Opportunities like this do not come around often in Chappaqua, and when they do, they tend to move quickly. What is being offered at 58 Maple Ave is a flat, level, in-town parcel with an existing 2-bedroom, 1-bath cottage set back from the road among towering pines, in one of Westchester County's most coveted villages. Whether a buyer chooses to develop the land, renovate what is there, or simply occupy the existing structure while planning next steps, the opportunity here is defined first and foremost by the location and the lot.
The cottage itself, built in 1930 and totaling 711 square feet, is being sold strictly as-is. It sits on a 0.28-acre lot with driveway parking and includes a front deck, a patio, and a yard with a quiet, private feel that genuinely surprises you given how close you are to the center of town. Inside, the main level includes a great room with cathedral ceilings and built-in features, a kitchen, two bedrooms, and a full bath. A partial basement with Bilco door access houses laundry and mechanicals. The structure has a history as a consistently rentable asset in a market where rental demand is strong and vacancy is rare, which speaks to the enduring appeal of this particular address regardless of what a future owner ultimately decides to do with it.
The location is the defining feature and the reason this property commands the attention it does. You are minutes on foot from the Chappaqua Metro-North Station, putting Midtown Manhattan within comfortable commuting distance without the stress of a car or a parking lot. The village's boutique shops, restaurants, and parks are equally walkable, giving this address an everyday livability that most Westchester properties simply cannot replicate. For those who travel frequently for business, Westchester County Airport is also easily accessible. This is a genuinely rare convergence of walkability, transit access, and village character that defines the upper end of what Chappaqua real estate has to offer.
The property falls within the Chappaqua Central School District, one of the most highly regarded public school systems in New York State and a consistent driver of demand in this market.
Flat lot, set-back privacy, walk-to-train location, and Chappaqua schools.

Move in ready Colonial that perfectly balances classic charm with tasteful updates. This home has been meticulously maintained and features a bright, inviting interior. The kitchen serves as the heart of the home, updated with white shaker cabinets, granite countertops, an oversized island, and a full suite of stainless steel appliances. For added convenience, the first floor includes a dedicated laundry room with extra cabinet storage, and a full bathroom. The exterior is equally well kept with a roof, siding, and gutters that are only a few years old, plus a brand new sliding door installed in March. Outside you will find a spacious back deck overlooking a fully fenced yard with perennial gardens and a Japanese maple, offering a private space for relaxing or entertaining. There is even clever storage space tucked away under the deck. The upper levels provide three bedrooms and a full bathroom, along with a walk up attic that offers excellent flex space for a home office, gym, or playroom. Located just minutes from Garnet Health, local shopping, and major highways, this home is incredibly convenient for commuters. For those looking for a seamless move, the seller is open to potentially including furniture and security cameras. If you are not in the market to buy, the owner is also offering a 1 to 2 year rental option at $3,500 a month. Total annual taxes are $6,522.21, which includes city, county, school, and trash collection. 9 Chestnut is ready for its new chapter.