Ossining, NY Houses for Sale

Full of warmth, character, and timeless appeal, this charming colonial home offers a wonderful blend of classic details, comfortable living spaces, and an exceptional location in the heart of Ossining. Set on a beautiful property with a spacious yard, this special home provides the perfect backdrop for gardening, entertaining, outdoor play, or simply enjoying a quiet evening outdoors. Inside,

Amanda Saraceno Keller Williams Realty Group

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

Now is your Chance! Back on the Market! Welcome to this beautifully maintained 1 bedroom plus den townhome in the highly desirable Liberty Knoll community. Designed for comfort and convenience, this spacious home features 2 full bathrooms plus a powder room, making it perfect for both everyday living and entertaining.The versatile den/home office offers ideal flexibility for remote work, a

Janet Brand Houlihan Lawrence Inc.

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.

Welcome to this beautifully maintained vintage Colonial, ideally situated on a desirable corner lot in the heart of the village. Combining classic character with thoughtful updates, this spacious home offers comfortable living both inside and out. The first floor features hardwood floors, high ceilings, a bright eat-in kitchen, dining room, an inviting living room, and laundry off the kitchen.

Mark Seiden Mark Seiden Real Estate Team

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

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

Welcome home to 281a Croton Dam Road. Nestled on a picturesque lot along scenic Croton Dam Road, this charming 3-bedroom home offers the perfect blend of character, comfort, and affordability. The thoughtfully designed layout features a convenient first-floor bedroom, ideal for guests, a home office, or one-level living, while two additional bedrooms are located upstairs. Filled with natural

Annette Cicinelli Keller Williams Realty Partner

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.

Nestled on a quiet cul-de-sac, this well-maintained home offers the perfect blend of comfort, functionality, and indoor-outdoor living in the Town of Ossining. The main level features an open floor plan with a spacious living and dining area, a large stone breakfast counter bar, two bedrooms, and a full bathroom. Upstairs, you’ll find two additional bedrooms with a second full bathroom, providing

Sylvia Aufiero Highline Real Estate Services

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.

Charming Cape Cod on a .23-acre lot in desirable Ossining — comfortable now with plenty of room to personalize. This 3-bedroom, 1.5-bath home offers classic curb appeal, a bright living area, and a flexible layout that adapts to your needs. The spacious yard provides room for gardening, play, or outdoor entertaining. Enjoy easy access to local shops, schools, parks, and commuter routes while

Daniel Berger RE/MAX Prestige Properties

VERSATILE "HIGH RANCH" HOME NESTLED INTO GENTLE ROLLING HILLSIDE. SOUTH WESTERN EXPOSURE, MANICURED LAWN, LOWER BRICK FRONT FACADE ACCENT, ALONG WITH GENEROUS DRIVEWAY PARKING. THE LIVING ROOM W/TRIPLE WINDOW, DINING AREA, EAT-IN-KITCHEN W/BACK YARD ACCESS, HALL BATHROOM, 2 BEDROOMS, PRIMARY BEDROOM W/HALF BATH - ARE ON THE UPPER LIVING LEVEL. THE RECREATION RM, OFFICE/GUEST BEDROOM, BATHROOM,

Greg Kane Kane & Associates

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

Welcome to 224 Willow Drive, a beautifully maintained and thoughtfully updated home offering 2,026 square feet of living space in the sought-after Briarcliff Manor community. This inviting 3-bedroom, 2.5-bath residence combines timeless charm, modern updates, and exceptional lifestyle amenities. The sun-filled interior features soaring cathedral ceilings, gleaming hardwood floors, and spacious

Dean Nugent Mary Jane Pastor Realty

Spacious and beautifully maintained raised ranch set on 2 level acres, offering the perfect combination of comfort, functionality, and flexible living space. This 4 bedroom, 3 full bath home lives like a 5 bedroom and features sun-filled interiors, hardwood floors, and charming brick fireplaces. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring rich

Mark Boyland Keller Williams Realty Partner

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

Set on two peaceful acres in the desirable New Castle area, this thoughtfully updated home offers a rare balance of privacy, space, convenience, and flexibility. Positioned on a corner lot and set far back from the road, the property provides a quiet and secluded feel while still being conveniently located approximately 15 minutes from downtown Chappaqua, the Chappaqua Train Station, shopping,

Derek Greene Greene Realty Group

Phase Two at Moradia is now offering a fabulous to-be-built new modern on Lot One. Rooted in the aesthetic of Frank Lloyd Wright's Usonia District and inspired by the classic era of mid-century design, Moradia is a brand-new community of 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

David Turner Compass Greater NY, LLC

Step into timeless elegance with this extraordinary mini estate in the heart of New Castle, just 45 minutes from New York City. Originally built in 1935 and thoughtfully reimagined for modern luxury living, this remarkable 3.91-acre property seamlessly blends historic charm with today’s most sought-after amenities.The beautifully renovated 5,337-square-foot Main House features 5 spacious

Cathy DeBow William Raveis Real Estate

Bring your vision and make this spacious split-level home your own! Set on over an acre of level, park-like property, this home offers a rare opportunity to create the lifestyle you've been dreaming of in a serene and convenient location. Freshly enhanced with newly painted exterior surfaces, a brand-new walkway, front patio, and a new above-ground oil tank, the property is ready for its next

Mark Seiden Mark Seiden Real Estate Team

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

Built in 1870 and lovingly restored by its current owners, this Queen Anne Victorian at 28 Hamilton Avenue sits in the heart of Historic Ossining. Both yards are planted with apple, cherry, Asian pear, pawpaw, hazelnut, raspberry, blueberry, and strawberry, along with a working vegetable garden — a rare thing to find alongside a home of this character. Approach through a deep front yard bursting

Zoya Litinetskaya Compass Greater NY, LLC

This well maintained 1960's Split-level home offers a rare opportunity for owner-user & investors too. The main living area offers a Living/Dining Room w/vaulted ceilg/skylight, galley kitchen w/granite counter tops. The upper level contains the Primary Bedroom, 2 add'l BR's, and Hall Bathroom. The side-yard Patio & Backyard is accessible from the Living/Dining Rm. The large backyard abuts 'The

Greg Kane Kane & Associates

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

Beautiful 4-bedroom, 2 full bath home located on a quiet cul-de-sac in Ossining, offering a comfortable layout and inviting indoor-outdoor living. The main level features an open-concept design connecting the eat-in kitchen and living room, highlighted by modern stainless steel appliances, beautiful moldings, and expansive windows that fill the home with natural light, creating an ideal setting

Joseph Lukic Compass Greater NY, LLC

PRICED TO SELL! THIS ONE WON'T LAST!!! Discover this beautifully maintained home in Hawkes Crossing, offering a comfortable layout and low-maintenance lifestyle. The home features 3 spacious bedrooms, 2.5 bathrooms, and an additional room that can be used as a 4th bedroom, home office, or flex space. The main level includes a formal dining room, an open kitchen, and a flowing floor plan that

John Buoninfante Real Broker NY LLC

Charming front porch colonial on tree lined Street. Front door opens to entry hall, large dining room and living room with hardwood floors, arched walkways between rooms. Beautifully updated kitchen with island and stainless appliances, half bath. A first floor bonus room that can be used as a bedroom or den/office. Upstairs leads to three bedrooms, a full bath, hardwood floors throughout,

Robin Schwamb North Country Sothebys Int Rlt

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.

Summer starts here! Nestled on a stunning park-like property surrounded by mature trees and lush landscaping, this beautifully maintained 3-bedroom, 3 full bathroom home offers the perfect blend of privacy, comfort, and timeless style. The sun-filled main level features an open-concept layout with gleaming hardwood floors, a spacious living room anchored by an oversized picture window overlooking

Diana Romero Houlihan Lawrence Inc.

20 Samstag Ave is the kind of home that sparks ideas the moment you enter. Tucked into an established Ossining neighborhood just minutes from the Hudson River, this classic 2-story Cape-style home with charming dormers and a cheerful red-painted front porch is ready for its next chapter, and for the right buyer, that chapter could be something special. Inside, three bedrooms, a full bath, and 930

Alex Mashkin Keller Williams Realty Partner

Welcome to the peace and tranquility of Morningside Drive. Nestled in a highly desirable location, this well-maintained home offers expansive frontage, ensuring exceptional privacy and a serene setting on almost 1 acre. The spacious primary suite features a private bath and walk-in closet, while beautiful hardwood floors run throughout the home. The inviting living room, anchored by a stunning

Fatima Candiotti 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