High's, Chestertown, MD, USA

Chestertown, Maryland, United States

Name: High's
Address: Chestertown, Maryland, United States

Homes for sale near High's, Chestertown, MD, USA

Address	Bed / Bath	Listing Price
204 ROLLING ROAD Live with ease in this beautifully updated and maintained one floor home in downtown Chestertown. The current owners put a large addition on the house that includes a family room with wood burning stove, sunroom, and primary suite with en suite bathroom and walk in closet. A large laundry room on th CHESTERTOWN, MD Living Area: 2296 Sqft.	3 Beds, 2 Baths	$370,000
112 SILVER HEEL DRIVE AGENTS - PLEASE VIEW AGENT REMARKS IN BRIGHT MLS. Welcome to this stunning 2023 built home — a move-in ready, three-story residence offering 5 bedrooms and 3.5 baths across 2,615 sq ft of thoughtfully designed space. The first floor features an open layout with a spacious family room, dining area CHESTERTOWN, MD Living Area: 2615 Sqft.	5 Beds, 4 Baths	$250,000
222 MOUNT VERNON AVENUE LOCATION! This stunning 4-bedroom, 2-full-bath home is just steps from Washington College and a short stroll to downtown Chestertown. This treasure is full of historic character blended with modern updates! Sellers have INVESTED $60,000 IN RECENT UPGRADES this year, including a brand NEW roof, new CHESTERTOWN, MD Living Area: 1656 Sqft.	4 Beds, 2 Baths	$499,999
304 HADAWAY DRIVE Welcome to 304 Hadaway Dr. This classic home has been completely reimagined and is ready for it's next chapter. Entering the home you will immediately notice the beautifully refinished original hardwood floors. As you make your way down the hallway past the newly renovated hall bath with custom ti CHESTERTOWN, MD Living Area: 1325 Sqft.	4 Beds, 2 Baths	$425,000
303 E CAMPUS AVENUE Charming Brick Rancher in the Heart of Chestertown Discover this classic brick rancher nestled in one of Chestertown’s established neighborhoods. Enjoy the convenience of being just a short walk or bike ride from downtown, where you’ll find favorite local shops, restaurants, and the beloved Sat CHESTERTOWN, MD Living Area: 1532 Sqft.	3 Beds, 2 Baths	$363,000
318 LINCOLN Kent County welcomes you with a move-in ready home that’s full of updates! This 3-bedroom, 2-bath home sits on nearly a half-acre and is just minutes from downtown Chestertown. Enjoy peace of mind with a newer roof (approximately 5 years old), central heat and air, and a tankless water heater. The CHESTERTOWN, MD Living Area: 960 Sqft.	3 Beds, 2 Baths	$269,000
411 GREENWOOD AVENUE Experience the best of in-town Chestertown living in this custom-built single-level home! The open floor plan features abundant natural light, gleaming hardwood floors and a bright, inviting layout perfect for entertaining or relaxing. The dining room is open to the kitchen which includes some updat CHESTERTOWN, MD Living Area: 1676 Sqft.	3 Beds, 3 Baths	$419,000
101 BIRCH RUN ROAD Welcome to 101 Birch Run Rd., Chestertown, MD! 3 Bedrooms \| 2 Full Baths \| Oversized 2-Car Garage \| .42 Acres Discover this stunning full-brick rancher located in the heart of historic Chestertown! Every inch of this 3-bedroom, 2-bath home has been completely updated with a sophisticated modern fla CHESTERTOWN, MD Living Area: 1961 Sqft.	3 Beds, 2 Baths	$499,999
107 MALONE AVENUE Welcome to 107 Malone Ave. in the friendly community of Foxley Manor....A Great place to call "HOME"! This lovely 3 Bedroom, 1 Bath home is ready for you to make new memories, grow your family or downsize while enjoying single level living. Hardwood Floors throughout the living room and bedrooms ha CHESTERTOWN, MD Living Area: 1200 Sqft.	3 Beds, 1 Bath	$290,000
206 VALLEY Price improvement! Prepare to be wowed when you walk through the front door. Gleaming hardwood floors, huge floor-to-ceiling windows, high-end kitchen and primary bath. Floor plan that flows beautifully. 4 bedrooms and 2 baths. Wood burning fire place in the living room. House is filled with natu CHESTERTOWN, MD Living Area: 2869 Sqft.	4 Beds, 2 Baths	$615,000
100 ADELA WAY Days on Market Reporting Incorrectly- Property listed Oct 30, 2025 Nestled just outside of historic Chestertown, minutes from farmers market, waterfront park and local shops and eateries. This home offers the best of small-town living with modern updates at every turn. Step inside to discover woo CHESTERTOWN, MD Living Area: 3799 Sqft.	4 Beds, 4 Baths	$515,000
116 HARLAN LOOP $$THE OWNER MUST RELOCATE. TAKE ADVANTAGE OF THE NEW PRICE IMPROVEMENT! $$ Welcome to Coventry Farms in Chestertown — where comfort, elegance, and space come together in this stunning colonial-style home! Built in 2009 and meticulously maintained, this spacious property offers over 4,000 square f CHESTERTOWN, MD Living Area: 4067 Sqft.	5 Beds, 4 Baths	$519,000
103 ADELA WAY Looking for a large spacious home in a lovely neighborhood that is close to downtown & shopping, 20 min from Rt. 301, within 2 miles of the Chester River...Look no further! 3 Floors of living space, 4 - possibly 5 Bedrooms, 3 Full & 1 -1/2 Baths. Enter in through this spacious well-lit foyer which CHESTERTOWN, MD Living Area: 5576 Sqft.	4 Beds, 4 Baths	$595,000
907 N MEADOWVIEW DRIVE JUST INSTALLED BRAND NEW CARPET! Welcome to 907 N Meadowview Drive, a beautifully maintained home in the sought-after Crestview community of Chestertown. Situated on a spacious .707-acre lot, this 3-bedroom, 2.5-bath home offers 1,842 square feet of comfortable living space. Step inside to find a CHESTERTOWN, MD Living Area: 1842 Sqft.	3 Beds, 3 Baths	$410,000
251 DEVON DRIVE Welcome to 251 Devon Drive located in the desirable Coventry Farms neighborhood. When entering the paved circular driveway, you will find the property meticulously landscaped. The inviting curb appeal welcomes you into the home's foyer where you will find a living room to the left and formal dini CHESTERTOWN, MD Living Area: 3935 Sqft.	3 Beds, 3 Baths	$595,000
141 PROSPECT STREET INTOWN Investor Special! This 4-bedroom, 1.5-bath bungalow is full of potential and ready for your vision. Situated on a large, private lot at the end of a quiet street, the home offers solid bones and a detached garage/workshop area that is hard to find! Located just minutes from Chestertown and Wa CHESTERTOWN, MD Living Area: 1156 Sqft.	4 Beds, 2 Baths	$167,000
132 PROSPECT STREET Priced To Sell Fast! Renovate & Resell or Buy & Hold, Desirable 2 Level Colonial, Spacious Kitchen, Spacious Bedrooms, Covered Front Porch, Much More!! Just Waiting For Your Personal Cosmetics and Renovations to Make it Shine. Close to Schools, Shopping and Commuter Routes. This Will Not Last! Sol CHESTERTOWN, MD Living Area: 910 Sqft.	2 Beds, 1 Bath	$62,400
234 N COLLEGE AVENUE 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 heart of historic Chestertown. This short sale opportunity is a rare find for savvy investors or buyers ready to bring their visio CHESTERTOWN, MD Living Area: 1296 Sqft.	2 Beds, 1 Bath	$164,000
201 BIRCH RUN ROAD This Mid Century Modern is located in Mile Tree Village, one of Chestertown's most coveted neighborhoods. One floor living makes things a breeze with this open and easy floor plan. Serious structural updates have been performed on the home, the crawl space has been encapsulated, and the kitchen and CHESTERTOWN, MD Living Area: 1588 Sqft.	3 Beds, 2 Baths	$470,000
624 HIGH STREET Step into the charm of historic Chestertown with this 2BR/1BA home full of potential. Featuring a screened front porch, spacious layout, and rear alley access, this property is perfect for investors or visionary buyers. Located just blocks from Washington College, the Chester River, downtown shop CHESTERTOWN, MD Living Area: 1290 Sqft.	2 Beds, 1 Bath	$240,000