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Chestertown MD Real Estate & Homes for Sale

41 Properties Found

The median home value in Chestertown, MD is $271,000. This is higher than the county median home value of $207,500. The national median home value is $266,648. The average price of homes sold in Chestertown, MD is $271,000. 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.


1–25 of 41 properties displayed
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Open House:

Saturday, 5/22 11:00-1:00PM

Beds:
2
Baths:
2 Full
Sq.Ft.:
840
Status:
NEW LISTING
MLS#:
MDKE118002
Type:
Single Family, Single Family-Detached
Subdivision:
Tolchester Estates
Lot size:
0.18 Acres
Year built:
1945
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Recently upgraded cottage in Tolchester Estates private beach community! Enjoy the beach /water access and take a quick ride to Tolchester Marina for food, drinks and entertainment along the huge sandy beach. This adorable little getaway features newer heating/cooling systems, brand new well & the roof is only 3 years old! Want more.....brand new tiled baths, high ceilings, concrete countertops, tile backsplash, brand new appliances, sliding barn door and a huge deck!

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,152
Status:
NEW LISTING
MLS#:
MDKE118074
Type:
Single Family, Single Family-Detached
Subdivision:
Washington Park
Lot size:
0.48 Acres
Year built:
1966
Courtesy: EXIT Preferred Realty
View additional info

Newly remodeled ranch home right outside of Chestertown! This 3 or 4 bedroom home has 1.5 baths and a large living area. Some of the improvements include new floors throughout, new doors, new kitchen which includes new stainless steel appliances. New roof, some new windows where needed. New paint throughout. Home also has central AC propane heat, 2 car detached garage, a great back yard and back patio. Great ranch home with a lot to offer! Showings start Saturday May 8th. Call me today for a personal tour!

Beds:
3
Baths:
3 Full/1 Half
Sq.Ft.:
3,300
Status:
NEW LISTING
MLS#:
MDKE118082
Type:
Condo
Subdivision:
Chester River Landing
Year built:
2013
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Live beautifully and comfortably in this waterfront community on the Chester River, just minutes from historic Chestertown. The elegant amenities of the home are complemented by the amenities of the community. View the abundant wildlife on the fresh-water pond from your deck or take a few steps to stand at the edge and watch up close. A pier on the Chester is great for crabbing, fishing, or launching your kayak for a cruise. Boat slips are available. Spend a warm afternoon sunbathing or cooling off in the community pool. 2nd story main living, with guest quarters on entry level. Third bedroom is being used as a family room. Delightfully different, unquestionably unique, and ready for you to move in.

Beds:
3
Baths:
2 Full
Sq.Ft.:
3,637
Status:
NEW LISTING
MLS#:
MDKE117978
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
2.01 Acres
Year built:
1964
Courtesy: RE/MAX Executive
View additional info

Gorgeous 2 acres in Chestertown. This rancher is boasting over 2400 sq ft with an unfinished basement. As you walk into this home you walk into the large living room with gorgeous hardwood floors and a wood burning stove. Off of one end of the living room is a relaxing screened in porch and off the other end is a gorgeous deck with bench seating all over looking the 2 acres of privacy. As you walk into the living room, to the left is the kitchen and 3 Large bedrooms, and 2 full bathrooms. Downstairs you have a full unfinished basement ready for your finishing touches or perfect for storage. Back upstairs you have a separate laundry and mud room. There is a detached garage with full apartment and enclosed porch. Great for an in -law suite, office or rental opportunity. Convenient location. All the privacy but still close to all town amenities. Do NOT hesitate on this one!

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,136
Status:
NEW LISTING
MLS#:
MDKE118084
Type:
Townhouse
Subdivision:
Calvert Heights
Lot size:
0.05 Acres
Year built:
1992
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Freshly painted and updated with new flooring, bathroom vanity and new roof! Steps away from Downtown Chestertown and one block from Washington College, this home is move in ready! A new French Door leads to the quaint back yard with a shed for storage and access to the alley for private parking. Walkable to all that Chestertown has to offer and cheaper then renting!

Beds:
2
Baths:
2 Full
Sq.Ft.:
1,098
Status:
NEW LISTING
MLS#:
MDKE118076
Type:
Condo
Subdivision:
Historic District Chestertown
Year built:
1900
Courtesy: Cross Street Realtors LLC
View additional info

Easy waterfront living on prestigious North Water Street in Historic Downtown Chestertown ... this cottage-like condominium is on the first floor of a beautiful federal-styled brick manse on the Chester River. Only six units, two per floor grace the building. A recently refurbished lawn and garden separate the picture-perfect private porch from your own boat slip. A generously sized living room with 9 foot ceilings, a gas fireplace, three large paned windows and built-in bookshelves greets everyone who enters. A long hallway, that can serve as an inspiring art gallery, features two bathrooms to the left and two bedrooms to the right. Straight ahead is where life continues to be enjoyed. An exceptionally designed kitchen includes a discreetly hidden full-size washer and dryer along with quality appliances, granite topped island, and of course a generous window view of the river. Open to the kitchen is a living/den area with French doors leading to the porch. A sofa bed would be perfect in this den IF your guests are willing to brew the early morning coffee. The porch can accommodate a large dining table as well as a comfortable seating area. Your kayaks and other water toys can be stored porch side.

Beds:
3
Baths:
2 Full
Sq.Ft.:
n/a
Status:
NEW LISTING
MLS#:
MDQA147616
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.38 Acres
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Welcome Home. Come see this beautiful 4 bedroom 2 bathroom rancher. You could easily turn one of the spare bedrooms into an office. New construction means new memories to be made. 45 miles from Bay Bridge, in a rural setting. Just down the road from Duck Neck campgrounds, and just a few miles from Downtown Chestertown. Enjoy the peace and serenity the location provides.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,260
Status:
NEW LISTING
MLS#:
MDKE118072
Type:
Townhouse
Subdivision:
Chester Arms
Lot size:
0.05 Acres
Year built:
2021
Courtesy: D N K Real Estate, LLC
View additional info

New Construction 1 & 2 story 3 BR townhomes available in historic Chestertown (currently 103 Conley Drive is on sale). Modern open concept floor plans with ample living and kitchen areas. Kitchen boasts upgraded stainless steel appliances, granite countertops and bright white cabinetry. Durable vinyl plank flooring throughout home with plush carpets in bedrooms. All bathrooms have granite topped vanities and include upgraded bronzed fixtures. Plenty of closet storage including private storage unit on covered back porch. Construction is near completion; some units will be ready for move-in May 2021. Interior and Exterior units available. One story units have 2 full bathrooms (the one listed has 1.5 bathrooms). This is a unique opportunity of owning a brand new home on Maryland's Eastern Shore. The property is conveniently located a short walking distance to local stores, restaurants and Kent County's brand new YMCA; a short drive from Washington College and Chestertown's historic waterfront district. Floorplans available upon request. Property can be shown anytime.

Beds:
4
Baths:
3 Full/1 Half
Sq.Ft.:
2,465
Status:
NEW LISTING
MLS#:
MDQA147570
Type:
Single Family, Single Family-Detached
Subdivision:
The Grove
Lot size:
1.03 Acres
Year built:
2021
Courtesy: Clark & Co Realty, LLC
View additional info

Under Construction, end of May completion...Stunning Custom Built Farmhouse with all the bells and whistles perfectly sited on over 1 acre features 4 bedrooms, 3.5 baths, 1st floor primary bedroom with trayed ceiling, walk-in closet, lavish bath with tiled shower and double vanity, gorgeous designer kitchen with island, SS appliances, quartz countertops, farm sink and a custom pantry by California Closets, open dining area and living room with cathedral ceiling. Other highlights of the home include extra wide foyer, custom bench/locker area, Jack & Jill bath, separate laundry room, powder room, wrap around porch, LED designer lighting throughout, paddle fans, recessed lighting, black windows, flat screen TV setup and USB outlets in living room & primary bedroom, This home will be love at first sight

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,248
Status:
NEW LISTING
MLS#:
MDKE118026
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.34 Acres
Year built:
1998
Courtesy: Keller Williams Flagship of Maryland
View additional info

Incredible opportunity to own a 4 Bedroom located in the water oriented community of Chesapeake Landing. The community offers many ammenties, however it is a Voluntary HOA with use of boat launch and picnic area. The home features a new roof (that is currently waiting for installation), large spacious yard, and owners bedroom with onsuite. Spacious parking for boat or RV or gathering of friends and family.

Beds:
4
Baths:
3 Full
Sq.Ft.:
2,200
Status:
NEW LISTING
MLS#:
MDKE118056
Type:
Single Family, Single Family-Detached
Subdivision:
Byford Heights
Lot size:
0.35 Acres
Year built:
1965
Courtesy: Benson & Mangold, LLC
View additional info

A jewel of a home is located in historic, quaint Chestertown. It features 4 bedrooms & 3 bathrooms including an amazing in-law or ownerâs suite, and an attached, climate-controlled garage, all on one level. The outside is a gardeners' dream, in-town but a private oasis, beautifully landscaped with a patio & pergola, garden shed with water & electric, and fenced rear yard. The enclosed, large sunroom has walls of windows with unobstructed views of the peaceful, natural setting and provides plenty of room for dining. The updated kitchen opens to the sunroom and has soft close cabinets, quartz countertops, new appliances and a skylight. Bathrooms have been updated as well as mechanicals. Hardwood flooring throughout with tile in kitchen, sunroom & foyer and a gas fireplace in the den. This home and property are perfect for entertaining inside and out! Close to local restaurants, coffee shops, fine dining, shopping, and community attractions and events. Just blocks from the Chester River for the water enthusiast with nearby marinas!

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
NEW LISTING
MLS#:
MDKE118052
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

There are only 6 units left... so come take a look now! Only 2 bedroom townhomes are left! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
3
Baths:
1 Full
Sq.Ft.:
888
Status:
Active
MLS#:
MDKE118018
Type:
Single Family, Single Family-Detached
Subdivision:
Quaker Estates
Lot size:
0.35 Acres
Year built:
1964
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Updated in 2021 with granite countertops, new stainless steel appliances, washer & dryer, windows, plumbing, electric, insulation, deck, central AC, LVP flooring, ceiling fans in all bedrooms and ceramic tiled bathroom. This 3 bedroom home, also has a recently finished additional room that could be used as a home office, play room, etc. to fit your needs and makes the home a total of 1,100 sq ft! It's practically a brand new home and conveniently located near Downtown Chestertown! **please note showings will not start until 5/8**

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,198
Status:
Temporarily Off Market
MLS#:
MDKE117982
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.26 Acres
Year built:
1969
Courtesy: Gunther-McClary Real Estate
View additional info

Don't miss out on this well-cared for brick rancher with tons of curb appeal in College Heights. Brand new roof with transferrable warranty. Expanded and updated kitchen with new appliances. Extra large sun room with hot tub leads you to the back yard with an in-ground pool-- just in time for Summer. An entertainer's dream! Home boasts hardwood floors. Three bedrooms and 1 1/2 baths. Unfinished basement with ample storage space. Side entry, two car garage. Ideally located near schools, shopping, and downtown Chestertown. Make this place your home!

Open House:

Saturday, 5/15 12:00-2:00PM

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE118012
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

There are only 6 units left... so come take a look now! Only 2 bedroom townhomes are left! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Open House:

Saturday, 5/15 12:00-2:00PM

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE118010
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

There are only 6 units left... so come take a look now! Only 2 bedroom townhomes are left! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,269
Status:
Active
MLS#:
MDKE117998
Type:
Townhouse
Subdivision:
Tolchester
Lot size:
0.07 Acres
Year built:
1955
Courtesy: Doug Ashley Realtors, LLC
View additional info

There are only 6 units left... so come take a look now! Only 2 bedroom townhomes are left! Features a terrific open kitchen with all major appliances, nice living room/dining room combination with a slider to the patio. Bedrooms have vaulted ceilings! Tolchester Village is a community with completely updated 3 bedroom and 2 bedroom units to choose from. Thoughtfully remodeled and they show great! Common areas include a playground!!! For qualified buyers your mortgage payment could be $900+/- per month. There is HOA fee of $40 per month, and all units are served by public water and sewer. Affordable, beautiful, and low maintenance!! What could be better?

Beds:
7
Baths:
5 Full/2 Half
Sq.Ft.:
10,328
Status:
Active
MLS#:
MDKE117878
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
21.02 Acres
Year built:
1800
Courtesy: Select Land & Homes, LLC
View additional info

This Majestic stately residence is perched at a perfect elevation with incredible views of undeveloped, preserved farmland and gently sloping lawn to the 1000' of white sandy beach on the Upper Chesapeake Bay. This awesome property offers ultimate privacy with the convenience to several urban centers within 90 minutes away. Historic Chestertown and the bayside town of Rock Hall are only moments away as well! Property features include a restored Georgian Colonial main residence in great condition with many original features and numerous recent updates, a large enclosed pool with attached recreation play house, 4 stall barn with 4 acre fenced pasture, tenant house, detached garages, extensive patios and landscape features, gorgeous private beach with bath house and much, much more! Come take a look and take advantage of all the value at a very reasonable asking price! Subject to Maryland Environmental Trust Easement, see documents.

Beds:
3
Baths:
1 Full
Sq.Ft.:
1,454
Status:
Active
MLS#:
MDKE117962
Type:
Single Family, Single Family-Detached
Subdivision:
Chester Heights-Rt 213 N
Lot size:
0.21 Acres
Year built:
1956
Courtesy: Cross Street Realtors LLC
View additional info

PRIME LOCATION!!! This adorable 3 BR, 1 BA bungalow is located on one of the main thoroughfares in Chestertown. Zoned Intense Village which allows residential and/or a broad range of commercial uses. The living space includes a large family room off the galley kitchen, new heat-pump with central air, new carpet, screened in-porch and a detached 2-car garage with ample off street parking. Close to all Chestertown offers; Washington College, restaurants, hospital, local shops, new marina and much more. Lots of possibilities here!

Beds:
4
Baths:
2 Full/1 Half
Sq.Ft.:
2,858
Status:
Active
MLS#:
MDQA147250
Type:
Single Family, Single Family-Detached
Subdivision:
Chestertown
Lot size:
2.55 Acres
Year built:
2004
Courtesy: Chaney Homes, LLC
View additional info

Beautiful Colonial on over OVER 2.5 acre's - secluded wooded lot (some cleared areas) in Queen Anne's County -Charming 4 bedroom 3 bath custom built with unique features and updates throughout - 2600+ square feet - Beautiful brick fireplace with gleaming cherry hardwood floors - New carpet just installed on second floor - open floor plan with formal dining room and large eat in country kitchen - Room for an in-home office or keep as additional recreational area - luxury master suite with loft, walk in closet and private en-suite master bath - charming claw tub and separate shower offer relaxation after a long day - Laundry on Upper floor for added convenience - Work from home in your built in Studio on the main floor and when your done....float in the pool and entertain off the large paver patio just off the back sliders - Relax on a beautiful wrap around front porch - Nature abounds - NO HOA RESTRICTIONS - Room to indulge your backyard desire - Perfect location with in minutes to 301, Downtown Chestertown, Centreville, or The Bay Bridge- Queen Anne's County High School, Suddlersville Middle, and Church Hill Elementary-ADDITIONAL NEIGHBORING LOT CAN BE PURCHASED IF INTERESTED - 2 acres and already perc approved for additional build

Beds:
2
Baths:
1 Full
Sq.Ft.:
1,064
Status:
Active
MLS#:
MDKE117958
Type:
Single Family
Subdivision:
Chestertown
Lot size:
0.06 Acres
Year built:
1920
Courtesy: CENTURY 21 New Millennium
View additional info

INVESTOR OPPORTUNITY. Great rental property in a college town. Well maintained, updated and reasonably priced home located near the heart of Chestertown. Walking distance to fine arts, restaurants and waterfront. Potential space for a half bathroom off of the dining room. Safe location, close to elementary school. Hardwood throughout, and a fenced-in backyard with a 10 x 20 storage shed. Perfect for a new family or someone looking to downsize. A rare find. Sold As-Is.

Beds:
3
Baths:
1 Full/1 Half
Sq.Ft.:
1,050
Status:
Active
MLS#:
MDKE117956
Type:
Single Family, Single Family-Detached
Subdivision:
Chesapeake Landing
Lot size:
0.37 Acres
Year built:
1969
Courtesy: The Hogans Agency Inc.
View additional info

Cozy ranch style lakefront cottage on large lot with beautiful hardwood floors - one half mile from Public Landing Marina. Scenic views and wildlife abound with outstanding fishing on the the lake. A must see - your enjoyment awaits!

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,356
Status:
Active
MLS#:
MDKE117886
Type:
Single Family, Single Family-Detached
Subdivision:
College Heights
Lot size:
0.31 Acres
Year built:
1966
Courtesy: Coldwell Banker Chesapeake Real Estate Company
View additional info

Well maintained 4 BD 2 BA ranch in College Heights. Office, wood floors throughout with an attached garage and a detached garage/shop. Nice deck out back and beautiful mature trees. Close to the Historic District, Washington College, shops and restaurants. Tenant occupied so advanced notice needed.

Beds:
3
Baths:
2 Full
Sq.Ft.:
1,152
Status:
Temporarily Off Market
MLS#:
MDKE117900
Type:
Single Family, Single Family-Detached
Subdivision:
None Available
Lot size:
3 Acres
Year built:
1978
Courtesy: Keller Williams Flagship of Maryland
View additional info

Investor, Build Dream Home or Remodel current home. -Renters are gone, but some of their items are still on the land. HOME IS AS IS....Looking to be away from it all, but close to amenities? Two buildable lots. The home sits on 3 acres and then another 1/2 acre in front of the home to the Road. Home is 1152 sq. ft. of main living Both lots are level. Main level living with large bright living room, country kitchen with dining area, and laundry closet. 3 bedrooms and 2 full baths. Front porch and back decking. Privacy and Short drive to Great Oak Landing Marina/Golf Club, Water, Speedway, and downtown Chestertown for shopping, restaurants, and pier. Stone throw to Rock Hall and Delaware. Please note -this home is not a mobile home as stated on tax records. The home is AS-IS. Due to being so close to the water, the property has a holding tank that was just pumped and inspected. No, the blue shed is not on the property. It is across the street. Final and best offers only. Acepting offers till Thursday 6pm.

Beds:
4
Baths:
2 Full
Sq.Ft.:
1,400
Status:
Active
MLS#:
MDQA147184
Type:
Single Family, Single Family-Detached
Subdivision:
Char Nor Manor
Lot size:
0.34 Acres
Year built:
2021
Courtesy: Long & Foster Real Estate, Inc.
View additional info

Beautiful 4 bedroom 2 bath in lovely Chestertown. Under Construction, but will be done within the month. An open kitchen to allow for all of the family to gather. Separate laundry room off of the kitchen. Master Bedroom has 2 large closets. This home has everything you need! Large family room, with lots of natural lighting. Settlement on date of completion.$1000.00 credit towards buyer if used preferred lender.

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