Westport, CT / 14 DAYS ON MARKET

2 Windy Hill RoadWestport, CT 06880

Asking price$4,600,000Active

Open house

  • Sunday, September 20, 20261:00 pm – 3:00 pm ET

Our Take

2 Windy Hill Road is a newly completed, six-bedroom Westport home on a landscaped acre. The interiors feature a two-story foyer, soaring ceilings, white oak flooring, natural stone finishes, and European windows and doors. The chef’s kitchen connects to gathering spaces, while the primary suite adds a fireplace, sitting area, balcony overlooking the pool, dressing room, and heated spa-like bath. A lower level includes a gym, bar, recreation space, and guest suite. Outside are a gunite pool, covered living area, granite patios, and flat lawn.

Estimated buyer rebate

Buy with Cress and Save $57,500 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 50% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24204809
Bedrooms
6
BathroomsBaths
6 full / 2 half
Square feet
8,185
Year built
2026
Acres
1
Property taxes
Not available

What stands out

  • Private landscaped acre
  • Two-story foyer with white oak flooring
  • Chef’s kitchen with marble finishes
  • Primary suite with pool-overlooking balcony
  • Lower-level gym, bar, and guest suite
  • Gunite pool with automatic cover
  • Covered outdoor living and granite patios
  • Flat lawn with stone walls and privacy plantings
Read the full listing 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.

Schools

Elementary
Long Lots
Middle
Bedford
High
Staples

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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2 Windy Hill Road, Westport, CT 06880

Price history

DateEventPrice
Originally listed$4,600,000

Intermediate price changes and previous listings may not be included.

Could this be your next home?

Let’s talk about the property—and what working with Cress could save you.

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*Estimate: $4,600,000 asking price × assumed 2.5% buyer-agent commission × 50% rebate = $57,500. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by Keller Williams Prestige Prop. · (203) 327-6700

Jacob Bivona

SmartMLS · Listing #24204809 · Active

Listing data checked: Sep 18, 2026, 7:02 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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