Google street view image for 2 Crooked Mile Rd, Westport, CT 06880

Off market

$1,777,473

•

3.5 ba

•

2,787

sq ft

2 Crooked Mile Rd, Westport, CT 06880

About this home

2 Crooked Mile Rd is a 2,787 square foot house on a 0.63 acre lot with 4 bedrooms and 3.5 bathrooms. Based on Redfin's Westport data, we estimate the home's value is $1,777,473.

Single-familyProperty Type

1938Year Built

0.63 acresLot Size

$638Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$1,777,473

$7,000 since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 12.6% higher than the average sale price ($1.58M) of 6 comparable homes.

SOLD APR 2, 2026
$2,400,000
A
4 beds3.5 baths3,264 sq ft
13 River Ln, Westport, CT 06880
SOLD AUG 24, 2026
$1,112,000
B
4 beds3 baths3,024 sq ft
211 Newtown Tpke, Wilton, CT 06897
SOLD SEP 16, 2026
$1,925,000
C
4 beds3.5 baths2,881 sq ft
2 Grassy Plains Rd, Westport, CT 06880
SOLD MAY 6, 2026
$1,160,000
D
4 beds3 baths2,862 sq ft
6 Downe Ln, Wilton, CT 06897
SOLD OCT 27, 2026
$1,955,000
E
4 beds4 baths3,174 sq ft
5 Northfield Dr, Westport, CT 06880
SOLD JUN 1, 2026
$922,500
F
4 beds3 baths2,600 sq ft
2 Thistle Rd, Norwalk, CT 06851

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Earn from this home

Sell

$1,673,361

Est. take-home

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Rent

$4,201/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 SUN, 12PM TO 2PM
$1,599,000
5 beds4 baths3,519 sq ft
23 Meeker Rd, Westport, CT 06880
OPEN SUN, 12PM TO 3PM
$1,799,000
4 beds3 baths2,725 sq ft
4 Bruce Ln, Westport, CT 06880
OPEN SUN, 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 SUN, 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 SUN, 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 2 Crooked Mile Rd

As the MLS and public records start to fill up, we'll list the details here.

Year

Property tax

Land + Additions

Assessment*

2023

$11,931 (+1.5%)

$417,600 + $232,600

$650,200

2022

$11,749

$417,600 + $232,600

$650,200

2021

$11,749 (−5.4%)

$417,600 + $232,600

$650,200

2020

$12,421 (−0.9%)

$440,300 + $303,000

$743,300

2019

$12,532

$440,300 + $303,000

$743,300

2018

$12,532

$440,300 + $303,000

$743,300

2017

$12,532

$440,300 + $303,000

$743,300

2016

$12,532 (+15.7%)

$440,300 + $303,000

$743,300

2014

$10,832

$319,800 + $284,000

$603,800

Tax history for 2 Crooked Mile Rd

Year

Property tax

Land + Additions

Assessment*

2023

$11,931 (+1.5%)

$417,600 + $232,600

$650,200

2022

$11,749

$417,600 + $232,600

$650,200

2021

$11,749 (−5.4%)

$417,600 + $232,600

$650,200

2020

$12,421 (−0.9%)

$440,300 + $303,000

$743,300

2019

$12,532

$440,300 + $303,000

$743,300

2018

$12,532

$440,300 + $303,000

$743,300

2017

$12,532

$440,300 + $303,000

$743,300

2016

$12,532 (+15.7%)

$440,300 + $303,000

$743,300

2014

$10,832

$319,800 + $284,000

$603,800

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

Permits

Apr 27, 2023 • Active

Residential roof

Roofing

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

Interior

Bathroom Information
# of Full Baths: 3
# of 1/2 Baths: 1

Heating & Cooling
Heating Type: Forced Hot Water

Fireplace Information
# of Fireplaces: 2
Has Fireplace

Room Information
# of Rooms: 10

Exterior

Exterior Information
Physical Condition: Good
Building Style Type: Colonial
Exterior Wall: Wood Siding/Shingle
Roof Shape Type: Gable

Property Information
Living Sq. Ft: 2,787
Gross Sq. Ft: 5,710
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 27,443
Municipality Name: WESTPORT
Acres: 0.63
Zoning Code: AA
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 4
Baths: 3.5
Sq. Ft.: 2,787
Stories: 2.0
Lot Size: 0.63 acres
Style: Single Family Residential
Year Built: 1938
Year Renovated: —
County: Fairfield County
APN: 412596

Home facts updated by county records on Jul 12, 2023

Around this home

Schools

K - 12
Preschool & daycare

Coleytown Elementary School

Public K-5 • Assigned • 1.6mi

9/10

Coleytown Middle School

Public 6-8 • Assigned • 1.5mi

10/10

Staples High School

Public 9-12 • Assigned • 3.1mi

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, 16 days in 30 years

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

3 unhealthy days expected this year, 5 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 8.7 hours in June and 4.3 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.69M – $2.05M

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New listings for sale in 06880

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Beautiful kitchen • Two fireplaces • Finished level

OPEN SUN, 12PM TO 3PM

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4 Morningside Dr N #102, Westport, CT 06880

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

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4 Morningside Dr N #301, Westport, CT 06880

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OPEN SUN, 1PM TO 3PM

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5 beds6.5 baths4,854 sq ft

12 Bauer Pl, Westport, CT 06880

Cul-de-sac • Chef's kitchen • Thermador appliances

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2 beds2.5 baths1,440 sq ft

25 Strathmore Ln #25, Westport, CT 06880

Large living area • Composite deck • Wooded view

Home values near 2 Crooked Mile Rd

Data from public records.

Address	Redfin Estimate
9 Crooked Mile Road, Westport, CT 6 Beds \| 6 Baths \| 7076 Sq. Ft.	$3,680,176
1 Crooked Mile Road, Westport, CT 5 Beds \| 4.5 Baths \| 4710 Sq. Ft.	$2,485,333
7 Crooked Mile Road, Westport, CT 6 Beds \| 5 Baths \| 3919 Sq. Ft.	$2,528,203
177 Newtown Turnpike, Westport, CT 5 Beds \| 3.5 Baths \| 3112 Sq. Ft.	$1,606,360
2 Broad Street, Westport, CT 4 Beds \| 2.5 Baths \| 2556 Sq. Ft.	$1,623,509
8 Twin Bridge Acre Road, Westport, CT 5 Beds \| 4 Baths \| 4433 Sq. Ft.	$2,606,086
164 Newtown Turnpike, Westport, CT 4 Beds \| 2 Baths \| 4090 Sq. Ft.	—

Address	Redfin Estimate
5 Crooked Mile Road, Westport, CT 4 Beds \| 3.5 Baths \| 4133 Sq. Ft.	$3,890,004
10 Crooked Mile Road, Westport, CT 4 Beds \| 3.5 Baths \| 4313 Sq. Ft.	$2,300,808
8 Crooked Mile Road, Westport, CT 4 Beds \| 4 Baths \| 3798 Sq. Ft.	$2,859,340
176 Newtown Turnpike, Westport, CT 4 Beds \| 3 Baths \| 3310 Sq. Ft.	$1,822,864
162 Newtown Turnpike, Westport, CT 5 Beds \| 5.5 Baths \| 6032 Sq. Ft.	$2,527,940
4 Broad Street, Westport, CT 4 Beds \| 2.5 Baths \| 2653 Sq. Ft.	$1,652,092
6 Twin Bridge Acre Road, Westport, CT 4 Beds \| 4.5 Baths \| 3065 Sq. Ft.	$2,008,383

Address	Redfin Estimate
3 Crooked Mile Road, Westport, CT 3 Beds \| 3 Baths \| 4290 Sq. Ft.	$2,514,316
4 Crooked Mile Road, Westport, CT 5 Beds \| 7.5 Baths \| 7179 Sq. Ft.	$4,933,003
159 Newtown Turnpike, Weston, CT 5 Beds \| 5.5 Baths \| 5131 Sq. Ft.	—
168 Newtown Turnpike, Westport, CT 4 Beds \| 2.5 Baths \| 2811 Sq. Ft.	$1,984,266
173 Newtown Turnpike, Westport, CT 4 Beds \| 2.5 Baths \| 2352 Sq. Ft.	$1,385,466
157 Newtown Turnpike, Westport, CT 3 Beds \| 2.5 Baths \| 3397 Sq. Ft.	$1,676,047
9 Twin Bridge Acre Road, Westport, CT 3 Beds \| 2 Baths \| 2036 Sq. Ft.	$1,323,432

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About this home

Redfin Estimate

Earn from this home

Market trends in 06880, CT

Sale history for 2 Crooked Mile Rd

Tax history for 2 Crooked Mile Rd

Permits

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06880

Home values near 2 Crooked Mile Rd

More real estate resources