Refine Search
Map
Sort by
$229,000
3 Beds ⋅ 1 Baths
This 3-bedroom, 1-bathroom ranch-style home in Quaker Estates offers a solid investment opportunity with a total finished area of 936 sq ft. Built in 1963, the property features essential appliances including a refrigerator and stove, ensuring immediate functionality for tenants or future buyers. The average condition of the home allows for potential value-add renovations, which can significantly increase rental income or resale value. The spacious 0.34-acre lot provides ample outdoor space, while off-street and driveway parking enhances convenience for residents. A shed on the property offers additional storage options, appealing to renters seeking practicality. With no pool maintenance costs and a straightforward layout, this property is low-maintenance, making it an attractive option for investors looking to maximize returns. The combination of location, features, and potential for appreciation makes this property a compelling addition to any real estate portfolio.

7415 Wilkins Ln, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$275,000
3 Beds ⋅ 1 Baths
Welcome home! This beautifully maintained and updated property sits on a generous .45-acre lot in a lovely, quiet neighborhood, with a peaceful, wooded backdrop for added privacy. Renovated in 2017, this home offers numerous upgrades and thoughtful improvements, including hardwood floors, newer windows and doors, updated HVAC, and a newer roof. The kitchen features 42-inch cabinetry, granite countertops, and stainless steel appliances, while the custom ceramic-tile bath adds an extra touch of style. Enjoy the best of outdoor living from the fabulous screened-in porch and deck, perfect for relaxing, entertaining, or simply enjoying the tranquil surroundings. A large parking area provides plenty of space for family and guests, and the partial basement offers additional storage or flexible-use space. With so many major updates already completed, there is little left to do but move in, relax, and enjoy! A wonderful opportunity for anyone looking for a move-in-ready home with space, privacy, and a great neighborhood setting. Location is a bonus! Just minutes from historic downtown Chestertown, offering convenient access to local shopping, restaurants, movies, and a variety of waterfront activities. Enjoy the peaceful feel of a quiet neighborhood while being close to everything Chestertown has to offer. Schedule your tour today!

7482 Poplar Ave, Chestertown

Listing courtesy of Taylor Properties. Contact:

$315,000
3 Beds ⋅ 1 Baths
Here is 24775 Langford Road, a well-maintained 3-bedroom, 1-bath home situated on 1.27 acres in a peaceful country setting just minutes from downtown Chestertown. The property features a spacious two to three-car detached garage/workshop, offering plenty of room for vehicles, storage, hobbies, or projects. A large Trex deck provides additional outdoor living and entertaining space. The home underwent extensive renovations in 2018, including the roof, windows, siding, gutters, storm doors, HVAC system, the Well was done in 2021, and partial crawl space encapsulation. Interior improvements included refinishing of the original hardwood floors and a remodeled kitchen featuring all-wood cherry cabinetry and stainless-steel appliances. With numerous major improvements already completed, garage and workshop space, and over an acre of property, this home offers comfortable country living with convenient access to Chestertown, Rock Hall and surrounding areas.

24775 Langford Rd, Chestertown

Listing courtesy of RE/MAX Chesapeake. Contact:

$300,000
3 Beds ⋅ 1 Baths
**OPEN HOUSE Sunday September 13th 11AM-1PM** This adorable rancher will soon be at the top of your "favorites" list, with a welcoming interior and plenty to love outside. Set on a spacious corner lot, you'll find a long driveway, new paver patio, vinyl privacy fencing, playset and room to roam, while the inside features a beautiful kitchen, spacious living room and updated bathroom. Cute, low maintenance and just the right size to come make your own!!

104 Lincoln Dr, Chestertown

Listing courtesy of RE/MAX Executive. Contact: 4432741900
$1,195,000
2 Beds ⋅ 1 Baths
Remarkable downtown Chestertown development opportunity outside the Historic District. Incredible potential for a builder or a unique property for a private homesite. Directly adjacent to the Chestertown walking rail trail and just steps from downtown Chestertown while overlooking the Lawrence Wetland Preserve, rolling meadows and Radcliffe Creek behind. Sale includes two parcels - 302 S Mill (.45 acres) and 300 S Mill (.55 acres) - totaling approximately 1 acre. 300 is unimproved and 302 has a 1960s brick home on it. R:6 Traditional Neighborhood Development Zoning permits a wide range of dense residential development opportunities. Maximum residential density is limited to 42 bedrooms which could be single family homes, multi-family, apartments, townhouses, rowhouses, condos, and others. Smaller commercial options available as well. Public water and sewer is on site and additional allocations are available. Entire site is usable. Property is partially wooded with several large mature Oak Trees. Founded in 1706, Chestertown sits on the banks of the Chester River and is home to Washington College. Enjoy the historic homes, local shopping, restaurants, art galleries, and waterfront parks. Chestertown is home to many festivals, an award-winning weekly Farmer's Market. Additional information available upon request. Buyer to perform own due diligence. Do not enter property without and appointment.

302 S Mill St, Chestertown

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

$345,000
3 Beds ⋅ 2 Baths
Lovingly restored rancher located on a a quiet street in sought after Chester Harbor. Generous sized corner lot, with beautiful landscaping and asphalt drive. Home had a complete renovation in 2020 inside and out and practically everything is new since then. Enter into an inviting and updated open floor plan that combines living and dining area, perfect for entertaining and large gatherings. Updated laminate plank floors throughout entire home with SS appliances and kitchen breakfast bar, plus separate dining area. Stackable laundry and half bath conveniently located just off dining area. The sun room, over looking the back garden makes a great sitting room, office, or flex space. Down the hall you'll find 3 good sized bedrooms, all with double closets, a good sized bathroom with modern vanity, laminate floors and tub shower. Outside is a gardener's oasis with mature specimen plantings, just waiting for you to make it your own!

217 Edmore Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$304,000
3 Beds ⋅ 2 Baths
Affordable, adorable, and move-in ready! This charming home offers everything you need with a great open floor plan designed for comfortable living. The private primary suite features its own bathroom and is thoughtfully separated from the two additional bedrooms for added privacy. The laundry room is conveniently located just off the kitchen and includes a separate exterior entrance. Step outside and enjoy the fully fenced backyard, complete with a storage shed, cozy patio area, and fire pit area, making it perfect for relaxing or entertaining. Dont wait to see this one!

7464 Shortall St, Chestertown

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

$455,000
2 Beds ⋅ 2 Baths
Welcome home to 7982 Radcliffe Road! This charming corner-lot offers a perfect blend of character and modern comfort. Built in 1978- this well maintained 2 bedroom, 2 bathroom home feels more of a newer era. Inside you'll find a spacious living room with plenty of room to relax by the fireplace or entertain! The oversized garage offers amazing storage and features an office space that is closed off. Outside, you can enjoy the nice-sized yard with the views of a crop field and beautiful sunsets. Located right outside of Chestertown, the home puts shops, restaurants, and the local farmers market close by and is also walking distance to a view of the Chester River! An amazing opportunity to enjoy small-town living convenience, space & character!

7982 Radcliffe Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$299,900
3 Beds ⋅ 1 Baths
MOVE IN READY!! Charming 3 bedroom ranch home in the desirable water oriented community of Chester Harbor. This recently updated home offers a wonderful blend of modern comfort, convenience and peaceful surroundings. The home features a carefully updated galley kitchen with beautiful custom countertops, soft close cabinets and stainless steel appliances. The home also offers a reverse-osmosis water system in the kitchen. Numerous updates have been completed recently, including new LVP flooring, carpet, light fixtures, a new roof in 2020, new windows in 2021, new exterior and entry doors in 2023. Perfect location for dog lovers with a recently added split-rail fence enclosing the backyard. Walking distance to Round Top Park and minutes from Downtown Chestertown where you can enjoy local restaurants, shops, waterfront attractions, the dog park and the popular farmers market every Saturday! Don't miss this opportunity to make this wonderful property your new home!

124 Wilton Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$750,000
3 Beds ⋅ 3 Baths
Welcome to Mile Tree Village, one of Chestertown’s most desirable neighborhoods, where this beautifully maintained 1994 brick rambler sits proudly at the end of a quiet cul-de-sac on more than a half acre lot. Offering 3 bedrooms, 2.5 baths, and over 2,100 square feet of thoughtfully designed main level living, this home combines timeless Eastern Shore appeal in an absolutely turnkey package. * A freshly sealed asphalt drive curves to a welcoming front entry, where a classic brick facade sets a warm, distinctive tone. A two-car attached garage provides direct entry and everyday convenience. * Inside, the open kitchen—complete with breakfast area—flows seamlessly into a spacious family room, perfect for everyday living. A separate dining room makes entertaining easy. The family room is an elegant space for gatherings, while a dedicated sunroom and screened-in porch invite you to enjoy the serene, park-like backyard in every season. The large deck offers an additional outdoor retreat with tranquil wooded views. * The generous primary suite features an en-suite bath, while two additional bedrooms makes for flexible bedroom accommodations for family, guests, or a quiet work-from-home office space. A convenient half bath and main-floor laundry round out the practical layout. A full basement offers abundant storage and endless potential for an artist’s studio, workshop, recreation room, or finished expansion. * With its pristine landscaping, mature plantings, and verdant views, this exceptional home is a rare find. And the location is second to none—just minutes from historic downtown Chestertown. Stroll tree-lined streets to discover specialty shops, art galleries, restaurants, and the Saturday Farmers Market at Fountain Park. Washington College, the nation’s tenth-oldest college, anchors the community with year-round cultural events, lectures, and performances. Outdoor enthusiasts will love the nearby Rail Trail, Sultana Lawrence Wetlands Preserve, marinas, and public boat launches providing easy access to the Chester River and Chesapeake Bay. First Friday celebrations, waterfront festivals, and a vibrant arts scene make Chestertown one of the Eastern Shore’s most beloved places to call home.

216 Birch Run Rd, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$799,000
3 Beds ⋅ 3 Baths
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 a peaceful, park-like setting. Designed for both comfort and elegance, this home features expansive, light-filled interiors and timeless architectural details throughout. The heart of the home is a large, luxurious living room showcasing vaulted, beamed ceilings, a fireplace, and sweeping views of the expansive rear yard. Rich hickory hardwood flooring runs throughout the kitchen, breakfast area, living room, office, and formal dining room, creating a warm and cohesive flow across the main living spaces. The formal dining room is enhanced with elegant crown molding, offering a refined setting ideal for both everyday living and entertaining. The updated gourmet kitchen features granite countertops, abundant cabinetry, and a seamless connection to the breakfast area and main living spaces, making it both functional and inviting. The private primary suite is generously sized and offers two walk-in closets along with a beautifully appointed en-suite bath featuring a luxury soaking tub, double vanity, travertine tile flooring, and a tiled walk-in shower. Two additional bedrooms provide ample closet space and share a well-appointed full bath, also finished with travertine tile flooring and a tiled shower. Outdoor living is equally impressive with extensive mature landscaping that enhances privacy and natural beauty. A stone patio and a combination of brick and Trex decks provide multiple spaces for relaxing or entertaining while enjoying the serene surroundings. Additional features include an attached two-car garage as well as a detached one-car garage, offering exceptional storage and flexibility. Ideally located just minutes from historic Chestertown and only a golf cart ride to the Chester River Yacht and Country Club and the Chester River, this exceptional home blends privacy, convenience, and luxury Eastern Shore living at its finest.

7828 Country Club Ln, Chestertown

Listing courtesy of Cross Street Realtors LLC. Contact: 4434803453
$324,000
3 Beds ⋅ 2 Baths
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, functionality, and privacy with NO HOA! In addition, there's a versatile bonus/flex room that is ideal for a home office, hobby area, or even a potential 4th bedroom to suit your needs - all on the convenience of one-level living. Step inside to discover a bright, inviting interior featuring brand-new luxury vinyl plank flooring and carpet, fresh paint throughout, and a thoughtfully updated kitchen complete with new butcher block countertops, brand-new stainless-steel appliances, and ample cabinet space. A new HVAC system, brand-new roof, and a ONE-YEAR HOME WARRANTY provide peace of mind, allowing you to move in and enjoy your new home from day one. Outside, the expansive 1.66-acre lot offers endless opportunities for gardening, entertaining, recreation, or simply enjoying the tranquility of nature. A storage shed provides additional space for tools, lawn equipment, or outdoor hobbies. Whether you're a first-time homebuyer, someone looking for convenient one-level living, or looking for a move-in-ready home with room to spread out, this property checks all the boxes! Conveniently located just minutes from historic downtown Chestertown, Rock Hall, nearby marinas, dining, shopping, and waterfront activities - with convenient access to major routes into Delaware and Pennsylvania - this property offers the ideal balance of peaceful rural living and easy travel. This is a rare combination of acreage, versatility, and affordability. In addition, this property has public water and sewer. The property is priced below the appraised value, giving the new owner built-in value from day one! Schedule your tour today and see why this home works just as well for everyday living as it does for your Eastern Shore escape!

9126 Fairlee Rd, Chestertown

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

$372,000
4 Beds ⋅ 2 Baths
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. Easy one-level living with an open concept for the Living Room, Dining, and Kitchen. A really open feel. This home offers 4 bedrooms and 2 full bathrooms. If this many bedrooms are not needed, the fourth bedroom could have many other potential uses, with it being right off the kitchen and living room. Out front, you have a cozy front porch, and out from the sliding glass door it opens up to a deck and a good-size backyard. Just pick where you would like to sit for a few and relax. In the back of the yard, you have a new storage shed that is always a plus. Bring your bikes; you will have the perfect streets in this neighborhood to ride and use as you head to the Local Farmers Market. The pictures show this house perfectly. It is in such good condition and has been well cared for and maintained. All ready to move into. It won't disappoint.

213 Byford Dr, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$275,000
3 Beds ⋅ 1 Baths
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 space that opens into the dining area. This space is nice and open, as you can easily see into the living room. Still plenty of space for a table. The washer and dryer are located in the oversized storage closet with bi-fold doors in the kitchen. Has an additional coat closet as you come in the side door and a separate pantry. Nice open back yard. A solid house in proximity to town. Good place to make your own and call home, or an investment.

956 Washington Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$315,000
3 Beds ⋅ 2 Baths
* SELLER IS OFFERING A 1 YEAR HOME WARRANTY WITH ACCEPTABLE OFFER * 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 water heater, and a recently replaced roof system in March 2026. The property is served by public sewer for added ease and reliability. Step outside to a large rear deck, perfect for entertaining or relaxing while enjoying the peaceful surroundings. The home also offers plenty of storage space in the attic, providing added convenience and functionality. Residents enjoy access to a private community beach and boat ramp. Also conveniently located within walking distance to Tolchester Marina and Shanty Beach Bar, offering outdoor entertainment throughout the summer months. Approximately 10 minutes to Rock Hall and 20 minutes to Chestertown, this home offers the perfect blend of comfort and rural living. Enjoy all that Tolchester has to offer at 8706 Elm.

8706 Elm Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$320,000
3 Beds ⋅ 2 Baths
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. 3 bedrooms and 1.5 bathrooms, open living and dining space, large sunroom/ porch with wood-burning stove, and an additional wood stove in the living room. Outside there's a small storage shed and a larger workshop/shed next to the asphalt driveway. The sunroom leads to a deck overlooking the large yard. Great community with water access. Quick ten minutes into Chestertown, and less than an hour to Middletown DE or Annapolis.

222 Dutchess Rd, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact: