Osterville, MA

Dowes Beach in Oysterville, MA

Situated on the south side of Cape Cod, Osterville is a quaint Massachusetts village full of breathtaking views, classic architecture, and an affluent population. Its scenic shoreline overlooks Nantucket Sound – making it one of the most sought-after destinations for travelers worldwide.

With a population of about 3,100 people, Osterville is home to some premier eateries, stores and galleries. Its popular attractions include Dowses Beach; the ideal spot for swimming and boating in the sun alongside its magnificent shoreline; The Wianno Club – an elite country club hosting tennis courts, golf courses and luxurious dining facilities – as well as The Osterville Historical Museum which displays artifacts illustrating the town’s history.


Osterville is renowned for its stunning waterfront properties and lavish manors. With many marinas, yacht clubs, and waterways, the village has become a revered hotspot among sailors and boaters alike.

There are plenty of opportunities for outdoor recreation in Osterville. The village has several parks and conservation areas, including the Wianno Golf Course, which offers a challenging 18-hole course with stunning views of Nantucket Sound. The nearby Osterville Fish Pier provides fishing charters and tours of the local waters.

Osterville is an idyllic village with a distinguished past and dynamic present. All who visit or live here can take pleasure in its stunning beauty, tremendous culture, and indulgent amenities – it truly has something for everyone!


Osterville, MA can trace its roots all the way back to when it was first settled in the early 1800s. It mainly served as a small fishing and farming community but then quickly changed once affluent families from Boston and New York discovered this paradise’s serenity – making it their go-to summer hot spot!

The famed Crosby family arrived in Osterville to build their legacy during the late 1800s, contributing significantly to its growth. Not only did they construct an extravagant estate overlooking West Bay, but also a beloved boathouse on East Bay which still stands today and serves as a cherished landmark for locals and tourists alike.

In the early 1900s, a consortium of savvy entrepreneurs created the Wianno Club, a prestigious country club featuring golf, tennis and yachting. Sooner than expected it had become an integral part of Osterville’s social life for affluent families spending their summer holidays here.

During World War II, Osterville served an indispensable function by hosting the construction of Quonset hut buildings for military use. The village’s growth and success continued long after the war ended when it welcomed many soldiers who had trained at nearby Camp Edwards on Cape Cod to become a part of their community.

Today, Osterville is a thriving community with a rich history that is reflected in its architecture, landmarks, and traditions. The village has managed to maintain its small-town charm while also becoming a popular destination for tourists and second-homeowners who are drawn to its natural beauty, luxury amenities, and rich cultural heritage.

Geography and Climate:

Nestled on a coastal peninsula off the southern shore of Massachusetts’ Cape Cod, Osterville is an idyllic village lined with miles of white sand beaches and bayside views.

Surrounded by Nantucket Sound and its natural harbor, this picturesque spot offers  safety from storms and turbulent waters – making it easy to understand why so many come here seeking solace in nature’s beauty!

The geography of Osterville is characterized by rolling hills, sandy beaches, and rocky shores. The village is surrounded by several bodies of water, including West Bay, East Bay, and the Centerville River, which provides access to Nantucket Sound.

The climate in Osterville is classified as humid subtropical, which means that it has warm summers and cool winters. During the summer months, temperatures typically range from the mid-70s to mid-80s (°F), while winter temperatures can drop down to the mid-30s (°F). The spring and fall seasons are mild and pleasant, with temperatures in the 50s and 60s (°F).

The village experiences a moderate amount of precipitation throughout the year, with an average of around 46 inches of rainfall annually. Snowfall is also common during the winter months, with an average of around 30 inches of snowfall per year.

Osterville’s stunning geography and temperate climate make it the perfect destination for outdoor activities throughout all four seasons, while also providing a cozy home atmosphere.

Business and Economy:

Osterville beckons visitors and second-homeowners from across the United States with its affluent commercial environment, high-end stores, exquisite eateries, and thrilling leisure activities. The village stands out as a premier destination for luxury living and unparalleled experiences.

One of the main economic drivers in Osterville is the hospitality industry, which includes hotels, restaurants, and retail shops. Many of the businesses in the village cater to affluent customers who are looking for a luxurious vacation or second-home experience. Some of the notable businesses in Osterville include high-end clothing stores like Puritan Cape Cod, luxury yachts and boats from Oyster Harbors Marine, and upscale restaurants like Wimpy’s Seafood Cafe and Grille.

In addition to the hospitality industry, Osterville also has a strong real estate market, with many affluent individuals investing in second homes or vacation properties in the area. The village’s natural beauty, luxury amenities, and rich cultural heritage make it an attractive destination for those looking to purchase a piece of the Cape Cod lifestyle.

Osterville is a thriving and vibrant place, with its economy closely linked to the luxurious experiences it offers tourists. Whether you’re visiting or are lucky enough to call this gorgeous village home, there’s something for everyone – from top-notch restaurants and recreational activities to high-end retail stores. In Osterville, affluence abounds!

Attractions and Activities:

Osterville has an abundance of amazing attractions and activities to explore for both visitors and locals alike. From beaches to museums, here are some exciting experiences you won’t want to miss:

  1. Beaches: Osterville has several beautiful beaches, including Dowses Beach, Joshua’s Pond Beach, and Craigville Beach, which are popular for swimming, sunbathing, and water sports.
  2. Boating and Fishing: Osterville’s location on Nantucket Sound makes it a great spot for boating and fishing. Visitors can rent a boat or go on a fishing charter to explore the area’s waterways and catch some fish.
  3. Golfing: The Wianno Club, located in Osterville, offers a top-notch golfing experience with a challenging course and beautiful views. 
  4. Shopping: Osterville has a variety of high-end shops and boutiques, including clothing stores, art galleries, and specialty shops.
  5. Dining: The village is known for its upscale dining options, including seafood restaurants, steakhouses, and cafes.
  6. Historical Landmarks: Osterville has a rich history that is reflected in its architecture and landmarks. Visitors can explore historic sites like the Crosby Mansion and the Wianno Club.
  7. Outdoor Recreation: In addition to beaches and boating, Osterville offers plenty of opportunities for outdoor recreation, including hiking, biking, and kayaking.

Osterville is the perfect destination, no matter your age or interests. From its unique attractions to a variety of activities, there’s something for everyone – families, couples and solo travelers alike!

Dining and Shopping:

Osterville offers a plethora of luxurious dining and shopping experiences that have been tailored to the wealthy visitors drawn to this area. Here are some popular selections:


  1. Wimpy’s Seafood Cafe and Grille: This popular seafood restaurant has been a mainstay in Osterville for over 80 years, serving up fresh seafood dishes and classic American cuisine.
  2. Five Bays Bistro: This cozy bistro offers an upscale dining experience with a menu featuring French-inspired cuisine made with fresh, locally sourced ingredients.
  3. Crisp Flatbread: This artisanal pizza restaurant specializes in wood-fired flatbreads made with local and organic ingredients.
  4. Amie Bakery: This charming bakery offers a variety of freshly baked breads, pastries, and desserts, as well as breakfast and lunch items.
  5. Earthly Delights: This health-conscious restaurant offers a variety of vegan and vegetarian options, as well as fresh juices and smoothies.


  1. Puritan Cape Cod: This high-end clothing store offers a wide selection of designer clothing, shoes, and accessories for men and women.
  2. Osterville Fish: This gourmet food market offers a variety of fresh seafood, including lobsters, clams, and oysters, as well as prepared foods and specialty items.
  3. Osterville Fine Art and Antiques: This art gallery and antique store features a collection of fine art, antiques, and collectibles from around the world.
  4. Oyster Harbors Marine: This luxury boat dealership offers a wide selection of high-end yachts and boats, as well as maintenance and repair services.

Osterville offers an abundance of dining and shopping opportunities to please any palate or budget.

Real Estate and Living:

A charming New England village, Osterville is a sought-after living destination and tourist attraction in Barnstable, Massachusetts. With its pristine beaches, captivating architecture, and first-rate school system – it’s no wonder why visitors are enchanted by this picturesque haven.

The real estate market in Osterville is quite strong, with a range of properties available at different price points. The median home price in Osterville is around $1.2 million, with many properties ranging from $500,000 to over $10 million. Homes in Osterville typically feature beautiful, traditional Cape Cod-style architecture, with many located in quiet, tree-lined neighborhoods or situated along the coast.

Living in Osterville offers a great quality of life, with easy access to a wide range of amenities and activities. The village has a variety of shops, restaurants, and galleries to explore, as well as several parks and nature preserves for outdoor recreation. In the summer months, the village comes alive with visitors, and residents can enjoy a range of seasonal events and activities.

Osterville is also located near several other popular Cape Cod destinations, including Hyannis and Chatham, offering easy access to even more amenities and attractions.

Additionally, the area is known for its excellent schools, including the Barnstable Public Schools and a number of private schools.

Osterville provides an idyllic, peaceful atmosphere for people seeking to bask in the sublime serenity of Cape Cod. On top of that, it has a thriving real estate market and first-rate quality of life.

Education and Employment:

The quaint village of Osterville, Massachusetts is a part of the larger town of Barnstable. While there are several educational and employment options available in this small community, residents often look to nearby Cape Cod for more extensive opportunities.

Osterville has access to the comprehensive educational system provided by Barnstable Public Schools, which covers every corner of Barnstable. The 11 schools within this district feature seven elementary schools, two middle schools and two high schools scattered across the town. Despite not having any school facilities located in Osterville itself, several nearby institutions serve the students of this village perfectly well.

In addition to public schools, there are several private schools located in the greater Barnstable area, including Cape Cod Academy and St. Francis Xavier Preparatory School.

Although Osterville is mainly a residential area, there are abundant job opportunities in the larger Cape Cod region. Healthcare, hospitality, retail and construction industries all have numerous openings for eager workers with various skillsets. Moreover, prominent employers such as Cape Cod Healthcare and the Cape Cod Commission are available to provide jobs across different fields like healthcare services or regional planning positions. With its stunning beauty and diverse work atmosphere, this corner of Massachusetts provides an ideal place to call home while achieving career success!

Despite having few occupations and educational choices within Osterville’s environs, the village is located in an expansive metropolitan area where plentiful employment and learning opportunities are available to its inhabitants.


Osterville, Massachusetts is situated on Cape Cod, so transportation options are somewhat confined; however there are a few ways to explore the village and its surrounding Barnstable region.

One of the most popular transportation options in Osterville is driving. The village is easily accessible via Route 28, which runs through the heart of the village. There is ample street parking available in the village, as well as several public parking lots.

Public transportation is also available in the greater Barnstable area, with the Cape Cod Regional Transit Authority (CCRTA) providing bus service throughout the region. The CCRTA offers several routes that run through Osterville, connecting the village to other Cape Cod destinations like Hyannis, Falmouth, and Provincetown.

Additionally, taxi and ride-sharing services like Uber and Lyft are available in the area, providing another option for transportation.

For those traveling longer distances, the nearest major airport is Logan International Airport in Boston, which is approximately 70 miles north of Osterville. Additionally, there is a small regional airport, the Barnstable Municipal Airport, located in nearby Hyannis, which offers flights to several destinations on the East Coast.

Despite having a few transportation options in Osterville, locals and tourists can still conveniently reach the city as well as Barnstable without difficulty. Different modes of transport are available to cater to everyone’s needs.

Community and Events:

Residents of Osterville, Massachusetts take great pride in their close-knit community and rich history. Every year, the village hosts several unique events to celebrate this special culture and welcome everyone into a vibrant atmosphere of tradition.

One of the most popular events in Osterville is the Osterville Village Stroll, which takes place in early December each year. The Stroll features live music, food, shopping, and other holiday-themed activities, and draws visitors from all over Cape Cod. 

On Fridays from June through September, Osterville hosts the beloved Farmers’ Market. This lively event features beautiful handmade crafts and vibrant live entertainment. Moreover, it is an amazing opportunity to celebrate local businesses and farmers with its range of locally-grown produce!

In addition to this spectacular market, Osterville offers other annual highlights such as the Cape Cod Baseball League All-Star Game organised at Lowell Park each summer along with the renowned Osterville Fishing Tournament which has been held every year since 1935.

Beyond these larger activities, Osterville also has a selection of community organizations and clubs such as the Osterville Garden Club, the Historical Society, and the Business & Professional Association. These groups provide locals with an opportunity to take part in their community while protecting its unique atmosphere and elegance.

The Osterville community is a close one, and its citizens are proud of their heritage as well as the yearly festivals that bring people together in joyous celebration. Residents have many opportunities to come together through special occasions and organizations, truly making it an incredible place to call home.


Osterville, Massachusetts is leading the way when it comes to creating a sustainable future by implementing various initiatives and programs that reduce its carbon footprint.

Sustainability has become an urgent global concern – and this small village on Cape Cod is doing its part!

The Osterville Village Association’s Green Initiative is a remarkable effort to encourage and implement environmentally sustainable practices in the village. Through this initiative, we can reduce energy consumption and promote recycling while inspiring alternate transportation methods like cycling or walking. By doing our part to protect our environment, we are making an impact on preserving the planet for generations to come!

To further emphasize sustainability in the town of Barnstable, which includes Osterville, several measures have been taken. These range from a pledge to reduce greenhouse gas emissions and encourage renewable energy sources to efforts towards preserving natural resources and diminishing waste.

To advance eco-friendly transportation, the town has initiated a myriad of programs such as bike sharing and an expansive system of bicycle lanes and trails.

While a few additional efforts could be made to promote sustainability in Osterville and Barnstable as a whole, many initiatives and programs are currently being employed with the purpose of mitigating our carbon footprint and encouraging green living.

Places To See and Things To Do:

Whether you’re a local or an out-of-towner, Osterville, Massachusetts has something to offer everyone. From its picturesque beaches and historic homes to its dynamic culture and plethora of activities – it’s no wonder why this charming village on Cape Cod is one of the most sought after destinations in the area!

One of the most popular attractions in Osterville is Dowses Beach, a beautiful stretch of sand that is ideal for swimming, sunbathing, and water sports. The beach is located just a short walk from the village center and offers stunning views of Nantucket Sound.

Another must-see attraction in Osterville is the Wianno Club, a historic private club located on the shores of West Bay. The club features a beautiful golf course, tennis courts, and a private beach, and offers a glimpse into the village’s rich history and culture.

For those interested in history, the Osterville Historical Museum is a must-visit destination. The museum is housed in an historic home and features exhibits on the area’s maritime history, local art and culture, and more.

In addition to these attractions, Osterville also has a variety of shops, restaurants, and galleries, making it a great place to explore and discover unique local treasures. Some popular spots include the Osterville Fish Market, where you can find fresh seafood and homemade chowder, and the Tumi Ceviche Bar and Ristorante, which offers delicious Peruvian cuisine and craft cocktails.

Don’t miss out on the Osterville’s many yearly festivities, like the Osterville Village Stroll, Farmers’ Market, and Fishing Tournament. These occasions are a perfect chance to embrace Osterville’s distinctive culture and bond with its natives.

Healthcare Options:

As the preeminent provider of healthcare services in the region, Cape Cod Healthcare boasts numerous places throughout Barnstable County. For instance, their Hyannis home base -Cape Cod Hospital- offers an exhaustive selection of medical care including emergency treatment and surgery as well as imaging facilities.

Located in Osterville, the esteemed Medical Center provides both primary care and specialized services such as cardiology and gastroenterology. Not only that, but many other nearby clinics offer a range of medical needs to meet all your healthcare requirements.

For those who require behavioral health services, Cape Cod Healthcare system provides a broad selection of mental health and addiction treatment programs across the region.

Furthermore, Osterville is home to various alternative healthcare options such as acupuncture and massage therapy practices that supplement traditional medical care.

Osterville residents are empowered with various health care choices, ranging from classic medical services to holistic alternatives, allowing them to obtain the necessary support for enhancing and sustaining their well-being.


Osterville, Massachusetts is a beautiful village located on Cape Cod, offering a unique blend of history, culture, and natural beauty. From the captivating coastlines and stately residences to the spirited locals and vibrant customs, Osterville has something for everyone. But in spite of its beauty, incidents can still occur here just as they can anywhere else. If you or a family member have been hurt while visiting this area, it is critical to get legal advice from an experienced personal injury attorney right away.

Attorney Steven Snow is a highly-respected personal injury attorney with extensive experience representing clients on Cape Cod and throughout Massachusetts. With a deep commitment to client advocacy and a proven track record of success, Attorney Snow is the ideal choice for those in need of legal representation for personal injury cases.

Don’t hesitate to get in touch with Attorney Steven Snow if you or someone close to you has been hurt in Osterville or the nearby areas. Schedule your consultation today and find out more about how he can assist you in securing just compensation for your injuries and damages. With his professional guidance, attaining a successful outcome is within reach; enabling you to focus on recuperation while confident that a knowledgeable advocate is standing by your side every step of the way.

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