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About this home
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.
Single-familyProperty Type
2026Year Built
1 acresLot Size
$562Price/Sq.Ft.
3 car garageParking
Listed by Jacob Bivona• Keller Williams Prestige Prop.
Install electrical wiring for a pump, lights, and an automatic cover.
Electrical
Mar 12, 2026 • Active
Residential pool/spa
Pool and hot tub
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Climate risks
1/10 Flood Factor
Minimal risk of a flood reaching the building in the next 30 years
1/10 Fire Factor
Unlikely to be in a wildfire in next 30 years
5/10 Heat Factor
7 days above 98° expected this year, 14 days in 30 years
6/10 Wind Factor
65% chance of strong winds in next 30 years
8/10 Air Factor
13 unhealthy days expected this year, 18 days in 30 years
Provided by First Street
Historical weather
Westport, CT • 06880
Average low and high temperatures (°F)
35
22
38
23
53
34
62
43
69
52
81
61
86
68
81
61
76
58
67
47
55
38
40
26
Jan
Feb
Mar
Apr
May
Jun
Jul
Aug
Sep
Oct
Nov
Dec
Sun exposure
82/ 100
Very good sunlight
Sunscore
There appears to be minimal shading by surrounding buildings, terrain, and vegetation.
8.7 hrs
5.2 hrs
JuneDecember
Provided by Shadowmap
Redfin Estimate for 2 Windy Hill Rd
We cannot show automated home-value estimates for this home.
Nearby homes have recently sold between $3,225,000 and $5,700,000.
Nearby comparable homes
The Redfin Estimate uses 6 recent nearby sales, priced between $3.2M to $5.7M.