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$8,950,000
24 Beds ⋅ 13 Baths
Parsons Creek Farm - A 255+/- Acre, Multi-Residence, Deep-Water, Waterfowl & Wildlife Estate at the Confluence of Parsons Creek and the Little Choptank River This once-in-a-lifetime Chesapeake Bay legacy holding is set upon 255.47 extraordinary acres of waterfront, wetlands, upland forest, and meticulously curated wildlife habitat making Parsons Creek Farm one of the most sophisticated private estates on Maryland's Eastern Shore. Masterfully blending historic charm, modern craftsmanship, high-performance land management, and recreational luxury, this turnkey, multi-residence compound stands unrivaled in scale, ecological design, and architectural execution. Positioned at the union of Parsons Creek and the Little Choptank River, the property enjoys nearly a mile of sandy, private shoreline, deep-water access, expansive water vistas, and complete seclusion - yet remains within a short drive to Cambridge, Annapolis, Baltimore, Washington, and the greater Mid-Atlantic corridor. A series of thoughtfully positioned structures - each with its own architectural identity - combine to create a private compound capable of sleeping more than 24 guests in total comfort. Elegantly sited to capture uninterrupted views across impoundments, woodlands, and water, the primary residence blends historic Maryland character with refined luxury. This meticulously designed, 9,583 sq. ft. luxury residence boasts an impressive array of distinct living areas, creating a home of both grand scale and exceptional comfort for family living and entertaining. The expansive property also features a charming, fully renovated, private 1,500 sq. ft. Cape Cod–style guest house that extends a warm welcome to visitors, and a third two-story residence complete with a full bedroom suite, full bathroom, laundry, and sweeping picture windows overlooking one of the ponds. Part of the estate's recreational opportunities is an over-the-water bar and game room, a gathering place where family and friends can cast a line into the pond while enjoying the comforts of a private lounge. Equestrian enthusiasts and entertainers alike will appreciate the impressive stable complex, complete with second-floor luxurious living quarters, a spacious game room, and full bar. Balconies at each end capture sweeping views of the surrounding woodland and water, creating an atmosphere of timeless elegance. Whether envisioned as a generational family compound, a private sporting estate, a conservation-forward investment property, or an exclusive corporate/hospitality retreat, Parsons Creek Farm offers a combination of luxury, ecological engineering, and rural waterfront beauty unmatched anywhere in the Mid-Atlantic. This remarkable waterfront estate is a unique opportunity that unites world-class waterfowl and upland hunting, meticulous wildlife management, and refined living—enhanced by impressive income potential. Having identified his replacement property, the seller is prepared to move forward and welcomes qualified offers.

964 Taylors Island Rd, Madison

Listing courtesy of National Land Realty, LLC. Contact: 4434128971
$320,000
3 Beds ⋅ 2 Baths
$10,000 Price Reduction – Rare Chesapeake Bay Waterfront Opportunity! Waterfront homes under $325,000 are becoming increasingly difficult to find, making this well-maintained island retreat an exceptional value. Enjoy sweeping western views across the Chesapeake Bay, spectacular sunsets, and the peaceful waterfront lifestyle you've been dreaming of. Ideal as a full-time residence, weekend getaway, or investment property, the home features an updated kitchen with a center island, gas range, coffee bar, and luxury vinyl plank flooring. Flexible living spaces include a first-floor bedroom and office/playroom, an updated bath, a spacious family room, and a private second-floor owner's suite. Additional highlights include ductless mini-split heating and cooling, hot water baseboard heat, high-speed internet availability, rip-rapped shoreline, and a BAT septic system installed in 2019. A county-owned public boat ramp is just down the street beside a privately owned marina where slips may be available for rent (buyer to verify). A brand-new survey and legal description are available upon request. With a $10,000 price reduction, this is one of the best opportunities to own Chesapeake Bay waterfront without the premium price tag.

1814 Hoopersville Rd, Fishing Creek

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

$395,000
4 Beds ⋅ 3 Baths
Built just one year ago and barely lived in, this spacious 4-bedroom, 2.5-bath home in Longboat Estates offers modern comfort and an unbeatable Eastern Shore lifestyle. The open-concept floor plan features luxury vinyl plank flooring, a beautifully appointed kitchen with granite countertops, stainless steel appliances, and a large center island, all flowing into a bright family room with a gas fireplace. Upstairs, the spacious primary suite includes a walk-in closet and private en-suite bath with dual vanities and an oversized tiled shower. An attached two-car garage, generous living spaces, and a private backyard backing to trees complete the package. Enjoy access to community amenities including a pool, boat ramp, and dock. Conveniently located just minutes from downtown Cambridge, waterfront dining, marinas, the Choptank River, Blackwater National Wildlife Refuge, and the Harriet Tubman Underground Railroad Visitor Center. Enjoy the benefits of nearly new construction without the wait!

178 Regulator Dr N, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$229,000
2 Beds ⋅ 1 Baths
Move right into this charming, turn-key bungalow! Freshly painted inside and out with gleaming hardwood floors, this home is completely ready for its next owner. Beyond the beautiful main living area, walk-up stairs lead to a fully floored attic offering incredible potential to add two additional bedrooms and a full bath. Outside, enjoy a massive yard complete with a garden shed and a concrete driveway with ample parking for three cars. This is a rare opportunity to enjoy a move-in-ready home today while easily adding living space and lasting equity tomorrow

406 Shepherd Ave, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$189,500
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 offers a working well and newer 4 chamber septic system, adding value and future potential. 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
$294,900
4 Beds ⋅ 2 Baths
Priced to move! Welcome home to this charming, move-in-ready retreat packed with updates and space to enjoy indoor and outdoor living. Recent improvements include a new roof, siding, dual HVAC systems for efficient comfort upstairs and down, and more! This well-maintained 4-bedroom, 2-bath split-foyer sits on a generous corner lot of over half an acre, offering the rare bonus of no city taxes while still enjoying public water and sewer. Step outside to an elevated deck perfect for entertaining, along with expansive front and rear yards ideal for relaxing, playing, or hosting gatherings. Inside, you’ll find two spacious family rooms—one on each level—providing flexibility for living, working, or entertaining. Garden and outdoor enthusiasts will love the included raised beds, drip-irrigation system, and two storage sheds, making it easy to cultivate your own seasonal oasis. Nestled in a peaceful setting just outside city limits, this home offers the best of both worlds: quiet living with convenient access to downtown Cambridge, nearby parks, and boat ramps. With its inviting curb appeal and thoughtful updates throughout, this property is ready to welcome you home!

9 Merryweather Dr, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$449,900
4 Beds ⋅ 3 Baths
Experience the best of Eastern Shore living at 419 Osprey Circle, a spacious and beautifully appointed home offering over 3,400 square feet of thoughtfully designed living space in one of Cambridge's most desirable neighborhoods. Combining generous room sizes, flexible living areas, and an exceptional location just minutes from the waterfront, this home delivers the perfect blend of comfort, convenience, and lifestyle. Step inside to discover a dramatic two-story family room filled with natural light that serves as the heart of the home. The open and inviting floor plan offers plenty of space for both everyday living and entertaining, while a dedicated main-level office or den provides the perfect setting for remote work, studying, or a private retreat. The upper level is highlighted by an impressive luxury primary suite designed to be your own private sanctuary. This expansive retreat features a large bedroom, a separate sitting area, a stunning fully renovated spa-inspired bathroom, and a custom walk-in closet that offers both beauty and exceptional storage. Also located upstairs is a spacious loft or den overlooking the two-story family room below, creating additional living space that could easily be converted into a fourth bedroom if desired. Outside, the property offers a generous yard with plenty of room to relax, entertain, garden, or simply enjoy the peaceful surroundings. Located just minutes from historic downtown Cambridge and the scenic shores of the Choptank River, residents enjoy easy access to waterfront dining, marinas, parks, shopping, and year-round outdoor recreation. Cambridge has become one of Maryland's most sought-after waterfront communities, known for its vibrant downtown, rich maritime heritage, boating, fishing, kayaking, paddleboarding, and proximity to the renowned Blackwater National Wildlife Refuge. The area is also home to the internationally recognized IRONMAN Maryland and Eagleman 70.3 triathlons, which attract athletes and visitors from around the world each year. These iconic events showcase Cambridge's stunning waterfront setting, scenic country roads, and active outdoor lifestyle, adding to the energy and appeal of this unique community. Whether you're enjoying a day on the water, exploring local restaurants and shops, or simply relaxing in your spacious home, 419 Osprey Circle offers an opportunity to embrace the lifestyle that makes Maryland's Eastern Shore such a special place to live. Conveniently located within easy reach of Annapolis, the Delaware and Maryland beaches, and the Washington-Baltimore metropolitan area, this exceptional property is ready to welcome you home.

419 Osprey Cir, Cambridge

Listing courtesy of RLAH @properties. Contact:

$295,000
3 Beds ⋅ 1 Baths
Escape to the peace and privacy of Maryland's Eastern Shore with this charming ranch-style home situated on approximately 2 acres. Offering comfortable one-level living, this well-maintained property features 3 bedrooms, 1 full bath, and a spacious layout designed for everyday living. Inside, you'll find a thoughtfully updated interior with modern touches while maintaining the home's warmth and character. Recent improvements include a newer roof and siding, providing added value and peace of mind. Outside, the oversized detached 2-car garage offers endless possibilities for vehicle storage, hobbies, a workshop, or recreational equipment. The expansive lot provides plenty of room for gardening, outdoor entertaining, pets, and enjoying the surrounding countryside. With no HOA restrictions, ample parking, and room for boats, RVs, trailers, or additional outdoor toys, this property offers the freedom and flexibility many buyers are seeking. Conveniently located near Cambridge and Route 50, you'll enjoy easy access to shopping, dining, healthcare, and all the recreation the Chesapeake Bay region has to offer. Whether you're looking for a full-time residence, a weekend retreat, or a property with space to spread out and enjoy country living, this Eastern Shore gem is ready to welcome you home.

3714 Hicksburg Rd, East New Market

Listing courtesy of Douglas Realty LLC. Contact: (410) 255-3690
$895,000
4 Beds ⋅ 3 Baths
Welcome to 6011 Sunnyside Court...a true destination! This waterfront sanctuary has been completely refreshed with fabulous interior paint and a brand new 30 year roof! It is complimented by a sparkling saltwater pool and wide-open views of the Warwick River -your own resort! Moreover, this property provides great supplemental income for the astute investor. Enjoy the river-front complex when time allows yet rent "the resort" easily while you are otherwise engaged. This listing is unique in that it is sited on land that provides great views of the river which makes it a very popular airbnb property yet no flood insurance is required. It was designed with generously-sized rooms, a beautiful pool side leisure area and ample gardens. In sum, it is a splendidly built, upscale oasis in East New Market. The house is perfectly sited on a spacious 1.2 acre parcel in which to enjoy all seasons. This stylish hide-a-way has it all. Five bedrooms, upscale finishes and room to play. The first floor is fantastic with a wide open floor plan, 2 full bedrooms, a powder room, covered porch and views galore! A gracious living room has French doors overlooking and leading to the pool area. A modern white kitchen has island seating, tons of counterspace and opens to a large dining space with river and pool views. The sunroom has walls of windows and steps to an inviting patio area. The second floor is upscale with room for friends and family. A private primary suite has wonderful views, a stylish bath and great closet space. Two additional bedrooms and bath and laundry complete this light-filled floor. The third floor has great potential with a soaring ceiling and large windows promising future fun! The waterfront pool, inviting patios, riverfront dock and green gardens await your arrival. The saltwater pool is surrounded by a wrought iron fence, secure, yet allows views from all points. The patio has room for games and lounging. Garden areas and game playing lawns are ready for fun. An uncovered pergola and a top of the line dock is ready for your toys and boats. Parking for everyone and the best view in East New Market can be yours! Restaurants and shopping are close by too.

6011 Sunnyside Ct, East New Market

Listing courtesy of Compass. Contact: (410) 429-7425
$239,000
3 Beds ⋅ 3 Baths
Welcome to the desirable community of Pintail Landing in Cambridge, MD. This beautifully updated end-unit townhome offers 3 spacious bedrooms and 2.5 bathrooms, providing plenty of room for comfortable Eastern Shore living. The main level features a spacious living room with impressive 9-foot ceilings and a cozy gas fireplace, creating a warm and inviting space to relax. The completely renovated kitchen boasts new cabinetry, flooring, countertops, backsplash, and appliances, offering both style and functionality. Just off the kitchen, a versatile sunroom bonus room provides the perfect space for a home office, sitting area, playroom, or hobby space. Upstairs, you'll find three generously sized bedrooms, including a large primary bedroom with two closets and a private bath featuring a updated double vanity, soaking tub, and separate shower. Recent improvements include a new roof installed in 2021. Additional features include a utility room with washer and dryer, extra storage space, and the added privacy that comes with being an end unit. Conveniently located near shopping, restaurants, marinas, beaches, boat ramps, and major routes, this move-in-ready home offers the perfect blend of comfort, style, and convenience.

316 Old Squaw Ct, Cambridge

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

$1,999,750
3 Beds ⋅ 3 Baths
Waterfront Farm - Located along the shores of Marshy Hope Creek, this 113.14-acre farm, with an additional 1.322+/- acre adjoining lot, offers a rare blend of productive farmland, natural beauty, and thoughtfully maintained improvements. Approximately 52.6 acres are tillable and farmed for small grain, offering excellent agricultural opportunity. The remaining acreage comprises mature, open woodlands with cleared paths, suitable for nature walks and ATVs, that gently slope from the homesite down to the water’s edge. The meticulously maintained, single-story 3,270 sq ft home features one-story living. Cathedral ceilings, expansive living spaces, and an inviting layout designed for both comfort and entertaining. The home features three bedrooms and two-and-a-half bathrooms with a functional layout designed for both privacy and everyday living. Radiant floor heating provides consistent warmth throughout the home, reflecting the quality construction and ongoing care of the property. The home is set up for self-sufficiency with an outdoor wood boiler surrounded by a forest full of fuel. Maintained inside and out, the home is move-in ready and offers a rare combination of size, condition, and single-level design. Equestrian and farm amenities include a pole building with two horse stall doors, as well as an additional open shed for equipment or storage, and a water hydrant. Subdivisions are available with soils favorable for obtaining perc permits to create your own family compound. Whether you are seeking a working farm, recreational retreat, horse property, or private waterfront estate, this remarkable property is a great investment opportunity.

5113 River Rd, Hurlock

Listing courtesy of National Land Realty, LLC. Contact: 4434128971
$314,000
4 Beds ⋅ 3 Baths
Welcome to Blackwater Landing! Built in 2024 by DR Horton, this beautifully maintained 4-bedroom, 2.5-bath home offers modern living with all the benefits of new construction—without the wait. Situated on a desirable corner lot, this home features an open-concept floor plan with granite countertops, stainless steel appliances, and plenty of space for everyday living and entertaining. Upstairs, you'll find all the primary suite along with 3 additional bedrooms and shared full bath. You'll love the conveniently located second-floor laundry room. Step outside through the sliding glass doors to enjoy the fully fenced backyard featuring a new privacy vinyl fence—perfect for relaxing, pets, or outdoor gatherings. Additional highlights include a spacious 2-car garage, attractive curb appeal, and beautiful rose bushes that enhance the front mulch beds. With modern finishes throughout and only a couple years old, this move-in-ready home is waiting for its next owner to make it their own.

1650 Terrapin Cir, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$375,000
3 Beds ⋅ 2 Baths
Welcome to this versatile 3-bedroom, 2-bath home situated on nearly 2 acres in a peaceful country setting. The seller has recently installed a **BRAND NEW ROOF**, providing added value and peace of mind for the next owner. The property offers a flexible floor plan with a converted garage currently operating as a pet grooming business. This space could continue as a home-based business, be converted into a family room or recreation area, or be restored to a traditional garage. Outside, enjoy the fenced areas, run-in stable, storage shed, and plenty of open space for animals, gardening, or future improvements. The **above-ground pool is open and ready for summer enjoyment**, creating a great outdoor space for entertaining and relaxation. Conveniently located just minutes from Cambridge, Easton, and other Eastern Shore destinations, this property offers the opportunity to enjoy country living with easy access to nearby amenities. Whether you're looking for a primary residence, hobby farm, or home with business potential, this property offers a variety of possibilities.

7112 E New Market Ellwood Rd, Hurlock

Listing courtesy of Taylor Properties. Contact:

$350,000
3 Beds ⋅ 2 Baths
Welcome to your own waterfront retreat on the picturesque Galestown Millpond! Brimming with potential, this lovingly maintained home is ready for your personal touches to make it truly your own. The spacious floor plan includes a walk-out basement, offering endless possibilities for additional living space, guest accommodations, a recreation room, or extra bedrooms if desired. Car enthusiasts, hobbyists, and those needing extra storage will appreciate the impressive 28' x 36' detached garage. Outside, enjoy the privacy of a long driveway leading to a peaceful setting with a large backyard that backs directly to the water including your private dock! Spend the remainder of summer fishing, kayaking, or simply taking in the tranquil views right from your own backyard. Don't miss this opportunity to create your dream waterfront home in a beautiful, private setting.

5715 Galestown Newhart Mill Rd, Galestown

Listing courtesy of ERA Martin Associates. Contact: 4107491818
$399,000
3 Beds ⋅ 2 Baths
Brand NEW CONSTRUCTION with timeless appeal and modern convenience! This 3 bedroom 2 bathroom home is scheduled for completion Summer of 2026 and offers the perfect blend of comfort and functionality. Enjoy a thoughtfully designed layout with open living spaces, ideal for both everyday living and entertaining. Go under contract NOW and have time to make some personal selections! Conveniently located just minutes from shopping and dining, you will have easy access to everything you need while still enjoying the feel of a new, well planned home. Get in early and secure your spot-there may be time for personal selections depending on the stage of construction. Don't miss out on this opportunity to own a brand new home! Colors, materials, and siding selections are subject to change.

602 Edlon Park, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$284,999
3 Beds ⋅ 2 Baths
Historic District charm meets everyday convenience at 113 Willis Street. This adorable circa-1916 Victorian sits just down the street from the Choptank River and close to the heart of downtown Cambridge, where you can enjoy local restaurants, shops, parks, marinas, waterfront events, and the character that makes this Eastern Shore town so special. Inside, this three-bedroom home blends classic early 20th-century charm with practical updates, including newer windows, roof, siding, drywall, electrical wiring, and central air, an uncommon and valuable bonus in many historic homes. The welcoming wraparound porch gives the home instant curb appeal, while the fully fenced yard, alley access, off-street parking, and garage/workshop add everyday functionality that is hard to find in this setting. Whether you need storage, hobby space, tools, bikes, or a spot for weekend projects, the garage/workshop gives you flexibility beyond the main house. Cute, comfortable, updated, and full of Cambridge character, this home offers historic charm, modern comfort, and downtown convenience all in one very lovable package.

113 Willis St, Cambridge

Listing courtesy of Keller Williams Flagship. Contact:

$849,500
3 Beds ⋅ 3 Baths
Price adjustment! Charming custom Cape Cod built by R. Lucas on Church Creek with 150'+/- bulkheaded shoreline, 17K lb. lift and boat ramp perfect for launching kayaks, canoes, etc. The home offers spacious living areas boasting custom built-ins and woodburning fireplace. Just off the family room is access to a hallway with staircase to large unfinished space over the two car garage. Porch to the rear of the house situated to enjoy the tranquil water views. Roof new in 2026 along with other recent upgrades.

4712 Steamboat Rd, Woolford

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$375,000
3 Beds ⋅ 2 Baths
Charming Cape Cod located in Cambridge’s desirable Historic West End District, just minutes from Downtown, Long Wharf, Great Marsh Park, YMCA, and the Cambridge Yacht Club. This well-maintained 3BR/2BA home offers over 1,700 sq ft with a flexible floor plan featuring a main-level bedroom and full bath, spacious living room with hardwood floors and fireplace, formal dining room, and large kitchen. Upstairs includes two generously sized bedrooms with hardwood flooring throughout. Enjoy the enclosed front porch, detached oversized garage/workshop, corner lot location, and off-street parking. Located within city limits and near the Ironman/Eagleman race course, making it ideal as a primary residence, second home, or investment property.

201 Belvedere Ave, Cambridge

Listing courtesy of Keller Williams Realty. Contact: 3023600300
$325,000
3 Beds ⋅ 1 Baths
Cozy all brick Colonial in highly sought out historic West End. Glenburn Ave is one of Cambridge's most beautiful historic streets. The home is located on a corner lot just 2 blocks from the Choptank River, parks and boat ramp. It is walking distance to downtown shops, restaurants, churches, schools, banks and the YMCA. This 1,408 st. ft. home has 1 bedroom, gally kitchen, dining room, laundry and large living room on the first level. The second level has beautiful hard wood floors, 1 full bath, 2 large bedrooms with pull down stairs for attic access. The full bath has large linen closet and ceramic tile. 2 car garage with workshop and wood burning fireplace. The yard is inviting and beautifully landscaped. The home has been lovingly cared for and well maintained through-out the years. It has been only family owned for generations. A must see!!

314 Glenburn Ave, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$475,000
1 Beds ⋅ 1 Baths
Exceptional waterfront opportunity with gorgeous water views, deep water access, and extensive boating amenities in a welcoming, waterfront neighborhood known for its friendly and laid-back atmosphere. This fully ADA-compliant 1-bedroom home features a thoughtfully renovated full bath with roll-in tiled shower, quartz vanity, tile flooring, and barn doors designed for accessibility and ease of use. Relax on the enclosed porch overlooking the water or head outside to the impressive pier offering approximately 6’ MLW, a lookout platform, and four boat lifts including two 1,500lb jet ski lifts, an 8,000lb lift, and a 20,000lb lift installed in 2022—an incredible setup for boating, fishing, and enjoying life on the water. Additional improvements include a new 50-year architectural shingle roof with transferable warranty installed in 2023 and a new well in 2024, plus public sewer service. Wheelchair ramp and lift convey. Detached garage/workshop with concrete floors and newer electric panel offers excellent storage and workspace potential, plumbing in workshop is currently disconnected- but could be hooked up by the new owner. There is an additional storage shed near the pier perfect for kayaks, fishing gear, and outdoor equipment. Bring your personal touches and bring this home to life! Property is being sold as-is. Appointment required for all showings.

5023 Russell Rd, Woolford

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

$629,900
2 Beds ⋅ 2 Baths
Enjoy breathtaking Honga River and Chesapeake Bay views from this exceptional waterfront property featuring a long private pier with multiple slips and two boat lifts. This well-maintained 2 bedroom, 2 full bath home offers comfortable coastal living with a riprapped shoreline, spacious yard and endless opportunities for boating, fishing, crabbing and embracing the Hoopers Island lifestyle. The expansive waterfront deck offers the perfect place to relax, entertain and enjoy cookouts with family and friends while taking in the panoramic waterfront views. Stunning sunrise and sunsets create the ideal setting for a full-time residence, weekend getaway, a peaceful waterfront retreat. Bring your golf cart and bicycles and enjoy nearby local favorites including Old Salty’s Restaurant and Hooper’s Island General Store. Conveniently located within walking distance to a local marina and public boat ramp.

1709 Doeller Rd, Fishing Creek

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$215,000
3 Beds ⋅ 1 Baths
Tucked away on a very private 2-acre wooded lot, this 3 bedroom, 1 bath rancher offers peaceful country living with room to spread out. Surrounded by mature trees, the property provides a serene setting with plenty of privacy. Includes a 24x24 detached garage with electric, spacious yard and convenient one-level living. The seller has significantly reduced the price to reflect repairs needed following a recent home inspection.

5260 Wilson Rd, Cambridge

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$187,000
2 Beds ⋅ 1 Baths
NICE WATER FRONT PROPERTY WITH APPRAISAL IN HAND! WHERE CAN YOU FIND A 2 BEDROOM HOME IN GOOD CONDITION WITH GREAT WATER FRONTAGE FOR THIS PRICE ! SHOW AND SELL BEFORE ITS GONE!

636 Hills Point Rd, Cambridge

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty - OP. Contact: 4102083500
$234,816
2 Beds ⋅ 1 Baths
Price Improvement!!!! Welcome to 214 East Appleby Avenue. This cute bungalow has quality features and has been recently updated. Perfect porch for summer evenings. Large lot with plenty of room for pool, swing set, gazebo and/or large garden. With this much outdoor space you can have a summer of fun. Inside hardwood floors, large living room windows make a bright light filled space. Kitchen is galley style with real wood cabinetry . Laundry room located off the kitchen. 2 bedrooms and a full bath down . Fixed stairs to attic with new insulation and room for additional bedroom/bath or just great storage. The yard is large with HUGE intown garage with work area and office space. Garage even has loft storage area. Turn key and ready for all types of financing. If you are tired of renting and or need space for your business without HOA restrictions this may be the perfect home for you.

214 E Appleby Ave, Cambridge

Listing courtesy of Long & Foster Real Estate, Inc.. Contact: 4102218000
$349,900
4 Beds ⋅ 3 Baths
Beautifully maintained and newly refreshed 4BR/2.5BA Colonial in sought after Longboat Estates. Park in the double-wide driveway or attached two-car garage and enter through the covered front entry into a light-filled interior featuring fresh paint, luxury flooring, carpeting, and recessed lighting. The main level offers a welcoming living room, convenient half bath, and an open-concept layout perfect for everyday living and entertaining. The spacious family room with gas fireplace flows seamlessly into the dining area with sliding door access to the backyard. The kitchen features ample cabinetry with under cabinet lighting, granite countertops, tiled backsplash, stainless steel sink, a pantry, and a movable island with a wood top. A stylish mudroom with barn doors provides access to the garage, complete with a custom epoxy floor. Upstairs, enjoy the convenience of second-floor laundry, three generously sized bedrooms, a full bath, and a private primary suite featuring a walk-in closet and en suite bath with double vanity and a large walk-in shower. From the main floor's sliding doors, step outside to a newly installed paver patio overlooking expansive green space and backing to woods, perfect for relaxing or entertaining. This move-in ready home also includes an in-home sprinkler system and is located in a community offering a fenced pool, boat ramp, and piers. Conveniently located near shopping, dining, and major commuter routes.

138 Regulator Dr N, Cambridge

Listing courtesy of LPT Realty, LLC. Contact: 8773662213
$285,900
3 Beds ⋅ 1 Baths
Located just outside the city limits, this ranch home has just been remodeled with luxury vinyl plank floors. The kitchen and bathroom have been remodeled, featuring modern finishes, solid countertops. A large attached rear wood deck provides a great spot to relax and enjoy peace and quiet. New appliances, all fresh paint and a heat pump await the buyer. The property enjoys access to public water and public sewer without City of Cambridge real estate taxation. Convenient to all public schools, churches and US Rte. 50. Large rear yard has numerous trees and a shed. This suburban ample lot is in walking distance of the Choptank River. Owner is prepared to make this your HOME.

111 Richardson Dr, Cambridge

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

$379,000
4 Beds ⋅ 2 Baths
Located in the heart of historic downtown Cambridge, this inviting residence is walking distance from the best restaurants, bars, and shopping our town has to offer! The formal living and dining areas feature elegant crown molding, hardwood flooring, and soaring nine-foot ceilings, all centered around a cozy gas fireplace that adds warmth and charm. The spacious kitchen is designed for both everyday living and entertaining, offering double wall ovens, a five-burner gas cooktop, stone countertops, and the convenience of dual sinks with disposals. Recent improvements provide peace of mind, including an architectural shingle roof. The home’s HVAC system was upgraded to natural gas in 2017, giving you flexible heating options with gas, electric, or a combination of both. The main level includes a convenient guest bathroom with a shower. Outside, the generously sized backyard is the perfect space for outdoor activities, pets, or simply relaxing. A storage shed offers practical space for tools, bikes, and more. Upstairs, you’ll find four comfortable bedrooms, a full bathroom, and a dedicated office. Much of the interior and exterior has been recently repainted, giving the home a refreshed feel.

606 Locust St, Cambridge

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

$269,999
3 Beds ⋅ 2 Baths
Freshly renovated 3-bedroom, 2 full bath home located in the heart of Cambridge. This move-in ready property features updated flooring, fresh paint, and modern finishes throughout. Enjoy a spacious layout with comfortable living areas and washer and dryer hookups for added convenience. The property also includes a storage shed, providing extra space for tools, bikes, or outdoor equipment. Conveniently located near shopping, dining, schools, and downtown Cambridge attractions. Great place to call home!

817 Washington St, Cambridge

Listing courtesy of Keller Williams Realty Delmarva. Contact: (410) 524-6400
$244,900
3 Beds ⋅ 2 Baths
*Owner Financing Option* Welcome to 506 High Street — a thoughtfully designed new construction home where modern comfort meets timeless Eastern Shore charm. With 3 bedrooms, 2 baths, and carefully curated finishes throughout, this home feels warm, inviting, and effortlessly livable from the moment you walk in. Inside, light-filled spaces and beautiful luxury vinyl plank flooring create a relaxed, modern farmhouse feel. The kitchen was designed to be the heart of the home, featuring elegant quartz countertops, stylish cabinetry, and an easy flow for gathering, entertaining, and everyday life. Every detail has been selected with both beauty and functionality in mind, offering the peace of mind and efficiency that come with brand-new construction. The spacious primary suite provides a quiet retreat, while the additional bedrooms offer flexibility for guests, a home office, or growing families. Step outside to a fully fenced backyard — perfect for pets, gardening, backyard dinners, or slow evenings under the stars. Located in the heart of historic Cambridge, just moments from the waterfront, local restaurants, shops, and marinas, this move-in ready home offers the rare combination of new construction living with the character and charm of one of Maryland’s most beloved waterfront communities.

506 High St, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$1,399,000
6 Beds ⋅ 5 Baths
Set on 10 remarkably private acres in Dorchester County’s scenic Neck District, this custom-built waterfront retreat commands sweeping views of the Middle Chesapeake Bay and offers the rare combination of space, comfort, and true Eastern Shore serenity. With over 4,500 sq. ft., 6 bedrooms, 4.5 baths, rip-rapped shoreline, and exceptional indoor and outdoor living spaces, this is a property designed for gathering generations of family and friends. A long private approach welcomes you to a setting where nature and waterfront living take center stage. Inside, hardwood floors, timeless architecture, and expansive Bay views create a warm yet elegant atmosphere. The waterfront family room features a striking stone fireplace with wood-burning insert and opens seamlessly to both the screened porch and covered deck, creating effortless indoor-outdoor living. The spacious kitchen was designed with entertaining in mind, offering a center island, breakfast bar, abundant cabinetry, stainless steel appliances, double wall ovens, pantry storage, and an oversized breakfast room ideal for casual mornings by the water. Formal living and dining rooms provide additional space for hosting holidays and special occasions. The first-floor primary suite serves as a private waterfront sanctuary with direct access to the covered porch and peaceful Chesapeake Bay views. Upstairs, five spacious guest bedrooms and three full baths—including a private en-suite—offer flexibility for large families, guests, or vacation rental potential. Vaulted ceilings and dormer windows add architectural charm and natural light throughout the second level. Outside, the lifestyle only gets better. Spend summer days around the inground pool, rinse off in the outdoor shower after boating or kayaking, enjoy crab feasts on the screened porch, or gather around the waterside fire pit as the sun sets across the Bay. The partially wooded acreage provides exceptional privacy while attracting an abundance of wildlife including bald eagles, deer, ducks, geese, and shorebirds—an everyday reminder of the natural beauty that surrounds you. Located on Ragged Point with Eastern Shore favorites like Soft & Salty Seafood and Danny's Seafood, this property offers easy access to fresh seafood, marinas, boating, and some of the finest fishing and crabbing waters on the Chesapeake Bay. The nearby Neck District Grill is a great spot for breakfast, lunch or weekend dinner. Whether you are searching for a full-time waterfront residence, luxury weekend escape, or investment opportunity with proven vacation rental appeal, this extraordinary property delivers the privacy, waterfront lifestyle, and authentic charm that buyers are seeking on Maryland’s Eastern Shore.

5332 Ragged Point Rd, Cambridge

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