Charming one-level ranch offered for the first time in generations, ideally located in the heart of Osterville Village. Only 1.5 miles to beautiful Dowses Beach, a short 8 minute drive to sought-after Craigville Beach, and a quick 0.4 miles to the clear waters of Joshua Pond. This inviting "Cape Cod Escape" features 3 bedrooms and 1.5 baths, offering easy single-floor living and endless potential. Freshly uncovered hardwood floors are ready to be finished and restored to their original beauty. A rare opportunity to update and make it your own in a prime location. Enjoy village shops, dining, and coastal charm nearby—create lasting Cape Cod memories here!
In the heart of Wianno, surrounded by Osterville’s iconic multi-million-dollar estates, this newly built 2023 free-standing golf villa offers effortless luxury and carefree Cape Cod living. Just moments to Wianno Golf Club, Dowses Beach, marinas, boutique shopping, acclaimed dining, and the Osterville Farmers Market, the location is exceptional. The light-filled interior features soaring ceilings, wide-plank hardwood floors, and an open layout anchored by a gas fireplace. The designer kitchen showcases quartz countertops, Bosch dual-fuel appliances, and custom finishes. The primary suite offers a spa-like bath, while guests enjoy a private en-suite-style retreat. Sliders open to a charming brick patio perfect for summer evenings after golf, boating, or beach days. Additional highlights include a powder room, Navien on-demand hot water, central vacuum, HERS 53 energy rating, and pet-friendly living with no weight restrictions. Turnkey Osterville living at its best.
Just in time for summer! Move right into this newly remodeled, sun-filled open-concept ranch with one-car garage and oversized shed in desirable Osterville Heights! Set on a spacious, partially fenced private yard, it's perfect for outdoor games, barbecues, and relaxing with family and friends. Recent upgrades include enhanced landscaping, fresh paint, Canadian white oak flooring throughout, three Rovsun mini-split A/C units, new tile floor and Electrolux non-venting stackable washer/dryer in hallway full bath, new tile and vanity/toilet in second bedroom bath, and new closet and electric heated fireplace in newly-expanded large bedroom. The full lower level offers excellent potential for additional living space. Perfectly suited as a year-round residence or an idyllic Cape Cod retreat! Ideally located just minutes from Osterville Village, Dowses Beach, and a variety of 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.
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!
Discover the charm of this lovingly maintained ranch-style home, just minutes from Osterville Village's coastal Main Street with its boutiques, cafes, and seaside allure. The inviting foyer sets the tone for a warm, welcoming, and flexible floorplan. The living room, with French doors, can double as a den, office, or guest space. The family room, featuring an inviting gas fireplace, flows seamlessly into the dining area and the kitchen, designed with the golden triangle for effortless cooking. French doors lead to a spacious, sunlit, year-round sunroom, perfect for relaxation and entertaining. The primary bedroom boasts an ensuite bath, while a second bedroom, 2.5 baths, and an outdoor shower enhance comfort. Storage abounds with numerous closets, an expansive basement, an oversized two-car garage, and a shed. This home, with gas heat and central air, offers quintessential Cape Cod living with one-level ease. Make it yours! Please verify all information herein.
This 4 bedroom home, nestled in one of Osterville's most coveted neighborhoods, is perfect for both relaxation and entertaining. 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 eaches, this property embodies the very best of Cape Cod living.
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.
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. Pictures show virtual staging.
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. history worth inheriting and the charm from a more gracious era. This one needs to be seen.
A custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Crosby Boat Yard, Nauticus Marina, Oyster Harbors Marina, The Chart Room and well-known West Bay, you will find this top of line crafted 4 bedroom, 3.5 bathroom home. Hand-selected flooring and natural lighting fill the open-concept entertaining spaces and private rooms, creating an elevated living experience. Note-worthy features include a bright open-concept with tall ceilings and a vaulted living room, custom kitchen with chef's pantry, two separate en-suites, private home office, loft space for overflow, front porch, deck with automatic awning, a one car garage and a brand new inground pool with a wrap around stone patio. This home provides a haven for those looking to live life by the sea without relinquishing the convenience of access to Wianno Golf Club, Main Street shopping, plenty of dining options and the beautiful oceanside beaches. Can be yours for summer!
Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties
508-420-1414
A custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Crosby Boat Yard, Nauticus Marina, Oyster Harbors Marina, The Chart Room and well-known West Bay, you will find this top of line crafted 4 bedroom, 3.5 bathroom home. Hand-selected flooring and natural lighting fill the open-concept entertaining spaces and private rooms, creating an elevated living experience. Note-worthy features include a bright open-concept with tall ceilings and a vaulted living room, custom kitchen with chef's pantry, two separate en-suites, private home office, loft space for overflow, front porch, deck with automatic awning, a one car garage and a brand new inground pool with a wrap around stone patio. This home provides a haven for those looking to live life by the sea without relinquishing the convenience of access to Wianno Golf Club, Main Street shopping, plenty of dining options and the beautiful oceanside beaches. The home is ready for you to furnish with your own touches...the perfect Cape home you have been searching for!
Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends coastal elegance with modern luxury. Sunlit interiors feature vaulted ceilings, hardwood floors, and inviting living and dining spaces overlooking a private backyard. The chef’s kitchen offers custom cabinetry, granite countertops, a large island, and premium Wolf and Sub-Zero appliances, opening to a family room and screened porch for seamless indoor-outdoor living.The primary suite is a serene 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 provide comfort and flexibility.A finished lower level includes a gym, office, and storage. Outdoors, a brick patio and stone wall frame a yard with room for a pool. Expansion potential is already in place for a second floor with 10-foot ceilings, offering a rare opportunity to grow within Oyster Harbors.
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
Courtesy: Craigville Realty Co
508-775-3174
RARE opportunity for a gorgeous first floor unit in Osterville's desirable Village Square. Completely renovated and move in ready two bedroom two bath condo in the heart of Osterville village. Light and airy open floor plan with numerous windows and ample natural light. Features include all new kitchen with luxury appliances, gorgeous marble and natural stone tiled bathrooms, white oak flooring, walk in laundry room, additional storage area and private bluestone covered patio surrounded by impeccable, lush and beautiful landscaping. Be in by Summer, won't last!
Courtesy: Gibson Sotheby's International Realty
508-945-0000
Welcome to Osterville Living at Its Finest.Built in 2018 by the esteemed Barnstable Harbor Builders, this impeccably crafted 3-bedroom, 2.5-bath home offers the rare combination of quality new construction feel with the warmth of a lovingly maintained retreat. Used lightly on a seasonal basis, every room feels fresh, pristine and move-in ready because It Is! Step inside and discover thoughtfully designed living spaces where craftsmanship is evident in every detail, from the trim work to the finishes, nothing has been overlooked. The open layout flows naturally for both quiet evenings and easy entertaining inside and out, it offers the comfort and space your lifestyle deserves. Ideally situated just minutes from Cape Cod Academy and the charming boutique shops, restaurants of downtown Osterville, this home places the very best of the Cape at your doorstep. Whether you're dreaming of a full-time residence or an elevated seasonal escape, this property delivers without compromise. No waiting, no projects, no worries just pack your bags and start living the Osterville life. Your Cape Cod story starts here.
Set on 3.4 acres of meticulously landscaped grounds in Osterville's coveted Seapuit neighborhood, this magnificent Colonial estate offers the best of modern living. The 5-bedroom residence showcases architectural splendor and attention to detail throughout, with expansive outdoor living spaces. The grounds boast rolling lawns, a sports court, a swimming pool, and a poolside guest house with a kitchenette and 2 bedrooms. On the main level of the home, an eat-in chef's kitchen opens to a great room with a stone fireplace and glass doors that connect to the pool area. The first-floor primary suite enjoys a sumptuous bathroom and access to a private patio overlooking the gardens. On the second level, 4 well-appointed guest bedrooms provide refined accommodations for family and guests, with additional bonus space. Ideal for the car collector, the home is equipped with an attached 3-car garage and a drive-in lower level. Located minutes from everything Osterville has to offer.
This beautifully updated Osterville Cape, set on a private cul-de-sac, offers move-in-ready living with a thoughtfully curated interior that reflects its coastal charm. Bright, spacious rooms feature vaulted ceilings, skylights, and abundant natural light, while five high-efficiency ductless A/C units ensure comfort throughout the summer months.The first-floor primary suite includes a walk-in closet and a private bath with laundry. Designed for effortless entertaining, the open floor plan seamlessly connects the kitchen, living room with gas fireplace, family room, and dining area, with patio doors leading directly to the backyard.Set on a professionally landscaped half-acre lot, the outdoor space provides privacy and a stunning Trex deck and stone patio. Create the perfect setting for summer gatherings, morning coffee, or relaxing evenings after the beach.The 2nd level offers two bright bedrooms, a full bath with skylight, and a spacious bonus room with heating and air co
“Point House”, a rare 5.98-acre waterfront estate set on a private peninsula overlooking West Bay. This exceptional offering features sweeping water views, a private sandy beach, and a deep-water dock with direct access to Nantucket Sound. The nearly 5,000 sq ft home offers six bedrooms, refined architectural details, and five fireplaces. Designed to embrace its setting, the home opens to a full deck with seamless indoor-outdoor living. A dramatic two-story great room with fireplace anchors the home with the well-appointed kitchen, dining area, and family room—ideal for both everyday living and entertaining. The first level includes two bedrooms and a private sitting room, while the second floor is anchored by a serene primary suite with water views, spacious bath, walk-in closet, and fireside sitting room. Three additional bedrooms and a sitting area complete this level while a third-floor tower captures unforgettable sunsets. Guest quarters above a two-car garage add flexibility.
Courtesy: Compass Massachusetts, LLC
508-206-8726
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. Outside, the landscaping truly shines -- spectacular hydrangeas in bloom, a beautiful maple tree out front, a stone firepit, and an outdoor shower round out this exceptional property.
Summer is in the Air! Welcome 177 Bayview Circle and Osterville Village. Enjoy sunbathing and swimming at Dowses beach, go clamming off Bridge Street, stroll to Fancy's Market and Main St for dining, shopping, ice cream and more. This lovely property is also near town way to water, Osterville Library and Post Office, Crosby Yacht, East Bay, the farmers market and private golf clubs. Come see this 3-bedroom, 3 bath Cape with hardwood floors, an eat in kitchen, first floor primary with bath and private deck, large, bright, heated sunroom, first floor laundry and finished lower level with an additional 600 sq feet with a walk out basement. Some improvements include a freshly painted interior, newer windows, a whole house generator, new interior doors and light fixtures. The private, spacious .40-acre lot has an outside shower. Ideal for summers, year-round and investment. Sq footage includes lower level with an estimated 600 sq feetExterior photo is a summertime edit
Nestled in the heart of Osterville Village, this 3-bedroom, 3-bath home perfectly blends charm with modern updates in one of Cape Cod's most sought-after locations. The backyard is an entertainer's paradise: just wait until you see this spectacular outdoor kitchen with stainless steel appliances, fire pit, and pergola. A partially finished basement provides extra living space, and an oversized two-car garage with attic storage and a gas generator add convenience and peace of mind. With boutique shopping, dining, and stunning beaches just moments away, this home offers more than just a place to live--it's the Osterville lifestyle.
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.
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%.
