Chestertown MD Real Estate & Homes for Sale

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!


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Type:
Single Family
Sq.Ft.:
3,128
Status:
NEW LISTING
Beds:
4
Lot size:
10 Acres
Year built:
2005
Baths:
4.00
MLS#:
1008575416
Subdivision:
None Available

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
1,125
Status:
NEW LISTING
Beds:
3
Lot size:
0.47 Acres
Year built:
1949
Baths:
1.00
MLS#:
1008362670
Subdivision:
Beautiful Quaker Neck Peninsula

ADDITIONAL INFORMATION

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!!

Type:
Single Family
Sq.Ft.:
1,168
Status:
NEW LISTING
Beds:
2
Lot size:
2 Acres
Year built:
1948
Baths:
1.00
MLS#:
1009918978
Subdivision:
Fairlee

ADDITIONAL INFORMATION

Type:
Single Family
Sq.Ft.:
5,367
Status:
Active
Beds:
5
Lot size:
13.17 Acres
Year built:
2006
Baths:
4.00
MLS#:
1009688038
Subdivision:
None

ADDITIONAL INFORMATION

Type:
Single Family
Sq.Ft.:
1,200
Status:
Active
Beds:
3
Lot size:
2 Acres
Year built:
1972
Baths:
2.00
MLS#:
1008616880
Subdivision:
Militota

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
852
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1987
Baths:
2.00
MLS#:
1009223586
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

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

Type:
Single Family
Sq.Ft.:
3,799
Status:
Active
Beds:
4
Lot size:
0.32 Acres
Year built:
2008
Baths:
4.00
MLS#:
1008146650
Subdivision:
Coventry Farm

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
n/a
Status:
Active
Beds:
4
Lot size:
0.26 Acres
Year built:
2009
Baths:
3.00
MLS#:
1008349662
Subdivision:
Coventry Farms

ADDITIONAL INFORMATION

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

Type:
Single Family
Sq.Ft.:
9,651
Status:
Active
Beds:
7
Lot size:
164.13 Acres
Year built:
1965
Baths:
9.00
MLS#:
1008176730
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
2,423
Status:
Active
Beds:
3
Lot size:
1 Acres
Year built:
1998
Baths:
3.00
MLS#:
1007547006
Subdivision:
The Flyway

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
2,052
Status:
Active
Beds:
3
Lot size:
0.25 Acres
Year built:
1988
Baths:
2.00
MLS#:
1006503594
Subdivision:
Chestertown

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
4,257
Status:
Active
Beds:
5
Lot size:
3.55 Acres
Year built:
2002
Baths:
4.00
MLS#:
1005644966
Subdivision:
Fairgale Properties

ADDITIONAL INFORMATION

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

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

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
1,612
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1995
Baths:
2.00
MLS#:
1006073456
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

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

Type:
Single Family
Sq.Ft.:
1,424
Status:
Active
Beds:
3
Lot size:
1 Acres
Year built:
1920
Baths:
2.00
MLS#:
1005610694
Subdivision:
Gerogetown

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
1,762
Status:
Active
Beds:
2
Lot size:
0.17 Acres
Year built:
1900
Baths:
2.00
MLS#:
1005610732
Subdivision:
None

ADDITIONAL INFORMATION

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

Type:
Single Family
Sq.Ft.:
2,055
Status:
Active
Beds:
3
Lot size:
0.57 Acres
Year built:
1974
Baths:
2.00
MLS#:
1004251654
Subdivision:
Sarah Skipper Lands

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
n/a
Status:
Active
Beds:
4
Lot size:
1.9 Acres
Year built:
1990
Baths:
3.00
MLS#:
1002400784
Subdivision:
Reba L Anthony Subdivision

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
1,624
Status:
Active
Beds:
4
Lot size:
0.34 Acres
Year built:
2004
Baths:
3.00
MLS#:
1002775292
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

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!

Type:
Single Family
Sq.Ft.:
1,808
Status:
Active
Beds:
2
Lot size:
7.89 Acres
Year built:
1981
Baths:
3.00
MLS#:
1002358568
Subdivision:
Just Outside Chestertown

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
1,782
Status:
Active
Beds:
3
Lot size:
0.37 Acres
Year built:
1943
Baths:
2.00
MLS#:
1002357276
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
n/a
Status:
Active
Beds:
3
Lot size:
0.44 Acres
Year built:
1980
Baths:
3.00
MLS#:
1002352414
Subdivision:
Mile Tree Village

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
n/a
Status:
Active
Beds:
4
Lot size:
0.38 Acres
Year built:
1984
Baths:
3.00
MLS#:
1002335762
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
2,437
Status:
Active
Beds:
3
Lot size:
1.84 Acres
Year built:
1986
Baths:
2.00
MLS#:
1002276762
Subdivision:
Langford Bay Estates

ADDITIONAL INFORMATION

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.

Type:
Single Family
Sq.Ft.:
n/a
Status:
Active
Beds:
3
Lot size:
1.45 Acres
Year built:
2005
Baths:
3.00
MLS#:
1002304002
Subdivision:
None

ADDITIONAL INFORMATION

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.

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1–25 of 116 properties displayed
Joe Quinn, Maryland License 6089, Xome Inc., License 6089, Joe.Quinn@Xome.com, 844-400-XOME (9663), 300 East Lombard Street, Suite 840, Baltimore, MD 21202
Joe Quinn, D.C. License PB98375891, Xome Inc., License CO98372739, Joe.Quinn@Xome.com, 844-400- 9663, 300 E. Lombard St., Suite 840, Baltimore, MD 21202
Thomas H. O’Leary, PA License #RM423918, Xome Inc., PA License #RB067821, ThomasH.OLeary@Xome.com, 844-400-XOME (9663) 3200 Park Center Drive, 15th Floor, Costa Mesa, CA 92626
Thomas H. O'Leary, NJ License # 1754747, Xome Inc. NJ License # 1861285, ThomasH.OLeary@Xome.com, 844-400-XOME (9663), 3200 Park Center Drive, 15th Floor, Costa Mesa, CA 92626

© BRIGHT, All Rights Reserved - 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 Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. 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. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

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