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$1,650,000
7 Beds ⋅ 7 Baths
Nestled on the private four-acre waterfront enclave of Three Creeks Point, this extraordinary estate offers breathtaking sunrises and sunsets over Fishing Creek with sweeping southerly views of Church Creek spanning more than 180 degrees. The primary residence features 5 bedrooms, 4.5 baths, and over 5,400 square feet of thoughtfully designed living space, complemented by an expansive maintenance-free wraparound deck providing panoramic water views from nearly every angle. Enhancing the main residence is a separate 2-bedroom, 1.5-bath guest home featuring a Primary Bedroom on the 1st floor with full bath and additional bedroom in the loft with adjoining half bath. The guest home is complete with a full kitchen, laundry, private deck, and tranquil water vistas — ideal for hosting guests or multi-generational living. Just minutes from the open Chesapeake Bay, this property boasts approximately 6 feet mean low water (MLW) along the protected waters of Fishing Creek, creating exceptional opportunities for boating, fishing, crabbing, paddleboarding, and kayaking along the quiet creeks of the Little Choptank River. The L-shaped pier is fully equipped with an electric boat lift, jet ski lift, and multiple slips, offering ease of waterfront access. Recent extensive exterior improvements and renovations have enhanced both the low-maintenance appeal of the property and maximized the stunning waterfront views. Inside, the home showcases a spacious open layout perfect for everyday living and entertaining. The Great Room is filled with natural light and opens seamlessly to the wraparound deck, creating a remarkable indoor-outdoor flow. The Brand-New 2025 Kitchen is the heart of the home, completely remodeled with high-end finishes and designed to serve both the casual homeowner and the enthusiastic entertainer alike. New hardwood flooring throughout the first floor elevates the living spaces while maintaining warmth and coastal elegance. Formal living and dining areas provide refined entertaining space anchored by a stunning stone fireplace, while the sunroom, spanning the width of the home, delivers captivating eastern, western, and southern water views that shift beautifully throughout the day. The main level includes two bedrooms and a full bath tucked into a private alcove, offering comfortable guest accommodations or flexible living options. The upper level hosts the impressive primary suite, complete with vaulted ceiling, fireplace, private waterside balcony, spa-inspired ceramic tile bath with walk-in shower, and spacious walk-in closet. Two additional bedrooms and a full bath are also located on the second floor. An oversized office with vaulted ceiling and its own balcony provides an inspiring remote workspace overlooking the water. The guest house is equally inviting, featuring a first-floor bedroom and bath, full kitchen, stacked washer and dryer, and a second-floor bedroom with loft area — perfect for extended stays. A detached four-car garage offers ample storage for vehicles, water toys, and workshop needs. With its unrivaled waterfront views, deep water access, private setting, generous living spaces, updated interior features, guest accommodations, and extensive dock amenities, this exceptional property represents the pinnacle of luxury Eastern Shore living.

5202 Heron Road, Cambridge

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

Selling Office: .

$1,500,000
This commercial listing presents a prime investment opportunity. Built in 1986 and located on a spacious 2 acre lot, this property boasts a recently completed new roof (2025). In addition, ample private parking is available, enhancing accessibility for tenants and clients alike. With no association fees and owner-paid utilities such as sewer and trash collection, operational costs remain low, maximizing your return on investment. There is significant growth potential in expansion, management, rent growth, and capital improvements. Contact the Listing Broker for additional information.

Hurlock

Listing courtesy of NAI Coastal. Contact:

Selling Office: .

$1,395,000
7 Beds ⋅ 7 Baths
Welcome to Captain's Quarters on the Bay, an extraordinary 3+/- Acre waterfront Estate overlooking the Little Choptank River with direct access to the Chesapeake Bay. Just moments to downtown Downtown Cambridge, fine dining, shopping, and entertainment, this stunning waterfront home offers 5780+/- sq. ft. of three-story living designed for endless indoor/outdoor entertainment and sunset/water views. Inside the home offers deluxe living complete with designer furnishings, large wrap around covered porches, with awesome water and sunset views. Two kitchens, one downstairs for poolside service and a new Gourmet Kitchen on the main living floor offering a large flat top stove, triple ovens, under the counter ice maker and 2 dishwashers for making great family meals. A large Rec-room with large screen TV, games, air hockey, XBOX360 and pool table provides space for everyone. One full bath off the family room provides easy access to the pool area. Outside of the home enjoys a fenced gunite pool w/expansive covered patio, gazebo, paver-lined walkways, pool closet for pool toys, and large garage for lawn equipment and extra storage. A private dock with kayak ramp and stand close by, year round hot tub, basketball court, shuffle board, splinter free playground, large manicured waterfront lawn with a horse shoe pit, double fireplace, built in charcoal grills, and outdoor fire pit make for great outdoor activities for all ages. Finally, for the hunting enthusiast, there is a licensed off shore blind with room for you and your friends to enjoy the great outdoors. With 7 Bedrooms and 6.5 Baths, bring your family and friends to enjoy all the indoor/outdoor activites the Eastern Shore has to offer. The world renown Hyatt Regency waterfront golf course is less than 7 miles away and is open to the public.

1313 Broadview Drive, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,300,000
4 Beds ⋅ 4 Baths
Welcome to a rare waterfront retreat on Hudson Creek offering 30± acres of privacy, recreation, and breathtaking natural beauty with easy access to the Chesapeake Bay. With over 1,000± linear feet of shoreline and stunning water views throughout, this exceptional property is perfectly suited for boating, fishing, hunting, or simply relaxing and taking in the peaceful surroundings. The property features an extended private pier complete with boat lift, providing direct and convenient water access for all your waterfront activities. A significant bonus is the DU impoundment ideal for waterfowl habitat. The home offers 4 spacious bedrooms and 3 full baths and 1 half bath, designed to accommodate both comfortable everyday living and entertaining. A massive great room and dining area serve as the centerpiece of the home, highlighted by an open balcony that surrounds the space and creates a dramatic, airy feel. Dual stairways provide access to the upper level, adding both functionality and architectural appeal and water views. The eat-in kitchen includes a center island and stainless steel appliances, ideal for gatherings and casual dining. A bright and inviting sun porch offers the perfect place to enjoy morning coffee or unwind while overlooking the water. Additional features include a laundry/utility area, welcoming front porch, and a rear porch that further captures the serene water views. Outside, you’ll find a storage shed and a detached two-car garage, offering ample space for equipment, vehicles, and recreational gear. Whether you’re seeking a private waterfront residence, a weekend escape, or a recreational haven (boating, kayaking, fishing and hunting), this unique property delivers unmatched space, versatility, and waterfront living.

5704 Ross Neck Road, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,295,000
3 Beds ⋅ 3 Baths
This beautifully maintained 3/4-bedroom home situated on 4.3 +/- acres offers panoramic wide-water views and exceptional outdoor living. Updated kitchen with granite countertops and a primary bathroom with steam shower. This home blends comfort and style. Enjoy cozy evenings in the sunken living room with a classic wood-burning fireplace. Recent upgrades include a new roof, siding, and HVAC system for peace of mind. Recent BAT septic system. Outdoor amenities abound, including a 20’ x 40’ heated in-ground pool with spa, a spacious 2-story deck, and a screened porch perfect for relaxing or entertaining. The property also includes an attached garage plus a conditioned, detached 3-bay garage with a pool house and a second-story guest suite. A large oil-fired generator ensures uninterrupted power. Surrounded by mature pine trees, this home is a private riverside haven just minutes from Cambridge.

5470 Moose Lodge Road, Cambridge

Listing courtesy of Powell REALTORS. Contact:

Selling Office: .

$1,290,000
4 Beds ⋅ 3 Baths
Beautiful waterfront on Madson Bay! Rarely do you find a property with your own private beach. This exceptional property checks all the boxes. 22+ acres. 10 acres are wooded, 2 ponds, 890 ft of shoreline, a sandy beach and a 3 bedroom, 2 bath guesthouse on the end of a private cul-de-sac. This impeccable home offers 4 bedrooms, 3 full baths, upper/lower decks, large screen porch, 3 car garage and a partial basement. When entering the foyer, to the right it opens up to the stunning living room with beamed cathedral ceilings, hardwood flooring, brick wood burning fireplace. The beautiful bay window enhances the room with natural sunlight. From the foyer to the left steps down to the stunning waterfront kitchen with granite countertops, stainless steel appliances, beverage cooler, induction cooktop, island, recessed lighting and beautiful view of the beach. To the right of the kitchen is the formal dining room with beamed cathedral ceiling, hardwood floors, built-in shelving. Off of the dining is the screened porch/sunroom with water views. To the left of the kitchen steps down to the family room. The family room is the heart of the home with hardwood floors, built-in shelving, double sliding glass doors that opens up to the large deck with broad water views and the sandy beach. The main floor also has 1-bedroom, full bath, laundry room and entry to the partial basement. The second floor offers the primary suite which spreads over the entire back of the home. Imagine waking up every morning to breath taking water views and the smell of fresh air. Enjoy your morning coffee on your private balcony or relax in the soaking tub in the gorgeous primary bath with views of Madson Bay. The large primary bath has 2 walk-in closets, skylight, double tiled shower and double sinks with granite countertops. To the left of the primary bedroom is a cozy sitting room where you can cuddle up, watch a movie or read a good book. The second floor also has a full bath with skylight and 2 bedrooms. HAVE I GOT YOUR ATTENTION? This waterfront Oasis is a MUST see. There is so much to enjoy. Boating, kayaking, canoeing, water skiing, fishing, crabbing, swimming or just relaxing on the sandy beach, swim spa and hot tub. Oh, did I mention the 10 acres of woods and 2 ponds and the abundance of wildlife that roams the property. Look out across the property and see Whitetail deer, Sekia deer, fox and turkey. The 2 ponds are filled with duck and geese and maybe a few fish. The guesthouse would make a great weekend rental or a get-away for family and friends. Main house or guesthouse has never flooded. You can get a permit for a pier. Water depth for pier is 5-6 ft on low tide. Click on the last photo for virtual video.

4906 Timbermarsh Lane, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,252,098
"Legacy" is a legendary 249± Acre Premier Hunting & Recreational Estate | Taylors Island, Maryland Opportunities to own a property of this caliber are exceptionally rare. Encompassing 249± acres in the heart of Maryland's legendary Eastern Shore, this remarkable Taylors Island estate represents the pinnacle of private hunting and recreational land ownership. This property has not traded hands in nearly 100 years. A diverse landscape of mature timber, 17+/- acres tillable ground, tidal marshes, secluded ponds, and winding trails creates an extraordinary wildlife sanctuary that is as beautiful as it is productive. This is the type of property that generations dream about—a place where every sunrise brings the promise of unforgettable outdoor experiences. Renowned for producing outstanding populations of both the iconic Eastern Shore sika deer, whitetail deer, turkeys, waterfowl, and more, Taylors Island has earned its reputation as one of the Mid-Atlantic's premier hunting destinations. The surrounding tidal marshes, forests, and agricultural landscape provide exceptional habitat for deer, wild turkey, waterfowl, and countless other wildlife species. Plenty of established trails provide effortless access throughout the property for ATVs, side-by-sides, hiking, horseback riding, and habitat management. Whether you're slipping into a stand on a crisp October morning, chasing bugling sika during the rut, setting a spread for waterfowl, or simply enjoying the serenity of Maryland's coastal wilderness, every acre has been crafted by nature for recreation and adventure. Beyond hunting, the possibilities are endless. Create the ultimate family retreat with full electric at the camp site, establish a private sporting estate, enjoy camping and wildlife photography, or simply invest in one of the Eastern Shore's most sought-after recreational landscapes. With its unmatched diversity of habitat, exceptional privacy, and incredible sporting opportunities, this property offers an experience that few can replicate. Located on historic Taylors Island—an area celebrated for its expansive Chesapeake Bay marshes, forests, boating, crabbing, and world-class outdoor recreation—this legacy property offers both seclusion and convenient access to the Eastern Shore's amenities. Properties of this magnitude and quality seldom become available. Whether your vision is to build a family legacy, establish an elite hunting destination, or invest in one of Maryland's finest recreational properties, this extraordinary 249± acre estate stands in a class of its own. Legendary properties aren't bought every day—they're passed from one generation to the next. Schedule your private tour today and experience one of Taylors Island's finest sporting estates.

Hoopers Neck Road, Taylors Island

Listing courtesy of Charis Realty Group. Contact:

Selling Office: .

$1,200,000
5 Beds ⋅ 5 Baths
Stunning Classic Greek Revival Architecture Home on Jenkins Creek, just minutes from Downtown Cambridge. Enter the extended blacktop lane off Horns Point Rd until you arrive at the circular drive of this beautifully appointed 5 Bedroom, 4 1/2 Bath, waterfront home with water views from almost every room. The home sits on an elevated 3.3+/- acres with approximately three miles of unobstructed water views, a 60'+/- pier, and over 500’+/- of shoreline on Jenkins Creek, a tributary of the Choptank River. This meticulously maintained turn of the century waterfront home has water views from every vantage point, walnut trees, a peach orchard, and a gardening plot. Whether it's sitting around the pool or swinging on the wrap around porch, there's nothing like watching the endless flow of waterfront wildlife activity. The location of this home provides easy access, either by boat or car, to the many amenities the Shore has to offer. If you love fishing or crabbing, leave your dock and within minutes you will be in the majestic Choptank River, gateway to the Chesapeake Bay. You can put a crab pot off the dock in the early AM and possibly have dinner before nightfall. The property has an oversized five car garage with plenty of storage. The garage second floor has numerous possibilities, and is waiting for the new owners to make it their own. Many of the home’s period furnishings could be purchased separately. Come check out this unique property, we think you will love it!

2208 Horns Point Road, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$1,100,000
3 Beds ⋅ 3 Baths
Cambridge - waterfront retreat! Brand new roof! Nestled on 2.2 serene acres just minutes from Cambridge, this beautifully maintained one-level home offers the perfect blend of comfort, space, and functionality. Inside, you'll find 3 spacious bedrooms, 2 1/2 baths plus a dedicated office—ideal for working from home or flexible living. The dining area , and cozy gas fireplace adds warmth and charm to the main living space. Enjoy seamless indoor-outdoor living with a large screened porch, perfect for relaxing or entertaining while taking in tranquil water views. The house is situated and designed so that every room has a stunning view. Large kitchen, with living/dining area. Generous attached garage. The detached shop/shed offers two covered parking spaces and large finished hobby/workshop with heating and cooling. Perfect for vehicles, hobbies and storage. With one-floor living and thoughtful details throughout, this property offers an unmatched lifestyle in a peaceful, picturesque setting.

2210 Horns Point Road, Cambridge

Listing courtesy of Powell REALTORS. Contact:

Selling Office: .

$1,060,000
4 Beds ⋅ 3 Baths
Stunning Waterfront Contemporary on Church Creek Tucked away on a serene, pine tree-lined drive, this meticulously maintained and architecturally striking waterfront home offers privacy, comfort, and refined craftsmanship just minutes from Cambridge. Designed for modern living with timeless appeal, the property boasts breathtaking views, southern exposure, and a protected shoreline with rip-rap and living shore features—perfect for nature lovers and water enthusiasts alike. The thoughtfully designed main residence features a first-floor primary suite, glowing wood floors, a cozy gas fireplace, and an upgraded kitchen with granite countertops and a sunny breakfast area. Energy efficient geo thermal heat system.. Upgraded cedar impressions siding. Enjoy year-round greenery in the attached greenhouse or relax on the expansive deck with a retractable shade, ideal for entertaining or quiet reflection. An airy loft area provides flexible space—perfect for guest overflow, a home office, or a fun kids’ bunk area. Custom built-ins throughout offer generous storage and showcase attention to detail at every turn. The guest quarters include a private 2BR/1BA suite plus kitchen—ideal for visitors or multi-generational living—alongside an attached garage, workshop for your creative or practical needs. Custom 2 story storage building 24 x 20 (720 sq. ft with 2nd floor) with electric service offering additional space for hobbies or secure storage . Additional features include geo-thermal heating (providing perfect all season environmental conditions) and a tankless hot water heater (energy efficient home), a dedicated wine room, and a spacious laundry room. With its private dock, tranquil setting, and blend of luxury and function, this one-of-a-kind property is a rare opportunity to enjoy Chesapeake living at its finest. South Dorchester school district. Featured on the Delmarva Home Show - play it from Virtual Tours!

1701 Perseus Road, Cambridge

Listing courtesy of Powell REALTORS. Contact:

Selling Office: .

$1,000,000
Originally constructed in 1961, this 20,780 SF building sits on 2.19 acres and was purpose-built as a warehouse before being converted to a bowling alley, showcasing the property’s structural flexibility. The existing improvements are largely non-structural, allowing the building to be efficiently converted back to functional warehouse, distribution, storage or industrial use. The building features 18–20 foot clear ceiling heights, providing strong utility for modern industrial users. Offered at $52.45 per square foot, the asset presents a compelling value-add opportunity for investors or owner-users seeking adaptable industrial or storage space in a centrally located market with immediate access to Route 50.

1200 Goodwill Avenue, Cambridge

Listing courtesy of SVN/Miller Commercial Real Estate. Contact:

Selling Office: .

$995,000
4 Beds ⋅ 3 Baths
Step into the elegance of a 50-acre waterfront estate steeped in timeless charm. Built in 1920, this Neo-Classical Eastern Shore property offers the perfect combination of sophistication and natural beauty. The property is awaiting the perfect buyer who can transform it back to the style and charisma of it's earlier days. Enjoy a bright, welcoming interior. The main house features a large center hall foyer that leads to a stunning living room with a brick fireplace, custom-built shelving, and dual French doors opening into a sunroom. Bask in serene waterfront views from the sunroom, complete with hardwood flooring and another brick fireplace—a space designed for entertaining or quiet retreats. Create unforgettable dining experiences in a formal dining room highlighted by Black Walnut paneling, tasteful wall sconces, and a custom-built wine glass cabinet. The enclosed side porch, fitted with vintage touches like brick flooring, laundry amenities, and the original farmhouse enamel sink, doubles as a mudroom. Meanwhile, the waterside screened porch invites al fresco dining with picturesque views of Church Creek. The second floor offers practicality and comfort with four bedrooms and two bathrooms, accommodating family and guests with ease. A walk-in cedar lined closet and another walk-in attic closet offer a surprising amount of storage. Enhance your lifestyle with additional perks. A thoughtfully updated guest cottage (2019) offers two bedrooms, one bathroom, a kitchen, a living room, a dining area, and laundry facilities—currently enjoyed as a vacation rental. Wildlife thrives here: expect visits from ospreys, bald eagles, and white-tail deer in an atmosphere guests rave about. Relax poolside with a redesigned in-ground pool (2022) boasting a paver deck, modern landscaping, and fencing—all with views of Church Creek. A 28 x 42 wooden barn with concrete flooring, with space sufficient for garage/vehicle or boat storage, and an upper story is complemented by a four-stall stable and additional sheds. The barn built in 1960 was built using reclaimed wood from old chicken houses. Environmental stewardship defines this property. Placed in an Environmental Trust, the land remains protected, ensuring its use promotes nature and agriculture. Boating lovers will appreciate the creek’s access to the Chesapeake Bay, renowned for crabbing, fishing, kayaking, and paddle boarding. Let your vision breathe life into this stunning space. This estate pairs historical allure with limitless possibilities for those ready to turn dreams into reality.

4910 Gregory Road, Cambridge

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

Selling Office: .

$975,000
3 Beds ⋅ 3 Baths
Welcome to a rare and breathtaking opportunity on Hoopers Island—72+ acres of pristine natural beauty offering over 3 miles of private shoreline along the Chesapeake Bay and Honga River. This one-of-a-kind property is a hunter and angler’s paradise with unmatched access to fishing, hunting, and water recreation, all from your own private peninsula. Whether you're drawn to the tranquil rhythms of the Bay, the call of the wild, or simply a desire to escape to unspoiled waterfront seclusion, this turn-key coastal ranch delivers an experience like no other. Elevated on a post and pillar foundation, this raised ranch-style home features wrap-around decks with panoramic views of the surrounding waterways, wetlands, and woodlands. Inside, you'll find vaulted ceilings with tongue-and-groove wood planks, shiplap and board-and-batten walls, and beautifully crafted custom woodwork and barn doors throughout. The open-concept kitchen boasts wood plank ceilings, a coffee station, abundant windows that flood the space with natural light, and a dining area that overlooks the water. The adjoining living area features crown molding, soft neutral tones, and scenic views from every angle. The home features three bedrooms and two full baths, including a bayfront primary suite with custom barn doors that open to a beautifully designed en suite. The bath showcases a handcrafted wood vanity with elegant glass vessel sinks, a spacious walk-in shower, and is finished with shiplap walls and wood-plank ceilings for a warm, coastal feel. Additional bedrooms feature crown molding, ceiling fans, and soothing color palettes. A modern hall bath continues the aesthetic with shiplap accents and another walk-in shower. There are two private docks and a boat launch for easy access to the Bay. Three ponds and surrounding woods offer prime conditions for Sika deer, duck, wildfowl, and turkey hunting. A private sandy beach invites you to swim, kayak, or simply relax by the water’s edge. Under the home, there’s an outdoor shower, a fish cleaning station, covered car and boat storage, and a ground-level storage area with a half bath for convenience after a day outdoors. The lot is partially wooded with trails, wetlands, and complete seclusion, making it an ideal place to reconnect with nature. Described as “a hunting camp your wife actually wants to come to,” this property seamlessly blends rustic charm with modern comforts. It’s not just a home—it’s a private escape immersed in nature, where sunrises and sunsets paint the sky over endless water views. Minutes from Blackwater National Wildlife Refuge and the Harriet Tubman Underground Railroad Museum and convenient to Cambridge for dining, shops, and local amenities, this is a truly extraordinary property offering the best of the Eastern Shore.

2765 Hoopers Island Rd, Church Creek

Listing courtesy of Northrop Realty. Contact:

Selling Office: .

$975,000
Cambridge - 16 Unit residential apartment building with 3+ commercial spaces. Located across from the Health Department building.

612-616 Race Street, Cambridge

Listing courtesy of Powell REALTORS. Contact:

Selling Office: .

$960,000
3 Beds ⋅ 2 Baths

24 Bellevue Avenue, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$950,000
3 Beds ⋅ 2 Baths
Rare opportunity to own a 30-acre waterfront farm along the serene shores of Hudson Creek on Maryland’s Eastern Shore. With 839 feet of shoreline, partially bulkheaded and improved with a private pier, this property offers the ideal setting for boating, fishing, and crabbing in protected waters just moments from the Little Choptank River and the Chesapeake Bay. A perfect blend of open and wooded land, the acreage provides both productive tillable fields and natural habitat—making it equally suited for farming, recreation, or a private retreat. Outdoor enthusiasts will appreciate the exceptional hunting opportunities with abundant goose, duck, deer, and turkey. The solid brick rancher, built in 1969, has been well maintained and offers great bones, presenting a wonderful opportunity for renovation or customization to suit your vision. A substantial metal outbuilding with a concrete floor adds versatility for equipment storage, workshop use, or hobby space. Whether you’re seeking a working farm, weekend getaway, or a waterfront estate to reimagine, this unique property captures the essence of Eastern Shore living—peaceful, private, and rich in natural beauty.

5726 Ross Neck Road, Cambridge

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

Selling Office: .

$950,000
4 Beds ⋅ 4 Baths
Elevated on the banks of the Choptank with sweeping, unobstructed water views, this 4-bedroom, 3.5-bath home was thoughtfully expanded and updated in 2013 to capture the very best of Eastern Shore living. Enjoy the outdoors from multiple vantage points—whether it’s the waterside wraparound deck, the second-floor screened porch, the covered front porch, or a hammock strung between the pines. Professionally designed landscaping provides both beauty and privacy, with lush gardens that attract nature and even produce an abundance of figs from three varieties of bushes—perfect for homemade jams and jellies. The shoreline is fully bulkheaded with a stone jetty, while the L-shaped pier—with pilings already in place for a future lift—makes boating effortless. Inside, the first-floor primary suite offers comfort and convenience with a spacious walk-in closet and full bath, creating the option for single-level living. Upstairs, you’ll find three additional bedrooms and two baths, including one en suite, plus a hardwood-floored office or family room that opens directly to the screened porch. From this ideal location, the Choptank River becomes your playground—swimming, water skiing, fishing, and exploring nearby creeks and waterfront restaurants are just minutes away. Additional features include geothermal HVAC for energy efficiency, a full basement for hobbies and storage, an attached one-car garage, and a detached two-car garage. Waterfront opportunities of this caliber on the Choptank are rare. Don’t wait—schedule your private showing today and make this exceptional property yours.

5704 Beach Haven Road, East New Market

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

Selling Office: .

$930,000
3 Beds ⋅ 2 Baths
This is not just a waterfront property—it’s island living on the Chesapeake Bay, and it’s nearly impossible to find. With 800 feet of private shoreline, a 150-foot pier stretching into deep water with two boat lifts, electric, and water, and a rare private beach, this home delivers the ultimate coastal experience. Living on the Chesapeake Bay is incredible—but owning a property with its own beach is truly exceptional. Here, you can sink your toes into the sand just steps from your front door—or even land your own seaplane on the shoreline, as you can see in the listing photos—a luxury few will ever experience. Sitting on 2.38 acres at the tip of its own point of land, you get unmatched privacy, panoramic water views, and a level of seclusion rarely found. For the sportsman, it’s unbeatable—private hunting blind, co licensed (with only one neighbor) 900 feet offshore for winter waterfowl season, and deep-water access for boating and fishing. The seawall and riprap are valued at approximately $750,000, and the pier at $250,000, giving this property exceptional built-in value before you even step inside. The 3-bedroom, 2-bath home offers 1,650 square feet of bright, thoughtfully designed living space and is in excellent condition. The living room showcases breathtaking, panoramic views of the Chesapeake Bay and even has a wood-burning fireplace—perfect for a chilly fall or winter evening. Even the kitchen offers sweeping water views, making cooking a joy. The primary bedroom features its own private bathroom and direct bay views you can wake up to every morning. The floor plan is open and functional, perfect for everyday living and entertaining. This is a true four-season home, designed to be enjoyed all year long—fishing in the summer, hunting in the winter, and soaking in sunsets no matter the season. The backyard is graced with beautiful shade trees, offering the perfect spot to hang a hammock, sip your favorite drink, and lose yourself in your next great book. A two-car garage, outdoor shower, and all furnishings included make this home completely move-in ready. For investors, this property offers outstanding potential—projected at $75,000/year in short-term rental revenue with minimal upgrades, with management available at just 13% through Luke’s Vacation Rentals for an effortless income stream. Opportunities like this are extraordinarily rare. Schedule your private tour today and see for yourself what makes this Chesapeake Bay retreat truly one-of-a-kind.

2554 Hoopers Island Road, Fishing Creek

Listing courtesy of Keller Williams Flagship. Contact:

Selling Office: .

$900,000
3 Beds ⋅ 3 Baths
**Property Description: Waterfront Brick Rancher with Stunning Sunsets** Welcome to your dream waterfront retreat! This charming brick rancher features 3 spacious bedrooms and 2 full baths, perfect for a vacation rental or your forever home. As you step inside, you'll be greeted by stunning hardwood floors that flow throughout the home. The inviting living room boasts a brick wood-burning fireplace and picturesque views of Jenkins Creek, creating a cozy atmosphere for relaxation. Enjoy breathtaking sunsets from the comfort of your living space as the day winds down. The den, complete with built-in shelves, offers a great space for reading or a home office. Enjoy formal dining in the elegant dining room, which features sliding doors that lead to a screened porch, ideal for entertaining while overlooking the in-ground pool and the serene water views, perfect for sunset gatherings. The updated kitchen is a chef's delight, featuring laminate countertops, a large farm sink, an electric cooktop, a wall oven, a microwave, and a refrigerator with an ice maker. The generous walk-in pantry ensures ample storage space for all your culinary needs. Conveniently located, the laundry room includes a washer and dryer, a tub sink, and an additional toilet. The primary bedroom offers a tranquil view of the pool and creek, along with double cedar closets for all your storage needs. Its accompanying bath features ceramic tile flooring and a stall shower. Two additional bedrooms are well-appointed, one measuring 13’ x 11’ and the other 12’ x 11’, both with cedar closets for a touch of warmth and character. Step outside to the concrete patio that surrounds the in-ground pool and hot tub/spa, complete with a Sun Setter awning for shade on sunny days. For water enthusiasts, the property includes a pier with electric and water access, along with a boat lift and a jet ski lift, making it easy to enjoy life on the water. With gorgeous sunsets painting the sky every evening, this waterfront brick rancher offers the perfect blend of comfort, style, and outdoor adventure. Don’t miss your chance to own this incredible property!

2202 Jenkins Creek Road, Cambridge

Listing courtesy of McClain-Williamson Realty, LLC. Contact:

Selling Office: .

$850,000
EXCELLENT HUNTING FARM! 112 TOTAL ACRES, 35 TILLABLE ACRES, WITH AN OLD HOUSE, BARN, POND AND ONE NEWER METAL BARN, SEPTIC WAS PUT IN 2006. THIS FARM OFFERS EVERYTHING FROM TURKEYS, WHITETAIL, SIKA DEER, GEESE AND DUCKS. THE SOILS ARE HEAVY, HYDRIC SOILS WHICH ARE PERFECT FOR CREATING MORE WATERFOWL IMPOUNDMENTS AND WETLAND RESTORATION HABITAT WORK.

1829 Brannocks Neck Road, Cambridge

Listing courtesy of Meredith Fine Properties. Contact:

Selling Office: .

$825,000
Improved price!! Check out this chicken farm and shop ! Central location-Two chicken houses - growing for Amick. 60' x 500' houses. Updated and ready to go - Solar panels provide huge yearly savings to bottom line, and rebates at the end of the year. Shop is 50' x 72' with 36' x 40' addition offering many possibilities.

5405 Wesley Road, Hurlock

Listing courtesy of Coldwell Banker Realty. Contact:

Selling Office: .

$770,000
4 Beds ⋅ 3 Baths
Classic Historic Tidewater Colonial with 525+/- feet on the banks of Fishing Creek overlooking the Little Choptank River with a short ride to the Chesapeake Bay. Close to some of the best fishing spots on the Bay. This Historic Tidewater Colonial w/two bedrooms, living room, den, family room, dining room, kitchen, scenic three season porch, utility room, and two car garage make the Bay and its tributaries a wonderful playground for anyone interested in living on Maryland's Eastern Shore. The property also consists of a guest house with two bedrooms, bath, living room and workshop on the first floor with roll-up doors for easy access, as well as, along with a separate expansive two car garage with bathroom, office and Japanese cultural meditation room on the second floor. A separate Japanese tea room is available for those that want to embrace the Japanese culture. As you venture out to the waterfront, you will find a newly riprapped shoreline with lengthy pier with two boat lifts, and a protected boat basin for kayak and small boat launching. Come enjoy everything living on Maryland's Eastern Shore has to offer. Hot Tub Sold "As-Is". ****Property was staged for photos.***

1308 Town Point Road, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$751,000
5 Beds ⋅ 4 Baths
Welcome to your dream home! This stunning property combines everything you’ve ever wanted: a prime location, exceptional privacy, and unparalleled amenities that are sure to leave a lasting impression. Picture yourself in this spacious 5-bedroom, 4-bathroom home designed with an open floor plan, where the rear yard connects seamlessly with a partially fenced, multi-level outdoor haven. Imagine mornings spent by the inground pool, afternoons in the nearby pool house with its fully equipped kitchen and studio space, and evenings gathered around the cozy firepit with friends, laughter, and your favorite treats. Inside, the great room offers an elegant yet functional centerpiece with tray ceilings, custom cabinetry, and a gas fireplace that sets a warm, inviting tone. The thoughtfully planned kitchen features a central island with breakfast bar seating, quartz countertops, and top-of-the-line stainless steel appliances, including a Jenn-Air downdraft range, double wall ovens, and more. The barn-style door opens to an oversized walk-in pantry, delivering both charm and practicality. For hosting memorable meals, the adjacent dining room offers the perfect space. Relaxation reaches new heights in the primary suite, which has private deck access and plenty of room for a cozy sitting area. Its adjoining spa-like bathroom boasts dual vanities, a soaking tub, and a spacious walk-in closet. Secondary bedrooms offer both privacy and flexibility, with features like Jack & Jill baths and walk-in closets. A fourth bedroom serves as an ideal guest suite or office space, and upstairs you’ll find a fully finished second floor complete with a media room, game room, fifth bedroom, and a full bathroom. Let’s not forget the functional touches that make this property stand out: a spacious laundry room, a three-car garage, floored attic storage, and a separate outbuilding suitable for a business or hobby needs. Outside, a paved driveway doubles as a pickleball court, and an adjacent parking pad with electric hook-up for effortless RV or boat charging. Another substantial home improvement to note is the new roof which was installed in 2023 to both the main house and pool house. If luxury, space, and convenience top your wishlist, take action today—this home is ready to make your dreams a reality!

3536 Indian Grant Road, East New Market

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

Selling Office: .

$750,000
4 Beds ⋅ 4 Baths
Welcome to 5902 Heather Ln! This beautifully renovated home sits on 3.3 acres of peaceful land with a creek running behind the property. Every detail has been updated by the owner, giving you a truly move-in ready home with a modern touch. Featuring 4 spacious bedrooms and 4 full bathrooms, this home is perfect for families or those who love to entertain. The gourmet kitchen shines with brand-new finishes, while the open-concept living areas bring in plenty of natural light. Step outside to enjoy a beautiful wrap around deck and two private balconies, ideal for relaxing, hosting gatherings, or simply soaking in the views of your expansive property. deck offers the perfect space for gatherings, barbecues, or simply relaxing while enjoying nature. With over 3 acres to explore, you’ll have both privacy and space to create your dream lifestyle. Don’t miss this unique opportunity to own a fully updated home with the perfect blend of modern comfort and natural beauty!

5902 Heather Lane, Cambridge

Listing courtesy of Fairfax Realty Premier. Contact:

Selling Office: .

$700,000
6 Beds ⋅ 3 Baths
Welcome to Transquaking Lodge, a truly one-of-a-kind property nestled on the banks of the Transquaking River in Cambridge, Maryland, right next to the iconic Blackwater National Wildlife Refuge. Situated on 4 scenic acres, this fully renovated waterfront lodge offers unobstructed views and direct access to one of the most celebrated wilderness destinations in the United States, as recognized by National Geographic. With over 30,000 acres of protected lands at your doorstep, you’ll enjoy unmatched access to Fishing Bay and Blackwater without the burden of private refuge ownership. This rare waterfront location cannot be duplicated under today’s development regulations, making it an extraordinary find for outdoor enthusiasts, hunters, and conservation-minded investors. Step inside the expansive 6-bedroom, 3-bath lodge featuring 2,900± square feet of open-concept living space, plus an additional 2,900± square feet of climate-controlled lower-level storage. The heart of the home is a grand stone fireplace anchoring the spacious family room—perfect for gathering after a day in the field or on the water. The open kitchen and dining area create a warm, inviting atmosphere ideal for entertaining. Originally built in the 1950s, the home was structurally elevated over 6 feet in 2011 to accommodate waterfront conditions and future-proof the property. A comprehensive renovation in 2021–2022 brought modern upgrades including a new kitchen, bathrooms, HVAC systems, insulation, well and purification system, lighting, and more, while carefully preserving the lodge’s rustic character. Outdoors, your private boat ramp provides quick and easy access to world-class hunting and fishing. Dorchester County is home to the elusive Sika deer, diverse waterfowl, wild turkey, striped bass, snakeheads, and blue crabs, all thriving in this unique ecosystem. The lower-level offers over 2,900± square feet of concrete-floor, heated storage, perfect for boats, ATVs, kayaks, and gear. Most furnishings convey with the sale (excluding select family heirlooms, taxidermy and boats), making this a turnkey opportunity for a family retreat, hunting club, or income-generating rental. Don’t miss your chance to own this rare waterfront sanctuary on Maryland’s Eastern Shore.

3706 Bestpitch Ferry Road, Cambridge

Listing courtesy of The Land Group. Contact:

Selling Office: .

$700,000
3 Beds ⋅ 2 Baths
This property consist of approx. 20.52 AC. Mostly tillable. Lots of privately The home is an older Nanticoke Cape Cod style sold in AS IS Condition. This home is a three bedroom , two bath in need a a little TLC. Also has a Detached Garage/ Workshop

6422 Glen Oak Hotel Road, Hurlock

Listing courtesy of Brenton Realty Group. Contact:

Selling Office: .

$682,500
3 Beds ⋅ 3 Baths
Experience Timeless Waterfront Living on the Chesapeake Bay! Step into a serene retreat where panoramic Chesapeake Bay views and breathtaking sunsets become your daily backdrop. This meticulously crafted and updated 3-bedroom, 2.5-bath home seamlessly blends classic Eastern Shore charm with modern luxury.​ At the heart of the home lies a chef’s kitchen, adorned with top-of-the-line appliances, gleaming granite countertops, and rich cherry floors that exude warmth and sophistication. The waterside sunroom invites you to relax and soak in the ever-changing bay vistas, while the dedicated office and spacious walk-in pantry cater to both work and daily living needs. The primary suite offers a private sanctuary, complete with a luxurious bath designed for ultimate comfort.​ Enhancing the property's allure is a detached cottage, featuring a cozy fireplace and captivating water views—perfect for guests or a tranquil studio space. A private pier with lift extends your connection to the bay, ideal for boating enthusiasts or peaceful moments by the water.​ The property also includes a delightful garden shed, perfect for gardening enthusiasts or additional storage. Nestled in a historic Eastern Shore community, you're just moments away from the natural wonders of Blackwater National Wildlife Refuge, scenic biking trails, and the Harriet Tubman Underground Railroad National Historical Site. This home isn't just a residence; it's a step back in time, offering a harmonious blend of nature, history, and refined living.​

1226 Horse Point Road, Fishing Creek

Listing courtesy of Benson & Mangold, LLC. Contact:

Selling Office: .

$675,000
4 Beds ⋅ 2 Baths
Nestled on 2.38 scenic acres, this beautifully updated farmhouse blends timeless country charm with modern comfort. Offering 3,419 sq ft of living space, this spacious home features 4 bedrooms, 2 full baths, and generously sized rooms throughout. The heart of the home is the kitchen, complete with quartz countertops, abundant cabinetry, a large island bar, plantation shutters, and a cozy pellet stove — perfect for gathering and entertaining. The inviting living room adds even more warmth with an additional pellet stove and plenty of space to relax. Outdoor amenities are exceptional, including a welcoming front porch, brick walkways, side deck, covered entertainment area, blacktop circular driveway (recently sealed), and multiple outbuildings ideal for hobbyists, storage, or workshops. The impressive 50'x23' detached 4-car garage and 48'x24' pole barn with a 48'x14' lean-to and second floor provide endless possibilities. Major upgrades and improvements include HVAC, tankless water heater, roof, siding, flooring, bathrooms, side composite deck, encapsulated crawlspace with two sump pumps and French drainage system, sliding and French doors, fresh interior paint, and professional landscaping. This home is ideally located along the route of the seasonal Eagle and the Ironman Maryland triathlon events with convenient access to Public Boat Ramp, shopping, entertainment, grocery stores, fine dining and Blackwater National Wildlife Refuge, Enjoy peaceful country living with modern updates, ample space, and incredible versatility — this one truly has it all!

2010 Church Creek Road, Cambridge

Listing courtesy of Keller Williams Select Realtors of Cambridge. Contact:

Selling Office: .

$675,000
Upgraded three-house poultry farm in Dorchester County, Maryland, currently contracted with Allen Harim under a 7-week grow-out program. The farm is well maintained, compliant with integrator standards, and positioned for strong performance with recent capital improvements and incentive-eligible upgrades. The operation includes three 40’ x 500’ poultry houses built between 1987 and 1992 with an estimated capacity of approximately 65,217 birds per flock at 0.92 sq. ft. per bird, targeting 7.0 lb birds with a goal of roughly five flocks per year. The houses are exceptionally tight (wind speed rating: 815). Allen Harim’s tiered incentive pay structure is represented as a $0.0515/lb base rate with bonuses for tunnel ventilation (no doors) of $0.0055/lb, solid side walls of $0.0035/lb, tube heating of $0.0030/lb, new stir fans of $0.0010/lb, and new drinkers of $0.0010/lb, for a total represented pay rate of $0.0655/lb. Recent upgrades from 2020–2025 include, in 2024/2025, 33 new tunnel fans and three exhaust fans, new stir fans, a new waterline suspension system with drinker nipples (incentive eligible), new cool cell pads and waterlines, solid sidewalls, new metal siding and roofing, new insulation, vapor barrier, and interior plywood, new bi-fold end doors, LED lighting with dimmers, controller software upgrades, new feed bins, and updated pump room plumbing; in 2022, new feeders, augers, and motors; and in 2020, replacement of tunnel curtains. The farm is equipped with Choretronics 2 controllers, Choretime flood feeders, tube heating, tunnel curtains, two wells, and a 125 kW generator, and also includes a 40’ x 72’ manure shed with five composter bins plus a small air-conditioned office with a bathroom and pump tank. Perc approval was completed in 2017/2018. Included equipment includes a 2016 Kubota L3901 with a 5’ bush hog, box blade, tiller, and bucket, as well as a Kubota B8200 tractor. An expired septic permit is attached in the documents section; Dorchester County has indicated it can be renewed, however Buyer is responsible for performing their own due diligence regarding septic permitting and approvals. DO NOT ENTER FARM WITHOUT APPOINTMENT.

Beaver Neck Village Road, Cambridge

Listing courtesy of The Land Group. Contact:

Selling Office: .

$650,500
4 Beds ⋅ 3 Baths
Discover the ultimate Chesapeake Bay lifestyle with this exceptional fully furnished 4-bedroom, 2.5-bath waterfront retreat set on 3 private buildable acres on Hoopers Island. With breathtaking water views from every window, this property offers unmatched tranquility and endless potential. The home features a spacious first-level entertainment area with a ping pong/air hockey table and Dart room, a first floor bedroom with a large half bathroom, and also first floor laundry. Walk out to a large patio complete with a high end versatile carbon steel Arteflame grille which also converts to a fire pit, alongside of the patio is a separate crab cooking station—perfect for entertaining family and friends. The second level offers 3 bedrooms and 2 full bathrooms, a wraparound deck, a welcoming front porch, and a large open kitchen. Start your morning with coffee and a breathtaking sunrise over the Honga River from your front porch, then wind down in the evening with a delicious meal from your premium grill while savoring spectacular sunsets over Back Creek from the expansive rear deck. The home comes fully furnished, allowing you to enjoy the home on day one! Launch your next fishing or crabbing adventure and cast a line from your private 80 foot pier and reel in rockfish, flounder, trout, or even skate—or drop a trap for a crab feast! On days you do not want to enjoy your own fishing or crabbing, take a quick walk along your 350 feet of beautiful shoreline to the oyster aquaculture and crabbing/fishing company, and pick up some fresh oysters, fish or crabs, giving you an authentic Eastern Shore experience right at your doorstep. On your expansive lot, you'll be treated to frequent visits from bald eagles, ospreys, blue herons, egrets, woodpeckers, and an abundance of other incredible wildlife. Additional highlights include a 1-car garage, a dumbwaiter (lift) for easy transport of groceries and gear, a shed with electric and its own deck, a BAT (Best Available Technology) septic system, energy-efficient LED lighting throughout, and high-speed fiber internet for seamless connectivity. The lot is also buildable, offering the opportunity to expand or add a second home. Whether you're looking for a private vacation retreat, a full-time residence, or a property with incredible Airbnb potential, this unique home offers endless possibilities in a truly spectacular setting.

2508 Old House Point Road, Fishing Creek

Listing courtesy of EXIT On The Harbor Realty. Contact:

Selling Office: .