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2 Windy Hill Road

Westport, Connecticut 06880

ACTIVE$4,795,000
Beds
6
Baths
6 | 2
SqFt
8,185
Acres
1.00
Year Built
2026
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
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Pool3-Car Garage2 FireplacesNew Construction

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.

Key Facts

City/Town
Westport
Neighborhood
Long Lots
Property / Style
Single Family · Colonial,Modern
Year Built
2026
Days on Market
46 days
Beds
6
Baths
6 full · 2 half
Living Area
8,185 sq ft
Lot Size
1.00 acres
Garage / Parking
3 garage
Property Taxes
Not on file from MLS

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

56

71 active listings

Median $ / Sq Ft

$820

71 active listings

Sale-to-List Ratio

100.0%

303 sales

How this home compares

List Price

$4.79M

vs $4.60M median

In line with median

Price / Sq Ft

$586

vs $820 median

28.5% below median

Days on Market

46 days

vs 56 days median

10 days fresher than median

Based on 71 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.

Location

2 Windy Hill Road, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$26,046

per month

  • Principal & Interest$24,448
  • Property Taxes$0
  • Insurance$1,598
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Westport
Neighborhood
Long Lots
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial,Modern
Year Built
2026
New Construction
Completed/Never Occupied
Living Area
8,185 sq ft
Below Grade
2,360 sq ft

Schools

Elementary
Long Lots
High
Staples

Interior

Heating
Hot AirZoned
Heat Fuel
Natural Gas
Cooling
Central AirZoned
Fireplaces
2
Laundry
Upper Level
Appliances
Cook TopOven/RangeMicrowaveRange HoodRefrigeratorSubzeroIcemakerDishwasherWasherDryerWine Chiller
Basement
FullHeatedFully Finished
Interior Features
Audio SystemAuto Garage Door OpenerCable - Pre-wiredHumidifierOpen Floor PlanSecurity System
Additional Rooms
Bonus RoomFoyerGymLaundry Room

Exterior & Lot

Lot Size
1.00 acres
Zoning
AA
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Pool
GuniteHeatedIn Ground Pool
Construction
Vertical SidingWood
Roof
Metal
Foundation
Concrete
Exterior Features
BalconyGuttersLightingFrench DoorsUnderground SprinklerPatio
Lot Description
Fence - PartialLevel LotOn Cul-De-SacProfessionally Landscaped

Listing & Financials

Days on Market
46
MLS #
24182984
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Jacob Bivona

(203) 705-8180

Keller Williams Prestige Prop.

(203) 327-6700

Co-Listed By

Wendy Ryan

Keller Williams Prestige Prop.

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/27/2026 at 10:01 AM UTC.