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2 Windy Hill Road, 
Westport, CT 06880

$4,795,000


6

Beds


8

Baths


8,185

Sq Ft


Single Family

Active

Listed by

Jacob Bivona, (203) 705-8180

Wendy Ryan

Keller Williams Prestige Prop., (203) 327-6700

Brown Harris Stevens

(203) 327-6700

Last updated:

July 3, 2026, 01:17 PM

MLS#

24182984

Source:

CT

About This Home

2 Windy Hill Road

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.

Home Facts

Single Family

8 Baths

6 Bedrooms

Built in 2026

Price Summary

4,795,000

$585 per Sq. Ft.

MLS #:

24182984

Last Updated:

July 3, 2026, 01:17 PM

Added:

23 day(s) ago


Rooms & Interior

Bedrooms

Total Bedrooms:

6

Bathrooms

Total Bathrooms:

8

Full Bathrooms:

6

Interior

Living Area:

8,185 Sq. Ft.


Structure

Structure

Architectural Style:

Colonial, Modern

Building Area:

8,185 Sq. Ft.

Year Built:

2026


Lot

Lot Size (Sq. Ft):

43,560


Finances & Disclosures

Finances

Price:

$4,795,000

Price per Sq. Ft:

$585 per Sq. Ft.

Source:CT
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.

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Contact an Agent

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Contact, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If a Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby's International Realty®). I acknowledge that I have read and agree to the terms of use and privacy notice.