Chestertown Real Estate - One Easy MLS Search

If you enjoy history and beautiful water views in a country setting this is your kind of town. Chestertown is quiet College town, home of Washington College a Liberal Arts school founded in 1782. Chestertown offers many fun things to do during throughout year with your family. Historic Chestertown, MD During the warmer months, there is a farmers market down town every saturday from 8-12pm. The farmers market offers lots of fresh produce, plants, flowers, and hand crafted works of local artisans. Every year on Memorial day weekend they have their annual Tea Party parade and festival that always brings out a great crowd.

Newest Property Listings In Chestertown

10181 3rd Point Rd, Chestertown $399,900

Fabulous house in Great Oak Waterfront Community, only 15 minutes from downtown Chestertown! Marina, restaurant, sandy beaches, lots of fishing, 9-hole golf course, and l...

3 Beds
2 Baths
MDKE2001310 MLS

208 Leeds Ct, Chestertown $420,000

A rare find in Coventry Farms, roomy cape cod with the additional detached two car garage. Perched upon a hill on a picturesque tree line street in Coventry Farms I, this...

4 Beds
3 Baths
MDKE2001428 MLS

Langford Rd, Chestertown $50,000

Chestertown - Nice building lot on 1.534 Acres, public record reflects Airy Hill-Brices Road, the property is now known on Langford Road. This is a buildable lot ready ...

MDKE2001462 MLS

116 N Queen St, Chestertown $550,000

Don't miss this special location on Queen Street with 3 off street parking spaces and a rear bonus room that could easily be converted to a first floor master suite! A m...

3 Beds
3 Baths
MDKE2001402 MLS

310 Central Dr, Chestertown $237,500

Simply charming cottage in the water privileged community of Chester Harbor. The interior has been freshly painted and there are new floors through out. New built in micr...

3 Beds
1 Baths
MDQA2003582 MLS

106 Queen St S, Chestertown $695,000

In c1750 this iconic property was known as Bedingfield Hands House and has enjoyed a storied life with many prominent Chestertown residents. Today, this well-maintained h...

3 Beds
4 Baths
MDKE2001344 MLS

218 Camelot Dr, Chestertown $459,500

Stunning, well cared for home in Coventry Farms II is the envy of many with it's beautiful landscaping and stone accent, an incredible value. Looking for Turn Key? Seller...

5 Beds
4 Baths
MDKE2001442 MLS

107 Chester Arms Dr, Chestertown $229,900

Buying a new home in historic Chestertown continues to be the best option on the Eastern Shore for those looking to retire or start a new family surrounded by the tranqui...

3 Beds
2 Baths
MDKE2001440 MLS

104 Maple Ave, Chestertown $500,000

GUIDED TOUR ON THURSDAY, MAY 26TH, PROMPTLY AT 11:00 AM! List price to be opening bid at online only auction. Registration and bidding begins Thursday, June 2nd and ends ...

MDKE2001438 MLS

123 N Queen St, Chestertown $487,500

Here's a sweet spot on historic Queen Street... not only a great location within a block or two of everything Chestertown, but also a sweet spot to call home with front a...

3 Beds
3 Baths
MDKE2001424 MLS

121 Washington Ave, Chestertown $850,000

GUIDED TOUR ON THURSDAY, MAY 26TH, PROMPTLY AT 11:30 AM! List price to be opening bid for online only auction. Registration and bidding begins Thursday, June 2nd and ends...

MDKE2001432 MLS

103 S Kent St, Chestertown $349,000

This home has undergone a tasteful renovation including new plumbing, wiring, framing, mechanicals, and roof. The home offers a terrific floor plan with decorative touche...

2 Beds
2 Baths
MDKE2001374 MLS

300 Gatling Dr, Chestertown $350,000

Being sold to settle an estate, LIST PRICE STARTING PRICE, Deposit required to Bid $25,000, buyers premium applies, see full terms and conditions at the website, Conten...

4 Beds
2 Baths
MDQA2003570 MLS

213 Pine Cove Ln, Chestertown $60,000

Don’t miss this private .52 acre lot ready to be built on! It’s mostly cleared and perc approved. Located down a secluded dirt lane, this lot offers privacy with convenie...

MDQA2003322 MLS

314 Devon Dr, Chestertown $450,000

This beautiful brick-front colonial home features a multitude of upgrades, three finished levels, and is located in a quiet and friendly neighborhood. Stunning laminate P...

4 Beds
4 Baths
MDKE2001372 MLS

3 Reed Ct, Chestertown $439,000

Located in a small cul-de-sac, this terrific home offers so much. The primary bedroom on the first floor has an attached bath, there are three closets for those of us wh...

3 Beds
3 Baths
MDKE2001422 MLS

22153 1st Point Rd, Chestertown $1,075,000

Water, water everywhere! This incredibly unique property is situated on a sheltered deep-water creek offering a westerly, southwesterly exposure with uncompromised sunset...

3 Beds
2 Baths
MDKE2001246 MLS

23081 Old Fairlee Rd, Chestertown $249,000

This charming family home located in the Village of Fairlee requires rehab work however when entering the property one will agree that indeed it has alot of character w...