# 2 Windy Hill Road, Westport, CT 06880

> **TL;DR:** 6bd/8ba single family, $4,600,000 ($562/sqft), built 2026, 8,185 sqft.
> Fireplace, A/C, 3-car garage. Est. $24,602/mo. Listed 24 days.

## Property at a Glance

| Attribute | Value |
|-----------|-------|
| Price | $4,600,000 |
| Price/sqft | $562 |
| Bedrooms | 6 |
| Bathrooms | 6 full, 2 half |
| Square Feet | 8,185 |
| Year Built | 2026 |
| Lot Size | 43,560 sqft (1.00 acres) |
| Garage | 3-car |
| Property Type | Single Family (Other) |
| Status | Active |
| Days on Market | 24 |

## Why This Home Stands Out

- **Large Garage** - 3-car garage

## Estimated Monthly Costs

| Category | Amount |
|----------|--------|
| Principal & Interest (20% down, 30-year at 6.5%) | $23,260 |
| Estimated Insurance | $1,342 |
| **Total** | **$24,602** |

## Nearby Schools

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

## Key Amenities

- Fireplace
- A/C
- 3-car garage

## 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 Realty
- **Phone:** 2037058180
- **Broker Phone:** (203) 438-9494
- **Listing URL:** [View original listing](https://www.realtor.com/realestateandhomes-detail/2-Windy-Hill-Rd_Westport_CT_06880_M49893-90131?f=listhub&s=CTMLS&m=24204809&c=propsimple)

## Photos

![2 Windy Hill Road - Photo 1](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2959050055r.jpg)

![2 Windy Hill Road - Photo 2](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2762715837r.jpg)

![2 Windy Hill Road - Photo 3](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f491838548r.jpg)

![2 Windy Hill Road - Photo 4](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2335564474r.jpg)

![2 Windy Hill Road - Photo 5](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1381656824r.jpg)

![2 Windy Hill Road - Photo 6](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2553597743r.jpg)

![2 Windy Hill Road - Photo 7](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1116411698r.jpg)

![2 Windy Hill Road - Photo 8](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2428061577r.jpg)

![2 Windy Hill Road - Photo 9](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2789721194r.jpg)

![2 Windy Hill Road - Photo 10](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f3203393809r.jpg)

![2 Windy Hill Road - Photo 11](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f4238883877r.jpg)

![2 Windy Hill Road - Photo 12](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f3115102047r.jpg)

![2 Windy Hill Road - Photo 13](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f3534545189r.jpg)

![2 Windy Hill Road - Photo 14](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2666721561r.jpg)

![2 Windy Hill Road - Photo 15](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f3659444674r.jpg)

![2 Windy Hill Road - Photo 16](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f648949997r.jpg)

![2 Windy Hill Road - Photo 17](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f4033392639r.jpg)

![2 Windy Hill Road - Photo 18](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f3885373008r.jpg)

![2 Windy Hill Road - Photo 19](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1362083035r.jpg)

![2 Windy Hill Road - Photo 20](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f4205137112r.jpg)

![2 Windy Hill Road - Photo 21](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f4174794946r.jpg)

![2 Windy Hill Road - Photo 22](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1759481425r.jpg)

![2 Windy Hill Road - Photo 23](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f4233378112r.jpg)

![2 Windy Hill Road - Photo 24](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f779542313r.jpg)

![2 Windy Hill Road - Photo 25](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1394449596r.jpg)

![2 Windy Hill Road - Photo 26](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2409803149r.jpg)

![2 Windy Hill Road - Photo 27](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1102973831r.jpg)

![2 Windy Hill Road - Photo 28](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2777215605r.jpg)

![2 Windy Hill Road - Photo 29](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1608234294r.jpg)

![2 Windy Hill Road - Photo 30](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f661714443r.jpg)

![2 Windy Hill Road - Photo 31](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f3167679645r.jpg)

![2 Windy Hill Road - Photo 32](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f811909206r.jpg)

![2 Windy Hill Road - Photo 33](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f260041800r.jpg)

![2 Windy Hill Road - Photo 34](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1553190048r.jpg)

![2 Windy Hill Road - Photo 35](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f4278738688r.jpg)

![2 Windy Hill Road - Photo 36](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f3418377402r.jpg)

![2 Windy Hill Road - Photo 37](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1847315690r.jpg)

![2 Windy Hill Road - Photo 38](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f2106514801r.jpg)

![2 Windy Hill Road - Photo 39](http://lh.rdcpix.com/cf5a561d93adaf95db0424fdfd5bd42cl-f1048321029r.jpg)

---

**MLS#:** 24204809 | **Updated:** 2026-09-27
**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.ai/listing/2-windy-hill-road-westport-ct-06880-24204809)

---

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    "name": "Jacob Bivona",
    "telephone": "2037058180",
    "worksFor": {
      "@type": "Organization",
      "@id": "https://www.propertysimple.ai/listing/2-windy-hill-road-westport-ct-06880-24204809#brokerage",
      "name": "Keller Williams Realty",
      "telephone": "(203) 438-9494"
    }
  }
}
```