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3 Bedroom Homes in Chester, MD
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27 listings
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3 bedsNew constructionWith a pool

3 Bedroom Homes in Chester, MD

3 Bedroom Homes in Chester, MD

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24 of 27 Listings
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3 Bedroom Homes in Chester, MD

24 of 27 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 275 Warbler Way — photo58Active

    $944,900

    3 bd · 3 ba · 2,761 sqft

    275 Warbler Way, Chester, MD

    Justin Kennedy · Samson Properties

  2. 41-D Queen Catherine Ct — photo50Active

    $439,000

    3 bd · 4 ba · 1,750 sqft

    41-D Queen Catherine Ct, Chester, MD

    Jackie B Daley · Northrop Realty

  3. 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

  4. 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

  5. 214 Bayberry Dr — photo68Active

    $924,000

    3 bd · 3 ba · 2,745 sqft

    214 Bayberry Dr, Chester, MD

    James C Corson · Benson & Mangold, LLC

  6. 201 Switchgrass Way #34 — photo35Active

    $859,500

    3 bd · 3 ba · 2,602 sqft

    201 Switchgrass Way #34, Chester, MD

    Bradley R Kappel · TTR Sotheby's International Realty

  7. 117 Flycatcher Way — photo25Active

    $1,200,000

    3 bd · 4 ba · 2,930 sqft

    117 Flycatcher Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  8. 123 Flycatcher Way — photo26Active

    $1,100,000

    3 bd · 3 ba · 2,789 sqft

    123 Flycatcher Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  9. 148 Elinor St — photo66Active

    $899,000

    3 bd · 3 ba · 2,464 sqft

    148 Elinor St, Chester, MD

    Tara Trout · Samson Properties

  10. 320 Bayberry Dr — photo79Active

    $897,750

    3 bd · 2 ba · 2,331 sqft

    320 Bayberry Dr, Chester, MD

    Jeremy Michael McDonough · Mr. Lister Realty

  11. 111 Marshgrass Way #41 — photo56Active

    $998,000

    3 bd · 3 ba · 0 sqft

    111 Marshgrass Way #41, Chester, MD

    Margaret W Moran · Long & Foster Real Estate, Inc.

  12. 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

  13. 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

  14. 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

  15. 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

  16. 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

  17. 6010 Bridgepointe Dr — photoPrice Reduced55Active

    $374,900

    3 bd · 2 ba · 1,885 sqft

    6010 Bridgepointe Dr, Chester, MD

    April L Heim · Rosendale Realty

  18. 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

  19. 1012 Auckland Way — photo46Active

    $599,900

    3 bd · 4 ba · 2,076 sqft

    1012 Auckland Way, Chester, MD

    Jerrise Spencer · Redfin Corp

  20. 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

  21. 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

  22. 6005 Bridgepointe Dr — photoPrice Reduced38Active

    $349,000

    3 bd · 3 ba · 1,302 sqft

    6005 Bridgepointe Dr, Chester, MD

    Megan E Rosendale · Rosendale Realty

  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. 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

12

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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: 2026-09-03 19:59:18 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.