Osterville Homes

/48
$1,195,000 Pending
- 3 Beds
- 1.5 Baths
- 1,740 Sq Ft
53 Spice Ln, Osterville, MA 02655

Enjoy classic Cape Cod living in this Archibald-designed 3-bedroom, 1.5-bath home in Osterville's desirable Oyster Hills neighborhood. Filled with natural light, the home has been thoughtfully maintained and offers a fresh, inviting feel throughout. A spacious front-to-back living room with a granite-faced fireplace provides generous gathering space while preserving a more traditional floor plan.

Livia Freitas Monteforte

Compass Massachusetts, LLC

(508) 290-7914

53 Spice Ln, Osterville, MA 02655
Explore Osterville
/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
/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 $822,273

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

26 Hinckley Cir, Osterville, MA 02655

/31
Est $2,540,220 Not Listed For Sale

97 Old Mill Rd, Osterville, MA 02655
- 5 Beds
- 5 Baths
- 3,749 Sq Ft
- Built 1890
97 Old Mill Rd, Osterville, MA 02655

Last Sold Summary
- 4% Below List Price
- $707/SF
- 121 Days On Market
Last Sold Price $2,650,000

Last Listing Agent Ellen Valentgas Sotheby's International Realty

/28
$1,095,000
- 2 Beds
- 2.5 Baths
- 1,564 Sq Ft
16 2nd Ave Unit 4, Osterville, MA 02655

Heart of Wianno! Experience the perfect blend of Cape Cod charm and modern luxury in this beautiful, built in 2023, cottage-style free-standing condo ideally located in the sought-after village of Osterville. Enjoy a lifestyle where everything is just moments away--Wianno Golf Club, sandy saltwater beaches, multiple marinas, the weekly Farmer's Market, fine dining, and boutique shopping--all

Livia Freitas Monteforte

Compass Massachusetts, LLC

(508) 978-5691

16 2nd Ave Unit 4, Osterville, MA 02655
/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
/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 $2,099,148

Last Listing Agent Shaelyn Hegarty Frank A Sullivan Real Estate

85 Hollingsworth Rd, Osterville, MA 02655

/9
Not Listed For Sale

48 Starboard Ln, Osterville, MA 02655
48 Starboard Ln, Osterville, MA 02655

Last Sold Summary
- 73 Days On Market
Last Sold Price $2,350,000

Last Listing Agent Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

/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
/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 $578,219

Last Listing Agent Beth Talerman Murphy Real Estate

170 Seth Goodspeed Way, Osterville, MA 02655

/49
Est $1,203,844 Not Listed For Sale

15 Sturbridge Dr, Osterville, MA 02655
- 3 Beds
- 2.5 Baths
- 2,163 Sq Ft
- Built 1982
15 Sturbridge Dr, Osterville, MA 02655

Last Sold Summary
- $555/SF
- 1 Day On Market
Last Sold Price $1,200,000

Last Listing Agent Rick Shechtman Kinlin Grover Compass

/48
$3,100,000 Open Sat 11AM - 1PM
- 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
/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 $589,417

Last Listing Agent Adrienne Siegel Strawberry Hill R E

22 1st Ave, Osterville, MA 02655

/46
Est $1,161,679 Not Listed For Sale

200 Sturbridge Dr, Osterville, MA 02655
- 3 Beds
- 2.5 Baths
- 2,458 Sq Ft
- Built 1983
200 Sturbridge Dr, Osterville, MA 02655

Last Sold Summary
- 3% Below List Price
- $488/SF
- 5 Days On Market
Last Sold Price $1,200,000

Last Listing Agent Amanda Kundel Kinlin Grover Compass

/23
$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 shops and restaurants in Osterville village, this home is the perfect Cape Cod

Gene Orloff Sotheby's International Realty

51 Wianno Cir, Osterville, MA 02655
/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

/50
Est $889,305 Not Listed For Sale

65 Deerfield Rd, Osterville, MA 02655
- 3 Beds
- 2 Baths
- 2,061 Sq Ft
- Built 1979
65 Deerfield Rd, Osterville, MA 02655

Last Sold Summary
- $432/SF
- 36 Days On Market
Last Sold Price $890,000

Last Listing Agent Chuck Tuttle William Raveis Real Estate & Home Services

/30
$3,499,999
- 10 Beds
- 7.5 Baths
- 6,905 Sq Ft
414 Eel, Barnstable, 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, Barnstable, MA 02655
/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

/40
Est $1,369,993 Not Listed For Sale

60 Deerfield Rd, Osterville, MA 02655
- 4 Beds
- 3 Baths
- 3,795 Sq Ft
- Built 1981
60 Deerfield Rd, Osterville, MA 02655

Last Sold Summary
- $362/SF
- 64 Days On Market
Last Sold Price $1,375,000

Last Listing Agent Colleen Riley Sotheby's International Realty

/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
/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 $3,374,332

Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

320 Parker Rd, Osterville, MA 02655

/42
Est $2,294,087 Not Listed For Sale

298 Starboard Ln, Osterville, MA 02655
- 5 Beds
- 3.5 Baths
- 3,854 Sq Ft
- Built 2002
298 Starboard Ln, Osterville, MA 02655

Last Sold Summary
- 8% Below List Price
- $649/SF
- 69 Days On Market
Last Sold Price $2,500,000

Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

/40
$2,999,000 Open Sat 11AM - 1PM
- 3 Beds
- 3 Baths
- 3,055 Sq Ft
18 Winfield Way, Osterville, MA 02655

Nestled near downtown Osterville with picturesque views and access to West Bay, this inviting home offers the perfect blend of location, charm, and opportunity. Tucked away on a private lane, this 3-bedroom, 3 full bath property presents a rare chance to own in one of Osterville's most sought-after areas. Set on a generous 0.87-acre lot, the home feels like your own private Cape Cod retreat. This

Nicole Callahan Silverstone Capeside Realty Group

18 Winfield Way, Osterville, MA 02655
/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 $5,164,764

Last Listing Agent Robert Kinlin Berkshire Hathaway HomeServices Robert Paul Properties

49 N Bay Rd, Barnstable, MA 02655

/39
Est $2,945,480 Not Listed For Sale

175 Starboard Ln, Osterville, MA 02655
- 4 Beds
- 4.5 Baths
- 4,017 Sq Ft
- Built 1981
175 Starboard Ln, Osterville, MA 02655

Last Sold Summary
- 2% Above List Price
- $722/SF
- 1 Day On Market
Last Sold Price $2,900,000

Last Listing Agent Paul Grover Berkshire Hathaway HomeServices Robert Paul Properties

/21
$3,100,000 Pending
- 4 Beds
- 4.5 Baths
- 2,752 Sq Ft
125 Wianno Cir, Osterville, MA 02655

Just a mile from Dowses Beach and Osterville village center, this Cape-style home is all about effortless summer living--where days move easily from beach to backyard to evening gatherings with friends and family.A welcoming front porch leads into bright, open living spaces designed for comfort and connection. Directly off the main living and dining areas is a patio-bordered pool, creating a

Ellen Valentgas Sotheby's International Realty

125 Wianno Cir, Osterville, MA 02655
/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 $616,310

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

39 Tower Hill Rd Unit 11, Osterville, MA 02655

/51
Est $950,552 Not Listed For Sale

31 Newport Ln, Osterville, MA 02655
- 3 Beds
- 2.5 Baths
- 2,162 Sq Ft
- Built 1975
31 Newport Ln, Osterville, MA 02655

Last Sold Summary
- $439/SF
- 3 Days On Market
Last Sold Price $950,000

Last Listing Agent Chuck Tuttle William Raveis Real Estate & Home Services

/44
$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
/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 $4,236,781

Last Listing Agent John Hopkins Frank A Sullivan Real Estate

281 Wianno Ave, Osterville, MA 02655

/25
Est $826,005 Not Listed For Sale

329 Swift Ave, Osterville, MA 02655
- 2 Beds
- 1 Bath
- 972 Sq Ft
- Built 1953
329 Swift Ave, Osterville, MA 02655

Last Sold Summary
- 34% Above List Price
- $635/SF
- 66 Days On Market
Last Sold Price $617,000

Last Listing Agent Sam Wilson Sotheby's International Realty

/53
$1,950,000 Pending
- 4 Beds
- 4 Baths
- 2,999 Sq Ft
67 Fire Station Rd, Osterville, MA 02655

This move-in ready home is located 1/4 mile from Osterville Village; 1/2 mile from Crosby Marina and less than 1 mile from Dowses Beach. Boating, swimming, golfing during the day and a quick stroll to the village at night. The home was built in 2020 with elegance and comfortable living in mind, with entertaining as a priority! The kitchen, dining and family room has an open concept design with a

Julie White William Raveis Real Estate & Home Services

67 Fire Station Rd, Osterville, MA 02655
/52
$1,080,000 Sold Mar 02, 2026

81 Falling Leaf Ln, Osterville, MA 02655
- 3 Beds
- 2.5 Baths
- 2,776 Sq Ft
- Built 1999
Last Sold Summary
- 22% Below List Price
- $389/SF
- 145 Days On Market
Current Estimated Value $1,191,762

Last Listing Agent Linda Whitcomb William Raveis Real Estate & Home Services

81 Falling Leaf Ln, Osterville, MA 02655

/78
Est $2,185,061 Not Listed For Sale

8 Nutmeg Ln, Osterville, MA 02655
- 4 Beds
- 3.5 Baths
- 4,800 Sq Ft
- Built 2024
8 Nutmeg Ln, Osterville, MA 02655

Last Sold Summary
- 40% Below List Price
- $760/SF
- 41 Days On Market
Last Sold Price $3,650,000

Last Listing Agent Sean Dacey Coldwell Banker Realty

/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
/84
$1,100,000 Sold Nov 20, 2025

24 Indigo Ln, Osterville, MA 02655
- 4 Beds
- 3.5 Baths
- 3,135 Sq Ft
- Built 1992
Last Sold Summary
- 19% Below List Price
- $351/SF
- 91 Days On Market
Current Estimated Value $1,210,185

Last Listing Agent Tim/Becca Team Great Oak Realty Executives

24 Indigo Ln, Osterville, MA 02655

/40
Est $638,710 Not Listed For Sale

36 Renoir Dr, Osterville, MA 02655
- 3 Beds
- 2 Baths
- 1,767 Sq Ft
- Built 1983
36 Renoir Dr, Osterville, MA 02655

Last Sold Summary
- 6% Above List Price
- $342/SF
- 2 Days On Market
Last Sold Price $605,000

Last Listing Agent Chuck Tuttle William Raveis Real Estate & Home Services

/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
/34
$560,000 Sold Jun 27, 2025

7 Fox Hollow Ln, Osterville, MA 02655
- 2 Beds
- 2 Baths
- 1,560 Sq Ft
- Built 1986
Last Sold Summary
- 3% Below List Price
- $359/SF
- 16 Days On Market
Current Estimated Value $571,993

Last Listing Agent Cindy Harrington Berkshire Hathaway HomeServices Robert Paul Properties

7 Fox Hollow Ln, Osterville, MA 02655

Showing Results 1 - 40, Page 1 of 18

Massachusetts Barnstable County Barnstable Osterville

Learn more about living in Osterville

Home Trends in Osterville, MA

On average, homes in Osterville, Barnstable sell after 65 days on the market compared to the national average of 55 days. The median sale price for homes in Osterville, Barnstable over the last 12 months is $1,350,000, up 13% from the median home sale price over the previous 12 months.

Housing Trends

Median Sale Price

$1,350,000

Median Single Family Sale Price

$1,500,000

Median 2 Bedroom Sale Price

$545,000

Median 1 Bedroom Sale Price

$580,000

Average Price Per Sq Ft

$789

Number of Homes for Sale

Last 12 months Home Sales

116

Months of Supply

2.60

Median List Price

$1,495,000

Median Change From 1st List Price

Median Home Sale Price YoY Change

13%

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Osterville Homes

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