Off market dec 2024 for $4.2M

$4,445,486

Est. refi paymentEst. refi $15,214/mo

•

7,908

sq ft

5 Windy Hill Rd, Westport, CT 06880

About this home

Pristine and stately 8000 s.f. classic on highly-desirable, central cul de sac, in the heart of Westport, with picturesque, private yard, stunning pool and outdoor amenities. So many recent improvements inside and out, including new cedar roof & top of the line mechanical systems. Four luxurious levels of living -- main floor's lovely formal rooms have an open flow, and include spacious formal dining room & formal living room w/fireplace, large coffered family room, paneled library, sleek white gourmet kitchen/breakfast room w/Viking range, butlers pantry, expansive four-season porch & large mudroom leading to 3-car garage. Professionally-landscaped property with pergola-covered stone patio & outdoor kitchen, fabulous pool & extensive hardscape, w/lush gardens and charming wooded footpath. The upper level features an opulent primary suite w/gleaming spa bath, fireplace, separate sitting room & dressing room, the secondary bedrooms w/en suite updated baths & Jack/Jill, and finished third floor bonus space. The bright, newly-carpeted walkout lower level has large au pair, full bath and large gym. Sewer, city water and city gas offer convenient, easy living. Full-house oversized generator & int/ext audio too. This home has it all, and is located in one of the truly quiet, and most sought after close-to-town locations -- just moments to beach, schools, parks, downtown shopping/dining & Metro North.

Single-familyProperty Type

2007Year Built

1.01 acresLot Size

$562Est. Price/Sq.Ft.

3 car garageParking

Listed by Joni Usdan • Coldwell Banker Realty

Bought with Suzette Kraus • Compass Connecticut, LLC

Source:Smart MLS #24046072

Redfin Estimate

$4,445,486

$245K since sold in December 2024$51K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11% higher than the average sale price ($4.00M) of 6 comparable homes.

SOLD JUL 30, 2026
$3,225,000
A
5 beds6 baths6,302 sq ft
72 Compo Rd N, Westport, CT 06880
SOLD AUG 7, 2026
$5,700,000
B
6 beds6 baths8,717 sq ft
6 Twin Circle Dr, Westport, CT 06880
SOLD AUG 14, 2026
$4,400,000
C
6 beds5.5 baths6,775 sq ft
48 Bayberry Ln, Westport, CT 06880
SOLD JUN 30, 2026
$3,499,999
D
6 beds5.5 baths6,010 sq ft
13 Terhune Dr, Westport, CT 06880
SOLD AUG 21, 2026
$2,700,000
E
5 beds5 baths5,739 sq ft
2 Ledgemoor Ln, Westport, CT 06880
SOLD JUL 5, 2026
$4,500,000
F
5 beds7 baths8,364 sq ft
4 Peach Lot Pl Lot PL, Westport, CT 06880

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Earn from this home

Sell

$946,230

Est. take-home

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Refinance

Est. cash available

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Rent

$4,596/mo

Redfin rental estimate

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Market trends in 06880, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

104.3%

0.3% MoM

Median sale price

$2.4M

$38K MoM

Avg. days on market

32d

1 days MoM

Recently sold homes

104

21 MoM

New listings for sale

OPEN TODAY, 12PM TO 2PM
$1,599,000
5 beds4 baths3,519 sq ft
23 Meeker Rd, Westport, CT 06880
OPEN TODAY, 12PM TO 3PM
$1,799,000
4 beds3 baths2,725 sq ft
4 Bruce Ln, Westport, CT 06880
OPEN TODAY, 12PM TO 2PM
$2,500,000
4 beds4.5 baths4,096 sq ft
6 Sherwood Farms Ln, Westport, CT 06880
$1,095,000
1 bed1 bath820 sq ft
4 Morningside Dr N #102, Westport, CT 06880
$1,895,000
2 beds2.5 baths1,660 sq ft
4 Morningside. Dr N #202, Westport, CT 06880
$1,895,000
2 beds2.5 baths1,660 sq ft
4 Morningside Dr N #401, Westport, CT 06880
$1,395,000
2 beds2 baths955 sq ft
4 Morningside Dr N #301, Westport, CT 06880
OPEN TODAY, 1PM TO 3PM
$3,395,000
5 beds6.5 baths4,854 sq ft
12 Bauer Pl, Westport, CT 06880
$630,000
2 beds2.5 baths1,440 sq ft
25 Strathmore Ln #25, Westport, CT 06880
OPEN TODAY, 1PM TO 3PM
$4,595,000
6 beds7 baths7,132 sq ft
34 High Point Rd, Westport, CT 06880
See all

Provided by Redfin

Sale history for 5 Windy Hill Rd

Date

Event

Price

Smart MLS #24046072

Dec 3, 2024

Sold

$4,200,000

$531/sq ft

Oct 28, 2024

Contingent

—

Oct 14, 2024

Listed

$3,999,000

$506/sq ft

Public Records

Aug 22, 2012

Sold

$2,300,000

$291/sq ft

Smart MLS #98543501

Jun 19, 2012

Listed

$2,399,000

$303/sq ft

Smart MLS #98528271

Jun 19, 2012

Listing Removed

—

Feb 16, 2012

Listed

$2,489,000

$315/sq ft

Smart MLS #98503261

Feb 15, 2012

Listing Removed

—

May 31, 2011

Listed

$2,599,000

$329/sq ft

Smart MLS #98321379

Feb 28, 2007

Listed

$2,798,900

$354/sq ft

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Year

Property tax

Land + Additions

Assessment*

2023

$29,268 (+1.5%)

$441,100 + $1,153,900

$1,595,000

2022

$28,822 (+1.5%)

$441,100 + $1,153,900

$1,595,000

2021

$28,397 (+2.2%)

$441,100 + $1,130,400

$1,571,500

2020

$27,777 (−0.9%)

$452,300 + $1,210,000

$1,662,300

2019

$28,026

$452,300 + $1,210,000

$1,662,300

2018

$28,026

$452,300 + $1,210,000

$1,662,300

2017

$28,026 (+1.8%)

$452,300 + $1,210,000

$1,662,300

2016

$27,539 (−5.4%)

$452,300 + $1,181,100

$1,633,400

2014

$29,118

$373,900 + $1,249,200

$1,623,100

Tax history for 5 Windy Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$29,268 (+1.5%)

$441,100 + $1,153,900

$1,595,000

2022

$28,822 (+1.5%)

$441,100 + $1,153,900

$1,595,000

2021

$28,397 (+2.2%)

$441,100 + $1,130,400

$1,571,500

2020

$27,777 (−0.9%)

$452,300 + $1,210,000

$1,662,300

2019

$28,026

$452,300 + $1,210,000

$1,662,300

2018

$28,026

$452,300 + $1,210,000

$1,662,300

2017

$28,026 (+1.8%)

$452,300 + $1,210,000

$1,662,300

2016

$27,539 (−5.4%)

$452,300 + $1,181,100

$1,633,400

2014

$29,118

$373,900 + $1,249,200

$1,623,100

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

1.01 Acres

Year renovated

—

Sq. Ft.

6,308

Year built

2007

Style

Single Family Residential

County

Fairfield County

APN

413391

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

Nov 4, 2024 • Final

Residential fuel tank

Pump out and dispose of liquid from above ground fuel storage tanks. Cut, clean, and dispose of the tank systems in compliance with all local, state, and federal regulations.

Demolition

Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Paved, Driveway
Garages Number: 3

Parking Information
Parking Total Spaces: 3

Interior

Interior Information
Total Rooms: 13
Laundry Room Location: 2nd level
Laundry Room Info: Upper Level
Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Central Vacuum, Open Floor Plan, Security System
In-Law Apartment: Possible
In-Law Access: Lower Level
Fireplaces Total: 3
Cooling System: Central Air, Zoned
Appliances Included: Oven/Range, Microwave, Range Hood, Subzero, Dishwasher, Disposal, Washer, Electric Dryer, Wine Chiller

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 2

Bedroom Information
Beds Total: 6

Room Information
Rooms Additional: Foyer, Laundry Room, Sitting Room
Basement Description: Full, Heated, Sump Pump, Cooled, Partially Finished, Liveable Space, Full With Walk-Out
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Clapboard
Exterior Features: Porch-Heated, Grill, Terrace, Porch, Lighting, Stone Wall, Underground Sprinkler, Patio

Lot Information
Lot Description: Fence - Wood, Fence - Partial, Secluded, Lightly Wooded, On Cul-De-Sac, Professionally Landscaped, Rolling

Pool Information
Swimming Pool
Pool Description: Gunite, Heated, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Frame
Color: white

Property Information
Waterfront Description: Beach Rights, Water Community
Radon Mitigation Air
Property Type: Single Family For Sale
Driveway Type: Private

Financial

Assessments Information
Assessed Value: $1,595,000

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Domestic
Heat Type: Hot Air, Zoned
Heat Fuel Type: Natural Gas
Energy Features: Extra Insulation, Generator

Location

School Information
Middle Jr High School: Bedford
High School: Staples
Elementary School: Long Lots

Location Information
State: Connecticut
Nearby Amenities: Commuter Bus, Golf Course, Library, Paddle Tennis, Playground/Tot Lot, Public Rec Facilities, Putting Green, Tennis Courts
Directions: Post Road to Roseville Road to Windy Hill Road.
County: Fairfield

Public facts

Beds: 6
Baths: 6.0
Sq. Ft.: 6,308
Stories: 3.0
Lot Size: 1.01 acres
Style: Single Family Residential
Year Built: 2007
Year Renovated: —
County: Fairfield County
APN: 413391

Home facts updated by county records on Jul 12, 2023

Other

Documents & Disclosures
Supplement Count Public: 3

Around this home

Schools

K - 12
Preschool & daycare

Long Lots School

Public K-5 • Assigned • 1.2mi

9/10

Bedford Middle School

Public 6-8 • Assigned • 1.2mi

10/10

Staples High School

Public 9-12 • Assigned • 1.0mi

10/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

5/10 Heat Factor

7 days above 98° expected this year, 14 days in 30 years

6/10 Wind Factor

66% chance of strong winds in next 30 years

8/10 Air Factor

13 unhealthy days expected this year, 18 days in 30 years

Provided by First Street

Historical weather

Westport, CT • 06880

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.8 hours in June and 4.4 hours in December, placing it below the U.S. average for solar exposure.

8.8 hrs

4.4 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.22M – $5.11M

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New listings for sale in 06880

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$1,599,000

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23 Meeker Rd, Westport, CT 06880

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OPEN TODAY, 12PM TO 3PM

$1,799,000

4 beds3 baths2,725 sq ft

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OPEN TODAY, 12PM TO 2PM

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4 Morningside Dr N #102, Westport, CT 06880

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$1,895,000

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4 Morningside. Dr N #202, Westport, CT 06880

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4 Morningside Dr N #401, Westport, CT 06880

High end appliances • Private patio • Convenient locations

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4 Morningside Dr N #301, Westport, CT 06880

Private patio • In unit laundry • High end appliances

OPEN TODAY, 1PM TO 3PM

$3,395,000

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12 Bauer Pl, Westport, CT 06880

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25 Strathmore Ln #25, Westport, CT 06880

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Home values near 5 Windy Hill Rd

Data from public records.

Address	Redfin Estimate
12 Windy Hill Road, Westport, CT 5 Beds \| 3.5 Baths \| 5014 Sq. Ft.	$1,990,082
10 Windy Hill Road, Westport, CT 6 Beds \| 8 Baths \| 5654 Sq. Ft.	$2,442,019
3 Windy Hill Road, Westport, CT 4 Beds \| 3 Baths \| 2638 Sq. Ft.	$2,105,534
4 Windy Hill Road, Westport, CT 4 Beds \| 3 Baths \| 2552 Sq. Ft.	$2,108,324
84 Roseville Road, Westport, CT 5 Beds \| 6.5 Baths \| 5019 Sq. Ft.	$3,229,725
7 Rocky Acres Lane, Westport, CT 6 Beds \| 6 Baths \| 7304 Sq. Ft.	$4,355,806
6 Marc Lane, Westport, CT 3 Beds \| 3 Baths \| 3191 Sq. Ft.	$2,186,374

Address	Redfin Estimate
9 Windy Hill Road, Westport, CT 5 Beds \| 5 Baths \| 6560 Sq. Ft.	$3,807,744
7 Windy Hill Road, Westport, CT 4 Beds \| 6 Baths \| 5752 Sq. Ft.	$2,411,061
1 Windy Hill Road, Westport, CT 6 Beds \| 6 Baths \| 7053 Sq. Ft.	$3,766,135
6 Windy Hill Road, Westport, CT 5 Beds \| 5 Baths \| 5573 Sq. Ft.	$3,782,968
9 Marc Lane, Westport, CT 6 Beds \| 5 Baths \| 4094 Sq. Ft.	$2,748,371
5 Rocky Acres Lane, Westport, CT 4 Beds \| 3.5 Baths \| 3960 Sq. Ft.	$2,632,121
86 Roseville Road, Westport, CT 3 Beds \| 2 Baths \| 1776 Sq. Ft.	$1,363,509

Address	Redfin Estimate
2 Windy Hill Road, Westport, CT 6 Beds \| 7 Baths \| 8185 Sq. Ft.	—
11 Windy Hill Road, Westport, CT 6 Beds \| 5 Baths \| 5015 Sq. Ft.	$3,452,920
8 Windy Hill Road, Westport, CT 7 Beds \| 6.5 Baths \| 6270 Sq. Ft.	$4,209,334
14 Windy Hill Road, Westport, CT 6 Beds \| 6 Baths \| 7063 Sq. Ft.	$4,914,007
63 Roseville Road, Westport, CT 4 Beds \| 4.5 Baths \| 4729 Sq. Ft.	$2,383,089
89 Roseville Road, Westport, CT 5 Beds \| 6 Baths \| 7574 Sq. Ft.	$3,698,580
9 Rocky Acres Lane, Westport, CT 4 Beds \| 3 Baths \| 2202 Sq. Ft.	$1,717,951

Property information provided by Smart MLS when last listed in 2024. This data may not match . Learn more.

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