$1,619,283Average Value$780Average Price per Sq Ft30Homes For Sale
From Oysterville to Osterville, a popular summer destination
Osterville, one of the town of Barnstable’s seven villages, began as a shipbuilding and oystering community. By the late 1800s, word of Osterville got to Boston, and it began to transform into a luxury summer home destination. “Today, Osterville has become a comfortable place for top magnates of industries to spend their summers,” says Jamie Regan, senior vice president of Compass Osterville, who has lived on the cape for more than 40 years. “It has one of the finest private golf course communities, Oyster Harbors, that’s on the banks of the Cotuit Bay — their sunset views are just amazing.” Miles of coastline bordering bays and the Nantucket Sound allow plenty of opportunities for sailing locally made Crosby catboats or lounging in the white sand at Dowses Beach. Those who prefer golf and tennis have two private courses to choose from, and there are always events taking place in the center of the village. With designated scenic roads running through the area, many people begin their days with a stroll down the village’s tree-lined sidewalks, passing yards filled with blue hydrangeas.
Visit Osterville a tight-knit community in Cape Cod.
Relax with your feet in the sand at Dowses Beach in Osterville.
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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.
Osterville residents take in the Cape Cod scenic spots by water.
Sailboats gently blow sway in the wind of a bay in Osterville.
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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.
Pick up some fresh threads at Reel Island Co of Osterville.
Shop for fresh vegetables at the Osterville Farmers Market.
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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.
Kids can build and paint owl houses at the Osterville Public Library.
Osterville artist show off their work at the Osterville Village Day.
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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.
Gray shingle homes are very popular in Osterville.
Dutch Colonial-style homes with gambrel roofs start around $1 million dollars in Osterville.
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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.
A jet ski heads out of the Bay to the open ocean in Osterville.
Public transportation makes it easy to get around Osterville.
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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.
West Villages Elementary School in Marstons Mills has a brilliant staff and faculty.
Barnstable United Elementary School serves children in grades 4-5 and has an enrollment of 712.
Barnstable Intermediate School is dedicated to creating an equitable learning community.
Barnstable High School is a traditional public school with a modern campus.
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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.
East Bay in Osterville offers calm waters for families to take kids out and enjoy the water.
Catch stripers from the jetty at Dowses Beach in Osterville.
GreatSchools:
The GreatSchools Rating helps parents compare schools within a state based on a variety of school quality indicators and provides a helpful picture of how effectively each school serves all of its students. Ratings are on a scale of 1 (below average) to 10 (above average) and can include test scores, college readiness, academic progress, advanced courses, equity, discipline and attendance data. We also advise parents to visit schools, consider other information on school performance and programs, and consider family needs as part of the school selection process.
View GreatSchools Rating Methodology
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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
2
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 67 days on the market compared to the national average of 57 days. The median sale price for homes in Osterville, Barnstable over the last 12 months is $1,220,000, up 2% from the median home sale price over the previous 12 months.
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 WhiteWilliam Raveis Real Estate & Home Services
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
A custom home in the quaint seaside Village of Osterville! Perfectly nestled alongside Crosby Boat Yard, Nauticus Marina, Oyster Harbors Marina, The Chart Room and well-known West Bay, you will find this top of line crafted 4 bedroom, 3.5 bathroom home. Hand-selected flooring and natural lighting fill the open-concept entertaining spaces and private rooms, creating an elevated living experience.
Cynthia HoulihanBerkshire Hathaway HomeServices Robert Paul Properties
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
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 KinlinBerkshire Hathaway HomeServices Robert Paul Properties
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
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 KinlinBerkshire Hathaway HomeServices Robert Paul Properties
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
Discover the charm and convenience of this lovingly maintained ranch-style home, perfectly designed to meet all your needs. Adding to its appeal, this home is just minutes away from the idyllic coastal Main Street of Osterville Village with its charming boutiques, delightful cafes, and quaint seaside allure. The home's inviting foyer is the perfect introduction to the warmth and character that
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
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
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.
Yearly rental. Spacious 3 bedroom ranch with 1 and a 1/2 baths. Large living room with gas fireplace, dining area with French doors to outdoor entertainment size deck. Grill included. Private out door shower. Beautiful hardwood floors throughout. Convenient first level washing machine and dryer. Solar panels will have significant savings on electric bills. Newer gas furnace and newer water
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
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