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Sean O'Shaughnessy
Licensed Real Estate Salesperson
REALTOR®
Cell: (607) 287-0030

14 Crossways, Chappaqua, NY 10514

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Property Description

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.

14 Crossways | MLS# 985955

This single family home located at 14 Crossways, Chappaqua, NY 10514 is currently listed for sale with an asking price of $1,600,000. This property was built in 1960 and has 4 bedrooms and 3 full and 1 partial baths with 3138 sq. ft. Crossways is located within the Chappaqua school district. Search Chappaqua real estate on sean-oshaughnessy.timberlandproperties.com today.

Gallery

Property Features

Property Type: Residential - Single Family
Basement: Full, Partially Finished, Storage Space, Walk-Out Access
Basement: Yes
Cooling: Central Air
Fenced: Yes
Fireplaces: 1
Garage: 1
Heating: Forced Air, Natural Gas, Radiant, Radiant Floor, Other
Home Style: Cape Cod
Lot Size: 0.51 Acres
Taxes: $27,905
Year Built: 1960

Amenities

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
Lighting
Mailbox
Rain Gutters

Feature Descriptions

Appliances: Convection Oven, Cooktop, Dishwasher, Dryer, Electric Oven, Exhaust Fan, Freezer, Gas Cooktop, Gas Range, Microwave
Attic: Partial, Pull Stairs, Unfinished
Building Area Total: 3612
Days on Site: 3
Exterior: Batts Insulation, Blown-In Insulation, Foam Insulati
Fencing: Back Yard, Fenced, Wood
Fireplace Features: Living Room, Masonry
Fireplace Y/N: Yes
Flooring: Ceramic Tile, Hardwood
Formal Dining: Yes
GarageY/N: Yes
Heating Zones: 2
House Faces: East
Laundry: Electric Dryer Hookup, Gas Dryer Hookup, In Basement, Washer Hookup
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
On Market Date: 2026-04-30
Parcel Number: 3600-100-008-00001-000-0001, 3600-100-008-00001-00
Parking Features: Driveway, Garage, Garage Door Opener, Off Street, On Street
Parking Total: 5
Patio And Porch: Covered, Patio, Porch, Screened
Rental Term: Monthly
Road Responsibility: Public Maintained Road
Rooms Total: 9
Sewer: Public Sewer
Special View Info: Mountain(s), Trees/Woods
Utilities: Cable Connected, Electricity Connected, Natural Gas Connected, Phone Connected, Sewer Connected, Trash Collection Public, Water Connected
Water: Public
Window Features: Blinds, Casement, Double Pane Windows, Drapes, Screens, Storm Window(s), Wood Frames
Wooded: Yes

Local Schools

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

Estimate Your Payment

Estimated Payment

$ 6,352.99 per month $3,560.91 Principal & Interest $2,325.42 Property Tax $466.67 Homeowner's Insurance

Change Payment Information

%
years/fixed
yearly
yearly (est.)
(Payments are an estimate and may vary by lender)

Demographics

Listed By / Shown By

Listing By

Agency Name: Julia B Fee Sothebys Int. Rlty
Agency Phone: 914-234-0200

Shown By

Agent Name: Sean O'Shaughnessy
Agent Phone: Cell: (607) 287-0030
Agency Title: Timberland Properties

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