# 2 Windy Hill Road, Westport, CT 06880

> **TL;DR:** 6bd/8ba single family, $4,795,000 ($586/sqft), built 2026, 8,185 sqft.
> Fireplace, A/C. Est. $20,778/mo. Listed 9 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $4,795,000 |
| Price/sqft | $586 |
| Bedrooms | 6 |
| Bathrooms | 6 full, 2 half |
| Square Feet | 8,185 |
| Year Built | 2026 |
| Lot Size | 43,560 sqft (1.00 acres) |
| Property Type | Single Family (Other) |
| Status | For Sale |
| Days on Market | 9 |

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Mortgage (20% down, 6.5%) | $20,778 |
| **Total** | **$20,778** |

## Nearby Schools

- **Elementary:** Long Lots
- **High:** Staples

## Key Amenities

- Fireplace
- A/C

## Property Highlights

- Built in 2026
- 1.00 acre lot
- Fireplace

## Description

### 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.

## Location

- **Address:** 2 Windy Hill Road, Westport, CT 06880
- **County:** Fairfield
- **Coordinates:** 41.144377, -73.339806
- **Google Maps:** https://www.google.com/maps?q=41.144377,-73.339806

## Listing Agent

- **Name:** Jacob Bivona
- **Brokerage:** Keller Williams Prestige Prop.
- **Phone:** 2037058180
- **Email:** jbivona.re@gmail.com

## Primary Photo

![2 Windy Hill Road - Primary Photo](http://lh.rdcpix.com/36b9ec63b653f1901b0e3c1074cf59d0l-f2959050055r.jpg)

*7 total photos available on [listing page](https://www.propertysimple.com/listing/2-windy-hill-road-westport-ct-06880-24182984)*

---

**MLS#:** 24182984 | **Updated:** 2026-06-24
**Source:** listhub

*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.*

[View on PropertySimple](https://www.propertysimple.com/listing/2-windy-hill-road-westport-ct-06880-24182984)

---

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