Ossining, NY

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Nestled on the eastern bank of the Hudson River, Ossining is a picturesque village brimming with historic charm and natural beauty. This friendly community offers residents a peaceful lifestyle and small-town spirit just north of New York City.


Home to about 38,846 people, Ossining strikes an appealing balance between quaint neighborhood and bustling suburb. Its population is quite diverse, with 44% Hispanic, 41% white, and 15% black residents.

In recent years, Ossining has become increasingly popular with young professionals and families drawn by its affordable real estate, strong school system, and easy commute. The population has grown 7% since 2010 as more discover Ossining’s outstanding quality of life.


Ossining traces its roots back to the 17th century when it was settled by the Sint Sinck Indians. The village was later home to American Revolution patriots like John Paulding, the captor of British spy John André.

In the 19th century, Ossining became the site of Sing Sing prison which hosted infamous inmates like gangster Lucky Luciano. The prison put Ossining on the map and shaped local culture and economy.

Vestiges of Ossining’s rich past can be seen at the historic John Paulding Manor, the prison museum, and the legendary Croton Aqueduct trail. The village takes pride in preserving its heritage.

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Quality of Life

Between the scenic Hudson River views and preserved parkland, Ossining offers outstanding recreational opportunities. Popular activities include hiking at Teatown Lake Reservation, kayaking off Sing Sing Kill, and taking Metro-North to NYC attractions.

The vibrant downtown hosts events like side walk sales, farmers markets, and summer concerts on the waterfront. Families particularly value Ossining’s top-ranked school district, safe streets, and strong sense of community.


Ossining residents have access to excellent medical facilities. Phelps Hospital is a highly ranked community hospital providing comprehensive inpatient and outpatient services just two miles from downtown. The Open Door Family Medical Center also offers affordable preventative care.

To promote healthy lifestyles, the village has developed a recreation master plan to upgrade parks, trails, and fitness resources across Ossining. This includes improvements to the Cedar Lane Park sports fields and courts.


Ossining is among Westchester County’s safest municipalities, aided by proactive community policing. Violent and property crime rates are less than half the national averages.

Responsible development strategies also help maintain security by directing growth away from hazard areas. Ossining’s high home ownership rate further encourages neighborhood stability and investment.


Ossining enjoys quick and convenient transportation access. The village has its own Metro-North commuter rail station providing a 40 minute direct ride to Grand Central Terminal.

Major highways just minutes away include Route 9, the Taconic State Parkway, and the Saw Mill River Parkway. Bee-Line Bus service efficiently connects Ossining to surrounding communities.

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Shopping and Dining

Historic downtown Ossining offers eclectic local shops, boutiques, and restaurants. The village’s diverse cuisine ranges from Italian trattorias to Ecuadorian cafes to waterside steakhouses.

Just outside the village, major retailers like Home Depot, Stop & Shop, and Stew Leonard’s provide everyday conveniences. The Cortlandt Town Center mall offers additional shopping 15 minutes north.


Ossining schools consistently rank among Westchester County’s finest. The district serves about 4,100 students across six schools including Ossining High School, a competitively ranked college preparatory public school.

Higher education options include Westchester Community College’s Ossining Extension Center which offers affordable, career-oriented programs in growing fields.

Points of Interest

  • Hudson River Museum – Fascinating exhibits on art, history, and science plus a planetarium
  • Teatown Lake Reservation – Gorgeous 834-acre nature preserve with trails, gardens, and educational programs
  • Sing Sing Prison Museum – Artifacts and stories from the notorious prison’s 200 year history
  • Louis Engel Waterfront Park – Scenic Hudson River park with walking path, playground, and outdoor concerts
  • First Baptist Church of Ossining – Historic 1898 church notable for stained glass windows designed by Louis Comfort Tiffany
  • Croton Aqueduct Trail – Hike or bike this 18-mile linear state park along the historic water channel

With its small-town warmth and abundance of natural and cultural riches, Ossining offers residents an outstanding quality of life. The village’s vibrant spirit and engaged community continue to make it a sought-after suburb.