Chestertown MD Homes for Rent

The median home value in Chestertown, MD is $380,000. This is higher than the county median home value of $301,300. The national median home value is $338,100. The average price of homes sold in Chestertown, MD is $380,000. Approximately 42.33% of Chestertown homes are owned, compared to 50.71% rented, while 6.96% are vacant. Chestertown real estate listings include condos, townhomes, and single family homes for sale. Commercial properties are also available. If you see a property you’re interested in, contact a Chestertown real estate agent to arrange a tour today!


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Type:
Single Family-Detached
Sq.Ft.:
1,811
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1982
Baths:
2.00
MLS#:
MDQA2011886
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

Welcome to your dream home in the charming sought after community of Chester Harbor! This delightful property boasts 3 spacious bedrooms and 2 full updated bathrooms, perfectly designed for comfort and modern living. Step into the huge master bedroom, perfect for all buyers. The finished basement provides versatile additional living space—ideal for a family room, home office, or play area. The recently renovated kitchen is a culinary enthusiast’s dream, featuring contemporary finishes and high-end appliances that make meal prep a pleasure. Outside, the great yard is perfect for entertaining, gardening, or simply enjoying the serene surroundings. Enjoy the HUGE garage located in the rear of the property. Chester Harbor Community has a voluntary HOA ($30/year), which offers water access, a beach, community events, and a playground. Just around the corner is Round Top Park offering tennis, pickleball, and basket ball courts, a playground, and pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.99 Acres
Baths:
MLS#:
MDKE2004720

ADDITIONAL INFORMATION

Two secluded wooded lots with approximately an acre total. The existing homes on the property are of little value. The county does not have well or septic records so buyer would need to perform perc test to build. There is a 16' right of way to access which has not been maintained. Buyer to do any due diligence. Could be a great hunting property!

Type:
Other
Sq.Ft.:
930
Status:
Active
Beds:
3
Lot size:
1 Acres
Year built:
1959
Baths:
1.00
MLS#:
MDKE2004694
Subdivision:
Quaker Neck

ADDITIONAL INFORMATION

Great Investment Opportunity – Fixer-Upper on 1 Acre Lot Attention DIYers, investors, and renovators! This small home, located on a beautiful 1-acre lot, is a diamond in the rough, offering endless potential for the right buyer. Nestled in the quiet, rural setting of Quaker Neck just 1.5 miles from downtown Chestertown, this property is the perfect canvas for a major rehab project. The home, which is in need of significant repairs and updates, is being sold as-is, providing a great opportunity to bring your vision to life. Whether you're looking to restore it to its original charm or transform it into something entirely new, this property offers a solid foundation for your renovation ideas. Property Highlights: * 1-acre lot with plenty of space for expansion, gardening, or outdoor activities * Small house with potential to become a cozy retreat or a profitable rental * Quiet, rural location for privacy and peace of mind * Easy access to Chestertown for shopping and Quaker Neck Landing for water fun! Please note: This home needs extensive repairs and will not qualify for traditional financing, so it's ideal for cash buyers or those with renovation experience. Buyer to perform due diligence. Sellers are willing to provide architectural drawings & site plans for their planned renovation. Don’t miss this opportunity to turn a fixer-upper into your dream home or next big project. Schedule a showing today and imagine the possibilities!

Type:
Other
Sq.Ft.:
1,252
Status:
Active
Beds:
3
Lot size:
0.32 Acres
Year built:
1966
Baths:
1.00
MLS#:
MDKE2004712
Subdivision:
College Heights

ADDITIONAL INFORMATION

Brick rancher located on the corner of Greenwood and Glen Street in College Heights offers a large screened porch, eat-in kitchen and dining room. Home is convenient to downtown historic Chestertown , Washington College and hospital. Property is served with public water/sewer.

Type:
Single Family-Detached
Sq.Ft.:
1,114
Status:
Active
Beds:
3
Lot size:
0.34 Acres
Year built:
1965
Baths:
2.00
MLS#:
MDQA2011266
Subdivision:
Char Nor Manor

ADDITIONAL INFORMATION

An adorable cottage with water views of the Chester River! Nicely maintained cottage featuring 3 bedrooms, 2 full baths with all the big ticket items completed. Newer Well and Septic, HVAC and newer Metal Roof just leaves you with finishing touches on the interior as you see fit. Currently used as a rental. Also features a detached workshop and detached garage. If you are a boater, bring your boat and the Deep Landing Boat Ramp is just minutes away . Very affordable home in our area, don't wait on this one!

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.96 Acres
Baths:
MLS#:
MDKE2004648

ADDITIONAL INFORMATION

This prime commercial lot offers an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.96+/ -acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the town and county, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, depending on the town's planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to check with the town regarding specific zoning regulations, potential use, and public water/sewer hook-up fees to ensure a smooth development process. Whether you’re looking to expand your business or invest in a growing area, this lot offers the perfect foundation for success. Don’t miss out on this rare opportunity!

Type:
Single Family-Detached
Sq.Ft.:
3,355
Status:
Active
Beds:
5
Lot size:
0.91 Acres
Year built:
1963
Baths:
3.00
MLS#:
MDKE2004550
Subdivision:
Chesmar

ADDITIONAL INFORMATION

A highly coveted Chester River waterfront just minutes from Historic Downtown Chestertown. This large home has an ample sunroom overlooking the yard to the Riverfront, an in-ground pool within the 100' buffer, a dock with 3+ MLW, an expansive primary suite with sweeping water views, a private space for a home office, playroom, or in-law suite, and a detached three car garage for toys, vehicles, and storage. All situated on almost one full acre. Brand new upgrades since Sept '24 include central AC, roof, refinished hardwood floors, and paint throughout. With easy access to Morgnec Rd, Rt. 301 is only 12 minutes away... which leaves you only an hour's drive from Wilmington, DE or Philadelphia, PA. And into the heart of NYC in less than three hours. Escape to the Eastern Shore lifestyle!

Type:
Other
Sq.Ft.:
1,200
Status:
Active
Beds:
3
Lot size:
0.07 Acres
Year built:
2005
Baths:
3.00
MLS#:
MDKE2004698
Subdivision:
Hill Top

ADDITIONAL INFORMATION

Built in 2005, this beautifully maintained home offers modern comforts and an inviting atmosphere. The open floor plan on the main level features bright, airy spaces that seamlessly connect to a charming brick patio via sliding glass doors. With 3 bedrooms, 2.5 bathrooms, and 1,222 square feet of low-maintenance living, this home is designed for ease and comfort. Enjoy the convenience of two dedicated parking spaces right at your doorstep and the peace of mind that comes with no outdoor upkeep. The spacious living and dining areas flow effortlessly to the rear porch and shared common grounds, creating the perfect setting for relaxation or entertaining. Nestled in Chestertown, this home is ideally located near Washington College, Chester River Hospital Center, and the Chestertown walking trail, offering easy access to both local amenities and recreational opportunities.

Type:
Single Family-Detached
Sq.Ft.:
1,344
Status:
Active
Beds:
3
Lot size:
1 Acres
Year built:
2021
Baths:
2.00
MLS#:
MDQA2011794
Subdivision:
Blakefield

ADDITIONAL INFORMATION

This meticulously maintained 3-bedroom, 2-bathroom ranch-style home offers the perfect blend of comfort and modern features. Located in a tranquil setting that backs to farmland, it boasts an open floor plan with cathedral ceilings, creating a spacious and airy atmosphere throughout. The upgraded kitchen with stainless steel appliances that make it ideal for both cooking and entertaining. The upgraded flooring adds elegance and durability to the home, while the energy-efficient tankless water heater ensures a continuous supply of hot water. Whether you're relaxing in the living area, enjoying the views of the surrounding farmland, or hosting guest in the open space, this home is designed for modern living. It's truly a must-see for anyone seeking a move-in ready home. 1 acre lot

Type:
Single Family-Detached
Sq.Ft.:
1,380
Status:
Active
Beds:
3
Lot size:
0.35 Acres
Year built:
2005
Baths:
2.00
MLS#:
MDQA2011746
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

Welcome to Chester Harbor - a family oriented place to live! The Chester Harbor Community has a voluntary HOA of $30/year, which offers water access, a beach, community events, and a playground. Close by is Round Top Park offering tennis, pickleball, and basketball courts, a playground, and a pavilion. Minutes from Chestertown's historic waterfront, restaurants, shopping, and marinas. Queen Annes County Schools! Comfortable serene and convenient - this well cared for home has hardwood floors and a new hot water heater and water tank on 3/11/2023 and an attached workshop!

Type:
Single Family-Detached
Sq.Ft.:
1,900
Status:
Active
Beds:
3
Lot size:
1 Acres
Year built:
2024
Baths:
3.00
MLS#:
MDQA2011774
Subdivision:
Blakefield

ADDITIONAL INFORMATION

Brand New Gorgeous Custom Home ready Jan 1st. Possible closing help! Fall in love with the 1st floor bedroom/bath/WIC, 2 car garage, gourmet kitchen with large island & granite counters, cathedral ceilings, huge family room, 1st floor laundry, front porch, sky-basement on 2nd floor for storage, 2 large bedrooms and full bath on second floor. This great floor plan is hard to find with all of these upgrades and is perfectly situated on an acre lot in a beautiful country setting. Relax and watch the sun rise or set as you boast to your family & friends about this amazing house you just bought. Great country location near the Chester River, boat ramps, beaches, parks, hospitals, restaurants, shopping. Convenient to the beaches, Dover, Middletown, Annapolis & DC/Balt. Won't last long! Co-owner/RE agent.

Type:
Retail
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.49 Acres
Year built:
1997
Baths:
MLS#:
MDKE2004690
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

Type:
Retail
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.49 Acres
Year built:
1997
Baths:
MLS#:
MDKE2004688
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

Type:
Retail
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.49 Acres
Year built:
1997
Baths:
1.00
MLS#:
MDKE2004686
Subdivision:
Downtown Chestertown

ADDITIONAL INFORMATION

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.93 Acres
Baths:
MLS#:
MDKE2004650

ADDITIONAL INFORMATION

This prime commercial lot offers an exceptional opportunity for your next business venture. Situated at the highly visible corner of Scheeler Road and Haacke Drive, this 0.93+/- acre parcel is zoned C-1, which allows for a variety of commercial uses. With limited commercial land available in the County, this is a rare find in a desirable location with great potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, depending on the town's planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to check with the town regarding specific zoning regulations, potential use, and public water/sewer hook-up fees to ensure a smooth development process. Whether you’re looking to expand your business or invest in a growing area, this lot offers the perfect foundation for success. Don’t miss out on this rare opportunity!

Type:
Other
Sq.Ft.:
1,930
Status:
Active
Beds:
3
Lot size:
0.09 Acres
Year built:
2004
Baths:
3.00
MLS#:
MDKE2004566
Subdivision:
Oak Hollow

ADDITIONAL INFORMATION

Rare end unit townhome in Oak Hollow. Close to shopping and college. Spacious rooms. Open kitchen with granite counters and a kitchen island. Sliders to patio and to upper level deck. Large yard. Half bath on the main floor. 3 bedrooms and 2 full baths on the upper floor. Family room in the basement as well as an oversized 1 car garage with lots of storage. Roof has recently been replaced. Overall, a great unit in a great location!

Type:
Single Family-Detached
Sq.Ft.:
1,288
Status:
Active
Beds:
3
Lot size:
0.38 Acres
Year built:
2018
Baths:
2.00
MLS#:
MDKE2004654
Subdivision:
Quaker Estates

ADDITIONAL INFORMATION

This charming 3-bedroom, 2-bath rancher nestled in a serene setting of Quaker Estates is a gem you won't want to miss! This modern 2018 home offers a perfect blend of comfort and style on a back corner lot with scenic trees on two sides. The perfect split bedroom design with large open central living room, kitchen, and dining with generous space perfect for gatherings. Durable vinyl laminate flooring with the exception of the two smaller bedrooms are carpet. The primary bedroom is a peaceful retreat with an en-suite bathroom, offering privacy and convenience. Enjoy time outside on the expansive 16 x 32 deck for outdoor gatherings and relaxation. Two nice storage sheds for your lawnmower and tools, raised garden bed, play area and a separate spot for your camper. This home shows like new and won't last long. This home offers close proximity to all downtown amenities, schools, and parks and is only 25 minutes to Middletown's shopping, dining, and entertainment options. Don't miss the opportunity to make this delightful rancher your own. Schedule a private showing today and envision the possibilities of living in this beautiful home! Private well and public sewer.

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
2.2 Acres
Baths:
MLS#:
MDKE2004652

ADDITIONAL INFORMATION

Desirable wooded country 2.2 acre building parcel located near public boat landings between Chestertown and Rock Hall. Recorded plat with perc denoted on the plat signed by Health Department Officer in 1994. Lots of wildlife in the area. Perfect location to build your new home back off the road in a convenient location. Maybe even have your own deer stand! Plat is filed in Kent County Land Records in Plat Book MLM liber1, Folio 391 dated 6/19/1995.

Type:
Single Family-Detached
Sq.Ft.:
3,684
Status:
Active
Beds:
4
Lot size:
2.62 Acres
Year built:
2000
Baths:
4.00
MLS#:
MDKE2004586
Subdivision:
None Available

ADDITIONAL INFORMATION

Welcome to your serene getaway nestled on 2.62 acres of partially wooded land on Urieville Lake! This stunning 4-bedroom, 3.5-bathroom home offers the perfect blend of comfort and privacy, making it an ideal retreat for families and nature enthusiasts alike. With an option of a first floor bedroom there are currently three bedrooms on the second floor and one unofficial bedroom in the basement, there’s plenty of space for family and guests. The open-concept living area is perfect for gatherings, featuring ample natural light and gorgeous views of the surrounding landscape & lake! Enjoy convenience and comfort with two full bathrooms on the second, one full bath on the lower level and an additional half bath on the first, designed with modern fixtures and finishes. The finished walk-out basement provides excellent additional living space, bath/bedroom & perfect for a game room, entertainment area, or a private office. It also offers direct access to the beautiful outdoors. The property spans 2.62 acres, providing ample room for outdoor activities, gardening, or simply unwinding in nature. The partially wooded area enhances your privacy while allowing for serene nature walks right in your backyard & along the Lakes edge! Located on Urieville Lake, enjoy fishing, boating, and other recreational activities just moments from your doorstep. This private setting is perfect for those looking to escape the hustle and bustle of city life. Urieville Lake is about 35 acres in size and is shaped like the letter Y. The average depth is about 3 feet and supports a standard bass/bluegill fishery and is managed accordingly. Anglers may also occasionally catch other species including pumpkinseed sunfish, brown bullhead catfish, golden shiners and common carp. Interior pictures and layout coming soon!

Type:
Single Family-Detached
Sq.Ft.:
3,280
Status:
Active
Beds:
3
Lot size:
10.01 Acres
Year built:
1920
Baths:
2.00
MLS#:
MDKE2004580
Subdivision:
None Available

ADDITIONAL INFORMATION

Nestled on 10 scenic acres just outside of Chestertown, this spacious 3,280 sq ft home offers incredible potential for those looking to earn a little sweat equity. This home is ready for a buyer looking to uncover its true potential. Boasting 3 large bedrooms, a very large room on 2nd level could be a bedroom ? game room ? you decide, 3 flexible spaces that can be used as offices, dens, or multi-purpose rooms, and oversized rooms throughout that offer endless possibilities for customization. Rich hardwood floors and custom doors and woodwork add character and charm, while a full-length sunroom across the front of the house provides stunning views of the surrounding landscape. The spacious kitchen features Amish-built cabinetry, offering both craftsmanship and timeless appeal, along with a large pantry for added storage. The generously sized laundry room offers added convenience. There is so much storage space offered throughout this home. walk in closets, etc. The property includes an outdoor wood furnace (central boiler system), a whole-house propane generator, a shed, large circular driveway and several outbuildings one with small studio space providing ample space for storage, workshops, or hobbies. There is also future development potential with upcoming zoning changes from Rural Character to Community Residential - think subdivision . Please verify all zoning and development opportunities directly with the County. This is a unique opportunity to invest in a property with endless potential—whether you're looking for a personal retreat , a large piece of land to call your own, or a long-great investment. Don’t miss your chance to make this property your own! Home is being sold AS IS.

Type:
Single Family-Detached
Sq.Ft.:
2,408
Status:
Active
Beds:
5
Lot size:
0.8 Acres
Year built:
1976
Baths:
4.00
MLS#:
MDKE2004638
Subdivision:
Heather Heights

ADDITIONAL INFORMATION

This impeccably maintained home is a true standout and has it ALL! With 5 spacious bedrooms - with both main level & upper level primary suites - and 3.5 baths, including a main level primary suite with a walk-in closet featuring a premium wood built-in system, dual vanity, and a double-headed walk-in tiled shower. This home offers both luxury and convenience. The updated kitchen is an ideal space, with granite countertops, stainless steel appliances, a stylish tile backsplash, and 2015 KraftMaid cabinetry in a stunning navy blue. Every room is thoughtfully painted and wallpapered, adding character to the gleaming hardwood floors and plush, high-quality carpets throughout. The home also boasts an updated HVAC system and a brand new asphalt driveway. The basement includes a rec room and ample storage space, while the expansive 0.8-acre lot overlooks serene pastoral farmland, with a beautiful hardscaped patio perfect for outdoor entertaining. Best of all, this home is located under 1.5 miles from the heart of downtown Chestertown, so you’re just minutes away from shopping, dining, and all the charm the town has to offer.

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
2.36 Acres
Baths:
MLS#:
MDKE2004490

ADDITIONAL INFORMATION

Pretty wooded parcel recently surveyed with stakes clearly showing property boundaries. SEE DOCUMENTS for plat and aerial view. Property already has a sewer allocation. Tax record shows 3 acres but recent survey confirms 2.356 acres. There is an old collapsed trailer on site that did have electric at one time. Seller is in the process of removing the trailer and any debris around the trailer so the property will be back in pristine condition soon! This area has also been know for excellent hunting (owner recently took down a couple of deer). Property sits back off the road with a wide gravel right of way back to the parcel. The seller will meet interested parties on Georgetown Rd where a chain is across the right of way. Do not walk the property without the seller or his agent, especially during hunting season.

Type:
Single Family-Detached
Sq.Ft.:
1,470
Status:
Active
Beds:
4
Lot size:
0.8 Acres
Year built:
1978
Baths:
2.00
MLS#:
MDQA2011362
Subdivision:
Chester Harbor

ADDITIONAL INFORMATION

Adorable and Affordable in Chester Harbor community! This 4-bedroom 2 bath home is ready for you! situated on a .8-acre level lot that backs to trees and open fields, this home offers a private retreat in a sought-after Water oriented community. There is a large Country Kitchen with room for table and chairs. Laundry in Kitchen is convenient and easy to access. Main level has two bedrooms and 2 baths while the finished lower level offers plenty of space and 2 bedrooms. Come and enjoy the tranquil and walkable neighborhood that is close to Chestertown and offers Queen Annes County Schools!

Type:
Land
Sq.Ft.:
n/a
Status:
Active
Beds:
n/a
Lot size:
0.09 Acres
Baths:
MLS#:
MDKE2004610

ADDITIONAL INFORMATION

ONLINE AUCTION: Bidding begins 1/17/25 @ 10:00 AM. Bidding ends 1/21/25 @ 12:10 PM. List Price is Suggested Opening Bid. Lot of land in Tolchester Beach, Maryland located within Kent County. Nearby attractions include Tolchester Marina and +/- 7 miles to all the attractions in Rock Hall, Maryland. Easy Access to Major Traffic Artery Rock Hall Road. Deposit: $5,000.

Type:
Other
Sq.Ft.:
1,420
Status:
Active
Beds:
3
Lot size:
0.06 Acres
Year built:
2023
Baths:
3.00
MLS#:
MDKE2004524
Subdivision:
The Village At Chestertown

ADDITIONAL INFORMATION

Welcome home this beautiful end unit townhome in the newer community of The Village At Chestertown. This 3 bedroom, 2.5 bath townhome looks out over the beautiful pond with fountain, and a great walking path around the pond and community. Furry friends are welcome at the nearby dog park as well. This home is less than a year old and has had some upgrades added since the purchase, such as the maintenance free fully fenced back yard, ceiling fans, upgraded light fixtures, upgraded bathroom vanities, kitchen faucet, hardware, and more! Easy commute to Rt. 301, and the brand new YMCA is right around the corner! Enjoy Chestertown with it's small town charm, great restaurants, artistic venues, and close to Washington College. Schedule your tour today!

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Andrea Conner, Maryland License 667140, Xome Inc., License 667140, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, D.C. License BR200200783, Xome Inc., License CO98372739, [email protected], 844-400- 9663, 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, PA License # RM425337, Xome Inc., PA License #RB067821, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067
Andrea Conner, NJ License # 1758875, Xome Inc. NJ License # 2326449, [email protected], 844-400-XOME (9663), 750 State Highway 121 Bypass, Suite 100, Lewisville, TX 75067

© BRIGHT, All Rights Reserved - The data relating to real estate for sale on this website appears in part through the BRIGHT Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms in which Xome Inc. participates, and is provided by BRIGHT through a licensing agreement. Some real estate firms do not participate in IDX and their listings do not appear on this website. Some properties listed with participating firms do not appear on this website at the request of the seller. The information provided by this website is for the personal, non-commercial use of consumers and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on this website may no longer be available because they are under contract, have Closed or are no longer being offered for sale. Home sale information is not to be construed as an appraisal and may not be used as such for any purpose. BRIGHT MLS is a provider of home sale information and has compiled content from various sources. Some properties represented may not have actually sold due to reporting errors.

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