Osterville Homes

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  /49

  $1,595,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 2,602 Sq Ft

  29 Oak Ridge Rd, Osterville, MA 02655

  Step into this classic Osterville Cape, offering a comfortable pragmatic and spacious floor plan designed for effortless everyday living. Warm, inviting rooms flow seamlessly throughout, creating a home that feels both timeless and comfortably functional.The lovely and private backyard extends the living space outdoors: ideal for quiet mornings, relaxed afternoons, and easy entertaining.Set in

  James Murphy, Jr

  Murphy Real Estate

  (508) 348-7838

  29 Oak Ridge Rd, Osterville, MA 02655
• Explore Osterville

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  /5

  $3,700 total monthly price

  • 4 Beds
  • 2.5 Baths
  • 2,350 Sq Ft
  • House for Rent

  1063 Main St, Osterville, MA 02655

  ALL YEAR RENTAL - Available 02/2026 Enjoy all that downtown Osterville have to offer, from this attractive 4 bedroom, two and bath cape home. The light and airy interior living space is further complemented by the first-floor family room. Just minutes driving to the beach. Ample storage in basement. Special detailing throughout this custom home. Tenant is responsible for utilities. Nonsmoking, no

  Mario Neno Mega Realty Services, Inc.

  1063 Main St, Osterville, MA 02655
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  /37

  $807,150 Sold Aug 15, 2025

  26 Hinckley Cir, Osterville, MA 02655

  • 3 Beds
  • 3 Baths
  • 1,934 Sq Ft
  • Built 1958

  Last Sold Summary

  • 5% Below List Price
  • $417/SF
  • 21 Days On Market

  Current Estimated Value $822,608

  Last Listing Agent virginia guimond William Raveis Real Estate & Home Services

  26 Hinckley Cir, Osterville, MA 02655
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  /42

  Est $7,430,751 Not Listed For Sale

  • 7 Beds
  • 3.5 Baths
  • 4,028 Sq Ft

  265 Sea View Ave, Osterville, MA 02655

  265 Sea View Ave, Osterville, MA 02655
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  /70

  $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

  John Cotton Sotheby's International Realty

  850 Sea View Ave, Osterville, MA 02655
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  /39

  $16,000 total monthly price

  • 4 Beds
  • 4 Baths
  • 3,684 Sq Ft
  • House for Rent

  65 Starboard Ln, Osterville, MA 02655

  Kick off 2026 in style with a winter rental escape to one of Cape Cod's most exclusive villages. This luxury Osterville retreat offers a refined coastal experience with sophisticated interiors and a prime location near pristine beaches and boutique shops. Enjoy crisp ocean air, and effortless access to acclaimed restaurants without the summer crowds. For those in the know, winter is Cape Cod's

  Daren Marvin Sotheby's International Realty

  65 Starboard Ln, Osterville, MA 02655
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  /42

  $2,150,000 Sold Apr 16, 2025

  85 Hollingsworth Rd, Osterville, MA 02655

  • 4 Beds
  • 4.5 Baths
  • 2,863 Sq Ft
  • Built 2016

  Last Sold Summary

  • 2% Below List Price
  • $751/SF
  • 32 Days On Market

  Current Estimated Value $2,296,809

  Last Listing Agent Shaelyn Hegarty Frank A Sullivan Real Estate

  85 Hollingsworth Rd, Osterville, MA 02655
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  /9

  Est $2,349,997 Not Listed For Sale

  48 Starboard Ln, Osterville, MA 02655

  48 Starboard Ln, Osterville, MA 02655
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  /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
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  /14

  $2,300 total monthly price

  • 2 Beds
  • 1 Bath
  • 406 Sq Ft
  • Condo for Rent

  3040 Falmouth Rd Unit 3, Osterville, MA 02655

  Enjoy an affordable and comfortable lifestyle in this modest 2-bedroom, second-floor condo located in the heart of Osterville. Perfect for year-round living, this unit places you close to village dining, shopping, local beaches, and convenient access to Mashpee Commons.A major benefit of this rental is that the monthly condo fee--already included in the rent--covers heat, electricity, water,

  Wander Rodriguez eXp Realty, LLC

  3040 Falmouth Rd Unit 3, Osterville, MA 02655
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  /19

  $595,000 Sold Apr 14, 2025

  170 Seth Goodspeed Way, Osterville, MA 02655

  • 2 Beds
  • 2 Baths
  • 1,320 Sq Ft
  • Built 1977

  Last Sold Summary

  • $451/SF
  • 1 Day On Market

  Current Estimated Value $622,051

  Last Listing Agent Beth Talerman Murphy Real Estate

  170 Seth Goodspeed Way, Osterville, MA 02655
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  /49

  Est $1,256,518 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,163 Sq Ft

  15 Sturbridge Dr, Osterville, MA 02655

  15 Sturbridge Dr, Osterville, MA 02655
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  /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
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  /46

  $2,500 total monthly price

  • 3 Beds
  • 2.5 Baths
  • 1,132 Sq Ft
  • House for Rent

  20 Brigantine Ave, Osterville, MA 02655

  Osterville Summer Rental! $2500/week OR minimum of three-night stay; please call for nightly and off-season rates!This Osterville home is uniquely styled with fine furnishings and touches, tastefully bringing together an aesthetic of Cape Cod with a little Art Deco. Stepping inside your home away from home, you're greeted by rich plantings and soothing color, for that feeling of ''ahhhh.'' Now

  Marina Davalos Sotheby's International Realty

  20 Brigantine Ave, Osterville, MA 02655
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  /55

  $635,000 Sold Oct 15, 2025

  22 1st Ave, Osterville, MA 02655

  • 2 Beds
  • 1 Bath
  • 884 Sq Ft
  • Built 1929

  Last Sold Summary

  • 2% Below List Price
  • $718/SF
  • 9 Days On Market

  Current Estimated Value $617,680

  Last Listing Agent Adrienne Siegel Strawberry Hill R E

  22 1st Ave, Osterville, MA 02655
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  /46

  Est $1,288,052 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,458 Sq Ft

  200 Sturbridge Dr, Osterville, MA 02655

  200 Sturbridge Dr, Osterville, MA 02655
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  /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
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  /32

  $1,150,000 Sold May 16, 2025

  10 Darby Way, Barnstable, MA 02655

  • 3 Beds
  • 2.5 Baths
  • 1,918 Sq Ft
  • Built 2016

  Last Sold Summary

  • 4% Below List Price
  • $600/SF
  • 4 Days On Market

  Last Listing Agent Jennifer McCartin Sotheby's International Realty

  10 Darby Way, Barnstable, MA 02655
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  /50

  Est $988,362 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 2,061 Sq Ft

  65 Deerfield Rd, Osterville, MA 02655

  65 Deerfield Rd, Osterville, MA 02655
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  /45

  $4,595,000

  • 4 Beds
  • 7 Baths
  • 3,557 Sq Ft

  280 Ice Valley Rd, Osterville, MA 02655

  Set on an exceptionally oversized 2.94-acre corner parcel within Osterville's highly sought-after Seapuit neighborhood, this newly built residence offers a rare combination of privacy, scale, and resort-style amenities, just minutes from the heart of Osterville Village. Surrounded by established homes in a refined residential setting, the property presents a compelling opportunity for turnkey

  Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  280 Ice Valley Rd, Osterville, MA 02655
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  /19

  $600,000 Sold May 07, 2025

  54 Jason's Ln, Barnstable, MA 02655

  • 2 Beds
  • 1 Bath
  • 936 Sq Ft
  • Built 1983

  Last Sold Summary

  • 2% Below List Price
  • $641/SF
  • 14 Days On Market

  Last Listing Agent Kim Barnocky-Grossman, CRS William Raveis Real Estate & Home Services

  54 Jason's Ln, Barnstable, MA 02655
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  /40

  Est $1,483,603 Not Listed For Sale

  • 4 Beds
  • 3 Baths
  • 3,795 Sq Ft

  60 Deerfield Rd, Osterville, MA 02655

  60 Deerfield Rd, Osterville, MA 02655
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  /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
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  /43

  $3,375,000 Sold Jul 15, 2025

  320 Parker Rd, Osterville, MA 02655

  • 5 Beds
  • 5.5 Baths
  • 5,421 Sq Ft
  • Built 2002

  Last Sold Summary

  • 11% Below List Price
  • $623/SF
  • 44 Days On Market

  Current Estimated Value $3,610,359

  Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

  320 Parker Rd, Osterville, MA 02655
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  /42

  Est $2,541,874 Not Listed For Sale

  • 5 Beds
  • 3.5 Baths
  • 3,854 Sq Ft

  298 Starboard Ln, Osterville, MA 02655

  298 Starboard Ln, Osterville, MA 02655
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  /42

  $2,650,000

  • 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
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  /17

  $495,000 Sold Jan 30, 2025

  1 Vermeer Ct, Osterville, MA 02655

  • 3 Beds
  • 2 Baths
  • 1,267 Sq Ft
  • Built 1983

  Last Sold Summary

  • 17% Below List Price
  • $391/SF
  • 56 Days On Market

  Current Estimated Value $565,330

  Last Listing Agent Heather Brigham EXIT Cape Realty

  1 Vermeer Ct, Osterville, MA 02655
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  /39

  Est $3,087,729 Not Listed For Sale

  • 4 Beds
  • 4.5 Baths
  • 4,017 Sq Ft

  175 Starboard Ln, Osterville, MA 02655

  175 Starboard Ln, Osterville, MA 02655
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  /57

  $4,550,000 Pending

  • 5 Beds
  • 7 Baths
  • 6,768 Sq Ft

  405 Bridge St, Osterville, MA 02655

  Little Island in Osterville on Cape Cod where the rhythms of the tide shape each day, there stands a home that feels like it's been waiting for you -- quietly, patiently, knowing you belong here.From the moment you step inside, the soaring two story ceilings lift your gaze toward light and space. Traditional shingle-style architecture and exquisite millwork evoke the craftsmanship of another era

  John Cotton Sotheby's International Realty

  405 Bridge St, Osterville, MA 02655
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  /42

  $5,300,000 Sold May 15, 2025

  49 N Bay Rd, Barnstable, MA 02655

  • 7 Beds
  • 7 Baths
  • 5,960 Sq Ft
  • Built 1986

  Last Sold Summary

  • 24% Below List Price
  • $889/SF
  • 208 Days On Market

  Current Estimated Value $5,577,658

  Last Listing Agent Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

  49 N Bay Rd, Barnstable, MA 02655
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  /51

  Est $1,024,709 Not Listed For Sale

  • 3 Beds
  • 2.5 Baths
  • 2,162 Sq Ft

  31 Newport Ln, Osterville, MA 02655

  31 Newport Ln, Osterville, 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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  /34

  $615,000 Sold May 01, 2025

  39 Tower Hill Rd Unit 11, Osterville, MA 02655

  • 2 Beds
  • 2.5 Baths
  • 1,632 Sq Ft
  • Built 1982

  Last Sold Summary

  • $377/SF
  • 3 Days On Market

  Current Estimated Value $650,802

  Last Listing Agent Chuck Tuttle William Raveis R.E. & Home Services

  39 Tower Hill Rd Unit 11, Osterville, MA 02655
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  /25

  Est $819,531 Not Listed For Sale

  • 2 Beds
  • 1 Bath
  • 972 Sq Ft

  329 Swift Ave, Osterville, MA 02655

  329 Swift Ave, Osterville, MA 02655
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  /20

  $579,000 Pending

  • 2 Beds
  • 2 Baths
  • 1,131 Sq Ft

  39 Tower Hill Rd Unit 1C, Osterville, MA 02655

  Nestled in the heart of charming Osterville village, this lovely unit offers the perfect blend of convenience, comfort, and community. Right in the village, you'll find delightful storefronts, cozy eateries, a welcoming library, and everyday essentials like grocery stores and parks—all easily accessible. Whether you're enjoying the local scene or seeking a quiet escape, this friendly complex

  Ed Chatelain Chatelain Real Estate

  39 Tower Hill Rd Unit 1C, Osterville, MA 02655
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  /32

  $575,000 Sold Feb 27, 2025

  19 Cesars Way, Osterville, MA 02655

  • 3 Beds
  • 2 Baths
  • 1,204 Sq Ft
  • Built 1974

  Last Sold Summary

  • 4% Below List Price
  • $478/SF
  • 50 Days On Market

  Current Estimated Value $623,379

  Last Listing Agent Michelle Ryan Today Real Estate

  19 Cesars Way, Osterville, MA 02655
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  /78

  Est $2,329,423 Not Listed For Sale

  • 4 Beds
  • 3.5 Baths
  • 4,800 Sq Ft

  8 Nutmeg Ln, Osterville, MA 02655

  8 Nutmeg Ln, Osterville, MA 02655
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  /3

  $1,599,000 Pending

  • 3 Beds
  • 2.5 Baths
  • 1,686 Sq Ft

  33 Sunset Ln, Osterville, MA 02655

  A rare find in the village of Osterville! Discover a truly exceptional opportunity in the heart of the village with this charming 3 bedroom, 2.5 bath residence. Walk or bike to everything that this delightful village has to offer. The library, post office, hardware store and fine dining are a stone's throw away. A short walk takes you to the marina and its dockside eatery and to the bay to launch

  Maureen Carven Kinlin Grover Compass

  33 Sunset Ln, Osterville, MA 02655
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  /73

  $4,200,000 Sold Aug 08, 2025

  281 Wianno Ave, Osterville, MA 02655

  • 7 Beds
  • 5.5 Baths
  • 4,375 Sq Ft
  • Built 1890

  Last Sold Summary

  • 10% Below List Price
  • $960/SF
  • 16 Days On Market

  Current Estimated Value $4,304,305

  Last Listing Agent John Hopkins Frank A Sullivan Real Estate

  281 Wianno Ave, Osterville, MA 02655
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  /40

  Est $728,276 Not Listed For Sale

  • 3 Beds
  • 2 Baths
  • 1,767 Sq Ft

  36 Renoir Dr, Osterville, MA 02655

  36 Renoir Dr, Osterville, MA 02655

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