366 houses for sale in Osterville

Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coastal luxury with this magnificent Cape Cod waterfront estate, nestled in the prestigious gated community of Oyster Harbors. Boasting 450 feet of pristine water frontage with a private beach and breathtaking views over Cotuit Bay and North Bay, this property offers spectacular sunsets, an elegant coastal lifestyle, and unparalleled privacy. Stepping into the grand foyer, you are greeted by vaulted ceilings and expansive windows that showcase panoramic water views, seamlessly blending the outdoors with the refined interiors. The open-concept living spaces include a gracious living room, a fireplace-warmed dining room with custom built-ins, and a sophisticated sitting area, all designed for effortless entertaining. A private home library, accessed by a spiral staircase, overlooks both the main level and the serene waters of North Bay. The gourmet chef's kitchen is a masterpiece, featuring a granite cent

Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends timeless coastal elegance with modern luxury. Designed for both everyday living and entertaining, the home offers sun-filled interiors with vaulted ceilings and rich hardwood floors. Formal living and dining rooms provide inviting gathering spaces with serene backyard views. At the heart of the home, the chef's kitchen features custom wood cabinetry, granite countertops, a large center island, and premium Wolf and Sub-Zero appliances. An adjacent breakfast nook enhances the kitchen's functionality, with direct access to the family room and screened porch for seamless indoor-outdoor living. The primary suite offers a private retreat with dual walk-in closets, patio access, and a spa-like bath with soaking tub and walk-in shower. Additional bedrooms, en-suite baths, and a home office add flexibility. A finished lower level includes a gym, office, wine cellar, and ample storage. Outdoors, a brick patio and stone wall

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

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!

Ideally situated for an easy walk to Osterville Village and Dowses beach, this home is perfectly positioned to enjoy everything the area has to offer. Including walking, biking, and golf. Every detail reflects intentional craftsmanship, from the custom kitchen cabinetry to the elegant wainscotting, intricate moldings, and soaring cathedral ceilings that give the home a sense of grandeur without sacrificing warmth. As soon as you enter from the front porch, you will gaze right out to the backyard. The home is flooded with natural sunlight. You'll find high-end appliances, including 3 Wolf ovens, a Sub-Zero refrigerator, an oversized butler's pantry, and a dining room made for large family gatherings and holiday celebrations. Retreat into the first-floor primary sanctuary, with spa-inspired en-suite and a large walk-in closet. From the front and three-season porches to private sleeping areas, a family room, and a basement entertainment space, this home has room for everyone to spread out

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 accommod

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!

Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds designed for both grand entertaining and quiet moments of retreat. Inspired by the timeless character of a European country estate, the residence encompasses 7,157 square feet of thoughtfully designed living space where sophisticated craftsmanship meets effortless comfort. A dramatic foyer introduces the home's remarkable interior, opening to an impressive great room with soaring vaulted ceilings, architectural columns, a custom fireplace, and expansive walls of glass that frame the ever-changing waterfront. Designed for both everyday living and elegant entertaining, the sun-filled dining room cap

In the heart of Wianno. One-level living where it counts. This 4-bed, 3.5-bath Osterville home sits in one of the Cape's most walkable, sought-after locations, moments from Dowses Beach and Main Street's shops and restaurants. Inside, it lives like new: gleaming hardwood floors, crown molding, and detailed wainscoting throughout. The first-floor primary suite means single-level living without giving up scale. A fireplace anchors the open living area, built for both quiet nights and full-house gatherings. The kitchen carries the same finish level throughout the whole home, with high-end appliances and detailed cabinetry designed for real entertaining, not just photos. Outside, the bluestone patio functions as a second living room: a pergola, built-in gas grill, and custom gas fire pit make three-season (and beyond) living effortless. Practical luxury runs underneath it all. Geothermal heating and cooling keep utility costs down year-round, and the attached heated garage adds protected p

Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds designed for both grand entertaining and quiet moments of retreat. Inspired by the timeless character of a European country estate, the residence encompasses 7,157 square feet of thoughtfully designed living space where sophisticated craftsmanship meets effortless comfort. A dramatic foyer introduces the home's remarkable interior, opening to an impressive great room with soaring vaulted ceilings, architectural columns, a custom fireplace, and expansive walls of glass that frame the ever-changing waterfront. Designed for both everyday living and elegant entertaining, the sun-filled dining room cap

This beautiful new Osterville home is perfectly situated in Wianno, just minutes from village shops, restaurants, and Dowses Beach. With its open floor plan, white oak hardwood floors, and exceptional attention to detail, this charming property offers coastal living at its finest. The stunning kitchen features quartzite countertops, Viking appliances, and a large island with generous seating and ample workspace. A cheerful dining area anchors the space, complemented by a separate bar with glass-front cabinetry-ideal for entertaining and additional storage. A light-filled sitting area, first-floor primary suite, private office, and separate laundry room complete the main level. A graceful open staircase leads to the second floor, where you'll find a spacious family room and two additional bedrooms; a second primary ensuite, and a bunk room with its own full bath. Outside, a bluestone deck, putting green and outdoor shower add fun activities for warm days! Please note the furnished rooms

In the heart of Wianno. One-level living where it counts. This 4-bed, 3.5-bath Osterville home sits in one of the Cape's most walkable, sought-after locations, moments from Dowses Beach and Main Street's shops and restaurants. Inside, it lives like new: gleaming hardwood floors, crown molding, and detailed wainscoting throughout. The first-floor primary suite means single-level living without giving up scale. A fireplace anchors the open living area, built for both quiet nights and full-house gatherings. The kitchen carries the same finish level throughout the whole home, with high-end appliances and detailed cabinetry designed for real entertaining, not just photos. Outside, the bluestone patio functions as a second living room: a pergola, built-in gas grill, and custom gas fire pit make three-season (and beyond) living effortless. Practical luxury runs underneath it all. Geothermal heating and cooling keep utility costs down year-round, and the attached heated garage adds protected p

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

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

Welcome to this 3 bedroom, 2 bath Cape-style home in the coastal village of Osterville, situated on a corner lot in a neighborhood setting. This property features new kitchen cabinets, new stainless appliances, backsplash and granite countertops. A fireplace living room to enjoy on cool nights and a dining room with sliders to a spacious deck with a gas hookup for grilling, ideal for entertaining your guests. The first-floor primary bedroom and bath provide convenient one-level living, while the walkout lower level offers excellent potential for expansion, a home office or recreation space and includes French doors leading to a brick patio. An attached one-car garage adds storage and convenience. Enjoy the beach, boating, shopping, and dining in this vibrant coastal village. Whether you're seeking a year-round residence, vacation getaway, or Cape Cod retreat, this well-appointed home offers the best of Osterville living

Welcome to this 3 bedroom, 2 bath Cape-style home in the coastal village of Osterville, situated on a corner lot in a neighborhood setting. This property features new kitchen cabinets, new stainless appliances, backsplash and granite countertops. A fireplace living room to enjoy on cool nights and a dining room with sliders to a spacious deck with a gas hookup for grilling, ideal for entertaining your guests. The first-floor primary bedroom and bath provide convenient one-level living, while the walkout lower level offers excellent potential for expansion, a home office or recreation space and includes French doors leading to a brick patio. An attached one-car garage adds storage and convenience. Enjoy the beach, boating, shopping, and dining in this vibrant coastal village. Whether you're seeking a year-round residence, vacation getaway, or Cape Cod retreat, this well-appointed home offers the best of Osterville living

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

New spacious front yard and entrance redesigned! Fall in love the moment you step inside this beautifully renovated home that feels brand new in every way. Sunlight fills the space throughout the day, drawing your eye to tranquil pond views and the surrounding natural beauty that create an immediate sense of calm and privacy. Thoughtfully redesigned with modern amenities, this home offers effortless living both indoors and out. Imagine preparing meals in the outdoor kitchen while overlooking the water, or starting your day in the main-level bedroom with peaceful pond views before stepping onto the deck with your morning coffee. Tucked into a serene setting, yet just minutes to the boutiques, restaurants, coffee shops, and ice cream spots of Osterville Village. Enjoy easy access to all of Barnstable's beautiful beaches, with iconic Dowses Beach only minutes away. A private retreat that perfectly blends nature, comfort, and location. Note: Town Field Card does not reflect renovation upda

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, (complete with 30 Amp power outlets and fresh water). 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, r

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

Oh 7/12 cancelled*. Location, lifestyle, and flexibility come together in this oversized Cape offering 7 rooms, 3 bedrooms, and 2 full baths, currently utilized as a 4-bedroom home. Choose between a spacious first-floor or second-floor primary bedroom to suit your needs. Outside, the large level backyard offers plenty of space for entertaining, gardening, or simply relaxing, while two driveways provide ample parking for family and guests. Enjoy easy access to some of the area's most popular destinations. Dowses Beach and Craigville Beach are both just 10 minutes away, while Joshua's Pond is only a 7-minute walk or 2-minute drive from your doorstep. This freshwater pond is a local favorite for swimming, kayaking, paddleboarding, and enjoying the natural beauty of Cape Cod. Just 3 minutes by car or approximately 20 minutes on foot, Osterville Village offers a charming collection of local shops, restaurants, cafes, and everyday conveniences. Whether you're heading to the beach, exploring

Nestled south of Route 28, this charming Osterville ranch offers a perfect blend of classic Cape Cod character & modern comfort. A private front patio welcomes you, providing an ideal spot for a pair of Adirondack chairs. The interior has been thoughtfully reimagined for contemporary living w/ a bright, open-concept layout. Cathedral ceilings, a skylight & sliders leading to a deck create a sun-drenched dining area and an inviting atmosphere. The kitchen features a central island that serves as a natural gathering spot before transitioning into the living room. Anchored by a fireplace, this central living space feels remarkably open & airy. The home includes 2 bedrooms, featuring a primary en-suite with brand-new carpeting flowing throughout. The living space extends to a walkout basement, providing a versatile layout that easily adapts to your specific needs. This lower level opens to a private, level yard, ensuring this Osterville gem is ready for you & its next chapter to begin

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

South of Route 28 in Osterville village, this inviting property offers an outstanding opportunity to secure your place in one of the area’s most desirable locations. Just 1 mile from Main Street, enjoy easy access to restaurants, shops, beaches, and everyday conveniences that make village living so special. Inside, the home features a bright living room with vaulted ceilings, a first-floor bedroom and full bathroom, plus an attached one-car garage. The existing layout provides comfortable living space, making the property well suited for both year-round and seasonal ownership. Outside, you’ll find a fully fenced backyard and a spacious deck. The property is included in the town sewer expansion, with connection anticipated around 2028 following completion of construction. Access to town sewer is a valuable benefit, offering added peace of mind and flexibility for future renovation or expansion

Nestled in a neighborhood south of Route 28, this charming Osterville ranch offers the perfect blend of classic Cape Cod character & modern comfort. Before you even step inside, a private front patio welcomes you, the ideal spot for a pair of Adirondack chairs. The interior has been thoughtfully reimagined for contemporary living w/ a bright open concept layout. Upon entry, you're greeted by a sun-drenched dining area that sets an inviting tone w/ its cathedral ceilings, a skylight & sliders that lead out to a freshly painted deck. The kitchen offers a central island providing a natural gathering spot before transitioning into the living room. Anchored by a fireplace this central living space feels remarkably open & airy. The home features 2 bedrooms, including a primary en-suite. Brand-new carpeting flows throughout the entire home, paired w/ an abundance of storage space to keep everything perfectly organized. The living space extends to a walkout basement, providing a versatile layo