$1,762,766Average Value$772Average Price per Sq Ft46Homes 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.
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Osterville Demographics and Home Trends
On average, homes in Osterville, Barnstable sell after 59 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 $1,187,000, down 5% from the median home sale price over the previous 12 months.
Price Improvement! Opportunity awaits in this coveted Osterville neighborhood. Bring Your Vision to Life With Over 3300 Sq Ft of Living Space. Radiating curb appeal, this home has been lovingly maintained by the same owners since it was built nearly 50 years ago. Set on a double lot, the mature landscaping shines in every season! New central AC, Generator, irrigation, a shed, composite deck and
Exceptional 3-BR Family/Vacation Home in Osterville: Nestled in a well-maintained neighborhood in the desirable village of Osterville. This spacious and inviting 2116 sf 3 BR home would be an ideal primary residence or your Cape Cod getaway retreat. Beautiful hardwood floors throughout the main floor. Upstairs-2 spacious guest bedrooms and a loft/study room. This home features an impressive
Perfectly situated within a 5-minute drive of the beach, Main Street Osterville shopping and restaurants, and Route 28, which opens all of the Cape to exploration and fun, this gracious 4-bed, 4-bath home offers a peaceful retreat where timeless coastal charm meets effortless outdoor living. Set among mature trees and beautifully groomed landscaping, the wooded setting creates privacy and a sense
Beautifully renovated, 23 & 27 Swift Avenue is a rare two-parcel Osterville offering totaling approximately 1.11 acres, moments from Osterville Village. The charming 3-bedroom residence sits on approximately .66 acre and is conveyed with an adjoining approximately .45-acre parcel, creating exceptional privacy and intriguing future potential. Recent improvements include a new roof and brand-new
LIKE-NEW IN OSTERVILLE’S COVETED WIANNO AREA! Rare opportunity to own a free-standing condo/golf villa offering effortless luxury and low-maintenance Cape Cod living. Built in 2023 and lightly lived in, this beautifully appointed home is moments from Osterville Village, Wianno Golf Club, Dowses Beach, marinas, shops and dining. The light-filled interior features soaring ceilings, hardwood floors
LIKE-NEW IN OSTERVILLE'S COVETED WIANNO AREA! Rare opportunity to own a free-standing Osterville condo/golf villa offering effortless luxury and low-maintenance Cape Cod living. Built in 2023 and lightly lived in, this beautifully appointed home is moments from Osterville Village, Wianno Golf Club, Dowses Beach, marinas, shops and dining. Natural light pours through the open, airy interior
Beautifully renovated and thoughtfully improved, 23 & 27 Swift Avenue is a rare two-parcel Osterville offering totaling approximately 1.11 acres, just moments from Osterville Village. Set on approximately .66 acre, the charming 3-bedroom residence is conveyed with an adjoining approximately .45-acre parcel, creating exceptional privacy and intriguing future potential. Recent improvements include
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
Set in desirable Osterville, 30 Deerfield Road is a beautifully reimagined three-bedroom, three-bath residence offering effortless coastal living just minutes from the beach. Recently transformed through a comprehensive interior and exterior renovation, the home blends timeless Cape Cod character with fresh, sophisticated finishes and modern comfort. The thoughtfully designed layout is
This elegant Cape-style residence offers a refined retreat on a sprawling, wooded lot near Osterville Village and Dowses Beach. Defined by bright, voluminous spaces, the home features a stately pillared portico, stone walkways, and classic shingle siding. Inside, the center hall layout leads to a grand living room with a two-story wall of windows and a Palladian arch. This flows into the dining
Paul GroverBerkshire Hathaway HomeServices Robert Paul Properties
Incredible value at this new price in Osterville Heights!! Move right into this sun-filled, open-concept ranch with one-car garage and oversized shed set on a private and spacious partially-fenced park-like backyard perfect for adding a potential pool, outdoor entertaining, barbecues, lawn games and relaxing with family and friends. New improvements include enhanced landscaping, fresh paint, new
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 KinlinBerkshire Hathaway HomeServices Robert Paul Properties
Welcome to the beautiful village of Osterville on Cape Cod located in the heart of town, close to many stores & restaurants & only 1 mile to Dowses Beach. This newly built home was custom designed by Barnstable Harbor Builders including many high end features such as: quartz counters, Thermador appliances, red oak HW floors & custom trim detail, beadboard ceilings, & crown molding. The home is
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
Immaculate totally furnished winter rental with private deck, private access, and parking. WINTER RENTAL ONLY: Available to April 30... possibly a little longer. Maximum 2 people. NO SMOKING.NO PETS. Shorter term furnished rental possible, but prefer a 6 month minimum. Rate is for 6 mo rentalss. Located in the heart of Osterville village is this quaint renovated Townhome (1/2 Duplex) fondly
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