$4,795,000
Active2 Windy Hill Road
Westport, Connecticut, 06880 · Fairfield County
6
Beds
8
Baths
8,185
Sq Ft
2026
Built
MLS # 24182984
Price / Sq Ft
$586
Property Type
Single Family For Sale
Lot Size
1
Class
Property
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
2 Windy Hill Road, Westport Connecticut 06880 — Single Family For Sale listed at $4,795,000.
At a Glance
6
Bedrooms
8
Bathrooms
8,185
Sq Ft
1
Lot Size
--
Garage
2026
Year Built
The Details
Property Details
Other Details
Property Features
Location & Community
All Photos (45)
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This listing is +231% vs the Westport median. Verify against same-school-district comps before competing offers.
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$4,795,000
Listing Agent
Jacob Bivona
Keller Williams Prestige Prop.