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Single family home for sale at 2 Windy Hl Rd, Westport, CT 06880 | MLS# 24204809 | Listing updated on 2026-10-30
Photo 1 of Single family home for sale at 2 Windy Hl Rd, Westport, CT 06880 | MLS# 24204809 | Listing updated on 2026-10-30
Photo 2 of Single family home for sale at 2 Windy Hl Rd, Westport, CT 06880 | MLS# 24204809 | Listing updated on 2026-10-30
Photo 3 of Single family home for sale at 2 Windy Hl Rd, Westport, CT 06880 | MLS# 24204809 | Listing updated on 2026-10-30
Photo 4 of Single family home for sale at 2 Windy Hl Rd, Westport, CT 06880 | MLS# 24204809 | Listing updated on 2026-10-30
35+
Beds Icon

Street View

$4,600,000

Monthly Est:$22,896

  • Beds Icon6 Beds
  • Beds Icon
    8 Baths
  • Beds Icon8,185sqft

2 Windy Hl Rd, Westport, CT 06880

$22,896/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 2026

  • $-- HOA

  • 1 acre lot

  • $562/sq.ft

Description

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.

  • Houzeo last checked: 5 minutes ago
  • Listing updated: October 30, 2026 at 4:18 am
  • Listing Provided by: Jacob Bivona | Keller Williams Prestige Prop.
  • Source: SMART MLS-CT | MLS#: 24204809 SMART MLS-CT

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Fairfield County

  • City

    Westport

  • Neighborhood

    --

  • Year Built

    2026

  • HOA Fees

    -

  • Finished Area

    8,185 sqft

  • Lot Size

    1 acre lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24204809

  • MLS Status

    Active

  • Days on Market

    56

Open House

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Location

HOA Management

0

HOA Fees

$-/

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 6

    Bathrooms: 8

Interior

  • Heating

    Natural Gas, Zoned

  • Appliances

    Cook Top, Oven/range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller

  • Interior Features

    Audio System, Auto Garage Door Opener, Cable Pre Wired, Humidifier, Open Floor Plan, Security System

  • Cooling

    Central Air, Zoned

  • Sewer

    Public Sewer Connected

Construction

  • Year Built

    Year Built: 2026

  • Home type

    Single Family Residence

  • Architectural Style

    Colonial, Modern

  • Foundation Details

    Concrete

  • Roof

    Metal

Utilities & Energy

  • Laundry Features

    Upper Level

  • Parking Features

    Attached Garage

  • Water Source

    Public Water Connected

  • Basement

    Full, Heated, Fully Finished, Cooled

  • Pool Features

    Gunite, Heated, In Ground Pool

Other Features

  • Subdivision Name

    Long Lots

  • Lot Features

    Fence Partial, Level Lot, On Cul De Sac, Professionally Landscaped

Price History

DateEventPrice

09/04/2026

Source: mls_logoSMART MLS-CT #24204809

Listed for Sale

$4,600,000 -4.07%

$562/sqft

08/13/2026

Source: mls_logoSMART MLS-CT #24182984

Listing Removed

$4,795,000

$586/sqft

06/18/2026

Source: mls_logoSMART MLS-CT #24182984

Listed for Sale

$4,795,000

$586/sqft

06/10/2026

Source: #24182984

Coming Soon

$4,795,000 -5.98%

$586/sqft

07/03/2025

Source: mls_logoSMART MLS-CT #24065416

Listing Removed

$5,100,000

$623/sqft

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 31, 2026, 02:00PM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

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