Chappaqua, NY Homes for Sale with Garage

Exceptional new construction opportunity in the highly sought-after Chappaqua School District, currently being built with anticipated completion in August 2026. Early buyers will have the rare chance to customize many of the final finishes and tailor the home to their personal style. This thoughtfully designed home offers 4 bedrooms and 5.1 bathrooms, with a highly desirable layout that lives

Karin Kimtis Compass Greater NY, LLC

Nestled in the heart of the coveted Lawrence Farms East neighborhood, 14 Annandale Road is a rare offering that seamlessly blends timeless sophistication with modern comfort on one of Chappaqua’s most desirable streets. Set on beautifully manicured, park-like grounds, this classic four-bedroom residence exudes understated elegance from the moment you arrive. A gracious approach leads to a

Sari Shaw Compass Greater NY, LLC

Exciting all new construction by highly regarded local builder, Tavo Development, along with noted architect Teo Siguenza, aiming for a Fall 2026 completion. This refined, 5,712 sq ft Colonial blends classic architecture with sophisticated modern living. The light-filled main level, with 10’ ceilings, offers a seamless open floorplan featuring a chef’s kitchen with island and service pantry,

Brian Milton Compass Greater NY, LLC

A Rare Opportunity Where History Meets Modern Living.Built in 1750 and thoughtfully renovated. White clapboard, black shutters, cedar shake roof, and copper gutters set a timeless exterior, framed by professionally designed grounds.A wide entry hall opens to living and dining rooms bookended by floor-to-ceiling stone fireplaces. Hardwood floors and detailed millwork mark the quality

Harriet Libov Houlihan Lawrence Inc.

Nestled in a beautifully wooded neighborhood within the highly sought-after Chappaqua school district, this stately 3-bedroom(lives like 5), 4-bathroom colonial is a rare find. Bursting with natural light and distinctive architectural details, 33 Greenbriar Drive presents like an estate.The striking exterior sets the tone with Juliet balconies, cupolas topped with copper weathervanes,

Wendy Nolan Houlihan Lawrence Inc.

Nestled in breathtaking natural surroundings, this modern architectural masterpiece by renowned designer Myron Goldfinger offers three levels of striking contemporary design. The residence features a soaring three-story curved ceiling, a dramatic floating staircase, and expansive open-plan living and entertaining spaces that frame the home’s private setting. The main-level primary suite provides

Tianying Xu Houlihan Lawrence Inc.

Welcome to this timeless and stunning Colonial, sited on 1.3 beautifully landscaped, private acres. This gracious 4-Bedroom Colonial blends classic architectural details with modern amenities -- open renovated kitchen with large island w/seating, spa-like bathrooms, new windows, solar paneling, Sonos throughout, a 2-bedroom cottage over the garage for long term guests, and a stunning Shoreline

Victoria Miller Compass Greater NY, LLC

Classic 1920 Colonial brimming with vintage charm and modern updates, ideally located on a desirable cul-de-sac just a short walk to town. This beautifully maintained 4/5-bedroom home features 2 renovated full baths plus a new powder room, a sparkling white renovated kitchen with floor to ceiling cabinetry, stainless steel appliances-Sub Zero, Miele, & Viking and a generous eat-in area with door

Sena Baron William Raveis-New York, LLC

Welcome to this sophisticated carriage home at 17 Lila Lane, offering a rare blend of contemporary luxury and maintenance-free living within the prestigious Chappaqua Crossing community. The thoughtfully designed layout is anchored by a gorgeous chef’s kitchen, featuring a large center island with ample seating and a premium JennAir appliance package. Equally enticing is the coveted first-floor

Jocelyn Cloder Compass Greater NY, LLC

Welcome to 2 DeWitt Drive — a stunning 2025-built carriage home offering refined luxury and effortless living in one of Chappaqua’s most desirable communities. This light-filled corner residence spans 3,574 square feet with 2 spacious bedrooms (lives like a 3BR) and 3.5 baths, thoughtfully designed with high-end finishes and sophisticated upgrades throughout. Expansive windows flood the home with

Joann Galluccio William Raveis-New York LLC

Most “walk-to-town” homes ask you to compromise on space, privacy, or both. At 14 Crossways, you get all three. Set less than a mile from the Chappaqua station, it combines true walkability with more than 3,100 square feet of well-organized living space on a private, level half-acre. Carefully maintained and thoughtfully improved, it is also a house designed for entertaining. At its center, the

Jonathan Cape Julia B Fee Sothebys Int. Rlty

Just north of NYC, this move-in ready CHAPPAQUA home delivers effortless, elevated living—done RIGHT.3 min drive to Metro North station - 48 min ride to Grand Central Station * Set behind a long private driveway with an attached 2-car garage and expansive front yard, the property captures stunning sunset views, with golden hour pouring in the best way. Inside captures a calm, grounded palette

Bianca Siani eXp Realty

1906 Grandeur. 2026 Luxury: The Ultimate Gated Sanctuary. Perched majestically atop a private hilltop, this gated 7,800-square-foot, five-bedroom estate presents a rare convergence of Gilded Age prestige and contemporary luxury. Believed to have been commissioned in 1906 for railroad magnate A.H. Smith, the residence has been masterfully renovated to honor its historic soul, featuring original

Joanna Rizoulis Julia B Fee Sothebys Int. Rlty

REHOBETH. A New Castle Landmark and on the National Register of Historic Places. Horace Greeley’s original stone barn, circa 1857. The first stone and cement structure built in the states converted to a residence in 1892 by one of Greeley’s daughters. They commissioned architect Ralph Adams Cram to remodel it into their house, which they named Rehoboth. Dramatic and impressive spaces with high

Benjamin Ginnel Ginnel Real Estate

"VICTORIAN SPLENDOR" - A unique opportunity to own an early Grand Victorian home on park-like property with 3 fireplaces, a pool and a barn.Designated a New Castle George Carpenter Historic Landmark dating back to 1780. As you enter the main entrance a flood of natural light welcome you. The two-story projection of the façade’s central section, rising to a peak at the roofline, along

Alicja Bohmrich Houlihan Lawrence Inc.

Welcome to this move-in-ready 2-bedroom, 2-bath residence in highly sought-after Chappaqua Commons. Recently refreshed with thoughtful updates throughout, this sun-filled home combines modern finishes with effortless convenience.The spacious open-concept living and dining area features brand-new flooring (2025) and a seamless flow to the updated kitchen, boasting new countertops and

Sari Shaw Compass Greater NY, LLC

Welcome to 88 Farm Lake Crescent, a beautifully maintained three-bedroom, two-and-a-half-bath residence in the highly desirable Old Farm Lake community in Chappaqua.Bathed in natural light, this inviting home offers a thoughtfully designed floor plan ideal for both comfortable living and effortless entertaining. Sliding glass doors open to a private deck overlooking Farm Lake, creating a

Joanna Rizoulis Julia B Fee Sothebys Int. Rlty