2 Windy Hill Road Westport, CT $ 4,795,000
2 Windy Hill Road
$ 4,795,000
New Construction
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2 Windy Hill Road

Westport, CT, 06880
$ 4,795,000
Bedrooms6 Baths6.2 Sq 8,185

Monthly Estimate*

$ 29,524

2 Windy Hill Road, Westport, CT 06880 - Image 1
2 Windy Hill Road, Westport, CT 06880 - Image 2
2 Windy Hill Road, Westport, CT 06880 - Image 3
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2 Windy Hill Road, Westport, CT 06880 - Image 7

Single Family Home for sale in Westport, CT

for $4,795,000 with 6 bedrooms and 6 full baths, 2 half baths. This 8,185 square foot home was built in 2026 on a lot size of 1.

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. Additional photos coming soon. Showings start June 18, 2026.

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Single Family Coming Soon

Price

$ 4,795,000

Bedrooms

6

Full Bath

6

Half Bath

2

Property Type

Single Family

Taxes

$ 0

Style

Lot Size

1

Year Built

2026

Town/City

Westport

MLS | Web ID

24182984

Features
General
Zoning AA
Neighborhood Long Lots
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 1
Directions Roseville rd to Windy Hill rd
High School Staples
City Westport
Elementary School Long Lots
Sq Ft Total 8185
Year Built 2026
Style Colonial Modern
Year Built Source Owner
Pool Description Gunite Heated In Ground Pool
Energy Features Home Energy Rating Generator Ready
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Interior
Cooling System Central Air Zoned
Total Rooms 14
Basement Description Full Heated Fully Finished
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Exterior
Water Source Public Water Connected
Lot Description Fence - Partial Level Lot On Cul-De-Sac Professionally Landscaped
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* Excluded Features
List By
Jacob Bivona

Listing Agent

Keller Williams Prestige Prop.

Broker

jbivona.re@gmail.com

Email

Affordability Calculator

$29,524
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Monthly Principal & Interest
$29,524
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
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Nearby
3041933 Elementary School
1967866 Middle School
Staples High School High School
Pricing History
DatePricePrice ChangeDescription
6/10/2026$4,795,000 Listed Price

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2 Windy Hill Road, Westport, CT, 06880 is a Single Family Home for sale at $4,795,000 with 8,185 sqft and a lot size of 1. 2 Windy Hill Road has 6 bedrooms, 6.2 baths, and was built in 2026. The property's zip code is 06880 which is in Westport, CT