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$4,795,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 6 Beds
  • 6 Full Baths
  • 2 Partial Baths
  • 8,185 Sq. Ft.
  • 3 Car Garage
  • Updated 9 hours ago
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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.

Full Property Details for 2 Windy Hill Rd

General

  • Price: $4,795,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24182984
  • Updated: Today (6/18/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 14
  • Rooms/Areas: Bonus Room, Foyer, Gym, Laundry Room
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Humidifier, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 8
  • Full Bathrooms: 6
  • Half Bathrooms: 2
  • Full Bath: Lower

Bedrooms

  • Total Bedrooms: 6
  • Primary Suite: Cathedral Ceiling, Balcony/Deck, Beams, Fireplace, Ful, Upper
  • Bedroom 1: Bedroom - 9 ft+ Ceilings, Walk-In Closet, Lower
  • Bedroom 2: Bedroom - Full Bath, Walk-In Closet, Upper
  • Bedroom 3: Bedroom - Jack & Jill Bath, Walk-In Closet, Upper
  • Bedroom 4: Bedroom - Full Bath, Walk-In Closet, Upper
  • Bedroom 5: Bedroom - Jack & Jill Bath, Walk-In Closet, Upper

Other Rooms

  • Living Room: Living Room - 9 ft+ Ceilings, Hardwood Floor, Main
  • Family Room: Family Room - 9 ft+ Ceilings, Built-Ins, Fireplace, Patio/Terrace, Sliders, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - 9 ft+ Ceilings, Quartz Counters, Dining Area, Wet Bar, Island, , Main
  • Dining Room: Dining Room - 9 ft+ Ceilings, Built-Ins, Quartz Counters, Dry Bar, Hardwood Floor, Main
  • Office: Office - 9 ft+ Ceilings, Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - 9 ft+ Ceilings, Lower
  • Rec Room: 9 ft+ Ceilings, Lower
  • Theater/Media: Media Room - 9 ft+ Ceilings, Entertainment Center, Lower
  • Laundry: Upper Level

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, In Ground Pool

Exterior

  • Exterior Features: Balcony, Gutters, Lighting, French Doors, Underground Sprinkler, Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Long Lots
  • Driving Directions: Roseville rd to Windy Hill rd

School Information

  • Elementary School: Long Lots
  • Middle School: Bedford
  • High School: Staples

Community

  • Community Name: Long Lots

Heating & Cooling

  • Cooling Type: Central Air, Zoned
  • Heating Type: Hot Air, Zoned, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Natural Gas, Tankless Hotwater

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial, Modern
  • Construction Status: Completed/Never Occupied
  • Exterior Const.: Vertical Siding, Wood
  • Basement Desc.: Full, Heated, Fully Finished
  • Roof: Metal
  • Attic: Yes
  • Square Feet: 8,185
  • Above Ground: 5,825 Sq. Ft.
  • Below Ground: 2,360 Sq. Ft.
  • Year Built: 2026

Lot Features

  • Lot Size (Acres): 1
  • Zoning: AA
  • Lot Description: Fence - Partial, Level Lot, On Cul-De-Sac, Professionally Landscaped

Green Features

  • Energy Features: Home Energy Rating, Generator Ready

Financial Considerations

  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Property ID: 411794

Listed by Keller Williams Prestige Prop., Jacob Bivona and Brown Harris Stevens, Wendy Ryan

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Listing agents

— 2 Windy Hill Rd —

  • Jacob Bivona

    Keller Williams Prestige Prop.

  • Wendy Ryan

    Brown Harris Stevens

Agent Contact: (203) 705-8180 Office Contact: (203) 327-6700

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 2 Windy Hill Rd

School District:Westport School District
NameGradesDistance
Long Lots School
13 Hyde Lane, Westport, CT 06880
K-51.2 mi
Bedford Middle School
88 North Avenue, Westport, CT 06880
6-81.1 mi
Staples High School
70 North Avenue, Westport, CT 06880
9-120.9 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 2 Windy Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
6/18/2026
Listed
$4,795,000
335.91%
MLS
9/16/2024
Sold
$1,100,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 2 Windy Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$10,993
1%
$582,900
—
2023
$10,854
1%
$582,900
—
2023
$10,696
2%
$582,900
—
2022
$10,533
—
$582,900
—
2021
$10,533
10%
$582,900
2%
2020
$9,555
-1%
$571,800
—
2019
$9,641
—
$571,800
—
2018
$9,641
—
$571,800
—
2017
$9,641
—
$571,800
—
2016
$9,641
4%
$571,800
12%
2015
$9,248
1%
$511,200
—
2014
$9,171
-1%
$511,200
—
2011
$9,237
—
$511,200
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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*These costs are estimates, and the interest rates assume exceptional credit standing.

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with our affiliated lender
NMLS#: 1598647

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Listed by Keller Williams Prestige Prop., Jacob Bivona and Brown Harris Stevens, Wendy Ryan

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2 Windy Hill Road, Westport, CT 06880 (MLS# 24182984) is a Single Family property with 6 bedrooms, 6 full bathrooms and 2 partial bathrooms. 2 Windy Hill Road is currently listed for $4,795,000 and was received on June 18, 2026. Want to learn more about 2 Windy Hill Road? Do you have questions about finding other Single Family real estate for sale in Westport? You can browse all Westport real estate or contact a Coldwell Banker agent to request more information.

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