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$280,000
3 Beds ⋅ 1 Baths
Discover this beautiful 3-bedroom Cape Cod home in the heart of Worton, Maryland, conveniently located near local amenities and scenic Eastern Shore attractions. Thoughtfully updated with over $20,000 in upgrades, this residence effortlessly blends classic charm with modern comfort. The inviting living spaces feature abundant natural light and elegant finishes throughout. The upgraded kitchen is perfect for both cooking and entertaining, while the spacious bedrooms offer comfort and tranquility. Step outside to a lovely yard with a recently installed privacy fence, ideal for family, pets, evening gatherings, or enjoying your morning coffee. This home offers the perfect combination of charm, comfort, and value. Don’t miss the opportunity to make this beautifully upgraded Cape Cod your new home.

11060 Plum Dr, Worton

Listing courtesy of Patterson-Schwartz Real Estate. Contact: 4108851606
$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:

$585,000
This 10,000 SF commercial building presents a prime investment opportunity with significant investment potential. Located on an irregularly shaped parcel, the property offers flexibility for various development options, making it ideal for investors looking to capitalize on future growth. Built in 1955, the structure requires major rehabilitation, allowing for customization to meet market demands. The building features durable brick and aluminum facia on block construction. Concrete and hardwood flooring provide a solid foundation for redevelopment. Ample paved parking enhances accessibility, attracting potential tenants or customers. With no current association fees or amenities, investors can maximize their profit. The expansive size and strategic location position this property for various commercial uses, from retail to mixed-use developments. Seize the opportunity to transform this property into a lucrative asset in a growing market. A buyer is responsible to confirm all details and uses of the property.

21309 E Sharp St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$515,000
4 Beds ⋅ 2 Baths
Amazing waterfront community on the Sassafras river. This Kentmore Park cottage was originally built in 1953. Major renovation in 2006 adding bedrooms, bathroom, basement, large light filled gathering room. The rear deck has space for outdoor dining and privacy. The perfect get away or primary residence. Well maintained. Four bedrooms and two baths. One bath reconfigured with stack washer and dryer. Could be returned to full bath when relocating washer and dryer to basement. Lovely pastoral view of farmland. Easy path to beach and central Kentmore Park area. Tax free shopping in Delaware. Convenient shopping in Galena. Check out Cross Street Market for produce, local meat, specialty foods, plantings and friendly faces. Explore Jones Farm for local meats and ice cream. Event space for special occasions, pumpkin patch and seasonal surprises. Convenient Sassy Market for deli, fresh meat and the perfect snacks and beverages. Galena has fine and casual dining, pizza and delicious steak sandwiches. You are close to Historic Chestertown with casual and special dining, eclectic shopping, Chestertown Golf and Country Club, waterfront access, fishing and boating opportunities. Cruise the Chester River on the Packet for an adventure or special celebration. Visit historical buildings. Enjoy weekend activities in History Park in the center of town, farmers market, Tea Party, Crazy Days sales and more. Never a dull moment. Chestertown is full of history including Washington College and the Chestertown Tea Party Reenactment. This home offers so much not to mention lazy days on the beach, water sports, friendly and welcoming neighbors, gathering at the pier for taps and the sunset. Living the Life! Kentmore Park was established in the late 1940 era. Started mainly as a sailing community for weekend and summer enjoyment. Now a very active community with year round social events as many familys have expanded their time in Kentmore beyond spring, summer and fall. A mix of full time and part time residents. All ages are represented. There is a social club with $350.00 yearly dues. There are many activities with the Kentmore Park Improvement Association (KPIA) for all ages. Easy travel to points north and south. PA, NJ, DC. Easy day trip to Annapolis, Easton, St. Michaels.

14136 Kentmore Park Rd, Kennedyville

Listing courtesy of Gunther-McClary Real Estate. Contact:

$288,500
3 Beds ⋅ 1 Baths
Welcome to easy Eastern Shore living in this beautifully updated 3-bedroom, 1-bath home that truly feels like new. Recently updated with a new roof, water heater, HVAC system, stainless steel appliances, luxury vinyl plank flooring, carpet, fresh paint, recessed lighting, and a vapor barrier and insulation in the crawlspace. This home brings modern comfort and a bright, inviting feel to every space. Perfectly positioned to enjoy the best of summer on the Shore, you’re just a short drive (approximately 12 minutes) from the charm of historic Chestertown, the sandy shoreline at Betterton Beach, or waterfront dining and boating at Great Oak Landing. Whether your weekends are spent on the water, exploring local shops, or relaxing by the bay, this location puts it all within easy reach. If you’ve been searching for a low-maintenance home with modern updates and unbeatable access to the Shore’s favorite destinations, this one checks all the boxes.

11167 Oak Ln, Worton

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

$325,000
Discover a unique opportunity in the heart of the Town of Rock Hall with this commercial property, built in 1960 and situated on a 0.189-acre lot. This versatile space, constructed with durable block and featuring concrete flooring, offers a solid foundation for a variety of commercial or retail uses. The Town of Rock Hall is renowned for its vibrant community spirit, with local shops, restaurants, and waterfront attractions just a stone's throw away. Residents and visitors enjoy access to Main Street events and activities, with abundant recreational opportunities for outdoor enthusiasts. The property is walkable to public parking areas and is served by the free "Rock Hall Rides" Shuttle. This property presents an exceptional chance to invest in a thriving community, where business potential meets local charm.

21279 W Sharp St, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$425,000
2 Beds ⋅ 2 Baths
This unique mixed-use property offers exceptional flexibility and opportunity just outside the town of Rock Hall. The first floor features a versatile storefront currently operating as a bookstore, with a history of successful uses including a fabric studio, pottery studio, marine engine shop, and appliance store—showcasing its adaptability for a wide range of business ventures. The second-floor residential space provides comfortable living with an eat-in kitchen, formal living room, family room, one full bath, and two bedrooms. A spacious rear deck extends the living area outdoors, perfect for relaxing or entertaining. Additional improvements include a 35’ x 28’ pole barn and a 28’ x 14’ shed currently utilized as a bookstore event space, adding even more functional possibilities. The property also features a beautiful garden area ideal for outdoor gatherings and enjoyment. With its prime location just outside Rock Hall, this property blends commercial opportunity with residential comfort in a highly desirable setting.

6202 Rock Hall Rd, Rock Hall

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

$898,000
3 Beds ⋅ 4 Baths
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 induction range, ample cabinet space, and a large island for entertaining. The home is filled with natural light and boasts multiple balconies and a front porch for relaxing. You'll love the warm hardwood floors throughout the home. On the second level you'll find two bedrooms and two bathrooms. The third bedroom encompasses the entire third floor and has a great view of the Chester River. You'll enjoy the large back balcony with views of historic Chestertown. The third level could be used as the primary bedroom; there is a large full bathroom and closet. The townhomes have a private driveway, so you'll never worry about finding a parking space. Take advantage of the easy access to Wilmer Park and Chestertown Marina, located just across the street. This townhouse is located in the heart of all Chestertown has to offer! Just a short distance to shops, restaurants, renowned bakeries, and the year-round farmers market by Fountain Park. You will have a front-row seat to the Downrigging Festival! Not to mention the many festivals held in downtown Chestertown throughout the year.

226 S Water St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$329,000
4 Beds ⋅ 2 Baths
Welcome to this beautifully renovated 4-bedroom, 2-bath Cape Cod located in the heart of Rock Hall, MD! Completely updated from top to bottom, this home features a brand-new roof, HVAC system, water heater, flooring, paint, upgraded bathrooms, interior doors, and stylish recessed lighting as well as ceiling fans throughout. Enjoy mornings and evenings on the charming screened-in front porch, perfect for relaxing or entertaining. Inside, the home offers a bright and open layout with modern finishes while still retaining that classic Cape Cod charm. Sitting on a large lot, there’s plenty of space for outdoor activities, gardening, boat storage or future expansion. The is ample parking in the driveway as well as two-way access. Ideally situated in the sought-after waterfront town of Rock Hall, you’ll be just minutes from multiple boat ramps, marinas, and a short walk to restaurants, local shops, and the center of town. Whether you're looking for a full-time residence or a weekend getaway, this turn-key home delivers the best of Eastern Shore living. Move-in ready and loaded with upgrades—don’t miss this opportunity!

21305 Haven Rd, Rock Hall

Listing courtesy of RE/MAX Point Realty. Contact: (302) 426-2211
$1,300,000
Mixed-use commercial property in charming historic Chestertown. 327 Cannon was newly constructed in 2006, yet is perfectly situated in bustling historic district. Offering historic charm without the extra maintenance. The building contains two large units with many possibilities. The first level is outfitted with a commercial kitchen and large dining space overlooking Cannon St. Over 1300 sq ft of professional kitchen space, an office, and dining area. The space has many possibilities for a restaurant or other commercial business in the future. Currently, this unit is leased to Occasions Catering. The upstairs apartment is inviting and spacious, offering two bedrooms each with an ensuite full bathroom. The living space is open and airy, with ample natural light, vaulted ceilings, hardwood floors and a gas fireplace. The large loft could be an office, den, or creative studio space. The walk-in attic provides additional storage. An ideal investment in historic Chestertown.

327 Cannon St, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact:

$550,000
5 Beds ⋅ 4 Baths
103 Sutton is perfectly situated just a stone’s throw from the vibrant heart of Downtown Chestertown. This exquisite 4+ bedroom residence is designed to cater to the diverse needs of today’s Buyers, offering a harmonious blend of comfort, style, and functionality. This home is ideal for those upsizing or seeking multi-generational living. * Originally built as the community model home – and meticulously maintained since – it has ALL the extras: generous breakfast nook bump out, gas fireplace, gleaming hardwood floors, upgraded carpet, oversized windows, granite countertops, stainless appliances, dedicated home office, and a finished basement with a full bath and expansive wet bar. * As you step inside, you’ll be greeted by a two-story foyer flooded with light, dining room and den or family room. The gourmet kitchen that is a chef’s paradise, featuring high-end appliances, custom hardwood cabinetry, and a small island for an ideal triangle of space for meal prep. The open concept layout flows effortlessly into the breakfast nook and living room, providing the perfect setting for family gatherings and celebrations with friends. Click on the propane fireplace for a cozy night watching the sunset or snow flurries outside the tall windows. * The spacious primary suite is an escape through a double door entry – featuring a lighted tray ceiling, a large walk-in closet, en suite bath with soaking tub, glass shower, and a separate water closet. Three additional bedrooms all have custom trim work, generous closets, and large windows. * The finished basement is a standout feature, complete with a stylish wet bar with stone walls that transforms it into the ultimate entertainment zone, perfect for hosting game nights or movie marathons. The backyard feels private with mature trees and a gentle slope, ideal for play space. * The proximity to local parks, playgrounds, restaurants, and shopping ensures that all your family’s needs are met within minutes. Additionally, the Coventry Farms neighborhood fosters a sense of community all while being a convenient distance from Middletown, DE, Philadelphia, PA, Washington DC, Baltimore, MD, and points beyond. * This home is not just a place to live; it’s a lifestyle waiting to be embraced. Don’t miss the opportunity to make this stunning property your own. Schedule your private tour today and experience firsthand what this exceptional home has to offer.

103 Sutton Way, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$540,000
3 Beds ⋅ 3 Baths
Deck was washed and stained on 5/20/26! Built in 2018, this custom coastal raised home is ideally located just one block from the Chesapeake Bay, offering the perfect blend of relaxation, recreation, and investment potential. Enjoy easy access to Rock Hall’s 12 marinas, Ferry Park Beach, local restaurants, shops, and charming downtown—all just a short walk, bike ride, or drive away. Nature lovers will appreciate the close proximity to Eastern Neck Island National Wildlife Refuge, where you can explore by foot, kayak, or bike. Designed for both everyday living and entertaining, the home features an oversized two-car garage with abundant parking—ideal for storing kayaks, paddleboards, bikes, jet skis, and more. The spacious, private backyard sets the stage for gatherings with a fire pit and over 1,000 square feet of wraparound decking invites you to take the party upstairs. A covered porch offers the perfect spot to relax and enjoy summer storms or gentle coastal breezes, and the outdoor shower makes rinsing off after a day on the Bay a breeze. Inside, you’ll find beautiful hardwood floors throughout, generously sized bedrooms, and a thoughtfully designed layout. The primary suite includes dual closets—one being an oversized walk-in—a full en-suite bath with tub/shower combo, and private deck access complete with a TRX workout area. The main living level showcases a bright, open-concept floor plan with stunning 360-degree views, ideal for entertaining. The top level features stainless steel appliances, granite countertops, and walls of windows that flood the space with natural light and capture glimpses of the Bay. Multiple sliding glass doors on every level seamlessly connect indoor and outdoor living, making the expansive decks a true extension of the home. Furnishing will be offered to be purchased making this turnkey, this property also boasts a proven rental history with three years of returning Airbnb and VRBO guests—providing excellent income potential for the weeks you’re not enjoying it yourself. Annual income details available upon request. Don’t miss this exceptional opportunity to own your slice of the Bay lifestyle!

21186 Chesapeake Ave, Rock Hall

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

$105,000
2 Beds ⋅ 2 Baths
Brand new 2025 Clayton Ruby Z located in the Circle Park mobile home community in Rock Hall. This 2-bedroom, 2-bathroom home features a spacious open floor plan with a full bedroom and bathroom on either end, offering privacy and flexibility. The home comes complete with brand-new appliances and is ready for its first owners. Public water and sewer. Financing available through Clayton Homes, subject to credit score and financing approval. Offered at $110,000. Buyer must be approved by the park. Ground rent is $550/month (buyer to verify). Contact us to schedule a tour.

5656 Circle Park Dr Park Unit ##5594, Rock Hall

Listing courtesy of Rock Hall Properties Real Estate. Contact:

$3,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:50 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the major traffic artery, Fairlee Rd, connecting to the surrounding areas.

Cogar Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124
$225,000
This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.87± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, subject to town planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to confirm specific zoning regulations, permitted uses, public water and sewer hook-up fees and taxes to ensure the property suits their intended plans. Whether you are looking to expand your business or invest in a growing area, this lot offers an excellent foundation for future success. Do not miss this rare opportunity.

Haacke Drive Lot 3, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$250,000
This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, subject to town planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to confirm specific zoning regulations, permitted uses, public water and sewer hook-up fees and taxes to ensure the property suits their intended plans. Whether you are looking to expand your business or invest in a growing area, this lot offers an excellent foundation for future success. Do not miss this rare opportunity.

Scheeler Road Lot 2, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$225,000
This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Haacke Drive, this 0.87± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, subject to town planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to confirm specific zoning regulations, permitted uses, public water and sewer hook-up fees and taxes to ensure the property suits their intended plans. Whether you are looking to expand your business or invest in a growing area, this lot offers an excellent foundation for future success. Do not miss this rare opportunity.

Haacke Drive Lot 3, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$250,000
This prime commercial lot presents an exceptional opportunity for your next business venture. Situated on Scheeler Road, this 0.85± acre parcel is zoned C-1, allowing for a wide range of commercial uses. With limited commercial land available in both the town and county, this is a rare offering in a desirable location with strong potential for visibility and customer traffic. There is also potential for R-4 (Residential) zoning, subject to town planning and zoning approval. Ideal for retail, office space, or service-oriented businesses, the property is ready for development. Buyers are encouraged to confirm specific zoning regulations, permitted uses, public water and sewer hook-up fees and taxes to ensure the property suits their intended plans. Whether you are looking to expand your business or invest in a growing area, this lot offers an excellent foundation for future success. Do not miss this rare opportunity.

Scheeler Road Lot 2, Chestertown

Listing courtesy of Select Land & Homes, LLC. Contact: (410) 708-0956
$3,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 1:00 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the major traffic artery, Fairlee Rd, connecting to the surrounding areas.

Tonopah Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124
$3,000
ONLINE AUCTION: This auction takes place on the Ashland Auction Group website bidding platform. Bidding begins 8/17/2026, 10:00 AM. Bidding ends 8/19/2026, 12:55 PM. The list price is the suggested opening bid. Deposit: $5,000. This lot of land is located in the Chestertown area of Kent County. The property is in close proximity to the Chester River. The area provides easy access to the major traffic artery, Morgnec Rd, connecting to the surrounding areas.

Lenapah Rd, Chestertown

Listing courtesy of Ashland Auction Group LLC. Contact: 4104883124
$430,000
4 Beds ⋅ 2 Baths
Step into timeless charm with modern updates in this beautifully renovated early 1900s home located in the heart of Kennedyville. Offering 4 bedrooms, 2 full baths, and a versatile third-floor loft, this home seamlessly blends classic character with today’s conveniences. From the moment you arrive, you’ll be drawn to the inviting wraparound front porch—perfect for relaxing and enjoying small-town living. Inside, the home has been thoughtfully updated from top to bottom, including brand new siding, windows, roof, and HVAC system for added peace of mind. The interior showcases a stunning transformation featuring refinished original hardwood floors, fresh paint throughout, and a completely updated kitchen with granite countertops and brand new stainless steel appliances. Both bathrooms have been tastefully renovated, offering a clean and modern feel while complementing the home’s historic charm. Additional highlights include a convenient laundry/mudroom off the rear of the home and a flexible third-floor loft space—ideal for a home office, playroom, or guest retreat. Out back, you’ll find a detached carriage house equipped with electric (100 amp service), heat, and A/C—perfect for a workshop, studio, or additional storage. Situated in the quaint town of Kennedyville, this property offers the perfect balance of historic character, modern upgrades, and small-town charm.

11944 Augustine Herman Hwy, Kennedyville

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

$2,550,000
5307 Elburn Lane presents a compelling assisted living investment in Maryland’s Eastern Shore, offering immediate operational scale through approved bed expansion. The property currently supports 8 licensed beds, with approved plans to double capacity to 16 beds, significantly enhancing revenue potential without the delays or uncertainties of zoning or permitting. Positioned on ±8.68 acres, the site provides a quiet, residential setting ideal for senior care, while remaining accessible to Rock Hall, Chestertown, and regional healthcare services. The combination of existing operations, expansion approval, and limited competitive inventory makes this offering well‑suited for both owner‑operators and strategic investors

5307 Elburn Ln, Rock Hall

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$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:

$625,000
It is a rare opportunity for a private waterfront lot off the Sassafras River to come available. This 14 acre parcel of land is located above the bridge in a well established small community of Gentle Winds. Scenic and tranquil area for birding watching, kayaking or taking a short boat ride to restaurants located down the river. With this 14 acre lot, there are open areas and woods to play with. Build the house of your dreams and be able to work and play where you live. Short drive to tax free shopping in Middletown DE.

14200 Metasequoia Ct, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$75,000
Seller Says Bring All Offers! This rural 0.38-acre lot presents a unique investment opportunity in a quaint small-town atmosphere. The property is cleared and ready for your building plans, offering a blank canvas for various residential projects. With road frontage, it ensures easy access and visibility, enhancing its appeal for future buyers or renters. Notably, the lot is not currently in development, allowing for flexibility in planning and construction. The absence of existing structures means lower initial costs and the potential for higher returns on investment. The cleared land allows for immediate construction, reducing time to market and maximizing rental income or resale value. Sellers have already invested in the public water/sewer setup allocation and with this property's strategic location positions it as a lucrative opportunity for savvy investors looking to expand their portfolios. With the right vision and execution, this lot can yield significant financial returns in a competitive real estate market. Don't miss out on the chance to secure a valuable asset with great potential.

11930 Kennedyville Rd, Kennedyville

Listing courtesy of Remax Vision. Contact:

$225,000
3 Beds ⋅ 2 Baths
Price Reduced! Three bedroom home in Still Pond. This renovated home has new kitchen, HVAC, baths, carpet, paint flooring and more! Located on .38 acres amenities include covered front and side porch, shed, 1.5 baths, Chestertown is a short drive away with restaurants and shopping. This is a Fannie Mae home, submit all offers on Homepath site.

26663 Maple Ave, Still Pond

Listing courtesy of Real Estate Consultants. Contact:

$415,900
3 Beds ⋅ 2 Baths
REDUCED!! Nestled in the charming Betterton community, this delightful farmhouse-style home offers a perfect blend of rustic charm and modern comfort. With 3 spacious bedrooms and 1.5 bathrooms, the interior features warm wood flooring and a cozy brick fireplace, creating an inviting atmosphere for gatherings. The attic provides additional storage or potential for creative use, while the partial basement adds practicality to your living space. Set on a generous 3.75-acre lot, this property boasts a serene backdrop of trees and open spaces, ensuring privacy and tranquility. Enjoy panoramic views of the surrounding woods, perfect for nature lovers and those seeking a peaceful retreat. The outdoor space is ideal for gardening, play, or simply unwinding in the fresh air. Located in a rural setting, this home is just a short walk from local amenities, including r Betterton beach and boat ramp. The community is known for its friendly atmosphere and strong sense of belonging. Public services are readily available, ensuring convenience and peace of mind. This property is not just a house; it's a place to create lasting memories. Embrace the lifestyle that Betterton offers, where comfort meets community. Lot does have subdivision possibilities. Check with the town manager.

201 Ericsson Ave, Betterton

Listing courtesy of Coldwell Banker Waterman Realty. Contact: (410) 643-5005
$350,000
1 Beds ⋅ 1 Baths
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 aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006168 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit #2B, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$375,000
2 Beds ⋅ 1 Baths
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 aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit #2A, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$200,000
1 Beds ⋅ 1 Baths
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 aspect that this multi-unit building provides. Offering a total of FOUR units for sale as a package, or as individuals. Each unit has been remodeled and upgraded meticulously and thoughtfully with attention to the historical aspects of the building. The Sellers salvaged much of the original moldings, doors and trim to be reused and repurposed throughout the spaces to instill its original character wherever possible. The waterfront offers a floating dock, a BBQ patio & picnic area, kayak and paddle board storage, and the building amenities include off street parking and extra storage space. Choose a unit for yourself and rent the rest of them to cover your payments OR invest and rent them all for a profit! The possibilities with this iconic Chestertown address are endless. 1B – Listed $200,000: the most cozy setting! One bed one bath Garden Level apartment. Exposed bricks, original fireplace structural detailing, and water views and access directly outside the door. BrightMLS: MDKE2006164 1A – Listed for $685,000: three bedrooms and three bathrooms spanning two floors. A walkout lower level to the waterfront, a sweeping covered porch overlooking the Chester River, a four-season sunroom, and a spacious Primary Suite with a walk-in closet and en suite bath with double vanity and tile and glass shower. The modern kitchen offers ample storage, granite countertops, cork tile flooring, and stainless appliances. Two more bedrooms and two additional full baths round out the expansive offerings that are an incomparable setting for Downtown Chestertown waterfront! BrightMLS: MDKE2006162 2A – Listed for $375,000: a two bedroom, one bath suite with 12+ foot ceilings, rooms flooded with light from the tall windows, and stunning Chester River views from every living space. The claw foot tub adds vintage whimsy to a space with modern updates throughout. BrightMLS: MDKE2006166 2B - Listed for $350,000: a one bedroom, one bath with soaring ceilings, gleaming original hardwood floors, the largest bedroom in the building and the most square footage per unit above the main level. Water views from the living & dining room make this spot irresistible. BrightMLS: MDKE2006164 ALL - Purchase one for your weekend pied-à-terre on the Shore! Or… invest in the whole package for $1,600,000! BrightMLS: MDKE2006158 *Condo Association will not allow for vacation/short term rentals (6+ month minimum leases); however, the viability of each space for long term tenancy promises to be lucrative.

117 Water St N Unit #1B, Chestertown

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344