Dorchester Homes for Sale

Dorchester Homes for Sale

Welcome to Dorchester County, Maryland, a hidden gem nestled on the Eastern Shore of the Chesapeake Bay. Known for its stunning natural beauty, rich history, and vibrant community, Dorchester County offers a unique blend of small-town charm and outdoor adventure. With miles of scenic waterways, lush landscapes, and an array of wildlife, it’s no wonder that this area is a favorite among nature lovers and outdoor enthusiasts alike.

Dorchester County is steeped in history, with quaint towns like Cambridge showcasing beautifully preserved architecture, local shops, and delightful eateries that reflect the area’s maritime heritage. The county’s cultural scene is vibrant, featuring arts festivals, farmers markets, and charming events throughout the year that bring the community together.

For those considering a move to this picturesque locale, you’ll find a variety of homes for sale that cater to diverse lifestyles and preferences. From historic waterfront properties with breathtaking views of the Choptank River to cozy single-family homes nestled in peaceful neighborhoods, Dorchester County has something for everyone. Whether you’re looking for a serene retreat or a vibrant community to call home, the real estate options here are both inviting and affordable.

Discover the charm of Dorchester County and explore the homes available for sale today. Embrace the lifestyle you’ve always dreamed of in a place where history, nature, and community come together in perfect harmony. Your new home awaits!

Newest Dorchester Homes for Sale

$345,000
4 Beds ⋅ 3 Baths
Welcome to this recently built home in lovely Heron Point, where comfort and convenience unite! Step in to the wide open floor plan where gathering with friends and family comes easy. Whether hosting game night or preparing your fave dish in the bright, airy kitchen. Need some quiet time/work space, private OFFICE conveniently located on the main level. Upper level features spacious primary suite with walk in closets and 3 additional bedrooms where the walk ins continue. Plenty of natural light and comfortable design gives one a warm and welcome experience. Ready to head out? Enjoy morning coffee to evenings out, being just a few minutes from all the shops and eateries in charming downtown Cambridge. All this, and several waterfront parks surround the town for swimming, boating or just taking in the natural beauty and wildlife. Happiness is just around the corner!

11 Saddle Bill Cir, Cambridge

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

$165,000
3 Beds ⋅ 1 Baths
Discover a rare opportunity in Toddville, MD, just south of Blackwater National Wildlife Refuge. Situated on 3.64 acres, this elevated home (approximately 5.5 feet above grade) offers expansive marsh views and an exceptional setting where wildlife abounds, including the area's renowned Sika deer. Featuring 3 bedrooms and 1 full bath, the home has solid bones and includes central air conditioning, a private well, and septic system. Whether you're looking for a hunting retreat, weekend getaway, or a property to renovate and make your own, the possibilities are plentiful. Bring your vision—this handyman special is ready for updates, including paint and general TLC. Enjoy the peace, privacy, and natural beauty of Maryland's Eastern Shore while creating your ideal escape from the everyday. Property is being sold strictly As Is.

2624 Toddville Rd, Toddville

Listing courtesy of Coldwell Banker Realty. Contact: 4102638686
$159,000
4 Beds ⋅ 2 Baths
Charming home in need of TLC. Live here or use it as a rental. 4 Bedrooms on upper floor with possible 5th bedroom on 1st floor. 1.5 bath home zoned commercial with residential use. Waking distance to downtown. Property is located on a busy commutable street with great exposure. Home being sold As Is. Adjoining 2 lots are also available for purchase. 308-310 Washington St MLS # MDDO2012882.

312 Washington St, Cambridge

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: (800) 383-3535
$385,000
4 Beds ⋅ 3 Baths
Welcome to Long Boat Estates, a water-oriented community located just minutes from the water, docks, and boat ramps. Residents also enjoy access to a private community pool. This spacious home offers four bedrooms and three full bathrooms. The upper level features three bedrooms and two full baths, including a private bathroom in the primary bedroom. The lower level includes an additional bedroom, a full bathroom, and a walkout to a screened-in porch. A large laundry room with a kitchen size sink and plenty of cabinet storage is also located on this level. The kitchen is equipped with stainless steel appliances, granite countertops, and a center island that provides additional workspace. Just off the dining room is a second screened-in porch that leads to an open-air deck, creating multiple areas for relaxing and outdoor entertaining. As an added bonus check out the Solar Panels on the roof that are OWNED and that make your electric bill much easier to pay each month! Conveniently located just minutes from Route 50 and a little over an hour from Ocean City, this home offers the perfect combination of comfortable living, outdoor space, and easy access to the water. Solar panels are owned by sellers and not leased

145 Regulator Dr N, Cambridge

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

$195,138
2 Beds ⋅ 1 Baths
Charming, Affordable Cottage in a Prime Location! This inviting 2-bedroom, 1-bath home is an excellent opportunity for first-time buyers, downsizers, or investors. The interior was thoughtfully renovated in 2001 with updated flooring, modern kitchen cabinetry, fresh paint, and other improvements, creating a warm and welcoming living space. The unfinished second level offers exciting potential for future expansion, additional storage, a hobby room, home office, or other creative uses to fit your needs. Ideally situated within walking distance of shopping, restaurants, and the scenic Choptank River, this home combines affordability, convenience, and opportunity. Whether you're looking for your first home or a smart investment, this property is full of potential and ready for its next owner.

913 Roslyn Ave, Cambridge

Listing courtesy of Eastern Shore Real Estate, LLC. Contact: 4103042011
$899,999
4 Beds ⋅ 3 Baths
Cambridge - waterfront paradise on Jenkins Creek, offering direct, easy access to the Choptank River! Nestled on a private lot with a peaceful, country feel, this charming home combines serene Eastern Shore living with the convenience of being just minutes from downtown Cambridge. Step inside to bright, sunlit interiors featuring soaring cathedral ceilings and rich hardwood floors. Cozy up on cool winter evenings by the fireplace/ woodstove, or unwind in the spacious main-floor primary suite, complete with a walk-in closet, updated bath with a walk-in shower, and direct access to the deck through large sliding doors framing picturesque water views. Upstairs, you'll find two additional bedrooms, a full bath, a versatile bonus room or potential fourth bedroom, and generous extra space ideal for storage or future expansion. Outdoor living is truly exceptional, featuring two private decks, a welcoming front porch, and a wonderful screened porch perfect for relaxing or entertaining. The rip-rapped shoreline includes a private dock equipped with water and electricity—ready for your boating and fishing adventures. Complete with an attached oversized garage, this captivating coastal retreat has so much to love!

2503 Legacy Ct, Cambridge

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

1648 Taylors Island Rd, Woolford

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$695,000
4 Beds ⋅ 3 Baths
Experience the charm of waterfront living with breathtaking sunrise views over Madison Bay. Set on 2.2 acres, this beautifully maintained 4 bedroom, 3 bath home offers approximately 800 feet of rip-rapped shoreline, a private deep-water pier with multiple slips, the perfect blend of comfort and outdoor recreation. The home features a beautifully renovated kitchen with custom cabinetry, quartz countertops, GE Café appliances, brand-new Bosch high-efficiency inverter heat pumps, new luxury vinyl plank flooring and a large waterfront deck perfect for entertaining or simply relaxing while taking in the scenic water views. Additional features include an attached two-car garage, detached garage/storage building, private deep well and county sewer. Enjoy boating, fishing, kayaking, biking and running right outside your door. Located near Blackwater National Wildlife Refuge and public hunting lands, this property is ideal for outdoor enthusiasts and nature lovers. Conveniently located near the Madison public boat ramp, volunteer fire company and just 15 minutes from Route 50 and Cambridge, with shopping, restaurants and Emily's Produce nearby. Whether you are looking for a full-time residence or private waterfront retreat, this property offers the very best of Maryland's Eastern Shore lifestyle.

4825 Madison Canning House Rd, Madison

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$295,000
4 Beds ⋅ 2 Baths
Discover the space, character and walkability of downtown Cambridge in this beautifully updated historic home. Offering 2,316 square feet, four bedrooms and two full bathrooms, the property blends distinctive Victorian details with substantial modern improvements. Relax on the covered front porch, complete with a classic porch swing, or enjoy the neighborhood views from either of the home’s two upper-level balconies. Located just blocks from the Choptank River, Cambridge Yacht Club, restaurants, coffee shops and local boutiques, this home places some of the city’s best amenities within an easy walk. Major capital improvements include a new roof, new kitchen appliances, upgraded electrical and plumbing, new sewer connections, storm windows, a Rinnai tankless gas water heater and high-end, two-zone low-profile radiators. Inside, refinished hardwood floors and original architectural details create a warm and inviting atmosphere. The living room features built-in bookcases and a fireplace and opens to a formal dining room with bay windows and an elegant chandelier. The kitchen offers stainless steel appliances, quality countertops and a charming breakfast nook. Two additional flexible rooms provide excellent options for home offices, a nursery, hobby space or additional storage. The main level includes a bedroom and full bathroom, offering flexibility for guests or one-level living. Upstairs, the spacious primary bedroom features a dedicated wardrobe room and convenient access to a full bathroom with a classic clawfoot tub. Two additional bedrooms open to an adjoining balcony. Across the street, the community garden provides an opportunity to grow flowers, herbs and fresh produce while enjoying the convenience of downtown living. Additional highlights include a private driveway, covered carport, rear accessibility ramp, backyard storage shed, no HOA and not located in a flood zone. With generous living space, valuable updates, off-street parking and an exceptional historic-district location, this distinctive Cambridge home is ready for its next chapter.

817 Locust St, Cambridge

Listing courtesy of Northrop Realty. Contact: (302) 539-0800
$1,250,000
3 Beds ⋅ 3 Baths
Welcome to Crump Point, an extraordinary renovated waterfront sanctuary nestled on approximately 5± private acres overlooking the tranquil waters of Church Creek. Offering exceptional privacy and captivating panoramic views, this remarkable property captures the essence of Eastern Shore waterfront living. Thoughtfully designed to embrace its breathtaking surroundings, the 3-bedroom, 2.5-bath residence offers stunning water views from nearly every room. The main level is anchored by a spacious gourmet kitchen featuring an oversized island, creating the perfect space for entertaining or gathering with family while enjoying the picturesque waterfront backdrop. All new stainless steel appliances throughout. The first-floor primary suite provides a private retreat complete with serene waters views, waterside deck, walk-in closet, walk-in shower, and oval soaking tub. Outdoor living is equally impressive with a spacious waterfront deck, screened waterside porch, and an upper-level waterside deck—ideal for morning coffee, evening sunsets, or simply taking in the ever-changing beauty of Church Creek. A private pier offers direct access to the water for boating, kayaking, fishing, and crabbing, while the beautifully landscaped grounds provide ample room to enjoy the peaceful surroundings. Additional features include a circular driveway, attached two-car garage, first-floor split-unit heating and cooling, and second-floor central air with baseboard heat. Whether you’re seeking a full-time residence or a weekend waterfront escape, Crump Point offers a rare opportunity to own an exceptional Eastern Shore property where privacy, natural beauty, and timeless waterfront living come together in perfect harmony.

1619 Perseus Rd, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$424,900
3 Beds ⋅ 3 Baths
Coming Soon! One of a kind 31+ acre farmette with established trails, open fields, ponds and Farm Creek water frontage, offering excellent Sika deer, goose and duck hunting and endless opportunities to enjoy the outdoors. The property includes a well-maintained 3 bedroom, 2 3/4 bath home with a conditioned crawl space, 3 stall barn, fenced pastures, pole barn and shop/shed. The perfect blend of recreation, hobby farming and peaceful country living for the hunter and nature enthusiast alike.

2562 Toddville Rd, Toddville

Listing courtesy of Meredith Fine Properties. Contact: 4108226272
$219,999
3 Beds ⋅ 2 Baths
Adorable + affordable - 3BR/2BA rancher on .92 acres on a no-through street. This one-story home has been lovingly-maintained by the same owner since it was built. Great floorplan with spacious living room, kitchen and dining room combo. Primary bedroom with ceiling fan and full, en-suite bath with a tub/shower combo. 2 additional bedrooms with ceiling fans, 2nd full bath with a tub/shower combo. Centrally located between Preston, Hurlock, and Federalsburg - you are just minutes to shopping, dining, public parks, and events. Close to plenty of Eastern Shore landmark towns - 14mi to historic Downtown Easton, 20mi to Cambridge on the banks of the Choptank River, 30mi to Saint Michaels, 40mi to the Chesapeake Bay Bridge, about 45mi to the beloved Delaware beaches, 50mi to Dover, Delaware State College, or Chestertown, Washington College. Sizes, taxes, distances approximate.

6906 Midfield Rd, Hurlock

Listing courtesy of EXP Realty, LLC. Contact: 8888607369
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