Chestertown MD Real Estate & Homes for Sale

103 Properties Found

The median home value in Chestertown, MD is $221,000. This is higher than the county median home value of $192,000. The national median home value is $232,276. The average price of homes sold in Chestertown, MD is $221,000. 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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Beds:
2
Baths:
2 Full
Sq.Ft.:
1,204
Status:
NEW LISTING
MLS#:
MDKE116352
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
6.29 Acres
Year built:
1970
Contact:
Liddy Campbell, liddy@csrealtors.com, 410-708-5433
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:
2
Baths:
1 Full/1 Half
Sq.Ft.:
920
Status:
NEW LISTING
MLS#:
MDKE116372
Type:
Single Family, Single Family-Detached
Subdivision:
Downtown Chestertown
Lot size:
0.21 Acres
Year built:
1980
Contact:
Kristina Hyland, kristina@cbchesapeake.com, 410-725-9225
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Just a few blocks away from the Chester River and all that Chestertown has to offer, this cute bungalow has been well maintained and was a very successful rental for 19 years! Owner has always kept up with repairs and maintenance. With great spaces, the large kitchen allows room for a rolling island, dining large enough for a table of 10 and the front living room has an abundance of natural light. The bedrooms are large, one with a half bath attached and the laundry/mud room/summer kitchen has plenty of room for storage with a closet and cabinets. An alley runs by the back yard allowing you dual access to your property with easy accessibility to your car port & multiple storage buildings. A great investment at this price as there are a few new homes/renovations on Cannon St. currently taking place to bump up your home value.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,012
Status:
NEW LISTING
MLS#:
MDKE116382
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Year built:
1988
Contact:
Nora Turner, nora.turner@longandfoster.com, 410-463-0011
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Beautifully renovated home, move-in ready, perfect for a first time homebuyer! Close your eyes and allow me to virtually guide you through your soon to be home: Enter the home to an open concept living room, kitchen and dining room that welcomes you with the ideal lighting-perfect for entertaining. New, eye-catching laminate flooring and carpet, new appliances, fresh coat of paint, updates throughout the home, a master bedroom with a moderately sized walk-in closet and a stunning bathroom that will impress you! The outside is just as amazing as the inside- there is a charming wraparound porch, a storage shed and the landscaping on this home is fascinating! Come take a look, pictures do not do this home justice! This home comes with the WOW factor in addition to affordability! Yes, you CAN own for less than you rent! Home is located within a short distance of downtown, shopping and Washington College. Tax record shows address as 126 Prospect.

Beds:
4
Baths:
3 Full
Sq.Ft.:
2,068
Status:
NEW LISTING
MLS#:
MDKE116336
Type:
Single Family, Single Family-Detached
Subdivision:
Crestview
Lot size:
0.69 Acres
Year built:
2005
Contact:
Liddy Campbell, liddy@csrealtors.com, 410-708-5433
Courtesy: Cross Street Realtors LLC
View additional info

Coming Soon! This immaculately maintained home offers main level living... gleaming hardwood floors, a generous master suite, a screened in porch and huge fenced backyard overlooking the community open space, and a bonus bedroom or rec room and full bath upstairs. More pictures will be available soon!

Beds:
5
Baths:
5 Full/1 Half
Sq.Ft.:
11,840
Status:
NEW LISTING
MLS#:
MDKE116276
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
306.12 Acres
Year built:
1990
Contact:
Trey Rider, treyrider@gmail.com, 443-786-0235
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
Contact:
Kaitlyn Collins, kaitlyn.clarkrealty@gmail.com, 410-490-9157
Courtesy: Clark & Co Realty, LLC
View additional info
Beds:
4
Baths:
3 Full
Sq.Ft.:
2,942
Status:
Active
MLS#:
MDKE116378
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
1 Acres
Year built:
1900
Contact:
Miles Norris, mnorrisselect@gmail.com, 410-708-5423
Courtesy: Select Land & Homes, LLC
View additional info

One of the few properties in Chestertown on a full acre of land! The solid brick home has undergone an extensive renovation to include a gourmet kitchen, new HVAC and windows, and hardwood floors. This home is a perfect fit for a family with 4 bedrooms (first floor master), 3 full bathrooms, and a newly fenced backyard. French doors lead to the screened porch and a waterproofed basement makes for great storage. Only a short walk to bike trails, downtown restaurants, marina and Washington College.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
3,144
Status:
Active
MLS#:
MDKE116368
Type:
Single Family, Single Family-Detached
Subdivision:
Coventry Farms
Lot size:
0.23 Acres
Year built:
2007
Contact:
Retha Arrabal, rarrabal@hotmail.com, 410-810-0010
Courtesy: Doug Ashley Realtors, LLC
View additional info

Coventry charmer with a fenced back yard, deck with new awning makes this an "outdoor room". Family room is open to the kitchen/breakfast area. Partially finished basement for playroom, office/den, you choose. Three nice bedrooms with great light, well landscaped lot. Move in ready, nicely painted.

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
1,936
Status:
Active
MLS#:
MDKE116230
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.38 Acres
Year built:
2006
Contact:
Jeff Guthrie, jeffismyrealtor@gmail.com, 410-708-9593
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

Hot New Listing in Tolchester!!! Check out this 4 Bedroom 2.5 bath home with approx 1936 sq ft in Tolchester Estates. Recently Updated . This is a quality stick built home with an attached 1 car garage and tons of driveway parking for cars or boat. Sliding glass doors lead to the deck and private back yard. Home backs to wooded area for privacy. Relax on the deck and enjoy peaceful Tolchester Estates. Also offers a lovely front porch to sit and listen to the wildlife. Home is on public sewer line. Has a water softener.Tolchester Marina and the Shanty Tiki Bar are within walking distance making this move in condition property the perfect full time residence or weekend getaway. Schedule your SHOWING TODAY !!!

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,108
Status:
Active
MLS#:
MDKE116362
Type:
Single Family, Single Family-Detached
Subdivision:
Fairlee
Lot size:
2.5 Acres
Year built:
1955
Contact:
Tracy Stone, tstone@cbchesapeake.com, 443-480-0610
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

The house needs work, but it sits on over 2 acres just outside of Fairlee. Classic knotty pine paneling, hardwood floors, two bedrooms and a bathroom with a walk in tub. Large detached garage has an addition with a kitchenette. An FHA 203K loan may be a perfect fit. Bring your ideas!

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,485
Status:
Active
MLS#:
MDKE116358
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
0.69 Acres
Year built:
1962
Contact:
Cindy Genther, cindy@rockhallproperties.com, 443-480-1953
Courtesy: Rock Hall Properties Real Estate
View additional info

A peaceful setting for this classic brick cape cod just outside of Chestertown. Enjoy a picnic on the porch or a dip in the pool - there's plenty of room to play on this more than 1/2 acre lot. The 2012 restoration included a new kitchen with stainless steel appliances, and new fixtures in the floor bathroom. Lots of space and flexibility with 4 bedrooms - 2 on the 1st floor and 2 on the second! Original wood floors on the 1st floor living area plus a fireplace in the living room give the home a warm and cozy feel. Just minutes from Chestertown and affordably priced in today's improving market.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,600
Status:
Active
MLS#:
MDKE116302
Type:
Condo
Subdivision:
Chester River Landing
Year built:
2009
Contact:
Richard Keaveney, rdkeaveney@gmail.com, 410-708-6470
Courtesy: Cross Street Realtors LLC
View additional info

This 1,600 sf ritzy waterfront suite simply exudes class. The unobstructed panoramic views of the Chester to the Bridge serve as living art bringing the River into the home. Well-appointed architectural detail accents an original open floor plan further illuminated by the abundance of natural light that fills the space. The custom storage capacity is unprecedented! If you are looking for an energy efficient turnkey waterfront that offers maintenance free living, This Is It! Oh, bring your boat too. It will fit nicely in the slip that offers 4' MLW that happens to be next to the floating dock for ease of access.

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,008
Status:
Active
MLS#:
MDQA143260
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.64 Acres
Year built:
1969
Contact:
Laura Anthony, lanthony.chesapeakerealestate@gmail.com, 410-739-5306
Courtesy: Chesapeake Real Estate Associates, LLC
View additional info

*INVESTOR ALERT!* Opportunity awaits in Chester Harbor - This is a cute 2 bedroom, 1 bath rancher with a full basement and is priced to sell. This could be turned into a 3 bedroom rancher. Home has a full unfinished basement as well as a shed with a great yard. Quick and easy access to Chester River. Convenient to Rt 213, Washington College and the Chestertown area. This property is As-Is.

Open House:

Saturday, 4/18 2:00-4:00PM

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
3,440
Status:
Active
MLS#:
MDKE116330
Type:
Single Family, Single Family-Detached
Subdivision:
Langford Farm
Lot size:
4.39 Acres
Year built:
2001
Contact:
Tracy Stone, tstone@cbchesapeake.com, 443-480-0610
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

This is a "must see" to appreciate all this waterfront property has to offer. Located on the East Fork of Langford the setting is beautiful with grounds designed by a landscape architect. The home is impeccably maintained with a bright open floor plan. New gourmet kitchen with granite counter tops and cork floor. The systems are new, wood floors throughout and a master bedroom on the first floor. There is a full dry basement and a detached two car garage with plenty of storage space. Wildlife abounds and can be enjoyed from the bank of windows overlooking the water, front porch or one of two patios. Just minutes from Chestertown, the historic district, restaurants, shopping and Washington College.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,500
Status:
Active
MLS#:
MDKE116294
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.35 Acres
Year built:
2020
Contact:
Dilip Kinra, dnk@dnkrealestate.com, 301-706-1090
Courtesy: D N K Real Estate, LLC
View additional info

BRAND NEW CONSTRUCTION 3 BR Cape Cod in quiet, waterfront community of Chesapeake Landing located just off Worton Creek in beautiful, historic Chestertown. A short drive to the restaurants and shops of Rock Hall on the Chesapeake Bay. Excellent area schools, parks and community center. 1st level Master BR with full bath. Upstairs, 2 BR and full bath. Large, eat in kitchen. Living Room. Separate front room for dining, office or family room needs. Back patio is perfect for entertaining. Community is water access with 2 marinas, boat slips and docks. A perfect location to keep your boat for a weekend away on the beautiful Eastern Shore or to make this your permanent home.

Beds:
5
Baths:
2 Full
Sq.Ft.:
3,000
Status:
Active
MLS#:
MDQA143204
Type:
Single Family, Single Family-Detached
Subdivision:
Kings Court
Lot size:
1 Acres
Year built:
1994
Contact:
Dan Foster, danbfoster@gmail.com, 410-310-3393
Courtesy: Long & Foster Real Estate, Inc.
View additional info

This property is nestled on over an acre at the end of a private cul-de-sac. The exterior feature a well-groomed yard, asphalt driveway with lots of space for cook-outs and outdoor entertaining. The interior features 5 bedrooms 2 full baths large kitchen and separate dining room. There is a spacious living room with an additional family and a oversized two car garage. Call today for a private showing before it is gone.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,280
Status:
Active
MLS#:
MDQA143194
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Harbor
Lot size:
0.52 Acres
Year built:
2020
Contact:
Karen Clark, karen@clarkrealty.homes, 410-490-2183
Courtesy: Clark & Co Realty, LLC
View additional info

Under construction, June Delivery....Looking for a Brand New Home?? Look No Further!! Relaxed, Easy One Level Living.....Beautiful & Affordable....Open Floor Plan Rancher on over 1/2 acre, 3 bedrooms, 2 baths, gorgeous white kitchen with granite counter tops, spacious living room with lots of natural light, high ceilings, hardwood floors, upgraded lighting, SS appliances, front porch, large back deck for entertaining.......HOA is optional (provides access to ramp and playground).......Quality Built, MHBR#3423. Not actual house - pictures are similar to home being built

Beds:
3
Baths:
4 Full/1 Half
Sq.Ft.:
4,446
Status:
Active
MLS#:
MDKE116268
Type:
Single Family, Single Family-Detached
Subdivision:
Kent County
Year built:
1990
Contact:
Ashton Kelley, akelleyre@gmail.com, 410-708-8144
Courtesy: Gunther-McClary Real Estate
View additional info

Looking for a family compound? This wonderful setting captures the beauty and tranquility of the East fork of Langford Creek/Bay with the house nicely tucked away in a cove. The subject property is one of 5 waterfront properties that belong in the Cacaway Farm Cooperative Housing Corporation, an exclusive farm housing community. Experience the same benefits of a fee simple ownership but share the cost of expenses. Enjoy privacy and the use of your own waterfront with sandy beach by way of a gentle slope to the water, launching kayaks or canoes while a slip at the community dock gives sail boaters the water depth needed. A hard to find combination. The original house built in 1990 was added on to provide 2 separate quarters, now it is one house with duplicate areas. It has been well cared for and offers a very unique floor plan which brings the two living areas together. Enjoy these very scenic views of a southern exposure and 2 separate decks. The later built one bedroom garage apartment is situated to take advantage of the West Fork view. It is improved by 2 heated garage spaces plus a smaller area for storage. Come see for yourselves what this property has to offer.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,591
Status:
Active
MLS#:
MDKE116288
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.34 Acres
Year built:
1982
Contact:
John Carroll, john@villageagents.com, 410-648-6844
Courtesy: Village Real Estate Company LLC
View additional info

Spacious rancher on quiet street in Byford development. Home features wood and ceramic flooring, wood burning fireplace and exposed beams. Split floor plan with master suite tucked away from the rest of the house, with tons of closet space! Seller just installed an all brand new central heating and cooling heat pump system. Large garage accessible by rear mudroom and laundry area. Cozy rear sunroom opens onto peaceful deck, backyard shed for storage and charming mature landscaping! With an open mind and some vision, this house could very well become your new HOME! Call today!

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,176
Status:
Active
MLS#:
MDKE116202
Type:
Single Family, Single Family-Detached
Subdivision:
Washington Park
Lot size:
0.47 Acres
Year built:
1998
Contact:
Kristina Hyland, kristina@cbchesapeake.com, 410-725-9225
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

*CORONA VIRUS UPDATE* WE ARE STILL HOLDING SHOWINGS AT THIS TIME UNTIL FURTHER NOTICE AND TAKING EVERY PRECAUTION TO KEEP YOU AND THE SELLER SAFE. This 1200sq ft., 3 BR, 1 Bath home was built in the 90~s and though it has always had ~strong bones~, many improvements have been made since the current owner purchased it in 2008. In September 2017 the asphalt roof was replaced. New kitchen cabinets, countertops & sink were installed in the summer of 2018. Laminate wood flooring was originally in the kitchen and has been added to the living room, hallway and left front bedroom since 2016. The other 2 bedrooms have ww carpeting & 6 of the original windows have been replaced since purchase. Electric has been kept updated with newer GFI and some USB outlets being added within the past 2 years. The property is pie shaped and approximately .41 acres with lovely, mature shade trees lining one entire side of the yard and the back. There is a 10x12 wooden deck on the back and a covered front porch with a built in bench. Washington Park has a neighborhood park that has recently been updated with playground equipment, benches, picnic tables and a brand new pavilion and basketball court. Fun for all!

Beds:
2
Baths:
1 Full/1 Half
Sq.Ft.:
936
Status:
Active
MLS#:
MDKE116246
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown Historic District
Lot size:
0.04 Acres
Year built:
1900
Contact:
Richard Budden, rbudden@easternshoremdre.com, 443-480-1181
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Great downtown Chestertown location! Recently updated home is set in the Historic District and is just a walk away from Washington College, the University of Maryland Medical Center, the Chester River, restaurants, shops and walking trails. The delightful home evokes cottage charm with wood floors and bead board detail, while outside, the fenced backyard with plantings offers an inviting seating area. Founded in 1706, Chestertown is a charming riverfront town. Residents and visitors alike can enjoy the Chester River Walk, strolling downtown, embarking on a river cruise and having fun at annual events. Located about 90 minutes from Washington, D.C. and Philadelphia.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
2,596
Status:
Active
MLS#:
MDKE116228
Type:
Single Family, Single Family-Detached
Subdivision:
Langford Bay Estates
Lot size:
0.53 Acres
Year built:
1948
Contact:
Richard Budden, rbudden@easternshoremdre.com, 443-480-1181
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Eastern Shore Waterfront Home with commanding views of Langford Bay and the Chester River is set in a quiet, rural community just 15 minutes from historic Chestertown. Enjoy boating and water activities with the 4-ft MLW deep water dock. Designed to maximize the spectacular water views, the 3 bedroom brick home features an open design, a first floor master suite, office, flex room and garage. Founded in 1706, Chestertown is a lovely walking town with shops, theater, waterfront dining, cafes and oyster bar. Residents and visitors alike participate in annual events and enjoy the Chester River Walk and river cruises. Located about 90 minutes from Washington, D.C. and Philadelphia.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,310
Status:
Active
MLS#:
MDQA143120
Type:
Single Family, Single Family-Detached
Subdivision:
Pearl Creek Estates
Lot size:
1.58 Acres
Year built:
2020
Contact:
David Dauses, dj@watermanrealty.com, 443-994-4180
Courtesy: Coldwell Banker Waterman Realty
View additional info

New construction to be built. 3 Bedrooms, 2 Full Baths. Modern open floor plan. Master suite with separate shower and jetted soaking tub. Hardwood floors. Cathedral ceilings. Granite counter tops. Walk in closets. Two car garage. Beautiful peaceful setting. Large 1.58 acre lot. Quality stick built construction.

Beds:
3
Baths:
2 Full/1 Half
Sq.Ft.:
1,756
Status:
Active
MLS#:
MDKE116250
Type:
Single Family, Single Family-Detached
Subdivision:
Crestview
Lot size:
0.5 Acres
Year built:
1989
Contact:
Lee Davis, leedavisrealestate@verizon.net, 410-778-0015
Courtesy: Davis Real Estate, Inc.
View additional info

Move in condition Cape Cod Home in Crestview. Near Washington Square Shopping Center, Churches, Washington College and a mile from downtown Historic Chestertown. Master bedroom on the first floor, large rear deck, attached garage and fenced rear yard.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,950
Status:
Active
MLS#:
MDKE116218
Type:
Single Family, Single Family-Detached
Subdivision:
Country Club Estates
Lot size:
1.01 Acres
Year built:
1958
Contact:
Doug Ashley, doug@dougashleyrealtors.com, 410-708-0480
Courtesy: Doug Ashley Realtors, LLC
View additional info

Location, Location, Location! Rare opportunity to own a home adjoining Chester River Yacht and Country Clubs 18 hole championship club course! Located on the dogleg of the 15th hole, you are just a short distance to club house. This home has large rooms with wood flooring throughout most of this home. The family/dining area combine with a wood burning fireplace a central focal point for family gatherings or for the occasional party with neighbors and friends. There is a Florida/sun room that has views of golf course and exits to the rear brick patio, perfect for weekend barbecues. There are 4 bedrooms, all with built ins. The kitchen opens to the family/dining areas. There is a partial basement where you will find the mechanical s and there is a 2nd with unfinished pine wood floors that could easily be renovated to be a large owners suite, additional family area or just leave it the way it is so that you have plenty of storage. Finally there is a detached 2 car garage that actually has 3 garage doors, 2 for your cars and one for your lawn toys. Close to Historic Downtown Chestertown and the Marina!

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