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$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:

$300,000
4 Beds ⋅ 4 Baths
Welcome to the home where modern design meets charm- right in the heart of Hurlock. The main floor features a kitchen, dining room, living room, a family room, a bathroom and a bedroom. The top floor features two en-suites and an additional bedroom! The mostly-finished basement features an office, a bonus room, a full bathroom, living room and a kitchen! The basement has direct outdoor access, as well as interior access, facilitating privacy and/or creating separate quarters. This home is perfect for multi-generational living! The current owner has significantly renovated the home in the last few years and simply needs a few finishing touches.

307 S Main St, Hurlock

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

$160,000
4 Beds ⋅ 2 Baths
**RECENTLY REDUCED – INVESTOR & RENOVATION OPPORTUNITY!** Bring your vision and finish what has already been started in the heart of Cambridge. With a portion of the renovation work already underway, this property offers an appealing opportunity for investors, flippers, landlords, or buyers looking to build equity through improvements. Recent updates include luxury vinyl plank flooring throughout much of the home and a nearly finished upper level offering flexible space for two bedrooms, or a bedroom with adjoining office/bonus area, plus a half bath and additional closet space. The main level features two bedrooms, living room, laundry area, and a kitchen space ready for renovation. Significant improvements are still needed, including completion of the kitchen and installation of a heat source; natural gas is available. For the right buyer, this is an opportunity to complete the remaining work, add value, and reposition the property for resale, rental income, or personal use. Outside, the property offers a fenced backyard, concrete patio, storage shed, off-street parking, and front porch. Conveniently located just off Race Street and within walking distance of downtown Cambridge, restaurants, shopping, and the waterfront. **Being sold strictly AS-IS. Seller is motivated and ready to make a deal—bring your contractor, your vision, and your offer!** Renovation financing, including FHA 203(k), may be an option for qualified buyers. **Some photos have been virtually staged or virtually enhanced to illustrate the property's potential.**

904 Central, Cambridge

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

$169,900
3 Beds ⋅ 1 Baths
3 bedroom 1 bath home in Sandy Hill area. Home is being sold "AS IS", cash or conventional financing offers only.

200 Wisteria Dr, Cambridge

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

$274,900
4 Beds ⋅ 3 Baths

219 Willis St, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$119,900
3 Beds ⋅ 1 Baths
Set just outside of town, this rancher home is situated on .47 acres on cul-de-sac street. The simple single level living features 3 bedrooms, 1 bath with a semi-open floor plan. It is ready for your personal touches.

4808 Webster St, Federalsburg

Listing courtesy of Century 21 Harbor Realty. Contact: 4105482100
$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
$580,000
5 Beds ⋅ 4 Baths
This is a beautifully updated and well-maintained Four Square located in Cambridge's Historic District. It is a grand house for entertaining both inside and out. In addition to the 5 bedrooms and 3.5 baths in the Manor House, the property boasts 2 additional buildings on the .57 acre lot filled with specimen flowers, shrubs and trees. 1 building, originally built as a Montessori school, is well suited as a studio, in-law suite, professional office space or Man cave. It is currently registered and generating income as an Airbnb.

309 Glenburn Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425
$335,000
2 Beds ⋅ 1 Baths
2 houses and 1 mobile home on 6 acres with separate septic systems, and shared well. all three units tenant occupied with potential for rent increase. property can be subdivided in 3 , two acre parcels. sewage reserve areas are platted and approved. houses are certified lead free and mobile home was built in 1980's.

5987,5989,5991 Route 14, East New Market

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$334,900
4 Beds ⋅ 3 Baths
Beautifully maintained and move-in ready 4BR/2.5BA Colonial located in the quiet community of Longboat Estates. From the moment you arrive, you’ll appreciate the curb appeal, double-wide driveway, attached two-car garage, and welcoming front entry. Inside, this home offers a bright and airy open floor plan filled with natural light, recessed lighting, and comfortable living spaces throughout. The main level features a spacious living room, convenient half bath, and an open-concept family room, dining area, and kitchen designed for both everyday living and entertaining. The kitchen boasts granite countertops, ample cabinetry, a pantry closet, black and black stainless appliances, and a double stainless sink overlooking the backyard. Sliding doors off the dining area lead to a large Azek deck with peaceful views. Upstairs, you’ll find three generously sized secondary bedrooms, a full hall bath with a linen closet, a convenient second-floor laundry room, and a spacious primary suite. The primary bedroom features a walk-in closet and private en-suite bath with a double vanity and walk-in tile shower with bench seating. The backyard provides plenty of room to relax, entertain, or enjoy the surrounding green space. Conveniently located near shopping, restaurants, and commuter routes, residents also enjoy access to the community pool and dock.

146 Regulator Dr N, Cambridge

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$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:

$443,000
3 Beds ⋅ 3 Baths
Charming two-story home located in Cambridge’s desirable West End area, offering classic character and exceptional upkeep. Built in 1920, this single-family residence features approximately 1,738± square feet of living space on a spacious 0.26± acre lot. The home includes 3 bedrooms and 2 full bathrooms, with a functional layout and original elements that add to its historic appeal and traditional construction details. This property has been incredibly well maintained, with numerous upgrades completed over the years, providing peace of mind while preserving its timeless charm. The exterior features a 24' x 28' detached two-car garage, complete with an electric vehicle charging hookup, offering both convenience and modern functionality. Situated just minutes from downtown Cambridge, shopping, dining, and waterfront attractions, the location provides both convenience and access to everything Maryland’s Eastern Shore has to offer. Whether you're searching for a primary residence or investment opportunity, this property delivers in a sought-after area.

116 Glenburn Ave, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$450,000
5 Beds ⋅ 3 Baths
***Sellers have found home of choice and are ready to entertain your offer!***Grand and beautifully updated, this circa‑1900 residence offers timeless architectural charm on 1.67 acres of land just moments from downtown and the waterfront. A welcoming wrap‑around porch with ceiling fans, sets the tone, perfect for relaxing and entertaining. The expansive grounds-fenced on three sides-include a spacious three story barn/garage, offering exceptional versatility and opportunity. Enjoy the lovely flagstone patio with fire pit and charming gazebo—ideal for outdoor gatherings and peaceful retreats. Step inside where historic character blends seamlessly with thoughtful updates, preserving the elegance of a bygone era while offering modern comfort and functionality. Generous living spaces, high ceilings, and period details reflect the home’s original craftsmanship, enhanced by tasteful improvements throughout. The generously sized first floor primary suite includes the ideal space for adding an en suite bath, offering flexibility to tailor the home to modern living. Climb the grand staircase to the second level with four spacious bedrooms and a full bath. The third level of the home includes a full bath, with space that could accommodate a sixth bedroom with minimal work. Rarely does a property of this size, stature, and amenity become available so close to shops, dining, and waterfront attractions. A truly special opportunity to own a distinctive piece of history in a prime location.

1311 Race St, Cambridge

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

$299,000
3 Beds ⋅ 3 Baths
This beautifully crafted new construction home in Vienna MD, ideally located just blocks from the Nanticoke river waterfront. Nestled in one of the Eastern Shore's hidden gems, this home offers the perfect balance. Centrally located between Maryland's beaches and the Chesapeake Bay, making it an ideal full time residence, second home or investment property. This thoughtfully designed home features 3 bedrooms and 2.5 bathrooms offering modern comfort with timeless appeal. Step inside to find Luxury Vinyl Plank through out the entire home, providing durability, style and low maintenance living. The heart of the home is the open concept kitchen complete with stainless steel appliances ample cabinetry and a layout perfect for entertaining or everyday living. The open flow between the kitchen, dining and living areas creates a bright and welcoming space. Upstairs, the primary suite offers a private retreat and two additional bedrooms provide flexibility for guest family or home office Enjoy life just minutes from Vienna's waterfront park, public boat ramp and scenic Nanticoke River access, with the addend charm of the summer outdoor concerts on the waterfront and community events that make this small town so special. Whether you're looking for boating, fishing or peaceful eastern shore living. HOME IS NOT COMPLETED YET, CITY WILL BE COMPLETING THE SIDEWALK AND A DRIVE WAY WILL BE INSTALLED BY THE BUILDER. YARD WILL BE GRADED AND GRASS PLANTED

302 Church St, Vienna

Listing courtesy of ERA Martin Associates. Contact: 4107491818
$684,900
4 Beds ⋅ 2 Baths
Enjoy waterfront living in this updated 4 bedroom, 2 bath waterfront home with stunning sunrise and sunset views over the Honga River and Chesapeake Bay. Bright and inviting with comfortable living spaces, cathedral ceilings, this home is ideal as a full-time residence, weekend retreat or airbnb investment. The property features a large pole barn with electric and heating & air, shed, large deck and spacious outdoor landing with fire pit overlooking breathtaking Chesapeake Bay views. Located just across from a marina and public boat ramp, you’ll have easy access to boating, fishing and crabbing. Newer well and septic plus a fully riprapped shoreline. Bring your golf cart, kayaks and bikes and enjoy all that Hoopers Island has to offer. Nearby favorites include Old Salty’s Restaurant and Hooper’s Island General Store.

1750 Hoopersville, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$1,399,999
5 Beds ⋅ 3 Baths
Endless westerly vistas stretch across Madison Bay, delivering breathtaking sunsets that feel like a private showing each and every evening. This is more than a home—it’s a waterfront sanctuary designed for those who expect their lifestyle to be as elevated as their surroundings. Welcome to Saltmarsh, an extraordinary 8.5-acre estate where luxury, privacy, and coastal beauty converge. With 5 bedrooms (plus a bonus room that could be considered a 6th) and 3 full bathrooms, this property effortlessly transitions between an exceptional full-time residence and the ultimate weekend retreat for unforgettable gatherings with friends and family. Spanning over 5,000 square feet, the home is thoughtfully designed to maximize both space and scenery, with walls of windows that flood the interior with natural light and showcase those sweeping bay views from nearly every room. The main level is nothing short of an entertainer’s masterpiece—an open-concept layout anchored by a stunning great room, seamlessly flowing into a chef’s gourmet kitchen and sun-drenched sunroom on one side, while the opposite wing reveals a full-scale game room complete with a pool table and custom bar built for hosting on any scale. Step outside and the experience only gets better. Multiple expansive decks offer the perfect setting for everything from quiet mornings to lively evenings, all framed by panoramic water views. At the private dock, every detail has been accounted for—featuring water and electric, two jet ski lifts, and a 10,000-pound boat lift—creating a true waterfront playground. The oversized 3-bay garage provides ample space for all your water toys, equipment, and more—because a property like this is meant to be enjoyed without compromise. Offered fully furnished, Saltmarsh is completely turnkey—allowing you to step right into an effortless, elevated coastal lifestyle from day one. This is not just a home—it’s a statement.

4808 Saltmarsh Rd, Madison

Listing courtesy of Coldwell Banker Realty. Contact: 4105246111
$259,000
3 Beds ⋅ 2 Baths
Welcome to 12 Oak Street, where quality renovations and modern updates come together to create a home that’s ready to enjoy from day one. This beautifully renovated 3-bedroom, 2-bath home offers nearly 1,300 square feet of comfortable living space featuring an open, bright layout with abundant natural light, luxury vinyl plank flooring, fresh paint, and stylish finishes throughout. The completely updated kitchen features new cabinetry, countertops, stainless steel appliances, and a functional layout that flows seamlessly into the living and dining areas—perfect for everyday living or entertaining. Both bathrooms have been tastefully remodeled with clean, timeless finishes, while major improvements throughout the home provide peace of mind for years to come. Outside, you’ll enjoy a brand-new asphalt driveway, a spacious rear deck, and a generously sized backyard with room to entertain, garden, play, or simply relax. Conveniently located near downtown Cambridge, shopping, restaurants, parks, schools, and the waterfront, this home combines modern updates with everyday convenience. Move in, unpack, and start enjoying your new home. Schedule your private showing today.

12 Oak St, Cambridge

Listing courtesy of Keller Williams Select Realtors of Annapolis. Contact: 4109724000
$399,500
3 Beds ⋅ 2 Baths
This charming, move-in ready pondside retreat has everything you love about a peaceful vacation spot - and all the conveniences and comforts of home. Imagine sipping your coffee on the screened porch overlooking the pond, watching the songbirds migrate from your kitchen table, and being lulled by the rain on the metal roof. Not to mention a primary bedroom with en-suite bathroom, ample storage space (5 closets!), an enclosed front porch turned great room, and an eat-in kitchen with a pass through to the dining room. As the third owner of this beautiful log cabin, you benefit from the thoughtful details and loving upgrades over the years - some practical, some beautiful, and some both! Enjoy the fireplace hand-built from the foundation of a nearby farmhouse by a master mason; the soft cork floors in the kitchen that are soft on your joints and will never break a glass; to the solid brass doorknobs that ground you every day. The house features wood and gas fireplaces, convection stove, micro-filter heater, washer/dryer that feeds a sustainable grey water system, and even a generator that can fully power heat and electrical just in case. On a generous double lot, the property is edged by the Galestown Mill Pond, and includes a small dock and shoreline boat storage as well as two freestanding sheds. The front yard features native pollinator plantings, and the adjoined lot includes a small fruit orchard with apple, peach, and plum trees. The backyard is fully fenced in, offering privacy and safety. The garage includes an art studio with heart pine floors, a workshop space, and same-level laundry.

5610 Galestown Newhart Mill Rd, Galestown

Listing courtesy of CALLAWAY FARNELL AND MOORE. Contact: 3026294514
$293,500
3 Beds ⋅ 2 Baths
Charming and thoughtfully updated, this move-in ready 3BR/2BA water-view farmhouse is ideally situated on a quiet street in the Cambridge Historic District. A welcoming covered front porch leads into a bright entry and dining space, with classic pocket doors opening to the living room. The kitchen is well-appointed with wood cabinetry, crown molding, granite countertops, and stainless steel appliances. A full bath with a walk-in shower and timeless black-and-white tile completes the main level. Upstairs, you’ll find two generously sized bedrooms and a spacious primary suite. The outdoor space offers a private, garden-style setting with a patio, tiered beds, a shed with electric, and an enclosed porch. Recent upgrades, including HVAC and a tankless hot water heater, provide added comfort and efficiency.

105 West End Ave, Cambridge

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$249,999
3 Beds ⋅ 3 Baths
Nearly one acre of waterfront-adjacent land on the Little Blackwater River — with federally protected land as your permanent rear boundary and Blackwater National Wildlife Refuge just minutes down the road. This is a builder's opportunity. The existing structure is a tear-down, priced accordingly. What you're buying is the lot — a private, river-backing acre in one of the most scenic corridors on Maryland's Eastern Shore, surrounded by open fields and protected land on three sides with one neighboring property to the east. The location speaks for itself. Egypt Road is the primary access route into Blackwater NWR, one of the most visited natural destinations on the East Coast. Serious nature tourism, hunting, fishing, kayaking, and wildlife photography draw visitors to this corridor year-round. For an investor or developer with vision, the demand is already here. Custom retreat. Private residence. Nature-focused short-term rental. The use case is yours to define. Priced at $275,000. Contact us today to schedule a showing.

4731 Egypt Rd, Cambridge

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$599,900
5 Beds ⋅ 3 Baths
Completely renovated from top to bottom, this exceptional property offers a rare opportunity to enjoy the Eastern Shore lifestyle with the privacy, acreage, and storage many waterfront buyers are seeking—without the waterfront maintenance. Situated on nearly 7 secluded acres in the highly sought-after Neck District of Dorchester County, this property is just minutes from both the public boat ramp in Cambridge and Ragged Point Marina, providing convenient access to some of the region's best boating, fishing, crabbing, and watersports opportunities. A brand-new architectural shingle roof and thoughtfully redesigned open floor plan create a stunning great room where the kitchen, living, and dining areas flow seamlessly together—ideal for everyday living and entertaining. The beautifully updated kitchen features new countertops, ceramic tile backsplash, and all-new appliances, while updated bathrooms, flooring, wiring, lighting fixtures, and fresh landscaping ensure a truly move-in ready experience. The first floor offers two bedrooms and one full bath. Upstairs, the spacious primary suite includes a private bath and walk-in closet, along with two additional bedrooms and another full bathroom. Outside, the property transforms into a private retreat. Enjoy peaceful views of the pond from the expansive rear deck, gather with friends and family under the stars, or simply relax and take in the sights and sounds of nature. Surrounded by mature woods and abundant wildlife, including deer and turkey, the setting offers exceptional privacy and tranquility. For boating enthusiasts, the impressive 45' x 30' metal outbuilding with concrete floor provides ample room for boats, jet skis, trailers, recreational equipment, workshop space, or a home-based business. Whether you're returning from a day on the water or enjoying the serenity of your own acreage, this property delivers the best of both worlds. Located less than 10 minutes from Cambridge, this is a rare opportunity to own a fully renovated home that combines modern comfort, exceptional privacy, abundant storage, and easy access to the waterways that make the Eastern Shore such a special place to call home.

5951 Ross Neck Rd, Cambridge

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

$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
$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:

$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:

$425,000
3 Beds ⋅ 2 Baths
Welcome to 102 Choptank Avenue! Seller is generously offering $5,000.00 in a seller contribution toward closing costs. This quintessential 1918 house has been completely updated and currently showcases the best of the past and the present. Located just steps from the beautiful Choptank River, this house has multiple decks and a charming wrap-around porch affording glorious views of the Choptank! There are water views from virtually every room in the house. The house has been masterfully upgraded from top to bottom. The roof, heating systems, baths and kitchen have all been upgraded. The siding is new, the hot water on demand is new, the windows are new! The floors are beautiful and the porches and decks are lovely! The third floor has been completely insulated and serves as a storage area now but could definitely be finished off to provide more living space if so desired. Please come take a look! Sited within the charming historic district and just a block from the water, this lovely house is located just a few blocks from the iconic yacht club, the lighthouse and the vibrant downtown, which offers fun bars, restaurants and shops. Cambridge is alive and flourishing! Please call me for details!

102 Choptank Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425
$249,000
2 Beds ⋅ 1 Baths
Welcome to 408 Bayly Avenue! This is an absolutely charming cottage sited on a magnificent lot. The living spaces are generously sized, lovely and full of great natural light. The 2 bedrooms are separated by a hall bath. Beautiful hardwood floors have been run throughout the entire house. The Dining Room is located just off the kitchen and features a large window that captures the backyard vistas. The kitchen is large, well laid out and enhanced with sparkling appliances. The laundry is conveniently located off the kitchen with direct access to the incredible back yard. There is a wonderful front porch for watching the world pass by if one is so inclined. There is also an awesome covered porch in the back, overlooking a beautiful tranquil park-like setting. There is a plethora of places throughout the house and the yard that offer great choices for entertaining, seclusion, reading or working. Parking for 2-3 cars is easily accommodated in the driveway to the left of the house. Bayly Avenue is a well-loved quiet family street located just blocks from the bustling downtown and the magnificent harbour.

408 Bayly Ave, Cambridge

Listing courtesy of Compass. Contact: (410) 429-7425
$325,000
4 Beds ⋅ 3 Baths
Nestled within the prestigious High Street subdivision, this exquisite Colonial-style residence offers a seamless blend of luxury, comfort, and timeless elegance, perfect for those seeking an elevated lifestyle. Built in 2006, this detached home is equipped with an energy-efficient solar panel system that not only delivers long-term savings but also supports a sustainable way of living. At a generous 1,872 square feet, the home features four spacious bedrooms and two-and-a-half elegantly appointed bathrooms, all thoughtfully designed to maximize comfort and functionality. As you arrive, the home’s classic Colonial architecture, accented by charming vinyl siding and meticulously landscaped grounds, creates an inviting first impression. A beautifully crafted deck extends your living space outdoors, providing the perfect setting for entertaining guests or unwinding beneath the stars. Imagine sipping your morning coffee as you overlook the tranquil pond right in your backyard, a picturesque view that enhances the natural serenity of this remarkable property. Inside, you’ll find a warm and welcoming atmosphere anchored by a cozy fireplace in the heart of the living area, ideal for relaxing evenings or gatherings with family and friends. The attached front-entry garage adds convenience and ample storage, while additional driveway and off-street parking make hosting guests effortless. Situated on a 0.25-acre lot, the property offers plenty of room for outdoor activities and enjoyment. The homes scenic pond offers a peaceful and refreshing retreat. You will appreciate the area’s opportunities for walking, exploring, and unwinding amidst natural beauty. Additional upgrades include a newer HVAC system and sump pump, both just three years old, ensuring comfort and peace of mind. More than just a home, this property represents a refined lifestyle, where luxury, comfort, and nature coexist in perfect harmony. Whether you’re entertaining guests or enjoying quiet evenings at home, this Colonial gem invites you to experience everyday living at its finest. Don’t miss your chance to make this stunning property your own.

1012 Miles Ave, Cambridge

Listing courtesy of The Property Shoppe, LLC. Contact: 4432259975
$99,000
3 Beds ⋅ 2 Baths
Attention Investors & Renovators! Unlock the potential of this two-level home ready for your vision and finishing touches. Renovations have already been started, providing a great head start for your next project. With an estimated After Repair Value (ARV) of $225,000, this property offers an excellent opportunity for a profitable flip or a long-term rental investment. The main level features a full bath and a versatile bonus room that could serve as a home office, den, family room, or even a potential fourth bedroom. Upstairs, you'll find three bedrooms, a spacious full bath, and a wide hallway that enhances the home's open feel. The generous backyard offers plenty of space for outdoor entertaining, future expansion, or additional improvements. Add a privacy fence to create a feel of seclusion and outdoor retreat to maximize the property's appeal. Conveniently located near a public park, schools, restaurants, a deli, and grocery shopping, this home combines investment potential with everyday convenience. Whether you're searching for your next renovation project, a fix-and-flip opportunity, or a property to build long-term equity, this home offers exceptional possibilities. Bring your creativity and transform this property into something truly special. Don't miss this outstanding opportunity to add value and make it shine!

212 Main Street S, Hurlock

Listing courtesy of Keller Williams Select Realtors of Cambridge. Contact: 4102711265
$950,000
3 Beds ⋅ 1 Baths
Attention Investors! Don't miss this rare opportunity to acquire four single- family homes being sold as a package. each home features: 3 Bedrooms 1 bathroom with a eat in Kitchen. Approximately 800 Sq ft of living space. currently have all four with tenants. Situated on a combine 17,000 sq ft lot, Listed for 950,000

509 Edgewood Ave, Cambridge

Listing courtesy of New Realty, LLC. Contact: 4433246001
$469,990
3 Beds ⋅ 3 Baths
*OFFERING UP TO 15K IN CLOSING COST ASSISTANCE WITH USE OF APPROVED LENDER AND TITLE** Offering unique floor plans with scenic wooded, creek, and golf course views, Tides at River Marsh is the perfect place to call home. The St. Kitts offers single level living with 3 bedrooms and 2.5 baths on main level or choose the optional loft on the second floor and optional third bath. *Photos may not be of actual home. Photos may be of similar home/floorplan if home is under construction or if this is a base price listing.

TBB Marsh Elder Rd Unit #ST.KITTS, Cambridge

Listing courtesy of DRB Group Realty, LLC. Contact: 2404579391