Osterville
Neighborhood in Barnstable, Massachusetts
Barnstable County 02655
Shingle-style homes in Osterville
Osterville housing includes everything from modest mid-1900s ranch-style homes to multi-million-dollar waterfront residences in the Oyster Harbors golf community. “Some people think of Chatham as the nicest place on the cape, but Chatham doesn’t have a community like Oyster Harbors or a beach like Sea View,” Regan says. Traditional Cape Cods and ranch-style homes with three to four bedrooms line the streets closest to state Route 28 and some of the side streets near the center of the village. A few start as low as $550,000, and others run upwards of $800,000. Shingle-style and Dutch Colonial-style homes with gambrel roofs start around $1 million, and in the Wianno area, they often list between $3 million and $5 million. On Little Island, along Sea View Avenue and within Oyster Harbors, homes are built to maximize views of the bays or the sound and to withstand the forces of nature. There are a few remaining homes from the late 1800s, but many of those closest to the wind and waves were rebuilt after 2000. Depending on size, acreage and distance from the water, prices range anywhere from $2 million to $12 million, though one estate on Wianno Head recently sold for nearly $23 million.Enjoying the Nantucket Sound and miles of bay access
Some of the main draws for Osterville are its access to recreation and its natural beauty. With 5 miles of shoreline along the Nantucket Sound and 17 miles of bayfront coast, most people spend a good portion of their time enjoying the water. Sailors come to the Crosby Yacht Yard to purchase custom catboats, which they can sail in West Bay and beyond. Kayakers, fishermen and swimmers all flock to the shores as well. Dowses Beach, open only to Barnstable residents, is a sandy beach that borders the sound and East Bay. There are wooded walking paths and a children’s garden at the 8.5-acre Armstrong-Kelley Park, as well as a shaded picnic area. On rainy days, families can visit the Osterville Village Library to listen to story time or participate in arts and crafts workshops. Members of the Wianno Golf Club and Oyster Harbors Club can use their 18-hole courses and tennis courts, and the village also has tennis and pickleball courts that are available for all locals to use.Barnstable Public Schools and the A-plus-rated Cape Cod Academy
Year-round residents can send their children to schools within Barnstable Public Schools, a district that earns a B-plus on Niche. Osterville children begin their education at West Villages Elementary School, a B-plus-rated school serving kindergarten through third-grade learners. For fourth and fifth grades, all Barnstable County students may attend Barnstable United Elementary School, which gets a B-minus score. Barnstable Intermediate School, with a B-minus rating, covers sixth through seventh, and B-plus-rated Barnstable High School teaches eighth through 12th grades. At Barnstable High, students can gain real-world experience in fields including hospitality, environmental science and medicine. There are also highly rated private schools nearby, including Cape Cod Academy in Osterville and Falmouth Academy in Falmouth. Both receive A-plus ratings.Osterville Village Day and other summer events
Since the mid-1800s, Osterville has been a popular summer retreat. Today, the Osterville Village Association and the Osterville Village Library both plan a long list of events throughout the year, though the highest concentration of festivities takes place in the summer. The library’s annual Summer Soiree is a series of lectures, outdoor concerts and kid-friendly activities, including visits from Frisbee-catching dogs and an inflatable whale. Osterville Village Day takes place each June, and participants come in themed attire to enjoy a day of festivities kicked off by a road race. Although the majority of homeowners are part-time residents, “They’re always trying to plan things for year-round residents and bring the people who are second homeowners back down to enjoy seasonal events,” Regan says. There’s a chocolate festival in February, and the Christmas Open House and Stroll takes place in the middle of December.Travel around Osterville and beyond
Though many people take advantage of private docks, moorings and marinas to access the cape’s scenic spots by water, there are several land-based travel options as well. State Route 28 crosses through the northern portion of Osterville, providing a direct — though sometimes congested — thoroughfare around the cape. There is a Cape Cod Regional Transit Authority bus stop at the corner of Tower Hill Road & Main Street. The buses take riders east to the Cape Cod Mall in Hyannis and west to Woods Hole. In Hyannis, about 6 miles away, those who need to get to Boston can fly out of the Cape Cod Gateway Airport or catch the CapeFLYER trains, which run on weekends during summer months.Boutiques on Main Street and fresh produce from the Osterville Farmers Market
Osterville’s walkable downtown area is home to high-end boutiques with everything from vintage silver barware and summery household décor to clothing and shoes for an evening at the Wianno Golf Club. A handful of art galleries showcase the work of local painters and artisans as well. Fancy's Market, where community members have come to shop since 1839, has a well-stocked maze of aisles loaded with fresh microgreens, local honey and peach pie. Around noon, the store is bursting with people who come for Boar’s Head sandwiches and subs. Wimpy's Seafood Cafe & Market, another long-time fixture, carries seafood and prepared foods, such as lobster rolls and fried clams. Crisp specializes in flatbread pizza, and North Sister Café offers vegetarian and gluten-free options for breakfast and lunch. Boaters head to the Chart Room at Crosby's to enjoy sunset views while dining on clam chowder and swordfish. Osterville also has a weekly farmers market on Fridays from late spring through early fall — shoppers can find Cape Cod-grown heirloom vegetables, baked goods and farm-fresh eggs.Preserving Osterville for future generations
Though many generations have enjoyed spending their summers in Osterville, years of human activity have impacted the waterways and other natural resources. The town of Barnstable, along with the entire cape, is working to transition to sewer systems in an effort to lower nitrogen levels in the water and soil. As the project will roll out over several years, homeowners with aging septic systems may be required to update them to more modern ones in the meantime. Another concern for Osterville residents is the proposed Avangrid wind farm, which would place turbines in the Nantucket Sound and electrical cables under Dowses Beach. Several groups are lobbying against the project due to concerns over its possible effects to the cape’s environment.

Agents Specializing in this Area
-
JM
James Murphy, Jr
Murphy Real Estate
(774) 352-5756
54 Total Sales
7 in Osterville
$200K - $3.7M Price Range
-
Michael Degnan
Realty Executives of Cape Cod
(774) 208-9162
73 Total Sales
1 in Osterville
$806,000 Price
-
Marie Souza
Cape Cod Real Estate Services
(508) 418-4062
64 Total Sales
4 in Osterville
$530K - $1.9M Price Range
-
Mike Karras
Responds QuicklyWilliam Raveis Real Estate & Homes Services
(774) 208-0939
107 Total Sales
1 in Osterville
$680,000 Price
-
John Cotton
Sotheby's International Realty
(774) 252-9948
90 Total Sales
31 in Osterville
$360K - $10.9M Price Range
-
Kenneth Olson
eXp Realty
(401) 406-4227
36 Total Sales
2 in Osterville
$655K - $875K Price Range
Schools
Interested in learning more about homes in this area? Reach out to
, an experienced agent in this neighborhood.Parks in this Area
Transit
Crime and Safety
1 - Low Crime, 10 - High Crime | Osterville | US |
---|---|---|
Homicide | 1 | 4 |
Sexual Assault | 1 | 4 |
Assault with Weapon | 1 | 4 |
Robbery | 1 | 4 |
Burglary | 1 | 4 |
Motor Vehicle Theft | 1 | 4 |
Larceny | 1 | 4 |
Crime Score | 1 | 4 |
Source: WhatIsMyCrimeRisk.com
Osterville Demographics and Home Trends
On average, homes in Osterville, Barnstable sell after 58 days on the market compared to the national average of 49 days. The median sale price for homes in Osterville, Barnstable over the last 12 months is $1,262,500, up 33% from the median home sale price over the previous 12 months.
Housing Trends
Neighborhood Facts
Open Houses
-
Sunday, Jun 151 - 3pm
Distribution of Home Values
Homes for Sale
Homes for Rent
Interested in learning more about homes in this area? Reach out to
, an experienced agent in this neighborhood.Average Home Value
Property Mix - Square Feet
This Neighborhood Has More Owners
Demographics
Finances
Education and Workforce
Weather
Area Factors
Somewhat Bikeable
Bike Score®
Car-Dependent
Walk Score®
Minimal Transit
Transit Score®
Sound Score® measures the noise level of any address. Transit Score® measures access to public transit. Bike Score® measures the bikeability of any address.
Nearby Neighborhoods

Tight-knit Cape Cod village with an amateur baseball league

Cape Cod neighborhood with access to boating, hiking and golf

Tight-knit private beach community on Cape Cod

Mid-cape village along a national scenic byway