Osterville Homes for Sale

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  /43

  $999,000

  • 2 Beds
  • 2.5 Baths
  • 1,564 Sq Ft

  16 2nd Ave Unit 4, Osterville, MA 02655

  LIKE-NEW IN OSTERVILLE'S COVETED WIANNO AREA! Rare opportunity to own a free-standing Osterville 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. Natural light pours through the open, airy interior

  

  Livia Freitas Monteforte

  Compass Massachusetts, LLC

  16 2nd Ave Unit 4, Osterville, MA 02655
• Explore Osterville

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  /46

  $1,485,000

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  23 & 27 Swift Ave, Osterville, MA 02655

  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

  

  Livia Freitas Monteforte

  Compass Massachusetts, LLC

  23 & 27 Swift Ave, Osterville, MA 02655
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  /42

  $1,485,000

  • 3 Beds
  • 2.5 Baths
  • 1,844 Sq Ft

  23 Swift Ave, Osterville, MA 02655

  Beautifully renovated, 23 & 27 Swift Avenue is a rare two-parcel Osterville offering totaling approximately 1.11 acres, moments from Osterville Village. The charming 3-bedroom residence sits on approximately .66 acre and 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

  

  Livia Freitas Monteforte

  Compass

  23 Swift Ave, Osterville, MA 02655
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  /41

  $999,000

  • 2 Beds
  • 2.5 Baths
  • 1,564 Sq Ft

  16 Second Unit 4, Barnstable, MA 02655

  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

  

  Livia Freitas Monteforte

  Compass

  16 Second Unit 4, Barnstable, MA 02655
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  /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
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  /38

  $1,750,000

  $200K 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
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  /40

  $1,349,900

  • 3 Beds
  • 3 Baths
  • 2,126 Sq Ft

  30 Deerfield Rd, Osterville, MA 02655

  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

  Garrett Hogan Garland Group, LLC

  30 Deerfield Rd, Osterville, MA 02655
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  /49

  $634,900

  Open Sat 11AM - 12:30PM $64K 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
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  /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
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  /42

  $4,795,000

  $200K PRICE DROP

  • 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

  Jessica Quirk Coldwell Banker Realty - Boston

  22 Scudder Rd, Osterville, MA 02655
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  /27

  $724,000

  $60K 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
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  /27

  $4,045,500

  $750K 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 coastal elegance with modern luxury. Sunlit interiors feature vaulted ceilings, hardwood floors, and inviting living and dining spaces overlooking a private backyard. The chef’s kitchen offers custom cabinetry, granite countertops, a large island, and premium Wolf and Sub-Zero appliances, opening to a family room and screened

  Kelly Crosby LandVest, Inc.

  93 Oyster Way, Barnstable, MA 02655
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  /35

  $849,900

  Open Sun 1PM - 2:30PM

  • 2 Beds
  • 1.5 Baths
  • 1,055 Sq Ft

  466 Old Mill Rd, Osterville, MA 02655

  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

  Danny Griffin Griffin Realty Group

  466 Old Mill Rd, Osterville, MA 02655
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  /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
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  /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
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  /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
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  /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
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  /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
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  /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
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  /40

  $8,800,000

  $2M 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
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  /41

  $11,500,000

  $450K PRICE DROP

  • 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
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  /50

  $9,950,000

  $550K PRICE DROP

  • 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
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  /30

  $724,000

  $60K 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
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  /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
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  /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
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  /37

  $599,900

  • 2 Beds
  • 1.5 Baths
  • 1,088 Sq Ft

  727 Main St Unit B1, Osterville, MA 02655

  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......

  Gregory W Nowak Craigville Realty, Inc.

  727 Main St Unit B1, 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 multi-generational

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  Lot 289 Seapuit River B Rd, Osterville, MA 02655
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  /42

  $2,825,000

  • 4 Beds
  • 4 Baths
  • 3,523 Sq Ft

  55 Seapuit Rd, Osterville, MA 02655

  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

  Danny Griffin Griffin Realty Group

  55 Seapuit Rd, Osterville, MA 02655
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  /9

  $3,250,000

  • Land
  • 2.45 Acres
  • $1,326,531 per Acre

  30 Indian Trail, Osterville, MA 02655

  A premier opportunity to build in the exclusive gated community of Oyster Harbors, set in the heart of coveted Osterville on Cape Cod's southern shore. This sprawling 2.45-acre level, wooded parcel offers a serene and private setting—an ideal canvas to craft the ultimate estate complete with a main home, guest house, pool, and pool house. Adjoining properties are also available, presenting an

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  30 Indian Trail, Osterville, MA 02655
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  /39

  $990,000

  • 3 Beds
  • 2.5 Baths
  • 2,116 Sq Ft

  82 Falling Leaf Ln, Osterville, MA 02655

  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

  John Peacock Sotheby's International Realty

  82 Falling Leaf Ln, Osterville, MA 02655
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  /29

  $584,900

  • 3 Beds
  • 1 Bath
  • 746 Sq Ft

  1825 Main Street 6a, Barnstable, MA 02648

  This West Barnstable retreat earned a spot on HGTV's Houses With History. Creatively designed with memorable details at every turn, the kitchen pairs copper and quartz surfaces with a farmhouse sink, Bertazzoni gas range, and peninsula seating. A gas fireplace, painted floors, handcrafted lighting, and wood-clad ceilings give the interior its distinctive style. The main level offers a bedroom and

  Leighton Team Keller Williams Realty

  1825 Main Street 6a, Barnstable, MA 02648
• 

  

  /50

  $1,595,000

  $190K PRICE DROP

  • 3 Beds
  • 2.5 Baths
  • 2,048 Sq Ft

  162 Main St, Osterville, MA 02655

  New spacious front yard and entrance 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
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  /34

  $1,075,000

  $25K PRICE DROP Pending

  • 2 Beds
  • 2 Baths
  • 2,010 Sq Ft

  51 Falling Leaf Ln, Osterville, MA 02655

  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,

  Sam Amara William Raveis R.E. & Home Services

  51 Falling Leaf Ln, Osterville, MA 02655
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  /32

  $849,900

  • 2 Beds
  • 2 Baths
  • 1,533 Sq Ft

  87 Hinckley Cir, Osterville, MA 02655

  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

  George Raymond Raymond & Son REALTORS®

  87 Hinckley Cir, Osterville, MA 02655
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  /37

  $799,000

  • 3 Beds
  • 2 Baths
  • 1,856 Sq Ft

  329 Swift Ave, Osterville, MA 02655

  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,

  Lauren Scioletti Sotheby's International Realty

  329 Swift Ave, 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
• 

  

  /56

  $8,800,000

  $2M 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
• 

  

  /28

  $8,995,000

  • 6 Beds
  • 9 Baths
  • 9,464 Sq Ft

  204 Garrison Ln, Osterville, MA 02655

  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

  Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  204 Garrison Ln, Osterville, MA 02655
• 

  

  /9

  $3,125,000

  • Land
  • 2.01 Acres
  • $1,554,726 per Acre

  Lot 290 0 Indian Trail, Osterville, MA 02655

  Nestled within one of Cape Cod's most exclusive enclaves, this 2.01-acre parcel offers a rare chance to build in the coveted gated community of Oyster Harbors. Located in the village of Osterville, home to some of the region's most distinguished estates, this expansive lot offers an ideal canvas for creating your dream Cape retreat. Additional neighboring parcels offer the opportunity to expand

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  Lot 290 0 Indian Trail, 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

Showing Results 1 - 40, Page 1 of 2

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

Osterville, Barnstable, MA Home Prices vs. Nearby Neighborhoods

	Osterville	Cotuit	New Seabury-Popponesset Island	Popponesset
Median Home Price	$1,549,900	$1,250,000	$1,294,000	$1,150,000
Median Sale Price	$1,195,000 -2% YoY	$1,015,000 +19% YoY	$1,165,000 +23% YoY	$1,050,000 -25% YoY
Avg. Price per Square Foot	$772	$621	$747	$825
Median Single Family Price	$1,595,000	$1,100,000	$1,500,000	$1,250,000
Median Condo Price	$599,950	$814,000	$782,000	$420,000
Total Active Listings	53 listings	46 listings	53 listings	0 listings
Market Conditions	4 Months of Supply Seller's Market	3 Months of Supply Seller's Market	3 Months of Supply Seller's Market	0 Months of Supply Seller's Market

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. 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% of residents renting and 86% 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 $1,549,900. If you put a 20% down payment of $310,000 and had a 30-year fixed mortgage with an interest rate of 7.03%, your estimated principal and interest payment would be $8,270 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $354K a year to afford the median home price in Osterville. Learn how much home you can afford with our Home Affordability Calculator. The average household income in Osterville is $141K.

What are the best public schools in Osterville?

The best public schools that serve Osterville are:

• West Villages Elementary School has an A- Niche grade and a student teacher ratio of 13:1.
• Barnstable High School has a B Niche grade, a student teacher ratio of 11:1 and an average review score of 4.0.
• Barnstable Intermediate School has a B- Niche grade, a student teacher ratio of 10:1 and an average review score of 4.3.

What are the best private schools in Osterville?

The best private schools that serve Osterville are:

• Cape Cod Academy has an A- Niche grade, a student teacher ratio of 5:1 and an average review score of 4.0.
• Bayberry Christian School has a student teacher ratio of 10:1.
• Fair Acres Country Day School has a student teacher ratio of 8:1.

What are the most popular zip codes in Osterville, Barnstable, MA?

The most popular zip codes in Osterville, Barnstable, MA include 02655, 02648, 02601, 02632 and 02630.

What are the most popular neighborhoods near Osterville, Barnstable, MA?

The most popular neighborhoods near Osterville, Barnstable, MA are Marstons Mills, Centerville, Cotuit, Hyannis and West Barnstable.