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3 Bedroom Homes in Chester, MD
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3 Bedroom Homes in Chester, MD

3 Bedroom Homes in Chester, MD

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24 of 31 Listings
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3 Bedroom Homes in Chester, MD

24 of 31 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 107 Lee Rd — photo20Active

    $330,000

    3 bd · 1 ba · 960 sqft

    107 Lee Rd, Chester, MD

    Verria Hairston · Open Door Brokerage, LLC

  2. 830 Warbler Way #2824 — photo51Active

    $749,990

    3 bd · 3 ba · 2,602 sqft

    830 Warbler Way #2824, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  3. 208 Widgeon Way — photo4Active

    $599,900

    3 bd · 4 ba · 2,100 sqft

    208 Widgeon Way, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  4. 117 Wright Rd — photo62Active

    $412,000

    3 bd · 2 ba · 1,337 sqft

    117 Wright Rd, Chester, MD

    Diane Superczynski · Douglas Realty LLC

  5. 114 Kinglet Ct — photo25Active

    $999,990

    3 bd · 3 ba · 2,772 sqft

    114 Kinglet Ct, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  6. 247 Redstart Dr — photo27Active

    $899,990

    3 bd · 3 ba · 2,772 sqft

    247 Redstart Dr, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  7. 510 Auckland Way — photo31Active

    $410,000

    3 bd · 3 ba · 1,899 sqft

    510 Auckland Way, Chester, MD

    Dawn Haskins Smith · Engel & Volkers Annapolis

  8. 320 Bayberry Dr — photo90Active

    $859,900

    3 bd · 2 ba · 2,331 sqft

    320 Bayberry Dr, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  9. 1012 Auckland Way — photo35Active

    $599,900

    3 bd · 4 ba · 2,076 sqft

    1012 Auckland Way, Chester, MD

    Jerrise Spencer · Redfin Corp

  10. 512 Auckland Way — photo51Active

    $375,000

    3 bd · 4 ba · 1,899 sqft

    512 Auckland Way, Chester, MD

    Lawrence Doyle · Long & Foster Real Estate, Inc.

  11. 1010 Auckland Way — photo54Active

    $595,000

    3 bd · 4 ba · 2,100 sqft

    1010 Auckland Way, Chester, MD

    Lori G Woods-Fortney · Berkshire Hathaway HomeServices Homesale Realty

  12. 6005 Bridgepointe Dr — photo54Active

    $349,000

    3 bd · 3 ba · 1,302 sqft

    6005 Bridgepointe Dr, Chester, MD

    Megan E Rosendale · Rosendale Realty

  13. 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

  14. 108 Blenny Ln — photoPrice Reduced37Active

    $369,900

    3 bd · 3 ba · 1,899 sqft

    108 Blenny Ln, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  15. 402 Macum Creek Dr — photo91Active

    $789,000

    3 bd · 3 ba · 2,787 sqft

    402 Macum Creek Dr, Chester, MD

    Tara Trout · Samson Properties

  16. 214 Bayberry Dr — photo68Active

    $924,000

    3 bd · 3 ba · 2,745 sqft

    214 Bayberry Dr, Chester, MD

    James C Corson · Benson & Mangold, LLC

  17. 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

  18. 117 Flycatcher Way — photoPrice Reduced25Active

    $995,990

    3 bd · 4 ba · 2,930 sqft

    117 Flycatcher Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  19. 111 Marshgrass Way #41 — photo56Active

    $998,000

    3 bd · 3 ba · 2,602 sqft

    111 Marshgrass Way #41, Chester, MD

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

  20. 532 Warbler Way — photoPrice Reduced27Active

    $799,990

    3 bd · 3 ba · 2,772 sqft

    532 Warbler Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  21. 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

  22. 300 Woods Point Rd — photo78Active

    $2,840,000

    3 bd · 2 ba · 2,000 sqft

    300 Woods Point Rd, Chester, MD

    Elinor W Warring · Tidewater Properties

  23. 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

  24. 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

12

About 3 Bedroom Homes in Chester, MD

3 Bedroom Homes in Chester, MD: 31 active listings as of October 6, 2026, 23:52 UTC.

Property types among these 31 listings, by the property type each listing’s MLS reports, spelled as the MLS spells it. Types with fewer than 5 listings, and listings whose MLS reports no type, are not shown, so the shares can total less than 100%.
Property typeListingsShare
Single Family Residence1341.9%
Condominium1135.5%
Realty.com

L. Custen Realty, Inc. d/b/a Realty.com/L. Custen Realty CT, LLC d/b/a Realty.com (Tom O’Leary-Broker)(CT properties only), 8323 Southwest Freeway, Suite 900, Houston, Texas 77074

Equal Housing OpportunityEqual Housing Lender

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

Bright MLS
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: 2026-10-05 13:24:38 UTC
  • 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

    September 2026 · This period is still settling

    Chester 12-month median sale price trend

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 15 sales · as of Sep 30, 2026

    Homes that sold · County records, as of Sep 18, 2026

    Median sale price
    $400,000$284,250–$656,750 typical range
    Price per sq. ft.
    $278
    Sales
    14
    Paid in cash
    57.1%

    Homes on the market · MLS, as of Sep 27, 2026–Sep 30, 2026

    Median list price
    $554,500
    Homes for sale
    46
    Median days on market
    21 days

    Price trend · Assessor repeat sales, as of Sep 30, 2026

    Year-over-year
    -23.4%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 2, 2026

    Median home size
    1,728 sq. ft.