Chestertown Homes under $500,000

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Newest Chestertown Homes under $500,000

111 Kent St S, Chestertown $450,000

Nestled in the heart of the Chestertown Historic District, this exquisite residence offers a harmonious blend of traditional charm and modern luxury. Built in 2008, this ...

2 Beds
3 Baths

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

403 Calvert St, Chestertown $135,000

INVESTOR OPPORTUNITY! Come see this 3-bedroom, 1.5-bath townhome offering great potential to add to your portfolio! Recent improvements include drywall replacement, newly...

3 Beds
2 Baths

Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

201 Garland Way, Chestertown $375,000

Discover a prime investment opportunity in the sought-after Coventry Farms subdivision! This charming Colonial-style home, built in 2010, boasts 2,886 square feet of pote...

4 Beds
3 Baths

Courtesy of ERA Martin Associates

Listing courtesy of ERA Martin Associates. Contact:

317 Rolling Rd, Chestertown $229,900

Located in the College Heights neighborhood of Chestertown, this 3-bedroom, 2-bath home is situated on a .34± acre lot and is full of potential! Enjoy the convenience of ...

3 Beds
2 Baths

Courtesy of Select Land & Homes, LLC

Listing courtesy of Select Land & Homes, LLC. Contact:

7545 Quaker Neck Rd, Chestertown $175,000

Needs work. Sold as is

3 Beds
1 Baths

Courtesy of Thurston Wyatt Real Estate, LLC

Listing courtesy of Thurston Wyatt Real Estate, LLC. Contact:

501 High St, Chestertown $349,900

Investor Alert in Historic Downtown Chestertown! Fully Occupied Triplex. Units offer hardwood floors, mini splits to units 1 and 2, a new bathroom in unit 3 and kitchen u...

Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

8668 Elm Rd, Chestertown $349,900

Brand new construction in water oriented Tolchester Estates located on the Chesapeake Bay. 4 Bedroom, 2 bath Cape Cod on a wooded lot and quiet neighborhood. Community o...

4 Beds
2 Baths

Courtesy of Kevin Dey Realty

Listing courtesy of Kevin Dey Realty. Contact:

24607 Chestertown Rd, Chestertown $365,000

Enjoy the best of both worlds with this well-maintained home situated on a generous 0.653-acre lot just outside of Chestertown! Offering the space and privacy of country ...

3 Beds
3 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

21338 Virginia Ave, Chestertown $400,000

Nestled in the quiet Tolchester Estates, this charming new construction home, completed in 2026, embodies the pinnacle of low maintenance living. This well-built ranch-st...

2 Beds
2 Baths

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

106 Harlan Loop, Chestertown $425,000

Nestled in Coventry Farms II, this exquisite Colonial-style residence offers a harmonious blend of Space, Convenience and comfort, perfect for those who appreciate the fi...

4 Beds
3 Baths

Courtesy of Douglas Realty LLC

Listing courtesy of Douglas Realty LLC. Contact:

8820 Cumberland St, Chestertown $281,500 ▼

Discover relaxed Eastern Shore living at 8820 Cumberland Street, a charming three-bedroom, two-full-bath home offering the ease and convenience of single-level living in ...

3 Beds
2 Baths

Courtesy of RE/MAX Advantage Realty

Listing courtesy of RE/MAX Advantage Realty. Contact:

103 Metcalf Rd, Chestertown $259,900

Ask about our SELLER-PAID RATE BUYDOWN — the builder is paying to permanently lower your interest rate when you finance with our preferred lender, who is also contributin...

3 Beds
3 Baths

Courtesy of Real Broker, LLC - Chester

Listing courtesy of Real Broker, LLC - Chester. Contact: