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Chestertown MD Real Estate & Homes For Sale

296 Properties Found

The median home value in Chestertown, MD is $249,700. This is higher than the county median home value of $217,100. The national median home value is $152,300. The average price of homes sold in Chestertown, MD is $249,700. Approximately 40.15% of Chestertown homes are owned, compared to 43.33% rented, while 16.52% 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 you’re interested in, contact a Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


1 - 10 of 296 Properties Displayed
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$4,900,000

22607 HANDY POINT RD CHESTERTOWN, MD 21620

Beds:
7
Baths:
7.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE7315421
Type:
Single Family, Farm
Subdivision:
CHESTERTOWN
Lot size:
21.02 Acres
Year built:
1785
A broker reciprocity listing Listing Provided Courtesy Of: Chesapeake Real Estate Associates, LLC
View additional info

Historically significant home on 21 acres, 1000' on the Chesapeake Bay. Modern 4 stall stable w/run-ins, tackroom, fenced pastures, indoor pool, beach bath house, caretakers home, and several outbuildings. Grand rooms extensively renovated. Home features 7BR/5BA, gourmet kitchen, library, den, breakfast room, several sitting rooms, converted granary now family room, bar, exercise & steam room.

$3,950,000

301 POND LN CHESTERTOWN, MD 21620

Beds:
4
Baths:
2.00
Sq.Ft.:
2,400
Status:
Active
MLS#:
QA7763778
Type:
Single Family, Farm
Subdivision:
HAMBLETON CREEK FARM
Lot size:
391.25 Acres
Year built:
1893
A broker reciprocity listing Listing Provided Courtesy Of: Chesapeake Real Estate Associates, LLC
View additional info

Two separated parcels sold as one, 391 total ac., 300 tillable ac. well drained productive soils, 10 acre lake, 8 impoundment, 8 goose pits, excellent hunting, deer, upland game. 19th century renovated farm house, large equipment storage barn, 8 bay open front garage, all structures in good to excellent condition. Sale contingent on 1031 tax exchange, seller purchase of other farms.

$3,950,000

301 POND LANE LN CHESTERTOWN, MD 21620

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA7762679
Type:
Land
Subdivision:
HAMBLETON CREEK FARMS
Lot size:
391.25 Acres
A broker reciprocity listing Listing Provided Courtesy Of: Chesapeake Real Estate Associates, LLC
View additional info

Two separate parcels sold as one, 391 total ac., 300 tillable ac. well drained productive soils, 10 acre lake, 8 impoundments, 8 goose pits, excellent hunting, deer, upland game. 19th century renovated farm house, large equipment storage barn, 8 car open front garage, all structures in good to excellent condition. Sale contingent on 1031 tax exchange, sellers purchase of other farms.

$3,950,000

201 TALBOT BOULEVARD CHESTERTOWN, MD 21620

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE6563339
Type:
Industrial
Subdivision:
RADCLIFF CREEK IND. PARK
Lot size:
22.85 Acres
Year built:
2008
A broker reciprocity listing Listing Provided Courtesy Of: The Hogans Agency
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Valuable property zoned, LI-1 within the town limits of Chestertown. Road frontage on both RT. 291 and Talbot BLVD. 22.85 acres with preliminary site drawings available. Many uses with unlimited potential. Possible 55+ Senior Village and possible 55+ Nursing/Rehab use.

$3,900,000

5793 QUAKER NECK LANDING CHESTERTOWN, MD 21620

Beds:
4
Baths:
5.00
Sq.Ft.:
4,314
Status:
Active
MLS#:
KE7131349
Type:
Single Family, Farm
Subdivision:
CHESTERTOWN
Lot size:
65.13 Acres
Year built:
1970
A broker reciprocity listing Listing Provided Courtesy Of: Lacaze Meredith Real Estate
View additional info

Kentfields is located on Quaker Neck close to Chestertown on Maryland's beautiful Eastern Shore. This 65 acre estate is on Jarrett Creek, just off the Chester River and Chesapeake Bay. The home provides a comfortable and casual Eastern Shore Lifestyle. A unique living & sporting & entertaining property. Extraordinary human and wildlife habit

$2,250,000

27349 VENARINGHAM LN CHESTERTOWN, MD 21620

Beds:
5
Baths:
5.00
Sq.Ft.:
4,968
Status:
Active
MLS#:
KE6606019
Type:
Single Family, Farm
Subdivision:
VENARINGHAM
Lot size:
65.52 Acres
Year built:
1994
A broker reciprocity listing Listing Provided Courtesy Of: Sassafras River Realty, Ltd.
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Waterfront farm on the Chester River with marvelous hunting off the marsh & on 2 ponds. House has 4 BR, 3 1/2 baths, plenty of closets space, new open addition in 2003 w/tile hot tub & 6.5 x 12 sauna. 3 Car garage w/lrg guest room, full BA, sink & frig. 3 Morton buildings, 20 acres fenced. Orchard. Electric lift on pier, beach and picnic area. Expansive views. Well maintained property & imps.

$1,900,000

25341 LEARMAN RD CHESTERTOWN, MD 21620

Beds:
5
Baths:
4.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE7843304
Type:
Single Family, Farm
Subdivision:
CHESTERTOWN
Lot size:
46.09 Acres
Year built:
1920
A broker reciprocity listing Listing Provided Courtesy Of: Cross Street Realtors LLC
View additional info

Broad Reach - Kent Co's finest waterfront offering on the Chester River. 46 acres in a pastoral setting with the main house and guest cottage situated within 50' of the River offering unobstructed water views. 125+ deep water (7+) pier serviced by electric, water & fuel. The entrance drive crosses a fresh water pond with mature trees that enhance the natural landscape.

$1,800,000

LEVERAGE CHESTERTOWN, MD 21620

Beds:
n/a
Baths:
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA7283115
Type:
Land
Subdivision:
BLAKEFIELD
Lot size:
58 Acres
A broker reciprocity listing Listing Provided Courtesy Of: Chesapeake Real Estate Associates, LLC
View additional info

Great opportunity to buy now and reep the benifits later on this 23 lot recorded subdivision. They are not creating many more lots in the county. This price includes lots 3-25 which are all 1 plus acre lots, Call office for plat. This price reflects developer installing road.Buying with a take down schedule is an option.

$1,799,000

6960 PENTRIDGE LN CHESTERTOWN, MD 21620

Beds:
3
Baths:
4.00
Sq.Ft.:
3,102
Status:
Active
MLS#:
KE7808634
Type:
Single Family
Subdivision:
LANGFORD FARM
Lot size:
40.27 Acres
Year built:
1993
A broker reciprocity listing Listing Provided Courtesy Of: The Hogans Agency Inc.
View additional info

A delightful home with a great flow for entertaining-- inside and out. Water views from all rooms, screened-in porch, and slate patio with pergola.Over 40 acres, including deep-water pier, waterfront and pit blinds for duck and geese hunting, and 3 tree stands for deer hunting. Enjoy the privacy and serenity of this outstanding property in a desirable neighborhood close to historic Chestertown.

$1,500,000

21094 IOWA AVE CHESTERTOWN, MD 21620

Beds:
4
Baths:
4.00
Sq.Ft.:
4,603
Status:
Active
MLS#:
KE7769331
Type:
Single Family
Subdivision:
TOLCHESTER ESTATES
Lot size:
0.67 Acres
Year built:
2005
A broker reciprocity listing Listing Provided Courtesy Of: TTR Sothebys International Realty
View additional info

Spectacular residence on the shore of the Chesapeake Bay near Tolchester Beach/Marina. Newly built in the past 5 yrs. with every quality detail available.Gourmet kit., LR/DR with 30'of windows/doors to huge outdoor patio/decks overlooking the Bay with spectacular sunsets. Separate finished Carriage house apartment/studio. Lush gardens with mature landscaping, pond, hot tub,PRIVACY.Special...

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The data on this web site comes in part from Metropolitan Regional Information Systems (MRIS). The listings presented on behalf of MRIS may come from many different brokers but all MRIS' listings may not be visible on this site. Information is believed to be reliable, but not guaranteed.

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