OneKey® MLS
  • Buy
  • Rent
  • Commercial
  • Find an Agent
  • Fair Housing Notices
  • Language
    Price range
    $
    $
    Bedrooms
    Bathrooms
    Home type
    Square feet
    Lot size
    Heating
    Cooling
    Parking spots
    Garage
    Basement
    Year built
    Max HOA
    Down payment assistanceDown payment assistance
    Tours
    View
    More amenities
    1 home
    1 home available
    Closed Jul 14, 2025
    55 Deepwood Drive, Chappaqua, NY 10514
    $2,315,000
    4beds
    3.5bath
    4,199sqft
    1.04acres
    House for Sale

    55 Deepwood Drive, Chappaqua, NY 10514

    Listing by: Houlihan Lawrence Inc.
    1 - 1 of 1 results
    Copyright © 2025 OneKey® MLS LLC
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Equal opportunity
    Membio
    OneKey® MLS
    55 Deepwood Drive, Chappaqua, NY 10514
    Closed Jul 14, 2025
    $2,315,000
    4beds
    3full,1half bath
    4,199sqft
    1.04acres

    55 Deepwood Drive, Chappaqua, NY 10514

    City/Town:Chappaqua   Post Office: Chappaqua     

    House for Sale by Avital SoldatenkoHoulihan Lawrence Inc..

    Data checked -. Listing last updated 9 days ago.
    1. Overview
    2. Details
    3. More 

    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!

    Details
      Property type
    Residential
      Year built
    1927
      Heating
    Oil, Steam
      Cooling
    Central Air
      Total rooms
    10
      Garage
    Yes (2 space)
      City/Town
    Chappaqua
      Post Office
    Chappaqua
      Parking spots
    -
    851223
    MLS ID
    Closed
    Status
    Jul 14, 2025
    Closed
      Laundry features
      Flooring
    Hardwood
      Fireplace
    Yes
      Pets allowed
      Architectural Style
    Colonial
      View
    Interior features
    Built-in Features, Chefs Kitchen, Crown Molding, Eat-in Kitchen, Entertainment Cabinets, Entrance Foyer, His and Hers Closets, Kitchen Island, Primary Bathroom, Original Details, Pantry, Recessed Lighting, Smart Thermostat, Soaking Tub, Speakers, Stone Counters, Storage, Walk-In Closet(s)
    Exterior features
    Awning(s), Basketball Hoop, Mailbox, Playground
    Lot features
    Appliances included
    Dishwasher, Exhaust Fan, Freezer, Range, Refrigerator, Stainless Steel Appliance(s), Washer, Oil Water Heater
    Construction materials
    Frame
    Monthly taxes
    $3,581
    Yearly taxes
    $42,970.3
    Community Features
    -
    School district
    Chappaqua
    Schools
    Roaring Brook, Robert E Bell School, Horace Greeley High School
    Senior community
    No
    Common Charges
    -
    Maintenance
    -
    Additional Fees
    -
    Open Houses
    In-Person
    No upcoming in-person open houses
    Virtual
    No upcoming virtual open houses
    Contact Agent
    Avital Soldatenko
    Avital Soldatenko
    Associate Real Estate Broker, Houlihan Lawrence Inc.
    Direct Number 
     
    Location
    Hardscrabble Road to Deepwood Drive
    For Sale Nearby
    490 Main Street # B3, Farmingdale, NY 11735
    $342,000
    2beds
    1bath
    703sqft
    acres
    Co-op for Sale
    Down payment assistanceDown Payment Help

    490 Main Street # B3, Farmingdale, NY 11735

    Listing by: Signature Premier Properties
    1512 Jackson Avenue, East Meadow, NY 11554
    $804,500
    3beds
    2bath
    1,350sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    1512 Jackson Avenue, East Meadow, NY 11554

    Listing by: Realty Connect USA LLC
    355 N Iowa Avenue, Massapequa, NY 11758
    $675,000
    4beds
    1.5bath
    1,370sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    355 N Iowa Avenue, Massapequa, NY 11758

    Listing by: Realty Connect USA LLC
    2795 Oswego Street, Bellmore, NY 11710
    $726,000
    3beds
    2bath
    1,621sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    2795 Oswego Street, Bellmore, NY 11710

    Listing by: Signature Premier Properties
    66 Berkshire Road, Bethpage, NY 11714
    $1,490,000
    5beds
    4.5bath
    3,400sqft
    acres
    House for Sale

    66 Berkshire Road, Bethpage, NY 11714

    Listing by: Douglas Elliman Real Estate
    34 Blackbird Lane, Levittown, NY 11756
    $845,000
    4beds
    2bath
    2,024sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    34 Blackbird Lane, Levittown, NY 11756

    Listing by: Coldwell Banker American Homes
    254 Hamlet Drive # 254, Jericho, NY 11753
    $1,365,000
    3beds
    2.5bath
    2,710sqft
    acres
    Condo for Sale

    254 Hamlet Drive # 254, Jericho, NY 11753

    Listing by: Douglas Elliman Real Estate
    136 Land Lane, Westbury, NY 11590
    $749,000
    4beds
    2bath
    1,300sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    136 Land Lane, Westbury, NY 11590

    Listing by: Douglas Elliman Real Estate
    1 Stuart Drive, Syosset, NY 11791
    $1,210,000
    4beds
    3bath
    2,421sqft
    acres
    House for Sale

    1 Stuart Drive, Syosset, NY 11791

    Listing by: Douglas Elliman Real Estate
    30 Harrow Lane, Levittown, NY 11756
    $650,000
    4beds
    2bath
    1,238sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    30 Harrow Lane, Levittown, NY 11756

    Listing by: Keller Williams Rlty Landmark
    Recently Sold
    Closed Jul 22
    490 Main Street # B3, Farmingdale, NY 11735
    $342,000
    2beds
    1bath
    49,658sqft
    acres
    Co-op for Sale
    Down payment assistanceDown Payment Help

    490 Main Street # B3, Farmingdale, NY 11735

    Listing by: Signature Premier Properties
    Closed Jul 22
    1512 Jackson Avenue, East Meadow, NY 11554
    $804,500
    3beds
    2bath
    6,200sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    1512 Jackson Avenue, East Meadow, NY 11554

    Listing by: Realty Connect USA LLC
    Closed Jul 22
    355 N Iowa Avenue, Massapequa, NY 11758
    $675,000
    4beds
    1.5bath
    7,300sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    355 N Iowa Avenue, Massapequa, NY 11758

    Listing by: Realty Connect USA LLC
    Closed Jul 22
    2795 Oswego Street, Bellmore, NY 11710
    $726,000
    3beds
    2bath
    6,000sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    2795 Oswego Street, Bellmore, NY 11710

    Listing by: Signature Premier Properties
    Closed Jul 21
    66 Berkshire Road, Bethpage, NY 11714
    $1,490,000
    5beds
    4.5bath
    8,976sqft
    acres
    House for Sale

    66 Berkshire Road, Bethpage, NY 11714

    Listing by: Douglas Elliman Real Estate
    Closed Jul 21
    34 Blackbird Lane, Levittown, NY 11756
    $845,000
    4beds
    2bath
    7,500sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    34 Blackbird Lane, Levittown, NY 11756

    Listing by: Coldwell Banker American Homes
    Closed Jul 21
    254 Hamlet Drive # 254, Jericho, NY 11753
    $1,365,000
    3beds
    2.5bath
    1,300,225sqft
    acres
    Condo for Sale

    254 Hamlet Drive # 254, Jericho, NY 11753

    Listing by: Douglas Elliman Real Estate
    Closed Jul 21
    136 Land Lane, Westbury, NY 11590
    $749,000
    4beds
    2bath
    6,000sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    136 Land Lane, Westbury, NY 11590

    Listing by: Douglas Elliman Real Estate
    Closed Jul 21
    1 Stuart Drive, Syosset, NY 11791
    $1,210,000
    4beds
    3bath
    7,000sqft
    acres
    House for Sale

    1 Stuart Drive, Syosset, NY 11791

    Listing by: Douglas Elliman Real Estate
    Closed Jul 21
    30 Harrow Lane, Levittown, NY 11756
    $650,000
    4beds
    2bath
    6,000sqft
    acres
    House for Sale
    Down payment assistanceDown Payment Help

    30 Harrow Lane, Levittown, NY 11756

    Listing by: Keller Williams Rlty Landmark
    55 Deepwood Drive, Chappaqua, NY 10514, is a 4 bedroom, 3 bathroom, 4199 sqft. Single Family Residence built in 1927. This property is currently available for sale and was listed on OneKey® MLS on 4-23-2025. The MLS# for this Single Family Residence is MLS# 851223.
    Display of MLS Data is usually deemed reliable but is NOT guaranteed accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and should investigate the data themselves or retain appropriate professionals.
    Copyright ©2025
    BESbswy