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$4,600,000

Listing Price

6beds

6baths

8,185sqft

43,560sqft lot

2 Windy Hill Rd, Westport, CT 06880

Member Features

Find Real Estate Bargain!

  • Full foreclosure details

  • Home value, equity and ownership info

  • Find homes priced below market

  • Get full access with a FREE Account

Already a member?

For Sale

Off Market

Single Family

Home type

562

Price / sqft

1963

Year built

Home Details

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.

Interior Details

Square Feet
  • 8185

Bedrooms
  • 6

Bathrooms
  • 6

Heating
  • Has Heating:

    Yes

  • Heating Type:

    Hot Water

Cooling
  • Has Cooling:

    Yes

  • Cooling Type:

    N/A

Fuel
  • Has Fuel:

    Yes

  • Fuel Type:

    Gas

Basement
  • Has Basement:

    No

  • Basement Type:

    Basement (unspecified)

Flooring
  • Has Flooring:

    No

  • Flooring Type:

    N/A

Fireplace
  • Has Fireplace:

    Yes

  • Fireplace Type:

    N/A

Property Details

Lot Size
  • 43560

Water
  • No

Sewer
  • No

Parking
  • Type:

    Garage, Basement

  • Location:

    N/A

  • Status:

    N/A

  • Number of Spaces:

    2

Deck
  • N/A

Patio
  • N/A

Fence
  • N/A

Pool
  • N/A

Porch
  • N/A

Stoop
  • N/A

Breezeway
  • N/A

Construction Details

Number of Stories
  • 1

Style
  • Raised Ranch

Exterior
  • Wood Siding

Foundation
  • N/A

Roof
  • Gable

Roofing Material
  • Asphalt

Tax History

Year

Amount

Land

Improvement

Percent Change

Assessment

2020

$9,555

$384,400

$187,400

--%

$571,800

2019

$9,641

$384,400

$187,400

--%

$571,800

2018

$9,641

$384,400

$187,400

--%

$571,800

2017

$9,641

$384,400

$187,400

--%

$571,800

2016

$9,641

$384,400

$187,400

--%

$571,800

2014

$9,171

$317,600

$193,600

--%

$511,200

2011

$9,237

$317,600

$193,600

--%

$511,200

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Average Home Price in 06880

Nearby Properties

Zip Code

Price

Bed

Bath

Sqft

Lot

Sold Date

$6,148,640

7 Beds

9 Baths

8,273 Sqft

43,560 Lot (sqft)

Sold 10/18/2026

$4,600,000

6 Beds

6 Baths

8,185 Sqft

43,560 Lot (sqft)

Sold 10/13/2026

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Calculators

Mortgage

Mortgage Calculator

Calculate your monthly mortgage payments.
Household Income
70,000
$
Home price
4,600,000
$
Down payment
920,000
$
Mortgage Rate
6.5
%
Loan Term
Property Tax Rate
1.1
%
Homeowner's Insurance (Annual)
27,600
$
HOA (Monthly)
0
$
PMI
0
$
$29,777
Your Payment
Total Monthly Payment:$29,777
Percent of Income:510%
Affordable:No

Details for 2 WINDY HILL RD

Property Debt

Foreclosure Contact Details

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