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Chestertown MD Real Estate & Homes for Sale

91 Properties Found

The median home value in Chestertown, MD is $251,200. This is higher than the county median home value of $192,000. The national median home value is $231,815. The average price of homes sold in Chestertown, MD is $251,200. Approximately 43% of Chestertown homes are owned, compared to 42% rented, while 15% 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.


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1–25 of 91 properties displayed
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Beds:
2
Baths:
2 Full/1 Half
Sq.Ft.:
1,608
Status:
NEW LISTING
MLS#:
MDKE116594
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.07 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

Unique and charming home within walking distance of downtown Chestertown and the river! Lovingly restored in 2013, the home features hardwood floors throughout, fresh paint in many rooms, a spacious screened porch and two master suites. The second floor features a spacious bedroom with a walk-in closet, a separate dressing room & laundry area next to the full bath with double vanity. The third floor features a cozy suite with bedroom, sitting area, and another full bath! From the screened porch, walk down the garden path to the incredible two story garden house. This is a rare find that can be whatever you want it to be: art studio, office, or guest quarters! Come see this wonderful home and all it has to offer!

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,952
Status:
NEW LISTING
MLS#:
MDKE116544
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
1.01 Acres
Year built:
1961
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This lovely home in Country Club Estates with a glimpse of the Chester River sits on a Prime location on the 15th fairway of the Chester River Golf and Country Club. It will delight the most demanding folks interested in comfortable living on the Eastern Shore of Maryland! The well-appointed and spacious rooms are perfect for stretching out and relaxing. Just a few minutes to entertainment and fine restaurants in downtown historic Chestertown. Energy efficient and whole-house generator. High speed internet hookup. Excellent condition and ready for you to move in.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,488
Status:
NEW LISTING
MLS#:
MDQA143998
Type:
Single Family, Single Family-Detached
Subdivision:
Kingstowne Manor
Lot size:
0.46 Acres
Year built:
1997
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Offered AS-IS and is eligible under the Freddie Mac First initiative through 4/24/2020- owner-occupant buyers and qualified non-profits. Investor offers are eligible for review after 20 days of the listing date. Brand new roof but house needs attention cash or 203k loans only.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,796
Status:
NEW LISTING
MLS#:
MDQA143988
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.6 Acres
Year built:
1978
Courtesy: Doug Ashley Realtors, LLC
View additional info

This is a rehab project, with lots of space to work with. Four bedrooms, 2 baths, kitchen, separate dining room, living room, converted 2 car garage as a rec room. Sellers put on a porch addition, but needs work. Subject to a short sale with third party approval from the mortgagor. Well & Septic . The back yard has a deck area.

Beds:
4
Baths:
2 Full
Sq.Ft.:
2,138
Status:
NEW LISTING
MLS#:
MDKE116562
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.29 Acres
Year built:
1976
Courtesy: Doug Ashley Realtors, LLC
View additional info

Lovely Cape Cod with an incredible Great Room with beamed and cathedral ceiling that overlooks a spacious deck and private backyard. There may even be hardwood flooring under the carpet on the main level however it would need to be verified. The kitchen has been updated and has a center island and marble counters and tile flooring. There are 3 bedrooms on the main level and another very large bedroom/living space and bath on the 2nd level. The living room has a gas log fireplace. The property backs up to a community walking park and dog park. Close to everything!!!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,064
Status:
NEW LISTING
MLS#:
MDKE116560
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.5 Acres
Year built:
1994
Courtesy: Doug Ashley Realtors, LLC
View additional info

Great home! Master bath updated in 2020 and kitchen was completely updated in 2016. Both are beautiful!! Wood burning fireplace in the family room, overlooking a great back yard! There is a deck, a play ground area, a privacy fence makes this even more of an oasis. There is a fire pit, grilling area, you are all set! Inside, the wood floors on the first floor, an built ins are terrific. You have an updated kitchen in 2016 with stainless steel appliances to cook in! Upstairs is a huge master suite, and three additional bedrooms. There is a study nook in the hallway, Bathrooms total 2.5, and the garage is side face entry. Come check out this home. There is NO HOA and no front footage fee. This home is in the original section of Coventry farms. Encapsulated crawl space 2010

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,028
Status:
NEW LISTING
MLS#:
MDQA143734
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.42 Acres
Year built:
1976
Courtesy: Keller Williams Flagship of Maryland
View additional info

If you can see yourself living with the serenity and slow pace that only a small-town can offer ... You fancy a location convenient and accessible to the land and waters Chesapeake Country and the sporting life that abounds ... If you can picture yourself encountering at least three different woodland creatures as you drive through the fields and forests on your drive home ... put this home on your list. Nicest home available in Chester Harbor. Large level lot is a blank canvas for you to create your own outdoor sanctuary to complement the indoor serenity. Lot offers significant buffer to neighboring homes yet not without some neighborly interaction if you desire. Turnkey: everything is brand new~ Granite countertops, stainless steel appliances, washer dryer, cabinets, ceramic tile, carpeting, paint, plumbing, water heater, AC system and so much more! All bedrooms have double closets. Exterior is freshly painted and the lot is one of the biggest in the neighborhood. Must see! renovated in 2018 with no surface left untouched. You will fall in love with this enchanting home as quickly as did its current owner.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,500
Status:
Active
MLS#:
MDKE116548
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
1.01 Acres
Year built:
2020
Courtesy: Kevin Dey Realty
View additional info

Construction Complete, Move Right In! Quality built Cape Cod on over ONE ACRE wooded yard. Three bedrooms and two bathrooms with bonus bedroom/den/office or nursery. Stainless steel appliances, recessed lighting, 2X6 walls, York high efficiency heat pump system. Extra storage in eves. Nice deck overlooking stream and environmentally protected area. Mature trees, creates privacy from the road. 2 miles from Chestertown and close to Rt 213 for easy commuting. Owner/Agent. Immediate occupancy!

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,036
Status:
Active
MLS#:
MDKE116542
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.26 Acres
Year built:
2010
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Very well maintained home with an open floor plan that is perfect for entertaining. Sun room off the kitchen and rear deck overlook woods and nicely landscaped yard. Wood floors, fireplace in the living room, master bedroom on the main level and huge partially finished basement are just a few of the amenities. Located in Coventry Farm you are just minutes from Chestertown's historic district, shopping, restaurants and Washington College.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,028
Status:
Active
MLS#:
MDKE116526
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.06 Acres
Year built:
1880
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Impeccably maintained charming home with a water view of the Chester River. First floor open floor plan is perfect for entertaining. Living room with fireplace flows into a gourmet kitchen and right into the dinning area. Beautifully restored staircase takes you to a landing with bookcases and three bedrooms with two baths. The full basement with interior and exterior access is dry and great for storage. Property is nicely landscaped with a brick patio in back and fencing. Most furniture and the contents are negotiable so this can be a turnkey property. Want to escape the city and enjoy small town living? Come visit this lovely home and all it has to offer. If you can't visit, a virtual tour will be coming soon.

Beds:
4
Baths:
2 Full
Sq.Ft.:
2,530
Status:
Active
MLS#:
MDKE116518
Type:
Single Family, Single Family-Detached
Subdivision:
Historic Chestertown
Lot size:
0.1 Acres
Year built:
1900
Courtesy: Doug Ashley Realtors, LLC
View additional info

Location, Location, Location! Historic downtown home situated literally in the heart of everything Chestertown has to offer....one block from the Chester River and newly renovated Chestertown Marina, one block from all the shops and restaurants, and one block from Wilmer Park! Property is well appointed for an older home with potential first floor master, 3 further bedrooms and full bath on 2nd floor and 2 further potential bedrooms on 3rd floor. Recently painted inside and out with newer roof and updated gourmet kitchen including stainless appliances, induction cook top and wall oven. The perfect low maintenance garden with raised planting beds, fire pit and entertaining area. Fenced in back yard with shed and much sought after off street parking. What more could you ask for!

Beds:
3
Baths:
2 Full
Sq.Ft.:
2,000
Status:
Active
MLS#:
MDKE116496
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester
Lot size:
1.37 Acres
Courtesy: Cross Street Realtors LLC
View additional info

TO BE BUILT - List price reflects the lot & lot development with the Haydn model. There are many other floor plans and upgrades available with Caruso Homes, however there is no builder tie-in. All on two parcels totaling approximately 1.81 Acres on a quiet street among well-kept homes and manicured lawns. The second parcel is located on Elm St which allows access from the front or back of the property. This property also includes a paid sewer allocation! Just steps from the Tolchester Marina & The Shanty and only a quick drive to Rock Hall or Chestertown.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,232
Status:
Active
MLS#:
MDKE116480
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.5 Acres
Year built:
2020
Courtesy: Rosendale Realty
View additional info

THIS 3 BEDROOM 2 FULL BATHROOM RANCHER PACKS A TON OF PUNCH FOR THE BUCK AND IS ONE OF THE LAST FEW NEW HOMES TO BE BUILT IN THIS COMMUNITY. OPEN FLOOR PLAN AND SPLIT BEDROOM DESIGN WITH VINYL PLANK FLOORING IN KITCHEN, LIVING, BATHROOMS AND LAUNDRY, STAINLESS STEEL APPLIANCES. ARCHITECTURAL SHINGLES, PUBLIC SEWER AND PRIVATE WELL. CLOSE TO TOWN AND ALL LOCAL AMENITIES. HOME IS JUST ABOUT COMPLETE. BUYER TO PAY ALL RECORDATION AND TRANSFER CHARGES. ANY BUYER CLOSING COSTS TO BE PAID BY SELLER WILL BE ADDED TO THE PURCHASE PRICE MHBR#3717 GREAT OPPORTUNITY TO OWN YOUR NEW HOME AND BE IN TO ENJOY SUMMER ON THE SHORE!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
3,429
Status:
Active
MLS#:
MDKE116500
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
0.1 Acres
Year built:
1768
Courtesy: Benson & Mangold, LLC
View additional info

New Listing ~ The Cuff House ~ an impeccably restored historic home with modern amenities and substantial upgrades located on Cannon Street in Chestertown with water views from the front porch and a short distance to downtown. This period home dates to the mid 1700~s and has seen a remarkable transformation over two renovations preserving its architectural significance while providing the comforts and convenience of modern living. Turnkey in every aspect and finished to the highest standard, this property is sure to please the discerning buyer. Two bedrooms and two- and one-half baths are in the main residence along with a two-car garage and loft apartment found across a beautifully appointed brick courtyard. Off-street access and parking, irrigation, radiant patio heat for snow and ice control, Lutron lighting system and many more innovative features set this home apart from the crowd. Contiguous unimproved parcels available separately. Call for more information and to schedule a tour by appointment only.Historic Reference from Maryland Historic Trust Document K-545 dated 5.14.02 ~ The Thomas Cuff House~The Cuff House was probably built by the mid-eighteenth century, a dating supported by Kent County Wills and Land Records for that site, remaining interior woodwork, and an archeological survey. The house was restored in 1987. On the exterior deteriorated circular-sawn siding was replaced by new beaded siding corresponding to old siding fragments found under the eaves. The deteriorated tin roof was replaced with a wood shingle roof similar to several shingles found under old flashing around the chimney. The house as restored is a simple frame, two-story structure, with a central doorway, flanked on each side by 6/6 windows. Two similar windows are on the second story front and three on each gable, one on each floor. The door and window frames have a simple ovolo backhand molding. The rear of the house, invisible from the street, is a modern frame wing with similar windows and siding. The original interior plan of the front four rooms, up and down, remains. There are two rooms on each floor, each with a fireplace built into the large central chimney. The partitions between the rooms are vertical beaded board paneling, probably original to the house. The upstairs room on the right retained all the original woodwork, window and door frames with simple molding, simple mantel with shelf, and exposed beaded corner posts. The room below also retained an early mantel - a shelf supported on a simple molding and flat pilasters between the opening surround and the bottom of the shelf. The original stairway had been built around the corner of this room but had been removed. A fragment of the railing - simple with a beaded edge along the bottom - was found during the archeological exploration. The left-hand rooms had lost in a fire all original wood trim except the paneling. Locally found K-545 replacement mantels from the late 18th or early 19th century have been installed, as well as corresponding period corner cupboards in each of the first-floor rooms. One original door remained, with four raised panels, cross-pieces mortised together and fastened with wooden pegs and the shadow of HL hinges. Other doors were reproduced to match it. In the course of re-building the unstable rear wing, the remains of a brick pavement were found back of the first-floor room on the right side. This was left exposed, with shattered bricks replaced. The new rear wing has a three-story hall with staircase rising against four walls from first floor to third, where the attic is lighted by a 616 window at each end. A large new room was built across the back, trimmed with an early Federal style fireplace (from a demolished late 18th century house near Kenton, Delaware), flanking bookcases with keystone arches, and jib doors leading to a screened/glassed-in porch.~

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,857
Status:
Active
MLS#:
MDKE116452
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.72 Acres
Year built:
1990
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Sprawling brick rancher in a lovely, peaceful setting. Over 2800 sq ft. Large rooms with lots of natural light. Huge family room with cathedral ceilings and fireplace overlooking the ample rear yard. Formal living and dining rooms with hardwood floors and crown molding. HVAC is only one year old. New well pump and WIFI controlled garage door. Water heater new in 2017. Home has a grand, palatial feel with relaxing views from all the windows. Close to Chestertown and a golf cart ride to the Chester River Yacht and Country Club. High speed internet available on site.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
4,138
Status:
Active
MLS#:
MDKE116446
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
0.46 Acres
Year built:
1994
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Beautiful home placed along the 13th fairway of the Chester River Yacht & Country Club. Sit in the pool, porch, hot tub, enjoy the manicured golf course with views of the Chester River in the distance.1st & 2nd floor masters sitting room, washer/dryer on each floor. 9' ceilings, oak floors, den & withdrawing room, good flow for entertaining. Just relax and enjoy; right here! Past garage turned into first floor master. High speed internet available on site.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,456
Status:
Active
MLS#:
MDKE116438
Type:
Single Family, Single Family-Detached
Subdivision:
Foxley Manor
Lot size:
0.44 Acres
Year built:
1962
Courtesy: Gunther-McClary Real Estate
View additional info

Renovated by a professional builder 10 years ago, this brick rancher will continue to stand the test of time. Updates include nicely finished wood floors, HVAC, newer Thermopane windows, roof, new kitchen with waterproof vinyl flooring, new bathrooms, new carpeting in bedrooms, and a new electrical sub panel in basement. The full basement gives tons of storage and even more options for finishing. There is a garage that could be a fabulous workshop. The circular drive runs around the back of the house, provides ample parking and plenty of room to store a boat on a trailer. Great location - so close to shopping, Washing College, Historic District. Within 20 minutes to a dozen marinas and public boat ramps. Just an hour and a half from Philadelphia. Easy living, all on one floor.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
3,935
Status:
Active
MLS#:
MDKE116428
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.64 Acres
Year built:
2003
Courtesy: Rock Hall Properties Real Estate
View additional info

This Beautiful Brick home is located in Coventry Farms. Its backs up to woods, partially cleared, where you will enjoy lots of wildlife, including wild turkeys feeding. Very private setting with a patio that has a walk-out entrance from the awesome basement. The rear also bodes a balcony from the kitchen. This house is only 17 years old, but recently had all new windows installed plus $10,000.00 of interior upgrades. The home has a generator and solar panels for energy efficiency. Main floor has a formal dining room and formal living room, as well as a very workable kitchen. The Master bedroom is on one side of the house, while the other 2 bedrooms are on the opposite side. The basement has a game room with a propane fireplace, wet bar, 1/2 bath, bonus room, living room, and workshop. There is a chair lift from the main floor to the basement if needed, or it can be removed. Mature landscaping with a circular asphalt driveway that connects to the 2 car garage with an entrance to the main floor.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,296
Status:
Active
MLS#:
MDKE116420
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.09 Acres
Year built:
1900
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Offered AS-IS and is eligible under the Freddie Mac First initiative through 4/24/2020- owner-occupant buyers and qualified non-profits. Investor offers are eligible for review after 20 days of the listing date New carpet~large kitchen~ walking distance to downtown

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,005
Status:
Active
MLS#:
MDKE116374
Type:
Single Family
Subdivision:
Downtown Chestertown
Lot size:
0.06 Acres
Year built:
1920
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Completely renovated with central air/heat, original wood floors, 2 full baths & tile backsplash in the kitchen! The 3rd room upstairs could be used for an office, nursery or make it into a large closet for that extra storage! Large living and dining rooms are great for entertaining with a bonus storage area. The curb appeal was enhanced with a new Mahogany front porch and all vinyl windows! Staging and professional pics to come...depending on the uplifting of the lockdown.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,064
Status:
Active
MLS#:
MDKE116414
Type:
Townhouse
Subdivision:
None Available
Lot size:
0.06 Acres
Year built:
1920
Courtesy: Benson & Mangold, LLC
View additional info

Moderate priced townhome in which mortgage payments would be less than area rentals. All the windows have been replaced and the exterior is vinyl. Fenced in backyard for your pets and includes large shed. Washer and dryer are included with purchase. Wooden floors throughout the house. Large kitchen dining room area. Makes a good rental unit with positive cash flow. Home is currently occupied with tenants with one year lease.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
1,928
Status:
Active
MLS#:
MDKE116400
Type:
Single Family, Single Family-Detached
Subdivision:
Mile Tree Village
Lot size:
0.53 Acres
Year built:
1978
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Nestled in the charming tree lined neighborhood of Mile Tree Village, this brick colonial has so much to offer. Kitchen and baths have all been updated. Open family room to kitchen. Enjoy the fireplace while you're cooking. Custom rear patio is perfect for entertaining, overlooking ample rear yard. Mature landscaping bursting with spring color. HVAC aprox 2 years old. Nice master suite with 2 closets. Just slightly removed from the center of town but still in walking distance to river, college, restaurants and shop. High speed internet available on site. Check out the virtual tour!

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,204
Status:
Active
MLS#:
MDKE116352
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
6.29 Acres
Year built:
1970
Courtesy: Cross Street Realtors LLC
View additional info

Over 6 acres of land to explore. And the home has numerous upgrades... a gorgeous master bath with huge tiled shower, upgraded hall bath and kitchen, new roof, 5 years young HVAC, FAST Fios internet connection... plus more! Large unfinished basement has interior access and tons of potential.

Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
11,840
Status:
Active
MLS#:
MDKE116276
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
306.12 Acres
Year built:
1990
Courtesy: TTR Sotheby's International Realty
View additional info

"Walnut Point Farm" ~ Exquisite 300+ Acre Waterfront Farm with over a mile of Shoreline is the perfect Eastern Shore Retreat! The Estate offers a 7,500+/- Main House with indoor and outdoor pools, Pier with Grand Boathouse and lift with 7ft+/- MLW, Large 3 bedroom Historic Guest House, Waterfront Caretakers Home, Large Barn for all farming equipment, Covered Bridge with many other outbuildings and blinds plus a few waterfowl ponds. This Estate is perfect for those looking for and escape from the hustle and bustle of the metropolitan lifestyle that would like to take in all that nature offers with a plethora of high end amenities. Please See Truplace Interactive Tour For more Photos and Floorplan at https://mls.TruPlace.com/property/406/84311/

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
1,944
Status:
Active
MLS#:
MDKE116284
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.28 Acres
Year built:
2007
Courtesy: Clark & Co Realty, LLC
View additional info
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