Osterville Homes for Sale

Welcome to Osterville, a picturesque village nestled within the charming town of Barnstable, Massachusetts. Known for its stunning coastal beauty and rich history, Osterville offers a unique blend of serene living and vibrant community life. With its tree-lined streets, quaint shops, and delightful eateries, this idyllic locale is perfect for those seeking a tranquil retreat while still enjoying easy access to modern amenities.

Osterville is renowned for its beautiful beaches, including the popular Dowses Beach, where residents can bask in the sun, enjoy water sports, or simply take in the breathtaking views of Nantucket Sound. The area is also home to various recreational opportunities, including golf courses, yacht clubs, and scenic parks, making it an outdoor enthusiast’s paradise.

For those considering a move to this enchanting village, you’ll be pleased to discover a diverse array of homes for sale. From charming Cape Cod cottages to luxurious waterfront estates, Osterville’s real estate market caters to a variety of tastes and budgets. Each property is imbued with the character and charm that the region is known for, often featuring stunning architecture, lush gardens, and proximity to the coast.

Living in Osterville means embracing a lifestyle that balances relaxation and community engagement. Whether you’re drawn to its historic charm, natural beauty, or the warm sense of belonging, Osterville is a place where you can truly feel at home. Explore the homes for sale in this delightful village today, and discover the perfect backdrop for your next chapter!

Newest Osterville Homes for Sale

$1,485,000

3 Beds ⋅ 3 Baths ⋅ 73571845 MLS

Beautifully renovated, 23 & 27 Swift Avenue is a rare two-parcel Osterville offering totaling approximately 1.11 acres, moments from Osterville Village. The charming 3-bedroom residence sits on approximately .66 acre and is conveyed with an adjoining approximately .45-acre parcel, creating exceptional privacy and intriguing future potential. Recent improvements include a new roof and brand-new 4-bedroom septic system. Sun-filled interiors feature warm wood floors, classic Cape character and a beautifully appointed kitchen flowing to the dining and family areas. A first-floor primary suite with renovated bath, separate living room and powder room complete the main level, with two bedrooms and full bath upstairs. Outdoors, enjoy expansive lawns, mature landscaping, oversized spa, outdoor shower and stone fire pit. A detached 2-car garage offers temperature/humidity controls and epoxy flooring. Additional parcel offers future possibilities, subject to approvals.

23-27 Swift Ave, Barnstable

$999,000

2 Beds ⋅ 3 Baths ⋅ 73571682 MLS

LIKE-NEW IN OSTERVILLE’S COVETED WIANNO AREA! Rare opportunity to own a free-standing condo/golf villa offering effortless luxury and low-maintenance Cape Cod living. Built in 2023 and lightly lived in, this beautifully appointed home is moments from Osterville Village, Wianno Golf Club, Dowses Beach, marinas, shops and dining. The light-filled interior features soaring ceilings, hardwood floors and a gas fireplace. An oversized gourmet kitchen showcases upgraded countertops, Bosch appliances and custom finishes. Two spacious bedrooms, 2.5 baths, plus separate living and family rooms offer exceptional flexibility. The serene primary suite features a spa-like bath. Large sliders open to an expansive fenced private patio with outdoor shower. HERS 53 energy rating, Navien on-demand hot water and central vacuum complete this Osterville retreat.

16 Second Unit 4, Barnstable

$1,349,900

3 Beds ⋅ 3 Baths ⋅ 73571509 MLS

Set in desirable Osterville, 30 Deerfield Road is a beautifully reimagined three-bedroom, three-bath residence offering effortless coastal living just minutes from the beach. Recently transformed through a comprehensive interior and exterior renovation, the home blends timeless Cape Cod character with fresh, sophisticated finishes and modern comfort. The thoughtfully designed layout is highlighted by a desirable first-floor primary suite, complete with direct access to a private screened-in porch, an inviting retreat for morning coffee or relaxed summer evenings. At the heart of the home, an entirely new kitchen opens to the main living space, with a quartz-topped island and counter seating, an induction range, a beverage fridge, and an unlacquered brass faucet set at a window overlooking the yard. Generous open living and entertaining spaces flow seamlessly to the outdoors, where a spacious deck, paver patio, and classic outdoor shower create the perfect setting for life by the coast. Upstairs, two well-appointed bedrooms are joined by a versatile bonus room, ideal as a guest space or home office, along with a large full bath and a dedicated laundry room. An attached two-car garage and driveway provide ample parking, while the full walkout basement offers extra storage and the potential to be finished in the future for additional space. All of the major systems are new as well, including a natural gas Navien HydroAir boiler with on-demand tankless hot water, brand new central AC, plumbing, and updated 200-amp electrical. Exterior updates include a new asphalt roof, updated siding and trim, and select new windows and doors. With multiple indoor-outdoor living spaces, the home is equally suited for year-round living, weekend escapes, or memorable summers with family and friends. Ideally located just a few minutes from both Dowse's and Craigville beaches and within easy reach of Osterville Village, this turnkey property captures the relaxed elegance and lifestyle that make Cape Cod so special.

30 Deerfield Rd, Barnstable

$1,612,000

3 Beds ⋅ 2 Baths ⋅ 73568233 MLS

**NEW TO THE MARKET**Quaint Cape Cod ranch welcomes you with the covered front porch with contemporary flair located in the heart of Osterville’s historic village coastal neighborhood. This home features an airy open floor plan with cathedral ceilings and recessed lighting throughout. The living room offers a gas fireplace and soaring cathedral ceiling. A vaulted foyer with closet provides an inviting entry. Kitchen highlights include cathedral ceilings, skylight, recessed lighting, oversized pantry, and a center island that opens to the dining area. Sliders lead to the outdoor deck for seamless indoor-outdoor living. First-floor laundry adds convenience. Split floor plan: The private primary bedroom suite is set apart and includes an ensuite bathroom. Two guest bedrooms are located on the opposite side of the home with easy access to a full bathroom. Additional features: full basement offering endless possibilities for storage, expansion, or recreation. Perfectly Situated in Osterville’s desirable coastal community, just a short distance to Dowes Beach and Wianno Golf Course. A wonderful opportunity to enjoy Cape Cod living in one of its most sought-after neighborhoods.

137 Wianno Circle, Barnstable

$18,500,000

7 Beds ⋅ 11 Baths ⋅ 73563501 MLS

Exquisite waterfront estate in the gated enclave of Oyster Harbors, one of Cape Cod's most sought-after communities. Located minutes from everything Osterville has to offer, yet a world apart, the property represents a rare and extraordinary opportunity to own a generational compound in an inimitable setting. Ideally positioned to capture dramatic sunsets over Cotuit Bay and Nantucket Sound beyond, the estate features a stunning main residence, a two-bedroom guest cottage, a swimming pool, private dock, and beach. A wooded drive gives way to manicured grounds of nearly two acres, transporting one to a private seaside resort as the ocean comes into view. Inside, an open layout caters to modern living with an eat-in chef's kitchen equipped with professional-grade appliances, seamlessly blending with a fireplaced living area. Oversized windows and glass doors line the waterside of the home, framing spectacular vistas and effortlessly connecting to the outdoors where a covered wooden deck invites al fresco dining and entertaining. Elevated quality and craftsmanship are found throughout, from rich hardwood floors to custom built-ins and crown moldings.The expansive primary suite encompasses an entire wing of the home with a private balcony overlooking the water, a sumptuous bathroom with a built-in soaking tub, and two walk-in closets. Four well-appointed en suite bedrooms complete the second level, offering refined accommodations for family and friends. Designed to embrace outdoor living, the resort-inspired pool and terrace are the perfect gathering place for summer days, complete with an outdoor kitchen and cabana. A rolling lawn leads to the water, where the private dock offers endless possibilities for days spent on the ocean. Additional highlights include a sports court and a car barn that's sure to please the discerning automotive enthusiast. A rare combination of luxury, privacy, and natural beauty, this one-of-a-kind estate is ready to be enjoyed.

47 Sunset Point, Barnstable

$4,950,000

5 Beds ⋅ 8 Baths ⋅ 73556306 MLS

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

313 Bridge Street, Barnstable

$725,000

3 Beds ⋅ 2 Baths ⋅ 73548407 MLS

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

84 Hinckley Cir, Barnstable

$1,100,000

4 Beds ⋅ 4 Baths ⋅ 73546631 MLS

Price Improvement! Opportunity awaits in this coveted Osterville neighborhood. Bring Your Vision to Life With Over 3300 Sq Ft of Living Space. Radiating curb appeal, this home has been lovingly maintained by the same owners since it was built nearly 50 years ago. Set on a double lot, the mature landscaping shines in every season! New central AC, Generator, irrigation, a shed, composite deck and two car garage. Inside, the welcoming main entry leads to a spacious sitting room with bay window, opening into an elegant dining room. The bright kitchen features a skylight, peninsula and wet bar and opens into the living room with beamed ceilings, fireplace and built-in bookshelf. A highlight of the living space is a sun room with vaulted ceiling and window seat. A separate wing of the main floor has 3 bedrooms and 2 full bathrooms. The main level is rounded out by a third full bathroom and laundry closet. Upstairs, there is a massive private suite with full bathroom and its own office. The dry, unfinished basement has potential for adding extra living space. All this in a private neighborhood minutes from Osterville Village.

175 Hickory Hill Circle, Barnstable

$8,625,000

7 Beds ⋅ 8 Baths ⋅ 73543017 MLS

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.

63 Main Street, Barnstable

$4,795,000

5 Beds ⋅ 7 Baths ⋅ 73542127 MLS

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

22 Scudder Road, Barnstable

$744,000

3 Beds ⋅ 2 Baths ⋅ 73534191 MLS

Welcome to this beautifully updated 3-bedroom, 2-bath Cape-style home in the coastal village of Osterville. Situated on a large corner lot in a neighborhood setting, this property is move-in ready and features a brand-new kitchen, new stainless appliances, backsplash and granite countertops. A fireplace living room for cool nights and a dining room with sliders to a spacious deck ideal for entertaining your guests. The first-floor bedroom and full bath provide convenient one-level living, while the walkout lower level offers potential for expansion, a home office, or recreation space and includes French doors leading to a lovely stone patio area. An attached one car garage adds storage and convenience. Enjoy beach days, 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.

114 King Arthur Dr, Barnstable

$1,995,000

4 Beds ⋅ 3 Baths ⋅ 73531658 MLS

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.

420 Starboard Lane, Barnstable

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