NY
Westchester
Chappaqua
10514
55 Deepwood Drive
55 Deepwood Drive, Chappaqua, NY 10514
Share Listing
Listing Type
Single Family
Listing Status
pending
37
$1,875,000

Home Details for 55 Deepwood Drive

Price
$1,875,000
Type
Residential
Bedrooms
4
Bathrooms
4.0
Square feet
4199
Year built
1927
Lot size acres
1.04
County
Westchester
Total rooms
10
Garage
2
Days on site
149
MLS Listing#
851223
Property Description

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!

Property Features
  • House Interior
    • Built-in Features
    • Crown Molding
    • Eat-in Kitchen
    • Entrance Foyer
    • His and Hers Closets
    • Kitchen Island
    • Pantry
    • Recessed Lighting
    • Smart Thermostat
    • Soaking Tub
    • Stone Counters
    • Storage
  • Heating Information
    • Oil
    • Steam
  • Parking
    • Attached
    • Driveway
  • Cooling Information
    • Central Air
  • Water Features
    • Public
  • Utilities
    • See Remarks
  • Fire Place
    • Wood Burning
School Information
School Information for 55 Deepwood Drive, Chappaqua, NY 10514
Elementary School
Roaring Brook
Middle School
Robert E Bell School
High School
Horace Greeley High School
Listing Courtesy: Houlihan Lawrence Inc. - 914-723-8877
Presented by: Avital Soldatenko
The data relating to real estate for sale on this website comes in part from the Internet Data exchange of OneKey MLS. IDX information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information deemed reliable but not guaranteed. Copyright ©2025 OneKey MLS. All Rights Reserved
Fair Housing Notice
Transportation
Check the walk, transit, and bike score for
Neighborhood Market Statistics
See average values in the proximity of this property
Median Listing Price
Median Days on Site
Median Square Feet
Market statistics compiled from data from OneKey MLS.
EXIT REALTY PRIVATE CLIENT
75 South Broadway, Suite 430, White Plains, NY 10601
Office
914 222 1000
Request more details
Code: