Ossining, NY Houses for Sale

Welcome Home and discover this charming ranch-style residence nestled in one of Ossining’s most sought-after neighborhoods. Surrounded by nature and set on nearly an acre (0.85 acres) of beautifully landscaped property, this Single Family home offers comfort with 3 beds and 2 baths, lives like 2,000+ sq/ft with finished Basement, 2+ Car Garage, privacy, and timeless appeal.Enjoy a sun-filled

Luis Morgado HomeSmart Homes & Estates

Set in one of Briarcliff Manor's most distinctive communities, this pond-front three-bedroom townhouse offers a rare combination of natural beauty and thoughtful updates. Enjoy peaceful pond views, seasonal views of the Hudson River, and 33 acres of Olmsted-designed grounds with lush gardens and mature landscaping as your backdrop. The recently updated eat-in kitchen anchors the bright main level

Aurora Banaszek Compass Greater NY, LLC

Exquisite new 5 bedroom, 4.1 bath center hall colonial to be built offering refined luxury and timeless architectural elegance in an exceptional cul-de-sac setting. Perfectly positioned on just shy of one acre and backing the serene wooded grounds of the Edith Macy Center, this residence blends privacy, prestige, and natural beauty. A rare opportunity exists to fully customize finishes,

Mark Seiden Mark Seiden Real Estate Team

Stately, 4-bedroom Colonial with Hudson River views, ideally set on a level 2/3-acre property with exceptional curb appeal. Located within the desirable walk-to-train Scarborough neighborhood , this home offers a seamless blend of timeless architecture and modern convenience—perfectly suited for today’s Westchester lifestyle. Spanning approximately 3,500 square feet, the residence features

Betsey Relyea Houlihan Lawrence Inc.

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.

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

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.

Welcome to 75 Chappaqua Road, a total spacious 4,200 sq ft single-family home in Briarcliff Manor, offering generous living space, abundant natural light, and timeless character. The home features a traditional layout with a formal living room, family room, formal dining room, and a convenient main-level bath. The kitchen and adjoining spaces provide a practical flow into the main living areas,

Bryant Moran YourHomeSold Guaranteed Realty

One of the first Beechwood townhouses to come to market since 2023, this pondfront residence offers a rare opportunity to own within one of the area’s most coveted communities. Set directly on the pond with seasonal Hudson River views, the home pairs natural beauty with everyday convenience. A private outdoor patio overlooking the water creates a true extension of the living space, ideal for

Alexandra Shaw Corcoran Legends Realty

Welcome to this tastefully updated home Dutch Colonial. Beautifully and thoughtfully renovated, the light-filled chef’s kitchen is the true centerpiece, featuring crisp white cabinetry, expansive countertops, generous storage, and seamless flow into the dining and living areas, making it ideal for both daily living and entertaining. The large living room features a lovely wood burning fireplace

Wendy Holt Houlihan Lawrence Inc.

Beautifully updated center hall Colonial, set on a private and professionally landscaped almost one-acre property on a quiet cul-de-sac in one of Ossining’s most desirable neighborhoods. This move-in ready home blends classic architecture with modern upgrades and a highly functional layout designed for today’s lifestyle. The centerpiece of the home is the newly installed Leicht kitchen, featuring

John Oliveira Douglas Elliman Real Estate

Welcome to this beautiful split-level residence located in the Chilmark section of Briarcliff Manor. Lives like a ranch while offering the space and layout of a 4-bedroom, 2.5-bath Colonial. The updated kitchen and bathrooms reflect today’s design preferences, and the open floor plan creates a seamless flow for everyday living and entertaining.The spacious kitchen features built-in cabinetry

James Maurno Berkshire Hathaway HS NY Prop

Look no further! This affordably priced Cape is full of potential and ideally located in a lovely residential neighborhood. Offering 4 bedrooms and endless possibilities, this home is ready for your personal touch and a little TLC to truly shine. Great opportunity for homeowners or investors alike. Being sold “as is.”

Jason Kerwar William Raveis Real Estate

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 two bedroom one bath bungalow set high above the Hudson with sweeping river views, this property offers a rare opportunity to enjoy the charm, convenience, and lifestyle that define Ossining living. Welcome to 19 Samstag Ave, a home perfectly positioned for those seeking both tranquility and connectivity. Enjoy gorgeous Hudson River vistas and the natural beauty that surrounds this historic

Angelina Cozza Century 21 Alliance Rlty Group

Nestled on a quiet cul-de-sac in Briarcliff Manor, this inviting 5-bedroom, 4.5 bath home combines space, light, and a layout that simply works for the way people live today. A grand entry foyer with hardwood floors and inlay detail sets the tone, opening to well-proportioned formal and informal spaces suited for both everyday living and entertaining. The living room features recessed lighting

Suzan Zeolla Houlihan Lawrence Inc.

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

Welcome to 37 Secor Road. Being sold strictly as-is and as a buy one get one with 39 Secor Road; You cannot pass on this deal! Get this cozy 2-bedroom, 1-bathroom single family home replete with a garage, unfinished basement and unobstructed windows to the Hudson River. This home is priced to be sold as a package with the adjoining Two family home at 39 Secor Road (MLS # 973596 offered @ $675K).

Monica Cooper THD Homes LLC

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

Welcome to this wonderful and thoughtfully updated split-level home, ideally located in the heart of Ossining Village. The main level features gleaming hardwood floors and an abundance of natural light through new insulated windows. The open-concept layout seamlessly connects the living room, dining area, and updated kitchen—creating the perfect flow for both everyday living and entertaining. The

Maria Vele Keller Williams Realty Partner

Your life in Briarcliff Manor begins here; Turnkey impeccably maintained ranch in the highly sought-after Briarcliff Manor School District. Perfectly sited on a quiet street just down the street from Neighborhood Park, this rare one-level home offers effortless living in a prime Westchester suburban setting. Recent updates include young siding, young windows and a new front door, complemented by

Nancy Beard Houlihan Lawrence Inc.

Charm describes this well maintained, sunlit, low maintenance brick ranch with exceptional curb appeal. Freshly painted and truly move in ready, this home is the perfect starter home or ideal condo alternative. Step into a spacious, light filled living room with a cozy fireplace, leading to a formal dining room, perfect for entertaining. The kitchen features granite countertops, newer appliances

Emelisa Mendoza RE/MAX Town & Country

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

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.

Take A Stroll in the Park...The market has waited 50 years for this true gem of a home to become yours in this special, sought-after quiet and serene residential neighborhood in the unincorporated Town of Ossining. This light and bright three bedroom, two bath ranch house sits on a half-acre lot on the high side of Morningside Drive with beautiful scenic views, and borders the 130-acre Charles K

Cindy Cassuto Corcoran Legends Realty

You can’t ask for a more turn-key home! Everything inside has been updated tastefully in the last few years, and the shy 1/2 acre is beautifully landscaped and perfect for entertaining, with a large deck plus back patio and privacy fence in the rear. If you’re looking for a mother-daughter home, or a home office with a separate entrance, this ranch with a walk-out lower level would be perfect for

Susan Strawgate Code Houlihan Lawrence Inc.

Nestled in a quiet neighborhood near a local park, this wonderful split-level home in the highly sought-after village of Briarcliff Manor offers the perfect blend of comfort, style, and community living. Step inside to discover an updated eat-in kitchen featuring granite countertops and built-in seating—ideal for both everyday living and casual entertaining. The open-concept living and dining

Mark Seiden Mark Seiden Real Estate Team

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

Fabulous 2 bedroom contemporary colonial with loft off primary suite situated on a private cul de sac the highly desirable Rosecliff gated community. You are welcomed into a dramatic entry foyer This home has been freshly painted and offers a brand new chef's kitchen with quartz countertops and lovely white cabinetry.All new stainless steel appliances. The eat in kitchen leads to a dining

Wendy Nolan Houlihan Lawrence Inc.

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.

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.

If you’re searching for a 3-bed colonial home in Briarcliff Manor with flexible living space, walkability, and room for a 4-bedroom setup, 34 Jackson Road delivers everyday convenience just moments from the Village center, and Law Memorial Park, with pools, tennis courts, and playgrounds in the Briarcliff school district. The main level features a bright living room, formal dining room, eat-in

Edward Holmes William Raveis-New York, LLC

Experience breathtaking, panoramic views of the majestic Hudson River from this exceptional sanctuary in Briarcliff Manor, NY. Reimagined and completely rebuilt in 2011, this unique home seamlessly blends elegance with serenity, offering a true connection between indoor and outdoor living. The property is designed to immerse you in nature’s beauty, with every space thoughtfully crafted to elevate

Elizabeth Hargraves Julia B Fee Sothebys Int. Rlty