Dorchester County Public Schools Homes with Pier/Dock Amenities

Dorchester County Public Schools Homes with Pier/Dock Amenities

Welcome to Dorchester County, Maryland, where picturesque waterfront living meets exceptional educational opportunities! Nestled along the scenic shores of the Chesapeake Bay, Dorchester County offers a vibrant community atmosphere, perfect for families seeking both a tranquil lifestyle and access to quality education.

Dorchester County Public Schools is dedicated to fostering academic excellence and personal growth for all students. With a commitment to innovation and community involvement, the district provides a range of educational programs and extracurricular activities designed to engage students and prepare them for future success. Families can take pride in knowing that their children are receiving instruction from dedicated educators in a supportive environment, with a focus on both academic achievement and character development.

In addition to its strong educational offerings, Dorchester County boasts stunning homes with pier and dock amenities, ideal for those who appreciate the beauty of waterfront living. Imagine waking up to breathtaking views and having direct access to the water for fishing, boating, or simply enjoying the serene ambiance of nature. These homes not only provide a lifestyle of leisure but also an opportunity to create lasting memories with family and friends in a picturesque setting.

Whether you're drawn to the exceptional schools, the charming community, or the allure of waterfront living, Dorchester County is the perfect place to call home. Explore our listings today and discover your dream home in this beautiful Maryland county, where education and lifestyle harmoniously blend.

Newest Dorchester County Public Schools Homes with Pier/Dock Amenities

$324,900
2 Beds ⋅ 3 Baths
Welcome to 329 Shipyard Drive, a spacious townhome in one of Cambridge's most convenient waterfront communities. Offering over 2,400 square feet of living space, this home features an open, functional floor plan with generous room sizes, abundant natural light, and plenty of space for everyday living or weekend getaways. The main living area flows nicely into the kitchen and dining space, making it easy to entertain family and friends. Upstairs, you'll find comfortable bedrooms, including a spacious primary suite with its own private bath and ample closet space. Located in a gated, water-oriented community, residents enjoy access to a community pool and the convenience of being just minutes from downtown Cambridge's restaurants, shops, marina, and waterfront parks. Whether you're looking for a full-time residence, a low-maintenance second home, or an investment opportunity, this property offers the perfect combination of space, location, and easy living on Maryland's Eastern Shore.

329 Shipyard Dr, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: (410) 228-0800
$50,000
Build your dream home on this scenic 3.53-acre wooded lot in the exclusive Heron Harbor community, nestled along Webbs Creek, which feeds into the Choptank River. Surrounded by water and nature, this peaceful setting offers access to a community pier on navigable water—perfect for kayaking, boating, and enjoying fresh Eastern Shore crabs. HOA fees include dock maintenance and BIP septic hook-up access. With easy access to downtown Cambridge, shopping, restaurants, and more, you’ll enjoy the perfect balance of convenience and seclusion. Embrace the best of Eastern Shore living in this quiet, water-oriented community.

5229 Heron Rd, Cambridge

Listing courtesy of Northrop Realty. Contact: (302) 539-0800
$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
$429,900
3 Beds ⋅ 2 Baths
Luxury waterfront living awaits in this updated 3-bedroom (rare) Oakley Beach condo! Enjoy sweeping views of the Choptank River from the deck and a beautifully modernized kitchen featuring sleek quartz countertops ,custom island, and updated cabinet fronts. New LVP flooring. Gas fireplace, Hunter Douglas blinds including insulated, mechanized shade for as much or little view as you want ! Recent HVAC and hot water heater.(2023) Boat enthusiasts will love the included deeded boat slip equipped with a boat lift. Take advantage of fantastic community amenities like the pool, all just steps from your door. Truly worry free and move in ready! Schedule your tour today!

3 Oakley St Unit #202, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$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
$419,000
4 Beds ⋅ 3 Baths
Think you have seen this home?...better LOOK AGAIN!! This home has been refreshed inside and out and is simply stunning! From the moment you step inside you will notice the fresh, coastal design that welcomes you home. You will find light, airy hardwood floors throughout the home and a beautiful kitchen featuring furniture-finished cabinetry and upgraded counter tops, and ceramic tile floor. The breakfast bar has seating for up to five plus there's an additional breakfast area that is drenched in sunlight. The kitchen blends seamlessly into the family room featuring high ceilings, a gas fireplace, and custom built-in server cabinetry. This home features a spacious first floor owner's bedroom suite with soaking tub and walk in shower, plus a second bedroom with full bath and even a separate den/office. First floor laundry. Relax in the sun room overlooking the backyard or step out onto the covered rear porch and patio. Take the staircase up to the second floor to find 2 more huge bedrooms with a connecting "Jack and Jill style" full bath #3. This exceptional home features over 3700 Sq ft of quality built, craftsman style living space! The community of Longboat Estates is everything shore life should be! It is a beautiful community! An active, yet relaxing place to call home offering homeowners exclusive amenities to enjoy shore life... you will find the beautiful dock with 2 piers on Jenkins Creek leading out to the Choptank River. Bring your boat, kayak, fishing and crabbing gear. You and your family will love it here! Quality construction by Lennar.

123 Regulator Dr N, Cambridge

Listing courtesy of Chaney Homes, LLC. Contact: (410) 739-0242
$349,900
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
$314,900
3 Beds ⋅ 3 Baths
Lovely End Unit in Deep Harbor! This like-new, 3-level townhome delivers incredible value and convenience, a water view, and a long list of upgraded finishes throughout — including enhanced flooring, additional recessed lighting, high-end fixtures, composite decking, and upgraded kitchen + bath selections that elevate both style and function. Thoughtfully designed -the entry level features a welcoming foyer and versatile den—ideal as a home office, lounge, fitness space, or playroom—plus interior access to the attached garage. The main living level showcases an exceptional kitchen with abundant cabinetry, beautiful backsplash, recessed lighting, stainless steel appliances, large center island, and plenty of prep + storage space. Enjoy connection to the outdoors with two composite decks overlooking Cambridge Creek & Generation III Marina—perfect for morning coffee, sunset watching, or entertaining. The top floor features a lovely primary suite with tray ceiling detail, walk-in closet, private deck, dual vanities, and an oversized walk-in shower. Two additional bedrooms share a beautifully appointed hall bath. A great perk is the full-size stack washer & dryer which are conveniently located on the bedroom level. Deep Harbor amenities include: gated entrance, waterside walking paths, community pool, and marina access—and are all within walking distance to downtown Cambridge dining, shops, events, and waterfront recreation. **The unit is located in an area of Deep Harbor where short term rental like Air BNB, VRBO, etc. are permitted- making this a great investment opportunity as well! ** Boat slips are available on a first come first serve basis within the Deep Harbor Community OR utilize slip leases at: City of Cambridge's Municipal Yacht Basin, Dorchester Co., Generation III Marina, and Cambridge Yacht Club. Don’t miss this exceptional opportunity to secure a modern, low-maintenance home on the Eastern Shore!

519 Seaway Ln Unit #157, Cambridge

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

$75,000
Don’t miss this .30-acre homesite in Algonquin, a desirable water-access community just outside Cambridge. Situated on relatively high ground, this lot offers added peace of mind along with public water and sewer availability. As the last available lot in this established neighborhood, it is surrounded by mature landscaping and well-maintained homes with strong property values. Residents enjoy access to a community pier on Jenkins Creek, boat ramp, and trailer parking—ideal for embracing the Eastern Shore waterfront lifestyle.

4 Algonquin Rd, Cambridge

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

$239,000
2 Beds ⋅ 2 Baths
This cozy 2 bedroom, 2 bath condo is nestled in the sought-after waterside community of Deep Harbour. As you enter, you'll be greeted by a bright and spacious living area that flows seamlessly into the kitchen, equipped with modern appliances, sleek countertops, and ample cabinet space. The primary features a private en-suite bath and plenty of closet space, while the second bedroom offers versatility for guests or a home office. Outside, enjoy a private balcony with creek views, or take a stroll along the public riverwalk that outlines the community, with downtown restaurants and shopping just minutes away. Deep Harbour is a gated community with secure assigned garage parking, keypad/fob front building entry, and nearby boat ramps. Enjoy access to a community pool, nearby parks, playgrounds, the Fishing Pier, and the Harriet Tubman Museum & Educational Center in Cambridge. Nature lovers will appreciate the nearby Blackwater National Wildlife Refuge and its Visitor Center. Storage unit included.

900 Marshy Cv Unit #411, Cambridge

Listing courtesy of Benson & Mangold, LLC. Contact: 4108226665
$235,000
2 Beds ⋅ 2 Baths
Experience affordable waterfront living without compromising on lifestyle in this beautifully updated top-floor penthouse. From your private balcony, enjoy peaceful long-water views stretching toward the Choptank River and front-row seats to the Fourth of July fireworks over the water. Offering 1,493 square feet of thoughtfully updated living space, this 2-bedroom, 2-bath residence features new luxury vinyl plank flooring throughout, upgraded lighting, elegant chair rail detailing, and a spacious open layout designed for comfortable everyday living. The modern kitchen has been refreshed with all-new stainless steel appliances, while the full-size stacked washer and dryer add everyday convenience. The generous primary suite includes a spa-inspired bath with dual vanities, a walk-in shower, and timeless white marble flooring. Located within the secure, gated Deep Harbour waterfront community, residents enjoy elevator access, front-door intercom entry, an assigned indoor garage parking space, and the added benefit of a rare private storage unit. Deep Harbour offers an exceptional waterfront lifestyle with a community marina, piers, kayak launch, scenic walking paths, swimming pool, bathhouse, picnic areas, and beautifully maintained grounds along Cambridge Creek. Just moments from historic downtown Cambridge, you'll enjoy locally owned restaurants, shops, marinas, festivals, and the exciting Cambridge Harbor redevelopment on the Choptank River, bringing new waterfront dining, entertainment, and recreational amenities. Perfectly positioned for commuters and weekend travelers alike, Cambridge offers convenient access to Annapolis, Easton, Salisbury, Ocean City, and the broader Chesapeake Bay region—making it easy to enjoy coastal living while staying connected to work and recreation. Whether you're looking for a full-time residence, weekend retreat, or low-maintenance waterfront home, this penthouse delivers exceptional value, security, and an enviable Eastern Shore lifestyle. 𝗣𝗿𝗼𝗽𝗲𝗿𝘁𝘆 𝗛𝗶𝗴𝗵𝗹𝗶𝗴𝗵𝘁𝘀 • Top-floor penthouse with long water views toward the Choptank River • 1,493 sq. ft. | 2 Bedrooms | 2 Full Baths • Private balcony with water views and Fourth of July fireworks • New luxury vinyl plank flooring throughout • All-new stainless steel kitchen appliances • Full-size stacked washer & dryer • Spacious primary suite with dual vanities, walk-in shower & marble flooring • Upgraded lighting fixtures and chair rail detailing • Assigned indoor garage parking space • Rare private storage unit • Secure gated building with front-door intercom • Two elevators serving all residential floors • Waterfront community with marina, piers & kayak launch • Swimming pool, bathhouse, picnic areas & waterfront walking paths • Minutes to historic downtown Cambridge • Near the exciting Choptank Harbor waterfront redevelopment • Easy access to Easton, Annapolis, Salisbury, Ocean City & the Chesapeake Bay • Affordable, low-maintenance waterfront living on Maryland's Eastern Shore

700 Cattail Cv Unit #412, Cambridge

Listing courtesy of Kinetic Realty, Inc.. Contact: (443) 222-0010
$349,900
3 Beds ⋅ 3 Baths
Fully Renovated in Waterfront Community — Private Beach, Pier & Pavilion Access Included Everything is new. Everything is done. Just move in. This 3-bedroom, 3-bathroom raised rancher on Parsons Drive in Madison has been renovated top to bottom — and it sits in a waterfront community with private beach access, a fishing pier, and a community pavilion. New kitchen with stainless steel appliances, updated cabinetry, and generous counter space. New luxury flooring throughout. New HVAC system and CPVC plumbing. New siding. New spacious deck for entertaining or unwinding outdoors. Attached garage for everyday convenience. The full unfinished basement is a blank canvas — finish it for additional living space, set up a workshop, or use it for storage. The potential square footage here is a bonus most buyers overlook. All of this in a community where your amenities include a private beach, fishing pier, and pavilion — the waterfront lifestyle without the waterfront price tag. Every major system and finish has been replaced. Nothing to update, nothing to repair, nothing to wait for. Dorchester Sanitary Fee applies to the property

921 Parsons Dr, Madison

Listing courtesy of Real Broker, LLC - Chester. Contact: 8554500442
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