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 ...

Brand new home in Historic Chestertown available for move-in now. This interior unit features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitch...

Welcome to easy, move in ready living in the heart of Chestertown! This fully renovated townhouse offers modern updates, low maintenance living, and an unbeatable locatio...

Welcome to this spacious brick rancher located in the desirable Country Club Estates neighborhood, offering over 2,800 square feet of beautifully updated living space in ...

Welcome to easy, one-level living in a location that truly gives you the best of both worlds! Just minutes from the charm and downtown, walkable, waterfront lifestyle of ...

Recently updated "coastal" home located in a small community of 8 homes , three miles east of historic Chestertown. The house sits on high ground, less than a mile from...

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with ...

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...

Affordable opportunity in the heart of downtown Chestertown! This 3-bedroom, 1.5-bath townhome is ideally located just minutes from Washington College, shops, restaurants...

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!

AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. This beautifully renovated 3-bedroom, 2-bath Fairlee home is a true gem, perfectly situated on a private 2-acre lot tha...

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...

Price Improvement! Now offered at $239,900 Welcome to 104 Conley Drive in the heart of Chestertown! This move-in ready 3-bedroom, 1.5-bath townhome offers comfortable, lo...

Gorgeous house on River Rd in the Queen Anne's County side of Chestertown. 3 total bedrooms and 2.5 baths. The main bedroom is on the first floor. Stunning sun room, pa...

Embrace Eastern Shore living in this beautifully designed Oak Hollow townhome. Offering 1,900 square feet of spacious, three-level living, this property is perfectly posi...

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 ...

Welcome to country living ! Nestled on over an acre, this solid brick rancher offers nearly 2,000 square feet of living space with many possibilities. Enjoy the peace and...

Nice basic rancher offering 3 bedrooms and a full bath, generous sized living room with a large window allowing plenty of light in. The kitchen has an eat-in counter sp...

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 102 Flying Cloud a new community known as The Village of Chestertown. This is a rare opportunity to own a home at this price and condition. Designed to with an...

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...

If you're looking for that secluded spot, with land, room to grow and stretch, and don't mind a project, look no further! Dream location on a private road, backing to far...

Brand new home in Historic Chestertown available for move-in now. This home features luxury vinyl plank flooring throughout, a spacious living room, eat-in kitchen with ...

Welcome to Tolchester Estates, a charming community near the Chesapeake Bay. This 3-bedroom, 2-bath rancher features updated HVAC, gas cooking, an upgraded propane hot wa...

Practically brand new and just 2 years young with access to the Chester River, this beautifully maintained home is perfectly situated in a desirable water-oriented commun...

Newly constructed three-bedroom townhome with fantastic water views from the living level and bedrooms! Spacious open living space featuring a gourmet kitchen; 5-burner ...

Charming and inviting! Welcome to 139 Prospect St., a delightful 3-bedroom, 1-bath rancher offering approximately 1,200 square feet of comfortable living space. This well...

Tucked away just south of the scenic Chester River and moments from the timeless charm of Chestertown, this inviting home offers a warm and welcoming retreat in the heart...

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...

Custom builder selling his own home that has been well built, well maintained, and thoughtfully designed. This home is in great condition and offers just under 3,000 squa...

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

**To be built! Welcome to this beautifully designed 1,964 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The ...

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The ...

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms an...

**To be built! Welcome to this beautifully designed 2,092 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The ...

**To be built! Welcome to this beautifully designed 2,231 sq ft home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The h...

**To be built! Welcome to this beautifully designed 1,980 sq ft home in Chester River Landing, offering modern comfort and timeless style. The home includes 3 bedrooms a...

Three bedroom one-floor living on a spacious lot in Chester Harbor! Over half an acre of nicely shaded yard space, and a short distance to the public beach on Mill Creek....