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$339,000
2 Beds ⋅ 2 Baths
Come make your home in Betterton - the Jewel of the Chesapeake - where the Sassafras meets the Bay! Small town charm makes this an especially beautiful place to live - year round or as a well loved second home! Carefree living in a completely renovated complex with so much to offer - charming updated condo with main floor living and access to a saltwater pool, sandy beach with picnic area, bathhouse, and boat ramp plus a deeded 30' boat slip with an 8,000 lb lift with new motor, new cables, remote control and dock box. The boat dock is accessed via the private gated dock on the Sassafras. This home includes a lovely expansive covered porch and large protected storage area underneath for all the toys! Historic Chestertown and the waterman's town of Rock Hall are just short drives away with a variety of dining and shopping options in both of these waterfront towns. There is a lot of value to be found here for a very reasonable price!

1 Bayview Rd Unit #19A, Betterton

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

$559,500
3 Beds ⋅ 2 Baths
There's a joyful feeling here that takes you straight back to childhood summers on the water. The Kinnairds Point community and property itself delivers this on just over two private acres at the end of a quiet cul-de-sac in Worton. Fully remodeled in 2020, the home opens into a vaulted great room with an exposed beam ceiling and a brick fireplace, flowing into a gorgeous, move-in-ready kitchen finished in crisp white cabinetry and a farmhouse sink. The owner's suite offers a spacious walk-in closet and an amazing renovated bath, while a screened porch and picnic lawn keep everyday living just as easy outdoors. The screened porch is designed for sharing beautiful moments and taking in nature. The full basement allows you to keep all of your "toys" tucked away while still keeping your cars in the garage. Best of all, Kinnairds Point offers access to two private Chesapeake waterfronts each with its own beach, pavilion, and kayak storage, one with a boat ramp just a walk or golf cart ride from your door. Crab pots, boat cruises, and sunset chairs are all in your future. Come life the Eastern Shore lifestyle in a polished setting just minutes from Historic Chestertown.

12613 Walnut Valley Ct, Worton

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

$725,000
3 Beds ⋅ 2 Baths
Set on a moderate bluff along the upper Sassafras River, this inviting waterfront property offers pristine, natural down river views and exceptional access to the water. Enjoy your private dock, boat lift, and plenty of space for kayaks, paddleboards, and other water toys. The home features three bedrooms plus a walkout basement ready for your vision—ideal for creating additional living space, a recreation area, or guest accommodations. With easy access to points north and located less than 10 minutes from Middletown, Delaware, this property is perfectly suited as a weekend getaway or a comfortable downsized waterfront retreat.

32745 Hunt Ln, Galena

Listing courtesy of Gunther-McClary Real Estate. Contact:

$269,000
3 Beds ⋅ 2 Baths
Welcome to Chesapeake Landing! Come see this amazing home offering vaulted ceilings, huge master bath, open concept, plenty of closet space, laminate flooring, and a private secluded fenced lot. Located in a water oriented neighborhood with community boat ramp and pier and nearby restaurants and marina. Move here and enjoy all the Eastern Shore has to offer!

10540 Tonopah Rd, Chestertown

Listing courtesy of Doug Ashley Realtors, LLC. Contact:

$2,150,000
4 Beds ⋅ 4 Baths
Luxury deep water retreat on the Sassafras River: an exceptional custom waterfront crafted residence Offering expansive river views, a private dep water pier, resort style amenities and distinctive natural timber architectural. The custom log construction adds warmth, character and architectural distinction throughout the home The current owners had their 70 ft boat docked there for 10 years with space for several boats to be docked as well. INDOOR POOL looking to the outdoors, situated on a DOUBLE LOT, with a glass enclosure and loads of space to entertain! There are 2 separate upper-level quarters, one for guests which includes a family room, sitting room and full bath. So much potential to utilize at least 2 of the rooms for bedrooms. The primary suite on the other side of the home includes 2 walk-in closets, a dressing room. full bath with soaking tub, an office space and a sitting area with waterfront views. 3 bedrooms with potential to have 5 bedrooms. Set on the tranquil shores of the Sassafras River, this striking custom-built home, blends timeless craftsmanship with resort-style amenities—perfect for effortless entertaining and relaxed waterfront living. The great room includes soaring beams, walls of glass, and panoramic river views Deep water frontage with private pier, 3,000 lb. boat lift and ideal for larger boats as well, crabbing, fishing, and sunset cruising. Year‑round indoor pool pavilion with lounge seating, beverage bar, and easy walk-out. Chef’s kitchen featuring premium appliances, expansive island, and seamless flow to dining and outdoor spaces. Multiple decks and patios for al fresco dining, plus level lawn to the water’s edge. There is even a small kitchenette in the garage for those hardcore entertainers! A full house generator is also present and 3 HVAC units to cool the home. This home would make an amazing Air B and B! There is an additional cabin with sleeping bunks and amenities for those overnight guests that never want to leave. Please click on the walkthrough tour and floor plans are also available.

31436 Sassafras River Ave, Galena

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
$1,375,000
4 Beds ⋅ 5 Baths
Welcome to 22470 Fairgale Farm Ln, a spacious home and property perched over Fairlee Creek, with an assigned boat slip.  3.55 acres, partly wooded, exceptionally landscaped, and perfectly framed water views. Walk down to the water to enjoy the views or launch a kayak.  The deep-water boat slip, outfitted with a boat lift, is just a short distance away. The home features 4 bedrooms and 5 full bathrooms, plus a large loft that could be used as an additional bedroom. The large eat-in kitchen has expansive windows that perfectly frame the water view. A great spot for entertaining! Doors in the kitchen lead to the waterfront deck, spanning the front of the home.  A new roof was installed in June, 2026. In both sitting rooms, you’ll find fireplaces that have been conveniently updated to propane. The first-floor primary bedroom opens up to the waterfront deck and offers a fantastic water view, as well as a large bathroom that was recently updated.  Upstairs you’ll find two waterfront bedrooms, one with an updated attached bath. There's a second full bathroom and ample closet space in the hallway.  Downstairs, there are two additional full bathrooms and a large bedroom. Above the kitchen sits the light-filled loft, a great office, studio, or extra bedroom.  The exterior has a generous front porch, outdoor shower, circular drive, 2-car garage, fenced dog run, and additional garage space connected to the basement.  This light-filled waterfront property is located 15 minutes away from the waterfront community of Rock Hall and historic Chestertown.

22470 Fairgale Farm Ln, Chestertown

Listing courtesy of Gunther-McClary Real Estate. Contact: