $19,500

    • 2 Beds
    • 1 Bath
    • 764 Sq Ft

    1405 Little Creek Rd, Chester, MD 21619

    This property, situated on a 0.17-acre lot, offers a blank canvas for your vision. Located in Queen Anne's County, the existing structure presents endless possibilities for the right buyer. Take advantage of the spacious lot size, perfect for outdoor activities or future expansion plans. Buyers are encouraged to perform their own due diligence to verify property details.Please note that

    Dustin Parker The Parker Group

    1405 Little Creek Rd, Chester, MD 21619
  • /54

    $449,900 Sold May 28, 2025

    122 Dundee Ave, Chester, MD 21619

    • 3 Beds
    • 2.5 Baths
    • 1,706 Sq Ft
    • Built 2013

    Last Sold Summary

    • $264/SF
    • 39 Days On Market

    Current Estimated Value $436,377

    Last Listing Agent Sandy Patterson Taylor Properties

    122 Dundee Ave, Chester, MD 21619
    • /27

      Est $331,525 Not Listed For Sale

      306 Drake Tail Place, Chester, MD 21619

      • 3 Beds
      • 2.5 Baths
      • 1,440 Sq Ft
      • Built 1992
      306 Drake Tail Place, Chester, MD 21619

      Last Sold Summary

      • $229/SF
      • 68 Days On Market

      Last Sold Price $330,000

      Last Listing Agent Melissa Murray Compass

  • /52

    $549,000 Open Sat 10AM - 12PM

    • 2 Beds
    • 2.5 Baths
    • 1,586 Sq Ft

    34 Queen Anne Way, Chester, MD 21619

    Open House Saturday March 28th from 10:00 - 12:00. Fully Remodeled Chester River Waterfront Condo! This gem won't last long! Beautifully renovated 2BR/2.5BA waterfront condominium located in the sought-after Queen’s Landing resort-style community on the scenic Chester River, just off the Chesapeake Bay. This move-in-ready home showcases a stunning top-to-bottom remodel, including new luxury vinyl

    Lona Todd Taylor Properties

    34 Queen Anne Way, Chester, MD 21619
  • /36

    $705,000 Sold Sep 23, 2025

    242 Peregrine Dr, Chester, MD 21619

    • 4 Beds
    • 3 Baths
    • 3,151 Sq Ft
    • Built 2024

    Last Sold Summary

    • $224/SF
    • 111 Days On Market

    Last Listing Agent Pamela Owens Anchor Group Realty, LLC

    242 Peregrine Dr, Chester, MD 21619
    • /19

      Est $278,478 Not Listed For Sale

      413 Merganser Ct, Chester, MD 21619

      • 2 Beds
      • 2 Baths
      • 1,069 Sq Ft
      • Built 1999
      413 Merganser Ct, Chester, MD 21619

      Last Sold Summary

      • 3% Above List Price
      • $253/SF
      • 0 Days On Market

      Last Sold Price $270,000

      Last Listing Agent Cindy Jacobs Maryland Residential Management Co

  • /52

    $799,990 Pending

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

    110 Boatswain Way Unit 3043, Chester, MD 21619

    Welcome to the Chester, a thoughtfully designed home offering 2 bedrooms, 2.5 baths, and a 1-car garage. Scheduled for settlement in October 2026, this home combines modern comfort with functional living spaces. The heart of the home features a dry bar and an electric fireplace, creating a warm and inviting atmosphere. A dedicated home office with lited French doors provides a stylish and private

    Mary Anne Kowalewski KOVO Realty

    110 Boatswain Way Unit 3043, Chester, MD 21619
  • /66

    $1,700,000 Sold Jul 11, 2025

    2921 Cox Neck Rd E, Chester, MD 21619

    • 4 Beds
    • 2.5 Baths
    • 2,824 Sq Ft
    • Built 1992

    Last Sold Summary

    • $602/SF
    • 2 Days On Market

    Current Estimated Value $1,665,002

    Last Listing Agent Lynn Tuozzo Berkshire Hathaway HomeServices PenFed Realty

    2921 Cox Neck Rd E, Chester, MD 21619

Showing Results 121 - 160, Page 4 of 18

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