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About This Home

This 6-bedroom, 8-bathroom single family at 2 Windy Hill Road in Westport, CT is listed for $4,795,000 ($586 per sqft). Built in 2026, the home offers 8,185 sqft of living space on a 1.00 acres lot.

Agent 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.

Key Features

  • Built in 2026
  • 1.00 acre lot
  • Fireplace

Property Details

6 full, 2 half
2026

Amenities

FireplaceA/C

Monthly Cost Estimate

$25,645/mo

20% down · 6.5% · 30 years

Principal$3,468
Interest$20,778
Insurance$1,399

Estimates only. Actual payments may vary.

Location

2 Windy Hill Road

Westport, CT 06880

Features & Amenities

Interior Features

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

Exterior Features

Balcony,Gutters,Lighting,French Doors,Underground Sprinkler,Patio

Property Details

Pool Features

Patio

Heating

Zoned

Cooling

ZonedCentral Air

Appliances

Cook TopOven/RangeMicrowaveRange HoodRefrigeratorSubzeroIcemakerDishwasherWasherDryerWine Chiller

Questions & Answers

This 6-bedroom, 8-bathroom single family at 2 Windy Hill Road is listed at $4,795,000 ($586/sqft). The estimated monthly payment is $20,778 based on 20% down at 6.5% interest.

Key features include: Built in 2026, 1.00 acre lot, Fireplace. Interior Features: Audio System,Auto Garage Door Opener,Cable - Pre-wired,Humidifier,Open Floor Plan,Security System. Exterior Features: Balcony,Gutters,Lighting,French Doors,Underground Sprinkler,Patio.

This property is listed by Jacob Bivona and can be reached at 2037058180 or jbivona.re@gmail.com.

JB

Jacob Bivona

Agent at Keller Williams Prestige Prop.

(203) 705-8180

Listed by Keller Williams Prestige Prop. · View on Broker Site

MLS# 24182984· Source: listhub· Updated 9 days ago

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

2 Windy Hill Road, Westport, CT 06880

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