Chestertown Real Estate

Welcome to Chestertown, Maryland—a charming riverside town that beautifully blends history, culture, and a vibrant community spirit. Nestled in Kent County along the scenic Chester River, Chestertown offers a picturesque setting that captivates both residents and visitors alike.

Founded in the 18th century, this historic town boasts a rich heritage, with well-preserved architecture that transports you back in time. Stroll along the cobblestone streets and admire the elegant Georgian and Federal-style homes, many of which date back to the colonial era. The town's commitment to preserving its history is evident in landmarks like the Chestertown Historic District, which is listed on the National Register of Historic Places.

Chestertown is not just about history; it's a hub for arts and culture. The town hosts a variety of events throughout the year, including the renowned Chestertown Tea Party Festival, celebrating its revolutionary roots, and the RiverArts organization, which showcases local artists and craftspeople. Outdoor enthusiasts will find plenty to love here, too. The Chester River offers opportunities for kayaking, sailing, and fishing, while the surrounding countryside invites hiking and biking adventures.

With a friendly, close-knit community, Chestertown is a place where neighbors become friends. Families are drawn to its excellent schools and safe environment, while retirees enjoy the serene pace of life. Whether you’re looking to settle down or simply visit, Chestertown welcomes you with open arms and a promise of unforgettable experiences. Come explore this hidden gem on Maryland's Eastern Shore, where history meets hospitality!

Newest Listings in Chestertown

10 Cedar Chase Ct, Chestertown $495,000

Beautiful waterviews of the Chester River set the stage for this special Chestertown property, located in desirable Mile Tree Village and just a short walk from the Histo...

3 Beds
3 Baths

Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

6324 Quaker Neck Rd, Chestertown $2,895,000

Discover 6324 Quaker Neck Road, an exceptional waterfront estate spanning over 5 acres along the East Fork of Langford Creek offering over 5 feet of water at low tide. Ov...

5 Beds
4 Baths

Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

22974 Bay Shore Rd, Chestertown $329,900

Welcome to this charming farmhouse-style home in Fairlee! Completely renovated in 2023, this home is move-in ready and offers a comfortable mix of modern updates and farm...

2 Beds
2 Baths

Courtesy of Benson & Mangold, LLC

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665

105 N Water St Unit #3, Chestertown image

105 N Water St Unit #3, Chestertown $489,000

Second story, waterfront condo in historic Chestertown. Private boat slip. Many more details and pictures to come. Stay tuned! You won't want to miss this!

2 Beds
2 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

7712 Waterview Ln, Chestertown $659,999

Live where you play at 7712 Waterview Lane in sought-after Country Club Estates. Situated on just under an acre, this beautifully renovated, well-maintained Cape Cod is ...

3 Beds
4 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

8732 Elm Rd, Chestertown $289,000

Located in Tolchester Estates, this well maintained ranch style home sits on a lovely tree shaded lot. There are three bedrooms, two bathrooms and an open kitchen, dining...

3 Beds
2 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

Listing courtesy of Coldwell Banker Chesapeake Real Estate Company. Contact:

104 Maple Ave, Chestertown $1,050,000

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Courtesy of Real Broker, LLC - Annapolis

Listing courtesy of Real Broker, LLC - Annapolis. Contact: 8554500442

8276 Broad Neck Rd, Chestertown $1,295,000

Step into your own private world, just 2.75 miles from Historic Downtown Chestertown. Tucked away at the rear of a mostly wooded 19+/- acre parcel, this exceptionally wel...

4 Beds
4 Baths

Courtesy of Select Land & Homes, LLC

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

223 Mount Vernon Ave, Chestertown $200,000

Investors, contractors & handy buyers—this is the fixer-upper opportunity you’ve been waiting for! This 4 bedroom downtown Chestertown diamond in the rough offers strong ...

4 Beds
1 Baths

Courtesy of Chesapeake Real Estate Associates, LLC

Listing courtesy of Chesapeake Real Estate Associates, LLC. Contact:

Chestertown $695,000

Rarely do vacant parcels like this become available so close to historic Chestertown! Offering approximately 43 acres, this exceptional property presents a unique opportu...

Courtesy of Select Land & Homes, LLC

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956

Towhee Rd, Chestertown $50,000

This property, situated on a 0.55-acre lot, offers a blank canvas for your vision. Located in Kent County, this property presents endless possibilities for the right buye...

Courtesy of The Parker Group

Listing courtesy of The Parker Group. Contact: 3022176692

27942 Old Morgnec Rd, Chestertown $89,000

Very private 5+ acre parcel with well and perc approved septic. Just minutes from Chestertown and very easy access to points north and south via route 301

Courtesy of Gunther-McClary Real Estate

Listing courtesy of Gunther-McClary Real Estate. Contact: