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Homes Under $700K in Chester, MD
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33 listings
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3 bedsNew constructionWith a pool

Homes Under $700K in Chester, MD

Homes Under $700K in Chester, MD

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24 of 33 Listings
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Homes Under $700K in Chester, MD

24 of 33 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 641 Warbler Way — photoNew22Active

    $669,990

    2 bd · 2 ba · 1,690 sqft

    641 Warbler Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  2. 1868 Roberta Dr — photoNew48Active

    $400,000

    5 bd · 4 ba · 3,250 sqft

    1868 Roberta Dr, Chester, MD

    Carley R. Cooper · Alex Cooper Auctioneers, Inc.

  3. 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.

  4. 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

  5. 102 Boatswain Way #2911 — photoPrice Reduced56Active

    $619,990

    2 bd · 3 ba · 2,003 sqft

    102 Boatswain Way #2911, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  6. 2004 Bridgepointe Dr — photoPrice Reduced32Active

    $374,900

    3 bd · 2 ba · 1,524 sqft

    2004 Bridgepointe Dr, Chester, MD

    Sheryl Marie Carmody · RE/MAX Executive

  7. 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

  8. 230 Switchgrass Way #12 — photoPrice Reduced23Active

    $525,000

    2 bd · 3 ba · 2,003 sqft

    230 Switchgrass Way #12, Chester, MD

    David J. Moore · Real Broker, LLC - Chester

  9. 205 Anchor Ln — photoPrice Reduced48Active

    $525,000

    5 bd · 3 ba · 3,000 sqft

    205 Anchor Ln, Chester, MD

    Kathleen Higginbotham · Samson Properties

  10. 315 Bentons Pleasure Rd — photo63Active

    $629,900

    3 bd · 2 ba · 1,688 sqft

    315 Bentons Pleasure Rd, Chester, MD

    Douglas G Kayhoe · Douglas Realty LLC

  11. 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

  12. 1000 Herons Nest Way #43 — photoPrice Reduced50Active

    $595,000

    2 bd · 3 ba · 1,832 sqft

    1000 Herons Nest Way #43, Chester, MD

    Dee Dee R McCracken · Coldwell Banker Realty

  13. 6010 Bridgepointe Dr — photoPrice Reduced55Active

    $374,900

    3 bd · 2 ba · 1,885 sqft

    6010 Bridgepointe Dr, Chester, MD

    April L Heim · Rosendale Realty

  14. 2000 Herons Nest Way #401 — photoPrice Reduced36Active

    $700,000

    3 bd · 3 ba · 2,602 sqft

    2000 Herons Nest Way #401, Chester, MD

    Matthew Thomas Arnold · Real Broker, LLC

  15. 1012 Auckland Way — photo46Active

    $599,900

    3 bd · 4 ba · 2,076 sqft

    1012 Auckland Way, Chester, MD

    Jerrise Spencer · Redfin Corp

  16. 807 Auckland Way — photo48Active

    $425,500

    3 bd · 4 ba · 2,100 sqft

    807 Auckland Way, Chester, MD

    David J. Moore · Real Broker, LLC - Chester

  17. 106 Bodys Neck Rd — photo48Active

    $435,000

    3 bd · 3 ba · 1,595 sqft

    106 Bodys Neck Rd, Chester, MD

    William Warren Longest Jr. · Realty Navigator

  18. 132 Wheelhouse Way #11 — photoPrice Reduced29Active

    $699,000

    2 bd · 3 ba · 2,003 sqft

    132 Wheelhouse Way #11, Chester, MD

    Matthew Thomas Arnold · Real Broker, LLC

  19. 6005 Bridgepointe Dr — photoPrice Reduced38Active

    $349,000

    3 bd · 3 ba · 1,302 sqft

    6005 Bridgepointe Dr, Chester, MD

    Megan E Rosendale · Rosendale Realty

  20. 5011 Bridgepointe Dr — photoPrice Reduced46Active

    $354,900

    3 bd · 3 ba · 1,302 sqft

    5011 Bridgepointe Dr, Chester, MD

    Nickolaus B Waldner · Keller Williams Realty Centre

  21. 45-G Queen Neva Ct — photo40Active

    $349,500

    2 bd · 3 ba · 1,312 sqft

    45-G Queen Neva Ct, Chester, MD

    John V Freeman · Coldwell Banker Realty

  22. 54-D Queen Caroline Ct — photoPrice Reduced38Active

    $309,900

    3 bd · 3 ba · 1,440 sqft

    54-D Queen Caroline Ct, Chester, MD

    Michelle DiDonato · Island Realty, LLC

  23. 54F Queen Caroline Ct — photoPrice Reduced46Active

    $349,900

    3 bd · 3 ba · 1,440 sqft

    54F Queen Caroline Ct, Chester, MD

    Lawrence Doyle · Long & Foster Real Estate, Inc.

  24. 126 Watermans Cove Ln — photoPrice Reduced44Active

    $559,000

    3 bd · 3 ba · 1,536 sqft

    126 Watermans Cove Ln, Chester, MD

    Biana Arentz · Coldwell Banker Realty

12

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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 information ©2026 BRIGHT MLS®. All Rights Reserved, Information deemed reliable but not guaranteed. Data Last Updated: 2026-09-02 19:02:30 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 · This period is still settling

    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 14, 2026

    Median sale price
    $567,500$387,500–$843,750 typical range
    Price per sq. ft.
    $317
    Sales
    11
    Paid in cash
    54.6%

    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.