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 sold turn key ready for you to enjoy!
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 can be sold turn key or as a empty palette 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: Capital Realty Enterprises Inc
508-566-0350
Welcome to your peaceful Osterville retreat. The home features an open concept floor plan with chef's kitchen that flows seamlessly into the living room and dining area. The living room has a gas fireplace and beautiful cathedral ceiling. There are two bedrooms on the the main level with the primary ensuite featuring a new luxury walk in shower. Additional amenities include first floor laundry. Enjoy your morning coffee while viewing the tranquil back yard from your enclosed three season porch. As an added bonus this home features a finished lower level with kitchenette and large spacious rooms with another full bath. Relax outside on the new paver patio . The lower level has separate access allowing for a multitude of ways to utilize this space. The back yard offers a gardeners dream with large garden shed. Enjoy the outdoor shower after returning from nearby Dows Beach. This home is staged by Habitat for Humanity with all new furniture that may be purchased by buyer. Located on a quiet cul-de-sac with close proximity to Cape Cod Mall, schools, and golf. Enjoy the flavor of many of the near by restaurants. Truly a must see property. Lower level not included in finished space.
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.
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.
Courtesy: SilverStone Capeside Realty Group
774-271-1844
Nestled near downtown Osterville with picturesque views and access to West Bay, this inviting home offers the perfect blend of location, charm, and opportunity. Tucked away on a private lane, this 3-bedroom, 3 full bath property presents a rare chance to own in one of Osterville's most sought-after areas. Set on a generous 0.87-acre lot, the home feels like your own private Cape Cod retreat. This beautiful property includes a footpath (easement) to West Bay to enjoy gorgeous sunsets all summer long. Inside, you'll find timeless character throughout, including wide pine floors, custom built-ins, and a warm, nostalgic ambiance that captures the essence of classic Cape living. There is an attached oversized 2-car garage with an additional storage space for your kayaks and canoes. Whether you're looking to enjoy it as-is or bring your vision to life, this property is full of possibilities in an unbeatable setting.
Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties
508-420-1414
Welcome to a rare offering at the coveted The Cove at East Bay--an impeccably updated luxury condominium designed for effortless Cape Cod living. Sunlight fills the interior, while expansive living spaces, a chef's kitchen, custom woodwork, and refined finishes create an elegant yet inviting retreat for family and guests alike. In close proximity to the beach and village, this exceptional residence pairs sophisticated comfort with an unmatched Ostervillelifestyle.
Just minutes from downtown Osterville Village and Dowses Beach, making this home the perfect location. From the moment you arrive at the home, you're greeted with a stone circular driveway and a large front porch that says "Welcome, please come in!" Once inside, you can immediately see the timeliness elegance, yet the comfort needed for everyday living. All rooms are the perfect size and the layout and flow from one room to the next, makes this home absolutely ideal for family living. Although 3-bedrooms, there's a "Bonus Room" for weekend guests. Every room in the home is filled with natural sunlight, including the kitchen with 8 large windows providing a lovely few of the fruit trees and gardens. Have your morning coffee on the front porch and your early evening refreshments on your back patio while you look at the hydrangea trees, bushes and perennial gardens. Add a pool, pool house and a tennis court, if you would like, as the yard is large enough to accommodate.
Charming 3-bedroom, 1-bath home on a spacious 0.64-acre lot in one of Osterville's most desirable locations. Features include a sunroom, garage, additional shed, private backyard, and newer boiler, gas furnace and heat pump.Conveniently located near Dowses and Craigville Beaches and close to Osterville Main Street shops and restaurants. A wonderful opportunity for year-round living, vacation, or investment (strong potential for renovation, expansion, or rental income)Excellent opportunity in a high-demand area.
Located in the desirable Wianno in Osterville surrounded by Luxurious homes, and walking distance to Wianno Golf course. This home has plenty of space for a large family or someone who likes to entertain. Home has three separate wings for privacy. Some of the recent improvements include kitchen with open concept. Kitchen has two stainless refrigerators and two dishwashers. Quartz countertops, and updated bathrooms. Home is great for entertaining with outdoor kitchen, Gunite pool with hot tub, and fire pit for those cool summer nights. Property is currently used for a vacation rental, so check for showing availability. Rents for $3000 per day.
Courtesy: Frank A Sullivan Real Estate
508-428-4400
A generational waterfront setting on Crystal Lake with approved Patrick Ahearn plans and a privately owned dock - an exceptionally rare, build-ready opportunity within a stone's throw of Osterville beaches and village center.A truly distinctive offering on the shores of Crystal Lake in one of Osterville's most coveted and tightly held neighborhoods. With direct lake frontage, a privately owned dock, and approved architectural plans by Patrick Ahearn, one of New England's most celebrated residential architects, this is a rare opportunity to create a refined waterfront residence with both architectural pedigree and long-term value.Ideally positioned for the best of Osterville living, the property offers the uncommon luxury of easy access to the Wianno/Sea View Beach (.2 mi), Dowses Beach (.3 mi), and Osterville Village (.8 mi), placing iconic beaches, village amenities, and daily conveniences all within easy reach. The combination of waterfront privacy and exceptional proximity is increasingly rare in today's market.Offered at $8.75M, the package includes the land and a clearly defined construction package with Sea View Builders, based on the approved architectural plans for th the main residence. Buyers may customize layout, square footage, and interior finishes prior to construction, allowing for meaningful personalization while preserving the integrity of an Ahearn-designed waterfront home. The property also benefits from septic capacity for up to 11 bedrooms, providing additional flexibility for future design beyond the proposed plan. Designed to embrace its Crystal Lake setting, the home is planned to capture tranquil water views and a strong indoor-outdoor connection, with a gunite PebbleTec pool included as part of the offering package. Additional amenities, including a carriage house, cabana, and expanded outdoor living and entertaining spaces, may be explored separately to suit individual preferences and lifestyle goals. An exceptional opportunity to build an Ahearn-designed waterfront home with a privately owned dock, pool, nearby beaches, and proximity to Osterville Village, offering the very best of Cape Cod living in a truly distinguished setting. *Marketing renderings depict current approvals; package as priced includes the main residence and pool. Final square footage is subject to change based on final plans and end-user specifications.*
Tucked away in the heart of Wianno, this charming waterfront home enjoys exceptional privacy and scenic views of Neck Pond and the Wianno Golf Course.Set on .73 of an acre, this property has been held by the same family for generations and is now ready for its next chapter. Ideally located close to Dowses Beach and shops and restaurants in Osterville village, this home is the perfect Cape Cod get-away with room to reimagine and expand in the future. Enjoy beautiful views and light, bright comfortable rooms in this private 3 bedroom home. This is a special property and a secret spot!
Heart of Wianno! Experience the perfect blend of Cape Cod charm and modern luxury in this beautifully built free-standing cottage-style condo in the sought-after village of Osterville. Enjoy the lifestyle just moments from Wianno Golf Club, sandy saltwater beaches, marinas, the weekly Farmers Market, fine dining, and boutique shopping. The open-concept interior features soaring ceilings, hardwood floors, and a cozy gas fireplace. The chef’s kitchen offers quartz countertops, a Bosch dual-fuel range and dishwasher, and a French-door refrigerator. The primary suite includes a spa-inspired en-suite bath, while the second bedroom has access to a sleek glass-shower bath. Additional highlights include a powder room, sliders to a private brick patio, on-demand Navien hot water, central vacuum, and energy-efficient systems (HERS 53). Pet-friendly with no weight restrictions, offering effortless living in one of Cape Cod’s most desirable coastal villages. Virtually edited exterior photos.
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. Thoughtful decorator touches and Serena & Lily wallpaper bring warmth and personality to every corner of this home.
Set on an oversized 2.94-acre corner parcel in Osterville’s coveted Seapuit neighborhood, this newly built residence offers exceptional privacy, scale, and resort-style amenities just minutes from Osterville Village. Surrounded by established homes, it presents a rare turnkey opportunity in one of Cape Cod’s most desirable communities. The home centers around a dramatic two-story great room with soaring ceilings and a gas fireplace, seamlessly connected to a showpiece chef’s kitchen featuring expansive windows, a generous island, country sink, Viking appliances, and ceiling-height subway tile. A private dining room offers ideal separation for entertaining. The main level includes two en-suite guest bedrooms and a family room, while upstairs features a serene primary suite and an additional guest suite. Outside, the expansive grounds include an in-ground pool, private tennis and pickleball court, mature trees, and a covered porch for relaxed outdoor living.
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%.
