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2 Windy Hill Road, Westport, CT 06880

Single Family For Sale

$4,795,000
$586/sqft
2 Windy Hill Road, Westport, CT
Coming Soon Open House 6/18 · 11am–2pm
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6
Bedrooms
8
Bathrooms
8,185
Sq Ft
1
Acres
2026
Year Built

About This Home

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.

Listed by Jacob Bivona (203) 705-8180 with Keller Williams Prestige Prop. (203) 327-6700

Listing Snapshot

Price $4,795,000 Days on Our Site 0 days
Property Tax — Style Colonial,Modern
Year Built 2026 Total Sq Ft 8,185
Lot Size 1 acres HOA Fees N/A
Bedrooms 6 Full Bathrooms 6
Total Rooms 14 Half Baths 2

Key Features

Interior
  • Audio System
  • Auto Garage Door Opener
  • Cable - Pre-wired
  • Humidifier
  • Open Floor Plan
  • Security System
Appliances
  • Cook Top
  • Oven/Range
  • Microwave
  • Range Hood
  • Refrigerator
  • Subzero
  • Icemaker
  • Dishwasher
  • Washer
  • Dryer
  • Wine Chiller
Outdoor
  • Balcony
  • Gutters
  • Lighting
  • French Doors
  • Underground Sprinkler
  • Patio
  • Gunite
  • Heated
  • In Ground Pool
Nearby
  • Commuter Bus
  • Golf Course
  • Health Club
  • Library
  • Playground/Tot Lot
  • Public Rec Facilities
  • Shopping/Mall

Structure & Parking

Construction Frame
Roof Metal
Garage Spaces 3
Garage Type Attached Garage
Below Grade 2,360 sq ft

Systems & Utilities

Heat Hot Air, Zoned
Fuel Natural Gas
Cooling Central Air, Zoned
Hot Water Natural Gas, Tankless Hotwater
Water Public Water Connected
Sewer Public Sewer Connected

Schools

Elem Long Lots
Middle Bedford
High Staples

Mortgage Calculator

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Est. Monthly Payment —
Principal & Interest —
Est. Home Insurance —

Estimate only. Contact a lender for accurate figures.

Listing History

Date Event Price
Jun 10, 2026 Listed $4,795,000

Frequently Asked Questions

How much does 2 Windy Hill Road in Westport, CT cost?
This property is listed at $4,795,000, which works out to $586 per square foot.
How many bedrooms does 2 Windy Hill Road have?
This home has 6 bedrooms and 8 bathrooms.
What is the square footage of 2 Windy Hill Road?
The home is 8,185 square feet, situated on 1 acres.
When was 2 Windy Hill Road in Westport built?
This property was built in 2026.
Is 2 Windy Hill Road, Westport, CT still available?
The current MLS status of this property is "Coming Soon". Contact RYZE Realty Group for the latest availability.
What school district is 2 Windy Hill Road, Westport in?
This home is served by the Westport public school system, with Long Lots as the elementary school and Staples as the high school.
How do I schedule a tour of 2 Windy Hill Road, Westport, CT?
Contact RYZE Realty Group to schedule a private showing. You can submit a tour request directly on this page or call our office.

Listing Agent

Jacob Bivona · (203) 705-8180

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

MLS# 24182984 · Data provided by SmartMLS. Information deemed reliable but not guaranteed.
Listing updated Jun 17, 2026 3:38 AM UTC