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    1 home
      1 home available
      27 Deepwood Hill, Chappaqua, NY 10514
      PendingPrice Increased $151,000
      27 Deepwood Hill, Chappaqua, NY 10514
      $1,550,000
      3beds
      2.5bath
      2,830sqft
      1.96acres
      House for Sale

      27 Deepwood Hill, 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.
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      OneKey® MLS
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      27 Deepwood Hill, Chappaqua, NY 10514
      Pending
      Price Increased $151,000
      $1,550,000 $151,000 
      3beds
      2full,1half bath
      2,830sqft
      1.96acres

      27 Deepwood Hill, Chappaqua, NY 10514

      City/Town:Chappaqua   Post Office: Chappaqua     

      House for Sale by Brendan PrestonHoulihan Lawrence Inc..

      Data checked -. Listing last updated 80 days ago.
      1. Overview
      2. Details
      3. More 

      Hywood Ledge is a spectacular expanded ranch in the desirable Deepwood neighborhood of Chappaqua, which presents sophisticated charm and tranquility. This cedar-shake beauty is perfectly situated at the end of a cul-de-sac on 1.9 acres, offering unparalleled privacy, yet only 5 minutes to the center of town and the Chappaqua Metro-North. The home was renovated between 2000-22 offering years of peace of mind with quality upgrades: new roof (2020); new boiler (2020); new above-ground oil tank (2020); new 1250 gallon septic tank (2020); new Marvin Elevate, divided light windows (2021); professional landscaping (2021); electrical updates that include a 220V garage car charger and a house generator interlock with electrical sub-panel (2021); Belgium block driveway (2022). A gorgeous great room with James Allan lighting anchors the house with a wood burning fireplace, across from the beautifully renovated eat-in kitchen with custom maple Omega cabinetry. A chef’s dream is complete with large Viatera Quartz countertops plus state-of-the-art Wi-Fi supported Samsung induction cooktop and Family Hub refrigerator. Stunning floor to ceiling wrought-iron doors lead to a new multi-level Trex deck perfect for outdoor entertainment. The home’s wonderfully curated renovations carry through to the first-floor primary bedroom, with an ensuite bath with Italian mosaic tile work surrounding the spa like walk-in shower accompanied by a gorgeous copper soaking tub. The lower-level features two beautiful bedrooms with their own personal full bathroom. The bonus recreation room offers numerous possibilities for additional living and workspace. The moment you drive through the stone entry pillars, you will want to call Hywood Ledge your own.

      Internet Serviceability
      Details
        Property type
      Residential
        Year built
      1950
        Heating
      Baseboard, Forced Air, Hot Water, Oil
        Cooling
      Central Air
        Total rooms
      8
        Garage
      Yes (2 space)
        City/Town
      Chappaqua
        Post Office
      Chappaqua
        Parking spots
      -
      898327
      MLS ID
      Pending
      Status
      08/12/2025
      On Market Date
        Laundry features
      Electric Dryer Hookup, Washer Hookup
        Flooring
      Hardwood, Tile
        Fireplace
      No
        Pets allowed
        Architectural Style
      Ranch
        Basement
      Crawl Space
        View
      Trees/Woods
      Interior features
      First Floor Bedroom, First Floor Full Bath, Chefs Kitchen, Eat-in Kitchen, Quartz/Quartzite Counters
      Exterior features
      Lighting
      Lot features
      Back Yard, Cul-De-Sac, Landscaped, Part Wooded, Sprinklers In Front
      Appliances included
      Cooktop, Dishwasher, Dryer, Electric Oven, Refrigerator, Washer
      Construction materials
      Frame, Shingle Siding, Stone
      Monthly taxes
      $1,882
      Yearly taxes
      $22,580
      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
      BP
      Brendan Preston
      Associate Real Estate Broker, Houlihan Lawrence Inc.
      Direct Number 
       
      Location
      Hardscrabble Road to Deepwood Drive to Deepwood Hill #27
      For Sale Nearby
      No nearby homes are For Sale Nearby.
      Recently Sold
      No nearby homes have been Recently Sold.
      27 Deepwood Hill, Chappaqua, NY 10514, is a 3 bedroom, 2 bathroom, 2830 sqft. Single Family Residence built in 1950. This property is currently available for sale and was listed on OneKey® MLS on 8-12-2025. The MLS# for this Single Family Residence is MLS# 898327.
      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