Chappaqua, NY Homes for Sale with Pool

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

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

Wendy Nolan Houlihan Lawrence Inc.

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

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

"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.