Dorchester County Public Schools Homes with Cottage Style

Dorchester County Public Schools Homes with Cottage Style

Welcome to the charming community of Dorchester County, Maryland, where the picturesque landscapes meet an exceptional educational experience. Nestled along the eastern shore, Dorchester County Public Schools (DCPS) is renowned for its commitment to fostering a nurturing and innovative learning environment for students from pre-K through high school. With a focus on academic excellence, DCPS offers a diverse curriculum that includes advanced placement courses, vocational training, and opportunities for extracurricular engagement, ensuring that every student can thrive and reach their full potential.

Families considering a move to this lovely area will find an array of delightful homes featuring cottage-style architecture, perfect for those who appreciate a cozy and inviting atmosphere. These charming cottages often boast unique characteristics such as quaint gardens, warm wooden interiors, and inviting front porches that beckon you to relax and enjoy the serene surroundings. Imagine sipping your morning coffee while soaking in the beauty of your garden or hosting friends for a delightful evening on your porch.

Living in Dorchester County not only provides access to a wonderful school district but also allows residents to immerse themselves in a close-knit community filled with rich history and natural beauty. With the Chesapeake Bay nearby, outdoor enthusiasts can enjoy activities such as fishing, kayaking, and hiking, making it the perfect place to call home. Explore the delightful cottage-style homes in this area and discover the perfect blend of comfort, community, and quality education that Dorchester County has to offer!

Newest Dorchester County Public Schools Homes with Cottage Style

$184,900
2 Beds ⋅ 1 Baths
Coming Soon - affordable 1 story home with new roof. Cute porch and alley accessible yard. Updated bath. Pine floors.

209 Dorchester Ave, Cambridge

Listing courtesy of Coldwell Banker Realty. Contact: 4105434545
$849,900
3 Beds ⋅ 2 Baths
Trade Traffic for Tides — Your Waterfront Island Escape Awaits! From the moment you cross the bridge onto Hooper's Island, something changes. A sense of peace settles in. Life slows down. The water sets the schedule, neighbors wave as they pass, and the pace becomes simpler, sweeter, and slower—in the very best way. This beautifully remodeled 3-bedroom, 2-full-bath waterfront home is being offered fully furnished and is already an established, highly successful 5-star Airbnb, renting for $430 per night. Whether you're looking for a personal island retreat, an investment property, or the best of both worlds, this home is ready to enjoy from day one. The entire home has been remodeled from the ground up, so nothing in the home is older than 5 years old- appliances, roof, well, mechanicals -you name it!! Imagine looking out your window and seeing crab boats, dolphins playing in the bay, and cruise ships and container vessels making their way across the horizon. A rear wall of floor-to-ceiling glass doors provides panoramic bay views, bringing the water into nearly every room. Cooking becomes relaxing because the views are amazing, even from the kitchen! Wake in the primary suite, open the blinds with a remote control, and take in the water views from the comfort of your bed. Freshly painted and featuring brand-new flooring throughout, the home combines comfortable coastal living with thoughtful modern updates. The crawl space had spray foam insulation, vapor barrier, and a new sump pump installed in 2026. The home is ADA accessible with a ramp to enter from the side, walk-in showers, wrap around Trex decking, and even paved sidewalks with railings leading the whole way to the dock. Smart technology integrated into so many aspects of the property! Access an app to control the thermostat, garage door, RING cameras, and even view the contents of your fridge so you can remember what you need to get at the grocery store! And then there's the waterfront. A private dock, built just two years ago, is ready for your next adventure and includes a 10,000-pound boat lift. Spend your days kayaking, swimming, boating, jet skiing, fishing, or crabbing—or simply sit by the water and watch island life unfold. Search the shoreline for sea glass and seashells, launch the kayak, or cast a line and see what the day brings. On this island, you won't need your car. Leave it parked and explore by foot, bike, or golf cart. Hooper's Island has a general store stocked with everyday essentials, from fishing tackle to ice cream, and Old Salty's, the island's only restaurant, serves wonderful fresh seafood alongside a laid-back tiki bar. Fun fact about Hooper's Island: Before it started as a culinary legend, it all started on this island in 1914 when Augustus E. Phillips opened the A.E. Phillips & Son packing plant. In 1956, faced with a surplus of crabs, Augustus' son and his wife opened a small 'shack' in Ocean City, MD... and we all know how that exploded with popularity! The original processing plant is still part of the company, and when operational, continues to process blue crabs and soft-shell crabs for regional locations.

1210 Horse Point Rd, Fishing Creek

Listing courtesy of Contigo Real Estate. Contact: 7172694566
$170,444
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
$430,000
2 Beds ⋅ 1 Baths
Adorable waterfront cottage nestled along the peaceful shores of Hudson Creek., This charming 2-bedroom, 1-bath home features an open-concept kitchen, dining, and living area designed to maximize comfort and showcase beautiful waterfront views and amazing sunsets. Additional features include front and back porches, firepit, fresh paint throughout and a detached storage shed for all your outdoor gear, Experience Eastern Shore waterfront living and spend your days fishing or crabbing from your private pier, launch your kayaks for an afternoon on the creek, or simply unwind on the deck while taking in the spectacular sunsets. This low-maintenance property has been successfully operated as an income generating vacation rental, making it an excellent opportunity as a personal getaway, investment property, or both. The home is being sold fully furnished, including two kayaks, a BBQ grill and deck furniture

915 Hudson Rd, Cambridge

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
$799,999
3 Beds ⋅ 2 Baths
SEIZE THE SUNSET! Enjoy waterfront tranquility right at your back door—and don’t miss this significant price improvement! If you’ve been searching for an immaculate, move-in-ready waterfront home with exceptional first-floor living, this may be the one. Major interior renovations were completed in 2022, and this beautifully updated and meticulously maintained 3-bedroom, 2-bath home offers more than 2,300 square feet of bright, inviting living space designed to showcase the beauty of the Eastern Shore. Panoramic waterfront views greet you from nearly every room, with the living room overlooking the breathtaking vistas of Fishing Creek. Two spacious living areas, each featuring a cozy fireplace, provide plenty of room to relax, entertain, and enjoy the changing seasons.The open gourmet kitchen is the heart of the home, featuring custom finishes, modern updates, and a built-in wine cooler—perfect for preparing meals, gathering with friends, or simply enjoying a quiet evening while taking in the view. Major systems and improvements have already been taken care of, offering peace of mind for the next owner. The roof was replaced in 2018, the HVAC system in 2022, and new thermostats were installed in 2024. An updated sprinkler system, new French gutter drains installed in 2025, and an improved Dry-Zone encapsulated crawl space further enhance the home's efficiency and long-term protection. The crawl space also features a new dehumidifier installed on a raised platform, new insulation, and an indoor monitoring system, all completed in 2026. For additional peace of mind, the home includes transferable USAA flood insurance along with annual Dry-Zone, HVAC, and pest control inspection contracts. Connected to public sewer, this home offers the convenience of simplified ownership from day one.Ideally located just a short distance from historic Cambridge and the Hyatt Regency Chesapeake Bay Golf Resort, with easy access to Easton, Oxford, and St. Michaels. Nature lovers will appreciate the close proximity to Blackwater Wildlife Refuge, where you can explore scenic trails, enjoy kayaking and biking, observe abundant wildlife, and perhaps catch a glimpse of the area's magnificent bald eagles. This is more than a home—it’s an opportunity to embrace the peaceful waterfront lifestyle, spectacular sunsets, and timeless charm of Maryland’s Eastern Shore, with the comfort and confidence of a home where many of the major updates have already been completed.

1318 Bell Ln, Woolford

Listing courtesy of TTR Sotheby's International Realty. Contact: 4106733344
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