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Chester, MD Homes for Sale | Realty.com
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3 beds
61 listings
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New construction
With a pool

Homes for Sale in Chester, MD

Homes for Sale in Chester, MD

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24 of 61 Listings
Map

Homes for Sale in Chester, MD

24 of 61 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 1012 Auckland Way — photoNew34Active

    $599,900

    3 bd · 4 ba · 2,076 sqft

    1012 Auckland Way, Chester, MD

    Jerrise Spencer · Redfin Corp

  2. 53-E Queen Caroline Ct — photo38Active

    $329,000

    2 bd · 3 ba · 1,440 sqft

    53-E Queen Caroline Ct, Chester, MD

    Tammy Studebaker · EXP Realty, LLC

  3. 6005 Bridgepointe Dr — photo54Active

    $349,000

    3 bd · 3 ba · 1,302 sqft

    6005 Bridgepointe Dr, Chester, MD

    Megan E Rosendale · Rosendale Realty

  4. 47-F Queen Anne Way — photo52Active

    $550,000

    2 bd · 3 ba · 1,616 sqft

    47-F Queen Anne Way, Chester, MD

    Debra P Noone · Northrop Realty

  5. 641 Warbler Way — photoPrice Reduced23Active

    $639,990

    2 bd · 2 ba · 1,690 sqft

    641 Warbler Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  6. 200 Church St — photo28Active

    $350,000

    2 bd · 2 ba · 1,274 sqft

    200 Church St, Chester, MD

    Darlene L Winegardner · RE/MAX Executive

  7. 275 Warbler Way — photoPrice Reduced58Active

    $930,000

    3 bd · 3 ba · 2,761 sqft

    275 Warbler Way, Chester, MD

    Justin Kennedy · Samson Properties

  8. 1868 Roberta Dr — photo48Active

    $400,000

    5 bd · 4 ba · 3,250 sqft

    1868 Roberta Dr, Chester, MD

    Carley R. Cooper · Alex Cooper Auctioneers, Inc.

  9. 326 Castle Marina Rd — photo83Active

    $550,000

    5 bd · 4 ba · 3,552 sqft

    326 Castle Marina Rd, Chester, MD

    Virginia Elizabeth Dauses · Coldwell Banker Waterman Realty

  10. 1717 Harbor Dr — photo77Active

    $1,250,000

    3 bd · 3 ba · 2,742 sqft

    1717 Harbor Dr, Chester, MD

    Samantha A Grimes · Chesapeake Real Estate Associates, LLC

  11. 736 Warbler Way #2733 — photo47Active

    $719,990

    2 bd · 3 ba · 1,900 sqft

    736 Warbler Way #2733, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  12. 233 Cross Creek Ct — photo46Active

    $569,900

    4 bd · 3 ba · 2,332 sqft

    233 Cross Creek Ct, Chester, MD

    Christopher B Nagel · Rory S. Coakley Realty, Inc.

  13. 536 Warbler Way — photoPrice Reduced26Active

    $749,990

    2 bd · 3 ba · 2,010 sqft

    536 Warbler Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  14. 108 Blenny Ln — photo26Active

    $389,900

    3 bd · 3 ba · 1,899 sqft

    108 Blenny Ln, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  15. 207 Thomas White Blvd — photo82Active

    $819,900

    3 bd · 3 ba · 2,479 sqft

    207 Thomas White Blvd, Chester, MD

    Tim Karns · RE/MAX Components

  16. 402 Macum Creek Dr — photo91Active

    $789,000

    3 bd · 3 ba · 2,787 sqft

    402 Macum Creek Dr, Chester, MD

    Tara Trout · Samson Properties

  17. 214 Bayberry Dr — photo68Active

    $924,000

    3 bd · 3 ba · 2,745 sqft

    214 Bayberry Dr, Chester, MD

    James C Corson · Benson & Mangold, LLC

  18. 201 Switchgrass Way #34 — photoPrice Reduced41Active

    $835,000

    3 bd · 3 ba · 2,602 sqft

    201 Switchgrass Way #34, Chester, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  19. 117 Flycatcher Way — photoPrice Reduced25Active

    $1,100,000

    3 bd · 4 ba · 2,930 sqft

    117 Flycatcher Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  20. 148 Elinor St — photo66Active

    $899,000

    3 bd · 3 ba · 2,464 sqft

    148 Elinor St, Chester, MD

    Tara Trout · Samson Properties

  21. 313 Thomas White Blvd — photoPrice Reduced39Active

    $799,900

    4 bd · 3 ba · 3,291 sqft

    313 Thomas White Blvd, Chester, MD

    Carol Snyder · Monument Sotheby's International Realty

  22. 209 Harrier Way — photo123Active

    $747,900

    4 bd · 3 ba · 3,142 sqft

    209 Harrier Way, Chester, MD

    Violeta I Aguirre · Long & Foster Real Estate, Inc.

  23. 113 Bentons Pleasure Rd — photo53Active

    $868,000

    4 bd · 3 ba · 3,168 sqft

    113 Bentons Pleasure Rd, Chester, MD

    Temple H Peirce Jr. · Cummings & Co. Realtors

  24. 102 Boatswain Way #2932 — photoPrice Reduced47Active

    $819,990

    2 bd · 3 ba · 1,900 sqft

    102 Boatswain Way #2932, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

123

Explore Chester homes

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The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Listing data is derived from various Multiple Listing Services; each source MLS and its required disclaimer are shown with the listings on the applicable page. Realty.com is an independently owned and operated brokerage.

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Listing data & MLS disclosures

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Realty.com participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale.
Listing information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-18 09:40:44 UTC
    • New construction
    • With a pool

    Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Chester, MD community profile

    Area
    22.5 sq. mi.

    Source: HJN community data

    Chester housing market

    August 2026

    Chester 12-month median sale price trend

    Selling at 99.4% of asking price

    Buyers here are paying below asking. MLS · 15 sales · as of Aug 26, 2026

    Homes that sold · County records, as of Aug 28, 2026

    Median sale price
    $567,500$359,000–$932,500 typical range
    Price per sq. ft.
    $290
    Sales
    19
    Paid in cash
    57.9%

    Homes on the market · MLS, as of Aug 26, 2026–Aug 31, 2026

    Median list price
    $564,450
    Homes for sale
    46
    Median days on market
    17 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    -8.8%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,728 sq. ft.

    Nearby areas

    ZIP codes

    • 21223 (292)
    • 21224 (266)
    • 21230 (236)
    • 21213 (216)
    • 21217 (202)
    • 21218 (179)
    • 21216 (173)
    • 21122 (139)

    Cities

    • Baltimore (2,400)
    • Annapolis (280)
    • Glen Burnie (159)
    • Pasadena (139)
    • Easton (119)
    • Stevensville (90)
    • Chestertown (63)
    • Dundalk (53)