Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties
508-420-1414
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 captures tranquil water views and flows seamlessly into a beautifully appointed chef's kitchen featuring a coffered ceiling, granite countertops, an oversized center island, and direct access to a spacious waterside terrace. The first-floor primary suite offers a luxurious private retreat, while four additional bedrooms--including a gracious guest suite above the attached three-car garage--provide exceptional accommodations for family and guests. Outdoor living is equally compelling. Expansive terraces and inviting gathering spaces overlook the pool, manicured gardens, and deep-water dock, creating an idyllic setting for waterfront entertaining or peaceful afternoons by the shore. Set within one of Cape Cod's most coveted private enclaves, where golf, boating, and an unmatched sense of privacy define the lifestyle, this exceptional estate represents a rare opportunity to own a legacy property in Oyster Harbors.
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.
Location, lifestyle, and flexibility come together in this spacious Cape-style home offering 7 rooms, 3 bedrooms, and 2 full baths, currently utilized as a 4-bedroom home. Choose between a first- or second-floor primary bedroom to suit your needs. The flexible layout is ideal for guests, a home office, or multigenerational living. The large level backyard offers space for entertaining, gardening, or relaxing, while two driveways provide ample parking. 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, offering swimming, kayaking, and paddleboarding. Osterville Village is just 3 minutes by car or a 20-minute walk, with charming shops, restaurants, cafés, and everyday conveniences. A wonderful opportunity to enjoy the Cape Cod lifestyle close to beaches, the village, and outdoor recreation.
Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and romantic patios. Curving stone walls, terraced rock feature gardens, and stone patios complement the entire grounds. Across the river from your 200 feet of waterfront is Long Beach, a pristine barrier stretch of powdery white sand and privacy. The dock enjoys some of the deepest water of any house on this stretch, allowing for multiple boats and other recreational craft. The quaint conclusion to this fairytale setting is a larger detached apartment over the garage. The square footage of 9,011, seven bedrooms and seven-and-a-half bathrooms speak for themselves. This treasure is waiting for you.
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!
Discover your dream coastal retreat in the highly desirable Osterville/Barnstable area of Cape Cod. This stunning home features 3 bedrooms, 2.5 bathrooms, and a spacious layout designed for comfortable living and entertaining. Main level showcases beautiful hardwood flooring, abundant natural light, and a welcoming living room with soaring cathedral ceilings. Spiral staircase leads to the second-floor loft space, along with a second full bathroom and another room/den. Three bedrooms are conveniently located on the first floor, including the primary bedroom with an attached half bath. Full bathroom with tub/shower completes the main level. Outside, enjoy a private wooded yard, outdoor shower, attached garage, and additional parking in the paved driveway. In Barnstable, minutes from beaches, marinas, golf courses, Hyannis shopping and dining, Route 6, Cape Cod Gateway Airport, Dowses Beach, and all the coastal charm that makes Cape Cod one of the most sought-after destinations.
Courtesy: C. Case Realty, LLC
508-868-2105
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 quartz 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.
Delightful first floor unit in sought after Osterville village location! Nestled in the heart of beautiful Osterville village and walking distance to Fancy's Market, Library, Church, Restaurants and Fabulous Boutique shops. Stroll to the resident only desirable Dowses beach too! This is a wonderful opportunity to live and enjoy one floor living where everything is at your fingertips......
Welcome to 7 Bonnie Briar Lane in beautiful Osterville — a charming opportunity tucked within one of Cape Cod’s most sought-after neighborhoods. This inviting 3-bedroom home offers 1,144 square feet of comfortable living space, blending easy coastal living with everyday functionality. Ideally located just moments from pristine beaches, the village center, and local marinas, this property is perfect as a year-round residence or the ideal Cape escape. Central AC and heat are relatively new and there is a brand new water heater...
In Osterville, certain streets make the most of Village living. Starboard Lane, winding along the western shore of the Bumps River, is among the village’s most coveted addresses. Known for gracious homes with exceptional privacy on large parcels, the convenience to the heart of Osterville is a huge plus. 420 Starboard Lane captures the Village vibe wonderfully. Set on 1.68 acres, this four-bedroom 2,636 square foot residence offers an exceptional kitchen, generous gathering spaces, may recent updates, and the flexibility that make for easy coastal living. A detached two-car garage with unfinished space above presents intriguing possibilities for expansion. Private. Prestigious. Perfectly located. A rare chance to claim your place in one of Osterville’s most sought-after enclaves.Opportunity like this rarely lingers.Please verify all information contained herein.
Newly constructed and ready to enjoy, this exceptional waterfront estate on the Bumps River represents the finest of Cape Cod living. Combining an unrivaled setting with state-of-the-art luxury, the property features a resort-like swimming pool and cabana, a boathouse with a float for non-motorized crafts, and a deeded beach lot on Long Beach. The open floor plan seamlessly flows from a fireplaced living room with coffered ceilings to a gourmet kitchen with a Sub-Zero refrigerator, Wolf range, and Danby natural stone counters. Glass doors line the waterside of the home, opening to an expansive Phoenician Buff stone terrace surrounding a Pebble Tec pool and spa. The first-floor primary boasts 2 walk-in closets and a luxurious bath with a freestanding soaking tub. Four en suite bedrooms, a family room, and an ipe deck occupy the second level, with bonus space above. A bedroom suite over the garage accommodates guests or staff. Located minutes from everything Osterville has to offer.
Courtesy: Kinlin Grover Compass
508-362-2120
Nestled within the prestigious enclave of Seapuit, this architectural masterpiece represents a rare synergy of design and craftsmanship spanning over 5,000SF of meticulously curated space. A collaboration between renowned architect Doreve Nicholaeff & the master builders at Sylvia & Sylvia, the residence is an exercise in sophisticated coastal living. The home is set on a two-acre private oasis, featuring manicured grounds in a serene courtyard setting designed by the acclaimed David Hawk. The main level is anchored by a sumptuous primary suite boasting a state-of-the-art bathroom, a dedicated dressing room, and dual walk-in closets. Upstairs, two additional private suites offer refined accommodations for guests or family & the newly finished lower level extends the living space even further. Modern luxury is seamlessly integrated through a recently installed, whole-home Savant automation system, giving you effortless control over climate, lighting, and entertainment at the touch of a button. The heart of Osterville Village & the sands of Dowses Beach are just a few minutes away. This is more than a home; it's a legacy estate offering a lifestyle of unmatched privacy & convenience.
Presenting a rare and extraordinary opportunity on exclusive West Bay. This exquisite waterfront estate features a four-bedroom main residence designed by Hutker Architects to showcase sweeping water views amidst inimitable quality and craftsmanship. Designed as a generational compound, the estate includes a three-bedroom guest house, a swimming pool, sandy beach, an outhaul mooring, and a dock for non-motorized crafts. Throughout the main living space, oversized windows frame breathtaking water views, while understated elegance defines the interiors, with beamed ceilings, wainscoting, and a double-sided stone fireplace. The chef's kitchen features professional-grade appliances, a breakfast bar, and pantry. The first-floor primary suite boasts a covered deck, a large walk-in closet, a private office, and a luxurious bathroom. Located on coveted Eel River Road, this magnificent estate is minutes from Wianno, Oyster Harbors, and the boutique shops and restaurants on Main Street.
Courtesy: Compass Massachusetts, LLC
508-206-8726
Light, bright and located in a quiet neighborhood close to beaches and all that Osterville has to offer is this sparkling ranch. You will love the cathedral ceilings, hardwood floors and open floor plan. The primary is spacious with a great private bath. The lower level is completely finished with three rooms and a full bath. Perfect for overflow, an exercise room and a family room. This house is ideal for entertaining both inside and out with a spacious deck and private back yard. Don't miss this great house that is ready to go! Glare care on all windows. Buyer is encouraged to verify measurements as they are approximate.
Prime location on one of Cape Cod's most coveted roads, East Bay Road in Osterville. This beautiful home is rich with character, having been repurposed from a large carriage house. It boasts history and classic Cape Cod charm. Enter the home through the large living room and move into the kitchen equipped with a bright sunroom off to the right. An old horse stable has been fashioned into an office space that is located to the left of the kitchen, with an adjacent first-floor full bathroom. Upstairs are 4 bedrooms, two are en-suites. Downstairs a finished basement provides more living space and a laundry room and full bath. Outside, a detached 2-car garage provides space for your vehicles and a shed for storage. A beautiful fenced in side yard is ideal for summer gatherings, games or just relaxing. There is also an outdoor area out back for grilling and dining, as well as an outdoor shower, perfect after a day spent at the beach.
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.
Courtesy: Today Real Estate
508-888-8008
Well-maintained 2 bedroom, 1.5 bath ranch with a 1-car garage set on approximately .62 acres. Comfortable one-floor living with a practical layout, spacious yard, and plenty of room to enjoy the outdoors. Whether you're starting out, downsizing, or just looking for an easy-to-maintain home with some land, this property is worth a look. Convenient location with solid upkeep inside and out.
Just in time for summer comes this bright, stylishly updated second-floor condo in a prime Osterville village setting. Thoughtfully renovated with wood floors and an open-concept floorplan, everything you need for effortless seaside living is here. The eat-in kitchen features stone countertops, stainless steel appliances, island and built-in banquette, with French doors opening to a charming Juliet balcony from which you can watch Osterville go by. Off the living areas are the spacious primary with ensuite bath, plus a large guest bedroom and second full bath. Brick fireplace, in-unit laundry closet , parking, plus ample storage. All these complete the easy living package. Seldom do Wianno Knoll residences become available: schedule your private showing today. Buyers and agents please verify all herein.
Nice New Price! Move right into this sweet sun-filled open-concept ranch with one-car garage and oversized shed in desirable Osterville Heights! The 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.
Located in the heart of Osterville, one of Cape Cod’s most sought-after seaside villages along Nantucket Sound, 12 Cockachoiset - known as the iconic “Windmill House” - blends coastal charm with distinctive architectural character. Recognized for its two-story windmill adorned with seaside murals, the home features water views from a private balcony and inviting indoor-outdoor living spaces throughout. The generous great room with custom fireplace opens to a covered patio and private yard, while the kitchen and dining areas are designed for comfortable gathering. The first floor also includes a bedroom suite with sitting room and laundry. Upstairs, the primary suite offers a fireplace, private bath, walk-in closet, and balcony access, alongside an additional bedroom and sitting room. Just moments from Osterville Village, beaches, boutiques, dining, and premier marinas. Adjacent property at 30 Cockachoiset Lane is also available for sale.
Defined by sweeping water views, expansive grounds, and exceptional outdoor living spaces, 30 Cockachoiset (“Dillon House”) offers a welcoming coastal retreat designed for gathering and entertaining. The open-concept main level features a well-equipped kitchen flowing into a sun-filled breakfast nook and sitting area surrounded by walls of windows overlooking the water. Additional highlights include a living room with fireplace, formal dining room with custom built-ins, screened sunroom, and a first-floor primary suite with fireplace, water views, walk-in closet, and spacious bath. Upstairs are three bedrooms, multiple decks with water vistas, and a third-floor bonus room for additional living or guests. A private family room with fireplace and full bath above the primary suite provides ideal guest accommodations. Moments from Osterville Village, beaches, waterfront dining, and premier marinas. Adjacent property at 12 Cockachoiset Lane is also for sale.
Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties
508-420-1414
Defined by its water views, generous grounds, and multiple outdoor living spaces, 30 Cockachoiset (''Dillon House'') offers a welcoming coastal retreat designed for gathering, entertaining, and enjoying life by the water. The main level is thoughtfully designed with an open floor plan anchored by a well-equipped kitchen that flows seamlessly into a sun-filled breakfast nook and sitting area, framed by walls of windows overlooking the water. Additional highlights include a living room with fireplace, formal dining room with custom built-ins, and a screened sunroom that invites indoor-outdoor living. The first-floor primary suite offers a private retreat with its own fireplace, water views, walk-in closet, and a spacious bath. Upstairs, three bedrooms and multiple decks capture water vistas, while a third-floor bonus room provides flexible space for additional living or guests. A separate family room with fireplace and full bath, privately situated above the primary suite, offers an ideal accommodation for extended family or visitors. Ideally situated alongside some of Osterville's premier boating facilities-including Nauticus Marina, Crosby Yacht Yard, and Oyster Harbors Marine-this location is particularly appealing for boating enthusiasts, offering convenient access to full-service docking and care. Just moments from Osterville Village, beaches, and waterfront dining, the property captures the essence of Cape Cod living in a highly sought-after setting. Also available for sale is the abutting property at 12 Cockachoiset Lane (MLS 22601973), presenting a unique opportunity to establish a flexible coastal compound, with a proven track record of premium weekly rentals and hosting memorable private events.
Courtesy: Kinlin Grover Compass
508-362-2120
This 4 bedroom home, nestled in one of Osterville's most coveted neighborhoods, is perfect for both relaxation and entertaining, offering a blend of comfort and space for creating unforgettable memories. The fantastic layout connects the sun-filled living room, kitchen, and dining area, with a slider leading to a deck featuring an awning for shade. There's also a spacious family room with gas fireplace and built-in bar area. The primary bedroom suite boasts a private bathroom and balcony, ideal for unwinding after a long day. A convenient breezeway connects to the garage and allows for extra storage. The fenced-in yard is a true showstopper, featuring a heated pool, a patio perfect for grilling, and a handy shed. With plenty of parking and a voluntary neighborhood association that fosters a strong sense of community, this home is as functional as it is fabulous. Located just minutes from Osterville's vibrant dining and shopping scene, premier golf courses, and the Cape's most stunning beaches, this property embodies the very best of Cape Cod living.
Courtesy: Property Cape Cod
508-420-4200
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 updates, additional sq footage or 3 bedroom count.
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.
Osterville is located in Massachusetts. Osterville 02655 is more family-centric than the surrounding county with 22.82% of the households containing married families with children. The county average for households married with children is 19.97%.
