Osterville Homes with Bay Waterfront Features

Welcome to Osterville, a picturesque gem nestled in the heart of Barnstable, Massachusetts. Known for its stunning coastal beauty and rich maritime history, Osterville offers a perfect blend of charming New England aesthetics and modern amenities. This idyllic village is renowned for its quaint streets lined with boutique shops, gourmet restaurants, and art galleries, all contributing to its vibrant community spirit.

One of the most alluring aspects of Osterville is its breathtaking bay waterfront properties. Homes in this desirable area often boast direct access to the shimmering waters of Osterville Bay, providing residents with unparalleled opportunities for boating, fishing, and enjoying the serene coastal lifestyle. Imagine waking up to the gentle sound of waves lapping against the shore, with panoramic views of the bay stretching out before you. These waterfront properties often feature expansive decks, private docks, and beautifully landscaped yards, making them ideal for entertaining or simply relaxing in the sun.

Osterville’s waterfront homes are not just about stunning views; they also offer a unique sense of community. With a mix of seasonal and year-round residents, you’ll find a warm and welcoming atmosphere that fosters connection and camaraderie. Whether you’re looking for a charming cottage or a luxurious estate, Osterville’s real estate market has something for everyone.

Experience the magic of Osterville and discover the allure of bay waterfront living. Your dream home awaits in this enchanting coastal paradise!

Newest Osterville Homes with Bay Waterfront Features

$5,950,000

5 Beds ⋅ 8 Baths ⋅ 73525098 MLS

Overlooking the golf course within the coveted gated community of Oyster Harbors, this exceptional residence combines timeless design with modern comforts in a beautifully crafted coastal setting. The home is defined by generous proportions, abundant natural light, and refined architectural detail throughout. The kitchen is tailored for both everyday living and entertaining, offering high-end appliances, expansive stone countertops, and a custom mahogany butler's pantry that provides additional prep and serving space. A secluded primary suite enjoys its own dedicated wing on the first floor, complete with a luxurious bathroom, two walk-in closets, and French doors that open to a private patio overlooking the swimming pool and gardens. Outdoor amenities take full advantage of the serene setting, with covered porches and a Gunite pool with limestone surround, all positioned to capture views of the 14th fairway. Ownership includes deeded beach access and passenger dock rights.

179 Pineleigh Path, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .

$7,500,000

3 Beds ⋅ 6 Baths ⋅ 73520995 MLS

Nestled along the sparkling shores of North Bay in the heart of Osterville, this exceptional Waterfront Estate delivers timeless beauty and relaxed elegance. Wake each morning to sweeping water views and ocean breezes, step onto your boat from the Substantial Dock. Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence is thoughtfully designed to blend coastal charm with modern comfort, with sun-filled living spaces, expansive windows, and seamless indoor-outdoor flow perfect for entertaining or quiet seaside relaxation. Waterfront Chef's Kitchen with Cathedral Ceiling, Living Rooms, Dens, separate living quarters complete with a Kitchen over the 3-Bay Garage. Step outside to your private waterfront oasis, where launching a kayak at sunrise, enjoying afternoon boating on North Bay, or taking sunset walks with the dog, every day feels like a vacation. Located just moments from Osterville Village's boutiques, restaurants, and marinas.

46 Great Bay Rd, Barnstable

Listing courtesy of Listing Agent: Chuck Tuttle from Listing Office: William Raveis R.E. & Home Services.

$2,950,000

3 Beds ⋅ 3 Baths ⋅ 73513191 MLS

Located in the heart of Osterville - one of Cape Cod's most desirable seaside villages along Nantucket Sound - 12 Cockachoiset, known as the iconic ''Windmill House,'' offers a distinctive blend of coastal charm and architectural character. Recognized for its unique two-story windmill adorned with seaside murals, the home features a balcony with water views and serves as a memorable focal point of this special property. The main living spaces are designed for comfort and gathering, highlighted by a generous great room with a custom fireplace that opens to a covered patio and private side yard. A well-appointed kitchen adjoins the dining room, while the first floor also includes a bedroom with attached sitting room, laundry, and multiple inviting outdoor living areas. Upstairs, the primary suite is anchored by its own fireplace, private bath, and walk-in closet. An additional sitting room with balcony access and a third bedroom complete the second level, offering flexible space for guests and relaxation. Ideally located just moments from Osterville Village, this property enjoys close proximity to boutiques, dining, and nearby beaches, while also being near some of the area's most renowned marinas, including Nauticus Marina, Crosby Yacht Yard, and Oyster Harbors Marine - offering convenient access to premier boating and waterfront amenities. The adjacent property at 30 Cockachoiset Lane is also available for sale (MLS 22601972). Together, the properties offer a rare opportunity to create a side-by-side coastal compound, with a demonstrated history of significantly strong, high-value rentals and private gatherings. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

12 Cockachoiset Lane, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$1,500,000

3 Beds ⋅ 2 Baths ⋅ 73504595 MLS

A mid-19th-century Greek Revival, believed to be the birthplace of Captain William Bradford Parker and later home to Samuel Hallett — both tied to Osterville's historic maritime corridor along Main Street. The property reflects the success of maritime captains - there's a reason Osterville was once described as "a place where retired sea captains can live like gentlemen." You feel that here. The primary bedroom has been expanded to include a quiet alcove with a gas stove, an easy place to settle in on cooler days. The yard comes alive in season with mature plantings and a sense that it's been thoughtfully cared for. And it has — by the same owners since 1989. A short walk to quaint Osterville village, and a short drive to Dowses Beach and Joshua Pond for summer fun. Newer windows, original wide pine floors, 2 gas fireplaces, updated electrical, and a new gas heating system are already in place.A history worth inheriting and the charm from a more gracious era. This one needs to be seen.

955 Main Street, Barnstable

Listing courtesy of Listing Agent: Karen D. Lilly from Listing Office: Property Cape Cod.

$775,000

2 Beds ⋅ 2 Baths ⋅ 73503938 MLS

Osterville opportunity. Situated on 1.4 acres and abutting conservation land, this 2-bedroom, 2-bath raised ranch offers endless possibilities. Located just moments from Osterville’s charming village center, you’ll enjoy easy access to boutique shopping, delightful dining, and local favorite, Dowses Beach. Whether it’s a thoughtful home renovation or a complete reimagining to unlock the full potential, this property invites you to create something special

441 Old Mill Rd, Barnstable

Listing courtesy of Listing Agent: Diane Boudreau from Listing Office: Kinlin Grover Compass.

$8,995,000

5 Beds ⋅ 6 Baths ⋅ 73441700 MLS

Nestled amid beautifully landscaped grounds, this exceptional 7,500± square foot residence captures breathtaking views over West Bay and Eel River. A private sandy beach and deep-water dock provide effortless access to Nantucket Sound, creating a rare combination of serenity and seafaring adventure. Inside, the five-bedroom home blends refined architecture with inviting coastal warmth. A dramatic two-story great room opens to an expanse of windows that frame the water, seamlessly connecting the interior to the surrounding natural beauty. The thoughtfully designed main level includes a chef's kitchen adjoining a sun-filled sitting room, elegant dining room, gracious living room, and handsome home office. The first-floor primary suite offers a peaceful retreat with water views, while a second primary suite and three additional bedrooms complete the upper level. A captivating tower room provides a 360-degree vantage point for enjoying sweeping sunsets and the ever-changing coastal landscape. The finished lower level extends the living space with a recreation area, wet bar, and kitchenette, ideal for casual gatherings or guest overflow. A two-car garage, expansive outdoor terrace and lush gardens complement the home's elegant yet relaxed design. Privately positioned, yet moments from Osterville's charming village center, this remarkable estate epitomizes luxurious waterfront living on Cape Cod. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

168 Garrison Ln, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

$9,950,000

6 Beds ⋅ 9 Baths ⋅ 73285680 MLS

Discover the epitome of luxury living in this custom-designed waterfront estate, featuring breathtaking views of Eel River and Nantucket Sound. Located in the village of Osterville and set on an expansive and beautifully landscaped 2.4-acre lot, this stunning residence features over 8,000 square feet of meticulously crafted living space with rich details, modern comforts and extraordinary views. The grand interiors seamlessly blend with the exquisitely landscaped outdoor spaces, featuring an inground pool, hot tub, spacious pool house, and a substantial private deep-water dock. Upon entering the home, the grand foyer leads you into the magnificent great room with a two-story custom fireplace, where panoramic vistas of the water and breathtaking sunsets set the scene for unforgettable family gatherings as well as effortless entertaining. The generous floor plan also features a refined library, formal dining room, a gourmet kitchen with center island, custom cabinetry and top-of-the-line appliances and a state-of-the-art home theatre. The six en-suite bedrooms include a first-floor suite with French doors leading to the back yard and a lavish primary suite with a luxurious bathroom, two walk-in closets and a private deck overlooking the water. Enhanced with modern conveniences such as a Sonos whole-house sound system and a 9-zone Hydro air system, every detail has been carefully planned and implemented. Additional highlights include a private guest suite above the attached 3-car garage and a sprawling entertainment room with a balcony on the third level highlighted by western exposure to experience breathtaking sunsets. Located just minutes from the upscale boutiques and renowned dining of Osterville village, this extraordinary property offers a lifestyle of unparalleled elegance and tranquility by the sea. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

501 Eel River Rd, Barnstable

Listing courtesy of Listing Agent: Robert Kinlin from Listing Office: .

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