Home / Listings / Westport
Active · For Sale
$4,795,000

2 Windy Hill Road, Westport, Connecticut 06880

6 beds 8 baths 8,185 sq ft Single Family For Sale Built 2026

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.

Status
Active
Type
Single Family For Sale
Price
$4,795,000
Beds
6
Baths
8
Interior
8,185 sq ft
Lot
1 ac
Year Built
2026
MLS #
24182984
ZIP
06880
Days on Market
53
Heat
Natural Gas · Hot Air, Zoned
Cooling
Central Air, Zoned
Water
Public Water Connected
Sewer
Public Sewer Connected
Parking
Attached Garage (3-car)
Laundry
Upper Level

Flood risk: check the FEMA flood map for this address.

Schools

Elementary
Long Lots
Middle / Jr High
Bedford
High School
Staples

Interior

Appliances
Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
Basement
Full, Heated, Fully Finished
Attic
Pull-Down Stairs
Fireplaces
2
Total rooms
14

Building & Exterior

Style
Colonial, Modern
Roof
Metal
Siding
Vertical Siding, Wood
Exterior features
Balcony, Gutters, Lighting, French Doors, Underground Sprinkler, Patio
Foundation
Concrete
Pool
Gunite, Heated, In Ground Pool
New construction
Completed/Never Occupied

Lot & Land

Zoning
AA
Lot
Fence - Partial, Level Lot, On Cul-De-Sac, Professionally Landscaped

Energy

Energy features
Home Energy Rating, Generator Ready

Public record

From the Westport assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

Year built1963
Living area2,144 sq ft
Total rooms9
Lot size1 acres
Stories1
HeatHot Water
ExteriorClapboard
Assessed value$582,900
Town appraisal$832,600
Last recorded sale2014

Recorded sales

Deed transfers on file with the Westport land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.

Listing courtesy of Keller Williams Prestige Prop. — Jacob Bivona · (203) 327-6700

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