Osterville Real Estate

Welcome to Osterville, a picturesque village nestled in the heart of Barnstable, Massachusetts. Known for its charming coastal atmosphere and rich New England history, Osterville offers a unique blend of serene living and vibrant community life. With its stunning waterfront properties, lush landscapes, and quaint streets lined with boutique shops and delightful eateries, this village is a hidden gem on Cape Cod.

Osterville boasts an array of recreational opportunities, making it the perfect destination for outdoor enthusiasts. Residents and visitors alike can enjoy the pristine beaches, such as Dowses Beach and Joshua’s Pond, where sunbathing, swimming, and picnicking are just a few of the activities that await. The village is also home to the prestigious Wianno Club and the Osterville Historical Museum, which provide a glimpse into the area’s storied past and offer social and cultural experiences for all ages.

The community is renowned for its strong sense of camaraderie, with local events and farmers' markets bringing residents together throughout the year. Families appreciate the top-rated schools and the safe, welcoming environment that Osterville provides.

Whether you’re looking for a seasonal retreat, a year-round residence, or an investment property, Osterville presents an exceptional opportunity to experience the charm of Cape Cod living. With its stunning natural beauty, vibrant community spirit, and a rich tapestry of history, Osterville is more than just a place to live; it’s a lifestyle waiting to be embraced. Discover your dream home in this enchanting village today!

Newest Listings in Osterville

$3,390,000

3 Beds ⋅ 5 Baths ⋅ 73592048 MLS

Set within Osterville's coveted Seapuit neighborhood, this magnificent home combines architectural pedigree with exceptional quality and craftsmanship on a sprawling two acres of park-like grounds. Upon approach, stone entry pillars give way to a winding driveway lined with mature trees and plantings that create total privacy as the residence comes into view. Designed by renowned architect Doreve Nicholaeff and built by Sylvia & Sylvia, the home showcases meticulous attention to detail from the moment one enters the impressive foyer, with its soaring ceilings and an elegant curved staircase. Thoughtfully proportioned living spaces cater to both casual living and grand entertaining, while a state-of-the-art Savant home automation system ensures the utmost comfort and convenience. Oversized windows and French doors line the back of the home, allowing natural light to pour in throughout while providing a seamless connection to a covered wooden deck. The first-floor primary suite encompasses an entire wing of the home with a sumptuous bathroom, two walk-in closets, and direct access to the outdoors.On the second level, two en suite bedrooms enjoy access to a spacious deck overlooking the scenic grounds, offering well-appointed accommodations for all. The finished lower level provides flexible recreational space, configured as a media room and home gym, complete with a full bath. Additional highlights include an attached two-car garage and a four-bedroom septic system. Located minutes from everything Osterville has to offer, this extraordinary estate home is ready to be enjoyed.

140 Seapuit Road, Barnstable

$6,600,000

5 Beds ⋅ 8 Baths ⋅ 73589132 MLS

Architecturally stunning and beautifully appointed, this exceptional residence is set within one of Cape Cod’s premier resort communities. Perfectly sited on 2.44 acres, the elegant home combines exquisite craftsmanship and refined detailing with a warm, inviting sense of style and ambiance. Nearly 5,000 square feet of custom-designed living space flows seamlessly from one room to the next, creating an ideal setting for both sophisticated entertaining and relaxed everyday living. The spacious living room is designed for both grand-scale entertaining and comfortable everyday living, featuring a handsome wet bar and seamless access to the light-filled sunroom overlooking the resort style pool. The dining area provides an inviting setting for formal gatherings, while the beautifully appointed kitchen with a generous center island, granite countertops, and custom backsplash, serves as the heart of the home. Refined millwork and thoughtful architectural details throughout add a timeless sense of elegance. The luxurious primary suite offers a spa-inspired bath, private sitting area, and separate office. The second-floor features three en-suite bedrooms, complemented by a fourth en-suite bedroom with a private balcony above the two-car garage. The outdoor setting is a defining feature of the property. A striking in-ground pool, pool house, fire pit, and beautifully designed landscaping create an inviting backdrop for summer entertaining and relaxed afternoons at home. Multiple outdoor spaces are framed by the grounds, while the long driveway and substantial acreage provide a welcome sense of seclusion. A distinctive offering on one of Osterville’s premier residential streets, this is a property that brings together architectural character, exceptional outdoor living, and privacy in a coveted Cape Cod setting. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

434 Sea View Ave, Barnstable

$16,500,000

8 Beds ⋅ 11 Baths ⋅ 73586293 MLS

Set along the soothing waters of West Bay, this exceptional waterfront estate, with approx. 400' of waterfront, captures magnificent western exposure, offering ever-changing views of boats navigating to and from the harbor and spectacular evening sunsets dancing across the water. This 'Wianno Head' area is one of the most coveted areas of Osterville with large, private estate settings. This property also benefits from protected conservation 'Land Trust' land directly across from its gated entrance to the property. The main residence encompasses warm, luxurious living spaces, distinguished by extensive custom millwork, custom stone, tile and brick work, and refined architectural details throughout. The gourmet kitchen and butler's pantry are designed to delight, while the grand living room and adjoining dining room provide an elegant setting for entertaining. A sunroom overlooks the water, while the inviting family room and adjacent dining area create comfortable spaces for everyday living. The residence offers a 1st floor bedroom suite, and the 2nd floor provides three bedroom suites and a glorious master suite with his-and-her bathrooms and dressing rooms, a private sitting room, and a deck with exceptional water views. The third floor features an additional bedroom and bath, a family room, and a charming widow's walk overlooking the surrounding landscape and bay. A finished lower level provides additional flexible living and recreational space. A separate two-bedroom, two-bath carriage house offers a full kitchen and living room, providing an ideal private retreat for guests and extended family. Encompassing three acres of beautifully landscaped, park-like grounds, that are irrigated by a private well, the property offers an extraordinary sense of privacy. Manicured lawns and gracious mature trees frame an inviting PebbleTech-finish pool, an expansive terrace, perfectly suited for outdoor entertaining and enjoying unforgettable sunsets. Steps lead down to the water's edge, where a private sitting area provides a peaceful place to take in the views. A permanent deep-water dock on West Bay complete this remarkable waterfront setting. The prestigious Wianno Club and Oyster Harbors Club, as well as Nauticus Yacht Club, Crosby Boatyard, and the numerous shops and restaurants in the village, are only minutes away. All information stated here in or verbally stated, should be verified by the Buyer(s) and their representatives.

143 Bayberry Way, Barnstable

$959,000

3 Beds ⋅ 3 Baths ⋅ 73585987 MLS

Beautifully renovated and thoughtfully designed by an Osterville builder, this custom ranch offers the ease of one-level living with the elevated finishes of a designer home including 3 beds with a large master suite and 3 full baths each one has its own unique design. The light-filled interior features a cathedral shiplap ceiling, Phillip Jeffries wallcoverings, extensive marble, custom cabinetry and a stunning kitchen appointed with premium Viking and Miele appliances. Marble finishes continue throughout the beautifully designed baths. The walk-out lower level adds valuable bonus living space, ideal for a family room, home office, gym or guest area along with a 3 season screened in porch. Fresh cottage-inspired details and a sophisticated coastal palette complete the transformation. For buyers seeking a move-in-ready Osterville home, renovated ranch, first-floor living or the feel of new construction, 31 Jason's Lane delivers timeless Cape Cod style with a designer's touch.

31 Jasons Ln, Barnstable

$15,850,000

8 Beds ⋅ 9 Baths ⋅ 73585729 MLS

Set on 2.35 beautifully landscaped acres along Eel River, this exceptional Osterville waterfront estate enjoys western exposure, sweeping water views, and a substantial deep-water dock with direct access to Nantucket Sound. The setting is defined by an extraordinary combination of privacy, scale, and waterfront amenities, creating a rare sense of arrival and an exceptional connection to the water. The six-bedroom main residence offers approximately 7,000 square feet of living space, with a gracious floor plan designed to take full advantage of the setting. From the grand foyer, panoramic water views immediately draw the eye through the home and toward the expansive grounds and waterfront beyond. The main level offers generous living and entertaining spaces, while the second floor features a spacious primary suite with fireplace, walk-in closet, and private bath, along with five additional bedrooms. The lower level includes a recreation room, exercise room, and abundant storage, with an attached two-car garage. The waterfront grounds are the centerpiece of the property. An expansive pool, glass-enclosed pool house, and substantial deep-water dock create an exceptional setting for summer living, boating, and entertaining. The western exposure brings beautiful afternoon and evening light across the water, while the location provides direct access to Nantucket Sound. A separate two-bedroom carriage house with attached two-car garage and private patio provides comfortable accommodations for guests and extended family. Osterville Village, with its high-end shops and refined dining, is close at hand, as are the area’s renowned golf clubs. With its extraordinary acreage, western water views, deep-water access, pool, guest accommodations, and exceptional privacy, this is a waterfront estate of uncommon scale and presence. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

141 Eel River Rd, Barnstable

$16,000,000

7 Beds ⋅ 13 Baths ⋅ 73584008 MLS

Privately set behind a gated drive on two acres along Eel River, this remarkable Osterville waterfront estate commands a rare vantage point overlooking the river and Nantucket Sound. The architecture is designed around the setting, with broad expanses of glass, soaring coffered ceilings, fine millwork, and a succession of light-filled spaces oriented toward the water. The main level brings together a gracious chef’s kitchen, a dramatic great room overlooking the water, and a luxurious primary suite with its own media room. The residence unfolds across three levels, with a graceful stairway connecting each floor. The second level offers three additional bedroom suites, while the third floor creates a more intimate retreat, with a spacious waterfront sitting room opening to a private balcony, and a fifth bedroom along with two bonus rooms. The finished lower level is dedicated to recreation, with a theater accommodating 20 and a substantial game and media room. Beyond the main residence, the property takes on the character of a private coastal compound. A separate two-bedroom guest house with three-car garage and pool house overlooks the expansive pool and surrounding grounds. Multiple terraces and outdoor rooms lead toward the water, where a private sandy beach and substantial deep-water dock provide direct access to Eel River and Nantucket Sound. The setting is quintessentially Osterville: private, deeply connected to the water, and minutes from the village, its beaches, harbor, shops, and restaurants. With its scale, architectural pedigree, guest accommodations, and exceptional boating access, this is a distinctive waterfront offering in one of Cape Cod’s most sought-after enclaves. The information contained herein has been obtained through sources deemed reliable but cannot be guaranteed as to its accuracy. Buyers are encouraged to do their own due diligence through independent verification.

74 Garrison Ln, Barnstable

$849,900

2 Beds ⋅ 2 Baths ⋅ 73582615 MLS

Set on a wooded half-acre lot in Osterville, this 2-bedroom, 1.5-bath ranch offers comfortable one-level living and a peaceful connection to the outdoors. Hardwood floors and natural light brighten the living spaces, while a large bay window makes the room currently used as an office an inviting place to work or unwind. The kitchen opens to the dining area, and a patio provides a spot to relax beneath the trees. Enjoy the spacious, level backyard with room to garden or gather around a fire. The seller has cleared underbrush from the rear of the lot and obtained a mortgage inspection plan and lot survey while exploring the potential for an ADU; buyers should verify feasibility and permitting with the town. A full basement, storage shed, gas heat, town water, and a paved driveway with parking for three complete the property. Convenient to Osterville’s shops, beaches, golf, and walking trails.

466 Old Mill Rd, Barnstable

$8,995,000

6 Beds ⋅ 9 Baths ⋅ 73581579 MLS

Presiding over West Bay, this extraordinary waterfront estate spans 2.35 pristine acres with breathtaking views in an unrivaled location. A park-like driveway winds through manicured grounds with sculpted boxwood hedges and vibrant hydrangeas, creating a sense of privacy and grandeur as you approach the residence. A private dock provides immediate access to West Bay and Nantucket Sound, while the waterside swimming pool and pool house create a resort-like atmosphere. Inside, the residence showcases fine architectural millwork, soaring ceilings, limestone flooring, and six fireplaces across its gracious living spaces. The intuitive layout centers around an impressive main living room where French doors trace the water side of the home, allowing natural light to pour inside while framing panoramic views. Cooking and daily living center around the gourmet kitchen, which features a custom wood center island with seating, professional-grade appliances, and natural stone countertops. Exceptional quality and attention to detail are evidenced throughout, from the oval wood-paneled library with built-in bookshelves to the industrial-grade HVAC system ensuring the utmost comfort. Six well-appointed en suite bedrooms provide exceptional accommodations for all, including a luxurious primary suite with two full bathrooms, two dressing rooms, and serene views of the water. Outside, an expansive stone patio surrounds the swimming pool and spa, providing an effortless setting for al fresco dining and entertaining amidst a stunning backdrop. Combining refined craftsmanship and modern luxury in one of Cape Cod's most coveted neighborhoods, this inimitable waterfront estate is located minutes from Wianno, Oyster Harbors, Main Street, and everything Osterville has to offer.

204 Garrison Lane, Barnstable

$799,900

2 Beds ⋅ 2 Baths ⋅ 73581180 MLS

Attractive and Custom Straight Ranch 42x24 +14x12 +21x17! 1- level living features Fireplaced Living room with bay window / 3rd Bedroom or Study/Office/Den with picture window and closet / Custom Kitchen with contemporary cabinets, peninsula, eat-in area, vinyl flooring and 1/2 wall with oak trim overlooking an incredible 1st Floor Family room with entry to 22x14 deck / Family room features Open beamed cathedral ceiling, skylights / custom windows / raised hearth Fireplace, sliders to an oversized deck / Main Bedroom suite with walk-in closet, laundry and private bathroom / 2nd Bedroom with wall to wall carpeting and coat closet / Hallway with pull-down stairs to attic and access to Full bathroom / Full basement under addition / Partially crawl under main house / Generator fired by natural gas / Title V completed / Fenced yard / This home is unique with an Open Floor plan! Close to stores and conveniences,

87 Hinckley Circle, Barnstable

$2,825,000

4 Beds ⋅ 4 Baths ⋅ 73577150 MLS

Perfectly situated within a 5-minute drive of the beach, Main Street Osterville shopping and restaurants, and Route 28, which opens all of the Cape to exploration and fun, this gracious 4-bed, 4-bath home offers a peaceful retreat where timeless coastal charm meets effortless outdoor living. Set among mature trees and beautifully groomed landscaping, the wooded setting creates privacy and a sense of escape, while the inviting deck and three-season screened porch extend the living space into nature. Inside, glowing hardwood floors and abundant windows fill the home with warmth and natural light. Soaring ceilings and beautiful exposed beams add a sense of grandeur, while multiple fireplaces, framed by timeless brick and distinctive wood mantels, create cozy gathering spaces throughout. The expansive kitchen shines with polished granite countertops, bright white cabinetry, stainless steel appliances, including a double oven and gas range, blending beautifully with the home’s classic character.And every bathroom is truly amazing, with beautiful finishes and a polished, inviting feel. The extraordinary primary bedroom is a true sanctuary, with abundant windows creating an atmosphere that feels both grand and intimate. The spa-like primary bath features a dual vanity, separate garden tub, and beautiful finishes, offering a serene place to begin and end the day. Outside, a paver patio surrounds the sparkling swimming pool and outdoor BBQ, creating a private setting made for long sunny afternoons and evenings gathered with friends. Add to this the huge, partially finished basement and garage to provide abundant storage and flexibility. A home where sunlight, greenery, and Cape Cod ease come together beautifully. Come view today!

55 Seapuit Rd, Barnstable

$599,900

2 Beds ⋅ 2 Baths ⋅ 73575652 MLS ⋅ ['Wianno Knoll'] BLDG.

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......

727 Main Street Unit B1, 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

Start Your Search

The property listing data and information, or the Images, set forth herein were provided to MLS Property Information Network, Inc. from third party sources, including sellers, lessors, landlords and public records, and were compiled by MLS Property Information Network, Inc. The property listing data and information, and the Images, are for the personal, non commercial use of consumers having a good faith interest in purchasing, leasing or renting listed properties of the type displayed to them and may not be used for any purpose other than to identify prospective properties which such consumers may have a good faith interest in purchasing, leasing or renting. MLS Property Information Network, Inc. and its subscribers disclaim any and all representations and warranties as to the accuracy of the property listing data and information, or as to the accuracy of any of the Images, set forth herein.

Osterville Real Estate

Newest Listings in Osterville

How much is your home worth?

How much is your home worth?