Chestertown MD Real Estate & Homes for Sale

117 Properties Found

The median home value in Chestertown, MD is $243,500. 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 $243,500. 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:
4.00
Sq.Ft.:
3,128
Status:
NEW LISTING
MLS#:
1008575416
Type:
Single Family
Subdivision:
None Available
Lot size:
10 Acres
Year built:
2005
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Georgian style home is situated on a serene, rural 10-acres, yet is conveniently located just 2 miles from the colonial town of Chestertown. Designed by the architect, Andrea Lombardini, and built in 2005, the thoughtfully designed interior lends an airy elegance harmoniously linking the sunlit living areas, including the first floor master suite. Taking full advantage of the pastoral views, the home showcases the finest details including random width wood floors, built-ins, high ceilings and a terrace overlooking the naturally beautiful setting. Chestertown offers a river walk, brick lined streets with 18th century homes, galleries, live theater and cafes. It enjoys a vibrant arts community, outdoor educational programs and is home to Washington College. Located about 90-minutes from Washington and Philadelphia.

Beds:
2
Baths:
1.00
Sq.Ft.:
1,168
Status:
NEW LISTING
MLS#:
1009918978
Type:
Single Family
Subdivision:
Fairlee
Lot size:
2 Acres
Year built:
1948
Courtesy: Champion Realty, Inc.
View additional info
Beds:
3
Baths:
1.00
Sq.Ft.:
1,125
Status:
NEW LISTING
MLS#:
1008362670
Type:
Single Family
Subdivision:
Beautiful Quaker Neck Peninsula
Lot size:
0.47 Acres
Year built:
1949
Courtesy: Doug Ashley Realtors, LLC
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Bring your water toys and enjoy this cute cottage located approximately 1.5 miles from Quaker Neck Landing! Family/dining area combination has wood floors, a wood burning stove and beamed wood ceiling. First floor bedroom has walk-in closet and hookup for stack-able washer/dryer. Upstairs has a 2nd bedroom and currently used as "the Bunk Room" . The grounds have been well landscaped and there is even an outdoor shower! Use as a retreat, primary home, hunting cabin/cottage, etc. Not too far from Historic downtown Chestertown!!

Beds:
5
Baths:
4.00
Sq.Ft.:
5,367
Status:
NEW LISTING
MLS#:
1009688038
Type:
Single Family
Subdivision:
None
Lot size:
13.17 Acres
Year built:
2006
Courtesy: Champion Realty, Inc.
View additional info
Beds:
3
Baths:
2.00
Sq.Ft.:
1,200
Status:
NEW LISTING
MLS#:
1008616880
Type:
Single Family
Subdivision:
Militota
Lot size:
2 Acres
Year built:
1972
Courtesy: Doug Ashley Realtors, LLC
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Double-wide home on a great 2 acre corner lot! House is being sold "AS IS" but with a little work this could be a great home. Has a relatively new metal roof.

Beds:
3
Baths:
2.00
Sq.Ft.:
852
Status:
Active
MLS#:
1009223586
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.34 Acres
Year built:
1987
Courtesy: Wyble Enterprises
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Raised rancher with 3-bedrooms, 1 1/2 baths, partially-finished basement, deck, 1-car garage, central heat and AC. om a water-privileged community 3 miles from Chestertown. Being Sold AS IS with inspections. Possible investment opportunity.

Open House:

Saturday, 10/27 12:00-2:00PM

Beds:
4
Baths:
4.00
Sq.Ft.:
3,799
Status:
Active
MLS#:
1008146650
Type:
Single Family
Subdivision:
Coventry Farm
Lot size:
0.32 Acres
Year built:
2008
Courtesy: Doug Ashley Realtors, LLC
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Gorgeous Home, Energy efficient, upgraded, has a custom sauna in the rec area, a workout room, gorgeous wood floors, and a gourmet kitchen with a sunny breakfast room. There is a beautiful dining room, and office/den, outside has a deck and beautifully landscaped home. This owner had the home built, and paid for many energy efficient upgrades. Welcome to a wonderful lifestyle in Historic Chestertown. Washington College features art, drama, sports and a lifetime learning center. Chestertown is on the Chester River and there are many activities to enjoy!

Beds:
4
Baths:
3.00
Sq.Ft.:
n/a
Status:
Active
MLS#:
1008349662
Type:
Single Family
Subdivision:
Coventry Farms
Lot size:
0.26 Acres
Year built:
2009
Courtesy: Real Estate Professionals, Inc.
View additional info

Stately Colonial Style Home now Available in the Coventry Farms Neighborhood of Chestertown. This Home Features 4 Bedrooms and 2.5 Baths, a Gourmet Kitchen with Breakfast Nook and Separate Dining Room, and Finished Basement with Access to Spacious Back Yard. Seller Financing May Be Available

Beds:
7
Baths:
9.00
Sq.Ft.:
9,651
Status:
Active
MLS#:
1008176730
Type:
Single Family
Subdivision:
Quaker Neck
Lot size:
164.13 Acres
Year built:
1965
Courtesy: Cross Street Realtors LLC
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Bachelors Hope Farm, available for the first time in 50+ years, is a once-in-a-lifetime waterfront & hunting farm. 9,600 square foot, 7 bed Main Home is situated within feet of the Chester River. 420 foot dock has 8 feet MLW, water & electric, with railway. 3,000+ feet of River frontage with 1,400+ foot revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4 bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale.

Beds:
7
Baths:
9.00
Sq.Ft.:
9,651
Status:
Active
MLS#:
1002149830
Type:
Farm
Subdivision:
Quaker Neck
Lot size:
164.13 Acres
Year built:
1965
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. 9,600 square foot, 7 bed Main Home is situated within feet of the Chester River. 420 foot dock has 8 feet MLW, water & electric, with railway. 3,000+ feet of River frontage with 1,400+ foot revetment. 164+ acres: 96 tillable, 43 wooded & 3 ponds. 4 bed Farm Home & barn. Exquisite & prestigious Quaker Neck locale.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,423
Status:
Active
MLS#:
1007547006
Type:
Single Family
Subdivision:
The Flyway
Lot size:
1 Acres
Year built:
1998
Courtesy: Cross Street Realtors LLC
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This Is It! Situated on 1 acre in the Flyway on a cul-de-sac is a split bedroom open plan design custom-built Ranch home. Just shy of 2,500 sq.ft., this 3 bedroom, 2.5 bathroom home also features a 4-season room, great room, separate living room with french doors, and finished bonus room above the insulated 2-car garage. The 1,500 gal septic will accommodate more bedrooms if desired. From the crawl space to the roof to the sizeable workshop/shed, this home has been meticulously cared for and loved over the years. Excellent Sellers to follow!

Beds:
3
Baths:
2.00
Sq.Ft.:
2,052
Status:
Active
MLS#:
1006503594
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.25 Acres
Year built:
1988
Courtesy: Doug Ashley Realtors, LLC
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In Chestertown on a quiet cul-da-sac street with only a handful of houses. Roomy Cape Cod with living room, den as well as a first floor bedroom. Eat in kitchen, separate dining room, Peaceful screened in porch facing wooded area. 24x24 pole shed with lots of options. Replacement Windows, Roof 7 years young w/warrenty(30 yr Shingles) Already for new owners.

Beds:
5
Baths:
4.00
Sq.Ft.:
4,257
Status:
Active
MLS#:
1005644966
Type:
Single Family
Subdivision:
Fairgale Properties
Lot size:
3.55 Acres
Year built:
2002
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Fairlee Creek waterfront haven is set on a private 3.5-acres with water views throughout the home. Built in 2002 with a 2005 addition, the open design with great room, large kitchen, loft and deck invites outdoor living and entertaining. Features include a first floor Master Suite, an in-law apartment and detached 2 car garage. Also included is a deeded boat slip with lift at the community dock. F

Beds:
4
Baths:
2.00
Sq.Ft.:
2,064
Status:
Active
MLS#:
1006633640
Type:
Single Family
Subdivision:
N/A
Lot size:
0.06 Acres
Year built:
1900
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.:
1,612
Status:
Active
MLS#:
1006073456
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Year built:
1995
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

Beds:
3
Baths:
2.00
Sq.Ft.:
1,424
Status:
Active
MLS#:
1005610694
Type:
Single Family
Subdivision:
Gerogetown
Lot size:
1 Acres
Year built:
1920
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.:
1,762
Status:
Active
MLS#:
1005610732
Type:
Single Family
Subdivision:
None
Lot size:
0.17 Acres
Year built:
1900
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#:
1004251654
Type:
Single Family
Subdivision:
Sarah Skipper Lands
Lot size:
0.57 Acres
Year built:
1974
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#:
1002400784
Type:
Single Family
Subdivision:
Reba L Anthony Subdivision
Lot size:
1.9 Acres
Year built:
1990
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.:
1,624
Status:
Active
MLS#:
1002775292
Type:
Single Family
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Year built:
2004
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:
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#:
1002352414
Type:
Single Family
Subdivision:
Mile Tree Village
Lot size:
0.44 Acres
Year built:
1980
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#:
1002335762
Type:
Single Family
Subdivision:
Chester Harbor
Lot size:
0.38 Acres
Year built:
1984
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:
2.00
Sq.Ft.:
2,437
Status:
Active
MLS#:
1002276762
Type:
Single Family
Subdivision:
Langford Bay Estates
Lot size:
1.84 Acres
Year built:
1986
Courtesy: Gunther-McClary Real Estate
View additional info

Cozy 3 bdr waterfront home with all the natural, private surroundings the eastern shore has to offer. Very easy access to more than 300 feet of bulkheaded shoreline. 2 large detached garages to store all the waterfront toys you will need to take advantage of all Langford Creek has to provide, fishing, crabbing, year round hunting or whatever you waterfront dreams desire.

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The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which participates, and is provided by BRIGHT through a licensing agreement. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright BRIGHT, All Rights Reserved
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