Osterville, Massachusetts listings for sale

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$5,850,000 - Osterville, MA
35 Hidden Lane Osterville, MA - A rare multi-generational waterfront estate in the heart of Osterville. ''Daybreak'' offers almost 6000 square feet of living space on a private ¾ acre lot. As you enter the main residence you are struck by the panoramic views of Neck Pond and the Wianno Golf Course. The custom design is centered on the vaulted great room which features a wood-burning fieldstone fireplace and floor-to-ceiling glass, capturing the stunning landscape while the southwest exposure allows hours of natural light to flood the home. The main residence is an open living floor plan which includes a gourmet kitchen, dining area, and three-season sunroom which flow seamlessly to a wraparound deck, creating effortless indoor-outdoor living. The first-floor primary suite offers an en-suite bath, a private deck with water views and an adjacent den/office with a gas fireplace and walls of built-ins. The upper level offers a second bedroom suite, two guest bedrooms and a cozy reading area. The finished walk-out lower level is designed as a complete entertainment center with a game and family space, pool table, wet bar, gym, craft room, loads of closet/storage space as well as a full bathroom with indoor and outdoor access. Outdoor spaces include an expansive bluestone terrace, pergola-covered hot tub and fire pit, outdoor shower and a private dock for swimming, fishing, and small craft water activities. Across the circular driveway there is 3 bay heated garage with a workshop and potting room. The guest suite above, accessed by a 2 person lift, also offers spectacular water views from the private deck and fireplaced living area. It is perfect for the guests needing privacy and quiet time or even an artist's loft. The gardeners in the group will be delighted by an enclosed raised bed garden space and an impressive herb garden. The littlest ones will love the playset and shed for creating their own fantasies of a cozy home. Additional features include laundry closets on all three levels, gleaming hardwood floors, two whole house generators and radiant floor heating. This waterfront retreat is a hidden gem! And the best part is it is just a short walk to a quaint village with shopping, restaurants, library and banks, with all the charm you are searching for in a quintessential Cape Cod village.
2006 | 5 | 6 | 5,957 sqft.
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$5,444,000 - Osterville, MA
38 Beach Plum Hill Road Osterville, MA - Nestled in Osterville's coveted Seapuit enclave, this EB Norris-built estate spans over two acres of serene privacy and limitless potential. From the rolling lawns and infinity pool to its deep-water access on Nantucket Sound, the property offers a rare coastal retreat. Soaring windows flood the interior with natural light, revealing mesmerizing, western-facing sunsets and layered views from every room. The flexible floor plan seamlessly integrates grand entertaining spaces with intimate corners, anchored by a luxurious first-floor primary suite for ultimate comfort. Whether you envision a multi-generational residence or simply desire room to expand, this oasis invites you to craft a lasting Cape Cod legacy. Located mere moments from Osterville's renowned Main Street, world-class golf, exclusive clubs, and pristine beaches, this estate transcends the ordinary, delivering an extraordinary lifestyle for discerning buyers seeking the very best of Cape Cod living.
1985 | 5 | 4 | 3,802 sqft.
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$5,200,000 - Osterville, MA
150 Sea View Avenue Osterville, MA - Iconic Sea View Avenue, in the heart of Wianno, this enchanting property is meticulously maintained, welcoming and ready. Discover its old-world charm, casual elegance and modern resort style living. This home features 7 bedroom, 5.5 baths, a spacious and stunning living room, a grand dining room, a classic, well-appointed kitchen and superior craftsmanship inside and out. There are beautiful, landscaped gardens and spectacular hydrangeas. A gracious wrap around porch; expansive granite patio; heated saltwater, Gunite pool; spa with soothing waterfall; a cabana offering an outdoor chef's kitchen and an additional bath. With its elegant interior, exceptional outdoor areas and casual seaside vibe, this home is the epitome of luxurious, coastal living.
1910 | 7 | 6 | 4,043 sqft.
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$2,879,000 - Osterville, MA
98 Bunker Hill Road Osterville, MA - Experience the epitome of bayside living at 98 Bunker Hill Road, nestled in Osterville's distinguished Seapuit neighborhood. Sitting peacefully on over 2 acres, this 4,715 sq. ft. estate offers five bedrooms, including three with ensuite baths, and a host of inviting spaces perfect for relaxation or entertaining. Exterior assets include an attached three car garage, an abundant backyard with a swimming pool and hot tub, and deeded rights to Dam Pond! The grand entryway leads to a soaring living room filled with natural light, featuring a striking floor-to-ceiling brick fireplace. The bright, modern kitchen is equipped with stainless steel appliances, a central island, and casual dining space, seamlessly connecting to the formal dining room and a dedicated laundry room. The spacious family room impresses with hardwood floors, high ceilings, custom built-ins, and a wood-burning stove framed by cozy bench seating. A wet bar elevates the space for hosting, while a versatile bonus room above serves as a playroom, gym, or billiards room. The home's opposite wing includes a cheerful office with a wood stove, a guest suite with a full bath, and the luxurious primary suite. This retreat features dual walk-in closets, an expansive bath with a jacuzzi tub and double vanity, and tranquil views of the pool. Upstairs, three additional bedrooms and two full baths offer privacy and comfort. The backyard is a summer oasis, with a sparkling pool, hot tub, outdoor shower, gas grill, and a sprawling patio ideal for entertaining or unwinding. If you're in the mood for a salt water swim or paddle, the property comes with deeded rights to Dam Pond, which connects to North Bay. Sophisticated yet inviting, this property delivers on every aspiration. Discover all it has to offer today!
1978 | 5 | 4 | 4,715 sqft.
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$1,395,000 - Osterville, MA
120 Robbins Street Osterville, MA - 120 Robbins has great curb appeal but what is truly amazing is the interior and all the surprises it holds for the discerning buyer....not only do we have a wonderful open floor plan filled with sunshine we have doors that open to rooms you did not expect. The four season porch is a fabulous bonus which opens to beautiful landscaping and decks. There is a bonus room adjacent to the primary bedroom that makes for a perfect at home private office...and did we mention the third floor perfect for grandkids or just a playroom. You can stroll to the village or Dowses Beach from this in town location. Don't miss this exceptional offering in Osterville Village.
1989 | 3 | 4 | 3,226 sqft.
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$1,195,000 - Osterville, MA
50 Deerfield Road Osterville, MA - Nestled in a quiet neighborhood near Dowses Beach and Main Street Osterville, this updated Cape-style home exudes a coastal-casual vibe. The sun-filled first floor offers an open layout ideal for entertaining. The chef's kitchen features a large island, quartz countertops, GE Profile appliances, and a farmhouse sink overlooking the spacious backyard. Hardwood floors, crown molding and a stunning fireplace add warmth. The entryway mudroom and walk-in pantry offer everyday convenience with a decorator's charm. A private guest bedroom and full bath complete the first level. The expansive fenced yard is perfect for outdoor activities and entertaining, featuring an outdoor shower, irrigation, and room for a pool. This home boasts ample storage space throughout, including an unfinished basement and attic above the oversized two-car garage. Central air, including mini-splits in each of the three upstairs bedrooms, complete this quintessential Cape retreat. This home is a must see!
1972 | 4 | 3 | 2,098 sqft.
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$1,195,000 - Osterville, MA
25 Milne Road Osterville, MA - Welcome to this beautifully renovated 3- bedroom, 1.5-bathroom home that blends modern elegance with timeless comfort. The heart of the home is a stunning kitchen featuring a large, custom quartz island, perfect for meal prep, entertaining, and casual dining; new sleek cabinetry and French doors that seamlessly open to a large patio- perfect for indoor/outdoor living and entertaining. The spacious, fenced-in level yard offers plenty of room for outdoor activities, gardening, the addition of a pool or expansion. Each of the bathrooms exude a spa-like ambiance, with high end fixtures and finishes that provide a luxurious retreat within your own home. Don't miss the opportunity to own this turnkey and energy efficient home where all the hard work has been done for you. Move in and start enjoying your dream home today!
1955 | 3 | 2 | 1,440 sqft.