Homes for Sale in 02655

/40
$795,000
- 3 Beds
- 2 Baths
- 1,248 Sq Ft
111 Westwind Cir, Osterville, MA 02655

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

Witter & Witter Boston/Cape Cod Compass

111 Westwind Cir, Osterville, MA 02655
/21
$2,700,000
- 4 Beds
- 3 Baths
- 2,050 Sq Ft
72 Hathaway Rd, Osterville, MA 02655

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

Tom Foley The Foley Company

72 Hathaway Rd, Osterville, MA 02655
/22
$18,500,000
- 7 Beds
- 11 Baths
- 10,104 Sq Ft
47 Sunset Point, Barnstable, MA 02655

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

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

47 Sunset Point, Barnstable, MA 02655
/35
$4,250,000
- 3 Beds
- 3.5 Baths
- 2,721 Sq Ft
35 Blue Heron Dr, Osterville, MA 02655

Waterfront home in the heart of Osterville Village, where charming shops, restaurants, and amenities are just a short stroll away. Enjoy spectacular, unobstructed views, sunsets and frontage on the picturesque North Bay- all this and room for a pool. This meticulously maintained and beautifully appointed home is move-in ready, offering the perfect opportunity to enjoy immediately or create your

Tom Foley The Foley Company

35 Blue Heron Dr, Osterville, MA 02655
/47
$4,950,000
- 5 Beds
- 7.5 Baths
- 5,970 Sq Ft
313 Bridge St, Osterville, MA 02655

Representing the pinnacle of coastal elegance, this extraordinary estate on Little Island offers a rare opportunity for a generational compound in mint condition and an unsurpassed location. Finished to the highest standards, the property features a spectacular five-bedroom main residence, a swimming pool, a pool house with kitchenette and full bath, and a detached three-car garage with a home

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

313 Bridge St, Osterville, MA 02655
/38
$849,900

$19K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,100 Sq Ft
177 Bayview Cir, Osterville, MA 02655

Wow what a rare opportunity to purchase an AFFORDABLE turnkey Quintessential Year-Round Cape within.5 mile of Osterville Village and 1 mile to Dowes Beach. The size of the house can be deceiving from the front elevation. Here are the details of the ~2100 sqft of living space. Main level of ~1150 sqft includes a primary suite, guest bedroom, 2 full baths, living room, E/I kitchen and sun porch.

Derek Greene The Greene Realty Group

177 Bayview Cir, Osterville, MA 02655
/24
$642,000

$23K PRICE DROP
- 3 Beds
- 2.5 Baths
- 1,297 Sq Ft
17 Galleon Way, Osterville, MA 02655

Welcome to 17 Galleon Way, a charming Osterville ranch offering the perfect blend of comfort, versatility, and Cape Cod living. The main home features a beautifully renovated kitchen, two bedrooms and one and a half baths, all thoughtfully designed for easy one-level living. Main home is 864 sq ft. An attached garage adds everyday convenience and additional storage.A standout feature of

Corinne Costanzo Berkshire Hathaway HomeServices Robert Paul Properties

17 Galleon Way, Osterville, MA 02655
/36
$725,000

$35K PRICE DROP
- 3 Beds
- 1.5 Baths
- 1,008 Sq Ft
84 Hinckley Cir, Osterville, MA 02655

Move-in ready and offered for the first time in generations, this charming one-level ranch is ideally located in the heart of Osterville Village. Just 1.5 miles to beautiful Dowses Beach, an 8-minute drive to sought-after Craigville Beach, and only 0.4 miles to the crystal-clear waters of Joshua Pond. This inviting “Cape Cod Escape” features 3 bedrooms and 1.5 baths, offering easy single-floor

Chelsea McLaughlin RE/MAX Legacy

84 Hinckley Cir, Osterville, MA 02655
/41
$1,300,000
- 3 Beds
- 4 Baths
- 3,355 Sq Ft
175 Hickory Hill Cir, Osterville, MA 02655

Offered for the first time! 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 landscaping shines in every season! 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

Michelle Curran

175 Hickory Hill Cir, Osterville, MA 02655
/40
$9,500,000

$1M PRICE DROP
- 5 Beds
- 6 Baths
- 7,157 Sq Ft
25 Oyster Way, Barnstable, MA 02655

Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

25 Oyster Way, Barnstable, MA 02655
/56
$9,500,000

$1M PRICE DROP
- 5 Beds
- 6 Baths
- 7,157 Sq Ft
25 Oyster Way, Barnstable, MA 02655

Set behind the gates of Oyster Harbors, Cape Cod's most exclusive private golf and waterfront community, this extraordinary waterfront estate offers an exceptional blend of architectural elegance, privacy, and coastal luxury. Perfectly sited on 1.65 acres along the water's edge, the property enjoys sweeping water views, a deep-water dock, an in-ground pool, and meticulously landscaped grounds

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

25 Oyster Way, Barnstable, MA 02655
/37
$649,000
- 2 Beds
- 2 Baths
- 1,808 Sq Ft
295 Westwind Cir, Osterville, MA 02655

Nestled in a neighborhood south of Route 28, this charming Osterville ranch offers the perfect blend of classic Cape Cod character & modern comfort. Before you even step inside, a private front patio welcomes you, the ideal spot for a pair of Adirondack chairs. The interior has been thoughtfully reimagined for contemporary living w/ a bright open concept layout. Upon entry, you're greeted by a

Cynthia Crawford Compass Massachusetts, LLC

295 Westwind Cir, Osterville, MA 02655
/42
$8,625,000
- 7 Beds
- 7.5 Baths
- 7,315 Sq Ft
63 Main St, Osterville, MA 02655

Legacy estate set prominently on one of the highest Osterville bluffs delivers classic waterfront expectations with a superior dock and substantial dynamic views from the Vineyard to Hyannisport. The grand yesteryear home constructed in 1920 conveys the qualities of that oceanfront era, with higher ceilings, multiple great rooms, and the character of hidden porches, exclusive balconies, and

Christa Zevitas Berkshire Hathaway HomeServices Robert Paul Properties

63 Main St, Osterville, MA 02655
/59
$4,995,000

New Construction
- 5 Beds
- 7 Baths
- 4,100 Sq Ft
22 Scudder Rd, Osterville, MA 02655

Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is

Sean Dacey Coldwell Banker Realty

22 Scudder Rd, Osterville, MA 02655
/57
$1,395,000
- 4 Beds
- 4 Baths
- 2,359 Sq Ft
18 Calico Ln, Osterville, MA 02655

Osterville Oasis...Tucked away at the end of a quiet, tree-lined lane, this beautifully renovated Cape-style home offers the perfect blend of classic charm with modern updates in highly desirable Oyster Hills West. The first floor features a spacious Primary Suite with a private bath, overlooking a lushly landscaped, private backyard. The inviting Living Room showcases custom built-ins and a

Chuck Tuttle William Raveis Real Estate & Home Services

18 Calico Ln, Osterville, MA 02655
/28
$764,000

$20K PRICE DROP
- 3 Beds
- 2 Baths
- 1,426 Sq Ft
114 King Arthur Dr, Barnstable, MA 02601

Welcome to this beautifully updated 3-bedroom, 2-bath Cape-style home in the coastal village of Osterville. Situated on a large corner lot in a neighborhood setting, this property is move-in ready and features a brand-new kitchen, new stainless appliances, backsplash and granite countertops. A fireplace living room for cool nights and a dining room with sliders to a spacious deck ideal for

Christine Case C. Case Realty, LLC

114 King Arthur Dr, Barnstable, MA 02601
/30
$764,000

$20K PRICE DROP
- 3 Beds
- 2 Baths
- 1,426 Sq Ft
114 King Arthur Dr, Osterville, MA 02655

Welcome to this 3 bedroom, 2 bath Cape-style home in the coastal village of Osterville, situated on a corner lot in a neighborhood setting. This property features new kitchen cabinets, new stainless appliances, backsplash and granite countertops. A fireplace living room to enjoy on cool nights and a dining room with sliders to a spacious deck with a gas hookup for grilling, ideal for entertaining

Christine Case C. Case Realty, LLC

114 King Arthur Dr, Osterville, MA 02655
/46
$1,995,000
- 4 Beds
- 2.5 Baths
- 2,636 Sq Ft
420 Starboard Ln, Osterville, MA 02655

In Osterville, certain streets make the most of Village living. Starboard Lane, winding along the western shore of the Bumps River, is among the village's most coveted addresses. Known for gracious homes with exceptional privacy on large parcels, the convenience to the heart of Osterville is a huge plus. 420 Starboard Lane captures the Village vibe wonderfully. Set on 1.68 acres, this

Jack Cotton, Jr Sotheby's International Realty

420 Starboard Ln, Osterville, MA 02655
/41
$11,950,000
- 6 Beds
- 8 Baths
- 8,387 Sq Ft
48 Starboard Ln, Osterville, MA 02655

Newly constructed and ready to enjoy, this exceptional waterfront estate on the Bumps River represents the finest of Cape Cod living. Combining an unrivaled setting with state-of-the-art luxury, the property features a resort-like swimming pool and cabana, a boathouse with a float for non-motorized crafts, and a deeded beach lot on Long Beach. The open floor plan seamlessly flows from a

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

48 Starboard Ln, Osterville, MA 02655
/85
$3,500,000
- 4 Beds
- 4.5 Baths
- 5,049 Sq Ft
140 Seapuit Rd, Osterville, MA 02655

Nestled within the prestigious enclave of Seapuit, this architectural masterpiece represents a rare synergy of design and craftsmanship spanning over 5,000SF of meticulously curated space. A collaboration between renowned architect Doreve Nicholaeff & the master builders at Sylvia & Sylvia, the residence is an exercise in sophisticated coastal living. The home is set on a two-acre private oasis,

Rick Shechtman Kinlin Grover Compass

140 Seapuit Rd, Osterville, MA 02655
/60
$3,450,000
- 4 Beds
- 5 Baths
- 3,924 Sq Ft
156 E Bay Rd, Osterville, MA 02655

Prime location on one of Cape Cod's most coveted roads, East Bay Road in Osterville. This beautiful home is rich with character, having been repurposed from a large carriage house. It boasts history and classic Cape Cod charm. Enter the home through the large living room and move into the kitchen equipped with a bright sunroom off to the right. An old horse stable has been fashioned into an

Barbara Corcoran William Raveis Real Estate & Home Services

156 E Bay Rd, Osterville, MA 02655
/32
$5,950,000
- 5 Beds
- 8 Baths
- 8,740 Sq Ft
179 Pineleigh Path, Barnstable, MA 02655

Overlooking the golf course within the coveted gated community of Oyster Harbors, this exceptional residence combines timeless design with modern comforts in a beautifully crafted coastal setting. The home is defined by generous proportions, abundant natural light, and refined architectural detail throughout. The kitchen is tailored for both everyday living and entertaining, offering high-end

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

179 Pineleigh Path, Barnstable, MA 02655
/31
$689,000
- 2 Beds
- 2 Baths
- 1,198 Sq Ft
727 Main St Unit F3, Osterville, MA 02655

Just in time for summer comes this bright, stylishly updated second-floor condo in a prime Osterville village setting. Thoughtfully renovated with wood floors and an open-concept floorplan, everything you need for effortless seaside living is here. The eat-in kitchen features stone countertops, stainless steel appliances, island and built-in banquette, with French doors opening to a charming

Debra Caney Sotheby's International Realty

727 Main St Unit F3, Osterville, MA 02655
/38
$7,500,000

$1M PRICE DROP
- 3 Beds
- 6 Baths
- 4,831 Sq Ft
46 Great Bay Rd, Osterville, MA 02655

Nestled along the sparkling shores of North Bay in the heart of Osterville, this exceptional Waterfront Estate delivers timeless beauty and relaxed elegance. Wake each morning to sweeping water views and ocean breezes, step onto your boat from the Substantial Dock. Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence is thoughtfully designed to blend coastal charm with

Chuck Tuttle William Raveis R.E. & Home Services

46 Great Bay Rd, Osterville, MA 02655
/46
$599,900
- 2 Beds
- 1.5 Baths
- 1,088 Sq Ft
727 Main St Unit B1, Osterville, MA 02655

RARE to market! First opportunity in YEARS in Osterville's sought after Wianno Knoll. Nestled in the heart of Osterville village this desirable first floor condo has it all! Gorgeous open floor plan features two spacious bedrooms, a completely updated full bath and charming guest half bath. Renovated open kitchen with pantry closet, stainless appliances. and sliders leading to private back porch

Gregory W Nowak Craigville Realty Co

727 Main St Unit B1, Osterville, MA 02655
/49
$649,000

$50K PRICE DROP
- 2 Beds
- 2 Baths
- 1,040 Sq Ft
55 Seth Goodspeed Way, Osterville, MA 02655

Incredible value at this new price in Osterville Heights!! Move right into this sun-filled, open-concept ranch with one-car garage and oversized shed set on a private and spacious partially-fenced park-like backyard perfect for adding a potential pool, outdoor entertaining, barbecues, lawn games and relaxing with family and friends. New improvements include enhanced landscaping, fresh paint, new

Donna Christopher Sotheby's International Realty

55 Seth Goodspeed Way, Osterville, MA 02655
/41
$2,950,000
- 3 Beds
- 3 Baths
- 3,178 Sq Ft
12 Cockachoiset, Osterville, MA 02655

Located in the heart of Osterville - one of Cape Cod's most desirable seaside villages along Nantucket Sound - 12 Cockachoiset, known as the iconic ''Windmill House,'' offers a distinctive blend of coastal charm and architectural character. Recognized for its unique two-story windmill adorned with seaside murals, the home features a balcony with water views and serves as a memorable focal point

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

12 Cockachoiset, Osterville, MA 02655
/40
$2,950,000
- 3 Beds
- 3 Baths
- 3,178 Sq Ft
12 Cockachoiset Ln, Barnstable, MA 02655

Located in the heart of Osterville - one of Cape Cod's most desirable seaside villages along Nantucket Sound - 12 Cockachoiset, known as the iconic ''Windmill House,'' offers a distinctive blend of coastal charm and architectural character. Recognized for its unique two-story windmill adorned with seaside murals, the home features a balcony with water views and serves as a memorable focal point

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

12 Cockachoiset Ln, Barnstable, MA 02655
/38
$1,850,000

$100K PRICE DROP
- 3 Beds
- 2.5 Baths
- 3,084 Sq Ft
81 Osterville West Barnstable Rd, Osterville, MA 02655

This elegant Cape-style residence offers a refined retreat on a sprawling, wooded lot near Osterville Village and Dowses Beach. Defined by bright, voluminous spaces, the home features a stately pillared portico, stone walkways, and classic shingle siding. Inside, the center hall layout leads to a grand living room with a two-story wall of windows and a Palladian arch. This flows into the dining

Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

81 Osterville West Barnstable Rd, Osterville, MA 02655
/42
$1,685,000

$100K PRICE DROP
- 3 Beds
- 2.5 Baths
- 2,048 Sq Ft
162 Main St, Osterville, MA 02655

New Driveway Entrance and front yard redesigned!!!! Fall in love the moment you step inside this beautifully renovated home that feels brand new in every way. Sunlight fills the space throughout the day, drawing your eye to tranquil pond views and the surrounding natural beauty that create an immediate sense of calm and privacy. Thoughtfully redesigned with modern amenities, this home offers

Kimberly Gazal Santos Property Cape Cod

162 Main St, Osterville, MA 02655
/57
$1,500,000

Open Sun 12PM - 2PM $79K PRICE DROP
- 3 Beds
- 2 Baths
- 1,765 Sq Ft
955 Main St, Osterville, MA 02655

A mid-19th-century Greek Revival, believed to be the birthplace of Captain William Bradford Parker and later home to Samuel Hallett -- both tied to Osterville's historic maritime corridor along Main Street. The property reflects the success of maritime captains - there's a reason Osterville was once described as ''a place where retired sea captains can live like gentlemen.'' You feel that here.

Karen Lilly Property Cape Cod

955 Main St, Osterville, MA 02655
/27
$4,495,000

$300K PRICE DROP
- 4 Beds
- 4 Baths
- 4,964 Sq Ft
93 Oyster Way, Barnstable, MA 02655

Tucked within the gated enclave of Oyster Harbors, 93 Oyster Way blends timeless coastal elegance with modern luxury. Designed for both everyday living and entertaining, the home offers sun-filled interiors with vaulted ceilings and rich hardwood floors. Formal living and dining rooms provide inviting gathering spaces with serene backyard views.At the heart of the home, the chef's kitchen

Kelly Crosby LandVest, Inc.

93 Oyster Way, Barnstable, MA 02655
/15
$775,000

$35K PRICE DROP
- 2 Beds
- 2 Baths
- 1,144 Sq Ft
441 Old Mill Rd, Osterville, MA 02655

This is the Osterville opportunity you've been waiting for. A sprawling 1.4 acre lot that borders conservation land, this is a canvas for your Cape Cod vision. You're just moments from the heart of Osterville's iconic village center, where you can spend afternoons browsing boutique shops or enjoying delightful dining at one of the local eateries. When the sun is shining, the pristine sands of

Diane Boudreau Kinlin Grover Compass

441 Old Mill Rd, Osterville, MA 02655
/29
$875,000
- 3 Beds
- 2 Baths
- 1,497 Sq Ft
5 Briar Patch Rd, Osterville, MA 02655

South of Route 28 in Osterville village, this inviting property offers an outstanding opportunity to secure your place in one of the area's most sought-after locations. Just 1 mile from Main Street, you'll enjoy easy access to restaurants, shops, beaches and everyday conveniences that make village living so special. Inside the home features a bright living room with vaulted ceilings, a first

Adam Marks Berkshire Hathaway HomeServices Robert Paul Properties

5 Briar Patch Rd, Osterville, MA 02655
/40
$7,995,000

$2M PRICE DROP
- 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 dramatic

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

168 Garrison Ln, Osterville, MA 02655
/43
$9,850,000

$650K PRICE DROP
- 5 Beds
- 5 Baths
- 3,087 Sq Ft
14 Indian Trail, Osterville, MA 02655

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, Osterville, MA 02655
/42
$9,850,000

$650K PRICE DROP
- 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
/68
$7,750,000

$250K PRICE DROP
- 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 two-bedroom guest house, and a spa-inspired pool area, the property offers a rare blend of timeless elegance and contemporary luxury. A gracious covered front porch

Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

440 Grand Island Dr, Osterville, 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
/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

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