Off market jul 2025 for $2.3M

$2,485,333

Est. refi paymentEst. refi $3,742/mo

•

4,710

sq ft

1 Crooked Mile Rd, Westport, CT 06880

About this home

Originally built in 1929,the Keene-Calhoun home boasts a rich history,once owned by Oscar-winning film star Bette Davis.Nestled along the W. Branch Saugatuck Rvr,its entrance is adorned with stone pillars and mature plantings,leading to a captivating enclave.This iconic residence has been meticulously updated to preserve its antique allure while integrating modern amenities & sophisticated design.The LR is ideal for elegant entertaining with a wood-burning fireplace,a charming window seat,and handsome built-in shelving.A sophisticated Dining Room bathed in sunlight features a built-in hutch & another inviting window seat,perfect for lingering guests.The gourmet chef's Kitchen includes a spacious center island,granite countertops,high-end appliances & a cozy banquette,seamlessly flowing into the Great Room with warm coffered ceilings & surround sound.The Library,with a fireplace crafted from river stones,exudes coziness and charm.A 3-season screened porch leads to the bluestone terrace overlooking the river, providing serene spaces for relaxation,dining al fresco,or entertaining under the stars.The Primary Suite offers a fireplace, his & hers walk-in closets, a reading nook,& a spa-like bath with expansive windows framing picturesque river views.Add'ly, a legal apt. with a separate entrance and a 3-car garage enhance the appeal of this 5-bedroom, 4.5-bath home, blending old-world charm with contemporary comfort.Enjoy breathtaking river views and the tranquility of a

lush,park-like 1.14-acre setting, all within easy reach of Westport's vibrant amenities. Don't miss this opportunity to own a beautifully maintained antique home steeped in Westport history.

Single-familyProperty Type

1929Year Built

1.14 acresLot Size

$528Est. Price/Sq.Ft.

3 car garageParking

Listed by Ellen McNees • Higgins Group Real Estate

Listed by Christina McVaney • Higgins Group Real Estate

Bought with Kate Cacciatore • William Raveis Real Estate

Source:Smart MLS #24084318

Redfin Estimate

$2,485,333

$110K since sold in July 2025$60K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.7% higher than the average sale price ($2.33M) of 6 comparable homes.

SOLD SEP 18, 2026
$2,275,000
A
5 beds5.5 baths4,135 sq ft
18 River Ln, Westport, CT 06880
SOLD AUG 27, 2026
$2,400,000
B
4 beds4 baths4,013 sq ft
18 Silver Brook Rd, Westport, CT 06880
SOLD SEP 16, 2026
$1,925,000
C
4 beds3.5 baths2,881 sq ft
2 Grassy Plains Rd, Westport, CT 06880
SOLD JUL 15, 2026
$2,425,000
D
5 beds5 baths3,970 sq ft
52 Meadow View Dr, Westport, CT 06880
SOLD AUG 6, 2026
$2,550,000
E
5 beds4.5 baths4,179 sq ft
114 Cross Hwy, Westport, CT 06880
SOLD APR 2, 2026
$2,400,000
F
4 beds3.5 baths3,264 sq ft
13 River Ln, Westport, CT 06880

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Earn from this home

Sell

$486,590

Est. take-home

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Refinance

Est. cash available

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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 1 Crooked Mile Rd

Date

Event

Price

Smart MLS #24084318

Jul 8, 2025

Sold

$2,375,000

$504/sq ft

May 8, 2025

Pending

—

Apr 9, 2025

Listed

$2,275,000

$483/sq ft

Apr 7, 2025

Coming Soon

$2,275,000

$483/sq ft

Public Records

Jul 1, 1998

Sold

$708,000

$150/sq ft

Smart MLS #97018154

Jun 17, 1997

Listed

$729,000

$155/sq ft

Smart MLS #96020781

Sep 27, 1996

Listing Removed

—

Jun 13, 1996

Listed

$759,000

$161/sq ft

Smart MLS #96005071

May 31, 1996

Listing Removed

—

Feb 19, 1996

Listed

$759,000

$161/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$16,719 (+1.5%)

$478,500 + $432,600

$911,100

2022

$16,464

$478,500 + $432,600

$911,100

2021

$16,464 (−8.4%)

$478,500 + $432,600

$911,100

2020

$17,970 (−5.2%)

$503,700 + $571,700

$1,075,400

2019

$18,951

$503,700 + $620,300

$1,124,000

2018

$18,951

$503,700 + $620,300

$1,124,000

2017

$18,951

$503,700 + $620,300

$1,124,000

2016

$18,951 (+4.9%)

$503,700 + $620,300

$1,124,000

2014

$18,073

$464,100 + $543,300

$1,007,400

Tax history for 1 Crooked Mile Rd

Year

Property tax

Land + Additions

Assessment*

2023

$16,719 (+1.5%)

$478,500 + $432,600

$911,100

2022

$16,464

$478,500 + $432,600

$911,100

2021

$16,464 (−8.4%)

$478,500 + $432,600

$911,100

2020

$17,970 (−5.2%)

$503,700 + $571,700

$1,075,400

2019

$18,951

$503,700 + $620,300

$1,124,000

2018

$18,951

$503,700 + $620,300

$1,124,000

2017

$18,951

$503,700 + $620,300

$1,124,000

2016

$18,951 (+4.9%)

$503,700 + $620,300

$1,124,000

2014

$18,073

$464,100 + $543,300

$1,007,400

*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

3.5

Stories

Lot width

—

Lot depth

—

Lot size

1.14 Acres

Year renovated

—

Sq. Ft.

4,350

Year built

1929

Style

Multi-Family (2-4 Unit)

County

Fairfield County

APN

411556

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

Feb 25, 2020 • Final

Residential electric

Addition

Electrical

Kitchen

Feb 25, 2020 • Final

Residential electric

Install electrical wiring for a liquid propane generator.

Electrical

Generator

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, Detached Garage
Garages Number: 3

Interior

Interior Information
Total Rooms: 11
Laundry Room Info: Lower Level
Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Security System
In-Law Apartment: Yes
In-Law Access: Second Floor, Separate Entry
Fireplaces Total: 2
Cooling System: Central Air, Split System
Appliances Included: Gas Cooktop, Wall Oven, Microwave, Range Hood, Refrigerator, Dishwasher

Bathroom Information
# of Baths (Full): 4
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Bonus Room, Foyer, Laundry Room, Mud Room
Basement Description: Partial, Sump Pump, Interior Access, Partially Finished
Has Attic
Attic Description: Storage Space, Floored, Walk-up

Exterior

Exterior Features
Roof Information: Asphalt Shingle, Gable
Exterior Siding: Shingle, Wood
Exterior Features: Shed, Gutters, Stone Wall, Patio

Lot Information
Lot Description: Corner Lot, Lightly Wooded, Level Lot, Professionally Landscaped

Building Information
Foundation Type: Masonry, Stone
Construction Description: Frame
Color: white

Property Information
Waterfront Description: River, Beach Rights, Water Community, View
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 4350

Financial

Assessments Information
Assessed Value: $911,100

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Oil, Domestic
Heat Type: Baseboard, Hot Air, Radiant
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Generator, Programmable Thermostat, Storm Doors, Storm Windows

Location

School Information
Middle Jr High School: Coleytown
High School: Staples
Elementary School: Coleytown

Location Information
State: Connecticut
Nearby Amenities: Health Club, Private School(s), Public Pool, Public Rec Facilities, Public Transportation
Flood Zone
Directions: Cavalry or Newtown Tpk to Crooked Mile
Direct Waterfront
County: Fairfield

Public facts

Beds: 3
Baths: 3.5
Sq. Ft.: 4,350
Stories: 2.0
Lot Size: 1.14 acres
Style: Multi-Family (2-4 Unit)
Year Built: 1929
Year Renovated: —
County: Fairfield County
APN: 411556

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

3/10 Flood Factor

Estimated 10-14% chance 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

$2.36M – $2.86M

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Home values near 1 Crooked Mile Rd

Data from public records.

Address	Redfin Estimate
9 Crooked Mile Rd, Westport, CT 6 Beds \| 6 Baths \| 7076 Sq. Ft.	$3,680,176
3 Crooked Mile Rd, Westport, CT 3 Beds \| 3 Baths \| 4290 Sq. Ft.	$2,514,316
7 Crooked Mile Rd, Westport, CT 6 Beds \| 5 Baths \| 3919 Sq. Ft.	$2,528,203
176 Newtown Tpke, Westport, CT 4 Beds \| 3 Baths \| 3310 Sq. Ft.	$1,822,864
162 Newtown Tpke, Westport, CT 5 Beds \| 5.5 Baths \| 6032 Sq. Ft.	$2,527,940
4 Broad St, Westport, CT 4 Beds \| 2.5 Baths \| 2653 Sq. Ft.	$1,652,092
1 Broad St, Westport, CT 5 Beds \| 4.5 Baths \| 5474 Sq. Ft.	$3,622,474

Address	Redfin Estimate
2 Crooked Mile Rd, Westport, CT 4 Beds \| 3.5 Baths \| 2787 Sq. Ft.	$1,777,473
10 Crooked Mile Rd, Westport, CT 4 Beds \| 3.5 Baths \| 4313 Sq. Ft.	$2,300,808
8 Crooked Mile Rd, Westport, CT 4 Beds \| 4 Baths \| 3798 Sq. Ft.	$2,859,340
168 Newtown Tpke, Westport, CT 4 Beds \| 2.5 Baths \| 2811 Sq. Ft.	$1,984,266
173 Newtown Tpke, Westport, CT 4 Beds \| 2.5 Baths \| 2352 Sq. Ft.	$1,385,466
164 Newtown Tpke, Westport, CT 4 Beds \| 2 Baths \| 4090 Sq. Ft.	—
10 Broad St, Westport, CT 4 Beds \| 3 Baths \| 3866 Sq. Ft.	$1,878,045

Address	Redfin Estimate
5 Crooked Mile Rd, Westport, CT 4 Beds \| 3.5 Baths \| 4133 Sq. Ft.	$3,890,004
4 Crooked Mile Rd, Westport, CT 5 Beds \| 7.5 Baths \| 7179 Sq. Ft.	$4,933,003
177 Newtown Tpke, Westport, CT 5 Beds \| 3.5 Baths \| 3112 Sq. Ft.	$1,606,360
2 Broad St, Westport, CT 4 Beds \| 2.5 Baths \| 2556 Sq. Ft.	$1,623,509
8 Twin Bridge Acre Rd, Westport, CT 5 Beds \| 4 Baths \| 4433 Sq. Ft.	$2,606,086
10 Twin Bridge Acre Rd, Westport, CT 5 Beds \| 7.5 Baths \| 6264 Sq. Ft.	$3,153,174
6 Twin Bridge Acre Rd, Westport, CT 4 Beds \| 4.5 Baths \| 3065 Sq. Ft.	$2,008,383

Property information provided by Smart MLS when last listed in 2025. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06880, CT

Sale history for 1 Crooked Mile Rd

Tax history for 1 Crooked Mile Rd

Public record

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 1 Crooked Mile Rd

More real estate resources