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Chestertown MD Real Estate & Homes for Sale

110 Properties Found

The median home value in Chestertown, MD is $232,000 This is higher than the county median home value of $183,500. The national median home value is $185,800. The average price of homes sold in , is $. Approximately 41.87% of Chestertown homes are owned, compared to 42.32% rented, while 15.82% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. . Commercial properties are also available. If you see a property Chestertown real estate agent to arrange a tour today !
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1–25 of 110 properties displayed
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$298,500

409 Bell Avenue Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10103223
Type:
Single Family
Subdivision:
College Heights
Lot size:
0.5825 Acres
Year built:
1969
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Beautifully cared for. Gorgeous 3 bedrooms, 2.5 baths, living room/fp/dining room on the main level with gorgeous lighting. The main level has all you need for one level living. But there is a lower level, a 2 car garage, family room with a fireplace, an office/study, a wet bar/kitchenette and plenty of storage with a half bath, fenced back yard! Solar panels convey to buyer at no cost.

$325,000

101 River Road Chestertown, MD 21620

Beds:
5
Baths:
3.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
QA10102902
Type:
Single Family
Subdivision:
Sarah Skipper Lands
Lot size:
1 Acres
Year built:
1977
A broker reciprocity listing Courtesy: Brenton and Clark Realty LLC
View additional info

Spacious 5 bedroom, 2.5 bath dutch colonial on large corner lot, beautiful new kitchen, dining w/ beam ceiling & wood stove, family room, den/office, laundry room, fenced backyard, storage shed and 1 car garage...recent upgrades include HVAC (dual zoned), septic, some flooring, paint, front door, roof-only 12 years old.... Just minutes to the Chester River and to Downtown Historic Chestertown

$380,000

12 Cedar Chase Court Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10102718
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.5245 Acres
Year built:
1992
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Original owner---house custom built by Alton Darling in sought-after Mile Tree Village. Private cul-de-sac- location, with wooded back yard and water views. Rural feeling , yet convenient to College and Town. Open floor plan for entertaining. One-floor living with Guest Bedrooms up. Well cared for and ready to move in.

$375,000

110 Mill Street S Chestertown, MD 21620

Beds:
3
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10094461
Type:
Single Family
Subdivision:
Historic Chestertown
Lot size:
0.2014 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Gracious, elegant & charming describe this wonderful home in the heart of the Historic District. Beautiful original features include crown molding, wood floors, interior columns & fireplaces. Enjoyable enclosed glass porch. Lovely slate patio & garden for outdoor living. Income producing apt or Au-pair, in-law apt. Main house has 2 BR & 2 Ba. Apt has 1 BR Bath, LR & kitchen. Barn-Garage & Workshop

$67,600

303 Roosevelt Drive Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10099367
Type:
Single Family
Subdivision:
Washington Park
Lot size:
0.6728 Acres
Year built:
1966
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
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Affordable ranch home in need of some love. Would make an excellent investment. Large living room, updated kitchen, and HUGE backyard with shed! Schedule your showing today!

$224,900

724 Deep Landing Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10099132
Type:
Single Family
Subdivision:
Pine Cove
Lot size:
0.4995 Acres
Year built:
2017
A broker reciprocity listing Courtesy: Coldwell Banker Waterman Realty
View additional info

Home under construction. Can be completed in 60 days. County boat ramp. Modern, open floor plan. Granite counter tops. Master suite with separate shower and jetted soaking tub. Hardwood floors. Cathedral ceilings. Walk in closet. Two car garage. Beautiful peaceful setting. Stock photos shown.

$329,000

22400 Great Oak Landing Road Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10095064
Type:
Single Family
Subdivision:
Great Oak Estates
Lot size:
1.03 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Pristine and move in ready! So much to love including custom cherry cabinets, hardwoods, main floor master, open floor plan, gas fire, spacious walk in attic storage/bonus room, solar panels. Backs to woods with extensive perennial plantings and small pond. If you love nature this is your spot! Amenities include 9 hole golf course, pool, marina, and boat slips available. Handicap accessible.

$330,000

212 Washington Avenue Chestertown, MD 21620

Beds:
5
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10094679
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.2525 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Benson & Mangold, LLC
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Grand old Chestertown Colonial. High ceilings, beautiful moldings with all the craftsmanship of yesteryear. Huge yard with two car detached garage/workshop. Close to the college and downtown.

$450,000

8954 Orchard Drive Chestertown, MD 21620

Beds:
3
Baths:
3.00
Sq.Ft.:
5,150
Status:
Active
MLS#:
KE10090243
Type:
Single Family
Subdivision:
Orchard Hill
Lot size:
1.83 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

This custom home offers a unique combination of traditional living space with large flex-use areas in a finished lower level plus a free-standing 1100 sq. ft. studio/office/guest house. A total of 6,000+ s.f. on 1.8 peaceful acres. Bright spacious living areas. Private master suite opens to sunroom. Beautiful white oak floors. Click the virtual tour link and Imagine the possibilities!

$139,000

21892 Tolchester Beach Road Chestertown, MD 21620

Beds:
2
Baths:
1.00
Sq.Ft.:
816
Status:
Active
MLS#:
KE10091449
Type:
Single Family
Subdivision:
None
Lot size:
3.032 Acres
Year built:
1964
A broker reciprocity listing Courtesy: RE/MAX Chesapeake
View additional info

Cute little rancher in the heart of Kent County. Near the wildlife areas and the waters in and around Kent County. Enjoy just over 3 acres of land. New Septic, heater, kitchen and appliances. New Hot water heater too! Stop out and give this one a look... short drive to Chestertown and Rock Hall.

$259,900

349 Burchard Sawmill Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10091207
Type:
Single Family
Subdivision:
In The Country
Lot size:
2 Acres
Year built:
2017
A broker reciprocity listing Courtesy: Brenton and Clark Realty LLC
View additional info

Brand new home, open floor plan rancher nestled on 2 peaceful acres, 3 bedrooms, 2 baths, beautiful crisp clean kitchen with island/breakfast bar and SS appliances, spacious living room and large deck, MUST SEE!!...MHBR # 2347

$210,000

303 Campus Avenue Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10089985
Type:
Single Family
Subdivision:
Byford Development
Lot size:
0.3444 Acres
Year built:
1963
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Perfect one level living in this brick rancher located just a few blocks from Washington College. Living room has fireplace with built-in bookcase. Dining room has built-in corner cupboard. Freshly painted interior. You will spend most of your time in the rear Florida/sun room that over looks your semi-private backyard.

$409,000

105 Water Street UNIT 6 Chestertown, MD 21620

Beds:
2
Baths:
2.00
Sq.Ft.:
1,015
Status:
Active
MLS#:
KE10089392
Type:
Condo/Townhouse
Subdivision:
Water Street Condo
Year built:
1900
A broker reciprocity listing Courtesy: Brandywine Fine Properties Sothebys INTL Realty
View additional info

Beautiful Waterfront Condo in Historic Chestertown. Fabulous views of the Chester River with a deeded boat slip directly in front of the property. Historic Building with a gourmet kitchen that opens to a porch with stunning views of the Chester River. Fantastic landscaped yard with a sitting area for all.

$239,500

204 Valley Road Chestertown, MD 21620

Open House:

Saturday, 11/18 11:00-1:30PM

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10089371
Type:
Single Family
Subdivision:
College Heights
Lot size:
0.4944 Acres
Year built:
1959
A broker reciprocity listing Courtesy: Wyble Enterprises
View additional info

Attractive ranch home on deep lot. 3 large bedrooms, 2 1/2 baths, kitchen/dining area with fireplace, brick patio, breezeway to attached garage, brick patio. central air conditioning, hard surface driveway. Walk to college, medical facilities, and parks. Convenient to Chestertown's historic waterfront and vibrant Arts and Entertainment district.

$370,000

222 Washington Avenue Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10080545
Type:
Single Family
Subdivision:
N/A
Lot size:
0.2479 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

History, elegance and comfort combine in this well appointed Victorian treasure. Original pocket doors and chestnut moldings. Stunning eat-in kitchen with butcher block island, soapstone counters, cherry wood floors. Second floor screened porch overlooks bird- and butterfly-filled back garden. Three-car garage with full attic for storage. Walk or bike to Chester River, College, downtown.

$667,500

219 Water Street UNIT 3 Chestertown, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
2,800
Status:
Active
MLS#:
KE10086646
Type:
Condo/Townhouse
Subdivision:
Scott's Point
Year built:
2008
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fabulous Townhouse in desirable Scott's Point. Great waterviews of the Chester River & Wilmer Park. 2 deeded boat slips. Open Floor plan is enhanced by beautiful wood floors and cabinets. Wonderful Gourmet Kitchen opens to dining and living area. Balconies on each floor. First Floor Den options as bedroom. Large open airy rooms gives simple elegance with light. Walkable to everything downtown!

$2,495,000

27491 Morgnec Road Chestertown, MD 21620

Beds:
3
Baths:
5.00
Sq.Ft.:
4,436
Status:
Active
MLS#:
KE10086778
Type:
Single Family
Subdivision:
N/A
Lot size:
152.49 Acres
Year built:
1940
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Buckingham Farm, fronting the Chester River, is one of the most picturesque horse farms in MD. This prominent Thoroughbred Horse breeding operation raised home-bred, stakes-placed winners such as Green Alligator, Master Speaker, Crab Cakes...Receiving just as much love & attention was the property itself -152.49 acres improved w/main residence, historic train station, caretaker house, barns...

$75,000

8858 Georgetown Road Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10086557
Type:
Single Family
Subdivision:
Georgetown
Lot size:
1 Acres
Year built:
1920
A broker reciprocity listing Courtesy: The Hogans Agency
View additional info

With a little TLC this home could be great again. Within a 10 min drive to downtown Chestertown, Rock Hall and Betterton.

$39,900

8891 Georgetown Road Chestertown, MD 21620

Beds:
4
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10085565
Type:
Single Family
Subdivision:
None
Lot size:
2.1 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

investor alert! Rehab opportunity sitting on over 2 acreas

$99,900

421 Calvert Street Chestertown, MD 21620

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10085462
Type:
Townhouse
Subdivision:
Calvert Homes
Lot size:
0.0462 Acres
Year built:
1992
A broker reciprocity listing Courtesy: RE/MAX Sails Inc.
View additional info

MOVE IN READY TOWNHOME WITH COVERED PARKING! Newly updated w/ new carpet and paint throughout, spacious living room, eat-in kitchen w/ sliders to rear yard, main level half bath, Master bedroom w/ dual entry bath, and 2 additional bedrooms, large rear fenced yard, and off street parking with carport!

$424,900

520 Morgnec Road Chestertown, MD 21620

Beds:
5
Baths:
4.00
Sq.Ft.:
3,494
Status:
Active
MLS#:
KE10078037
Type:
Single Family
Subdivision:
Chestertown
Lot size:
10.92 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Custom built wonderful home in the country, but convenient to everything. Wildlife abundant w/BONUS PARCEL providing 10+ acres. Lower level w/2 BR,1.5BA, den, sep.kitchen/dining space and living areas. Potential in-law space or great entertaining space. Covered porch, wraparound deck w/amazing views. Private drive away from road! High ceilings, 3 zone HVAC, Lots of options for expanded families!

$549,000

209 Rivershore Road Chestertown, MD 21620

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10078797
Type:
Single Family
Subdivision:
Chestertown
Lot size:
1.67 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Chester River Cottage. Beautiful Chester River Views, a pier about 25 feet from this home. Nice water depth, and the house is adorable. Two bedrooms, not counting the loft, 1.5 baths, carport and a full unfinished basement. Charming built in's, a covered porch on the water side of the home. Fantastic opportunity to be five minutes from Chestertown, if that, but in a private location.

$314,995

10310 Hanesville Road Chestertown, MD 21620

Beds:
4
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10077502
Type:
Single Family
Subdivision:
No
Lot size:
2.05 Acres
Year built:
1989
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Peaceful living at its best.Only minutes from town ,shopping , parks, and public landings. This home has so much to offer with 2 acres of private, beautifully landscaped yard that is tree lined and partially fenced. Extra garage and barn with lean to in addition to the already attached 2 car garage.Updated appliances in the kitchen in fall 2017. Lots of space inside and out to suite everyone.

$165,000

2605 McGinnes Road Chestertown, MD 21620

Beds:
3
Baths:
1.00
Sq.Ft.:
1,555
Status:
Active
MLS#:
QA10076797
Type:
Single Family
Subdivision:
None
Lot size:
1.02 Acres
Year built:
1957
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Quaint house on 1+ acres with privacy from main road, just waiting for a little TLC. All weather enclosed breezeway with heat and AC. Hardwood floors throughout, built-ins and garage. New pressure tank and water softener in 2017. Property is sold strictly AS IS. More pictures to follow.

$995,000

9559 Chantilly Farm Lane Chestertown, MD 21620

Beds:
4
Baths:
3.00
Sq.Ft.:
3,778
Status:
Active
MLS#:
KE10075510
Type:
Single Family
Subdivision:
Chantilly Farm
Lot size:
30.45 Acres
Year built:
1955
A broker reciprocity listing Courtesy: TTR Sotheby's International Realty
View additional info

SPECTACULAR VIEWS FROM THIS 30 ACRE ESTATE ON THE CHESAPEAKE BAY WITH 1000 ft OF SHORE LINE AND GRADUAL SLOPE TO WATER, SANDY BEACH, GUEST COTTAGE, WINE CELLAR IN LARGE BASEMENT, 3 CAR GARAGE, GENERATOR, UNLIMITED WILDLIFE AND BEAUTY EVERYWHERE! FRESH WATER POND, TROMBE WALL, PASSIVE SOLAR BUILDING DESIGN IN FAMILY ROOM. HOUSE AND PROPERTY HAVE BEEN IMMACULATELY MAINTAINED.

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BRIGHT MLS - All information, regardless of source, should be verified by personal inspection by and/or with the appropriate professional(s). The information is not guaranteed. Measurements are solely for the purpose of marketing, may not be exact, and should not be relied upon for loan, valuation, or other purposes.

Chestertown MD Real Estate Listings Provided By:

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