Chestertown MD Real Estate & Homes for Sale

The median home value in Chestertown, MD is $223,000. 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 Chestertown, MD is $223,000. 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.:
1,923
Status:
NEW LISTING
Beds:
2
Lot size:
0.12 Acres
Year built:
1900
Baths:
3.00
MLS#:
MDKE100198
Subdivision:
Chestertown In Town

ADDITIONAL INFORMATION

Type:
Single Family
Sq.Ft.:
1,136
Status:
NEW LISTING
Beds:
3
Lot size:
0.07 Acres
Year built:
1992
Baths:
2.00
MLS#:
MDKE100150
Subdivision:
None Available

ADDITIONAL INFORMATION

Live in town as personal residence or continue renting to current or future tenant(s) as investment. Located well for access to all Town conveniences. Large level fully fenced yard that wraps two sides of house.

Type:
Single Family
Sq.Ft.:
952
Status:
Active
Beds:
3
Lot size:
0.5 Acres
Year built:
1900
Baths:
1.00
MLS#:
MDKE100034
Subdivision:
None-Available

ADDITIONAL INFORMATION

House that needs complete renovation on half acre with public water and sewer hooked up. Sold "As Is".

Open House:

Saturday, 11/24 2:00-5:00PM

Type:
Single Family
Sq.Ft.:
2,600
Status:
Active
Beds:
5
Lot size:
0.56 Acres
Year built:
1998
Baths:
3.00
MLS#:
1009979876
Subdivision:
Crestview

ADDITIONAL INFORMATION

Exhale and enjoy a one level living lifestyle near Downtown Chestertown. With 5 bedrooms total, this home offers all pocket doors and an in-law suite with a handicap accessible master bathroom. The other side of the home sits a master bedroom w/ on-suite and 3 other bedrooms. Freshly painted, move in ready with an updated kitchen with newer stainless steel appliances, granite countertop and a large pantry. The oversized garage allows for small boat storage, ATV's or other fun toys. Bring the outdoors in with two sliders, extending the family room onto the screened porch and back yard.

Type:
Farm
Sq.Ft.:
5,190
Status:
Active
Beds:
5
Lot size:
76.07 Acres
Year built:
1800
Baths:
6.00
MLS#:
MDKE100018
Subdivision:
None

ADDITIONAL INFORMATION

A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in the 90's. Providence Plantation defines Country Elegance with a fabulous 1st flr MBR suite, a new 3BR tenant house, dock with lift & an in-ground pool. A 3rd home may be built to create a family compound. Enjoy the peace and serenity of Eastern Shore outdoor Life. Agent/Owner.

Type:
Single Family
Sq.Ft.:
2,040
Status:
Active
Beds:
3
Lot size:
0.25 Acres
Year built:
1900
Baths:
2.00
MLS#:
1010003886
Subdivision:
Chestertown

ADDITIONAL INFORMATION

A true diamond in the rough. Everyone loves a swing on a front porch, it always brings such a welcoming feel and looks so inviting to take a few minutes to relax on. Then into the open foyer with a beautiful stair case that leads to the 3rd floor. Pocket door from parlor to dining area is in wonderful condition. Original trim and molding that you will want to keep for sure. Hardwood flooring is in good condition, light refinish would do the trick . Original doors that are in gorgeous condition with original hardware. This home is ready for renovation with so much good to offer that gives this home so much of its character. Selling As IS.

Type:
Single Family
Sq.Ft.:
1,057
Status:
Active
Beds:
3
Lot size:
0.07 Acres
Year built:
1946
Baths:
1.00
MLS#:
MDKE100008
Subdivision:
None

ADDITIONAL INFORMATION

Adorable bungalow in downtown Chestertown. Walk to shops, restaurants and the Chester River! Sold AS IS.

Type:
Single Family
Sq.Ft.:
n/a
Status:
Active
Beds:
6
Lot size:
76.07 Acres
Year built:
1782
Baths:
6.00
MLS#:
MDKE100016
Subdivision:
None

ADDITIONAL INFORMATION

A quintessential 76-acre Eastern Shore waterfront estate built in 1781 & restored in the 90's. Providence Plantation defines Country Elegance with a fabulous 1st floor master bedroom suite, a new 3 BR Tenant House, dock with lift and an in-ground pool. A 3rd home may be built to create a family compound. Enjoy the peace and serenity of the Eastern Shore outdoor life. Owner is Licensed Real Estate Agent.

Type:
Single Family
Sq.Ft.:
1,867
Status:
Active
Beds:
3
Lot size:
0.46 Acres
Year built:
2004
Baths:
2.00
MLS#:
1009970936
Subdivision:
Kingstowne Manor

ADDITIONAL INFORMATION

Move-in ready home in Queen Anne's County, but just a few minutes from Downtown Chestertown! Offering new carpets, paint and landscaping. Desirable split bedroom, single level living floor plan. Large Master suite offers walk in closet and great Master bath with tiled floors, double vanity, separate shower and corner soaking tub! Two additional bedrooms share a full bath with tiled floors. Large kitchen/breakfast area with stone tile floors and wood cabinets opens to screened porch. Open family room with propane fireplace for chilly Fall nights. Separate formal dining room or office space. Oversize 2-car garage and a fully fenced rear yard round out the total package.

Type:
Single Family
Sq.Ft.:
1,548
Status:
Active
Beds:
3
Lot size:
0.03 Acres
Year built:
2008
Baths:
3.00
MLS#:
MDKE100000
Subdivision:
None Available

ADDITIONAL INFORMATION

Pretty townhome in a four unit building. Very clean, looks brand new. Stainless appliances, a full dry basement with inside access. Sprinkler system, wood floors, community pond with a soothing fountain feature, gazebo. No maintenance. HOA is 150/quarterly. Gorgeous light with loads of windows. Granite countertops, open kitchen/living room with a breakfast bar.

Type:
Single Family
Sq.Ft.:
800
Status:
Active
Beds:
4
Lot size:
0.69 Acres
Year built:
2004
Baths:
3.00
MLS#:
1010004222
Subdivision:
Coventry Farms

ADDITIONAL INFORMATION

This home shows like a model! Wonderful floor plan makes it a delight and great for entertaining! Gleaming Hardwood floors, vaulted ceilings, upgraded cabinetry throughout. Gourmet kitchen with gas double oven and stainless steel appliances. Great room has lovely views of rear yard and woods and a nice balcony off it. Current owner finished basement with Family Room and bar, a fabulous full bathroom and a bonus room that is currently used as a spare bedroom. Well maintained home ready for your quick settlement!

Type:
Single Family
Sq.Ft.:
2,500
Status:
Active
Beds:
3
Lot size:
6 Acres
Year built:
1989
Baths:
3.00
MLS#:
1010003642
Subdivision:
Waterfield

ADDITIONAL INFORMATION

A country treasure located just outside of Chestertown on 6 open acres with views of 4 acre waterfowl pond. Spacious home with lots of desirable features. Room for animals, hobby crops, a pool, or whatever you want. Recent roof replacement and brand new well. Metal shop building with tractor shed attached. The possibilities are endless!

Type:
Single Family
Sq.Ft.:
5,563
Status:
Active
Beds:
5
Lot size:
21.06 Acres
Year built:
2005
Baths:
4.00
MLS#:
1009997800
Subdivision:
21 Private Acres

ADDITIONAL INFORMATION

Over 21 Acres Ready for your Horses & Existing Vineyard- Possible B&B! Entertainer's Delight- Nearly 5600 sq ft, 5 Bedrooms, 3.5 Baths. In-Ground Pool, Large Patio. Fenced Pasture. Large Outbuilding with 2 Stalls, Main-Level Master Suite w/ ADDITIONAL Potential In-Law Bedroom/Rec Room w/ Access to 1/2 Bath & Washer/Dryer, 3- Car Side-Load Garage,. 3 LARGE upper-level Bedrooms!

Type:
Single Family
Sq.Ft.:
2,114
Status:
Active
Beds:
4
Lot size:
0.1 Acres
Year built:
1884
Baths:
3.00
MLS#:
1009954076
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

Iconic Mill Street home, this "Folk Victorian" has been lovingly maintained & thoughtfully upgraded while maintaining the historic features: refinished Heart Pine flooring throughout, crown moulding, chair rails, built-in shelving, & an extra-long claw foot soaking tub . Upgrades include high-velocity HVAC, blown-in insulation (walls, attic, & cellar), granite counters & new cabinetry in the kitchen, tiled bathrooms, dressing room off the Master bedroom with a walk-in closet, & encapsulated cellar. The backyard oasis is private, quiet, & low-maintenance; seasonal trees & plants bloom three seasons of the year. The garden shed & shop is tucked away, but offers great storage & work space. Situated in the heart of Downtown Chestertown, take a peek at this home soon!

Type:
Single Family
Sq.Ft.:
960
Status:
Active
Beds:
3
Lot size:
0.52 Acres
Year built:
1965
Baths:
1.00
MLS#:
1009949688
Subdivision:
Washington Park

ADDITIONAL INFORMATION

Remodeled rancher in Chestertown. New, eat-in kitchen with granite counters, stainless appliances. Hardwood floors. Tile bath. New carpet. Recessed lighting in living room and kitchen. New HVAC, New wiring,plumbing, Large lot. Great home for the price. Just move in.

Type:
Single Family
Sq.Ft.:
1,404
Status:
Active
Beds:
3
Lot size:
0.47 Acres
Year built:
2005
Baths:
2.00
MLS#:
1009958372
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

Dutch colonial in water privileged community with docks and boat ramp close to marina. Nice size rooms, first floor bedroom, deck off Dining Room. Large lot. Home is in excellent condition - like new.

Type:
Single Family
Sq.Ft.:
768
Status:
Active
Beds:
2
Lot size:
0.09 Acres
Year built:
1949
Baths:
1.00
MLS#:
1009957738
Subdivision:
Calvert Homes

ADDITIONAL INFORMATION

Affordable home beautifully and thoroughly renovated in 2015 with new roof, kitchen, windows, bathroom, range, dishwasher, washer & dryer. You could own this home for LESS than $950/mo and this INCLUDES taxes & insurance. This is a must see to appreciate everything this house has to offer including the front porch, rear deck and completely fenced yard. TENANT OCCUPIED so please allow 24 hour notice. Investor Buyers - Tenant would like to stay if possible!

Type:
Single Family
Sq.Ft.:
10,870
Status:
Active
Beds:
5
Lot size:
300 Acres
Year built:
1990
Baths:
6.00
MLS#:
1009942958
Subdivision:
Chestertown

ADDITIONAL INFORMATION

300+/- acre waterfront estate with exceptional amenities. Main house with 7,500+/- sq ft, with a retreat feel and open floor plan. Indoor and outdoor pools, high elevation and expansive southern and western views down coveted West Fork Langford Creek. Boat house with 7'+.- MLW, tenant house, historic farm house, antique covered bridge, large barn, waterfowl ponds and 1.5+/- miles of shoreline.

Type:
Single Family
Sq.Ft.:
1,500
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1989
Baths:
2.00
MLS#:
1009933688
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

Deeply Discounted Foreclosure Opportunity in Chester Harbor. Property was previously renovated/updated. Large, clean rancher w/ addition in need of TLC. Sold Subject to ground rent if existing seller will not redeem. Assignment of a bank foreclosure, special papers needed for offer. Contact LA. Sold as-is cash or hard money . Conventional w/ 20% down possible. NO FHA . Seller does not guarantee accuracy in this listing, buyer/agent to verify.

Type:
Single Family
Sq.Ft.:
3,128
Status:
Active
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:
Active
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:
Active
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

OPEN SAT, 27TH, 12-2 PM! AMAZING CUSTOM-BUILT ESTATE sited on almost 14 acres w/Every luxury & upgrade + 2500 sf basement. First floor master, 4 addtnl Brs, Phenomenal kitchen includes 3 ovens, double dishwasher, granite counters, custom Amish lighted, glass cab., custom tile floors, double sinks + veg sink, conv. micro, table space, serving counter, desk area. STUNNING wall of glass & two-story brick FIREPLACE in open family room w/balcony overlook. HUGE screened porch w/vaulted ceiling & brick floor. Amazing brick front porch w/entertainment area to capture every country view! IT'S WORTH A LOOK; YOU'LL FALL IN LOVE!

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. Clothes dryer, water softener and microwave are not in working order. Possible investment opportunity.

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1–25 of 110 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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