Chestertown MD Real Estate & Homes for Sale

The median home value in Chestertown, MD is $257,900. 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 $257,900. 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-Detached
Sq.Ft.:
1,865
Status:
NEW LISTING
Beds:
3
Lot size:
1.79 Acres
Year built:
1951
Baths:
2.00
MLS#:
MDQA144692
Subdivision:
None Available

ADDITIONAL INFORMATION

Enjoy sunsets from the screened in porch and fires in the winter with one story living on the Chester River. Close to Chestertown on the Queen Anne's side. Large yard, shed, beach along 210 feet of waterfront. Pier with boat lift. A private paradise.

Type:
Single Family-Detached
Sq.Ft.:
3,248
Status:
NEW LISTING
Beds:
3
Lot size:
35.76 Acres
Year built:
1856
Baths:
4.00
MLS#:
MDKE116774
Subdivision:
None Available

ADDITIONAL INFORMATION

Middle Plantation Circa 1856, better known as Running Fox Farm, is one of the finest hunting farms in Kent County, Maryland - abundant deer, Canada and Snow geese, dove and turkey. The residence has been meticulously renovated, an extensive, well-documented project that includes upgrades such as 400 amp electric service and wiring, updated plumbing, custom restorations true to the period, and more. 213 acres with 166.6 prime soils, 60.5acres in CRP... all on FIVE 30+ acre subdivided, perc-approved lots.

Type:
Single Family-Detached
Sq.Ft.:
1,176
Status:
NEW LISTING
Beds:
3
Lot size:
0.47 Acres
Year built:
1998
Baths:
1.00
MLS#:
MDKE116918
Subdivision:
Washington Park

ADDITIONAL INFORMATION

Charming 3 br 1 bath home boasting a new roof in 2017. Updated kitchen in 2018. Newer/new laminate floors through most of the house. A 10 x 12 deck off the back has a very relaxing view. The view out the front is that of the community park. This is a great starter home, great for a young family, and a great place to retire.

Type:
Single Family-Detached
Sq.Ft.:
3,303
Status:
NEW LISTING
Beds:
4
Lot size:
1.68 Acres
Year built:
1989
Baths:
5.00
MLS#:
MDKE116830
Subdivision:
Heather Heights

ADDITIONAL INFORMATION

Chester River water views await you from this sprawling ,brick ranch-style home close to Downtown Chestertown. Situated on a double lot with 1.68 acres this beautiful home offers a flexible 3 or 4 bedrooms, 3 full baths, a large kitchen with island, a 4-season sun room, and a gorgeous living room with gas fireplace and stunning bay window. Come enjoy all the area has to offer with amazing art, great shopping and food, golf, boating, all the best of Eastern Shore life!

Type:
Single Family-Detached
Sq.Ft.:
888
Status:
NEW LISTING
Beds:
3
Lot size:
0.35 Acres
Year built:
1964
Baths:
1.00
MLS#:
MDKE116894
Subdivision:
Quaker Estates

ADDITIONAL INFORMATION

GREAT INVESTMENT OPPORTUJITY.....home has new siding and windows and is served with public sewer.Home needs some work

Type:
Single Family
Sq.Ft.:
1,393
Status:
NEW LISTING
Beds:
3
Lot size:
0.07 Acres
Year built:
2015
Baths:
3.00
MLS#:
MDKE116906
Subdivision:
Chester River Landing

ADDITIONAL INFORMATION

Welcome to 114 Landing Lane in the Chester River Landing community located on the Chester River in historic Chestertown Maryland.This beautiful 3 Bedroom, 2.5 Bath home is awaiting it's next owner. Feel the pride of ownership in this home from the hardwood flooring, to the upgraded gourmet kitchen. The large great room featuring a gas fueled fireplace and large windows to allow in the natural light, situated just off the kitchen is a wonderful area to relax, read or just gather with family and friends. The second level of the home features an area that can be utilized as a den or large office. Proceed another half level upstairs to an expansive family room with dining area, 2 additional bedrooms and another full bath. There are two large rear decks on this home, one off the kitchen on the main level and a second off the family room on the second level. Enjoy the views of the Chester River from the 2nd level deck. Be advised that the tax record is showing an incorrect square footage on the home, the actual square footage is over 2300 sq. ft.

Type:
Single Family-Detached
Sq.Ft.:
2,376
Status:
NEW LISTING
Beds:
5
Lot size:
0.69 Acres
Year built:
1990
Baths:
3.00
MLS#:
MDKE116904
Subdivision:
Crestview

ADDITIONAL INFORMATION

Welcome to Crestview! Located right outside of town and just minutes to Downtown Chestertown! This 5 bed, 3 bath home is nicely situated on a corner lot w/ mature landscaping & at the beginning of a Cul-De-Sac! Granite counter tops, gas fireplace and 2 master bedrooms (one on the 1st floor) are just some of the amazing things this home has to offer. Solar panels are about 5 years into the lease and save the homeowner a bundle in electric! A home inspection was completed and seller is willing to share after an offer is made, saving the buyer costs in inspections!

Type:
Single Family-Detached
Sq.Ft.:
1,690
Status:
NEW LISTING
Beds:
3
Lot size:
0.45 Acres
Year built:
2001
Baths:
2.00
MLS#:
MDQA144792
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

Lovely 3 bedroom, 2 bath Cape Cod in Chester Harbor. Situated on a large, very private lot with mature trees and super charming, expansive back yard. Nestled in near Rosin Creek this home is a walk to the community beach, convenient to Historic Chestertown, as well as, easy commute to metropolitan hubs. Perfect work from home spot! The home features, upgraded appliances, built in cabinets, hard wood flooring, spacious garage, main level bedroom and more!

Type:
Townhouse
Sq.Ft.:
975
Status:
Active
Beds:
2
Lot size:
0.01 Acres
Year built:
1900
Baths:
2.00
MLS#:
MDKE116792
Subdivision:
Vicker's Row

ADDITIONAL INFORMATION

Pristine end unit townhouse located in Vicker's Row with fresh paint throughout! Two bedrooms, 1 1/2 baths, gorgeous hardwood floors throughout. Private rear deck with extra storage and off street parking! Newer roof & HVAC system! Enjoy minimal maintenance living within walking distance to the farmer's market, downtown shopping, restaurants, galleries, the Chester River and Washington College.

Type:
Single Family-Detached
Sq.Ft.:
3,237
Status:
Active
Beds:
4
Lot size:
0.66 Acres
Year built:
1860
Baths:
6.00
MLS#:
MDKE116878
Subdivision:
Historic Chestertown

ADDITIONAL INFORMATION

Welcome to the historic John . Stam house, the only "A-rated" Victorian in Chestertown according to the Secretary of the Interior. This property has so much to offer. A Gothic Revival Victorian with painted fire places, a double parlor with pocket doors, and entrance hall. Features such as hand painted plastered ceilings, Jenny doors, and original medallions, make this a one of a kind home. Dado chair rail and paneling, Bradbury and Bradbury Art Wallpapers, Soapstone fireplaces, China closet, and the list goes on. The details are such that the property really needs to be seen to be appreciated. Kitchen is completely upgraded with Delohghi stove and sub zero refrigerator. Waterfall in the back yard with gracious gardens make for a charming outdoor oasis. "Carriage slate "architectural shingle roof. Currently run as a bed and breakfast. Additional buildable lot at the rear of the property included in the sale. Driveway with 6-8 parking spaces makes hosting guests easy.

Type:
Single Family-Detached
Sq.Ft.:
2,470
Status:
Active
Beds:
3
Lot size:
1.15 Acres
Year built:
1980
Baths:
2.00
MLS#:
MDKE116826
Subdivision:
Langford Bay Estates

ADDITIONAL INFORMATION

Water view and water access home in Langford Bay Estates has something for everyone! Main-level living, a 2-car attached garage with workshop, mature landscaping, beautiful Four Season room off the back, and large living room with gas fireplace. Improvements include an additional bedroom or office off the garage, a new (2018) 20 SEER heat pump and whole house propane generator. The boat slip at the community pier is only $500 a year!

Type:
Townhouse
Sq.Ft.:
1,976
Status:
Active
Beds:
3
Lot size:
0.08 Acres
Year built:
2003
Baths:
3.00
MLS#:
MDKE116888
Subdivision:
Oakstreet

ADDITIONAL INFORMATION

Type:
Single Family-Detached
Sq.Ft.:
1,416
Status:
Active
Beds:
3
Lot size:
0.46 Acres
Year built:
1976
Baths:
1.00
MLS#:
MDQA144690
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

AFFORDABLE WATERFRONT AND PRICED TO SELL! Cozy Cottage on Rosin Creek with Floating Dock. If you are looking for that relaxing retreat, this is It! Screened porch, deck, mature trees, new roof, garden shed. Roof was replaced this year. Approximately 3 miles to Downtown Chestertown and 90 minutes to DC, Baltimore, Philadelphia, Wilmington.

Type:
Single Family-Detached
Sq.Ft.:
1,675
Status:
Active
Beds:
3
Lot size:
0.39 Acres
Year built:
1948
Baths:
2.00
MLS#:
MDKE116864
Subdivision:
Fairlee

ADDITIONAL INFORMATION

If you saw this house back in 2016 you will not believe the transformation! This home has been completely renovated. A wide porch graces the front with Craftsman style pillars. The first floor has walnut floors, an open floor plan with combination living, dining and kitchen, a main level bedroom and a laundry/storage area. The kitchen has beautiful hickory cabinets, Cambria counters and a 5 burner gas stove. The upstairs was expanded by adding dormers on the front and a shed dormer on the back allowing for two nice sized bedrooms. Hardi siding, spray foam insulation and Anderson windows are additional enhancements. Outside there is a one car garage plus a 22X36 two car garage. This property is move in ready and priced to sell!

Type:
Single Family-Detached
Sq.Ft.:
1,160
Status:
Active
Beds:
2
Lot size:
0.18 Acres
Year built:
1969
Baths:
1.00
MLS#:
MDKE116860
Subdivision:
Tolchester Estates

ADDITIONAL INFORMATION

Very unique home in Tolchester Estates with breath taking views of the Chesapeake Bay. This home has ceramic tile floors, lots of stone and tile work throughout. Stainless Steel appliances and whirl pool tub in the Master bedroom. Like I said, very unique and beautiful. Definitely a "Must See".

Type:
Single Family-Detached
Sq.Ft.:
1,834
Status:
Active
Beds:
4
Lot size:
0.34 Acres
Year built:
1965
Baths:
2.00
MLS#:
MDKE116856
Subdivision:
Byford Development

ADDITIONAL INFORMATION

Gorgeous Split Foyer in the Byford Development, that is close to EVERYTHING! This property boasts 4 Bedrooms and 2 full baths , plus a bonus room! Beautifully updated from the kitchen to the lower level. Private back yard and room for fun! Hardwood floors throughout the first level? There is a pellet stove on the lower level that will keep you warm and toasty. THIS IS A MUST SEE, WON'T LAST LONG!

Type:
Single Family-Detached
Sq.Ft.:
2,737
Status:
Active
Beds:
4
Lot size:
0.75 Acres
Year built:
1964
Baths:
4.00
MLS#:
MDKE116838
Subdivision:
Chesmar

ADDITIONAL INFORMATION

This wonderful 4 bedroom family home has plenty indoor and outdoor space for everyone. The addition of entire second floor and garage along with first floor renovations were completed in 2008. Separate suite upstairs provides privacy from rest of the family. Only minutes from Chestertown by boat or car. The community of Chesmar, located on the north side of the river provides great boating along the Chester River. The double lot gives additional privacy and space on either side. The screened-in porch houses a hot tub to relax in at night without being bothered by bugs and the balcony off the family room on the second floor offers a beautiful view of the stars and moon over the river. Lots of storage inside and out for all the toys, kayaks and water gear. Walk out to the pier, board the boat and be on the river instantly for fishing , waterskiing or to enjoy abundance of wildlife on a sunset cruise.

Type:
Single Family-Detached
Sq.Ft.:
1,144
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
2002
Baths:
2.00
MLS#:
MDKE116842
Subdivision:
Chesapeake Landing

ADDITIONAL INFORMATION

Low maintenance 3 bedroom 2 full bath ranch home in the water oriented Chesapeake Landing neighborhood. Home features ceramic tile flooring in the kitchen and bathrooms and upgraded flooring in the living room and hallway. A back deck off the eat in kitchen is great for outdoor living area. Enjoy the quiet neighborhood close to Great Oak and several other local restaurants and marinas!

Type:
Single Family-Detached
Sq.Ft.:
1,428
Status:
Active
Beds:
3
Lot size:
0.04 Acres
Year built:
1880
Baths:
2.00
MLS#:
MDKE116756
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

Type:
Single Family-Detached
Sq.Ft.:
4,492
Status:
Active
Beds:
6
Lot size:
1 Acres
Year built:
1999
Baths:
4.00
MLS#:
MDQA144706
Subdivision:
Flyway

ADDITIONAL INFORMATION

Sheeew where to start! This beautiful 6 Bed 3.5 Bath home boast nearly 4500sqft. Has a laundry list of custom features through out including Oak wood floors, wainscoting, chair railing, crown molding, custom wooden blinds and Smart blinds to name a few. Totally updated kitchen with all new stainless steel appliances, granite counters and a large eat at island. Formal dining area just off the kitchen. Large 1st floor master bedroom/bath. A deep soaking tube and walk in shower Sitting library room with built in book shelves. A large family room with a brick center piece gas fire place for entertaining. Bright sun room with sky lights over looking the large rear porch that's half covered and half open for sun shine. Heated Salt water pool offering great sun during the day and shade in the evening hours provided by mature trees. Fully fenced in rear yard for animals and privacy with large vehicle access gates. Handicap rear access ramp on the rear deck. This house comes with a full Intercom system and an ADT video security system. On demand gas Instant hot water heater for endless hot showers. Smart thermostats to keep tabs homes interior temps. Oversized side entry 2 car garage as well as a 28x43 3 Car detached garage that is insulated. There is a detailed list of all custom features/upgrades with dates upon request. Recent home appraisal at $575,000

Type:
Single Family-Detached
Sq.Ft.:
2,896
Status:
Active
Beds:
3
Lot size:
89.23 Acres
Year built:
1965
Baths:
3.00
MLS#:
MDKE116790
Subdivision:
None Available

ADDITIONAL INFORMATION

"Gliding Gander Farm" Spectacular Chesapeake Bay waterfront farm with over 1/2 mile of protected shoreline with sandy beaches. Sunrises over the ponds & Sunsets over the bay. Rockfish out your front door and ducks and geese out your back door. 117.57 acres includes two (2) 10+ acres perced waterfront lots & one (1) Bay view lot. 100 acres of highly productive Mattapex soils with 3 ponds including well service. 2900 SF residence with 3 bedrooms & 3 full bathrooms with views to the Chesapeake from every room. 40 X 80 heated metal workshop for all your toys and more. We are following the COVID-19 guidelines issued by MAR.

Type:
Single Family-Detached
Sq.Ft.:
2,896
Status:
Active
Beds:
3
Lot size:
89.23 Acres
Year built:
1965
Baths:
3.00
MLS#:
MDKE116788
Subdivision:
None Available

ADDITIONAL INFORMATION

"Gliding Gander Farm" Spectacular Chesapeake Bay waterfront farm with over 1/2 mile of protected shoreline with sandy beaches. Sunrises over the ponds & Sunsets over the bay. Rockfish out your front door and ducks and geese out your back door. 117.57 acres includes two (2) 10+ acres perced waterfront lots & one (1) Bay view lot. 100 acres of highly productive Mattapex soils with 3 ponds including well service. 2900 SF residence with 3 bedrooms & 3 full bathrooms with views to the Chesapeake from every room. 40 X 80 heated metal workshop for all your toys and more. We are following the COVID-19 guildlines issued by MAR.

Type:
Single Family-Detached
Sq.Ft.:
4,874
Status:
Active
Beds:
4
Lot size:
0.26 Acres
Year built:
2009
Baths:
3.00
MLS#:
MDKE116814
Subdivision:
Coventry Farms

ADDITIONAL INFORMATION

This BEAUTIFUL Brick front 4 bedroom 2.5 bath home boosting 4,874 SQFT +/- of living space can be yours at an AMAZING PRICE! This home is located in a well-cared for and quiet neighborhood located in Chestertown on a corner lot backing to open space for more privacy. Inside you start off by walking into a great open floor layout with a formal dining room, living room, large open kitchen with Island overlooking the sun-room and living room. Kitchen has lots of cabinet space, granite counter-tops and stainless appliances. The sun-room has a doorway off the back of house that will lead you to the large recently installed 2nd story deck that~s perfect for grilling and entertaining. As you make your way upstairs, you will find the huge master bedroom with tray ceilings, walk in closet, a large sitting-room, his and her sink, and a shower/tub! Also there are three bedrooms and a full bathroom. The full Basement is just about fully finished and has a walk out level to the back yard. Two car garage and a black top driveway. Call today before this one is SOLD!

Type:
Single Family-Detached
Sq.Ft.:
1,350
Status:
Active
Beds:
4
Lot size:
0.63 Acres
Year built:
1963
Baths:
2.00
MLS#:
MDKE116798
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

PRICE IMPROVED! Completely renovated & move-in ready. This home is just minutes from Downtown Chestertown, located in the desirable Quaker Neck area. With upgrades JUST finished... your new home is BRAND NEW! Stainless steel appliances, granite countertops, upgraded flooring, tiled bathrooms, and a master with en suite bath. All in a lovely setting with fresh landscaping. Can't ask for much more... snag it soon!

Type:
Single Family-Detached
Sq.Ft.:
1,863
Status:
Active
Beds:
4
Lot size:
0.16 Acres
Year built:
1920
Baths:
2.00
MLS#:
MDKE116816
Subdivision:
Chestertown

ADDITIONAL INFORMATION

This downtown Chestertown home has undergone a tasteful renovation to include 4 bedrooms, 2 full bathrooms, hardwood floors and an upgraded kitchen. The home offers a traditional floor plan and relaxing front porch to enjoy the summer evenings. The quiet backyard has a paver patio and shade tree further expanding the livable space. Within walking distance to the college, waterfront, restaurants, bike trails and parks, this turnkey home blends comfort and convenience.

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1–25 of 104 properties displayed
Thomas H. O’Leary, Maryland License 665968, Xome Inc., License 665968, ThomasH.OLeary@Xome.com, 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Thomas H. O’Leary, D.C. License BR98378780, Xome Inc., License CO98372739, ThomasH.OLeary@Xome.com, 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
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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