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Single-Family Homes in Chester, MD
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3 beds
26 listings
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New construction
With a pool

Single-Family Homes in Chester, MD

Single-Family Homes in Chester, MD

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24 of 26 Listings
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Single-Family Homes in Chester, MD

24 of 26 Listings

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TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 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

  2. 200 Church St — photo28Active

    $350,000

    2 bd · 2 ba · 1,274 sqft

    200 Church St, Chester, MD

    Darlene L Winegardner · RE/MAX Executive

  3. 275 Warbler Way — photoPrice Reduced58Active

    $930,000

    3 bd · 3 ba · 2,761 sqft

    275 Warbler Way, Chester, MD

    Justin Kennedy · Samson Properties

  4. 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.

  5. 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

  6. 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

  7. 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.

  8. 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

  9. 402 Macum Creek Dr — photo91Active

    $789,000

    3 bd · 3 ba · 2,787 sqft

    402 Macum Creek Dr, Chester, MD

    Tara Trout · Samson Properties

  10. 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

  11. 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

  12. 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.

  13. 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

  14. 121 Merlin Dr — photoPrice Reduced84Active

    $697,900

    2 bd · 2 ba · 2,118 sqft

    121 Merlin Dr, Chester, MD

    Yael E Beckman · Coldwell Banker Realty

  15. 134 Richard Ingle Way — photo63Active

    $749,000

    4 bd · 4 ba · 2,185 sqft

    134 Richard Ingle Way, Chester, MD

    Barbara A McCaffrey · Redfin Corp

  16. 205 Anchor Ln — photoPrice Reduced49Active

    $515,000

    5 bd · 3 ba · 3,000 sqft

    205 Anchor Ln, Chester, MD

    Kathleen Higginbotham · Samson Properties

  17. 315 Bentons Pleasure Rd — photoPrice Reduced63Active

    $599,900

    3 bd · 2 ba · 1,688 sqft

    315 Bentons Pleasure Rd, Chester, MD

    Douglas G Kayhoe · Douglas Realty LLC

  18. 233 Peregrine Dr — photoPrice Reduced63Active

    $724,999

    4 bd · 3 ba · 3,151 sqft

    233 Peregrine Dr, Chester, MD

    Michelle W Abplanalp · Rosendale Realty

  19. 300 Woods Point Rd — photo78Active

    $2,840,000

    5 bd · 4 ba · 1,704 sqft

    300 Woods Point Rd, Chester, MD

    Elinor W Warring · Tidewater Properties

  20. 205 Riverside Dr — photoPrice Reduced39Active

    $699,000

    3 bd · 2 ba · 1,524 sqft

    205 Riverside Dr, Chester, MD

    Melissa A Chick · Engel & Volkers Annapolis

  21. 232 Evelyne St — photoPrice Reduced35Active

    $825,000

    4 bd · 4 ba · 3,312 sqft

    232 Evelyne St, Chester, MD

    Courtney Chipouras · TTR Sotheby's International Realty

  22. 126 Watermans Cove Ln — photoPrice Reduced44Active

    $559,000

    3 bd · 3 ba · 1,536 sqft

    126 Watermans Cove Ln, Chester, MD

    Biana J Arentz · Coldwell Banker Realty

  23. 2855 Cox Neck Rd — photoPrice Reduced78Active

    $1,195,000

    4 bd · 5 ba · 4,413 sqft

    2855 Cox Neck Rd, Chester, MD

    Tricia Z Wilson · Wilson Realty & Staging LLC

  24. 215 Kingfisher Ln — photoPrice Reduced44Active

    $995,000

    5 bd · 5 ba · 3,225 sqft

    215 Kingfisher Ln, Chester, MD

    Jennifer Anne Thomas · RE/MAX Executive

12

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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.