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MLS 24204809 For Sale Open House Updated September 20, 2026
Open House An open house is scheduled — contact us for times.
2 Windy Hill Road

Westport, Connecticut 06880

$4,600,000
On market 15 days
2 Windy Hill Road
1 / 39

About This Property

Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural stone finishes, and walls of European windows and doors. At the heart of the home, the chef's kitchen features marble countertops and backsplash, Sub-Zero and Wolf appliances, custom oak cabinetry, dual dishwashers, and a stunning waterfall island that seamlessly connects to the home's gathering spaces. The primary suite serves as a private retreat with vaulted oak-beamed ceilings, fireplace, sitting area, private balcony overlooking the pool, custom dressing room, and spa-like bath with heated floors and dual showers. Designed for both entertaining and wellness, the lower level includes a glass-enclosed gym, custom marble-topped bar, recreation space, guest suite, and a dedicated area ready for a golf simulator or theater. Outside, enjoy a gunite pool with automatic cover, covered outdoor living area, expansive granite patios, outdoor kitchen provisions, and a large flat lawn surrounded by mature landscaping, stone walls, and privacy plantings. A rare offering that delivers the comfort of everyday living with the amenities of a private resort.

Property Details

Interior

Heat
Hot Air,Zoned — Natural Gas
Cooling
Central Air,Zoned
Fireplaces
2
Basement
Full,Heated,Fully Finished,Cooled
Interior Features
Audio System Auto Garage Door Opener Cable - Pre-wired Humidifier Open Floor Plan Security System

Exterior & Lot

Roof
Metal
Construction
Construction
Pool
Gunite,Heated,In Ground Pool
Lot Description
Fence - Partial Level Lot On Cul-De-Sac Professionally Landscaped
Garage & Parking
Attached Garage

Utilities & Systems

Water Source
Public Water Connected
Sewer
Public Sewer Connected
Energy Features
Energy Star Rated Generator Ready

Community & Schools

Elementary
Long Lots
Middle
Bedford
High
Staples
Neighborhood
Long Lots
Nearby Amenities
Commuter Bus Golf Course Health Club Library Playground/Tot Lot Public Rec Facilities Shopping/Mall

Appliances

Included
Cook Top Oven/Range Microwave Range Hood Refrigerator Subzero Icemaker Dishwasher Washer Dryer Wine Chiller

2 Windy Hill Road

Westport , Connecticut 06880

$4,600,000

On market 15 days

Beds
6
Baths
8
SqFt
8,185
Type
Single Family
County Fairfield
Garage 3
Rooms -
Lot Size 1.00 Acres
Property Tax $0
Assessed Value $0
Year Built 2026
Style Colonial,Modern
Zoning AA

Payment Estimate

30-year fixed. Includes taxes; estimates only.

Estimated Monthly Payment
Open the full mortgage calculator →

Property Map

Map location is based on the property address.

Listing information is deemed reliable but not guaranteed and is sourced from the local MLS feed. Brokerage shown: 3548.

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