Chestertown MD Real Estate & Homes for Sale

114 Properties Found

The median home value in Chestertown, MD is $242,500. 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 Chestertown, MD is $242,500. 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 you’re interested in, contact a Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


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Beds:
4
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10354331
Type:
Single Family
Subdivision:
N/A
Lot size:
0.06 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Live in the heart of Historic Chestertown, Water views of the Chester River from the back of the house. Historic Water Street in front. Charming Colonial Revival house overlooking Washington College's Presidents gardens. A great place to sit on back or front porch and watch the world go by. Off street parking on the river side, on street parking in front. Easy to show, come and see.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10353893
Type:
Single Family
Subdivision:
None
Lot size:
2.01 Acres
Year built:
1973
A broker reciprocity listing Courtesy: CR Realty
View additional info

Quiet country living, but yet close to town, the Chester River, and all of the amenities! This house is in immaculate shape and holds endless opportunities! There are beautiful hardwood floors, a master bedroom, a huge basement that can easily be finished for extra living space, and breath taking views of farmland. This house is priced to sell and to make it your dream home.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10351878
Type:
Other
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Year built:
1995
A broker reciprocity listing Courtesy: Riverview Realty, LLC.
View additional info

Beautifully remolded with large eat in kitchen, crown molding, new cabinets & appliances. new septic, heat pump, pergo flooring and ceramic tile central bath. Master bedroom has double closets and new marble look showered bath. Fresh paint & carpet. Newer windows and roof. Huge great room w/ sliding door to a deck & new mini split system, separate laundry & utility room. agent related to owner

Open House:

Thursday, 9/27 11:00-2:00PM

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10350299
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.23 Acres
Year built:
2007
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Beautiful Colonial with finished basement, a deck, wood floors along with carpeting, open floor plan with kitchen and family room. Shows like new in Coventry Subdivision. Attached, front loading 2 car garage with remotes, large master with a master bath, walk in closet, carpet. A comfortable home with a nice fenced back yard. Fresh paint with delightful colors. Quartz countertops.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,424
Status:
NEW LISTING
MLS#:
KE10350091
Type:
Single Family
Subdivision:
Gerogetown
Lot size:
1 Acres
Year built:
1920
A broker reciprocity listing Courtesy: The Hogans Agency Inc.
View additional info

Drastic reduction on this fixer upper - priced to sell. This is an estate sale and sold "AS IS". Public water and sewer to this 1 acre lot located in a quiet residential area with several nearby homes being renovated on Georgetown Road. Make an offer!

Beds:
2
Baths:
2.00
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
KE10350099
Type:
Single Family
Subdivision:
None
Lot size:
0.17 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Village Real Estate Company LLC
View additional info

Nice location in Chestertown, walking distance to Washington College and downtown shops and restaurants. Private back yard, screened front porch. Your next project awaits!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,055
Status:
Active
MLS#:
QA10347672
Type:
Single Family
Subdivision:
Sarah Skipper Lands
Lot size:
0.58 Acres
Year built:
1974
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Located in the 50' Critical Area Buffer, this location will support a value between $800k - $900k. Elevate the home to meet FEMA requirements - $35,000 (approx), Renovation of existing home - $260,000 (approx) and Dock Installation w/boat and jet-ski lifts - $60k. Excellent Opportunity to own a newly renovated waterfront on the Chester River for less than $800k.

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10337437
Type:
Single Family
Subdivision:
Reba L Anthony Subdivision
Lot size:
1.9 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Premium materials and finishes,including yellow pine floors reclaimed from Camden Yards,really set this waterfront cape apart.Crown moulding,wainscoting,panel doors,fireplace,sun room and master on first floor are among the many amenities.Studio with AC/Heat is surrounded by a Williamsburg Garden and a gazebo sits waterside.Very private and includes separate .44 perc approved lot.Walk to C-town.

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10341642
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Year built:
2004
A broker reciprocity listing Courtesy: Doug Ashley Realtors, LLC
View additional info

Wonderful well kept home on quiet cul de sac in Chesapeake Landing, just across the street from Marina and Harbor House Restaurant. Nice floor plan with large bedrooms, loads of storage and fenced in back yard with privacy and raised paver patio. Voluntary Community Association with water Privileges! This home is turn key. Just bring the boat!

Beds:
5
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10336279
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.85 Acres
Year built:
2006
A broker reciprocity listing Courtesy: CR Realty
View additional info

Perfect location and home for a large family! This open floor plan home includes a 3 year old salt water pool, brand new appliances, granite counters, full privacy fence that locks, tankless water heater, new ceiling fans and light fixtures, crown molding, jetted tub, two car garage, dock access, and more! Come see all that this home has to offer within 2400+ sq ft on nearly an acre!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,808
Status:
Active
MLS#:
KE10336364
Type:
Single Family
Subdivision:
Just Outside Chestertown
Lot size:
7.89 Acres
Year built:
1981
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Wooded and private, this 7+ acre property offers something for everyone! Main level living at its best with an updated kitchen offering chef's appliances and tile floors, random width Brazilian Cherry floors, radiant heat throughout the whole house, Florida room, multi-level decks and in-ground pool, plus a detached 3-bay garage with finished guest apartment and workshop.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,782
Status:
Active
MLS#:
KE10335969
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.37 Acres
Year built:
1943
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

The Eastern Shore Lifestyle awaits you in this charming water view home, perfectly situated to enjoy the stunning views of the Chesapeake Bay and its sunsets! The 3 bed, 2 bath Cape Cod has been meticulously maintained and renovated to offer an updated kitchen with granite counters, hardwood floors throughout the main level, new carpet and bathroom upstairs and a new roof.

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10335202
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.44 Acres
Year built:
1980
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Beautiful Home Located In Coveted Mile Tree Village!! This 3 bedroom 2 bath house offers great views, screened in porch, 1st floor master with handicap accessible shower, and fenced in back yard with kayak/canoe launch. The property is also within short walking or driving distance of downtown, the college, the hospital and both shopping centers. Call to schedule your showing today.

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10333119
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.38 Acres
Year built:
1984
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

Wow, wow; is this ever a beautiful "home" with so many upgrades; living room opens to dining room, opens to kitchen with island, SS appliances, extra-wide 48" staircase to upstairs; beautiful master BR with 2 walk-in closets, double vanities, dual-system heat/AC with baseboard backup; Family room with fireplace opens to family-style screened-in porch, 2-car attached garage; front porch with swing.

Beds:
3
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10331488
Type:
Single Family
Subdivision:
None
Lot size:
1.45 Acres
Year built:
2005
A broker reciprocity listing Courtesy: Douglas Realty LLC
View additional info

Nice Home! Plenty of living space a must see! Almost an acre and a half, three car garage/workshop, floored attic w/inside access,(could be extra living space). Mold remediation recently done in crawl space w/5 year warranty. Brand new septic approved for 4 bedrooms. This home won't be on the market long! As Is addendum required.

Beds:
1
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10329495
Type:
Single Family
Subdivision:
Chestertown
Lot size:
4 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Coldwell Banker Residential Brokerage-Annapolis
View additional info

Nice 4 acre parcel of land with small cottage. Cottage needs complete rehabilitation or removal. Working well on property has been tested within the last year. No septic. Utility easement through back of property. Nice location on quiet street. Nice piece of land at a great price. Build your own home on this quiet parcel. Land alone is accessed at $60,000 / $15,000 per acre.

Beds:
3
Baths:
2.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10327781
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.49 Acres
Year built:
1990
A broker reciprocity listing Courtesy: Maryland REO Connection, LLC
View additional info

WATERFRONT 2 STORY IN CHESTER HARBOR ON WOODED LOT COMPLETE WITH DOCK ! PAVED DRIVE DELIVERS YOU TO THIS CONTEMPORARY STYLE HOME WITH UPDATED KITCHEN AND BATHS. FLOOR PLAN OFFERS 2 MAIN LEVEL BEDROOMS. 1-2 ADDITIONAL UPPER LEVEL BEDROOMS. VOLUNTARY HOA OF $25 PER YEAR. GREAT HOUSE, GREAT LOT, GREAT VALUE !

Beds:
3
Baths:
1.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10327181
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
1.33 Acres
Year built:
1937
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Seller assumes buyer will be tearing down (or completely rebuilding) existing structures. Value is based on 200' of Chesapeake Bayfront, a "C" shaped assemblage of 3 parcels, 8 lots which includes one allocation for water/sewer. Several nearby neighbors have built/rebuilt Million$+ properties worthy of Architectural Digest. Several pictures provided for inspiration purposes!

Beds:
4
Baths:
5.00
Sq.Ft.:
2,656
Status:
Active
MLS#:
KE10326145
Type:
Single Family
Subdivision:
Quaker Neck
Lot size:
51.55 Acres
Year built:
1900
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

The location of the main house, 3 cottages, in-ground pool & pool house in the critical area buffer make this waterfront compound offering one that is extraordinary and extremely rare. Situated on the banks of Comegys Bight roughly 7.5 miles from Historic Chestertown is a 51.55-acre whimsical oasis with nature & riding trails, pastures, barns, farmland, woodlands... make this your Camelot...

Beds:
2
Baths:
1.00
Sq.Ft.:
800
Status:
Active
MLS#:
KE10323147
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.54 Acres
Year built:
1943
A broker reciprocity listing Courtesy: Champion Realty, Inc.
View additional info

Location! Location! Location! Cozy 1940's Bay-front Cottage on .54acre lot with spacious screened porch & detached 2-bay garage offers spectacular year round views of Chesapeake Bay. Being sold As Is. Fix up the existing cottage or build new. Flood insurance not required. Oversized lot grandfathered for home site. Public sewer. Don't let this rare gem get away!

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
QA10321311
Type:
Single Family
Subdivision:
None
Lot size:
23.98 Acres
Year built:
1988
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Surround yourself with nature on almost 24 waterfront acres (half open and half wooded), just 5 minutes from Historic Chestertown. Drive down the private paved lane to the main home situated in a park-like setting on Rosin Creek. Property also includes two small tenant houses & large detached garage. With a little vision & TLC, so much potential here! Judicious pruning would open up views!

Beds:
4
Baths:
3.00
Sq.Ft.:
2,268
Status:
Active
MLS#:
KE10314135
Type:
Single Family
Subdivision:
Tolchester Estates
Lot size:
0.92 Acres
Year built:
2000
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Custom Chesapeake Bay View Cape constructed in 2000, features main level master suite w/luxury master bath, Florida room off of the living room, spacious kitchen with breakfast nook, separate dining room and full basement. The lush landscape consists of fig trees and persimmon, grape arbor, and more! Just around the corner from The Shanty at Tolchester Marina.

Beds:
4
Baths:
4.00
Sq.Ft.:
4,402
Status:
Active
MLS#:
KE9013002
Type:
Single Family
Subdivision:
Quaker Neck
Lot size:
1.48 Acres
Year built:
1949
A broker reciprocity listing Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

One of Chestertown's most prestigious addresses. Located on the river halfway between town and "The Club". 1.48 acres of privacy. Professionally maintained and landscaped. The house has had one addition and two remodels. Large open floor plan,pool, guest/in-law suite,golf, gazebo, boating all make for endless entertaining possibilities.

Beds:
4
Baths:
2.00
Sq.Ft.:
1,260
Status:
Active
MLS#:
KE9012304
Type:
Single Family
Subdivision:
None
Lot size:
0.51 Acres
Year built:
1955
A broker reciprocity listing Courtesy: Rock Hall Properties Real Estate
View additional info

Updated & clean, this saltbox style home was remodeled in 2014 with wood floors, new kitchen & baths, & new carpet in the bedrooms. A newer heat pump & vinyl windows make this an efficient, affordable home to operate. There's plenty of space with 4 bedrooms, plus 2 full baths. A full basement provides storage space too. You''ll enjoy views of the farm across the street & relaxing on the rear deck

Beds:
7
Baths:
9.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
KE10315030
Type:
Single Family
Subdivision:
Quaker Neck
Lot size:
150.77 Acres
Year built:
1965
A broker reciprocity listing Courtesy: Cross Street Realtors LLC
View additional info

Bachelors Hope Farm, available for the first time in 50+years, is a once-in-a-lifetime waterfront & hunting farm. 9600 sq.ft., 7bed Main Home is situated within feet of the Chester River. 420' dock has 8' MLW, water & electric, w/ railway. 3000'+ of River frontage w/ 1400'+ revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale.

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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.

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