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Osterville Homes for Sale

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  • 850 Sea View Ave, Osterville, MA 02655
    850 Sea View Ave, Osterville, MA 02655
    850 Sea View Ave, Osterville, MA 02655
    /69

    $7,950,000

    • 8 Beds
    • 9 Baths
    • 7,350 Sq Ft

    850 Sea View Ave, Osterville, MA 02655

    At the western end of Osterville's legendary Sea View Avenue--a road many believe is one of the most beautiful and valuable on all of Cape Cod reveals a property that transcends the idea of a residence. On over one acre of sweeping, tree-lined greensward with glimpses of West Bay shimmering in the distance, here is a residence that is not simply lived in, but experienced.Accessed by a winding

    Agent Photo

    John Cotton

    Sotheby's International Realty

    (508) 504-1820

    850 Sea View Ave, Osterville, MA 02655
  • 3040 Falmouth Rd Unit H, Osterville, MA 02655
    3040 Falmouth Rd Unit H, Osterville, MA 02655
    3040 Falmouth Rd Unit H, Osterville, MA 02655
    /27

    $357,000

    • 2 Beds
    • 1 Bath
    • 594 Sq Ft

    3040 Falmouth Rd Unit H, Osterville, MA 02655

    Welcome to 3040 Falmouth Road, Unit H--a rare, free-standing condo tucked within the sought-after Osterville Pines community. This absolutely charming residence lives like a single-family home and features beautiful hardwood floors, high ceilings, and a cozy living room that opens to a sunlit, eat-in kitchen. Two perfectly sized bedrooms are filled with natural light, and the fully renovated

    Agent Photo

    Livia Monteforte

    Compass Massachusetts, LLC

    (508) 257-7938

    3040 Falmouth Rd Unit H, Osterville, MA 02655
  • 3040 Falmouth Rd Unit H, Osterville, MA 02655
    3040 Falmouth Rd Unit H, Osterville, MA 02655
    3040 Falmouth Rd Unit H, Osterville, MA 02655
    /26

    $357,000

    • 2 Beds
    • 1 Bath
    • 594 Sq Ft

    3040 Falmouth Rd Unit H, Osterville, MA 02655

    Welcome to 3040 Falmouth Rd, Unit H—a rare free-standing condo in the sought-after Osterville Pines community. This charming detached condo lives like a single-family (electric, heat, gas and water included in condo fees), featuring hardwood floors, high ceilings, and a fireplaced living room opening to a bright eat-in kitchen. Two sunny bedrooms and a beautifully renovated bath with river stone

    Agent Photo

    Livia Monteforte

    Compass

    (508) 514-5783

    3040 Falmouth Rd Unit H, Osterville, MA 02655
  • 391 Sea View Ave, Osterville, MA 02655
    391 Sea View Ave, Osterville, MA 02655
    391 Sea View Ave, Osterville, MA 02655
    /50

    $13,500,000

    • 6 Beds
    • 7 Baths
    • 6,830 Sq Ft

    391 Sea View Ave, Osterville, MA 02655

    Overlooking the shimmering waters of Nantucket Sound, this extraordinary Wianno estate offers an unparalleled blend of elegance, privacy, and coastal charm. With its own private sandy beach and panoramic ocean views, this is a rare opportunity to own a legacy property, along Sea View Avenue, in one of Cape Cod's most coveted enclaves. Surrounded by lush, professionally landscaped gardens, the

    Gene Orloff Sotheby's International Realty

    391 Sea View Ave, Osterville, MA 02655
  • 168 Garrison Ln, Osterville, MA 02655
    168 Garrison Ln, Osterville, MA 02655
    168 Garrison Ln, Osterville, MA 02655
    /58

    $9,995,000

    • 5 Beds
    • 5.5 Baths
    • 7,565 Sq Ft

    168 Garrison Ln, Osterville, MA 02655

    Nestled amid beautifully landscaped grounds, this exceptional 7,500+/- square foot residence captures breathtaking views over West Bay and Eel River. A private sandy beach and deep-water dock provide effortless access to Nantucket Sound, creating a rare combination of serenity and seafaring adventure. Inside, the five-bedroom home blends refined architecture with inviting coastal warmth. A

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    168 Garrison Ln, Osterville, MA 02655
  • 439 Sea View Ave, Osterville, MA 02655
    439 Sea View Ave, Osterville, MA 02655
    439 Sea View Ave, Osterville, MA 02655
    /36

    $5,995,000

    • 6 Beds
    • 6 Baths
    • 4,021 Sq Ft

    439 Sea View Ave, Osterville, MA 02655

    Presenting the quintessential Cape Cod beach home on sought-after Sea View Avenue. This classic waterfront residence enjoys unobstructed views of Nantucket Sound with a picture-perfect sandy beach. The six-bedroom home showcases Old World craftsmanship and original period details throughout, including wide heart pine plank floors and paneling. At the heart of the home, a spacious living room with

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    439 Sea View Ave, Osterville, MA 02655
  • 414 Eel River Rd, Osterville, MA 02655
    414 Eel River Rd, Osterville, MA 02655
    414 Eel River Rd, Osterville, MA 02655
    /35

    $3,499,999

    • 10 Beds
    • 7.5 Baths
    • 6,905 Sq Ft

    414 Eel River Rd, Osterville, MA 02655

    Located in the desirable Wianno in Osterville surrounded by Luxurious homes, and walking distance to Wianno Golf course. This home has plenty of space for a large family or someone who likes to entertain. Home has three separate wings for privacy. Some of the recent improvements include kitchen with open concept. Kitchen has two stainless refrigerators and two dishwashers. Quartz countertops, and

    Shane Pacheco SMP Real Estate Investments and Development Co.

    414 Eel River Rd, Osterville, MA 02655
  • 14 Indian Trail, Barnstable, MA 02630
    14 Indian Trail, Barnstable, MA 02630
    14 Indian Trail, Barnstable, MA 02630
    /43

    $10,500,000

    • 5 Beds
    • 5 Baths
    • 3,087 Sq Ft

    14 Indian Trail, Barnstable, MA 02630

    Legacy, Lifestyle & Opportunity - A discreet treasure in one of Cape Cod's most prestigious enclaves, this exceptional waterfront property offers rare access to legacy, lifestyle, and limitless potential. Originally part of a historic compound long held by the Mellon family and now by noted philanthropist and collector William Koch, the property stands as a rare opportunity to own a slice of

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    14 Indian Trail, Barnstable, MA 02630
  • 440 Grand Island Dr, Osterville, MA 02655
    440 Grand Island Dr, Osterville, MA 02655
    440 Grand Island Dr, Osterville, MA 02655
    /42

    $7,750,000

    • 7 Beds
    • 11 Baths
    • 11,546 Sq Ft

    440 Grand Island Dr, Osterville, MA 02655

    Privately sited within the prestigious Oyster Harbors golf enclave, this extraordinary estate is a masterclass in architectural sophistication and resort-style living. Encompassing a 10,000-square-foot main residence, a stunning 2-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. Inside, refined architectural detail

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    440 Grand Island Dr, Osterville, MA 02655
  • 51 Wianno Cir, Osterville, MA 02655
    51 Wianno Cir, Osterville, MA 02655
    51 Wianno Cir, Osterville, MA 02655
    /31

    $2,395,000

    • 3 Beds
    • 2 Baths
    • 1,194 Sq Ft

    51 Wianno Cir, Osterville, MA 02655

    Tucked away in the heart of Wianno, this charming waterfront home enjoys exceptional privacy and scenic views of Neck Pond and the Wianno Golf Course.Set on .73 of an acre, this property has been held by the same family for generations and is now ready for its next chapter. Ideally located close to Dowses Beach and Osterville village, this home is the perfect Cape Cod get-away with room to

    Gene Orloff Sotheby's International Realty

    51 Wianno Cir, Osterville, MA 02655
  • 98 Bunker Hill Rd, Osterville, MA 02655
    98 Bunker Hill Rd, Osterville, MA 02655
    98 Bunker Hill Rd, Osterville, MA 02655
    /88

    $2,879,000

    • 5 Beds
    • 4.5 Baths
    • 4,715 Sq Ft

    98 Bunker Hill Rd, Osterville, MA 02655

    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

    Shaelyn Hegarty Frank A Sullivan Real Estate

    98 Bunker Hill Rd, Osterville, MA 02655
  • 123 Tower Hill Rd, Osterville, MA 02655
    123 Tower Hill Rd, Osterville, MA 02655
    123 Tower Hill Rd, Osterville, MA 02655
    /38

    $799,000

    • 3 Beds
    • 1.5 Baths
    • 1,136 Sq Ft

    123 Tower Hill Rd, Osterville, MA 02655

    With a prime in-town location, this 3-bedroom, 1.5-bath Osterville Cape offers the perfect blend of character, comfort, and convenience. The sun-soaked living room welcomes you with gleaming oak floors and an inviting wood-burning fireplace, creating a cozy yet open atmosphere. A private dining room and first-floor primary bedroom provide flexible living options, while the updated full bath adds

    Samantha Steward Compass Massachusetts, LLC

    123 Tower Hill Rd, Osterville, MA 02655
  • 40 Waterfield Rd, Osterville, MA 02655
    40 Waterfield Rd, Osterville, MA 02655
    40 Waterfield Rd, Osterville, MA 02655
    /34

    $1,125,000 Open Sun 10AM - 12PM

    • 4 Beds
    • 2 Baths
    • 1,775 Sq Ft

    40 Waterfield Rd, Osterville, MA 02655

    Your love affair will begin as you pull into the crushed stone, horseshoe drive w/ cobblestone aprons lined with white hydrangeas. This home looks like something out of a fairytale. A paved drive leads down to the 2-car gar., with basement access. In the rear, you'll find a large bluestone patio with an outdoor bar, TV, a seating area w/fire pit, and an outdoor shower. There’s a lush green lawn

    Gervais Group Keller Williams Realty

    40 Waterfield Rd, Osterville, MA 02655
  • 369 Bumps River Rd, Osterville, MA 02655
    369 Bumps River Rd, Osterville, MA 02655
    369 Bumps River Rd, Osterville, MA 02655
    /26

    $690,000 Open Sat 10AM - 12PM

    • 3 Beds
    • 2 Baths
    • 1,152 Sq Ft

    369 Bumps River Rd, Osterville, MA 02655

    Welcome to your new home in the highly sought-after village of Osterville! This charming 3 BD, 2 BA ranch at 369 Bumps River Road offers classic Cape Cod living. As you step inside, the living room's vaulted ceiling creates a spacious, inviting atmosphere, complete with a cozy fireplace for relaxing on a cool fall evening - heated by natural gas. Warm wood floors extend throughout the home,

    Eric Dufault Keller Williams Realty

    369 Bumps River Rd, Osterville, MA 02655
  • 268 Bumps River Rd, Osterville, MA 02655
    268 Bumps River Rd, Osterville, MA 02655
    268 Bumps River Rd, Osterville, MA 02655
    /33

    $605,000 Open Sat 11AM - 12PM

    • 2 Beds
    • 1 Bath
    • 1,179 Sq Ft

    268 Bumps River Rd, Osterville, MA 02655

    Welcome to this charming ranch in Osterville, one of Cape Cod's most coveted villages south of Route 28. This 2 bedroom (with passing 3 BR septic design) and 1 bath home features hardwood floors, a renovated kitchen with quartz countertops and stainless appliances, and a partially finished basement with family room, laundry, and space for overflow guests. Enjoy modern comforts with new central

    Christine Richards Kinlin Grover Compass

    268 Bumps River Rd, Osterville, MA 02655
  • 199 E Bay Rd Unit 13, Osterville, MA 02655
    199 E Bay Rd Unit 13, Osterville, MA 02655
    199 E Bay Rd Unit 13, Osterville, MA 02655
    /49

    $1,895,000 Open Sat 11AM - 1PM

    • 3 Beds
    • 3.5 Baths
    • 3,551 Sq Ft

    199 E Bay Rd Unit 13, Osterville, MA 02655

    Rarely available, this Cape Cod-style townhome in The Cove at East Bay offers low-maintenance living just minutes from Osterville Village shops, dining, and Dowses Beach. The main level features hardwood floors, a tray-ceilinged living room with bay window, gas fireplace, and custom millwork. Rich trim and transom windows frame the formal dining room. The granite kitchen with stainless appliances

    Susan Crasnick Sotheby's International Realty

    199 E Bay Rd Unit 13, Osterville, MA 02655
  • 920 Main St Unit 1 Building 2, Osterville, MA 02655
    920 Main St Unit 1 Building 2, Osterville, MA 02655
    920 Main St Unit 1 Building 2, Osterville, MA 02655
    /36

    $615,000

    • 2 Beds
    • 2 Baths
    • 1,150 Sq Ft

    920 Main St Unit 1 Building 2, Osterville, MA 02655

    Wouldn't you just love to have one of Cape Cod's most charming Main Streets at your front door? Osterville, the place to enjoy shopping, dining, and small village community all year round. This lovingly updated condo in Osterville Village is just the place for you. One floor living at it's best. Step through the main entry directly into your 2 bed, 2 bath, ranch style home. Gleaming hardwoods,

    Madeline Lacroix Keller Williams Realty

    920 Main St Unit 1 Building 2, Osterville, MA 02655
  • 920 Main St Unit 2-1, Osterville, MA 02655
    920 Main St Unit 2-1, Osterville, MA 02655
    920 Main St Unit 2-1, Osterville, MA 02655
    /35

    $615,000

    • 2 Beds
    • 2 Baths
    • 1,150 Sq Ft

    920 Main St Unit 2-1, Osterville, MA 02655

    Osterville, the place to enjoy shopping, dining, and small village community all year round. This lovingly updated condo in Osterville Village is just the place for you. One floor living at it's best. Step through the main entry directly into your 2 bed, 2 bath, ranch style home. Gleaming hardwoods, fresh paint, new appliances and windows, beautiful built ins, and wood burning fireplace. The

    Madeline Lacroix Keller Williams Realty

    920 Main St Unit 2-1, Osterville, MA 02655
  • 77 Robbins St, Osterville, MA 02655
    77 Robbins St, Osterville, MA 02655
    77 Robbins St, Osterville, MA 02655
    /46

    $1,395,000

    • 4 Beds
    • 2.5 Baths
    • 2,976 Sq Ft

    77 Robbins St, Osterville, MA 02655

    Lovely and spacious home in the sought-after village of Osterville. Ideally located just .03 miles to shops and restaurants and less than a mile to the warm waters of Dowses Beach on Nantucket Sound. This well-cared-for property offers an excellent rental history and is being sold fully furnished, ready for immediate enjoyment or as a continued investment opportunity. With over 2,900 sq. ft. of

    Deb Kenney Berkshire Hathaway HomeServices Robert Paul Properties

    77 Robbins St, Osterville, MA 02655
  • 44 Avalon Cir, Osterville, MA 02655
    44 Avalon Cir, Osterville, MA 02655
    44 Avalon Cir, Osterville, MA 02655
    /42

    $1,295,000

    • 3 Beds
    • 2 Baths
    • 3,387 Sq Ft

    44 Avalon Cir, Osterville, MA 02655

    On a quiet cul-de-sac in Osterville, this contemporary Cape blends architectural charm with a resort-inspired lifestyle. The backyard is the piece de resistance, with a sparkling pool, expansive deck, and gazebo framed by mature landscaping—perfect for entertaining or retreat. Inside, renovations highlight wood floors, exposed beam ceilings, and brick hearth fireplaces, creating warmth and

    Anthony Guthrie Berkshire Hathaway HomeServices Robert Paul Properties

    44 Avalon Cir, Osterville, MA 02655
  • 177 Bayview Cir, Osterville, MA 02655
    177 Bayview Cir, Osterville, MA 02655
    177 Bayview Cir, Osterville, MA 02655
    /40

    $899,900 Open Sun 11AM - 12:30PM

    • 3 Beds
    • 2.5 Baths
    • 2,050 Sq Ft

    177 Bayview Cir, Osterville, MA 02655

    Enjoy all that Osterville has to offer! This adorable 3 bedroom, 3 bath Cape is in the perfect village setting. This home has hardwood floors, an updated eat in kitchen, first floor primary with bath and private deck, large,bright, heated sunroom, first floor laundry, whole house generator, newer windows, and a finished lower level with a walk out basement; great for an in-law suite or other

    Kathleen Craig Berkshire Hathaway HomeServices Robert Paul Properties

    177 Bayview Cir, Osterville, MA 02655
  • 81 Falling Leaf Ln, Osterville, MA 02655
    81 Falling Leaf Ln, Osterville, MA 02655
    81 Falling Leaf Ln, Osterville, MA 02655
    /52

    $1,225,500

    • 3 Beds
    • 2.5 Baths
    • 2,776 Sq Ft

    81 Falling Leaf Ln, Osterville, MA 02655

    Welcome to this finely crafted custom Cape, set in one of Osterville's desirable locations. Designed with sophistication & comfort in mind, the home showcases sun-filled, spacious rooms, elegant molding, & timeless hardwood flooring throughout.The first floor offers a front foyer, an open kitchen with walk-in pantry, island and dining area, and a formal dining room perfect for gatherings. French

    Linda Whitcomb William Raveis Real Estate & Home Services

    81 Falling Leaf Ln, Osterville, MA 02655
  • 16 2nd Ave Unit 5A, Osterville, MA 02655
    16 2nd Ave Unit 5A, Osterville, MA 02655
    16 2nd Ave Unit 5A, Osterville, MA 02655
    /21

    $588,000

    • 1 Bed
    • 1 Bath
    • 720 Sq Ft

    16 2nd Ave Unit 5A, Osterville, MA 02655

    Tucked along picturesque Parker Road, between the Osterville Historical Museum and Wianno Golf Course, the beloved Aunt Tempy's Cottages capture the essence of Cape & Islands living - weathered shingles, crisp white trim, and beautifully kept grounds. This historic 10-unit association offers a lovely blend of character and convenience, all within steps of the village. Unit 5A underwent a full

    Shaelyn Hegarty Frank A Sullivan Real Estate

    16 2nd Ave Unit 5A, Osterville, MA 02655
  • 89 Swift Ave, Osterville, MA 02655
    89 Swift Ave, Osterville, MA 02655
    89 Swift Ave, Osterville, MA 02655
    /59

    $1,175,000 Open Sat 11AM - 2PM

    • 4 Beds
    • 2 Baths
    • 2,674 Sq Ft

    89 Swift Ave, Osterville, MA 02655

    OPPORTUNITY AWAITS! This four bedroom, two bath ranch home offers incredible potential in one of the areas most desirable neighborhoods! Set on a spacious lot with mature trees and established landscaping, the property combines location, space and vision for the next owner!This home presents a rare chance to create a residence that truly reflects your style. Generous room sizes, high ceilings, a

    Laurie Jacobson eXp Realty, LLC

    89 Swift Ave, Osterville, MA 02655
  • 435 Old Mill Rd, Osterville, MA 02655
    435 Old Mill Rd, Osterville, MA 02655
    435 Old Mill Rd, Osterville, MA 02655
    /25

    $769,000

    • 3 Beds
    • 2 Baths
    • 1,700 Sq Ft

    435 Old Mill Rd, Osterville, MA 02655

    Tucked at the end of a long shell driveway, this Osterville ranch combines Cape Cod charm with modern updates. Privately situated on a .75-acre lot abutting acres of town owned land, it offers peace, nature, and walkability to Village shops and dining, plus Dowses Beach is just minutes away. Perfect for indoor-outdoor living with an expansive deck, large back yard, outdoor shower and wooded

    Michael Fratalia NextHome Signature Realty

    435 Old Mill Rd, Osterville, MA 02655
  • Lot 289 Seapuit River Road B, Barnstable, MA 02655
    Lot 289 Seapuit River Road B, Barnstable, MA 02655
    Lot 289 Seapuit River Road B, Barnstable, MA 02655
    /10

    $3,000,000

    • Land
    • 2.08 Acres
    • $1,442,308 per Acre

    Lot 289 Seapuit River Road B, Barnstable, MA 02655

    A wonderful opportunity to build in a premier location within Oyster Harbors, a private gated golf community on Cape Cod's southern shore. Set in the desirable village of Osterville—home to some of the Cape's most prestigious estates—this 2.08-acre level, wooded lot offers the perfect backdrop for creating an exclusive and private retreat. For those seeking expanded grounds or multi-generational

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    Lot 289 Seapuit River Road B, Barnstable, MA 02655
  • Lot 288 Seapuit River Rd A, Barnstable, MA 02655
    Lot 288 Seapuit River Rd A, Barnstable, MA 02655
    Lot 288 Seapuit River Rd A, Barnstable, MA 02655
    /9

    $3,100,000

    • Land
    • 2.3 Acres
    • $1,347,826 per Acre

    Lot 288 Seapuit River Rd A, Barnstable, MA 02655

    Located in the heart of Oyster Harbors - Cape Cod's premier golf community - this 2.3-acre lot presents an outstanding opportunity to create a legacy estate. Set within the highly sought after village of Osterville, known for its timeless charm and distinguished properties, this expansive parcel offers ample space to design a custom estate with room for a main house, guest, house, pool and pool

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    Lot 288 Seapuit River Rd A, Barnstable, MA 02655
  • Lot 289 Seapuit River B Rd, Osterville, MA 02655
    Lot 289 Seapuit River B Rd, Osterville, MA 02655
    Lot 289 Seapuit River B Rd, Osterville, MA 02655
    /10

    $3,000,000

    • Land
    • 2.08 Acres
    • $1,442,308 per Acre

    Lot 289 Seapuit River B Rd, Osterville, MA 02655

    A wonderful opportunity to build in a premier location within Oyster Harbors, a private gated golf community on Cape Cod's southern shore. Set in the desirable village of Osterville--home to some of the Cape's most prestigious estates--this 2.08-acre level, wooded lot offers the perfect backdrop for creating an exclusive and private retreat. For those seeking expanded grounds or

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    Lot 289 Seapuit River B Rd, Osterville, MA 02655
  • Lot 288 Seapuit River A Rd, Osterville, MA 02655
    Lot 288 Seapuit River A Rd, Osterville, MA 02655
    Lot 288 Seapuit River A Rd, Osterville, MA 02655
    /9

    $3,100,000

    • Land
    • 2.3 Acres
    • $1,347,826 per Acre

    Lot 288 Seapuit River A Rd, Osterville, MA 02655

    Located in the heart of Oyster Harbors - Cape Cod's premier golf community - this 2.3-acre lot presents an outstanding opportunity to create a legacy estate. Set within the highly sought after village of Osterville, known for its timeless charm and distinguished properties, this expansive parcel offers ample space to design a custom estate with room for a main house, guest, house, pool and pool

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    Lot 288 Seapuit River A Rd, Osterville, MA 02655
  • 37 Old Salem Way, Osterville, MA 02655
    37 Old Salem Way, Osterville, MA 02655
    37 Old Salem Way, Osterville, MA 02655
    /49

    $835,000

    • 3 Beds
    • 2.5 Baths
    • 1,688 Sq Ft

    37 Old Salem Way, Osterville, MA 02655

    Take in the charming vibe of Osterville Village.Relax in the spacious living room with cathedral ceilings & sliding doors to a large back patio - perfect for outdoor enjoyment. The inviting eat-in kitchen is ideal for gatherings. Three bedrooms on the main level include a primary suite with a convenient half bath. A full bathroom with tub/shower serves the main floor. Ascend the solid-wood wide

    Linda Whitcomb William Raveis Real Estate & Home Services

    37 Old Salem Way, Osterville, MA 02655
  • 71 Sand Point, Osterville, MA 02655
    71 Sand Point, Osterville, MA 02655
    71 Sand Point, Osterville, MA 02655
    /45

    $12,250,000

    • 5 Beds
    • 6 Baths
    • 5,747 Sq Ft

    71 Sand Point, Osterville, MA 02655

    Exquisite Waterfront Estate in Exclusive Oyster Harbors: Experience the pinnacle of coastal luxury with this magnificent Cape Cod waterfront estate, nestled in the prestigious gated community of Oyster Harbors. Boasting 450 feet of pristine water frontage with a private beach and breathtaking views over Cotuit Bay and North Bay, this property offers spectacular sunsets, an elegant coastal

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    71 Sand Point, Osterville, MA 02655
  • 501 Eel River Rd, Osterville, MA 02655
    501 Eel River Rd, Osterville, MA 02655
    501 Eel River Rd, Osterville, MA 02655
    /50

    $10,500,000

    • 6 Beds
    • 9 Baths
    • 8,203 Sq Ft

    501 Eel River Rd, Osterville, MA 02655

    Discover the epitome of luxury living in this custom-designed waterfront estate, featuring breathtaking views of Eel River and Nantucket Sound. Located in the village of Osterville and set on an expansive and beautifully landscaped 2.4-acre lot, this stunning residence features over 8,000 square feet of meticulously crafted living space with rich details, modern comforts and extraordinary views.

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    501 Eel River Rd, Osterville, MA 02655
  • 25 Oyster Way, Barnstable, MA 02655
    25 Oyster Way, Barnstable, MA 02655
    25 Oyster Way, Barnstable, MA 02655
    /51

    $10,450,000

    • 5 Beds
    • 4.5 Baths
    • 7,157 Sq Ft

    25 Oyster Way, Barnstable, MA 02655

    Located within the private, gated golf community of Oyster Harbors, in the village of Osterville, is this magnificent five-bedroom waterfront residence with an in-ground pool and deep-water dock. This beautiful residence has the look and feel of a European estate with an open floor plan design and beautiful water vistas. Refined architectural details set the tone in this grand home with 7,157 sq.

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    25 Oyster Way, Barnstable, MA 02655
  • 255 Bayberry Way, Osterville, MA 02655
    255 Bayberry Way, Osterville, MA 02655
    255 Bayberry Way, Osterville, MA 02655
    /44

    $8,950,000

    • 7 Beds
    • 6 Baths
    • 4,896 Sq Ft

    255 Bayberry Way, Osterville, MA 02655

    Welcome to ''Point House'' a spectacular 5.98-acre waterfront estate on a peninsula overlooking the glistening waters of West Bay. In a setting of unsurpassed beauty, the 4,896 square foot residence offers truly exceptional water vistas, beautiful gardens, an expansive private sandy beach, and a substantial deep-water dock from which you can sail into the waters of Nantucket Sound. The 6-bedroom

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    255 Bayberry Way, Osterville, MA 02655
  • 60 Smoke Valley Rd, Osterville, MA 02655
    60 Smoke Valley Rd, Osterville, MA 02655
    60 Smoke Valley Rd, Osterville, MA 02655
    /98

    $5,395,000 New Construction

    • 5 Beds
    • 5.5 Baths
    • 7,500 Sq Ft

    60 Smoke Valley Rd, Osterville, MA 02655

    Magnificent private shingle-style new construction home in Osterville's Seapuit area. Home has exquisite features both inside and out, including high-end fixtures, custom woodworking and cabinetry, gourmet kitchen with panoramic breakfast nook, media room, and elevator to all three stores are just to name a few. Landscaping with salt-water pool, pergola, patio, fireplace, outdoor kitchen and

    Gail Germain Martis Sotheby's International Realty

    60 Smoke Valley Rd, Osterville, MA 02655
Massachusetts Barnstable County Barnstable Osterville

Real Estate & Homes for Sale in Osterville, Barnstable

Why Live in Osterville
Osterville, a village in Barnstable, MA, has evolved from a shipbuilding and oystering community into a luxury summer destination. With 5 miles of shoreline along Nantucket Sound and 17 miles of bayfront coast, residents and visitors enjoy ample opportunities for sailing, kayaking, fishing, and swimming. Dowses Beach, exclusive to Barnstable residents, offers a sandy retreat, while Armstrong-Kelley Park provides wooded walking paths and a children's garden. The village features two private golf courses, Wianno Golf Club and Oyster Harbors Club, as well as public tennis and pickleball courts. Osterville's walkable downtown area boasts high-end boutiques, art galleries, and long-standing markets like Fancy's Market and Wimpy's Seafood Cafe & Market. Dining options include Crisp for flatbread pizza and North Sister Café for vegetarian and gluten-free meals. The Osterville Village Library and Village Association host numerous events, particularly in the summer, including the annual Summer Soiree and Osterville Village Day. Housing ranges from mid-1900s ranch-style homes to multi-million-dollar waterfront residences, with traditional Cape Cods and Dutch Colonial-style homes prevalent. The area is served by Barnstable Public Schools, with highly rated options like West Villages Elementary School and Barnstable High School, as well as private institutions such as Cape Cod Academy and Falmouth Academy. While Osterville enjoys a lower crime risk compared to the national average, residents face environmental concerns, including the transition to sewer systems and the proposed Avangrid wind farm. State Route 28 and the Cape Cod Regional Transit Authority provide transportation options, with Hyannis 6 miles away offering further connections.
Learn more about living in Osterville

Frequently Asked Questions

Is Osterville a good place to live?
Osterville is a good place to live. Osterville is considered car-dependent and somewhat bikeable with minimal transit options. Osterville has 1 park for recreational activities. It has a median age of 58. The average household income is $141,161 which is above the national average. College graduates make up 56.1% of residents. A majority of residents in Osterville are home owners, with 14.4% of residents renting and 85.6% of residents owning their home. A local real estate agent serving Osterville can help you decide if this neighborhood is the right one for you. Learn more on our Osterville neighborhood guide.
How much do you need to make to afford a house in Osterville?
The median home price in Osterville is $1,495,000. If you put a 20% down payment of $299,000 and had a 30-year fixed mortgage with an interest rate of 6.22%, your estimated principal and interest payment would be $7,340 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $315K a year to afford the median home price in Osterville. The average household income in Osterville is $141K.
What are the best public schools in Osterville?
The best public schools that serve Osterville are:
What are the best private schools in Osterville?
The best private schools that serve Osterville are:
What are the most popular zip codes in Osterville, Barnstable, MA?
The most popular zip codes in Osterville, Barnstable, MA include 02655, 02648, 02635, 02632 and 02630.
What are the most popular neighborhoods near Osterville, Barnstable, MA?
The most popular neighborhoods near Osterville, Barnstable, MA are Marstons Mills, Cotuit, Centerville, Mashpee Neck and West Barnstable.
Are home prices dropping in Osterville?
Yes, home prices in Osterville are down 22% in the last 12 months.

Home Trends in Osterville, MA

On average, homes in Osterville, Barnstable sell after 56 days on the market compared to the national average of 53 days. The median sale price for homes in Osterville, Barnstable over the last 12 months is $1,350,000, up 30% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price
$1,350,000
Median Single Family Sale Price
$1,500,000
Median 2 Bedroom Sale Price
$612,500
Median 1 Bedroom Sale Price
$599,500
Average Price Per Sq Ft
$832
Number of Homes for Sale
31
Last 12 months Home Sales
112
Months of Supply
3.30
Median List Price
$1,495,000
Median Change From 1st List Price
4%
Median Home Sale Price YoY Change
30%
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