NOMADEReal Estate

$4,795,000

Active

2 Windy Hill Road

Westport, Connecticut, 06880 · Fairfield County

6

Beds

8

Baths

8,185

Sq Ft

2026

Built

MLS # 24182984

Price / Sq Ft

$586

Property Type

Single Family For Sale

Lot Size

1

Class

Property

About This Property

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.

Property Details

2 Windy Hill Road, Westport Connecticut 06880 — Single Family For Sale listed at $4,795,000.

At a Glance

6

Bedrooms

8

Bathrooms

8,185

Sq Ft

1

Lot Size

--

Garage

2026

Year Built

The Details

Property TypeSingle Family For Sale
NeighborhoodFairfield
Address2 Windy Hill Road
MLS Number24182984
Year Built2026
Square Footage8,185
Lot Size1
Bedrooms6
Bathrooms8
Water SourcePublic Water Connected

Property Details

Other Details

Appliances IncludedCook Top,Oven/Range,Microwave,Range Hood,Refrigerator,Subzero,Icemaker,Dishwasher,Washer,Dryer,Wine Chiller
Lockbox LocationFront Door
Parcel Number411794
Rooms AdditionalBonus Room,Foyer,Gym,Laundry Room
ZoningAA

Property Features

Attic DescriptionPull-Down Stairs
Attic YN1
Basement DescriptionFull,Heated,Fully Finished
Cooling SystemCentral Air,Zoned
Energy FeaturesHome Energy Rating,Generator Ready
Exterior FeaturesBalcony,Gutters,Lighting,French Doors,Underground Sprinkler,Patio
Exterior SidingVertical Siding,Wood
Fireplaces Total2
Foundation TypeConcrete
Garage ParkingAttached Garage
Garages Number3
Heat Fuel TypeNatural Gas
Heat TypeHot Air,Zoned
Home AutomationAppliances,Thermostat(s),Wired For Audio
Hot Water DescriptionNatural Gas,Tankless Hotwater
Interior FeaturesAudio System,Auto Garage Door Opener,Cable - Pre-wired,Humidifier,Open Floor Plan,Security System
Laundry Room InfoUpper Level
Pool DescriptionGunite,Heated,In Ground Pool
Roof InformationMetal
Swimming Pool YN1

Location & Community

DirectionsRoseville rd to Windy Hill rd
Elementary SchoolLong Lots
High SchoolStaples
Middle Jr High SchoolBedford
Nearby AmenitiesCommuter Bus,Golf Course,Health Club,Library,Playground/Tot Lot,Public Rec Facilities,Shopping/Mall
NeighborhoodLong Lots

All Photos (45)

MARKET CONTEXTWestport
Town Median+231% vs list
$1,450,000
Westport, CT
Mill Rate
16.86
Fairfield County
NYC Commute
60 min
Metro-North express
Schools
A+
3 graded
LOADING COMP CLOUD…

This listing is +231% vs the Westport median. Verify against same-school-district comps before competing offers.

Contact Jacob Bivona

Fill out the form below and we will respond promptly.

Affordability Calculator

$4,795,000

Down Payment$959,000
Loan Amount$3,836,000
Principal & Interest$24,246/mo
Property Tax$4,795/mo
Insurance$100/mo
Est. Monthly$29,141/mo

Listing Agent

J

Jacob Bivona

Keller Williams Prestige Prop.

Quick Facts

StatusActive
TypeSingle Family For Sale
ClassProperty
MLS #24182984
Last Updated2026-06-28