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

Registered offenders on the map

Save search

Registered offenders on the map

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
3 Bedroom Homes in Chester, MD
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

Registered offenders on the map

25 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
3 bedsNew constructionWith a pool

3 Bedroom Homes in Chester, MD

3 Bedroom Homes in Chester, MD

Show Map
24 of 25 Listings
Map

3 Bedroom Homes in Chester, MD

24 of 25 Listings

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 320 Bayberry Dr — photo62Active

    $859,900

    3 bd · 2 ba · 2,331 sqft

    320 Bayberry Dr, Chester, MD

    Carol L Tinnin · RE/MAX Leading Edge

  2. 1012 Auckland Way — photo34Active

    $599,900

    3 bd · 4 ba · 2,076 sqft

    1012 Auckland Way, Chester, MD

    Jerrise Spencer · Redfin Corp

  3. 6005 Bridgepointe Dr — photo54Active

    $349,000

    3 bd · 3 ba · 1,302 sqft

    6005 Bridgepointe Dr, Chester, MD

    Megan E Rosendale · Rosendale Realty

  4. 275 Warbler Way — photoPrice Reduced58Active

    $930,000

    3 bd · 3 ba · 2,761 sqft

    275 Warbler Way, Chester, MD

    Justin Kennedy · Samson Properties

  5. 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

  6. 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

  7. 207 Thomas White Blvd — photo96Active

    $819,900

    3 bd · 3 ba · 2,479 sqft

    207 Thomas White Blvd, Chester, MD

    Tim Karns · RE/MAX Components

  8. 402 Macum Creek Dr — photo91Active

    $789,000

    3 bd · 3 ba · 2,787 sqft

    402 Macum Creek Dr, Chester, MD

    Tara Trout · Samson Properties

  9. 214 Bayberry Dr — photo68Active

    $924,000

    3 bd · 3 ba · 2,745 sqft

    214 Bayberry Dr, Chester, MD

    James C Corson · Benson & Mangold, LLC

  10. 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

  11. 117 Flycatcher Way — photoPrice Reduced25Active

    $1,100,000

    3 bd · 4 ba · 2,930 sqft

    117 Flycatcher Way, Chester, MD

    David M Willman · Berkshire Hathaway HomeServices PenFed Realty - OP

  12. 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.

  13. 2004 Bridgepointe Dr — photoPrice Reduced32Active

    $369,900

    3 bd · 2 ba · 1,524 sqft

    2004 Bridgepointe Dr, Chester, MD

    Sheryl Marie Carmody · RE/MAX Executive

  14. 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

  15. 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

  16. 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

  17. 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

  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. 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

  20. 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

  21. 54-D Queen Caroline Ct — photoPrice Reduced38Active

    $299,900

    3 bd · 3 ba · 1,440 sqft

    54-D Queen Caroline Ct, Chester, MD

    Michelle DiDonato · Island Realty, LLC

  22. 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.

  23. 126 Watermans Cove Ln — photoPrice Reduced44Active

    $559,000

    3 bd · 3 ba · 1,536 sqft

    126 Watermans Cove Ln, Chester, MD

    Biana J Arentz · Coldwell Banker Realty

  24. 43-A Queen Neva Ct — photo72Active

    $459,000

    3 bd · 3 ba · 2,008 sqft

    43-A Queen Neva Ct, Chester, MD

    Ryan Briggs · Anne Arundel Properties, Inc.

12

Explore Chester homes

By price

  • Under $300K
  • Under $500K
  • Under $700K
  • Luxury

By bedrooms

  • 2 beds
  • 3 beds
  • 4 beds
  • 5 beds

By type

  • Single family
  • Townhomes
  • Condos
  • Manufactured homes
  • Multi-family homes
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: 2026-09-20 22:34:00 UTC
  • Co-ops
  • By feature

    • 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

    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 28, 2026

    Median sale price
    $567,500$359,000–$932,500 typical range
    Price per sq. ft.
    $290
    Sales
    19
    Paid in cash
    57.9%

    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.