2 Windy Hill Road

Westport, CT 06880 Directions
$4,795,000
  • 6Bed
  • 6/2Baths
  • 8,185Sqft
  • 1Acres
  • 2026Built
  • Long LotsElementary

Property Highlights

  • Jr. High School: Bedford
  • High School: Staples
  • Neighborhood: Long Lots
  • Price/Sqft: $586
  • Days on Market: 3
  • MLS: 24182984

Property Highlights

  • Jr. High School: Bedford
  • High School: Staples
  • Neighborhood: Long Lots
  • Price/Sqft: $586
  • Days on Market: 3
  • MLS: 24182984

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...

Property Highlights

  • Jr. High School: Bedford
  • High School: Staples
  • Neighborhood: Long Lots
  • Price/Sqft: $586
  • Days on Market: 3
  • MLS: 24182984

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.

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.

Read MoreRead Less
  • Additional Information
    • Attic Description: Pull-Down Stairs
    • Average Days On Market: 3
    • Basement Description: Full, Heated, Fully Finished
    • Days On Market: 3
    • Elementary School: Long Lots
    • Garage: Attached Garage
    • Garage Count: 3
    • Has Pool?: Yes
    • High School: Staples
    • Is Occupied?: Vacant
    • Junior High School: Bedford
    • Living Area SqFt: 8,185
    • Neighborhood: Long Lots
    • Sewer: Public Sewer Connected
    • Style: Colonial, Modern
    • Tax Year: July 2025-June 2026
    • Type: Single Family For Sale
    • Year Built: 2026
    • Year Built Details: Owner
    • Zoning: AA
  • Amenities
    • Golf Course
    • Health Club
    • Library
    • Playground/Tot Lot
    • Public Rec Facilities
    • Shopping/Mall
    • Audio System
    • Auto Garage Door Opener
    • Cable - Pre-wired
    • Humidifier
    • Open Floor Plan
    • Security System
  • Interior/Exterior Features
    • Air Conditioning: Central Air, Zoned
    • Appliances Included: Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
    • Attic: Yes
    • Beds: 6
    • Cooling: Central Air, Zoned
    • Exterior Features: Balcony,Gutters,Lighting,French Doors,Underground Sprinkler,Patio
    • Exterior Siding: Vertical Siding, Wood
    • Fireplaces: 2
    • Full Baths: 6
    • Furnace Type: Natural Gas
    • Half Baths: 2
    • Heat: Natural Gas
    • Heat Fuel: Natural Gas
    • Hot Water: Natural Gas, Tankless Hotwater
    • Laundry Room: Upper Level
    • Pool Description: Gunite, Heated, In Ground Pool
    • Roof: Metal
    • Rooms: 14
William Pitt / Julia B. Fee Sotheby's International Realty

Westport Brokerage

199 Post Road East
Westport, CT 06880

Listing Courtesy of Jacob Bivona of Keller Williams Prestige Prop.

Click to view full screen