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Osterville Homes for Sale

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  • 31 Jasons Ln, Osterville, MA 02655
    31 Jasons Ln, Osterville, MA 02655
    31 Jasons Ln, Osterville, MA 02655
    /14

    $675,000

    • 3 Beds
    • 3 Baths
    • 1,348 Sq Ft

    31 Jasons Ln, Osterville, MA 02655

    Must see opportunity to roll up your sleeves and make this Diamond in the rough a sparkling Gem! Three Bedrooms and Three full Baths all on one first floor level! Two fireplaces!Natural gas hot water baseboard heat. Lower level with finished entertainment room and walk out. This room also has a Natural gas stove. Come and see what you can do to make this house your new home!

    Paul Bryant Nauset Real Estate

    31 Jasons Ln, Osterville, MA 02655
  • 105 Parker Rd Unit B, Osterville, MA 02655
    105 Parker Rd Unit B, Osterville, MA 02655
    105 Parker Rd Unit B, Osterville, MA 02655
    /36

    $995,000

    Open Fri 10:30AM - 12PM
    • 2 Beds
    • 2.5 Baths
    • 1,954 Sq Ft

    105 Parker Rd Unit B, Osterville, MA 02655

    Offered for the first time in twenty-five years, this spacious two bedroom, two and one half bath condo at Fairways in Osterville village is perfect for summer or year-round living. The condo abuts the Wianno Golf course and offers three floors of living including basement storage and a detached one car garage.. The second floor includes a light-filled living room lined with windows,a gas

    Gene Orloff Sotheby's International Realty

    105 Parker Rd Unit B, Osterville, MA 02655
  • 114 King Arthur Dr, Barnstable, MA 02601
    114 King Arthur Dr, Barnstable, MA 02601
    114 King Arthur Dr, Barnstable, MA 02601
    /28

    $784,000

    • 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
  • 114 King Arthur Dr, Osterville, MA 02655
    114 King Arthur Dr, Osterville, MA 02655
    114 King Arthur Dr, Osterville, MA 02655
    /33

    $784,000

    Open Sat 12PM - 1:30PM
    • 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
  • 727 Main St Unit B1, Osterville, MA 02655
    727 Main St Unit B1, Osterville, MA 02655
    727 Main St Unit B1, Osterville, MA 02655
    /37

    $599,900

    Open Sat 11AM - 1PM
    • 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
  • 7 Bonnie Briar Rd, Osterville, MA 02655
    7 Bonnie Briar Rd, Osterville, MA 02655
    7 Bonnie Briar Rd, Osterville, MA 02655
    /26

    $685,000

    • 3 Beds
    • 2 Baths
    • 1,144 Sq Ft

    7 Bonnie Briar Rd, Osterville, MA 02655

    Welcome to 7 Bonnie Briar Lane in beautiful Osterville -- a charming opportunity tucked within one of Cape Cod's most sought-after neighborhoods. This inviting 3-bedroom home offers 1,144 square feet of comfortable living space, blending easy coastal living with everyday functionality. Ideally located just moments from pristine beaches, the village center, and local marinas, this property is

    Joan Witter Compass Massachusetts, LLC

    7 Bonnie Briar Rd, Osterville, MA 02655
  • 420 Starboard Ln, Osterville, MA 02655
    420 Starboard Ln, Osterville, MA 02655
    420 Starboard Ln, Osterville, MA 02655
    /49

    $1,995,000

    Open Sun 11AM - 1PM
    • 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

    John Cotton Sotheby's International Realty

    420 Starboard Ln, Osterville, MA 02655
  • 48 Starboard Ln, Osterville, MA 02655
    48 Starboard Ln, Osterville, MA 02655
    48 Starboard Ln, Osterville, MA 02655
    /61

    $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-inspired swimming pool and cabana, a renovated boathouse with a float for non-motorized crafts, and a deeded beach lot on Long Beach. Upon approaching the estate, an

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    48 Starboard Ln, Osterville, MA 02655
  • 140 Seapuit Rd, Osterville, MA 02655
    140 Seapuit Rd, Osterville, MA 02655
    140 Seapuit Rd, Osterville, MA 02655
    /89

    $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
  • 109 Eel River Rd, Osterville, MA 02655
    109 Eel River Rd, Osterville, MA 02655
    109 Eel River Rd, Osterville, MA 02655
    /48

    $10,500,000

    • 7 Beds
    • 5.5 Baths
    • 6,368 Sq Ft

    109 Eel River Rd, Osterville, MA 02655

    Presenting a rare and extraordinary opportunity set along the shores of Osterville's exclusive West Bay. This exquisite waterfront estate features a four-bedroom main residence masterfully designed by Hutker Architects to showcase sweeping water views amidst inimitable quality and craftsmanship. Designed as a generational compound affording the utmost privacy in an incomparable setting, the

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    109 Eel River Rd, Osterville, MA 02655
  • 156 E Bay Rd, Osterville, MA 02655
    156 E Bay Rd, Osterville, MA 02655
    156 E Bay Rd, Osterville, MA 02655
    /60

    $3,450,000

    • 4 Beds
    • 5 Baths
    • 2,574 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
  • 103 Falling Leaf Ln, Osterville, MA 02655
    103 Falling Leaf Ln, Osterville, MA 02655
    103 Falling Leaf Ln, Osterville, MA 02655
    /29

    $1,050,000

    • 3 Beds
    • 3 Baths
    • 1,980 Sq Ft

    103 Falling Leaf Ln, Osterville, MA 02655

    Light, bright and located in a quiet neighborhood close to beaches and all that Osterville has to offer is this sparkling ranch. You will love the cathedral ceilings, hardwood floors and open floor plan. The primary is spacious with a great private bath. The lower level is completely finished with three rooms and a full bath. Perfect for overflow, an exercise room and a family room. This house is

    Witter & Witter Boston/Cape Cod Compass

    103 Falling Leaf Ln, Osterville, MA 02655
  • 179 Pineleigh Path, Barnstable, MA 02655
    179 Pineleigh Path, Barnstable, MA 02655
    179 Pineleigh Path, Barnstable, MA 02655
    /42

    $5,950,000

    • 5 Beds
    • 8 Baths
    • 8,740 Sq Ft

    179 Pineleigh Path, Barnstable, MA 02655

    Set on the 14th fairway of 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. Thoughtfully designed living spaces feature soaring ceilings and a

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    179 Pineleigh Path, Barnstable, MA 02655
  • 8 Brigantine Ave, Osterville, MA 02655
    8 Brigantine Ave, Osterville, MA 02655
    8 Brigantine Ave, Osterville, MA 02655
    /43

    $589,000

    • 2 Beds
    • 1.5 Baths
    • 1,060 Sq Ft

    8 Brigantine Ave, Osterville, MA 02655

    Well-maintained 2 bedroom, 1.5 bath ranch with a 1-car garage set on approximately .62 acres. Comfortable one-floor living with a practical layout, spacious yard, and plenty of room to enjoy the outdoors. Whether you're starting out, downsizing, or just looking for an easy-to-maintain home with some land, this property is worth a look. Convenient location with solid upkeep inside and out.

    Timothy Scozzari Today Real Estate

    8 Brigantine Ave, Osterville, MA 02655
  • 727 Main St Unit 3, Osterville, MA 02655
    727 Main St Unit 3, Osterville, MA 02655
    727 Main St Unit 3, Osterville, MA 02655
    /22

    $689,000

    Open Sat 11AM - 12:30PM
    • 2 Beds
    • 2 Baths
    • 1,198 Sq Ft

    727 Main St Unit 3, 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 stainless steel appliances, stone countertops, island and built-in banquette, with French doors opening to a charming

    Debra Caney Sotheby's International Realty

    727 Main St Unit 3, Osterville, MA 02655
  • 727 Main St Unit F3, Osterville, MA 02655
    727 Main St Unit F3, Osterville, MA 02655
    727 Main St Unit F3, Osterville, 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
  • 105 Parker Rd Unit B, Osterville, MA 02655
    105 Parker Rd Unit B, Osterville, MA 02655
    105 Parker Rd Unit B, Osterville, MA 02655
    /33

    $995,000

    Open Fri 10:30AM - 12PM
    • 2 Beds
    • 2.5 Baths
    • 1,954 Sq Ft

    105 Parker Rd Unit B, Osterville, MA 02655

    Offered for the first time in twenty-five years, this spacious two bedroom, two and one half bath condo at Fairways in Osterville village is perfect for summer or year-round living. The condo abuts the Wianno Golf course and offers three floors of living including basement storage and a detached one car garage..The second floor includes a light-filled living room lined with windows,a gas

    Gene Orloff Sotheby's International Realty

    105 Parker Rd Unit B, Osterville, MA 02655
  • 46 Great Bay Rd, Osterville, MA 02655
    46 Great Bay Rd, Osterville, MA 02655
    46 Great Bay Rd, Osterville, MA 02655
    /54

    $8,500,000

    • 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, (complete with 30 Amp power outlets and fresh water). Featuring a Primary Suite and Guest Suite both on the 1st Floor, the residence

    Chuck Tuttle William Raveis Real Estate & Home Services

    46 Great Bay Rd, Osterville, MA 02655
  • 727 Main St Unit B1, Osterville, MA 02655
    727 Main St Unit B1, Osterville, MA 02655
    727 Main St Unit B1, Osterville, MA 02655
    /46

    $599,900

    Open Sat 11AM - 1PM
    • 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
  • 84 Hinckley Cir, Osterville, MA 02655
    84 Hinckley Cir, Osterville, MA 02655
    84 Hinckley Cir, Osterville, MA 02655
    /39

    $749,900

    • 3 Beds
    • 1.5 Baths
    • 1,008 Sq Ft

    84 Hinckley Cir, Osterville, MA 02655

    Charming one-level ranch offered for the first time in generations, ideally located in the heart of Osterville Village. Only 1.5 miles to beautiful Dowses Beach, a short 8 minute drive to sought-after Craigville Beach, and a quick 0.4 miles to the clear waters of Joshua Pond. This inviting "Cape Cod Escape" features 3 bedrooms and 1.5 baths, offering easy single-floor living and endless

    Chelsea McLaughlin RE/MAX Legacy

    84 Hinckley Cir, Osterville, MA 02655
  • 16 Second Unit 4, Barnstable, MA 02655
    16 Second Unit 4, Barnstable, MA 02655
    16 Second Unit 4, Barnstable, MA 02655
    /40

    $1,075,000

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

    16 Second Unit 4, Barnstable, MA 02655

    In the heart of Wianno, surrounded by Osterville’s iconic multi-million-dollar estates, this newly built 2023 free-standing golf villa offers effortless luxury and carefree Cape Cod living. Just moments to Wianno Golf Club, Dowses Beach, marinas, boutique shopping, acclaimed dining, and the Osterville Farmers Market, the location is exceptional. The light-filled interior features soaring

    Agent Photo

    Livia Freitas Monteforte

    Compass

    (508) 979-0555

    16 Second Unit 4, Barnstable, MA 02655
  • 55 Seth Goodspeed Way, Osterville, MA 02655
    55 Seth Goodspeed Way, Osterville, MA 02655
    55 Seth Goodspeed Way, Osterville, MA 02655
    /48

    $674,900

    $24K PRICE DROP
    • 2 Beds
    • 2 Baths
    • 1,040 Sq Ft

    55 Seth Goodspeed Way, Osterville, MA 02655

    Just in time for Summer! Move right into this sun-filled, open-concept ranch with one-car garage and oversized shed, located in desirable Osterville Heights! Set on a spacious, partially fenced private yard with room for potential pool, this home is perfect for outdoor entertaining, barbecues, lawn games and relaxing with family and friends. Recent improvements include enhanced landscaping, fresh

    Donna Christopher Sotheby's International Realty

    55 Seth Goodspeed Way, Osterville, MA 02655
  • 30 Cockachoiset, Osterville, MA 02655
    30 Cockachoiset, Osterville, MA 02655
    30 Cockachoiset, Osterville, MA 02655
    /49

    $3,900,000

    • 4 Beds
    • 4.5 Baths
    • 4,241 Sq Ft

    30 Cockachoiset, Osterville, MA 02655

    Defined by its water views, generous grounds, and multiple outdoor living spaces, 30 Cockachoiset (''Dillon House'') offers a welcoming coastal retreat designed for gathering, entertaining, and enjoying life by the water. The main level is thoughtfully designed with an open floor plan anchored by a well-equipped kitchen that flows seamlessly into a sun-filled breakfast nook and sitting area,

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    30 Cockachoiset, Osterville, MA 02655
  • 30 Cockachoiset Ln, Barnstable, MA 02655
    30 Cockachoiset Ln, Barnstable, MA 02655
    30 Cockachoiset Ln, Barnstable, MA 02655
    /42

    $3,900,000

    • 4 Beds
    • 4.5 Baths
    • 4,241 Sq Ft

    30 Cockachoiset Ln, Barnstable, MA 02655

    Defined by sweeping water views, expansive grounds, and exceptional outdoor living spaces, 30 Cockachoiset (“Dillon House”) offers a welcoming coastal retreat designed for gathering and entertaining. The open-concept main level features a well-equipped kitchen flowing into a sun-filled breakfast nook and sitting area surrounded by walls of windows overlooking the water. Additional highlights

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    30 Cockachoiset Ln, Barnstable, MA 02655
  • 12 Cockachoiset, Osterville, MA 02655
    12 Cockachoiset, Osterville, MA 02655
    12 Cockachoiset, 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
  • 12 Cockachoiset Ln, Barnstable, MA 02655
    12 Cockachoiset Ln, Barnstable, MA 02655
    12 Cockachoiset Ln, Barnstable, 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 sought-after seaside villages along Nantucket Sound, 12 Cockachoiset - known as the iconic “Windmill House” - blends coastal charm with distinctive architectural character. Recognized for its two-story windmill adorned with seaside murals, the home features water views from a private balcony and inviting indoor-outdoor living spaces

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    12 Cockachoiset Ln, Barnstable, MA 02655
  • 81 Osterville West Barnstable Rd, Osterville, MA 02655
    81 Osterville West Barnstable Rd, Osterville, MA 02655
    81 Osterville West Barnstable Rd, Osterville, MA 02655
    /41

    $1,950,000

    • 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 just minutes from everything Osterville Village has to offer. Set on a sprawling, wooded lot, the home's classic exterior is highlighted by a stately pillared portico and a winding stone walkway that create distinguished curb appeal.The interior opens into a center hall layout where architectural columns frame a grand living room defined

    Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

    81 Osterville West Barnstable Rd, Osterville, MA 02655
  • 153 Hickory Hill Cir, Osterville, MA 02655
    153 Hickory Hill Cir, Osterville, MA 02655
    153 Hickory Hill Cir, Osterville, MA 02655
    /36

    $899,000

    • 4 Beds
    • 2.5 Baths
    • 2,585 Sq Ft

    153 Hickory Hill Cir, Osterville, MA 02655

    This 4 bedroom home, nestled in one of Osterville's most coveted neighborhoods, is perfect for both relaxation and entertaining, offering a blend of comfort and space for creating unforgettable memories. The fantastic layout connects the sun-filled living room, kitchen, and dining area, with a slider leading to a deck featuring an awning for shade. There's also a spacious family room with gas

    Amanda Kundel Kinlin Grover Compass

    153 Hickory Hill Cir, Osterville, MA 02655
  • 162 Main St, Osterville, MA 02655
    162 Main St, Osterville, MA 02655
    162 Main St, Osterville, MA 02655
    /54

    $1,785,000

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

    162 Main St, Osterville, MA 02655

    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 effortless living both indoors and out. Imagine

    Kimberly Gazal Santos Property Cape Cod

    162 Main St, Osterville, MA 02655
  • 955 Main St, Osterville, MA 02655
    955 Main St, Osterville, MA 02655
    955 Main St, Osterville, MA 02655
    /52

    $1,579,000

    • 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
  • 93 Oyster Way, Barnstable, MA 02655
    93 Oyster Way, Barnstable, MA 02655
    93 Oyster Way, Barnstable, MA 02655
    /24

    $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
  • 441 Old Mill Rd, Osterville, MA 02655
    441 Old Mill Rd, Osterville, MA 02655
    441 Old Mill Rd, Osterville, MA 02655
    /17

    $810,000

    • 2 Beds
    • 2 Baths
    • 1,144 Sq Ft

    441 Old Mill Rd, Osterville, MA 02655

    Osterville opportunity! Situated on 1.4 acres and abutting conservation land, this 2-bedroom, 2-bath raised ranch offers endless possibilities. Located just moments from Osterville's charming village center, you'll enjoy easy access to boutique shopping, delightful dining, and local favorite, Dowses Beach. Whether it's a thoughtful home renovation or a complete reimagining to unlock the full

    Diane Boudreau Kinlin Grover Compass

    441 Old Mill Rd, Osterville, MA 02655
  • 20 Deerfield Rd, Osterville, MA 02655
    20 Deerfield Rd, Osterville, MA 02655
    20 Deerfield Rd, Osterville, MA 02655
    /5

    $874,400

    Open Fri 11AM - 1PM
    • 3 Beds
    • 2 Baths
    • 2,076 Sq Ft

    20 Deerfield Rd, Osterville, MA 02655

    Property is being offered via Real Estate Auction on Friday, June 26th at 11am on-site. The actual selling price will be determined auction day. List price/estimated value seen is set at the real estate tax assessment. Pre-auction offers must be presented on the auction P&S and are subject to seller confirmation. 10% Buyer's Premium applies. Re: The Estate of Beth E. Higgins. 2,076+/- sf 3BR, 2BA

    Justin Manning JJManning Auctioneers

    20 Deerfield Rd, Osterville, MA 02655
  • 255 Bayberry Way, Osterville, MA 02655
    255 Bayberry Way, Osterville, MA 02655
    255 Bayberry Way, Osterville, MA 02655
    /44

    $7,900,000

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

    255 Bayberry Way, Osterville, MA 02655

    Welcome to ''Point House,'' an extraordinary 5.98-acre waterfront estate set on a private peninsula overlooking the shimmering waters of West Bay. Surrounded by breathtaking natural beauty, this rare offering pairs sweeping water views with exceptional privacy, highlighted by expansive lawns, curated gardens, a private sandy beach, and a substantial deep-water dock with direct access to Nantucket

    Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

    255 Bayberry Way, Osterville, MA 02655
  • 177 Bayview Cir, Osterville, MA 02655
    177 Bayview Cir, Osterville, MA 02655
    177 Bayview Cir, Osterville, MA 02655
    /38

    $869,900

    $80K PRICE DROP
    • 3 Beds
    • 2.5 Baths
    • 2,050 Sq Ft

    177 Bayview Cir, Osterville, MA 02655

    Summer is in the Air! Welcome 177 Bayview Circle and Osterville Village. Enjoy sunbathing and swimming at Dowses beach, go clamming off Bridge Street, stroll to Fancy's Market and Main St for dining, shopping, ice cream and more. This lovely property is also near town way to water, Osterville Library and Post Office, Crosby Yacht, East Bay, the farmers market and private golf clubs. Come see this

    Kathleen Craig Berkshire Hathaway HomeServices Robert Paul Properties

    177 Bayview Cir, Osterville, MA 02655
  • 5 Briar Patch Rd, Osterville, MA 02655
    5 Briar Patch Rd, Osterville, MA 02655
    5 Briar Patch 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
  • 34 Farm Valley Rd, Osterville, MA 02655
    34 Farm Valley Rd, Osterville, MA 02655
    34 Farm Valley Rd, Osterville, MA 02655
    /52

    $2,950,000

    Open Sun 11AM - 12:30PM $150K PRICE DROP
    • 3 Beds
    • 3.5 Baths
    • 5,008 Sq Ft

    34 Farm Valley Rd, Osterville, MA 02655

    From the moment you arrive, you're greeted by a stone circular driveway and a large front porch that warmly says, ''Welcome--please come in!''Once inside, you immediately notice the home's timeless elegance combined with the comfort needed for everyday living. Each room is perfectly sized, and the thoughtful layout and seamless flow from one room to the next make this home ideal for family

    Julie White William Raveis Real Estate & Home Services

    34 Farm Valley Rd, Osterville, MA 02655
  • 207 Crystal Lake Rd, Osterville, MA 02655
    207 Crystal Lake Rd, Osterville, MA 02655
    207 Crystal Lake Rd, Osterville, MA 02655
    /16

    $8,750,000

    New Construction
    • 8 Beds
    • 5.5 Baths
    • 6,500 Sq Ft

    207 Crystal Lake Rd, Osterville, MA 02655

    A generational waterfront setting on Crystal Lake with approved Patrick Ahearn plans and a privately owned dock - an exceptionally rare, build-ready opportunity within a stone's throw of Osterville beaches and village center.A truly distinctive offering on the shores of Crystal Lake in one of Osterville's most coveted and tightly held neighborhoods. With direct lake frontage, a privately owned

    Shaelyn Hegarty Frank A Sullivan Real Estate

    207 Crystal Lake Rd, Osterville, MA 02655
  • 351 Swift Ave, Osterville, MA 02655
    351 Swift Ave, Osterville, MA 02655
    351 Swift Ave, Osterville, MA 02655
    /24

    $695,000

    $80K PRICE DROP
    • 3 Beds
    • 1 Bath
    • 1,009 Sq Ft

    351 Swift Ave, Osterville, MA 02655

    Builder/Investor Opportunity in Osterville with Expansion Potential!Charming 3-bedroom, 1-bath home on a spacious 0.64-acre lot in one of Osterville's most desirable locations. Features include a sunroom, garage, additional shed, private backyard, and newer boiler, gas furnace and heat pump.Conveniently located near Dowses and Craigville Beaches and close to Osterville Main Street shops and

    Kami Dimitrova EXIT Cape Realty

    351 Swift Ave, Osterville, MA 02655
  • 146 Scudder Rd, Osterville, MA 02655
    146 Scudder Rd, Osterville, MA 02655
    146 Scudder Rd, Osterville, MA 02655
    /46

    $2,595,000

    New Construction $55K PRICE DROP
    • 3 Beds
    • 4 Baths
    • 2,650 Sq Ft

    146 Scudder Rd, Osterville, MA 02655

    This beautiful new Osterville home is perfectly situated in Wianno, just minutes from village shops, restaurants, and Dowses Beach. With its open floor plan, white oak hardwood floors, and exceptional attention to detail, this charming property offers coastal living at its finest.The stunning kitchen features quartzite countertops, Viking appliances, and a large island with generous seating and

    Gene Orloff Sotheby's International Realty

    146 Scudder Rd, Osterville, MA 02655

Showing Results 1 - 40, Page 1 of 2

Massachusetts Barnstable County Barnstable Osterville

Real Estate & Homes for Sale in Osterville, Barnstable

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. Osterville is a neighborhood with a crime score of 1, making it safer than the average neighborhood in the U.S. 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.
Is Osterville, MA a safe neighborhood?
Osterville, MA is safer than the average neighborhood in the United States. It received a crime score of 1 out of 10.
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 6.52%, your estimated principal and interest payment would be $7,580 a month plus property taxes, HOA fees, home insurance, PMI, and utilities. Using the 28% rule, you would need to make at least $325K 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:
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, 02601, 02635 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, Hyannis and West Barnstable.
Are home prices dropping in Osterville?
Yes, home prices in Osterville are down 16% in the last 12 months.

Osterville Home Prices vs. Nearby Barnstable, MA Neighborhoods

Osterville Dennis Village West Chatham Cataumet
Median Home Price
$1,495,000
$1,250,000
$1,700,000
$1,772,500
Median Sale Price
$1,305,000
+2% YoY
$1,196,250
+23% YoY
$1,455,000
+26% YoY
$1,447,750
+81% YoY
Median Single Family Price
$1,560,000
$1,200,000
$1,975,000
$667,000
Median Condo Price
$599,900
$374,950
$1,062,500
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Total Active Listings
73
15
17
4
Market Conditions
4 Months
Balanced Market
2 Months
Seller's Market
1 Months
Seller's Market
4 Months
Seller's Market
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