A truly one-of-a-kind investment opportunity in the sought-after Chappaqua School District—2 houses for the price of one! This eclectic & historic property offers unmatched versatility, character & endless potential. Originally built in 1926 as a horse stable & previously home to a Houlihan Lawrence office, the property has served multiple uses over time, including commercial space & residential rentals. Designated as Property Class 280, this rare multi-residence offers 2 distinct homes set on a 1.122 acre parcel, featuring a total of 4,559 square feet, 6 bedrooms & 4 bathrooms. The left residence, a 2,885 SQFT contemporary barn-style home features cathedral ceilings, a spiral staircase, large back deck, & a 1,330 SQFT garage with oversized doors—perfect for a workshop, artist studio or even a car collection! Inside, you'll find 3 bedrooms & 2 bathrooms in a loft-like layout. The right residence, a 1,674 SQFT traditional-style home, offers a more classic floor plan with 3 bedrooms & 2 bathrooms, front & back porches, & an unfinished walk-out basement. Truly Special Property—Private, wooded park-like grounds, highlighted by Gedney Brook, which meanders behind both homes. Surrounded by protected land with no neighboring developments. Additional features include two separate driveways, one of which is a U-shaped driveway & parking for approximately 20 vehicles. Ideally located just minutes from both downtown Chappaqua and Mount Kisco, each offering a Metro-North station for an easy commute to NYC. Enjoy the convenience of being within walking distance to Seven Bridges Middle School and close to the North-South County Trailway, New Croton Reservoir, Kitchawan Preserve, Pruyn Audubon Sanctuary, as well as several swim and tennis clubs. Surrounded by nature and top-tier amenities—this location truly has it all. Single-family properties in this area typically generate rental income between $6,000 and $12,000 per month and sell for $1.5 million to $2 million, offering excellent potential for high-ROI, cash flow, long-term appreciation, and strong resale value—making it an ideal opportunity for investors, contractors, flippers, or future homeowners. PLEASE NOTE: Exterior viewings available by appointment (serious buyers only). No interior showings prior to submitted offers. Property is being sold STRICTLY AS- IS & CASH OFFERS are strongly encouraged. Needs full updating/renovations A rare & extraordinary opportunity in one of Westchester's most desirable areas.