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$225,000
4 Beds ⋅ 2 Baths
Extra-wide fenced lot, and just minutes from Chestertown and Chester Harbor. Introducing this spacious 4-bedroom, 2-bath ranch on an extra-wide fenced lot in Chester Harbor, just minutes from historic Chestertown. Offering comfortable single-level living, the home features a large family room, an expansive kitchen with abundant cabinet and counter space, and a functional floor plan that's move-in ready with the opportunity to add your own cosmetic updates. The generous layout includes four bedrooms, two full baths, and flexible space for guests, a home office, or hobbies. Outside, the oversized iron-fenced yard provides plenty of room for gardening, entertaining, pets, or future expansion. Enjoy your morning coffee or evening unwind on the side porch, while the attached one-car garage adds convenient storage. As part of the Chester Harbor community, you'll enjoy access to the community boat ramp and the Chester River, making it easy to spend your days boating, fishing, kayaking, or simply enjoying the waterfront lifestyle. Ideally located near marinas, parks, waterfront dining, and the charm of downtown Chestertown, this property offers the perfect blend of space, convenience, and recreational opportunities.

533 Round Top Rd, Chestertown

Listing courtesy of EXP Realty, LLC. Contact: 8333357433
$295,000
3 Beds ⋅ 2 Baths
COMING SOON!! Welcome home...spacious rancher nestled on a beautiful, private 1-acre lot. This home offers 3 bedrooms, 2 full bathrooms, a cozy living room, and an eat-in kitchen perfect for everyday living. The full unfinished basement provides endless possibilities for additional living space, a workshop, or extra storage. Step outside to enjoy the peaceful backyard, featuring a privacy-fenced yard and a paved driveway. The roof, siding, and windows were replaced approximately 10 years ago, offering added value and peace of mind. Stay warm and keep utility costs down during the colder months with both a pellet stove in the living room and a wood-burning stove in the basement. With just a little updating, this home could be everything you've been looking for. Offering privacy, space, and endless potential, it's a great opportunity to make it your own. Located just minutes from the historic waterfront town of Chestertown, you’ll enjoy charming boutiques, local restaurants, seasonal festivals, the popular Farmers Market, and plenty of ways to experience the scenic beauty of the Chester River. The area perfectly captures the charm and lifestyle of Maryland’s Beautiful Eastern Shore.

240 Round Top Rd, Chestertown

Listing courtesy of Clark & Co Realty, LLC. Contact: 410-490-2183
$315,000
3 Beds ⋅ 2 Baths
Welcome to 109 Parma Road in family-friendly Chester Harbor. This well-maintained home is located on a quiet street and has three generously sized bedrooms with hardwood flooring and 2 full bathrooms. An upgraded kitchen featuries granite countertops, SS appliances, and solid wood cabinets with quiet-close drawers. Spacious living room off the kitchen and dining room combo. Spacious and private backyard is perfect for dogs and children. Mature oak trees provide lots of cool shade. Recent upgrades include: bathroom vanities, ceilings fans, light fixtures, microwave, interior paint, driveway crushed run. Chester Harbor is a quiet community with water access to the Chester River for just $15 per year and NO HOA. 5 minutes to downtown Historic Chestertown. Founded in 1706, Chestertown sits on the banks of the Chester 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. Enjoy country living on the Eastern Shore. Less than one hour to Annapolis. Much more info and professional photos coming soon. Stay tuned!

109 Parma Rd, Chestertown

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

$205,000
3 Beds ⋅ 1 Baths
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 new owners. Highest and Best by 5PM 8/12/26

202 Pine St, Chestertown

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

$380,000
3 Beds ⋅ 2 Baths
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 pond, offering a peaceful setting with endless possibilities for outdoor enjoyment. A spacious 40' x 60' outbuilding equipped with three-phase electric provides exceptional flexibility for a workshop, home-based business, storage, agricultural use, or hobby space. A recently installed new roof helps reduce renovation costs and provides a great head start on your restoration project. Whether you're looking to renovate the existing home, create a private country retreat, or capitalize on the property's versatile amenities, this is a rare opportunity with tremendous potential. Property is being sold as-is

8312 Broad Neck Rd, Chestertown

Listing courtesy of Pearson Smith Realty, LLC. Contact: 5713861075
$344,000
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. 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:

$468,000
3 Beds ⋅ 2 Baths
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, and a convenient circular driveway. The drive runs under a gable-roofed breezeway that connects to an oversized 26x40 two-car garage, which will soon have brand-new garage doors. Coming into the Home... Living Room: Walk along the cobblestone slate path and pass through the new, classic front door into a spacious living room featuring hardwood floors that run throughout the entire house. Dining & Kitchen: A curved archway leads from the living room directly into the dining room. The dining room has an entryway to the kitchen, which could easily be opened up for an even more open feel. Porch: The dining room leads right out to a comfortable porch—the perfect spot to relax and enjoy this nice, quiet neighborhood. Mudroom & Back Entry: An oversized back entry from the breezeway leads into a large mudroom and utility space. Featuring multiple closets and laundry hookups, this functional area offers plenty of space to be creative and fit your family's needs. Bedrooms: The main floor includes three bedrooms with hardwood floors and two full bathrooms Basement: The full basement features an open space with brand-new windows that allow plenty of natural light inside. It is equipped with a new sump pump, offering a perfect blank canvas for storage, a gym, or a rec room. Utilities, Key Updates & Location The house sits on a generous lot with mature landscaping and is connected to well water and public septic. Recent mechanical and structural updates include: Brand-new roof, oil furnace paired with a new HVAC system for efficient heating and cooling. Fresh paint inside and out. You can enjoy beautiful views of the Chester River coming and going from your new home, as well as scenic river views while taking your neighborhood walks. Enjoy the convenience of being just minutes from downtown shopping and dining. Bring your design ideas to update the interior and make it your own!

25750 Collins Ave, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$380,000
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:

$320,000
3 Beds ⋅ 2 Baths
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:

$365,000
3 Beds ⋅ 2 Baths
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 community—offering the best of Eastern Shore living! Located in the Queen Anne’s County school district and just minutes from downtown Chestertown, you’ll love the convenience paired with the peaceful setting. Enjoy easy access to the Chester River—you can drive your boat to the community ramp at the end of the street, or even take a nice short walk down to the water, to spend your days crabbing, fishing, kayaking, or simply soaking in the waterfront lifestyle. Inside, this 3-bedroom, 2 full bath home features durable and stylish LVP flooring throughout and a thoughtfully designed split floor plan. The spacious primary suite is privately situated on one side of the home and offers a walk-in shower, dual vanity, and a beautifully appointed bath. On the opposite side, you’ll find two additional bedrooms and a full bath with a tub/shower combo—ideal for guests or flexible living. The kitchen and living room are centrally located, creating an inviting and functional space for everyday living and entertaining. A standout bonus—an unfinished upstairs area of 544 additional SF, already in place and ready for your vision! Use it for storage now or finish it off for additional bedrooms, a home office, or recreation space. Step outside and enjoy both a charming front porch—perfect for morning coffee—and a massive back deck ideal for entertaining, grilling, or simply relaxing while taking in the peaceful surroundings. The generously sized yard with mature trees offers both privacy and room to enjoy the outdoors. Even more exciting—the county has indicated plans to pave the road in the near future. Added perk: fiber optic Talkie Internet is already available at the property, making working from home or streaming a breeze. Move-in ready, full of potential, and located in a charming waterfront community—this one checks all the boxes!

240 Merganser Dr, Chestertown

Listing courtesy of Chesapeake Real Estate Associates, 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: