Dorchester County Public Schools Homes for Sale

Dorchester County Public Schools Homes for Sale

Welcome to the charming community of Dorchester County, Maryland, where education meets opportunity through the esteemed Dorchester County Public Schools. Nestled along the picturesque Chesapeake Bay, this region offers a unique blend of small-town charm and access to quality educational resources, making it an ideal choice for families looking to settle down.

Dorchester County Public Schools serve a diverse student population, committed to fostering academic excellence and personal growth. With a focus on creating a supportive learning environment, the district boasts a range of programs tailored to meet the needs of every student. From innovative STEM initiatives to robust arts and athletics programs, parents can rest assured that their children are receiving a well-rounded education. The dedicated staff and faculty strive to cultivate critical thinking, creativity, and collaboration, preparing students for success in an ever-evolving world.

As you explore the homes for sale in this vibrant area, you’ll find a variety of options that cater to different lifestyles and budgets. From charming historic homes to modern new constructions, Dorchester County offers an array of real estate opportunities that reflect the community's rich heritage and forward-thinking spirit. Many neighborhoods are conveniently located near schools, parks, and recreational facilities, making it easy for families to enjoy a balanced lifestyle.

Discover the perfect home in Dorchester County, where quality education and a welcoming community await you. Embrace the opportunity to plant roots in this beautiful region, and watch as your family thrives in both their academic pursuits and daily adventures. Welcome home!

Newest Dorchester County Public Schools Homes for Sale

More photos coming. 4 Bedroom, 1.5 bath home zoned commercial with residential use. Waking distance to downtown. Property is located on a busy commutable street with great exposure. Adjoining 2 lots are also available.

312 Washington St, Cambridge

Listing courtesy of Berkshire Hathaway HomeServices Homesale Realty. Contact: (800) 383-3535

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. 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.

145 Regulator Dr N, Cambridge

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

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

4 Beds ⋅ 3 Baths

COMING SOON! Waterfront lover's paradise on Jenkins Creek with quick access to the Choptank River! Nestled on a private lot with a peaceful, country feel and just minutes from downtown Cambridge, this beautiful home offers the ultimate Eastern Shore lifestyle.

2503 Legacy Ct, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545

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

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

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

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

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

2 Beds ⋅ 1 Baths

Have you been looking for a great deal on a project house? Here you go this could be your tiny house within walking distance to shopping, doctors, grocery. Rehab and start a rental portfolio and rent to Hyatt Employees; this East Cambridge house is just a quick bike or scooter ride to the resort. Renovate, rent and use the income or equity to purchase another property. Nice size yard already has a swing set. Looking to rehab a property and make affordable living for parents or a child that's ready to go out on their own. Take a look.

1007 Roslyn Ave, Cambridge

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

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

4 Beds ⋅ 1 Baths

Experience the timeless charm of Maryland's Eastern Shore at 4707 Steamboat Road in the peaceful community of Woolford MD. Just steps from the shores of beautiful Church Creek, this beautifully updated traditional farmhouse offers picturesque water views from the screened front porch and the perfect blend of classic Eastern Shore character and modern comfort. Inside, you'll find a bright, open-concept living and dining area that flows effortlessly into a spacious gourmet kitchen featuring updated cabinetry, a gas range, and upgraded flooring. Original hardwood floors throughout the foyer and first-floor bedrooms preserve the home's timeless appeal, while the generously sized rooms showcase the craftsmanship and charm of a bygone era. Extensive recent improvements make this home truly move-in ready. Recent updates include updated double-pane windows for improved energy efficiency, a new refrigerator (2024), new washer and dryer (2025), a new well pump, an owned water treatment system, energy-efficient mini-split heating and cooling systems, luxury vinyl plank flooring upstairs and downstairs, and a new electrical panel—all completed to provide comfort and peace of mind for the next owner. Step outside and enjoy everything this property has to offer. Sip your morning coffee on the rear deck overlooking the spacious backyard, or unwind on the screened front porch while taking in peaceful views of Church Creek. The large lot offers plenty of room to expand, garden, or build a future garage, while the well-maintained folk barn provides abundant storage and adds authentic character to this charming Eastern Shore setting. Whether you're searching for a full-time residence, a peaceful weekend retreat, or a place to enjoy the slower pace of living, 4707 Steamboat Road offers a rare opportunity to own a beautifully updated farmhouse in one of Dorchester County's most scenic locations. As an added bonus, additional equipment and personal property will convey with an acceptable offer.

4707 Steamboat Rd, Woolford

Listing courtesy of Keller Williams Realty. Contact: 3028467839

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