Multiple farm outbuildings
Chestertown MD Luxury Homes
126 results
- 117 N Water St #1A-1B-2B, Chestertown, MD 21620
- 7 bds
- 5 ba
- 5,400 sqft
TTR SOTHEBY'S INTERNATIONAL REALTYSoaring ceilings
Loading...
- 8796 Maryland Pkwy, Chestertown, MD 21620
- 9 bds
- 7 ba
- 4,776 sqft
COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANYEight fireplaces
- Little Harbor Way #1, Chestertown, MD 21620
- 3 bds
- 3 ba
- 2,231 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATE306 days on Zillow
- 22470 Fairgale Farm Ln, Chestertown, MD 21620
- 4 bds
- 5 ba
- 4,257 sqft
GUNTHER-MCCLARY REAL ESTATEPrice cut: $75,000 (9/10)
- 105 High St, Chestertown, MD 21620
- 5 bds
- 5 ba
- 3,243 sqft
COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANYProminent historic corners
- 302 S Mill St, Chestertown, MD 21620
- 0.46 acres lot
COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANYRadcliffe creek behind
- 25 Landing Ln, Chestertown, MD 21620
- 4 bds
- 4 ba
- 2,784 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATECozy gas fireplace
- 226 S Water St, Chestertown, MD 21620
- 3 bds
- 4 ba
- 2,172 sqft
GUNTHER-MCCLARY REAL ESTATEFilled with natural light
- 7680 Country Club Ln, Chestertown, MD 21620
- 5 bds
- 4 ba
- 2,639 sqft
GUNTHER-MCCLARY REAL ESTATECozy fireplace
Loading...
- 104 Little Harbor Way, Chestertown, MD 21620
- 3 bds
- 3 ba
- 1,980 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATECozy gas fireplace
- 102 Little Harbor Way, Chestertown, MD 21620
- 3 bds
- 3 ba
- 1,964 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATECozy gas fireplace
- 106 S Queen St, Chestertown, MD 21620
- 3 bds
- 4 ba
- 2,472 sqft
CHESAPEAKE REAL ESTATE ASSOCIATES, LLCGenerous private front courtyard
- 8999 Orchard Dr, Chestertown, MD 21620
- 5 bds
- 4 ba
- 4,353 sqft
COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANYFully furnished screening room
- 104 Landing Ln, Chestertown, MD 21620
- 3 bds
- 4 ba
- 2,192 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATELarge walk-in closet
- 106 Landing Ln, Chestertown, MD 21620
- 3 bds
- 4 ba
- 2,092 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATELarge walk-in closet
- 7828 Country Club Ln, Chestertown, MD 21620
- 3 bds
- 3 ba
- 2,857 sqft
CROSS STREET REALTORS LLCSpacious brick rancher
- 35 Landing Ln, Chestertown, MD 21620
- 3 bds
- 3 ba
- 1,964 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATEFlexible living options
- 37 Landing Ln, Chestertown, MD 21620
- 3 bds
- 3 ba
- 1,964 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATELarge walk-in closet
- 36 Landing Ln, Chestertown, MD 21620
- 3 bds
- 3 ba
- 1,964 sqft
Paquin Design Build, GUNTHER-MCCLARY REAL ESTATELarge walk-in closet
- 216 Birch Run Rd, Chestertown, MD 21620
- 3 bds
- 3 ba
- 2,176 sqft
TTR SOTHEBY'S INTERNATIONAL REALTYClassic brick facade
- 201 N Lynchburg St, Chestertown, MD 21620
- 4,342 sqft lot
RE/MAX ASSOCIATES-HOCKESSIN197 days on Zillow
- 117 N Water St #1A, Chestertown, MD 21620
- 3 bds
- 3 ba
- 3,000 sqft
TTR SOTHEBY'S INTERNATIONAL REALTYSoaring ceilings - 212 Washington Ave, Chestertown, MD 21620
- 5 bds
- 3 ba
- 2,838 sqft
COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANYOn Market Oct 03
- 22400 Great Oak Landing Rd, Chestertown, MD 21620
- 4 bds
- 3 ba
- 2,864 sqft
COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANYOpen: Sat 11am-1pm (9/19)
- 108 Little Harbor Way, Chestertown, MD 21620
- 3,711 sqft lot
GUNTHER-MCCLARY REAL ESTATEBuildable waterfront lot
- 329 Union Church Rd, Chestertown, MD 21620
- 4 bds
- 3 ba
- 2,464 sqft
CHESAPEAKE REAL ESTATE ASSOCIATES, LLCOn Market Sep 28
- 103 Sutton Way, Chestertown, MD 21620
- 5 bds
- 4 ba
- 3,816 sqft
TTR SOTHEBY'S INTERNATIONAL REALTYUltimate entertainment zone
- 204 Double Creek Rd, Chestertown, MD 21620
- 3 bds
- 3 ba
- 2,927 sqft
DOUG ASHLEY REALTORS, LLCPrice cut: $20,000 (8/14)
- Open: Sat 11am-1pm (9/12)
- 103 Landing Ln, Chestertown, MD 21620
- 2 bds
- 3 ba
- 2,100 sqft
COLDWELL BANKER CHESAPEAKE REAL ESTATE COMPANYWaterfront walkways and parks
- Extra-wide driveway
- 129 Trafford Dr, Chestertown, MD 21620
- 3 bds
- 3 ba
- 3,176 sqft
ELEVATED REAL ESTATE SOLUTIONSPrivate backyard oasis
- Price cut: $23,000 (9/2)
- 65 days on Zillow
- Half acre lot
- New flooring throughout
- Brick on front siding
- Price cut: $20,100 (8/26)
- 23043 Bay Shore Spur, Chestertown, MD 21620
- 4 bds
- 3 ba
- 2,630 sqft
ROCK HALL PROPERTIES REAL ESTATETwo fireplaces
- Freshly painted
to get email alerts when listings hit the market.
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, and is provided by BRIGHT through a licensing agreement. Listing information is from various brokers who participate in the Bright MLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information 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 the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 Bright MLS, Inc. [Click here for more information](/mls-disclaimers/#5632)
