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709 Chesapeake Dr, Stevensville
$550,000
4 Beds ⋅ 4 Baths
Two Homes, Endless Possibilities, and a Chesapeake Bay Lifestyle! Discover a truly unique opportunity in Bay City! This one-of-a-kind property offers not just one, but two separate homes, a two-car garage, and an incredible entertainment space, creating the perfect setting for a family retreat, multigenerational living, hosting guests, or generating vacation rental income! The main residence welcomes you with a spacious living room featuring a cozy fireplace, along with a family room boasting a soaring vaulted ceiling, built-in bar, and atrium doors that open onto an expansive deck. The kitchen is centrally located and open to both the Living and Family rooms. With three generously sized bedrooms and two full baths, there's plenty of room for family and friends to relax and enjoy all the comforts of home. But that's just the beginning! Just next door, you'll discover a fully furnished guest house offering exceptional flexibility as an Airbnb, vacation rental, in-law suite, or private accommodations for overnight guests. This charming retreat features a spacious living room, a private bedroom, a well-appointed kitchen with a skylight above the island and seating for two, plus sliding glass doors leading to a partially private yard. A spacious full bath completes this inviting space. And there's still more to explore! The attached two-car garage has been transformed into an extraordinary entertainment destination! Connected to the guest house, this incredible recreation area is designed for fun and relaxation. Accommodations include two bunk beds sleeping up to six, a pool table, comfortable lounge areas, a game area, and a separate adult gathering space complete with a bar. You'll also find a half bath and laundry area, making this an ideal space for entertaining family and friends. Step outside to enjoy the patio and shared fire pit, perfect for gathering, unwinding, and making memories long after the sun goes down. And then there's Bay City! Enjoy the wonderful lifestyle of this water-privileged Chesapeake Bay community, offering residents access to a boat ramp, fishing pier, picnic pavilion, expansive playground, and picnic areas right along the beautiful, scenic Chesapeake Bay boast incredible sunsets overlooking Annapolis! Whether you're searching for a family getaway, a property with room for everyone, a multigenerational living arrangement, or an investment opportunity with vacation rental potential, this property delivers possibilities you won't find every day. Two homes. Endless entertainment. Chesapeake Bay living. Income-producing potential. Properties this unique rarely come along! Don't miss your opportunity to own this extraordinary Bay City retreat. Vacation rental financials are available for buyers interested in exploring the investment potential!

709 Chesapeake Dr, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

807 Worcester Dr, Stevensville
$525,000
4 Beds ⋅ 3 Baths
Welcome to this beautifully updated 4-bedroom, 3-full-bath split-level home in a desirable water-access community on Kent Island! Offering a versatile floor plan, thoughtful improvements, and plenty of room to spread out, this home is ready for its next owners to move right in and enjoy. Step inside to discover a beautifully renovated kitchen, updated bathrooms, new flooring, and fresh paint throughout. Major improvements include a new roof in 2024, a new HVAC system in 2026, and a newly fenced backyard, providing peace of mind for years to come. The upper level features three comfortable bedrooms and two full bathrooms, while the spacious lower level offers an entirely different level of flexibility. Complete with a fourth bedroom, full bathroom, additional living area, and a second partial kitchen, this space is perfect for extended family, overnight guests, an au pair, or simply creating a private retreat. Outside, the newly fenced backyard offers plenty of space for entertaining, gardening, pets, or relaxing at the end of the day. Beyond the property, enjoy the benefits of living in a water-access community and all that the Eastern Shore lifestyle has to offer. With extensive updates already completed, flexible living spaces, and a wonderful Kent Island location, this home offers an incredible opportunity to enjoy comfortable living near the water. Come see the possibilities for yourself!

807 Worcester Dr, Stevensville

Listing courtesy of Berkshire Hathaway HomeServices PenFed Realty. Contact:

914 Bayside Dr, Stevensville
$2,200,000
3 Beds ⋅ 2 Baths
Bay City - If you are looking for a property that features beautiful sunsets on the bay, and outdoor living at the finest you found it! A builder's home with attention to detail from the custom heated pool and hot tub to the Danver stainless steel outdoor kitchen, Lynx grill, Lynx side burner, subzero ice maker, subzero refrigerator drawers and well as an outdoor living space with gas fireplace. Additional features of motorized retractable screens and aluminum shutters on pool house. Also, a boater's dream with a pier featuring a 13,000 lbs boat lift, 30,000 lbs high speed boat, jet ski lift and all new decking and lighting. Irrigation system and full property landscape and landscape lighting to also appreciate on this beautiful property. Crawlspace has been encapsulated and insulated and installed dehumidification system. This home is a MUST SEE, so call today for your showing appointment.

914 Bayside Dr, Stevensville

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

404 Victoria Way, Stevensville
$525,000
3 Beds ⋅ 3 Baths
There’s more here than meets the eye! This charming home may look like a classic rancher from the curb, but inside and out, it offers an impressive amount of flexibility. The main home features three bedrooms, two full bathrooms and an oversized family room overlooking the beautifully landscaped, fully fenced backyard with privacy fencing and a rear deck. But the real surprise is the separate studio-style bonus space with its own private entrance, full bathroom, stackable washer and dryer, refrigerator, cabinetry and countertop space. Whether you envision an in-law suite, work-from-home office, guest quarters or potential rental space, the possibilities are plenty. Outside, you’ll ALSO find a detached shed with concrete floors and electric, plus an extended driveway with double gates opening to an additional parking pad, perfect for a boat or camper. An encapsulated crawlspace and newer roof add extra peace of mind. Located in the community of Bay City, you’ll enjoy a neighborhood setting with water access, a playground with picnic area, PLUS just minutes from fine dining, restaurants, marinas, public parks, playgrounds and bike trails of Kent Island. Not to mention, easy access to the Chesapeake Bay Bridge or commuter bus stops.

404 Victoria Way, Stevensville

Listing courtesy of RE/MAX Executive. Contact:

912 Buckingham Dr, Stevensville
$475,000
3 Beds ⋅ 2 Baths
MOTIVATED SELLERS!!! Assumable VA Loan for qualifying buyers!! With a 5.2% interest rate. Welcome to this beautifully updated 3-bedroom, 2-bath home in the highly desired Bay City neighborhood! Situated on a spacious fenced in half-acre lot with community water access, this property offers the perfect blend of comfort and coastal community living. Recent improvements include new windows, a new HVAC system, brand new carpets upstairs, along with new kitchen flooring, appliances, and cabinets. Enjoy plenty of outdoor space and the 2 car garage! This home is ready to welcome its next owner!!

912 Buckingham Dr, Stevensville

Listing courtesy of Douglas Realty LLC. Contact:

26025 S Cherry St, Millsboro
$19,999
3 Beds ⋅ 2 Baths
WATERFRONT VIEW! BACK ON MARKET AT NO FAULT TO THE SELLER - ACT FAST AT THIS PRICE! Tucked away in the sought-after Bay City community of Millsboro, this 3-bedroom, 1.5-bath home offers the kind of peaceful marsh views that make every day feel like a getaway. Whether you're searching for a weekend retreat, vacation rental opportunity, or your own coastal escape, this property is ready to enjoy from day one while still offering room to add value and personal touches. Inside, you’ll find comfortable living spaces with plenty of potential to bring the home into full 2026 style and design. Outside is where this property truly shines — relax with your morning coffee overlooking the marsh, unwind after a beach day, or entertain while soaking in the natural beauty that surrounds you. Located just a short drive from Delaware beaches, restaurants, boating, and shopping, this is your chance to own an affordable beach-area oasis with views that are hard to come by. Bring your vision, add a little love, and turn this hidden gem into something truly special.

26025 S Cherry St, Millsboro

Listing courtesy of Coldwell Banker Realty. Contact:

323 Chenowith Dr, Stevensville
$672,800
4 Beds ⋅ 3 Baths
One of our most popular designs, the Doral offers formal and informal living areas with lots of room for the whole family to spread out. Your main level features a dining/den/flex space as well as a spacious family room and kitchen, breakfast area that flows to the spacious family room.. Add a light-filled morning room off the rear or expand your space with plan extensions. . Upstairs accommodates four nicely sized bedrooms, including aprimary suite with a massive closet area. and you can customize your lower level rec area to suit your needs. Located just a short walk to the waterfront, the community features a boat launch, pavillion, playground, and bayfront recreational area. Move in ready with versatile living spaces and a thoughtful layout.

323 Chenowith Dr, Stevensville

Listing courtesy of Keller Williams Flagship. Contact:

526 Victoria Dr, Stevensville
$550,000
3 Beds ⋅ 2 Baths

526 Victoria Dr, Stevensville

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

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