Chilmark, NY homes for sale & real estate

Chilmark, NY Homes for Sale

This one is a true delight. Lovingly cared for by the same family for 50 years, this beautifully maintained 1912 Ossining home has been thoughtfully expanded over time, with additions that feel completely seamless and create an easy, natural flow throughout its 2,217 square feet. A welcoming foyer opens to a generous living room and separate sitting room, offering wonderful spaces to gather, relax, and entertain. The eat-in kitchen connects easily to the formal dining room, where a charming built-in corner cabinet adds just the right touch of character. Also on the main level is a beautifully renovated full bath with a step-in shower, along with a flexible room currently used as an office t

Chilmark, NY Homes for Sale

Picture yourself unwinding by the fireplace, hosting summer dinners on your large deck, and gathering around the firepit under the stars. This inviting two-story Colonial on a cul-de-sac in Ossining offers 4 bedrooms, 2 bathrooms, a garage, and a basement. The backyard has room to play, entertain, and enjoy outdoor activities, with raised garden beds and a peach tree, blueberry and blackberry bush ready to inspire your green thumb. With supermarkets, schools, highway and the train close by, everyday convenience complements the comfort of home. Come see the possibilities and make this home your own!

Chilmark, NY Homes for Sale

Welcome to 1 Mundet Drive! This lovingly updated, no-step ranch sits on a desirable cul-de-sac near the Briarcliff Manor border, with easy access to everything you need. Gorgeous and move-in ready, the home features three well-proportioned bedrooms, an updated full bath, hardwood floors, crown molding, a wood-burning fireplace, and lots of charm throughout! The spacious backyard seamlessly extends the living space, offering plenty of room for play, gardening, outdoor dining, and entertaining. Step outside to the attached covered patio, creating a comfortable three-season space that flows naturally to the expansive deck - perfect for relaxing and enjoying the outdoors. A newly resurfaced dr

Chilmark, NY Homes for Sale

A rare Mid-Century Modern by noted Westchester architect Roy Sigvard Johnson, whose work reflects Frank Lloyd Wright’s organic design principles, 543 Scarborough Road is bordered by protected conservation land adjoining the Old Croton Aqueduct State Historic Park. Featured in House & Garden Building Guide and HisTOURy’s 2025 architectural tour series, the home’s sculptural rooflines, dramatic geometry and walls of glass draw the wooded landscape into the interiors from the moment you enter. A welcoming entry leads to the dramatic step-down living room, where a substantial brick fireplace and floor-to-ceiling glass overlook the stone terrace and surrounding landscape.

Chilmark, NY Homes for Sale

Opportunity awaits at this 2-bedroom, 1-bath bi-level co-op in the High Meadow Cooperative! This home offers comfortable, functional living that has been lovingly lived-in and ready for your personal touch, it's a great chance to build equity and make it your own. The monthly maintenance covers heat, hot water, sewer, trash, and grounds — a simple, low-hassle way to own. Commuters will love the location: about 1 mile to the Scarborough Metro-North station for an easy 45-minute ride to Grand Central, plus shopping and restaurants nearby. Don't miss this value-priced opportunity in a convenient location! Make your appointment today!

Chilmark, NY Homes for Sale

Bring your furniture and move right into this beautiful top-floor co-op in Highland Terrace! From the moment you enter, you will appreciate the spacious foyer with hardwood floors, suitable as a entryway drop zone, office space, or breakfast nook. Just beyond is the open galley-style kitchen, featuring granite countertops, a tile backsplash, and a double-basin sink with an under-sink water filtration system. The kitchen opens seamlessly to the living and dining area, complete with a breakfast bar that’s perfect for casual meals or entertaining. The living space features BRAND NEW carpeting, which continues into both bedrooms, and the entire unit has been freshly painted. Down the hall