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

104 Church Aly, Chestertown $440,000

A perfect pied-a-terre or full time residence, this adorable historic home is just steps from the farmers market, shops, restaurants, theater,art galleries and the Cheste...

2 Beds
2 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

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

Sandpiper Rd, Chestertown $4,500

Recreational lot- access community amenities, bird watch, garden, make a trail, firewood, etc. Not buildable unless the county adds public sewer in the future. RVs are no...

Courtesy of Chesapeake Real Estate Associates, LLC

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

129 Trafford Dr, Chestertown $480,000

PICTURES COMING SOON Welcome home to this beautiful 3-bedroom, 2.5-bath residence in the charming town of Chestertown, MD. Designed for both comfortable living and effor...

3 Beds
3 Baths

Courtesy of Elevated Real Estate Solutions

Listing courtesy of Elevated Real Estate Solutions. Contact: 3024222619

10540 Tonopah Rd, Chestertown — Chesapeake Landing $279,000

Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a priv...

3 Beds
2 Baths

Courtesy of Doug Ashley Realtors, LLC

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

7903 Radcliffe Rd, Chestertown $625,000

This exceptional property offers classic charm, thoughtful updates, and a highly desirable location in a neighborhood where homes rarely become available. No trendy updat...

3 Beds
4 Baths

Courtesy of Chesapeake Real Estate Associates, LLC

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

202 Pine St, Chestertown $205,000

Investor special! This property needs to be fully rehabbed. Great location in the highly sought after neighborhood college Heights. A diamond in the rough and ready for n...

3 Beds
1 Baths

Courtesy of Coldwell Banker Chesapeake Real Estate Company

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

1010 Twin Ct, Chestertown $375,000

Adorable 4 bedroom 2 bathroom Cape Cod in the quiet Crestview neighborhood in Chestertown close to Restaurants, Shopping, the brand new YMCA and the Historic Downtown. E...

4 Beds
2 Baths

Courtesy of Kevin Dey Realty

Listing courtesy of Kevin Dey Realty. Contact:

21146 Montana Ave, Chestertown $289,900

Escape to the Eastern Shore! Nestled among mature trees on a .41 acre wooded lot, this charming Cape Cod-style home offers the perfect blend of privacy, comfort, and East...

2 Beds
2 Baths

Courtesy of Cross Street Realtors LLC

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453

104 Maple Ave, Chestertown $650,000

List Price is opening bid. Online Auction Only! Bidding begins Saturday, August 22nd and ends Thursday, August 27, 2026 at 12:00 PM. Exceptional Multi-Family Investment O...

Courtesy of Alex Cooper Auctioneers, Inc.

Listing courtesy of Alex Cooper Auctioneers, Inc.. Contact:

8312 Broad Neck Rd, Chestertown $380,000

Bring your vision and transform this unique property into the home of your dreams. Situated on 3.79 picturesque acres, the property features a beautiful one-acre stocked ...

3 Beds
2 Baths

Courtesy of Pearson Smith Realty, LLC

Listing courtesy of Pearson Smith Realty, LLC. Contact: 5713861075

201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown image

201 N Lynchburg St Unit #LOTS 4, 5, 6 & 7, Chestertown $300,000

4 Vacant Lots with many possiblilites. The project has the potential for a density change for 10 or more units. Buyer should do all necessary due diligency. Can also be s...

Courtesy of RE/MAX Associates-Hockessin

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800

201 N Lynchburg St, Chestertown $500,000

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered separately or together. Located in the heart of Cheste...

Courtesy of RE/MAX Associates-Hockessin

Listing courtesy of RE/MAX Associates-Hockessin. Contact: 3022343800