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$4,950,000
5 Beds ⋅ 8 Baths ⋅ 73556306 MLS
Representing the pinnacle of coastal elegance, this extraordinary estate on Little Island offers a rare opportunity for a generational compound in mint condition and an unsurpassed location. Finished to the highest standards, the property features a spectacular five-bedroom main residence, a swimming pool, a pool house with kitchenette and full bath, and a detached three-car garage with a home gym above. In the main residence, timeless and sophisticated design is on display throughout, with custom millwork, designer wallpaper, soaring vaulted ceilings, and a smart home system that governs doors, locks, and hardware with effortless ease. Superlative craftsmanship and finishes define every room, from the chef's kitchen with professional grade appliances to the exquisitely appointed first-floor primary suite featuring custom-designed closets and a luxurious bathroom with a jetted Grohe shower system. Four additional bedrooms, including a second-floor primary suite, ensure refined accommodations for family and guests, while a finished lower level provides flexible bonus space. Set amidst park-like grounds with manicured landscaping, the backyard features multiple gathering spaces, including an expansive poolside terrace with a summer kitchen and fire pit. The stunning pool house caters to resort-style living and offers endless possibilities. Meticulously appointed with no detail overlooked, additional highlights include a whole-home generator, state-of-the-art security, and Lutron smart lighting. Minutes from everything Osterville has to offer, this exceptional family compound is ready to be enjoyed.

313 Bridge Street, Barnstable

Listing courtesy of Listing Agent: Paul E. Grover from Listing Office: .
$1,195,000
2 Beds ⋅ 2 Baths ⋅ 73551581 MLS
Beautifully situated on 0.51 private wooded acres, this peaceful ranch-style 2-bed, 2-bath, 1,418 sq ft home (with an additional 732 sqft of finished basement) blends quiet retreat with everyday convenience. Within a 10-minute walk of the village with shopping and restaurants, Joshua's Pond and beach, and parks, while less than a 10-minute drive from golfing and Dowses Beach. Inside, natural light pours through expansive windows and French doors, illuminating glowing hardwood floors, soaring ceilings, and exposed beams that lend warmth and character. The inviting kitchen features warm wood cabinetry, while spacious bedrooms provide peaceful places to unwind. The newly finished lower level adds 732 sqft of versatile living space. New exterior trim enhances the home. Outside, the private wooded setting surrounds the expansive deck with peaceful views and gentle breezes, creating a secluded escape. A home where nature, light, and timeless charm come together effortlessly. Come view today!

5 Hinckley Circle, Barnstable

Listing courtesy of Listing Agent: Danny Griffin from Listing Office: Griffin Realty Group.
$749,900
3 Beds ⋅ 2 Baths ⋅ 73548407 MLS
Move-in ready and offered for the first time in generations, this charming one-level ranch is ideally located in the heart of Osterville Village. Just 1.5 miles to beautiful Dowses Beach, an 8-minute drive to sought-after Craigville Beach, and only 0.4 miles to the crystal-clear waters of Joshua Pond. This inviting “Cape Cod Escape” features 3 bedrooms and 1.5 baths, offering easy single-floor living. Recent updates include fresh interior paint, beautifully refinished hardwood floors with a fresh stain and polyurethane finish, and a brand-new kitchen floor, making this home ready for its next owner to enjoy from day one. Experience the best of Cape Cod living with charming village shops, restaurants, and coastal attractions just moments away.

84 Hinckley Cir, Barnstable

Listing courtesy of Listing Agent: Chelsea McLaughlin from Listing Office: RE/MAX Legacy.
$1,300,000
3 Beds ⋅ 4 Baths ⋅ 73546631 MLS
Offered for the first time! Radiating curb appeal, this home has been lovingly maintained by the same owners since it was built nearly 50 years ago. Set on a double lot, the landscaping shines in every season! Inside, the welcoming main entry leads to a spacious sitting room with bay window, opening into an elegant dining room. The bright kitchen features a skylight, peninsula and wet bar and opens into the living room with beamed ceilings, fireplace and built-in bookshelf. A highlight of the living space is a sun room with vaulted ceiling and window seat. A separate wing of the main floor has 2 bedrooms, an office and 2 full bathrooms. The main level is rounded out by a third full bathroom and laundry closet. Upstairs, there is a massive 3rd bedroom with full bathroom and its own office. All this in a private neighborhood minutes from Osterville Village. New central AC, Generator, irrigation, a shed, composite deck and two car garage.. come see why this home was worth holding on to

175 Hickory Hill Circle, Barnstable

Listing courtesy of Listing Agent: Michelle Curran from Listing Office: Coastal Real Estate Advisors, LLC.
$4,995,000
5 Beds ⋅ 7 Baths ⋅ 73542127 MLS
Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is positioned seamlessly on a large .52 acre lot with a spacious back yard, a brand new vinyl saltwater pool, outdoor shower, a screened in porch, large patio area, & an outdoor pool cabana w/ a bathroom. This home is perfect for those special summer nights on Cape Cod sitting by the pool and relaxing. Each bedroom includes it's own full bathroom including the 1st floor primary suite bedroom. A few other features added by the builder: a whole house generator, gas fireplace, irrigation system, & a 1-year builder warranty as well. Come see your dream home today before it's too late!

22 Scudder Road, Barnstable

Listing courtesy of Listing Agent: The Quirk Group from Listing Office: Coldwell Banker Realty - Boston.
$1,395,000
4 Beds ⋅ 4 Baths ⋅ 73539620 MLS
Osterville Oasis! Tucked away at the end of a quiet, tree-lined lane, this beautifully renovated Cape-style home offers the perfect blend of classic charm with modern updates in highly desirable Oyster Hills West. The first floor features a spacious Primary Suite with a private bath, overlooking a lushly landscaped, private backyard. The inviting Living Room showcases custom built-ins and a striking Gas Fireplace, flowing seamlessly into a lovely Porch-an ideal spot to enjoy morning coffee while taking in the peaceful surroundings. The oversized dining area highlights upgraded Andersen windows installed throughout the home in 2019, bringing abundant natural light. A renovated Granite Kitchen, 1st-Floor Laundry, and Powder Room provide complete 1st-floor living potential. Upstairs, you'll find three generously sized Bedrooms, one including an En-Suite half Bath, plus an additional full Bathroom A partially finished Lower Level with two Cedar Closets offers valuable bonus space.Must see!

18 Calico Lane, Barnstable

Listing courtesy of Listing Agent: Chuck Tuttle from Listing Office: William Raveis R.E. & Home Services.
$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.
$649,000
2 Beds ⋅ 2 Baths ⋅ 73513515 MLS
Incredible value at this new price in Osterville Heights! Move right into this sun-filled open-concept ranch with one-car garage and oversized shed, a private and spacious partially-fenced backyard with its park-like setting is perfect for adding a potential pool, enjoying outdoor games, barbecues, and relaxing with family and friends. New improvements include enhanced landscaping, fresh paint, Canadian white oak flooring throughout, three Rovsun mini-split A/C units, tile floors in both bathrooms, an Electrolux non-venting stackable washer/dryer in hallway full bath, vanity/toilet in second bedroom bath, and an electric heated fireplace in large bedroom. The full lower level as well as the generous backyard provides more options for additional living space. Perfectly suited as a year-round residence, vacation getaway or investment opportunity. Ideally located just minutes from Osterville Village, Dowses Beach, golf, boating, shopping, dining and many other premier local amenities!

55 Seth Goodspeed's Way, Barnstable

Listing courtesy of Listing Agent: Donna Christopher from Listing Office: Sotheby's International Realty.
$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: .
$1,850,000
3 Beds ⋅ 3 Baths ⋅ 73512219 MLS
This elegant Cape-style residence offers a refined retreat on a sprawling, wooded lot near Osterville Village and Dowses Beach. Defined by bright, voluminous spaces, the home features a stately pillared portico, stone walkways, and classic shingle siding. Inside, the center hall layout leads to a grand living room with a two-story wall of windows and a Palladian arch. This flows into the dining room and a kitchen equipped with granite countertops, a cooktop island, and a sunny breakfast nook. The adjacent family room features custom built-ins and a brick fireplace. The first-flow primary suite serves as a sanctuary with a walk-in closet and en suite bathroom. Upstairs, a mezzanine gallery overlooks the living area, leading to two spacious guest bedrooms. Outside, an expansive rear deck with a vine-covered pergola overlooks the private lawn and an ornamental pond, creating the perfect setting for relaxation. Located minutes from everything Osterville has to offer!

81 Osterville-West Barnstable Rd, Barnstable

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

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