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Chestertown MD Real Estate & Homes for Sale

57 Properties Found

The median home value in Chestertown, MD is $259,700. This is higher than the county median home value of $178,000. The national median home value is $277,796. The average price of homes sold in Chestertown, MD is $259,700. Approximately 44% of Chestertown homes are owned, compared to 42% rented, while 14% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you like to see a property, contact Chestertown real estate agent to arrange a tour today!
Learn more about Chestertown Real Estate.


1–25 of 57 properties displayed
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Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,426
Status:
NEW LISTING
MLS#:
MDQA2000578
Type:
Single Family, Single Family-Detached
Subdivision:
Church Meadow
Lot size:
1.25 Acres
Year built:
2014
Courtesy: CR Realty
View additional info
Beds:
3
Baths:
3 Full
Sq.Ft.:
1,944
Status:
NEW LISTING
MLS#:
MDQA2000594
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
8.96 Acres
Year built:
1986
Courtesy: Riverview Realty, LLC.
View additional info

Cape Cod on secluded 8.9 acre wooded site minutes from historic Chestertown. Large detached garage, screened porch, deck, above ground pool, fenced yard.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,616
Status:
NEW LISTING
MLS#:
MDKE2000260
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.3 Acres
Year built:
1955
Courtesy: Coldwell Banker Realty
View additional info

Charming Brick Home: This lovely home is located withing walking distance to Washington College and downtown Historic Chestertown. Here are just a few of its wonderful features: updated kitchen, spacious family room, separate dining area, wood flooring, central a/c. Enjoy the delightful side porch, lovely landscaping and mature trees. A great value for this home in sought-after College Heights. Seller has requested that all offers be submitted no later then Tuesday August 3rd by 1 PM.

Beds:
4
Baths:
3 Full
Sq.Ft.:
3,806
Status:
NEW LISTING
MLS#:
MDKE2000180
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester
Lot size:
0.6 Acres
Year built:
2013
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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This Wilson Taylor built home offers privacy and country quiet in the water privilege community of Tolchester. It is in excellent condition and a new bathroom was just added. On the first floor there is a master bedroom and bath, second bedroom, home office or third bedroom, full bath, laundry, kitchen with living/dinning combo and fireplace. The second floor has a bedroom and bath and loads of room for 2 more bedrooms or family room, office, bathroom and/or storage. There is a community HOA, but it's voluntary. The Tolchester Marina and The Shanty Beach Bar are a mere 1/2 mile away. Kent County Ag Center is across the street where the 4H Fair is held. Enjoy being out of town while close to both Chestertown and Rock Hall.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,684
Status:
NEW LISTING
MLS#:
MDKE2000214
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.09 Acres
Year built:
1920
Courtesy: Cross Street Realtors LLC
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Beyond the welcoming front porch on beautiful S. Queen Street you are greeted by a gracious foyer and wide hall with recently refinished staircase. A three-windowed living room with gas fireplace connects with an equally sized dining room that readily accommodates both casual, comfortable nights home and vibrant entertaining. A conveniently positioned butlers' pantry and powder room is adjacent to the enclosed spacious kitchen with wood cabinetry and all the appliances needed for a home cooked meal. The four-season sunroom behind the kitchen overlooks the landscaped garden. The second floor is home to two bedrooms and two baths. The primary bedroom and bath also boasts a walk-in closet. A recently renovated hallway bath serves a second bedroom. Laundry with full sized appliances is also on the second floor. A full sized third floor includes two additional bedrooms. This well-maintained house has a new roof, recently upgraded HVAC for 2nd and 3rd floors, and a new hot water tank. The two car driveway has refurbished gravel and attractive ramp up to the front porch. This is the kind of home that contributes to the warmth, charm and character of historic Chestertown and inspires so many wonderful people to live here.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,708
Status:
NEW LISTING
MLS#:
MDKE2000290
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.26 Acres
Year built:
1956
Courtesy: Heroes Real Estate
View additional info

Stunning brick cape on quiet street with large yard! Gorgeous redone kitchen includes solid shaker cabinetry with soft close drawers and dovetail construction plus granite tops, subway backsplash, farmhouse sink, and brand new stainless appliances! Ship lap, exposed wood shelving, barn door in bath, wood fireplace, eng hardwood flooring, some new windows, new water heater and more! ABSOLUTE MUST SEE HOME!

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,000
Status:
NEW LISTING
MLS#:
MDKE2000132
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.18 Acres
Year built:
2001
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Water accessible community not far from Chestertown, Rock Hall, The Santy Beach Bar and all within 90 minutes of Baltimore, DC and Philadelphia! Situated on a dead end road, this home has a large deck, gas fireplace, updated countertops and freshly painted!

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,288
Status:
NEW LISTING
MLS#:
MDKE2000166
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.46 Acres
Year built:
1978
Courtesy: CENTURY 21 The Real Estate Centre
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Come and see !this Beautiful Ranch home on wooded corner lot in quiet water privileged community. The home offers three bedrooms, two baths, large eat-in kitchen, and large Family room with wood-burning stove, On Maryland's beautiful Eastern shore, conveniently located right outside of quiet Chestertown, a perfect location if youâre looking for a tranquil private setting for your next home, or your getaway vacation home. Located steps from the water, minutes from Chestertown offer, and quick access to Rt. 213 . Enjoy the convenience of nearby dining and shopping options in Middletown together with the quaint charm of a small town. You can enjoy the Beach, Boat Ramp, Club House, Common Grounds, Marina/Marina Club, Mooring Area, Picnic Area, Pier/Dock, Water/Lake Privileges Water Oriented and Water Access. HOA is Voluntary. All major systems updated in 2014 and new BAT septic system installed in 2015. All appliances stay, Move right in. Everything is on one level with a lovely screened in porch in the rear of the home.

Open House:

Saturday, 8/7 11:00-2:00PM

Beds:
3
Baths:
1 Full
Sq.Ft.:
816
Status:
NEW LISTING
MLS#:
MDKE2000148
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.46 Acres
Year built:
1963
Courtesy: Coldwell Banker Chesapeake Real Estate Company
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Completely Renovated Rancher !!! Brand new roof , brand new HVAC & plumbing system, brand new deck . Brand new everything !! This home updated in 2021 has been completed with granite countertops, stainless steel appliances, beautiful white cabinets, brand new carpets. With 3 bedrooms and 1 full bath, This home is perfect for anyone . Backing to the woods this home offers peace and tranquility with just a 5 min to the beatiful town of Chestertown. This home won't last long !!!!! Professional picutures to be uploaded 8/2

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,344
Status:
NEW LISTING
MLS#:
MDKE2000176
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.45 Acres
Year built:
1998
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Beautiful brick home in Chesapeake Landing. 3 bedrooms, 2.5 baths. Covered front porch. Covered back deck that could easily be screened in. Hardwood floor in great condition throughout most of the first floor. Home shows beautifully and would be perfect for a summer get-a-way or full time residence. Spacious yard, quiet street. Voluntary HOA. Water access to Worton Creek with community beach, boat ramp, picnic area and many other amenities. Rinse off after a day at the beach in the outdoor shower!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,199
Status:
NEW LISTING
MLS#:
MDKE2000216
Type:
Townhouse
Subdivision:
Hill Top
Lot size:
0.05 Acres
Year built:
2005
Courtesy: Rock Hall Properties Real Estate
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Welcome to 304 Hilltop! This original owner has meticulously maintained and upgraded the home with new dual-zone HVAC (2020), Corian kitchen countertops and tile backsplash (2019), 13' x 19' stamped concrete rear patio, newer primary bath shower surround and much more. Annual roof and siding power washing make this home clean inside and out! The new energy efficient HVAC system keeps the total electric bills less than $150 per month average. Low cost of ownership make this an attractive, affordable home that's within walking or bicycling distance to downtown Chestertown.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,212
Status:
NEW LISTING
MLS#:
MDKE2000238
Type:
Single Family, Single Family-Detached
Subdivision:
Washington Park
Lot size:
0.6 Acres
Year built:
1966
Courtesy: Doug Ashley Realtors, LLC
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Cute rancher with wood floors through most of this home. Replacement windows and a family room addition make this an amazing value. Propane gas forced air heat and window A/C units to help heat and cool. Located near the end of a dead end street. Great backyard that backs to woods. Has a security system. If you are looking for a great community setting then this home may be for you!!

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,680
Status:
Active
MLS#:
MDQA2000342
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.46 Acres
Year built:
1991
Courtesy: RE/MAX Executive
View additional info

This Country Cape Cod is located near the Chester River on 1/2 acre lot. Lots of room for a garden. Deck off the back gives excellent outdoor entertaining space. This 4 bedroom, two bath home is move in ready. The garage area has been converted to business space but could be converted back to a garage space, workshop or family room, heat and air are already in place. Pull down stairs lead to amazing space above the garage for storage or convert to additional living space. Large kitchen with breakfast bar and table space flow nicely into the living room. Two bedrooms on the first floor along with a hall guest bathroom. Upstairs your will find two large bedrooms and bath. Need more living space? Covert the space above the garage...envision a master suite with walk in closet and bath or finish as an additional bedroom, playroom, study or den. Got a golf cart? It's just a short ride to the water for fishing, boating or playing. Large paved driveway can accommodate cars, trucks, campers, trailers and more. Just a few mins to downtown Chestertown for shopping and dining. Shore living at it's best.

Beds:
4
Baths:
3 Full
Sq.Ft.:
1,756
Status:
Active
MLS#:
MDKE2000200
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.37 Acres
Year built:
1970
Courtesy: Doug Ashley Realtors, LLC
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This home has been renovated top to bottom in recent years. Gleaming wood floors are throughout most of the main level. The kitchen/dining area combination has a slider that exits to the rear deck. The lower level offers two very spacious rooms that act as family and rec rooms. There is even a bedroom on the lower level and a separate full bath. Sliders in lower level take you to the patio under the deck and to the nice semi-private backyard. Freshly painted and ready for you just to move right in!!!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,400
Status:
Active
MLS#:
MDKE2000194
Type:
Condo
Subdivision:
Chester River Landing
Year built:
2009
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

You will appreciate peaceful living in this waterfront community on the Chester River just minutes from historic Chestertown.. A light-filled and spacious open floor plan is wonderful for enjoying the elegant interior amenities. You will also want to sun bathe or swim at the lovely pool, stroll the shell walking paths throughout the community and along the shoreline, go kayaking from the community dock, or just sit back and relax while enjoying the Eastern Shore lifestyle.

Beds:
2
Baths:
1 Full
Sq.Ft.:
928
Status:
Active
MLS#:
MDKE2000190
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.1 Acres
Year built:
1900
Courtesy: Gunther-McClary Real Estate
View additional info

Clean and very well maintained property! Turn key opportunity that can be occupied by you or rented to tenants. The house was remodeled in 2011 and has had great rental history. It is not far from downtown Historic Chestertown, MD. Access to Rails-to-Trails right in your back yard and leads to Wilmer Park on the Chester River.

Beds:
4
Baths:
3 Full/2 Half
Sq.Ft.:
5,595
Status:
Active
MLS#:
MDKE2000196
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
21.07 Acres
Year built:
2002
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Just reduced! Complete privacy surrounds this stunning waterfront farmette on the east fork of Langford Creek featuring 21 picturesque acres. Custom built home features 1 gigabyte high speed internet , grand entryway leading into a center hall, wide halls, arched doorways, formal living room, dining room, library, breakfast room, family room. Three fireplaces have been converted to propane but could easily be switched back to wood burning. First floor owners suite with sitting room, double walk in closets, fireplace, spacious bath. Three guest bedrooms on the second floor, two with en suite baths. Office on second floor could be converted into another bedroom. Large gourmet kitchen with high end appliances. Many other amenities to include a screened in porch, 3 car attached garage, unfinished basement, large indoor pool, 3 zones for heat/AC, central vacuum, and whole house generator. Do not enter property without listing agent. No drive-bys. Video monitored. Please schedule appointment.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,366
Status:
Active
MLS#:
MDKE2000082
Type:
Condo
Subdivision:
Riverside Terrace
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Cute as a button! This two bedroom one bath condo is just a short walk to the Chester River. The home in neat and tidy and all that you need for a weekend getaway or full time residence. There is no grass to mow as the front yard is a perennial garden and the back is a brick courtyard with a privacy fence. Loaded with charm and character. The bathroom has been updated. Walking distance to everything Chestertown has to offer!

Beds:
4
Baths:
4 Full/1 Half
Sq.Ft.:
6,050
Status:
Active
MLS#:
MDKE2000022
Type:
Single Family, Single Family-Detached
Subdivision:
Broad Neck
Lot size:
26 Acres
Year built:
1952
Courtesy: Cross Street Realtors LLC
View additional info

Private but not remote. Spacious yet intimate. Thoughtfully designed and comfortable. The main house embraces the ever changing water vistas of Horner Cove and Langford Creek from every room, with the beautiful Chester River only minutes away. The two guest cottages are quaint, rustic and charming. Ownership of Honest Point Farm, its' 26 acres and spacious main residence only makes sense if a multi-faceted lifestyle is desired: swimming, boating of all kinds, bird watching (including resident osprey), fishing, picking of fruit and making of jams, gardening and perhaps tending bees, indoor and outdoor cooking and dining, children playing within eyesight, family and guests enjoying themselves and finding a comfortable spot to relax, read and nap away from others if desired....... Entering the front door, a large living room with wood fireplace quickly accommodates guests. A library, bedroom and bath are beyond and can be used together as a primary or very generous guest suite. A large screened porch is accessed from the library with wood stove and built in book cases. The dining room with picture window and discreetly hidden wet bar connects the living room and recently added addition that features one of the finest modern kitchens and entertainment spaces on the Eastern Shore. Sliding doors provide immediate access to a large deck and a path to the swimming pool. A large pantry/mudroom is immediately off the kitchen. A long breezeway overlooking side gardens connects the house with the new two-car garage (with 240V to charge your electric car). In cooler months, the breezeway is the perfect spot to bring inside your potted lime and lemon trees, and other summer plants. The second floor houses three spacious bedrooms each with beautiful bathrooms. A laundry room with linen storage and a bonus room currently used for exercise and hobbies/gift wrapping space is at the end of the hallway. Raised garden beds, an orchard of apple, sour cherry, figs and quince trees, bee apiary, play house and sand box, swimming pool, boat dock, screened porch, large shaded deck and walking paths provided an unlimited outdoor lifestyle. Property well maintained. Kitchen and garage built in 2017. Fiber optic internet. Whole house generator. New storm windows. All bathrooms and laundry upgraded in 2019-2020. Refreshed bulkhead. Guest cottages also enjoy some upgrades. Current owners have allowed select friends and neighbors to hunt in season, as permitted by law.

Open House:

Saturday, 8/7 11:00-1:00PM

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,416
Status:
Active
MLS#:
MDQA2000318
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.36 Acres
Year built:
1946
Courtesy: Doug Ashley Realtors, LLC
View additional info

Cute home with two bedrooms on the main level one upstairs with a bonus area, two bath's, one on each level. Beautiful wood flooring, fireplace, and updated kitchen. There is a nice screened porch, in a shady location. One of trees is a beautiful seedling from the Wye Oak. We have the paperwork to pass on to the new owner. It's a beautifully landscaped corner lot with a detached garage. Partial basement and a crawl space room for a work area, and while laundry is downstairs, it would not be hard to move the laundry to the first level. Easy to show..

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
1,029
Status:
Active
MLS#:
MDKE2000170
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.16 Acres
Year built:
1920
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Home needs some updating but very live able. Being sold AS-IS. (As-is addendum required) Lots of potential, close to downtown Chestertown, Washington College and the Chester River. Listing is about location and lot. Seller is a licensed Real Estate Agent.

Beds:
1
Baths:
1 Full
Sq.Ft.:
884
Status:
Active
MLS#:
MDKE2000110
Type:
Single Family
Subdivision:
Historic District Chestertown
Lot size:
0.05 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

Life in Historic downtown Chestertown is a life of charm and ease. Easy proximity to stores, including a health food stores, restaurants, library, art galleries, adorable boutiques and the Chester River! There is so much to enjoy in Chestertown, it's almost a life on permanent vacation. This property is part of a duplex, and the owner would prefer to sell both units at one time. Live in this one, and rehab the other one. This unit has been a rental for years, is in great condition, and shows well. Call us for more information.

Beds:
1
Baths:
1 Full
Sq.Ft.:
950
Status:
Active
MLS#:
MDKE2000112
Type:
Single Family
Subdivision:
Historic District Chestertown
Lot size:
0.04 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

This property would benefit from TLC, but the potential is there and the structure is solid. Owner owns the other side of the duplex and rehabbed it and has used it as a rental. Owner prefers to sell both units at one time.

Beds:
1
Baths:
1 Full
Sq.Ft.:
600
Status:
Active
MLS#:
MDQA2000234
Type:
Single Family, Single Family-Detached
Subdivision:
Kingstown
Lot size:
0.34 Acres
Year built:
1945
Courtesy: EShore
View additional info

Waterfront Lot with dilapidated residence. Existing well and septic.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,861
Status:
Active
MLS#:
MDQA148184
Type:
Single Family, Single Family-Detached
Subdivision:
Evergreen Manor
Lot size:
0.46 Acres
Year built:
2004
Courtesy: Coldwell Banker Waterman Realty
View additional info

Rare find on the Queen Anne's County side of Chestertown! You 'll be delighted with this beautiful spacious light filled home! Located on a quiet Cul-de-sac with over 3,000 square feet of finished living space. Tax records do not reflect the correct finished square feet of space!! Open concept Living features soaring vaulted ceilings and a gorgeous stacked stone fireplace in the Living room. Fireplace has been outfitted with a wood burning stove for efficiency and added heat for the house. Hardwood floors bring warmth and beauty to the main level. Kitchen is spacious and outfitted with stainless steel appliances , all appliances are less than four years old and stove is brand new! Granite counters, under cabinet lighting and decorative tile backsplash. There is a separate Wine bar with Granite counter, seating and storage! The laundry is just off the Kitchen and provides additional pantry storage, cabinets and wine racks! An eat in breakfast area holds a table large enough for six! This is an entertaining dream! Open floor plan flows into the Living room and through to the Den or can be a Formal dining area... Make it suit your needs! The Large cabinet bookcase is included in the sale! Main Level Primary Bedroom suite! Primary bedroom is filled with light and has door out to the rear deck and hot tub for your enjoyment! Spacious primary bath has separate tub and shower stall. Large walk in closet holds all your clothes with ease! Upstairs find 3 large bedrooms with spacious closets and ceiling fans. Upper level bonus room /office with vaulted ceilings, fan and attached 3 piece bathroom! All new carpet on the entire upper level and Fresh paint in most rooms! Jack and Jill bath for convenience serves the upper bedrooms. Dramatic catwalk balcony overlooks the main living area! Did I mention the basement? Also a rare find, there is an additional 1300 square feet of room down below! Walls in basement are sealed , A large workshop with storage and cabinets will be included and has stairs and bulkhead doors to the backyard! a few extra bits... House has been wired for "Smart Home " use! Rough in plumbing exists in the basement for a bathroom! Washer and dryer only 3 years young! Home has on demand tankless hot water system! Central Vacuum system! Brand new Water Softener system! Outdoors you will find a spectacular summer paradise featuring a large above ground pool, spacious deck and hot tub! The .46 Acres has a fully fenced backyard and mature landscaping across the front yard. Plenty of pictures here for you to enjoy and see how this spacious home can fulfill all your needs! A home warranty will be provided to the buyers of this well loved home to ensure it's next owners are well cared for! Call for your showing today!

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