2 Windy Hill Rd

Westport, CT 06880

$4,795,000
Price
6
Beds
8,185 Sq. Ft.
$586 / Sq. Ft.
8,185
Sq. Ft.
$586
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Coming Soon
Coming Soon

Description

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...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.
  1. Listed by Jacob Bivona • Keller Williams Prestige Prop.
    P: (203)-705-8180 C: (203)-705-8180 jbivona.re@gmail.com
  2. Listed by Wendy Ryan • Brown Harris Stevens
    P: (203)-254-1500 C: (203)-964-7450 wryan@bhsusa.com

Property Details for 2 Windy Hill Road

Basement Description
Full, Heated, Fully Finished
Direct Waterfront
No
Expected Active Date
06-18-2026
Garages Number
3
Neighborhood
Long Lots
Style
Colonial, Modern
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 06/10/2026 09:44 PM

Property Details for 2 Windy Hill Road

StatusComing Soon
MLS #24182984
Days on Market-
Taxes-
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built2026
Lot Size1.00 AC / 43,560 SF
CountyFairfield County
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Location

Listing Courtesy of Keller Williams Prestige Prop., Jacob Bivona; Brown Harris Stevens, Wendy Ryan
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Building Information for 2 Windy Hill Road

Stories-Year Built2026Building Size-Lot Size1.00 AC / 43,560 SF

Payment Calculator

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$24,810 per month

30 year fixed, 6.36% Interest

Principal and Interest

$23,894

Property Taxes

$916

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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Property Information for 2 Windy Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Roseville rd to Windy Hill rd
  • Elementary School: Long Lots
  • High School: Staples
  • Latitude: 41.144214
  • Longitude: -73.339736
  • Middle Jr High School: Bedford
  • Neighborhood Amenities: Commuter Bus, Golf Course, Health Club, Library, Playground/Tot Lot, Public Rec Facilities, Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $0
Interior and Exterior Features
Exterior Features
  • Exterior Features: Balcony, Gutters, Lighting, French Doors, Underground Sprinkler, Patio
  • Pool Description: Gunite, Heated, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Pull-Down Stairs
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air, Zoned
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Home Automation: Appliances, Thermostat(s), Wired For Audio
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Humidifier, Open Floor Plan, Security System
  • Laundry Room Info: Upper Level
  • Rooms Additional: Bonus Room, Foyer, Gym, Laundry Room
  • Rooms Total: 14
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Built-Ins,Fireplace,Patio/Terrace,Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 2
  • Room Entry Order: 10
  • Room Features: Jack & Jill Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 11
  • Room Features: 9 ft+ Ceilings,Entertainment Center
  • Room Level: Lower
  • Room Type: Media Room
Room 4
  • Room Entry Order: 12
  • Room Features: 9 ft+ Ceilings
  • Room Level: Lower
  • Room Type: Rec/Play Room
Room 5
  • Listing Key: 53EC81835DBA5D10E063E201100A0BAD
  • Room Entry Order: 13
  • Room Features: 9 ft+ Ceilings,Walk-In Closet
  • Room Level: Lower
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 14
  • Room Level: Lower
  • Room Type: Full Bath
Room 7
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Built-Ins,Quartz Counters,Dry Bar,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 8
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Quartz Counters,Dining Area,Wet Bar,Island,Pantry
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 9
  • Listing Key: 53EC81835DBA5D10E063E201100A0BAD
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 10
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Level: Main
  • Room Type: Office
Room 11
  • Room Entry Order: 6
  • Room Features: Cathedral Ceiling,Balcony/Deck,Beams,Fireplace,Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 12
  • Room Entry Order: 7
  • Room Features: Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 13
  • Room Entry Order: 8
  • Room Features: Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 14
  • Room Entry Order: 9
  • Room Features: Jack & Jill Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vertical Siding, Wood
  • Foundation Type: Concrete
  • New Construction Type: Completed/Never Occupied
  • Roof: Metal
  • Year Built: 2026
  • Year Built Source: Owner
  • Bank Owned Property: No
  • Sq Ft Description: New Construction
  • Sq Ft Est Heated Below Grade: 2360
Lot Information
  • Lot Description: Fence - Partial, Level Lot, On Cul-De-Sac, Professionally Landscaped
  • Parcel Number: 411794
  • Sq Ft Est Heated Above Grade: 5825.0
  • Sq Ft Total: 8185.0
  • Zoning: AA
Utilities
  • Energy Features: Home Energy Rating, Generator Ready
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Natural Gas, Tankless Hotwater
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Vacant

Property History for 2 Windy Hill Road

DateEvent & SourcePriceAppreciation
Sep 16, 2024

Closed (Public Record)

Public Record #1541223656

$1,100,000

+2.3% / yr

Jul 13, 2007

Closed (Public Record)

Public Record #724131892

$750,000—
Jul 13, 2007

Closed (Public Record)

Public Record #224131892

$750,000—
DateEvent & SourcePrice
09/16/2024

Closed (Public Record)

Public Record #1541223656

$1,100,000

+2.3% / yr

07/13/2007

Closed (Public Record)

Public Record #724131892

$750,000
07/13/2007

Closed (Public Record)

Public Record #224131892

$750,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 2 Windy Hill Road

Taxable ValueLand$419,000Additions$163,900Total$582,900
Tax Record2024$10,993 ($916 / month)
Home Facts
Beds4Baths3Total Finished SqFt2,144 SqFtAbove Grade Finished SqFt2,144 SqFtStories1Lot Size43,560 SqFtStyleSingle Family ResidenceYear Built1963ZoningAACountyWESTERN CONNECTICUTAPNWPRT M:E10 L:070-000Fireplace TypeHas Fireplace

Schools near 2 Windy Hill Road

This home is within Westport School District.
Rating
School
Type
Grades
Distance
Long Lots School
Public - K to 5
Bedford Middle School
Public - 6 to 8
Staples High School
Public - 9 to 12
Green's Farms Segregated
Public - 1 to 5
Rating
School
Distance
Long Lots School
PublicK to 5

Bedford Middle School
Public6 to 8

Staples High School
Public9 to 12

Green's Farms Segregated
Public1 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 2 Windy Hill Road, Westport, CT 06880

2 Windy Hill Road is a single family home Coming Soon in Westport, CT 06880. This property is currently priced at $4,795,000. This listing's school district is Westport School District. Nearby schools include Long Lots School, Bedford Middle School and Staples High School. 2 Windy Hill Road is a 6-bed, 8-bath, 8,185 sqft single family home built in 2026.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of any information, descriptions or measurements (including square footage measurements and property condition), such should be independently verified through appropriate means, including, but not limited to, in person inspection and public records, and Compass International Holdings, its subsidiaries, affiliates and independently owned and operated franchisees, and their affiliated agents and associated third parties expressly disclaim any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the seller's discretion. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Keller Williams Prestige Prop., Jacob Bivona; Brown Harris Stevens, Wendy Ryan

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.