Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings

Save search

Map layers

Safety

Safety & registry resources

Review official public-safety information for any area from these government sources:

  • U.S. Dept. of Justice National Sex Offender Public Website (NSOPW)
  • FBI: state sex-offender registry directory
Chester, MD Homes for Sale — Page 3 | Realty.com
Realty.com
Buy

Start here

  • Homes for sale by state
  • Home buying tips
  • Before you start looking
  • The buying timeline

Afford it

  • Today's mortgage rates
  • Mortgage calculator
  • How much can I afford?
  • Get pre-approved

Make the deal

  • Writing a winning offer
  • Inspections & appraisals
  • Closing costs, itemized
  • Find a buyer's agent
Save searchAdvertiseSign In
Saved homesSaved searchesYour toursYour inquiriesRecently viewedAccount settings
  • Rentals
  • Commercial

70 listings
Sell

Selling Options

  • What's my home worth?
  • Compare selling options
  • Get an instant cash offer
  • Buy before you sell

Resources

  • How selling works
  • When should I sell?
  • Home selling tips
  • Pricing your home
  • What's worth fixing first
  • Find a seller's agent
Home Loans
Find an Agent
Save search

Homes for Sale in Chester, MD

Homes for Sale in Chester, MD

Hide Map
22 of 70 Listings
Map

Homes for Sale in Chester, MD

22 of 70 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 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.

  2. 102 Boatswain Way #2933 — photoPrice Reduced47Active

    $809,990

    2 bd · 3 ba · 1,900 sqft

    102 Boatswain Way #2933, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  3. 134 Richard Ingle Way — photoPrice Reduced63Active

    $739,000

    4 bd · 4 ba · 2,185 sqft

    134 Richard Ingle Way, Chester, MD

    Barbara A McCaffrey · Redfin Corp

  4. 230 Switchgrass Way #12 — photoPrice Reduced23Active

    $499,000

    2 bd · 3 ba · 2,003 sqft

    230 Switchgrass Way #12, Chester, MD

    David J. Moore · Real Broker, LLC - Chester

  5. 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

  6. 300 Woods Point Rd — photoPrice Reduced78Active

    $2,625,000

    3 bd · 2 ba · 2,000 sqft

    300 Woods Point Rd, Chester, MD

    Elinor W Warring · Tidewater Properties

  7. 21-F Queen Victoria Way — photo38Active

    $472,500

    3 bd · 3 ba · 1,620 sqft

    21-F Queen Victoria Way, Chester, MD

    Jennifer Anne Thomas · RE/MAX Executive

  8. 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

  9. 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

  10. 106 Bodys Neck Rd — photoPrice Reduced48Active

    $429,900

    3 bd · 3 ba · 1,595 sqft

    106 Bodys Neck Rd, Chester, MD

    William Warren Longest Jr. · Realty Navigator

  11. 232 Evelyne St — photoPrice Reduced35Active

    $799,900

    4 bd · 4 ba · 3,312 sqft

    232 Evelyne St, Chester, MD

    Courtney Chipouras · TTR Sotheby's International Realty

  12. 129 Wheelhouse Way #11 — photo40Active

    $585,000

    2 bd · 3 ba · 2,003 sqft

    129 Wheelhouse Way #11, Chester, MD

    Jennifer Anne Thomas · RE/MAX Executive

  13. 5011 Bridgepointe Dr — photoPrice Reduced46Active

    $315,000

    3 bd · 3 ba · 1,302 sqft

    5011 Bridgepointe Dr, Chester, MD

    Nickolaus B Waldner · Keller Williams Realty Centre

  14. 45-G Queen Neva Ct — photoPrice Reduced40Active

    $318,500

    2 bd · 3 ba · 1,312 sqft

    45-G Queen Neva Ct, Chester, MD

    John V Freeman · Coldwell Banker Realty

  15. 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.

  16. 2855 Cox Neck Rd — photoPrice Reduced78Active

    $1,125,000

    4 bd · 5 ba · 4,413 sqft

    2855 Cox Neck Rd, Chester, MD

    Tricia Z Wilson · Wilson Realty & Staging LLC

  17. 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

  18. 43-A Queen Neva Ct — photoPrice Reduced71Active

    $445,000

    3 bd · 3 ba · 2,008 sqft

    43-A Queen Neva Ct, Chester, MD

    Ryan Briggs · Anne Arundel Properties, Inc.

  19. 4000 Herons Nest Way #22 — photoPrice Reduced70Active

    $492,500

    2 bd · 3 ba · 1,900 sqft

    4000 Herons Nest Way #22, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  20. 3000 Herons Nest Way #11 — photoPrice Reduced66Active

    $460,000

    2 bd · 3 ba · 2,003 sqft

    3000 Herons Nest Way #11, Chester, MD

    John V Freeman · Coldwell Banker Realty

  21. 1757 Harbor Dr — photo64Active

    $1,198,800

    4 bd · 4 ba · 0 sqft

    1757 Harbor Dr, Chester, MD

    George 112,540 Bailey · Keller Williams Flagship

  22. 1405 Little Creek Rd — photo2Active

    $19,500

    2 bd · 1 ba · 764 sqft

    1405 Little Creek Rd, Chester, MD

    Dustin Parker · The Parker Group

123
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.

© 2026 Realty.com. All rights reserved.·Privacy·Terms·California Privacy Rights·Accessibility·Licensing

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: 2026-10-31 06:00:51 UTC
  • Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

    Nearby areas

    ZIP codes

    • 21223 (312)
    • 21224 (288)
    • 21230 (266)
    • 21217 (217)
    • 21213 (176)
    • 21216 (174)
    • 21222 (136)
    • 21401 (136)

    Cities

    • Baltimore (2,214)
    • Annapolis (305)
    • Glen Burnie (175)
    • Easton (127)
    • Pasadena (120)
    • Stevensville (88)
    • Chestertown (61)
    • Dundalk (61)

    Chester, MD community profile

    Area
    22.5 sq. mi.

    Source: HJN community data

    Chester housing market

    October 2026 · This period is still settling

    Selling at 100.0% of asking price

    Sales here are closing essentially at asking. MLS · 14 sales · as of Oct 30, 2026

    Homes on the market · MLS, as of Oct 25, 2026–Oct 30, 2026

    Median list price
    $545,000
    Homes for sale
    57
    Median days on market
    33 days

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Sep 30, 2026

    Median home size
    1,728 sq. ft.