2 Windy Hill Rd Westport, CT, 06880

single family home
$ 4,795,000 For Sale Coming Soon Jun 10, 2026
  • 6 beds
  • 8 baths
  • 8,185 sq ft
  • 1 acre
  • new construction
  • in ground pool
  • 3 cars garage

About the 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.

Rooms & Interior

6 bedrooms beds
6 full + 2 half baths
8,185 square feet sq ft

Room Details

  • Dining Room (Main Level) 9 ft+ Ceilings, Built-Ins, Quartz Counters, Dry Bar, Hardwood Floor
  • Bedroom (Upper Level) Full Bath, Walk-In Closet
  • Bedroom (Upper Level) Jack & Jill Bath, Walk-In Closet
  • Full Bath (Lower Level)
  • Living Room (Main Level) 9 ft+ Ceilings, Hardwood Floor
  • Media Room (Lower Level) 9 ft+ Ceilings, Entertainment Center
  • Rec/Play Room (Lower Level) 9 ft+ Ceilings
  • Office (Main Level) 9 ft+ Ceilings, Hardwood Floor
  • Family Room (Main Level) 9 ft+ Ceilings, Built-Ins, Fireplace, Patio/Terrace, Sliders, Hardwood Floor
  • Eat In Kitchen (Main Level) 9 ft+ Ceilings, Quartz Counters, Dining Area, Wet Bar, Island, Pantry
  • Primary Br Suite (Upper Level) Cathedral Ceiling, Balcony/Deck, Beams, Fireplace, Full Bath, Walk-In Closet
  • Bedroom (Upper Level) Full Bath, Walk-In Closet
  • Bedroom (Upper Level) Jack & Jill Bath, Walk-In Closet
  • Bedroom (Lower Level) 9 ft+ Ceilings, Walk-In Closet
  • Other Rooms Bonus room, Foyer, Gym, Laundry room

Home Features

Heating

  • Fireplaces: 2
  • Heating: hot air, zoned
  • Heat fuel type: natural gas

Cooling

  • Central air
  • Zoned

Interior Features

  • 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

Home Automation

  • Appliances
  • Thermostat(s)
  • Wired for audio

Attic

  • Pull-down stairs

Basement

  • Full
  • Heated
  • Fully finished

Laundry

  • Upper level

Energy Features

  • Home energy rating
  • Generator ready

Exterior Features

  • Balcony
  • Gutters
  • Lighting
  • French doors
  • Underground sprinkler
  • Patio

Property Details

Parking

  • Garage spaces: 3
  • Attached garage

Swimming Pool

  • Gunite
  • Heated
  • In ground pool

Lot Details

  • Lot surface: 1 acres
  • Fence - partial
  • Level lot
  • On cul-de-sac
  • Professionally landscaped

Utilities

  • Water: public water connected
  • Sewage: pub. sewer connected

Near-by Amenities

  • Commuter bus
  • Golf course
  • Health club
  • Library
  • Playground/tot lot
  • Private rec facilities
  • Shopping/mall

Construction Details

Style
colonial, modern

New construction
completed/never occupied

Construction year
2026

Exterior Siding
vertical siding, wood

Foundation
concrete

Roof
metal

New Constructions in Westport

Area & Town

This home is located in Roseville/North Avenue neighborhood, in the town of Westport.

Finance & Listing Info

Status Coming soon
Listing date June 10, 2026
List price $ 4,795,000
Current price $ 4,795,000
Tax amount $ 0
Tax year july 2025-june 2026
MLS ID #24182984
List Agent Jacob Bivona
Co-List Agent Wendy Ryan
List Office Keller Williams Prestige Prop.
Co-List Office brown harris stevens

2 Windy Hill Road Home Photos

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