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2 Windy Hill RoadWestport, CT 06880

For Sale

$4,600,000

Smart Buyer Rebate $46,000

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.

Listed by Jacob Bivona

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Keller Williams Prestige Prop.

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(203) 705-8180

Last updated October 30, 2026

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Source: SmartMLS #24204809

Listing Facts

  • TypeSingle-family
  • NeighborhoodWestport
  • Bedrooms6
  • Bathrooms8
  • Days on Prevu57
  • Size8,185 sqft
  • Price per sqft$562

Location

Mortgage Calculator

Listing History

09/04/2026
Listed by Keller Williams Prestige Prop.
$4,600,000
  1. 09/04/2026$4,600,000
    Listed by Keller Williams Prestige Prop.

Property Details for 2 Windy Hill Road

Exterior

Construction

  • New Construction: Completed/Never Occupied
  • Roof: Metal
  • Year Built: 2026
  • Architectural Style: Colonial
  • Construction Materials: Frame

Features

  • Pool Features: Gunite, Heated, In Ground Pool
  • Pool Private: Yes
  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Fence - Partial, Level Lot, On Cul-De-Sac, Professionally Landscaped
  • Lot Size Acres: 1.00

Financial

Taxes

  • Parcel Number: 999999999
  • Tax Year: 25

Interior

Features

  • Appliances: Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
  • Fireplaces Total: 2
  • Interior Features: AUDIO, DROPEN, PREWIRED, HUMID, OPEN, SECURESY

Rooms

  • Basement: Full, Heated, Fully Finished, Cooled
  • Bathrooms Full: 6
  • Bathrooms Half: 2
  • Bathrooms Total Integer: 8
  • Bedrooms Total: 6
  • Rooms Total: 14

Parking

Parking

  • Attached Garage: Attached Garage
  • Garage Spaces: 3

Schools

Elementary School

  • Elementary School: Long Lots

High School

  • High School: Staples

Middle or Junior School

  • Middle Or Junior School: Bedford

Utilities

Equipment

  • Cooling: Central Air, Zoned
  • Heating: Hot Air, Zoned
  • Laundry Features: Upper Level
  • Sewer: Public Sewer Connected
  • Water Source: Public Water Connected

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 6 bedrooms and 8 bathrooms in this single-family home at 2 Windy Hill Road.

What schools are nearby to 2 Windy Hill Road?

Nearby schools include the Long Lots Elementary School, Bedford Middle School, and Staples High School.

Does this single-family home have parking?

Yes, there are 3 parking spaces available for 2 Windy Hill Road.

How does 2 Windy Hill Road compare to other single-family homes in Westport?

This single-family home is listed 18% below the average price for single-family homes in Westport and has been on the market for 12 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 8,185 sqft.

2 Windy Hill Road is a 6-bedroom, 8-bath single-family home for sale in Westport CT 06880. Listed on Prevu for 57 days at $4,600,000. This property features 8,185 square feet of living space, located in Westport. The median listing price for single-family homes in this area is $4,797,500. Nearby schools include Long Lots Elementary School, Bedford Middle School, and Staples High School. View other single-family home listings in Fairfield County.

The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed. Copyright 2026 SmartMLS, Inc.

Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.