22$200,000
4 bd · 1 ba · 1,816 sqft
223 Mount Vernon Ave, Chestertown, MD
Maryn J. LeClair · Chesapeake Real Estate Associates, LLC
Homes Under $300K in Chestertown, MD
Hide MapHomes Under $300K in Chestertown, MD
14 Listings
22$200,000
4 bd · 1 ba · 1,816 sqft
223 Mount Vernon Ave, Chestertown, MD
Maryn J. LeClair · Chesapeake Real Estate Associates, LLC
24$289,000
3 bd · 2 ba · 1,056 sqft
8732 Elm Rd, Chestertown, MD
Tracy A Stone · Coldwell Banker Chesapeake Real Estate Company
23$229,000
3 bd · 1 ba · 936 sqft
7415 Wilkins Ln, Chestertown, MD
Retha J Arrabal · Doug Ashley Realtors, LLC
Price Reduced30$295,000
3 bd · 1 ba · 960 sqft
104 Lincoln Dr, Chestertown, MD
Crystal M Smith · RE/MAX Executive
34$263,000
3 bd · 2 ba · 1,140 sqft
115 Chester Arms Dr, Chestertown, MD
Jarnell Preston Foster · Samson Properties
23$299,900
3 bd · 1 ba · 1,056 sqft
124 Wilton Rd, Chestertown, MD
Elizabeth Middleton Green · Doug Ashley Realtors, LLC
Price Reduced21$269,000
3 bd · 2 ba · 1,404 sqft
10540 Tonopah Rd, Chestertown, MD
Michele A Palmer · Doug Ashley Realtors, LLC
10$259,900
3 bd · 2 ba · 1,280 sqft
115 Metcalf Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
10$264,900
3 bd · 2 ba · 0 sqft
121 Metcalf Rd, Chestertown, MD
David J. Moore · Real Broker, LLC - Chester
Price Reduced3$85,000
2 bd · 1 ba · 1,296 sqft
234 N College Ave, Chestertown, MD
Anastasia Marie Zivkovic Palmer · Cummings & Co Realtors
Price Reduced26$239,900
3 bd · 2 ba · 1,280 sqft
104 Conley Dr, Chestertown, MD
Heather Kooser · Cummings & Co. Realtors
Price Reduced26$275,000
3 bd · 3 ba · 1,900 sqft
104 Acorn Dr, Chestertown, MD
Sarah E. King · Cross Street Realtors LLC
Price Reduced29$275,000
3 bd · 1 ba · 1,248 sqft
956 Washington Ave, Chestertown, MD
Grace M Crockett · Doug Ashley Realtors, LLC
20$200,000
1 bd · 1 ba · 700 sqft
117 Water St N #1B, Chestertown, MD
Liddy Campbell · TTR Sotheby's International Realty
Bright MLSSource: HJN community data
August 2026 · This period is still settling
Selling at 100.0% of asking price
Sales here are closing essentially at asking. MLS · 15 sales · as of Aug 27, 2026