2 Windy Hill Road, Westport, Connecticut

$4,600,000

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6

Beds

8

Baths

8,185

Square feet

1.00

Acre

About 2 Windy Hill Road

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.

Features of 2 Windy Hill Road

MLS® # 24204809
Price $4,600,000
Bedrooms 6
Bathrooms 8.00
Full Baths 6
Half Baths 2
Square Footage 8,185
Acres 1.00
Type Single Family For Sale
Style Colonial, Modern
Status Active

Community Information

Address 2 Windy Hill Road
Area Long Lots
City Westport
County Fairfield
State Connecticut
Zip Code 06880

Amenities

Features Energy Star Rated, Generator Ready
Parking Attached Garage
# of Garages 3
Is Waterfront No
Waterfront Not Applicable
Has Pool Yes
Pool Gunite, Heated, In Ground Pool

Interior

Interior Features Audio System, Auto Garage Door Opener, Cable - Pre-wired, Humidifier, Open Floor Plan, Security System
Appliances Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
Heating Hot Air, Zoned, Natural Gas
Cooling Central Air, Zoned
Fireplace Yes
# of Fireplaces 2
Has Basement Yes
Basement Full, Heated, Fully Finished, Cooled

Exterior

Exterior Vertical Siding, Wood
Lot Description Fence - Partial, Level Lot, On Cul-De-Sac, Professionally Landscaped
Roof Metal
Foundation Concrete

School Information

Elementary Long Lots
Middle Bedford
High Staples

Additional Information

Date Listed September 4th, 2026
Days on Market 31
Zoning AA
RE / Bank Owned No

Listing Details

OfficeKeller Williams Prestige Prop.

Listing Map

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Listing information last updated on October 6th, 2026 at 2:44pm EDT.