2 Windy Hill Road
Westport, Connecticut 06880
- Beds
- 6
- Baths
- 6 | 2
- SqFt
- 8,185
- Acres
- 1.00
- Year Built
- 2026
- Neighborhood
- Long Lots
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
71
56 under contract
Median List Price
$4.60M
71 active listings
Median Closed Price
$2.42M
303 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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.
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.