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Chester, MD Homes for Sale — Page 2 | Realty.com
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3 beds
65 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 65 Listings
Map

Homes for Sale in Chester, MD

24 of 65 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 715 Warbler Way — photoPrice Reduced25Active

    $779,990

    4 bd · 3 ba · 2,791 sqft

    715 Warbler Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  2. 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

  3. 102 Boatswain Way #2933 — photoPrice Reduced47Active

    $819,990

    2 bd · 3 ba · 1,900 sqft

    102 Boatswain Way #2933, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  4. 532 Warbler Way — photoPrice Reduced27Active

    $899,990

    3 bd · 3 ba · 2,772 sqft

    532 Warbler Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  5. 110 Boatswain Way #3042 — photoPrice Reduced47Active

    $719,990

    2 bd · 3 ba · 1,900 sqft

    110 Boatswain Way #3042, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  6. 540 Warbler Way — photoPrice Reduced27Active

    $929,990

    3 bd · 3 ba · 2,789 sqft

    540 Warbler Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  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. 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

  9. 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

  10. 205 Anchor Ln — photoPrice Reduced48Active

    $525,000

    5 bd · 3 ba · 3,000 sqft

    205 Anchor Ln, Chester, MD

    Kathleen Higginbotham · Samson Properties

  11. 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

  12. 233 Peregrine Dr — photoPrice Reduced63Active

    $724,999

    4 bd · 3 ba · 3,151 sqft

    233 Peregrine Dr, Chester, MD

    Michelle W Abplanalp · Rosendale Realty

  13. 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

  14. 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

  15. 6010 Bridgepointe Dr — photoPrice Reduced54Active

    $374,900

    3 bd · 2 ba · 1,885 sqft

    6010 Bridgepointe Dr, Chester, MD

    April L Heim · Rosendale Realty

  16. 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

  17. 1012 Auckland Way — photo46Active

    $599,900

    3 bd · 4 ba · 2,076 sqft

    1012 Auckland Way, Chester, MD

    Jerrise Spencer · Redfin Corp

  18. 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

  19. 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

  20. 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

  21. 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

  22. 2702 Sherman Dr — photo65Active

    $989,000

    5 bd · 4 ba · 2,752 sqft

    2702 Sherman Dr, Chester, MD

    Justin Kennedy · Samson Properties

  23. 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

  24. 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

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: 2026-09-07 17:11:44 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 · 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 19, 2026

    Median sale price
    $567,500$356,500–$843,750 typical range
    Price per sq. ft.
    $313
    Sales
    15
    Paid in cash
    60.0%

    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 (276)
    • 21224 (255)
    • 21230 (222)
    • 21213 (214)
    • 21217 (200)
    • 21216 (172)
    • 21218 (138)
    • 21222 (136)

    Cities

    • Baltimore (2,251)
    • Annapolis (265)
    • Glen Burnie (155)
    • Pasadena (122)
    • Easton (105)
    • Stevensville (86)
    • Chestertown (62)
    • Millersville (54)