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$549,900
3 Beds ⋅ 3 Baths
Waterfront Living with a Deeded Boat Slip on Cambridge Creek - Enjoy beautiful water views, three screened porches and a deeded deep-water boat slip in this spacious three-level residence in the desirable Waterside community. Thoughtfully designed with approximately 3,000 square feet of living space (per floor plans) the home offers the comfort of a single-family home with the ease of low-maintenance living. The main level features an open floor plan with spacious living and dining areas, well-appointed kitchen with granite countertops, stainless steel appliances, island seating and abundant storage plus a large screened porch overlooking the water. The entry level offers a flexible family room with a full bath and screened porch, ideal for guests, a home office or recreation. Upstairs, the waterside primary suite features vaulted ceilings, large walk-in closet, spacious bath, private screened porch and an adjoining office or sitting area. Just blocks from downtown Cambridge's restaurants, shops, marina and waterfront parks, this exceptional home offers easy access to Cambridge Creek and the Choptank River. Square footage is based on floor plans. Tax records may differ and buyers should verify.

202 Muir St, Cambridge

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$899,999
4 Beds ⋅ 3 Baths
Cambridge - waterfront paradise on Jenkins Creek, offering direct, easy access to the Choptank River! Nestled on a private lot with a peaceful, country feel, this charming home combines serene Eastern Shore living with the convenience of being just minutes from downtown Cambridge. Step inside to bright, sunlit interiors featuring soaring cathedral ceilings and rich hardwood floors. Cozy up on cool winter evenings by the fireplace/ woodstove, or unwind in the spacious main-floor primary suite, complete with a walk-in closet, updated bath with a walk-in shower, and direct access to the deck through large sliding doors framing picturesque water views. Upstairs, you'll find two additional bedrooms, a full bath, a versatile bonus room or potential fourth bedroom, and generous extra space ideal for storage or future expansion. Outdoor living is truly exceptional, featuring two private decks, a welcoming front porch, and a wonderful screened porch perfect for relaxing or entertaining. The rip-rapped shoreline includes a private dock equipped with water and electricity—ready for your boating and fishing adventures. Complete with an attached oversized garage, this captivating coastal retreat has so much to love!

2503 Legacy Ct, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$849,900
3 Beds ⋅ 2 Baths
Imagine waking up to sweeping waterfront views, launching your kayak from your private beach, and ending the day with uninterrupted sunset skies right from your own yard! This stunning, completely remodeled coastal retreat combines peace of mind with exceptional investment potential. Featuring a new roof and new HVAC system, every detail of this home has been thoughtfully updated, including fresh LVP flooring throughout with all-new subflooring and beautifully updated bathrooms. The gourmet kitchen boasts sleek granite countertops, perfect for entertaining family and guests. Step outside to enjoy direct waterfront living with a riprapped shoreline and your very own private beach access—ideal for launching kayaks, soaking up sunset views, or enjoying water recreation. Detached garage. Currently operating as an active Airbnb with a proven rental history, this property is ready to generate income from Day 1. Furnishings are negotiable, offering a seamless, plug-and-play opportunity for vacation home buyers or investors alike.

1648 Taylors Island Rd, Woolford

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to Crump Point, an extraordinary renovated waterfront sanctuary nestled on approximately 5± private acres overlooking the tranquil waters of Church Creek. Offering exceptional privacy and captivating panoramic views, this remarkable property captures the essence of Eastern Shore waterfront living. Thoughtfully designed to embrace its breathtaking surroundings, the 3-bedroom, 2.5-bath residence offers stunning water views from nearly every room. The main level is anchored by a spacious gourmet kitchen featuring an oversized island, creating the perfect space for entertaining or gathering with family while enjoying the picturesque waterfront backdrop. All new stainless steel appliances throughout. The first-floor primary suite provides a private retreat complete with serene waters views, waterside deck, walk-in closet, walk-in shower, and oval soaking tub. Outdoor living is equally impressive with a spacious waterfront deck, screened waterside porch, and an upper-level waterside deck—ideal for morning coffee, evening sunsets, or simply taking in the ever-changing beauty of Church Creek. A private pier offers direct access to the water for boating, kayaking, fishing, and crabbing, while the beautifully landscaped grounds provide ample room to enjoy the peaceful surroundings. Additional features include a circular driveway, attached two-car garage, first-floor split-unit heating and cooling, and second-floor central air with baseboard heat. Whether you’re seeking a full-time residence or a weekend waterfront escape, Crump Point offers a rare opportunity to own an exceptional Eastern Shore property where privacy, natural beauty, and timeless waterfront living come together in perfect harmony.

1619 Perseus Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$624,000
4 Beds ⋅ 3 Baths
Discover the perfect blend of privacy, comfort, and waterfront living with this exceptional move-in-ready Colonial, nestled on 6.01 scenic acres. Offering 4 bedrooms, 3 full baths, and an abundance of versatile living space, this property is ideal as a full-time residence, weekend retreat, or multigenerational home. Wake up to peaceful water views and enjoy your morning coffee on the expansive rear deck overlooking the tranquil setting. Inside, you'll find a spacious country kitchen, a flexible first-floor bedroom or home office, and inviting living areas designed for both everyday living and entertaining. The property is loaded with sought-after amenities, including a private floating dock for boating, fishing, or kayaking, a detached workshop with electricity, heating, and air conditioning perfect for hobbies or storage, and a separate in-law suite complete with its own sauna, providing an ideal space for guests, extended family, or potential rental opportunities. Additional features include a two-car attached garage, an attractive stone walkway with brick front steps, and the peace and privacy that only a rural waterfront setting can provide. Conveniently located just minutes from Cambridge's shopping, restaurants, and schools, while also offering easy access to nearby beaches and major metropolitan areas, this is a rare opportunity to own an affordable waterfront property with acreage, privacy, and exceptional versatility.

5214 David Greene Rd, Cambridge

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$299,000
3 Beds ⋅ 2 Baths
Beautifully renovated and move-in ready, this furnished 3 bedroom, 2 full bath home is nestled in the heart of Sika deer country. This home is in excellent condition, features include beautiful hardwood and luxury vinyl plank flooring, central heating and air, mini splits, a pellet stove and a detached one-car garage with a finished bonus room above complete with electric and a mini-split for heating and air. Outside, enjoy a storage shed, fire pit, an established orchard with pin oak, apple and persimmon trees and a deer feeder that conveys. The nearby public boat ramp and marina provide easy access to the Honga River. Whether you're looking for a full-time residence, weekend getaway or hunting retreat, this turnkey property is ready to enjoy. Backs up to a 350+ acre managed sika deer/farm property. Deer feeder conveys.

2243 Wingate Bishops Head Rd, Wingate

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$50,000
Build your dream home on this scenic 3.53-acre wooded lot in the exclusive Heron Harbor community, nestled along Webbs Creek, which feeds into the Choptank River. Surrounded by water and nature, this peaceful setting offers access to a community pier on navigable water—perfect for kayaking, boating, and enjoying fresh Eastern Shore crabs. HOA fees include dock maintenance and BIP septic hook-up access. With easy access to downtown Cambridge, shopping, restaurants, and more, you’ll enjoy the perfect balance of convenience and seclusion. Embrace the best of Eastern Shore living in this quiet, water-oriented community.

5229 Heron Rd, Cambridge

Listing courtesy of Northrop Realty. Contact: (302) 539-0800
$299,000
3 Beds ⋅ 1 Baths
Welcome to 2517 Old House Point Rd, one of the cutest homes in Fishing Creek. Sitting on elevated ground this three bedroom, one bathroom home has water views from the front and back yard. Large garage you could keep a boat or kayaks and bikes with loft and lean to. Quiet area with relaxing feeling.

2517 Old House Point Rd, Fishing Creek

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$167,900
Great opportunity to own nearly 8 acres featuring some of the highest and driest ground in Toddville. Located in sought after Sika deer country, this property offers a peaceful rural setting with hunting opportunities, abundant wildlife, and a creek running through the property. The land features a great combination of woods, newly planted pines and natural habitat, creating an ideal setting for Sika deer, wildlife and outdoor recreation. Property features a brand new complete 4 chamber septic system (never used), adding value and future potential, existing well. Also conveying is a 27 ft camper with bump out, providing a great setup for a hunting retreat or weekend getaway. The older home on the property is in need of repairs, including a new roof and is being sold as-is, bring your vision to renovate and bring back to life or tear down and build your own home. Enjoy the privacy, open space and natural beauty of Dorchester County with fishing, boating, public boat ramps and marinas close by.

2551 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$367,000
2 Beds ⋅ 2 Baths
WATER VIEWS THROUGHOUT * 1841 sq ft * CORNER CONDOMINIUM HOME * GATED PRIVATE * OPEN CONCEPT * 2 BEDROOMS * 2 FULL BATHS * GARAGE PARKING * 2 ELEVATORS * POOL * PET FRIENDLY* Imagine waking up to water views from every window in your *1841 sq ft* corner condominium home! This gated, private property boasts an open concept, perfect for entertaining. With two bedrooms and two full baths, plus a garage and two elevators, you’ll have plenty of space to enjoy. Plus, it’s pet-friendly! This unit is bright and airy, and you’ll be amazed by the size and volume of the Easton Model floor plan. The 9 ft tall ceilings and lots of large windows fill the space with natural light and offer beautiful views of Cambridge Creek and Trenton St. Marina. The kitchen has a classic, timeless look with stainless appliances, maple cabinetry, and solid surface countertops. The kitchen, which includes a breakfast nook, opens up to the dining, living, and sunroom areas, creating a seamless flow. The sunsets are truly spectacular! This fenced, gated property is secure with security cameras. The condo includes one assigned garage parking spot, plus plenty of overflow parking for you and your guests. Relax and cool off at the onsite pool, pool house with bathrooms and shower amenities, or simply enjoy the sun. The condo is freshly painted in neutral tones, clean, and ready to move in. You’ll also find newer high-traffic laminate flooring and an AC unit with powerful airflow. The energy-saving Aqua Therm combination furnace with a 50-gallon hot water tank system makes heating and cooling efficient. Plus, there’s a convenient locked individual storage room on the main floor. All appliances, including the washer and dryer, are included. This is a second home for the seller, gently used and never rented out. The HOA takes care of the roof, exterior siding, exterior lighting, landscaping, and snow removal. There’s a one-time capitalization fee, a post-settlement fee, and two monthly HOA fees required by the buyer at settlement. This is an outstanding unit, one of the largest available, and a great choice!

700 Cattail Cv Unit #104, Cambridge

Listing courtesy of HomeZu by Simple Choice. Contact: (855) 885-4663
$998,500
4 Beds ⋅ 4 Baths
Exceptional waterfront estate in Dorchester County offers sweeping panoramic views of Church Creek with direct access to the Chesapeake Bay . Also located in the highly sought after Cambridge South Dorchester School District . Featuring over 470 feet of protected shoreline , a private dock with 4 feet of water depth, and a boat lift , this property is a rare opportunity for true waterfront living . The 3400 square foot , two and a half story home is thoughtfully designed to capture stunning water views from every angle . In side you will find four spacious bedrooms , including a grand primary suite , along with two full baths and a half bath on the upper level. The main floor is ideal for both everyday living and entertaining . offering a large waterfront dining room , a cozy water view den , and an expansive living room with a wood burning fireplace . The modern kitchen is beautifully updated and includes a pantry and a covered side porch. A unique extended screened porch off the dining room provides the perfect setting to relax and take in the serene views of Church Creek. Upstairs, the luxurious master suite features walk in closets, and the master bathroom showcases a vintage inspired clawfoot tub , a standout feature for those drawn to a modern farmhouse aesthetic , along side a walk in shower. Step out onto your private deck from the master bedroom to enjoy breathtaking sunsets over the water. Two additional bedrooms share a well appointed bathroom , spacious laundry room includes a new washer and dryer . The third floor offers flexible space with two large rooms , ideal for additional bedrooms , a home office , office gym, or media room . Additional features include multiple outbuildings : a two car garage, a kennel with three bays ready for future fencing , and a separate structure perfect for storage of a office. The property spans three lots totaling 3.395 acres of land , accessed by a long privately owned driveway that ensures ultimate privacy . This truly remarkable waterfront retreat where privacy, natural beauty, and expansive water views come together , an opportunity that must be experienced to be fully appreciated

4928 Gregory Rd, Cambridge

Listing courtesy of Stafford-Stafford Real Estate. Contact: 4103107755
$1,795,000
4 Beds ⋅ 3 Baths
Fabulous waterfront home with modern flair and a stunning indoor pool, ideally located in McKeil Point, offering effortless one-level living and an open floor plan designed to capture spectacular, unobstructed water views from nearly every room. The thoughtfully designed split-bedroom layout ensures privacy, featuring a serene primary suite with direct access to the indoor pool, a luxurious bath, and a private waterside deck. The spacious kitchen includes a center island with bar seating and flows seamlessly into a separate dining room, perfect for entertaining. A light-filled family room opens to both the indoor pool and expansive waterside deck, creating the ultimate indoor-outdoor lifestyle. Set on over 6 acres along scenic Fishing Creek, the property boasts a rip-rapped shoreline, private pier and boardwalk, abundant wildlife, and a two-car side-loading garage, offering a rare blend of tranquility, space, and waterfront living at its finest with the advantage as a valued vacation rental destination.

5227 Brooks Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$455,000
3 Beds ⋅ 2 Baths
Updated 3-bedroom, 2-bath waterfront home on Hudson Creek offers breathtaking water views. Enjoy crabbing, fishing and boating from your very own Hudson Creek oasis. New 90 ft private pier with 10x20 sun deck and 2 boat slips. Enjoy the large yard, rear screened-in porch, waterside gazebo. Features include a 2-car garage, paved driveway, and ideal spaces for relaxation and entertaining. New well, septic, new kitchen and foyer luxury vinyl flooring. New kitchen countertop, new first floor full bathroom, new front door and fresh paint. Bring your boat and enjoy all pleasures this waterfront home has to offers.

5841 Hudson Wharf Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$650,000
4 Beds ⋅ 3 Baths
MAJOR PRICE REDUCTION! A rare opportunity to own a private waterfront retreat that not only offers an exceptional Eastern Shore lifestyle, but also a proven income-producing investment — with over $46,000 in rental payouts over the past two years and an active upcoming reservation calendar, the next owner can enjoy immediate revenue while still reserving time for personal use. Escape the pace of city life and discover your own secluded waterfront sanctuary on St. John's Creek, nestled among 3.5 picturesque acres. Conveniently located within an easy drive of Baltimore, Washington, D.C., and Northern Virginia, this peaceful retreat is surrounded by the natural beauty of Maryland's Eastern Shore, where bald eagles, osprey, herons, ducks, geese, sika deer, and other wildlife are part of everyday life. The charming cottage is filled with warmth and character, offering a welcoming living room with a mantle and pellet stove, a cozy kitchen and dining area, a versatile first-floor bedroom, laundry room with daybed, and a full bath. Upstairs, a spacious bedroom with a half bath and wood stove creates a peaceful, storybook-like retreat. The brick-floored screened porch overlooks St. John's Creek and the private pier, providing the perfect setting for morning coffee, evening cocktails, or simply watching boats and wildlife pass by. Designed for gathering family and friends, the thoughtfully crafted carriage house (guest house/second dwelling) significantly expands the property's versatility. It features a spacious bunk room with six bunk beds, an oversized second-floor bedroom accommodating two queen beds, plus a main level with kitchen, dining area, living room, and full bath. An attached two-car barn-style garage provides additional storage and functionality. Between the cottage and carriage house, the property comfortably sleeps up to 15 overnight guests. Offered fully furnished and completely turnkey, the property is ready to enjoy from day one. Relax around the waterside fire pit, launch kayaks and paddleboards from your private pier, or dine just minutes away at the popular Boats & Hose Restaurant. Due to the property's active vacation rental schedule, showing availability is limited — a comprehensive virtual tour will be available soon, allowing prospective buyers to experience the property while private showings are accommodated around existing guest reservations. Whether you're looking for a private waterfront getaway, a full-time residence, or an investment with established income potential, this property offers the flexibility to do it all. This is a rare opportunity to purchase a turnkey waterfront property with immediate income already in place.

4004 Robinson Neck Rd, Taylors Island

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

$1,250,000
5 Beds ⋅ 4 Baths
🔥 Eastern Shore Waterfront Estate 🔥 Welcome to a true sportsman’s paradise tucked along the shores of the Chesapeake Bay—where space, privacy, and waterfront living come together in a BIG way. Built in 1988 and spanning nearly 5,000+/- square feet, this one checks boxes most properties can’t even reach… 🏡 5 Bedrooms | 3.5 Baths | 4,933+/- Sq Ft Step inside and you’ll find: • A massive eat-in country kitchen (with heated floors 👀) • Formal dining for hosting the big nights • TWO oversized family rooms for spreading out • Space for everyone… and then some But here’s where it gets wild 👇 🎯 Next-Level Extras: • Huge workshop + multiple garage spaces • Dedicated entertainment hall with FULL kitchen, bar & pool table • Built for hosting, holidays, and unforgettable weekends 🌅 Waterfront Lifestyle: • Private pier on Brooks Creek • TWO boat lifts + electric lift • Westerly sunset views over the Bay (the kind people chase 🌅) • Expansive deck for relaxing or entertaining • Private pond adding to the already unreal setting ⚙️ Major Upgrades: • Geothermal system (efficient + smart) • New roof (Oct 2024) • Expanded shop addition This isn’t just a home… it’s a compound. A retreat. A place people don’t want to leave once they get here. 💬 If you’ve been waiting for something special on the Eastern Shore… this is it.

5253 Ragged Point Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$239,000
2 Beds ⋅ 2 Baths
This cozy 2 bedroom, 2 bath condo is nestled in the sought-after waterside community of Deep Harbour. As you enter, you'll be greeted by a bright and spacious living area that flows seamlessly into the kitchen, equipped with modern appliances, sleek countertops, and ample cabinet space. The primary features a private en-suite bath and plenty of closet space, while the second bedroom offers versatility for guests or a home office. Outside, enjoy a private balcony with creek views, or take a stroll along the public riverwalk that outlines the community, with downtown restaurants and shopping just minutes away. Deep Harbour is a gated community with secure assigned garage parking, keypad/fob front building entry, and nearby boat ramps. Enjoy access to a community pool, nearby parks, playgrounds, the Fishing Pier, and the Harriet Tubman Museum & Educational Center in Cambridge. Nature lovers will appreciate the nearby Blackwater National Wildlife Refuge and its Visitor Center. Storage unit included.

900 Marshy Cv Unit #411, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$59,950
Price Improvement — Beautiful Homesite Near the Water in Ferry Farms Take advantage of a rare opportunity to own this 2.20± acre homesite in the sought-after Ferry Farms community. Located just a short walk from the water and the community pier, this property offers a peaceful, private setting bordered by wooded, community-owned open space. The natural surroundings create a tranquil retreat with a scenic, tree-lined backdrop perfect for relaxing and enjoying the outdoors. Whether you’re planning a full-time residence or a weekend escape, this property offers the ideal setting to build your custom home near the water while still enjoying privacy and the beauty of nature. Buyer Notice: Buyers are encouraged to contact the Maryland Department of the Environment (MDE) and Dorchester County Planning & Zoning to confirm all building requirements, including wetlands or Critical Area considerations, possible restrictions, and connection requirements for the community B.I.P. system. Plat, covenants, and restrictions are available in the document section.

814 Cody Dr Unit #LOT 17, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000