Chestertown Homes under $250,000

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Newest Chestertown Homes under $250,000

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:

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:

7415 Wilkins Ln, Chestertown $222,000 ▼

This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property f...

3 Beds
1 Baths

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

104 Conley Dr, Chestertown $239,900 ▼

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, lo...

3 Beds
2 Baths

Courtesy of Cummings & Co. Realtors

Listing courtesy of Cummings & Co. Realtors. Contact:

234 N College Ave, Chestertown $79,000 ▼

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the he...

2 Beds
1 Baths

Courtesy of Cummings & Co Realtors

Listing courtesy of Cummings & Co Realtors. Contact:

117 Water St N Unit 1B, Chestertown image

117 Water St N Unit 1B, Chestertown $200,000

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

1 Beds
1 Baths

Courtesy of TTR Sotheby's International Realty

Listing courtesy of TTR Sotheby's International Realty. Contact: