Osterville MA Real Estate & Homes for Sale

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Beds:
5
Baths:
8.00
Sq.Ft.:
4,955
Status:
NEW LISTING
MLS#:
73589132
Type:
Single Family
Lot size:
2.44 Acres
Year built:
2003
Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,706
Status:
NEW LISTING
MLS#:
73587619
Type:
Single Family
Lot size:
0.98 Acres
Year built:
1922
Courtesy: Compass 508-747-0080
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ADDITIONAL INFORMATION

Rare Osterville Offering: Endless Potential for Developers, and Dreamers: Discover an incredible opportunity in desirable Osterville. Set on a completely level, 1-acre lot abutting Cape Cod Academy and the tranquil Johnson Tree Farm, this property delivers a rare blend of location, versatility, and future upside. Ideally positioned south of Route 28, you are just minutes from main st, Osterville, Dowses Beach, and Crosby Yacht Yard, while enjoying being minutes to Amie's Bakery, Beacon Gardens, Joshua's and Micha's ponds and the Skunknett River Wildlife Sanctuary. The main home presents a charming, flexible 3-bedroom, 2-bathroom layout featuring a finished lower level, offering a fresh canvas to update and reimagine. Peace of mind comes built-in with a newer roof and brand-new heat pumps backed by a 9-year warranty. A true standout of the property is the expansive 24x60 detached garage complete with an office and bathroom. It is ideal for contractors, hobbyists, or car enthusiasts, and lends itself to exciting potential as a permitted Accessory Dwelling Unit (ADU) under current Massachusetts legislation. With a full acre of level land in a premier neighborhood, the possibilities are vast. For builders and developers, the town's Bumps River Rd branch sewer hookup slated for completion in Fall 2028 unlocks incredible potential for future subdivision and maximum return. Whether you are looking to create your custom Cape Cod dream estate, establish a live-work setup, or execute a savvy investment project, this property delivers unmatched utility. Bring your vision and explore the endless possibilities today!

Beds:
3
Baths:
3.00
Sq.Ft.:
1,506
Status:
NEW LISTING
MLS#:
22605105
Type:
Other
Lot size:
1.21 Acres
Year built:
1800
A broker reciprocity listing Courtesy: William Raveis - Nantucket 508-228-9117
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ADDITIONAL INFORMATION

Set on 1.2 acres in an exceptional location along the highly desirable south-facing side of Starboard Lane, this Osterville property offers a rare opportunity to renovate, reimagine, or create a custom dream home in one of the village's most sought-after settings. The existing three-bedroom, three-bath residence enjoys partial water views and provides an appealing foundation for a buyer, builder, or investor looking to take full advantage of this prime parcel. The first floor features a spacious primary suite with high ceilings and an en-suite bath, along with an open-concept kitchen and den designed for comfortable everyday living. A second full bath includes a steam shower and distinctive Sherle Wagner-designed sink. A gracious living room with a working fireplace and an enclosed, winterized porch complete the main level. Upstairs are two additional bedrooms, a full bath, and a dedicated laundry room with space for a washer and dryer. A detached two-car garage is located at the rear of the property.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,170
Status:
Active
MLS#:
22605144
Type:
Other
Lot size:
0.24 Acres
Year built:
1963
A broker reciprocity listing Courtesy: Cape Cod Real Estate Services 508-790-2000
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ADDITIONAL INFORMATION

The Cottage- Osterville Village. A rare offering in the heart of Osterville Village: a renovated duplex townhome just one block from Main Street and steps from Joshua's Pond. One of two residences in this private enclave- a setting that delivers quiet, space, and exclusivity. An arbor marks the front approach, with a fenced front yard and a private side entrance. Beyond the door, a private backyard, a shell driveway and a generous south-facing deck. A small waterfall, and a private patio under a pergola draped with trumpet vines, completes the outdoor space. A true sanctuary for the nature lover. Inside, the light pours through a cathedral skylit living room anchored by a gas fireplace and beautiful hardwood floors. Whether as a Cape Cod retreat, an income producing property, or a year-round residence, The Cottage delivers - close to Dowses Beach, village shops and restaurants. Companion unit also available. Seller will consider selling both units together. Inquire for details. Offered as a condominium unit upon completion of a 2-unit conversion.

Beds:
8
Baths:
11.00
Sq.Ft.:
8,763
Status:
Active
MLS#:
73586293
Type:
Single Family
Lot size:
3.02 Acres
Year built:
1914
Courtesy: Frank Sullivan Real Estate, LLC 508-428-4400
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
4.00
Sq.Ft.:
3,012
Status:
Active
MLS#:
73586285
Type:
Single Family
Lot size:
1 Acres
Year built:
2019
Courtesy: Frank Sullivan Real Estate, LLC 508-428-4400
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ADDITIONAL INFORMATION

Luxurious Oyster Harbors residence with Deeded Beach Rights! This architecturally designed, luxury built home by Bayside Building features impressive exterior roof lines and extensive millwork throughout. The quality of construction is readily evident from the moment you arrive at the residence. The 1st floor features an expansive 2-story living room with a gas fireplace, an adjacent dining room, a gourmet kitchen w/ center island & a sep. wet bar area, an expansive master bedroom suite with a luxurious master bathroom, a sep. guest suite, laundry room, half bath, and an expansive screened-in porch which also has a gas fireplace. The 2nd floor features 2 bedrooms, a bathroom, and a large family room. The professionally maintained grounds have numerous hydrangeas, mature trees for privacy, a heated pebble-tech pool and spa, a pool house with a half bath and laundry. There is a 2-car att. garage, a front open porch, and a generator. In addition, this property benefits from deeded beach and docking rights. All information in print or verbally stated, should be verified by a Buyer(s) & their representative(s).

Beds:
3
Baths:
3.00
Sq.Ft.:
2,048
Status:
Active
MLS#:
73585987
Type:
Single Family
Lot size:
0.35 Acres
Year built:
1981
Courtesy: Sotheby's International Realty 508-428-9115
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ADDITIONAL INFORMATION

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.

Beds:
8
Baths:
9.00
Sq.Ft.:
7,730
Status:
Active
MLS#:
73585729
Type:
Single Family
Lot size:
2.35 Acres
Year built:
1927
Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
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ADDITIONAL INFORMATION

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.

Beds:
7
Baths:
13.00
Sq.Ft.:
14,292
Status:
Active
MLS#:
73584008
Type:
Single Family
Lot size:
2 Acres
Year built:
2006
Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,055
Status:
Active
MLS#:
73582615
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1955
Courtesy: Griffin Realty Group 617-249-4822
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ADDITIONAL INFORMATION

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.

Beds:
6
Baths:
9.00
Sq.Ft.:
9,464
Status:
Active
MLS#:
73581579
Type:
Single Family
Subdivision:
Wianno Head
Lot size:
2.35 Acres
Year built:
2002
Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
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ADDITIONAL INFORMATION

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.

Beds:
2
Baths:
2.00
Sq.Ft.:
1,533
Status:
Active
MLS#:
73581180
Type:
Single Family
Lot size:
0.23 Acres
Year built:
1963
Courtesy: Raymond & Son REALTORS® 781-337-1894
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ADDITIONAL INFORMATION

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,

Beds:
3
Baths:
3.00
Sq.Ft.:
1,501
Status:
Active
MLS#:
73580945
Type:
Single Family
Lot size:
0.26 Acres
Year built:
1977
Courtesy: Margo & Company 508-428-4443
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ADDITIONAL INFORMATION

Osterville Beauty! Nestled on a private lot offering a very private year yard with hot tub, fire pit deck, grill area and shed with Tiki bar! The interior of this 3 bedroom, 2.5 bath home shows like new! ideal floor plan for entertaining! The family room with beamed ceiling, nautical trim and fireplace is the perfect spot for "movie night!". The easy to navigate kitchen is fully applianced, with upgraded cabinets, granite counters and breakfast bar plus half bath. The primary bedroom is on the first level offering a private ensuite bath with Shower and separate spa tub, plus walk in closet! Perfect! hardwood floors throughout and on both levels. 2 bedrooms a d full bath complete the 2nd floor. The partially finished basement provides laundry and extra recreation or home office space. 1 car attached garage completes the property. Minutes to Osterville village center for dining, boutique shopping, galleries and more. 2.1 miles to stunning Dowses Beach!

Beds:
4
Baths:
4.00
Sq.Ft.:
3,523
Status:
Active
MLS#:
73577150
Type:
Single Family
Lot size:
1.52 Acres
Year built:
1999
Courtesy: Griffin Realty Group 617-249-4822
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ADDITIONAL INFORMATION

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!

Beds:
2
Baths:
2.00
Sq.Ft.:
1,088
Status:
Active
MLS#:
73575652
Type:
Condo
Year built:
1967
Courtesy: Craigville Realty, Inc. 508-775-3174
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ADDITIONAL INFORMATION

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......

Beds:
3
Baths:
3.00
Sq.Ft.:
2,116
Status:
Active
MLS#:
73572743
Type:
Single Family
Lot size:
0.34 Acres
Year built:
1999
Courtesy: Sotheby's International Realty 508-428-9115
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ADDITIONAL INFORMATION

This delightful 3 Bedroom Family/Vacation Home in the much desirable village of Osterville: Nestled in a well maintained neighborhood, this 2116 sf home would be ideal as a primary residence or Cape Cod getaway. Elegant hardwood floors throughout the main floor. Upstairs you'll find 2 spacious guest bedrooms and a study/den loft room. This inviting home features a large primary suite, with a walk-in closet and ample storage. The private yard features a large deck, perfect for outdoor living and entertaining. An attached 2-car-(heated) garage, a full basement w/great ceiling height, providing excellent flexibility, storage and future expansion. Nature lovers will appreciate the exceptional location- at the end of the cul-de-sac is the Skunknett River Wildlife Sanctuary. Explore the 147 acres of marked trails, vernal pools, birds, and abundant wildlife right at your doorstep! Conveniently located 0.3 mi to Cape Cod Academy, 1.8 mi to the village downtown, 3.2 mi to Dowses beach. The home is complete with an alternative/innovative wastewater (Ruck) septic system. A rare opportunity to enjoy peaceful living with nature, space and the Cape Cod lifestyle we come to thoroughly enjoy! If this is the area you're looking for, don't miss this exceptional home!

Beds:
2
Baths:
3.00
Sq.Ft.:
1,564
Status:
Active
MLS#:
73571682
Type:
Single Family
Subdivision:
Aunt Tempy's
Year built:
2023
Courtesy: Compass 508-206-8726
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
2,126
Status:
Active
MLS#:
73571509
Type:
Single Family
Lot size:
0.23 Acres
Year built:
1972
Courtesy: Garland Group, LLC 774-571-1113
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ADDITIONAL INFORMATION

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.

Beds:
3
Baths:
3.00
Sq.Ft.:
1,844
Status:
Active
MLS#:
22604426
Type:
Single Family
Lot size:
1.11 Acres
Year built:
1956
A broker reciprocity listing Courtesy: Compass Massachusetts, LLC 508-206-8726
View additional info

ADDITIONAL INFORMATION

Beautifully renovated and thoughtfully improved, 23 & 27 Swift Avenue is a rare two-parcel Osterville offering totaling approximately 1.11 acres, just moments from Osterville Village. Set on approximately .66 acre, the charming 3-bedroom residence 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. Inside, sun-filled living spaces feature warm wood floors, classic Cape character and a beautifully appointed kitchen flowing to the dining and family areas with direct access to the expansive backyard. 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 mature landscaping, expansive lawns, oversized spa, outdoor shower and stone fire pit. A detached 2-car garage features temperature/humidity controls and epoxy flooring. Additional parcel offers potential future possibilities, subject to approvals. 23 & 27 Swift Avenue are being sold together. 27 Swift may offer some additional developmental options (G.L. c. 40a 2024)

Beds:
4
Baths:
3.00
Sq.Ft.:
3,355
Status:
Active
MLS#:
22604359
Type:
Single Family
Subdivision:
Tanglewood
Lot size:
0.34 Acres
Year built:
1978
A broker reciprocity listing Courtesy: Coastal Real Estate Advisors LLC 617-416-4601
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ADDITIONAL INFORMATION

Back on Market - 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.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,856
Status:
Active
MLS#:
22604277
Type:
Single Family
Lot size:
0.31 Acres
Year built:
1953
A broker reciprocity listing Courtesy: Sotheby's International Realty 508-428-9115
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ADDITIONAL INFORMATION

One of the best values among homes for sale in Osterville! Welcome to 329 Swift Avenue, a turnkey Osterville home offered at $799,000 with an established rental history, a desirable walk-to-village location, and exceptional future potential. Set on approximately .3 acres, this charming Cape Cod property offers the space buyers are looking for, including a generous yard with potential for a pool, subject to permitting.Located just minutes from the heart of Osterville Village, this home puts shopping, dining, coffee, beaches and the best of the Cape Cod lifestyle within easy reach. Whether you are searching for a year-round Osterville home, Cape Cod summer house, second home, or investment property, 329 Swift Avenue offers a rare combination of location, value and versatility. The property is being offered turnkey, allowing a new owner to begin enjoying it immediately or continue taking advantage of its proven rental history. With its walkable Osterville location, oversized lot, rental income history and under a 1 million, this is an outstanding opportunity in one of Cape Cod's most sought-after villages. The first photo is a virtual rendering showcasing potential curb appeal improvements, including a new cottage-style front door, window boxes, and an additional window. Please note that the seller will not be performing any of this work.

Beds:
2
Baths:
2.00
Sq.Ft.:
2,010
Status:
Active
MLS#:
73565564
Type:
Single Family
Lot size:
0.5 Acres
Year built:
2000
Courtesy: William Raveis R.E. & Home Services 508-428-3320
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ADDITIONAL INFORMATION

Welcome to 51 Falling Leaf Lane, a charming two-bedroom, two-bath ranch tucked away on a peaceful dead-end street in the heart of Osterville. Offering privacy, comfort, and convenience, this inviting home is an ideal Cape Cod retreat or year-round residence. The thoughtfully designed floor plan provides an easy flow between living spaces, with plenty of room to gather and entertain. Bright, welcoming interiors create a warm and comfortable atmosphere, while two spacious bedrooms offer comfortable accommodations for family or guests. A versatile bonus room provides added flexibility and can be used as a home office, den, hobby space, or occasional guest room. Enjoy the peaceful outdoor setting surrounded by mature trees and the natural beauty of Cape Cod. Just minutes from Osterville Village, beautiful beaches, restaurants, shopping, conservation areas, and recreational opportunities, this home offers the ideal combination of tranquility and convenience. A wonderful opportunity to enjoy the relaxed Cape Cod lifestyle in one of Osterville’s desirable locations.

Beds:
3
Baths:
2.00
Sq.Ft.:
1,248
Status:
Active
MLS#:
73565006
Type:
Single Family
Lot size:
0.5 Acres
Year built:
1985
Courtesy: Compass 617-206-3333
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ADDITIONAL INFORMATION

Welcome to 111 W Wind Cir, a beautifully renovated single-family home nestled in the heart of Osterville, MA. This stunning 3-bedroom, 2-bathroom property has been thoughtfully updated and offers comfortable living across 1,248 square feet of well-designed space. Step inside to find a bright and airy layout with six inviting rooms, perfect for relaxing or entertaining. The newly renovated kitchen boasts modern updates and plenty of space to cook and gather. Both bathrooms have been tastefully updated to offer a fresh, contemporary feel. Cozy up by the charming fireplace in the living area, creating a warm and welcoming ambiance throughout the seasons.Outside, enjoy the serene surroundings from your private deck – ideal for morning coffee, evening dinners, or simply unwinding in nature. The home offers the convenience of air conditioning to keep you comfortable year-round. A walk out basement offers exceptional additional living space and is tastefully finished.Parking will never be a concern with an included garage and additional parking spaces. Whether you're looking for a full-time residence or a seasonal retreat, this property offers both comfort and practicality in a fantastic location. Experience the perfect blend of modern amenities and timeless charm – a true gem on Cape Cod! Don’t miss this opportunity to make 111 W Wind Cir your next home.

Beds:
7
Baths:
11.00
Sq.Ft.:
10,104
Status:
Active
MLS#:
73563501
Type:
Single Family
Subdivision:
Oyster Harbors
Lot size:
1.97 Acres
Year built:
2007
Courtesy: Berkshire Hathaway HomeServices Robert Paul Properties 508-420-1414
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ADDITIONAL INFORMATION

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.

Beds:
4
Baths:
3.00
Sq.Ft.:
2,050
Status:
Active
MLS#:
22603965
Type:
Single Family
Lot size:
0.82 Acres
Year built:
1961
A broker reciprocity listing Courtesy: The Foley Company 508-685-8928
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ADDITIONAL INFORMATION

Discover the charm of Wianno in this beautifully renovated four-bedroom, three-bath home, walking distance to Osterville Village, beaches, and the best of Cape Cod living. With deeded access to Eel River and lovely views overlooking the Wianno golf course, this inviting property offers a rare combination of location, comfort, and lifestyle. Thoughtfully designed for easy one-level living, the turnkey home features a warm and welcoming living room with fireplace, vaulted ceilings, and a relaxed country feel. The spacious deck overlooking the golf course provides an idyllic setting for morning coffee, summer entertaining, or unwinding at the end of the day. This home's exceptional location puts Osterville Village, beaches, boating, dining, and shopping close at hand. Whether you're seeking a year-round residence or a special Cape Cod retreat, this Wianno property offers an outstanding opportunity in a highly desirable setting. New Title V compliant septic system installed.

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Andrea D. Conner, License 1?0?0?0?1?8?8, Xome Inc., License 9622, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067

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 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 or leasing 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 or leasing. 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. Copyright © 2026 MLS Property Information Network, Inc. All rights reserved.
Andrea D. Conner, License 1?0?0?0?1?8?8, Xome Inc., License 9622, [email protected], 844-400-XOME (9663), 750 Highway 121 Bypass, Suite 100, Lewisville, Texas 75067


The data relating to real estate for sale on this site comes from the Broker Reciprocity (BR) of the Cape Cod and Islands Multiple Listing Service, Inc. Summary or thumbnail real estate listings held by brokerage firms other than Xome are marked with the BR Logo and detailed information about them includes the name of the listing broker. Neither the listing broker nor this broker shall be responsible for any typographical errors, misinformation, or misprints and shall be held totally harmless. Copyright 2026 Cape Cod and Islands MLS, Inc. All rights reserved.



Osterville 02655 Real Estate

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%.

Osterville Weather

Osterville Map

Osterville Real Estate Market Conditions

  • Median sales price

    $1,195,000
    16.3%
    change since last quarter
  • # Active listings

    56
    30-day change

Osterville Schools and Demographics

Education near Osterville, MA

City County
High School Graduates N/A N/A
College Degree - 2 year N/A N/A
College Degree - 4 year N/A N/A
Graduate Degree N/A N/A
Expenditures per Student N/A N/A
Students per Teacher N/A N/A

Elementary Schools near Osterville, MA

Grades Students P/T Ratio ZIP
Barnstable Community Horace Mann Charter Public School KG - 03 291 12.3 02601
Centerville Elementary PK - 03 427 14.5 02632
Hyannis West Elementary School KG - 03 355 10.9 02601
Kenneth Coombs School PK - 02 443 13.6 02649
Quashnet School 03 - 06 525 12.6 02649
West Villages Elementary School KG - 03 450 15.8 02648

Middle Schools near Osterville, MA

Grades Students P/T Ratio ZIP
Barnstable Intermediate School 06 - 07 751 12.4 02601
Barnstable United Elementary School 04 - 05 772 13.2 02648
Mashpee Middle School 07 - 08 268 13.4 02649

High Schools near Osterville, MA

Grades Students P/T Ratio ZIP
Barnstable High School 08 - 12 1,911 13.4 02601
Mashpee High School 09 - 12 431 10.4 02649
Sturgis Charter Public School 09 - 12 806 9.4 02601

Demographics near Osterville, MA 02655

Zip Code City
Neighborhood Type
Population N/A N/A
Population Density N/A N/A
Median Age N/A N/A
People per Household N/A N/A
Median Household Income N/A N/A
Average Income per Capita N/A N/A

Real estate near Osterville