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$1,600,000 Sale Pending

  • For Sale
  • Pending
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,612 Sq. Ft.
  • 1 Car Garage
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Most "walk-to-town" homes ask you to compromise on space, privacy, or both. At 14 Crossways, you get all three. Set less than a mile from the Chappaqua station, it combines true walkability with more than 3,100 square feet of well-organized living space on a private, level half-acre. Carefully maintained and thoughtfully improved, it is also a house designed for entertaining. At its center, the kitchen acts as the engine room of the home, anchored by a substantial island and flowing directly into the family room, dining room, and screened porch. Because the porch is accessed from the kitchen, the connection between indoor and outdoor living feels particularly natural and highly practical. From the family room, the house also connects directly to the lower level, allowing the living spaces to expand easily when people spread out. The first floor also includes a dedicated office and a separate guest bedroom with a full bath, positioned to function independently from the main living areas. Upstairs, the nearly 600 square foot primary wing is set apart, offering a true sense of scale and separation, along with a walk-in closet and primary bath. Two additional bedrooms and a full bath are located on the opposite side, creating a balanced and practical second floor. The lower level adds a large recreation room, a powder room, and a custom wine cellar, giving the house a valuable secondary entertaining space that is fully integrated into the overall layout. A rare combination of scale, function, and convenience in the heart of Chappaqua.

Full Property Details for 14 Crossways

General

  • Price: $1,600,000
  • Taxes: $27,905
  • Status: Pending
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 985955
  • Updated: 6/12/2026
  • Added to Site: 74 day(s) ago

Interior

  • Number of Rooms: 9
  • Interior Features: First Floor Bedroom, First Floor Full Bath, Built-in Features, Cathedral Ceiling(s), Ceiling Fan(s), Chefs Kitchen, Double Vanity, Eat-in Kitchen, Entertainment Cabinets, Entrance Foyer, Formal Dining, Granite Counters, High Speed Internet, His and Hers Closets, Kitchen Island, Natural Woodwork, Open Floorplan, Open Kitchen, Original Details, Other, Primary Bathroom, Recessed Lighting, Soaking Tub, Speakers, Storage, Walk-In Closet(s), Washer/Dryer Hookup, Wired for Sound
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Living Room, Masonry
  • Appliances: Convection Oven, Cooktop, Dishwasher, Dryer, Electric Oven, Exhaust Fan, Freezer, Gas Cooktop, Gas Range, Microwave
  • Laundry Facilities: Yes
  • Flooring: Ceramic Tile, Hardwood

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Other Rooms

  • Laundry: Electric Dryer Hookup, Gas Dryer Hookup, In Basement, Washer Hookup

Exterior

  • Exterior Features: Lighting, Mailbox, Rain Gutters
  • Porch/Patio/Deck: Covered, Patio, Porch, Screened

Parking

  • Garage: Yes
  • Garage Spaces: 1
  • Total Spaces: 5
  • Parking Features: Driveway, Garage, Garage Door Opener, Off Street, On Street

Location

  • County: Westchester County
  • Direction Faces: East

School Information

  • High School District: Chappaqua
  • Elementary School: Douglas G Grafflin School
  • Middle School: Robert E Bell School
  • High School: Horace Greeley High School

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air
  • Heating Type: Forced Air, Natural Gas, Radiant, Radiant Floor, Other
  • Heating Zones: 2

Utilities

  • Sewer: Public Sewer
  • Water: Public
  • Utility Description: Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, Sewer Connected, Trash Collection Public, Water Connected

Structural Information

  • Architectural Style: Cape Cod
  • Detached/Attached: Detached
  • Construction: Batts Insulation, Blown-In Insulation, Foam Insulation, Recycled/Renewable Materials, Shingle Siding
  • Basement: Yes
  • Basement Desc.: Full Basement, Partially Finished, Storage Space, Walk-Out Access
  • Unfinished Attic: Yes
  • Windows: Blinds, Casement, Double Pane Windows, Drapes, Screens, Storm Window(s), Wood Frames
  • Building Size: 3612
  • Square Feet: 3,612
  • Sq. Ft. Source: Other
  • Year Built: 1960

Lot Features

  • Property View: Mountain(s), Trees/Woods
  • Mountain views: Yes
  • Lot Size (Acres): 0.51
  • Lot Size (Sq. Ft.): 22,216
  • Frontage: Municipal
  • Road Maintenance: Public Maintained Road
  • Fence: Yes
  • Lot Features: Back Yard, Cleared, Front Yard, Landscaped, Level, Near Public Transit, Near School, Near Shops, Part Wooded, Private, Sprinklers In Front, Sprinklers In Rear, Stone/Brick Wall, Views
  • Fencing (Description): Back Yard, Fenced, Wood

Financial Considerations

  • Tax Amount: $27,905

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 3600-100-008-00001-000-0001, 3600-100-008-00001-00
  • Block: 1
  • Lot Number: 50

Listed by Julia B Fee Sothebys Int. Rlty

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— 14 Crossways —

  • Julia B Fee Sothebys Int. Rlty

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NMLS#: 1598647

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NMLS#: 1598647

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Schools serving 14 Crossways

School District:Chappaqua Central School District
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 14 Crossways Get Price Alerts and Save Property

Date
Details
Price
Change
Source
4/30/2026
Listed
$1,600,000
370.59%
MLS
11/16/1999
Sold
$340,000
—
Public Record
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Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 14 Crossways

Year
Property Taxes
Change
Tax Assessment
Change
2025
$17,125
100%
$155,928
—
2024
100%
$155,928
—
2020
-100%
$155,928
—
2020
$24,576
-16%
$155,928
—
2018
$29,332
33%
$155,928
—
2017
$22,055
1%
$155,928
—
2017
$21,904
-77%
$155,928
—
2016
$96,968
349%
$155,928
—
2015
$21,595
1%
$155,928
—
2013
$21,363
—
$155,928
—
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 14 Crossways

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Down Payment
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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Julia B Fee Sothebys Int. Rlty

14 Crossways, Chappaqua, NY 10514 (MLS# 985955) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 14 Crossways is currently listed for $1,600,000 and was received on April 30, 2026. Want to learn more about 14 Crossways? Do you have questions about finding other Single Family real estate for sale in Chappaqua? You can browse all Chappaqua real estate or contact a Coldwell Banker agent to request more information.

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