Ossining, NY Homes for Sale with Acreage

Steeped in local history and once owned by the Gilded Age Van Cortlandt family, gracious Rose Lodge is an inviting and beautifully restored historic estate—not landmarked—offering modern living and exceptional privacy on 17.9 acres. The property enjoys sweeping views across a perfectly sited in-ground pool, terraced gardens, expansive flat croquet lawn, and private lake, creating a serene country

Dalia Valdes Julia B Fee Sothebys Int. Rlty

A special opportunity to own and continue the story of a living piece of history. This magnificent 15,000 SF estate, set on 8 pristine acres, was built as the private residence for Walter Law, the founder of Briarcliff Manor and a titan of industry at the turn of the 20th century. The moment you enter the grounds you instantly feel the grandeur and charm of the property. A sweeping driveway

Jamey Gelardi Houlihan Lawrence Inc.

There are homes... and then there are places that feel quietly set apart from the world around them.Tucked behind a gentle approach, on nearly four private acres in the heart of Briarcliff Manor, 36 Revolutionary Road reveals itself slowly, intentionally... like a secret meant only for those who understand what true luxury feels like.This is not just a home. This is a legacy

Elaine Wasserman Houlihan Lawrence Inc.

Experience refined new construction living at 41 Croton Dam Road, a thoughtfully designed 2026-built single-family residence set on 1.38 acres with Hudson River views. Offering 3,550 square feet of elegant living space, this 4-bedroom, 2.5-bath home blends architectural sophistication with modern functionality. The main level features 10-foot ceilings, dramatic 8-foot front entry doors, custom

Nicola Santucci Houlihan Lawrence Inc.

Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is abrand-new community of to-be-built, high-end residences. Located along a picturesque road in historic Ossining, NY, each home is set on a beautiful parcel of virgin land. The homesites are elevated and private-ranging between 1 1/2 and 3 acres. Masia, is the first

David Turner Compass Greater NY, LLC

Experience refined new construction living at 50 Austin Place, a thoughtfully designed to-be-built 2026 Colonial estate set on 11.22 private acres in the heart of Briarcliff Manor. Offering 5,775 square feet of elevated living space, this 5-bedroom, 5.5-bath residence seamlessly blends timeless architecture with modern functionality. Estimated completion Winter 2026. A dramatic double-height

Nicola Santucci Houlihan Lawrence Inc.

Welcome to 55 Hoags Cross Rd. in the desirable New Castle area of Ossining. Privately set on a level acre and surrounded by trees and natural landscaping, this property offers a rare sense of quiet seclusion: your own peaceful retreat, just moments from town, commuting routes, and everyday conveniences. This beautifully maintained split-level ranch lives like a 4-bedroom and offers exceptional

Maryanne Durr Coldwell Banker Realty

This distinctive Teatown compound made for gatherings and entertainment blends timeless craftsmanship with modern livability offering seclusion without sacrificing proximity to trains, parks, and major highways. Tucked at the end of a quiet cul-de-sac, this exceptional estate offers rare privacy on more than 3 picturesque acres while remaining conveniently close to everything. The stunning

Mary Stetson Stetson Real Estate

Fully Available. Fantastic find for nature lovers seeking total stillness away form the City hustle and bustle, just a short 1 hr train ride from Manhattan! 14.5 wooded acres with beautiful stone outcroppings and a few clearings, suitable for chickens, goats and/or horses. The property has rustic outbuildings and walking paths that connect to Teatown trails. This home has large rooms with

Helena Macintyre North Country Sothebys Int Rlt

Old Dam Farm — A Rare Hudson Valley Legacy Set on nearly 40 pristine acres bordered by over 100 acres of protected New York City watershed land, Old Dam Farm offers an unparalleled combination of natural beauty, history, and lifestyle. This remarkable estate overlooks the sparkling Croton Reservoir, creating a backdrop of breathtaking views in every season. At its heart stands a spectacular

Nancy Kennedy

Step back in time without sacrificing an ounce of comfort in this enchanting, 200-year-old hand-hewn log cabin. Nestled on 6.41 private, lush acres, this original residence offers a rare blend of romantic history and contemporary ease. The interior showcases exceptional craftsmanship, featuring original wide-plank wood floors, a majestic stone fireplace, and a genuine Dutch door. The versatile

Josephine O'Leary Weir Julia B Fee Sothebys Int. Rlty

This is a rare opportunity to own a truly exceptional residence with panoramic, year-round Hudson River views, something rarely found at this price point in Scarborough Manor. Designed for both comfort and sophistication, this expansive three-bedroom, two-bath home offers 9ft ceilings, oversized rooms, and abundant closet space throughout. The layout strikes the perfect balance between everyday

Cynthia Leite ERA Insite Realty Services

Refined and timeless, this beautifully renovated 1929 Center Hall Colonial at 273 Elm Road blends classic architectural character with sophisticated modern living. Set on over an acre of private, landscaped grounds, the show-stopping original details include soaring ceilings, graceful archways, an oversized original fireplace, and a restored vintage butler’s pantry, replete with custom millwork.

Susan Law Houlihan Lawrence Inc.

Vacation at Home! Gracious 4 bedroom, 2 1/2 bathroom, covered front porch colonial home with a gorgeous in-ground heated pool, located in a non-through street, residential neighborhood in the Town of New Castle section of Ossining. Set far back from the road, this one-acre lot offers a private backyard featuring a huge paver patio, a sprawling lawn and tree-lined backyard, including a Japanese

Susan Strawgate Code Houlihan Lawrence Inc.