Living in Ossining: A Lifestyle and Real Estate Guide to Ossining, New York

Ossining, New York—Home of “Mad Men” and Historic Landmarks

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Best Place for Architecture Admirers

Ossining has a range of historic properties for the luxury buyer. The architectural styles include Victorian Revival homes, ranches, Cape Cods, and colonials. Preserved 18th- and 19th-century farmhouses and manors with river views are a big appeal.

In 1989, the business district traditionally known as the Crescent, which is located at the central crossroads of town, was officially recognized as a historic district. It is one of the few downtowns in Westchester County that illustrates the peak of Victorian-era commercial architecture. Some of the major landmarks in the area include the bank buildings, the village hall, post office, and high school. The town also has several historic churches that were built between 1834 and 1885 and provide a chronicle for the Gothic Revival architecture style over the course of the 19th century.

Along with the famous historical buildings in town, Ossining has several landmarked houses: Jug Tavern, also known as the Davids–Garrison House, and Moorehaven. The village of Ossining’s official downtown walking tours provide insight into the town’s most prominent historic sites.

Recreational Activities in Ossining

Ossining Main Street has a good mix of shops and services. Residents will find a wider range of shopping outlets along Route 133 (Croton Avenue) and at the Arcadian Shopping Center, just off Route 9.

In Ossining, there are a host of activities and festivals that mark the changing of seasons. The Family Fall Festival and Ossining Village Fair are among the favorites. Some annual events include Ossining’s Summer Concert Series, Santa’s Breakfast, Fall Family Fun Day, and the Trick or Trunk Halloween events. There are also local farmers’ markets (held on Saturdays) and summer street fairs that bring the town together. Residents will also enjoy the family-friendly Mother Goose Time at the library, gathering with friends at coffee shops on Main Street, and participating in the activities like ballet and swim classes at the community center.

The town has two boating clubs, the Ossining Boat & Canoe Club and the Shattemuc Yacht Club, which require memberships but offer outstanding recreational activities on the river.

The nearby Teatown Lake Reservation is a 1,000-acre nature preserve and education center located in the Lower Hudson Valley. Its 15 miles of trails are a popular hiking destination on the Old Croton Aqueduct Trail, easily accessible from Route 9. The preserve also has playing fields, playgrounds, and scenic picnic spots.

Dining in Ossining

Ossining has plenty of dining options. Goldfish Restaurant on Rockledge Avenue, the Boathouse on Westerly Road, Landmark Diner on South Highland Avenue, and Café Restaurant Las Americas on Croton Avenue are all great places to enjoy with family and friends.

Schools in Ossining

Ossining is an inclusive, diverse community and the Ossining Union Free School District serves around 5,000 students, including those from nearby Briarcliff Manor and Yorktown. The district’s six schools comprise Park Early Childhood Center, Brookside Elementary School, Claremont Elementary School, Roosevelt Elementary School, Anne M. Dorner Middle School, and Ossining High School. The average SAT scores at the high school were 497 in reading, 500 in math, and 490 in writing.

What are the Commuting Options in Ossining?

Ossining is located on the Hudson River in Westchester, just 27 miles north of Manhattan. The rail journey to Grand Central Terminal takes approximately 45 minutes to an hour along the Metro-North Railroad Hudson Line. Ossining is less than an hour’s drive from Manhattan.

How Many People Live in Ossining?

As of 2018, the population of Ossining is approximately 37,948

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