2 Windy Hill Road, Westport, CT 06880 (MLS # 24182984)

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PRICE $4,795,000 dsIDX morgage calculator
BEDS 6
BATHS 7
HOME SIZE 8,185 sqft
LOT SIZE 43,560 sqft

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.

DAYS ON MARKET 1 LAST UPDATED 6/10/2026
YEAR BUILT 2026 GARAGE SPACES 3.0
COUNTY Fairfield STATUS Active
PROPERTY TYPE(S) Single Family

SCHOOLS
Elementary School Long Lots
Jr. High School Bedford
High School Staples


ADDITIONAL DETAILS
AIR Central Air, Zoned
AIR CONDITIONING Yes
APPLIANCES Cooktop, Dishwasher, Dryer, Gas Water Heater, Humidifier, Ice Maker, Microwave, Oven, Range, Range Hood, Refrigerator, Washer, Wine Cooler
BASEMENT Finished, Full, Yes
CONSTRUCTION Frame, Vertical Siding, Wood Siding
EXTERIOR Balcony
FIREPLACE Yes
GARAGE Attached Garage, Yes
HEAT Forced Air, Natural Gas, Zoned
INTERIOR Entrance Foyer, Open Floorplan, Sound System
LOT 1 acre(s)
LOT DESCRIPTION Cul-De-Sac, Level
PARKING Garage Door Opener, Attached
POOL DESCRIPTION Gunite, Heated, Outdoor Pool, In Ground
SEWER Public Sewer
STYLE Colonial, Modern
WATER Public
ZONING AA
MORTGAGE CALCULATOR
   

TOTAL MONTHLY PAYMENT

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Listing courtesy of Keller Williams Prestige Prop.
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This IDX solution is (c) Diverse Solutions 2026.

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