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$335,000
3 Beds ⋅ 2 Baths
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 bathrooms with a spacious eat-in kitchen and generous living room provides ample room for comfortable living. Move-in ready condition. Inside, you'll immediately notice the warmth and character of the stunning hardwood floors that flow throughout the home. The open and airy layout ensures a seamless flow between the living spaces, making it perfect for entertaining or just relaxing at home. The well-equipped laundry area comes complete with both a washer and dryer for added convenience. Take full advantage of the outdoor amenities this property has to offer. Start your mornings with coffee on the cozy screened porch or wind down your evenings on the expansive deck overlooking the fenced yard. There's plenty of space to garden, play, or simply enjoy the outdoors in privacy. The property also includes a garage, providing extra storage space and parking. This home is ideal for those seeking both charm and functionality in a serene setting. Don't miss the opportunity to call 10720 Foreston Rd your new home. Schedule your showing today to experience all that this property has to offer!

10720 Foreston Rd, Chestertown

Listing courtesy of Compass. Contact: (301) 298-1001
$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:

$1,195,000
4 Beds ⋅ 3 Baths
This property has an amazing amount to offer! There are 3 parcels included with a total of just over 5.5 acres. The complex includes a 4 bedroom, 2.5 baths extremely well built home on 2.68+/- acres, a .35 acre lot and a commercially zoned 2.6+/- parcel with several large outbuildings. The house also offers a spacious kitchen with center island and granite counters, a family area, laminate flooring throughout most of the house, a laundry room, screened porch and a partial basement. Heated and cooled with heat pump and propane backup. Hot water is supplied by tankless water heating system. There is a 1 car attached garage and a large open dirt floor shed for additional space close by. In the rear of the property is a 47' x 42' two bay pole building with 1 bay having a 12'+/- door. The commercial parcel has a 4 bay garage with foam insulation, an approximately 100' long x approximately 30' wide insulated workshop with 14' door that includes a full bath and laundry, a half bath, office and is heated and cooled. There is a 40' x 30' pole building in the rear of the commercial side. Last but not least is a .35+/- acre lot that has potential to be built on but would require a water and sewer allocation. This is a rare find and would be perfect for someone who has a small lawn/landscaping business and wants to expand or possibly a small excavating business and wants to live where they work. The possibilities are are there for the entrepreneur who has vision, to utilize everything this property has to offer!!

10672 Worton Rd, Worton

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$399,000
4 Beds ⋅ 2 Baths
Welcoming to 21424 Catholic Ave, located in the heart of Rock Hall! Walking distance to many shops, restaurants, and marinas. Nicely situated on a large in-town parcel, the largest residential lot on Catholic Avenue. This 4-bedroom home was redone from the inside out in 2024. The welcoming living space contains original wood accents, adding much charm to this newly updated home. Spacious open living space with a beautifully renovated kitchen, custom wood cabinets, new LVT, and engineered hardwood flooring throughout. Three bedrooms, with great closet space, share a full bath. At the end of the home, you'll find the primary bedroom, with a spacious primary bath and walk-in closet. The oversized two-car garage has plenty of room for extra storage. One-floor living and a two-car garage are hard features to find in downtown Rock Hall. Outside, the possibilities are endless; there's ample room for outdoor activities or projects. Updates include: -Crawlspace encapsulation and whole house dehumidifier -10 new windows -New 25 year roof -Siding, shutters & new gutters -New flooring, engineered hardwood, LVT and carpet -Completely updated kitchen with custom cabinetry -HVAC heat pump & AC -200 amp breaker panel And more!

21424 Catholic Ave, Rock Hall

Listing courtesy of Gunther-McClary Real Estate. Contact:

$549,000
6 Beds ⋅ 6 Baths
Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation at a great price. This property also provides for a perfect multigenerational household. The garage is another amazing plus with a kitchenette, full bathroom and loft for a private office or area for grandkids to roughhouse. Surround yourself with a great sense of community and bucolic farm landscapes. The rear yard includes a hot tub, amazing hardscaping for family gatherings and a view that opens out to peaceful farm fields. Sit in the sunroom at 12712 Still Pond Road and truly understand the quality of life that comes with country living. This is one not to be missed.

12712 and 12714 Still Pond Rd, Still Pond

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

$549,000
Invest with confidence in this amazing duplex opportunity just minutes from Historic Chestertown and the pristine Betterton Beach. Get your entrepreneurial juices flowing because the income opportunity with this property makes it irresistible. You can live in one side and largely get your mortgage paid for you by renting out the other side. You can rent both and enter an easy cash flow situation at a great price. This property also provides for a perfect multigenerational household. The garage is another amazing plus with a kitchenette, full bathroom and loft for a private office or area for grandkids to roughhouse. Surround yourself with a great sense of community and bucolic farm landscapes. The rear yard includes a hot tub, amazing hardscaping for family gatherings and a view that opens out to peaceful farm fields. Sit in the sunroom at 12712 Still Pond Road and truly understand the quality of life that comes with country living. This is one not to be missed.

12712 and 12714 Still Pond Rd, Still Pond

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

$399,800
4 Beds ⋅ 3 Baths
WOW! What a transformation of this sturdy Four Square Colonial nestled in a peaceful small-town setting. Enjoy the convenience of being within walking distance to parks, schools, the post office, and local markets while still having the space and privacy of an oversized nearly half-acre lot. The exterior features a detached oversized two-car garage with pull-through access to the HUGE backyard — perfect for entertaining, gardening, or future outdoor projects. A brand-new roof has just been installed on both the home and garage, adding even more value and peace of mind. Inside, the home has undergone a complete top-to-bottom renovation while maintaining the charm and solid craftsmanship of a bygone era. The stunning new interior includes an open-concept main level, all-new kitchen and baths, updated flooring, fresh drywall, neutral designer paint throughout, and brand-new appliances. Comfort is covered year-round with newly installed central heating and air conditioning. The fabulous primary suite offers a true retreat with a custom glass-enclosed shower and beautifully updated finishes. Additional highlights include a full dry basement offering excellent storage. This home truly offers the best of both worlds — the beauty and convenience of new construction combined with the timeless quality and character of a classic colonial. Put this one at the top of your list to tour soon!

122 Main St, Galena

Listing courtesy of Village Real Estate Company LLC. Contact:

$829,000
3 Beds ⋅ 4 Baths
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 piece of Chestertown history. Nestled in the heart of the Historic District, this pre-Revolutionary residence has stood witness to generations of change while retaining the charm, craftsmanship, and character that make historic homes so special. History is woven into every corner of the property—from the prominence of past owners down to the foundation, which contains the mast of a ship. The only home downtown with such a generous private front courtyard framed by mature landscaping, vibrant seasonal gardens, brick herringbone paths, and mature trees that create a peaceful retreat just steps from town. Whether enjoying a quiet morning coffee, entertaining guests, or simply admiring the blooms, the outdoor spaces are truly a stand-out feature. Approaching the home, guests are welcomed by a wide red front door, a traditional symbol of hospitality in early America, inviting visitors inside just as it has for centuries. Inside, approximately 2,472 square feet of thoughtfully preserved living space blends historic character with modern comfort. Original wide-plank hardwood floors, period moldings and built-in cabinetry, reflect the home's 18th-century origins, while updated kitchens, baths, and central air/heat provide the conveniences expected today. To the right of the grand foyer, a cozy study lined with built-in bookshelves provides the perfect home office or library and could easily be converted into a first-floor bedroom for those seeking single-level living flexibility. A first floor full bathroom with walk in shower is located conveniently around the corner straight through the foyer. To the left of the foyer and at the forefront of the home, the stunningly preserved parlor, featuring 12x12 wavy glass windows, original panel walls and stunning gas fireplace with pine panel surround, offers an elegant setting for entertaining guests or enjoying quiet evenings at home. Just beyond, the large dining room serves as a memorable gathering space, complete with another fireplace, built-in cabinetry, and a charming pop-out window seat overlooking the side gardens. Just beyond that is a chef's kitchen featuring updated appliances, abundant storage cabinetry, generous island workspace, and a soaring tapered tray ceiling that creates an airy and inviting atmosphere. The kitchen breakfast nook is highlighted by panoramic bay window wall. Off the breakfast nook is a convenient half bath and steps to the side courtyard with pergola and a screened porch. The garage—another rarity in the Historic District—provides valuable storage and convenience. Upstairs, the spacious primary suite blends historic character with thoughtful updates, featuring a practical double closet and an en-suite bath highlighted by distinctive MacKenzie-Childs tile floors and decorative vanity hardware. Two additional generously sized bedrooms and a full bathroom provide comfortable accommodations for guests. Beyond its appeal as a private residence, it has proven itself as one of Chestertown's most successful Airbnb properties, generating approximately $32,000 in bookings last year. Whether you're seeking a full-time residence, weekend retreat, or income-producing investment, this property offers exceptional flexibility. Furniture is negotiable for a truly turnkey opportunity. Step outside and enjoy everything that makes Chestertown so beloved. Stroll to art galleries, locally owned shops, restaurants, the farmers market, and waterfront parks along the Chester River. Enjoy annual traditions such as the Tea Party Festival, Downrigging Weekend, and Dickens of a Christmas, all just moments from your front door. Become the steward of a treasured landmark while enjoying the comfort, beauty, and lifestyle that have made it one of Chestertown's most admired homes for generations.

106 Queen St S, Chestertown

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

$389,000
4 Beds ⋅ 2 Baths
Welcome to Crosby Woods, a charming new community located less than a mile from downtown Rock Hall. This thoughtfully designed neighborhood features just ten single-family homes situated on a quiet cul-de-sac with shared open space and no HOA. This brand-new 2,162 sq. ft. rancher offers comfortable one-level living with four bedrooms and two full bathrooms. The home features beautifully finished tile bathrooms with comfort-height vanities and quartz countertops, combining style with everyday functionality. A one-car garage provides convenient parking or additional storage. Enjoy outdoor living with a covered front deck and a partially covered rear deck—perfect for relaxing or entertaining. Experience the ease of community living on a peaceful street while remaining just minutes from the shops, restaurants, marinas, and waterfront activities of Rock Hall.

21733 Centennial Ln, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$1,975,000
5 Beds ⋅ 3 Baths
Experience riverfront living on the Sassafras River with this exceptional home on just over 13 acres. There’s room for everyone with 5/6 bedrooms, 3 full baths, and two kitchens. Enjoy sunrise over the river through the primary bedroom’s expansive window, then watch the eagles and osprey while sipping coffee on the dock. This home boasts a jet ski dock, and both fixed and floating docks with 3 feet mlw. Take the boat to dinner at any of the five riverfront restaurant options, or catch your own dinner on the Chesapeake Bay. There’s plenty of off river activities as well, with 20x40 in-ground saltwater pool, pickleball court, spacious yard, outdoor shower, firepit, and woods. In summer, the 5 acre wildflower field bursts into color, inviting quail, butterflies and songbirds of every sort. With very easy access to points north and south, you can easily spend a day in Annapolis or zip less than 60 miles to the Philadelphia airport. The booming community of Middletown is 15 minutes away, with unlimited restaurant and shopping options. This stunning residence provides an ideal retreat for nature lovers and outdoor enthusiasts alike. Store all your toys in the attached garage and the large outbuilding. Imagine unwinding on your private dock as you enjoy friends and family playing/boating on the river. Launch your kayak or standup paddleboard directly from the property's floating dock. Relax and cool off in the pool after a great day on the river or an invigorating pickleball game. Inside, spacious living areas feature expansive windows that take full advantage of breathtaking water views, creating a light-filled and welcoming atmosphere throughout the home. Every detail has been designed for comfort, convenience, and fun, making this riverfront oasis a truly special place to call home.

14183 Roberts Dr, Golts

Listing courtesy of Gunther-McClary Real Estate. Contact:

$469,000
2 Beds ⋅ 2 Baths
Back on the market. Spectacular Chesapeake Bay waterview condo located in the heart of Rock Hall. Beautiful upgrades include LVP flooring, tile bathrooms, kitchen cabinets, backsplash, granite countertops and appliances, plus new electric fireplace. Relax on the recently refinished Bayview deck or cuddle up next to the fireplace. The convenience of condo living lets you enjoy all the festivals and fun Rock Hall has to offer without the maintenance headaches. This unit has been used as a high quality short term rental for more than a year.

21090 W Sharp St Unit #112, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$1,800,000
4 Beds ⋅ 4 Baths
**Price increase due to the home’s expanded footprint—over 1,200 additional square feet!** **To be built! Welcome to this beautifully designed 3,540 sq. ft. home in Chester River Landing, offering modern comfort, timeless style, and flexible living options. The standard floor plan includes 4 bedrooms and 3.5 baths, with the option to expand to 5 bedrooms and 4.5 baths by adding a first-floor guest suite. Inside, an open-concept main level connects the great room, gourmet kitchen, and dining area—perfect for entertaining. Upstairs, the primary suite features a spa-like bath and walk-in closet, complemented by a convenient second-floor laundry. Designed with future needs in mind, this home also offers the option of a residential elevator for effortless access across all levels. Enjoy broad water views and breathtaking sunrises over the Chester River. The covered porches and expansive windows create a seamless connection to the outdoors, enhancing the waterfront lifestyle of this sought-after community. Deep water boat slips are available for lease or purchase. The community amenities include two docks, pool, grilling and outdoor dining area right on the water, large firepit, area to launch kayaks, canoes and paddle boards, beautifully landscaped paths along the water's edge and much more! Nestled in the sought-after Chester River Landing community, this home combines the charm of the Eastern Shore with the convenience of nearby marinas, shopping, and dining. Located just outside of downtown Chestertown and very close to the Chester River Yacht & Country Club.

Little Harbor Way Unit #1, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact: