Single Family House in Westchester County
MLS Number | 851223 |
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Address | 55 Deepwood Drive, Chappaqua, NY 10514 show map |
Price | $1,875,000 show mortgage calculator |
Acres | 1.0399908172635 |
Bedrooms | 4 |
Bathrooms | 3 / 1 |
Year Built | 1927 |
Est. Sq. Footage | 4199 |
Elementary School | Roaring Brook |
Jr High-Middle School | Robert E Bell School |
High School | Horace Greeley High School |
Estimated Taxes | $42,970 |
HOA Fees | |
Level 1 | |
Level 2 | |
Level 3 | |
Set on 1.04 level acres of beautifully landscaped property with vibrant perennial gardens and mature plantings, this impeccably renovated four-bedroom, three-and-a-half-bathroom Center Hall Colonial offers 4,199 square feet of thoughtfully designed living space in one of Chappaqua’s most sought-after neighborhoods. A gracious foyer with a classic sweeping staircase welcomes you into the home. Just off the entry, you’ll find a private office—perfect for working from home—as well as a stylish powder room. The expansive Great Room combines living and dining into one open, light-filled space, featuring a wood-burning fireplace and French doors that open to a large stone patio ideal for hosting family gatherings or enjoying tranquil afternoons outdoors. The sunny family room is perfect for everyday living, with its cozy fireplace, custom built-ins, and triple exposures overlooking the lush, level yard. Additionally, a discreet, retractable movie screen and projector descend at the touch of button, purpose built for shared family movie nights. The beautifully renovated dine-in kitchen is both warm and functional, with a walnut-topped island, casual dining area, stylish butler’s pantry and generous walk-in pantry. A charming garden room opens directly to the yard, providing another connection between indoor and outdoor spaces. The main level is completed by a play area, mudroom, and convenient laundry with double washers and dryers designed with busy households in mind. The attached two-car garage features an additional half bay for bikes, sports gear, or extra storage, with its own driveway access for added convenience. Upstairs, the tranquil primary suite is a retreat in itself, with custom built-ins, separate his and hers closets, and a luxurious spa bath. Two additional bedrooms and a full hall bath are accessed via the main staircase, while the fourth bedroom, another full bath, and a generous bonus/multipurpose room are reached by a second staircase or through Bedroom 3. The bonus space—perfect for a teen hangout, homework zone, or home gym—includes a balcony overlooking the parklike backyard. Located just minutes from the Chappaqua Swim and Tennis Club and only a seven-minute drive to the charming Village of Chappaqua—with its train station, shops, restaurants, library, and top-rated schools—this exceptional home blends timeless architecture, modern convenience, and family-friendly living in an unbeatable setting. A true Chappaqua gem!
Eat-in Kitchen, Patio, Walk-In Closet(s)

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