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

8000 Rock Hall Rd, Chestertown $199,000

MECHANICS, GREEN THUMBS, CHEFS, NATURALISTS, AND FOOD TRUCKS are just a few of the entrepreneurs that should drop everything and call on this great offer: 1.52 acre corne...

MDKE2002174 MLS

121 Tuxedo Rd, Chestertown $284,900 ▼

Lovely like new all one floor home on extra large level lot with massive rear yard including mature trees and landscaping. Quality finishes throughout include wonderful k...

3 Beds
2 Baths
MDQA2005250 MLS

5179 Quaker Neck Rd, Chestertown $495,000

A unique opportunity! This charming brick building was originally built in the 1800s as a chapel named Mowbray Chapel, eventually abandoned and then the interior was com...

1 Baths
MDKE2002160 MLS

119 Chester Arms Dr, Chestertown $229,900

Come by this lovely BRAND NEW home in Chestertown. This home features Luxury Vinyl Flooring throughout, White Cabinets, Granite Counters, Spacious Living Room, Eat in Kit...

3 Beds
2 Baths
MDKE2002136 MLS

9088 Point Ln, Chestertown $1,100,000

Spectacular sunsets guaranteed with panoramic views of the Chesapeake Bay. Eastern shore waterfront home features gourmet kitchen , outdoor pergola, updated bedrooms and...

4 Beds
4 Baths
MDKE2002104 MLS

106 Drake Rd, Chestertown $360,000

Quality new construction that is very close to completion located in Chester Harbor. Wood floors throughout the living room, kitchen, dining area and mud room. Open flo...

3 Beds
2 Baths
MDQA2005124 MLS

Units 10 & 11 Washington Square Shopping Center, Chestertown image

Units 10 & 11 Washington Square Shopping Center, Chestertown $110,000

Local well known family restaurant currently serving Breakfast and Lunch Menus. Long established in the Washington Square Shopping Center in historic Chestertown, Marylan...

MDKE2002082 MLS

22600 Fairgale Farm Ln, Chestertown image

22600 Fairgale Farm Ln, Chestertown $2,250,000

Welcome to Fairgale, a tasteful waterfront community located minutes from Historic Chestertown and Rock Hall. This 36.66 total acre property with 1250+/- feet of stable s...

5 Beds
5 Baths
MDKE2002042 MLS

1005 Twin Ct, Chestertown $379,000 ▼

**REDUCED $20k!!** This spacious 3 bedroom, 2 bath rancher has all of the makings of a terrific home! Well-situated at the end of a cul-de-sac, the back yard has room...

3 Beds
2 Baths
MDKE2002040 MLS

22600 Fairgale Farm Ln, Chestertown $2,250,000

Welcome to Fairgale, a tasteful waterfront community located minutes from Historic Chestertown and Rock Hall. This 36.66 total acre property with 1250+/- feet of stable s...

5 Beds
5 Baths
MDKE2001990 MLS

8559 Camp Rd, Chestertown $329,000 ▼

This wonderful home is ideally located just outside of Chestertown on a corner lot in the desirable neighborhood known as Kent Acres. The home has been lovingly cared for...

3 Beds
2 Baths
MDKE2002002 MLS

25731 Collins Ave, Chestertown $795,000 ▼

This custom home is one of a kind and perfect for the golf enthusiast! Here you can walk out your back door to holes 14, 15, and 17 of the Chester River Yacht and County ...

3 Beds
3 Baths
MDKE2002010 MLS

121 Lyons Ln, Chestertown $875,000

This listing offers the unique opportunity to own two waterfront parcels, one improved by a beautiful 3-4 bedroom cape, and an adjacent perc approved lot all located less...

3 Beds
3 Baths
MDQA2004878 MLS

405 Oriole Rd, Chestertown $60,000

BUILD YOUR DREAM HOME ON THIS PERC APPROVED LOT IN THE CHESTER HARBOR COMMUNITY. $30.00 PER YEAR HOA IS VOLUNTARY, WHICH COVERS INSURANCE, GRASS CUTTING AND SNOW REMOVAL ...

MDQA2004736 MLS

1213 Ewingtown Rd, Chestertown $375,000

Almost complete, finishing touches in progress.....3 bedroom 2 bath contemporary rancher on 1 acre, kitchen with Island, primary bedroom with full bath and walk-in closet...

3 Beds
2 Baths
MDQA2004604 MLS

515 Cannon St, Chestertown $419,900

Located in the historic district of Chestertown! Well maintained with an open floor plan and currently tenant occupied. The gleaming wood floors on the main level glea...

3 Beds
3 Baths
MDKE2001966 MLS

141 Round Top Creek Ln, Chestertown image

141 Round Top Creek Ln, Chestertown $1,950,000

Magnificent Building Site on the Chester River. Being sold together, two lots totaling 30+ acres of property along the Chester River in Queen Anne's County. Private lane...

MDQA2004764 MLS

141 Round Top Creek Ln, Chestertown $1,950,000

Magnificent Building Site on the Chester River. Being sold together… two lots totaling 30+ acres of property along the Chester River in Queen Anne’s County. Private lane...