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 Chestertown, 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

1 listing
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 Chestertown, MD

3 Bedroom Homes in Chestertown, MD

Hide Map
1 Listing
Map

3 Bedroom Homes in Chestertown, MD

1 Listing

Your local brokerage

TO

Thomas O'Leary

Realty.com

Lic. #01-6355

Call Thomas
  1. 117 Water St N #1a — photo46Active

    $685,000

    3 bd · 3 ba · 3,000 sqft

    117 Water St N #1a, Chestertown, MD

    Liddy Campbell · TTR Sotheby's International Realty

  2. Your local brokerage

    TO

    Thomas O'Leary

    Realty.com

    Lic. #01-6355

    Call Thomas

Explore Chestertown 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
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

  • Multi-family homes
  • Co-ops
  • By feature

    • New construction
    • With a pool

    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: 2026-09-15 19:52:16 UTC

    Chestertown, MD community profile

    Population
    5,632
    Median income
    $48,766
    Housing units
    2,458
    People per sq. mi.
    42.6
    Area
    132.2 sq. mi.

    Source: HJN community data

    Chestertown housing market

    August 2026 · This period is still settling

    Chestertown 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 Aug 27, 2026

    Homes that sold · County records, as of Aug 28, 2026

    Median sale price
    $321,000$192,500–$573,750 typical range
    Price per sq. ft.
    $181
    Sales
    16
    Paid in cash
    25.0%

    Homes on the market · MLS, as of Aug 27, 2026–Aug 31, 2026

    Median list price
    $478,000
    Homes for sale
    59
    Median days on market
    17 days

    Price trend · Assessor repeat sales, as of Aug 31, 2026

    Year-over-year
    3.6%

    Housing stock — every home in the area, not only the ones selling or listed · Assessor records, as of Jul 29, 2026

    Median home size
    1,735 sq. ft.