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1514 Deep Point Rd, Woolford
$619,900
2 Beds ⋅ 2 Baths
Welcome to your waterfront property! Home boasts nice open living room /dining room area with gorgeous views of the water from the large bay window, and a food bar dividing the rooms. The primary suite allows access to the enclosed sunroom with expansive views of the water. The home features secondary bedroom with water view, a second full bath, a kitchen with a double wall oven, separate cooktop, a bistro area, and a large pantry. Priced with the realization in mind potential buyers may decide to update the kitchen and baths. Property has a second 2 room and bath building. The home is situated on +/- .50 acre. Pier has a 9,000 lb boatlift, swim ladder, water and electric. This home is a Must-See to truly appreciate all it has to offer. Sellers are offering an assumable FHA mortgage at 5.25%. to qualified buyers. Buyer will be responsible to pay sellers the difference between the assumable mortgage amount and the contracted sale price of the home.

1514 Deep Point Rd, Woolford

Listing courtesy of Long & Foster Real Estate, Inc.. Contact:

1661 Town Point Rd, Cambridge
$1,195,000
4 Beds ⋅ 4 Baths
Welcome to a rare Eastern Shore offering where privacy, income potential, and waterfront lifestyle come together on 23± acres along the Little Choptank River. Currently a successful vacation rental, this property presents an exceptional opportunity for a second home that works for you—enjoy it when you want and generate income when you’re away. The expansive acreage provides a peaceful, private setting with endless possibilities—gardening, small-scale farming, hunting, or enhancing the land with an impoundment or pond to attract waterfowl. The waterfront is fully equipped for enjoying life on the water with a partially rip-rapped shoreline, private pier and approximately 2.5 feet of mean low water depth—ideal for boating, fishing, and crabbing, with easy access to Fishing Creek and the Chesapeake Bay beyond. Outdoor living truly shines with an in-ground pool overlooking the water, offering a serene setting for both quiet relaxation and entertaining. The spacious wooden deck provides ample room for dining and gatherings, while taking full advantage of the surrounding views. An outdoor shower adds a practical touch, making it easy to rinse off after time spent on the water or enjoying the outdoors. The 4-bedroom, 3.5-bath residence is designed for comfort and gatherings, offering an open floor plan with two primary suites, each with private baths. The spacious kitchen is a true centerpiece, featuring a large island with breakfast bar, double wall ovens, cooktop, refrigerator, dishwasher, beverage refrigerator, and separate ice maker—fully equipped to handle everything from intimate dinners to large-scale entertaining. The adjacent dining room easily accommodates gatherings, while the family room, just off the kitchen, captures serene water views and opens to a spacious screened porch for seamless indoor-outdoor living. A sunroom adds additional living space, also overlooking the pool and waterfront, creating the perfect spot to unwind year-round. The home’s low-maintenance brick exterior, attached two-car garage with automatic opener, and thoughtful layout make it as practical as it is inviting. Conveniently located approximately 2 hours from Washington, DC and 1.5 hours from Baltimore, this property offers the perfect escape without sacrificing accessibility. Whether you’re seeking a private retreat, an income-producing investment, or a place to fully embrace the Eastern Shore lifestyle—boating, fishing, crabbing, kayaking, paddleboarding, and more—this property delivers. Don’t miss the opportunity to own a truly unique waterfront estate with everything in place for summer enjoyment—schedule your private tour today and start living the lifestyle you’ve been waiting for.

1661 Town Point Rd, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

6706 Whiteley Rd, Hurlock
$174,900
3 Beds ⋅ 2 Baths
Welcome to this ranch-style home, nestled in the serene Hurlock community. With 1,344 square feet of thoughtfully designed living space, this residence features three spacious bedrooms and two full bathrooms with tub shower, ensuring ample room for relaxation and privacy. Venture inside to discover a warm and inviting atmosphere showing a spacious living room that opens to a combined kitchen and dining area that encourages gatherings and shared meals. Natural light pours in through well-placed windows, enhancing the cozy ambiance throughout the home. The screened porch invites you to unwind while enjoying the gentle breeze and views of the expansive half-acre lot, perfect for outdoor activities or simply soaking in the tranquility of your surroundings. The driveway provides convenient off-street parking. Don't miss the opportunity to make this home yours!

6706 Whiteley Rd, Hurlock

Listing courtesy of Century 21 Downtown. Contact:

202 Buena Vista Ave, Cambridge
$339,000
3 Beds ⋅ 2 Baths
SELLER WILL CONTRIBUTE UP TO FIFTEEN THOUSAND DOLLARS ($15,000) TOWARDS BUYER CLOSING COST. WATER ACCESS - VERY LIMITED "BUT" a small boat could provide you limited duration of access to the Choptank River. A great opportunity to enjoy the charm of Eastern Shore living. This 3 BR, 2 BA home features open layout connecting kitchen to dining and living rooms offering optimal natural lighting. Each boasting large window allowing for scenic outdoor viewing. New kitchen stainless steel appliances and cabinetry along with new countertop and backsplash. Backyard offers large, detached 2 car garage, privacy and solitude overlooking Canal leading to the Choptank River. Located just minutes from downtown historic Cambridge, shopping, and local marinas.

202 Buena Vista Ave, Cambridge

Listing courtesy of Eastern Shore Properties, ESP Inc.. Contact:

5816 Indian Quarter Rd, Cambridge
$675,000
3 Beds ⋅ 3 Baths
Do you dream of a serene waterfront escape with room for horses, privacy, and the opportunity to create something truly special? Recently PERC APPROVED for a 5-bedroom home, this 10-acre horse farm on Hudson Creek offers exciting new possibilities to renovate the existing residence or build the waterfront home you’ve envisioned. The property is already well equipped for equestrian use with two fenced pastures, a barn, run-in shed, storage shed, and fresh water systems for the horses. Surrounded by wide-open space and limited future development, the setting offers exceptional privacy and peaceful, protected views. Water lovers will appreciate the 100-foot T-shaped pier with over 4 feet of mean low water on protected Hudson Creek, providing easy access to the Chesapeake Bay and some of the area’s best fishing and crabbing. A charming old crab shack near the shoreline offers additional potential with some repairs. An oversized detached brick 4-car garage provides plenty of room for a workshop, hobby equipment, boats, or collectible vehicles. The existing all-brick home is being sold AS IS and features three bedrooms, two-and-a-half baths, a brick fireplace, and attached 2-car garage. With 10 waterfront acres, established equestrian amenities, deep-water access, and the recent 5-bedroom PERC approval, this property presents a rare opportunity to bring your vision to life on Maryland’s Eastern Shore.

5816 Indian Quarter Rd, Cambridge

Listing courtesy of Sharon Real Estate P.C.. Contact:

3 Talbot Ave, Cambridge
$369,990
3 Beds ⋅ 2 Baths
Beautifully renovated 3-bedroom, 2-bath home located next to Jerry Boyle Park with water views of the Choptank River. This move-in-ready gem offers modern updates throughout, inside and out. Enjoy cooking and entertaining in a spacious kitchen with granite countertops, stainless steel appliances, and recessed lighting. The home features luxury vinyl plank flooring, on-demand hot water heater, and a new HVAC system for year-round comfort. Additional updates include new windows and an updated electric panel. Relax in the bright sun porch, or enjoy the landscaped yard with two storage sheds for all your outdoor needs. Whether you’re looking for a primary residence, vacation home, or rental investment, this one has it all. Property Highlights: •

3 Talbot Ave, Cambridge

Listing courtesy of Cottage Street Realty LLC. Contact: