Claudia Dixon

2 Windy Hill Road

Westport, CT
$ 4,600,000 Beds 6 Baths 7 Sq 8,185
Monthly Estimate* How much can I afford?

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 Family

  • Price
  • $ 4,600,000
  • City
  • Westport
  • Bedrooms
  • 6
  • Full Bathrooms
  • 6
  • County
  • Fairfield
  • Half Bathrooms
  • 2
  • Area
  • Lot Size
  • 1 Acres
  • Zip
  • 06880
  • Sqr Footage
  • 8,185
  • Year Built
  • 2026
  • Style
  • MLS#
  • 24204809
Listed By: Jacob Bivona 203-705-8180 with Keller Williams Prestige Prop.. - (203) 327-6700
Data Source: Smart MLS

Features

General

Zoning AA
Neighborhood Long Lots
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Active
Acres 1
Directions Roseville rd to Windy Hill rd
High School Staples
City Westport
Elementary School Long Lots
Sq Ft Total 8185
DOM 16
Year Built 2026
Style Colonial,Modern
Year Built Source Owner
Pool Description Gunite,Heated,In Ground Pool
Energy Features Energy Star Rated,Generator Ready

Interior Features

Cooling System Central Air,Zoned
Total Rooms 14
Basement Description Full,Heated,Fully Finished,Cooled

Exterior Features

Water Source Public Water Connected
Lot Description Fence - Partial,Level Lot,On Cul-De-Sac,Professionally Landscaped

Amenities

  • Foreclosure
  • Views
  • Short Sale
  • New Construction
  • Adult 55+
  • Lease To Own
  • No HOA Fees
  • Furnished
  • Primary On Main
  • Air Conditioning
  • Seller Finance
  • Green
  • Fixer Upper
  • Horse
  • Golf
  • Fireplace
  • Deck
  • Garage
  • Basement
  • Pool

Affordability Calculator

$3,786

Per Month

Based on the average sale price from the Torrington, CT office

  • Monthly Principal & interest $2,658
  • Monthly Property Taxes $1,062
  • Monthly Home Insurance $67
Adjust Payment Options
Agent Photo

Let's determine your purchasing power. Working with my mortgage partner, you'll have the information you need to shop for a home with confidence.

Default based on a 30-year fixed rate of 6.49% 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.

Mortgage calculator provided courtesy of Inside Real Estate.

Schools

Elementary School Long Lots Elementary School
Middle School Unknown Middle School
High School Staples High School

Price History

9/4/2026 Listed $4,600,000

Property vs Zip Code Average in 06880

Price
AVG $4.45M
$4.6M
Year Built
AVG 1983
2026

In The Neighborhood

Areas That We Cover

2 Windy Hill Road Westport, CT is a Single Family Home for sale at $4600000 with 8185 sqft and a lot size of 1 Acres Acre(s). 2 Windy Hill Road Westport has 6 bedrooms, 6 baths and was built in 2026. The property's zip code is 06880 which is in Westport, CT

*Information deemed reliable but not guaranteed.

Financial calculator disclaimer: Default based on a 30-year fixed rate of 6.49% 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.

Mortgage calculator provided courtesy of Inside Real Estate.

All information deemed reliable, but not guaranteed, and should be independently verified. The real estate information and related content displayed on this site is provided for consumers personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.

Claudia Dixon

Claudia Dixon

Sales Associate

860-881-7725

By pressing Contact Me, you agree that Weichert® may contact you via phone about your inquiry, which may involve the use of automated means. You are not required to consent as a condition of purchasing any property, goods or services. For any other information please read our Privacy Policy