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...

A rare turnkey, profitable, investment property in downtown Chestertown. Renovated to the studs in 2022, 200-202-204 High Street has 5 apartments and 3 storefronts and s...

Welcome to this beautifully renovated 2-bedroom, 1-bath townhome offering the perfect blend of comfort, style, and convenience. Completely updated from top to bottom, thi...

Welcome to 10720 Foreston Rd, a charming and inviting home situated in the peaceful surroundings of Chesapeake Landing in Chestertown, MD. 3 bedrooms and 2 full bathroom...

Charming Single-Level Home in the Heart of Walkable Chestertown. Welcome to one of Chestertown's most convenient addresses — a quaint, single-level, three-bedroom home se...

Looking for peaceful country living? The search is over! Nestled on 1.66 acres, this beautifully renovated 3-bedroom, 1.5-bath home offers the perfect blend of comfort, f...

A rare find! This rancher on Washington Ave has dual use: zoned residential and commercial. Full finished basement. More details and pictures coming soon!

Experience the warmth and charm of in-town living in this beautiful residence in Chestertown's Historic District. Just a few blocks from the waterfront, shops, galleries,...

Open House Friday July 3rd 4-6pm! Located on Water Street in the heart of Chestertown's premier waterfront historic district, this beautiful two-bedroom, two-bath condomi...

An exceptional opportunity to own this Single Level 3 bedroom 1 full bathrooms Ranch Style Home at a GREAT price nestled on an adorable lot. No need to worry about climbi...

The Pearce House has been a testament to fine Eastlake Victorian architecture since it was constructed by famous early Eastern Shore builder H.M. Stuart for Judge James P...

This cute as a button downtown stunner is recently updated and ready for the next owner to fall in love with the lifestyle that comes with living in the Historic District...

Investor Special – Charming Colonial in Prime Chestertown Location! Welcome to 234 N College Ave, an adorable colonial full of character and potential, nestled in the he...

Charming Brick Rancher Near the Chester River This custom-built brick rancher sits in a nice Chestertown neighborhood with excellent curb appeal, a classic hipped roof, a...

Investor Alert - Classic 2-Story Colonial Packed with Potential! Welcome to this Charming Colonial Offering the Space, Layout, and Bones that Savvy Buyers Dream of. The ...

Desirable in-town living in a peaceful neighborhood. This solid brick front rancher was totally renovated in 2022 and is still like New. The pictures tell the story. Eas...

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the...

Wake up to sweeping views of the Chester River and end each day with spectacular western sunsets from this exceptional waterfront. Situated on 0.61 acres with 169 feet +/...

✨ Historic Charm in the Heart of Downtown Chestertown ✨ Step back in time and discover the character, craftsmanship, and endless potential of this circa-1820 historic ho...

Circa 1743 with a stately 1825 addition, The Inn at Mitchell House is a rare pre-Revolutionary manor home on 9+ manicured acres on Maryland's Eastern Shore. Listed on the...

Welcome to the epitome of Eastern Shore waterfront luxury, offered for the first time in almost 60 years. This stunning 11-acre estate offers an unparalleled lifestyle, f...

Welcome to this charming 4-bedroom rancher nestled in the heart of historic Chestertown, offering the perfect blend of peaceful rural living and convenient access to town...

Built in 1780/1840, "Highcroft" is in the heart of the Historic District near the Chester River. A rare in-town property that offers a 2-car garage with a second floor an...

MOVE IN READY!! Adorable, Affordable, move in ready & two blocks from the Chesapeake Bay! Appliances, roof, waterproof vinyl plank flooring, stove, dishwasher recently ...

Built Before America: A Pre-Revolutionary Home in the Heart of Chestertown's Historic District The Bedingfield Hands House, circa 1750, is more than a home—it's a living ...

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

117 N Water Street, originally built prior to the mid-1800s, is an incredible opportunity to own a small slice of Downtown Chestertown, or to dive into the investment asp...

**Listing price is for ALL FOUR available units for sale as an investment package! Pricing for each unit and their details are below. 117 N Water Street, originally buil...

Currently used as a church and in the Downtown Residential R-5 zoning. This sale also includes 5 additional residential lots.

A great opportunity for community mission driven organizations. The church and 5 additional parcels are all offered together. Located in the heart of Chestertown, this ch...

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What used to be known as the 'Pomona Store' is back on the market with fresh updates throughout! 4 bedroom house with in-law suite (additional 2 rooms on main level) and ...

Rebuilt in 1863, the Tilley Residence showcases classic Second Empire architecture on one of Chestertown’s most prominent historic corners across from the Custom House, o...

ALSO AVAILABLE FOR LEASE: Please reach out to agent for details. This charming 1916 home in Chestertown's historic district is in a quiet neighborhood next to Washington...

Price Improvement! Spectacular waterfront on the Chester River!! Words can't describe the uniqueness of this property. With the historic charm of an older home but hig...

Commercial Development Site on busy MD Rte 213, Prime location across from new Starbucks and Washington College Campus. Approx 1 acre, zoned C-3. Suitable for retail, re...