Homes for Sale near Ossining High School

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

Located along a peaceful cul-de-sac in Ossining, there is a quiet grace to 19 Donald Lane. This beautifully maintained home welcomes you with sun-filled rooms and a sense of calm. As you walk up the new flagstone walkway and enter through the front door, you're greeted by the spacious living room lit by bay windows setting the tone for relaxed mornings or hosting evening guests. The open layout

Luke Joachim Redfin Real Estate

ACCEPTED OFFER 12-5-2025. Welcome home to this inviting 3-bedroom, 3-bathroom residence where a thoughtful open-concept design creates a seamless flow for daily life and entertaining. The main floor is a showstopper, with a bright and airy living room with two-sided fireplace that connects effortlessly to the dining area and kitchen. Preparing meals is a dream in this designer kitchen with

Denyse Fecteau Denyse M. Fecteau

Welcome to 14 Gates Avenue, a unique opportunity in the heart of Ossining. This charming single-family home is being sold as-is, offering endless potential for renovation, expansion, or investment. Included in the sale is a valuable additional parcel of land, providing added privacy, space, or future development possibilities. Set on a quiet, tree-lined street, this property features a classic

Tim Rothman Compass Greater NY, LLC

Picturesque Country Setting.. Colonial Farmhouse on 2.5 Beautiful Acres Adjacent to the 1,000 Acre Teatown Lake Reservation Preserve.. Light and Bright with Picture Windows Overlooking the Private Waterfront on Lincoln Pond with Boat Dock and Expansive Views.. Custom Kitchen with Island and Wolf Range, Plenty of Cabinetry with Underlighting, Granite Counters, Tile Backsplash and Tile Flooring,

Vincent Vetrano Douglas Elliman Real Estate

This Charming Village Colonial comes complete with a classic front porch and swing, offering the perfect spot to relax and enjoy your surroundings. Welcome home to this beautiful 3 bedroom, 1.5 bath Colonial that seamlessly blends timeless character with modern updates.The inviting living room with fireplace and custom built-in bookcases create a warm, welcoming space ideal for both relaxing

Janet Brand Houlihan Lawrence Inc.

Great Investment Opportunity in the Heart of Ossining! This 2-bedroom, 1-bath single-family home is perfect for contractors, investors, or handy buyers looking to build equity. Perfect opportunity to design, renovate and add value. Zoned for a two-family home, this property offers the opportunity for future expansion and conversion (buyer to verify). Conveniently located near local shops,

Wendy Galvan Century 21 Marciano

EXCEPTIONAL Ossining legal 2 family: Unbeatable Location near the bustling downtown.This duplex built in 1989 offers ideal owner occupy.......live in One unit and rent the second to help carry costs...or a great opportunity for investor.. 3 level unit with cozy fireplace, family room and wood deck for summer entertaining.. The second unit has 2 bedrooms and bath..But the perks don’t stop

Jayne Begley William Raveis Real Estate

All About the View!Come experience stunning vistas all day long and magical sunsets every evening from this beautiful end unit at Eagle Bay. As you enter this gated community, you’ll immediately sense how special it is—meticulously maintained grounds and amenities that include tennis, pickleball, a fitness center, pool, playground, and more. Step inside the home and you’re greeted by hardwood

Patricia D'Alesio Houlihan Lawrence Inc.

Built circa 1900 - this Victorian home offers Hudson River & Palisades views from the wrap-around front porch. A large side-hall entry welcomes you, along with the dark staircase balusters carved in the canonical classic style. Oak floors, high ceilings, a formal dining room with wood burning FPL and sliding pocket doors leading into the living room, are all appreciated amenities. The Kitchen

Greg Kane Kane & Associates

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

Eagle Bay! Discover serene living in this first floor - no steps - 1 bedroom condominium home. Eagle Bay has incredible grounds with gardens, flowering trees and incredibly maintained homes, all in a gated community. Large living and dining room, updated eat-in-kitchen and a large bedroom with ample closets. Private outdoor space with privacy and wooded views. Clubhouse, pool, tennis, pickle

Nancy Kennedy

This spacious three-family home in Ossining offers three full stories plus a finished basement, perfect for multi-generational living or rental income. Each unit features its own living areas, kitchen, and bedrooms, providing privacy and flexibility for family members or tenants. The first floor includes a living room, central kitchen and dining area, three bedrooms, and a full bath. The second

Etan Hakimi Mitra Hakimi Realty Group LLC

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

The Essence of Westchester Luxury. A Grand Briarcliff Manor Estate Nestled on 3.83 Private Acres. Perfectly positioned between the Hudson River and Sleepy Hollow Country Club. World-class dining, shopping and Metro North train are nearby, blending convenience with serene privacy. The stately home boasts five spacious ensuite bedrooms, including a spectacular primary suite with a cozy

Elaine Wasserman Houlihan Lawrence Inc.

FREE 12 MONTH HOME WARRANTY that covers electrical/plumbing/appliances/and MORE! This historically charming Center Hall Colonial Farmhouse is situated on almost an acre of pristine land. Own a piece of Westchester County history with this 1826 built farmhouse, enjoy 7' high ceilings, wide planked hardwood floors, and three working fireplaces. HUGE dry walkout basement with an enormous walk-up

Justin Landon Howard Hanna Rand Realty

Beautiful riverfront SOHO style loft in converted 1800s brick schoolhouse facing the Hudson River, close to train, restaurants, riverfront, marinas, summer concerts on the river and all that glorious Hudson Valley riverfront life has to offer. Enjoy one level living in this fabulous open plan unit at the best corner spot in the building, with 14 foot ceilings and 10 foot windows, facing the

Lynn Harmonay North Country Sothebys Int Rlt

Expanded 6 bedroom, 3 bath home on fenced-in property! Property is over assessed by 10% and taxes are based on a market value of $778,000. Once sold, the assessment may be grieved. This spacious home offers comfort, functionality, and room to grow. Nestled on a lovely level lot, the property features a newly painted rear deck, a storage shed, and a fully fenced yard—perfect for outdoor enjoyment.

Mark Seiden Mark Seiden Real Estate Team

Exciting 2-bedroom condo in the Village of Ossining! Enjoy the lifestyle of convenience. Walk to train, restaurants, stores, farmers market, festivals, waterfront park, community recreation center, library, and more. Cats and dogs friendly (limit 2 per unit)! As an owner, you can obtain a parking permit for both the village and train station. This property is a part of "fair and affordable"

Igor Krasnoperov Rising Star Realty

Sprawling Cape Cod style home with first floor primary suite on a fabulous, private setting. Kitchen has stainless appliances and stone counters, formal dining room has large bay window looking out at the fenced-in property, and living room has high ceilings and a fireplace. Sun Room off the kitchen has 3 skylights and the covered patio off the kitchen overlooks the lush landscaping, backing up

Mark Seiden Mark Seiden Real Estate Team

Welcome to this single-family home located in the heart of the vibrant town of Ossining. This residence features an inviting open-concept floor plan that offers excellent flow perfect for both everyday living.The main level includes a spacious living and dining area that seamlessly connects to the kitchen, along with a conveniently located first floor bedroom. Upstairs, you'll find two

Susan Fraietta BHHS River Towns Real Estate

Discover a rare investment opportunity or your new home with this fully occupied multifamily home, set on an oversized lot along a quiet residential street. With abundant on-site parking plus two car detached garage and long-term tenants, this property offers immediate stability and impressive future upside. Current rents are below market, presenting significant potential for value growth. The

LOUIS BUDETTI JR ERA Insite Realty Services

Welcome to 63 Cedar Lane – Your Hudson River Retreat! Perched on one of Ossining’s most sought-after streets, 63 Cedar Lane is a beautifully renovated 4-bedroom, 3-bathroom single-family home that perfectly blends modern luxury with breathtaking natural beauty. Enjoy sweeping Hudson River views from the oversized, maintenance-free deck. Watch the harvest moon rise and the fall foliage glow,

Cindy Kief Corcoran Legends Realty

Turn key home with HUDSON RIVER VIEWS. This move-in-ready home, expertly renovated, offers a bright open floor plan and chef-inspired kitchen with quartz countertops, stainless steel appliances, and heated floors. Two modern baths also feature radiant heat. Step outside to your private oasis with multi-level deck, refreshing pool, and breathtaking year-round Hudson River views. Significant

Christopher Simao Julia B Fee Sothebys Int. Rlty

Nestled in the heart of the picturesque Hudson Valley, this stunning Tudor-style mansion is a true dream estate. Boasting an impressive 9,481 sq ft of living space, this magnificent property is situated on 50 acres of meticulously landscaped gardens, making it one of the most sought-after locations in the county.The estate features a 3-acre lake with a charming boathouse, a sparkling

Dalia Valdes Julia B Fee Sothebys Int. Rlty

2BR Apartment Included! Welcome to this stunning 5-bedroom, 3.5-bath Ossining home offering 3,400 sq ft of beautifully designed living space — including a 900 sq ft legal accessory apartment with 2 bedrooms, its own fireplace, and a private ground-level entrance. Perfect for multi-generational living, long-term guests, or excellent rental income potential. Tucked away at the end of a semi-private

Frank Petrella eXp Realty

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

Welcome to Briarcliff Woods—one of Ossining’s most sought-after condominium communities! This rare and expansive 3-bedroom, 2-bath end unit offers an exceptional blend of style, comfort, and convenience. The updated eat-in kitchen features granite countertops and ample cabinetry, while the massive living room with a perfectly appointed fireplace and custom built-ins sets the tone for gracious

Lisa DaRos Houlihan Lawrence Inc.

LOOK OUT ON THE TREETOPS from this sunny 1-bedroom plus den co-op apartment in the sought-after riverfront community of Scarborough Manor. Updated with new carpeting and recently painted, this unit features a fully renovated kitchen with quarry tiled floor, new cabinets, granite countertops, farmhouse sink, and new appliances. Off the kitchen is a bonus room for a den or office. The 24 x 13 ft

Elizabeth Dolan Corcoran Legends Realty

This beautifully updated home now features several new upgrades, including a fully reconstructed floor on the main level, professionally rebuilt for lasting stability and comfort. Step back in time and discover the charm of this turn-of-the-century cottage, nestled in the heart of the historic Campwoods Grounds Community. Enjoy the unique blend of community living and the privacy of a

Mark Seiden Mark Seiden Real Estate Team

Nestled in the heart of Ossining, this charming two-family home combines space, flexibility, and opportunity under one roof. Offering three full stories plus a finished basement, it features multiple living areas, two kitchens, and plenty of bedrooms, making it ideal for multi-generational living or rental income.The first unit includes a welcoming living and dining area, two spacious

Etan Hakimi Mitra Hakimi Realty Group LLC

Fully renovated duplex with Hudson River views in the heart of Ossining. Buy and hold investors welcome or live in one and rent the other. This rare offering features a recently modernized space, flexible layout, large double deck, and expansion potential. Dual access from both Hamilton Avenue and James Street, the property includes parking for upwards of 8 vehicles and private driveway access.

Giancarlo Pecora eXp Realty

Welcome to 113 Antler Ridge in Ossining, NY – a spacious condo full of potential, nestled in the desirable and well-maintained Deerfield community. This home features a functional layout with abundant natural light and a solid foundation to build upon. It’s the perfect opportunity for buyers to design and customize a space that truly reflects their own style.The main level offers an

Evan Attinger Schunk Realty Group