Sold on Jun 2026

$4,315,000

•

4,653

sq ft

28 Crooked Mile Rd, Darien, CT 06820

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About this home

Welcome to 28 Crooked Mile Road! Privately sited at the end of a quiet cul-de-sac in North Darien on a private road in the Ox Ridge school district, this handsome cedar shingle-clad colonial sits on two beautifully manicured acres with mature trees and planting beds. The property offers wonderful western and southern exposure, the house is truly flooded with sunshine throughout the day. The home underwent a major renovation in 2007 and more recently, in 2020, the kitchen and bar area had a fabulous redo!. The classic shaker style kitchen shares an adjacent family room with a fireplace and access to the patio beyond. Formal living and dining rooms and an office anchor the first floor, along with a magazine worthy, newly renovated sunroom (complete with wet bar)! The second floor holds 5 bedrooms. Four are en-suite and positioned along the south side of the house, while a 5th (and potential 6th) bedroom sit on the North side - well suited for guests, older children or an au pair. Also, up the back stairs, is a generous bonus room, perfect for any number of activities! In 2025 the entire roof was replaced, and an array of solar panels were installed on the rear of the home. An electric car charger in the 3-car garage and generator complete this very well-equipped house. Don't miss the chance to make this well maintained and beautifully updated colonial your forever home!

Crooked Mile Tax District is a "special tax district" in the Town of Darien under Connecticut Law. The tax bill for 28 Crooked Mile for the fiscal year 2025-2026 was $1467.69. Funds collected are used for road & property maintenance, plowing, etc.

Single-familyProperty Type

1961Year Built

2 acresLot Size

$927Price/Sq.Ft.

3 garage spacesParking

Listed by Nan Peter • Houlihan Lawrence

Contact: Agent Attribution Contact: (203) 247-1188 | Office Attribution Contact: (203) 655-8238

Bought with Bob Green • William Pitt Sotheby's Int'l

Source:Smart MLS #24148496

Redfin Estimate

$4,504,288

$189K since sold in June 2026$61K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 26.3% higher than the average sale price ($3.57M) of 6 comparable homes.

SOLD SEP 1, 2026
$2,450,000
A
5 beds5 baths5,458 sq ft
235 Hawks Hill Rd, New Canaan, CT 06840
SOLD MAY 29, 2026
$4,500,000
B
5 beds5 baths5,864 sq ft
6 Cloudy Ln, Darien, CT 06820
SOLD APR 15, 2026
$3,308,000
C
5 beds4 baths3,509 sq ft
5 Wheat Ln, Darien, CT 06820
SOLD AUG 12, 2026
$3,850,000
D
6 beds6.5 baths5,113 sq ft
30 Inwood Rd, Darien, CT 06820
SOLD AUG 6, 2026
$3,795,000
E
5 beds6.5 baths6,424 sq ft
39 Leeuwarden Rd, Darien, CT 06820
SOLD AUG 14, 2026
$3,500,000
F
5 beds6 baths6,144 sq ft
59 Running Brook Ln, New Canaan, CT 06840

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Market trends in 06820, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

109.0%

1.3% MoM

Median sale price

$3.0M

$23K MoM

Avg. days on market

13d

0 days MoM

Recently sold homes

112

9 MoM

New listings for sale

COMING SOON
$3,600,000
5 beds4.5 baths4,423 sq ft
18 Bates Farm Ln, Darien, CT 06820
FOR SALE BY OWNER
$2,200,000
5 beds4 baths3,033 sq ft
13 Silver Lakes Dr, Darien, CT 06820
$7,500,000
5 beds7 baths10,213 sq ft
460 Middlesex Rd, Darien, CT 06820
$2,895,000
4 beds2.5 baths4,080 sq ft
30 Birch Rd, Darien, CT 06820
$3,825,000
5 beds3.5 baths4,400 sq ft
21 Harbor Rd, Darien, CT 06820
$1,895,000
4 beds3 baths2,303 sq ft
13 Chestnut St, Darien, CT 06820
VIDEO TOUR
$3,595,000
3 beds4.5 baths4,733 sq ft
31 Hancock Ln, Darien, CT 06820
3D WALKTHROUGH
$1,200,000
3 beds2 baths1,974 sq ft
145 West Ave, Darien, CT 06820
$1,749,000
4 beds2.5 baths2,106 sq ft
60 Middlesex Rd, Darien, CT 06820
$3,925,000
4 beds3.5 baths4,093 sq ft
20 Lighthouse Way, Darien, CT 06820
See all

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Rental estimate

Est. $7,237 per month, based on comparable rentals

Sale and tax history for 28 Crooked Mile Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$27,276 (+2.2%)

$749,210 + $799,680

$1,548,890

2022

$26,687 (+2.3%)

$749,210 + $799,680

$1,548,890

2021

$26,083 (+3.1%)

$749,210 + $799,680

$1,548,890

2020

$25,293 (−0.9%)

$749,210 + $799,680

$1,548,890

2019

$25,510 (−12.3%)

$749,210 + $799,680

$1,548,890

2018

$29,097 (−0.5%)

$844,760 + $964,740

$1,809,500

2017

$29,242 (+2.5%)

$844,760 + $964,740

$1,809,500

2016

$28,536 (+5.1%)

$844,760 + $964,740

$1,809,500

2014

$27,161

$844,760 + $964,740

$1,809,500

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

2.03 Acres

Year renovated

2007

Sq. Ft.

4,653

Year built

1961

Style

Single Family Residential

County

Fairfield County

APN

102896

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

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

Parking Information
Parking Total Spaces: 5

Interior

Interior Information
Total Rooms: 15
Laundry Room Location: First floor off the mud-room.
Laundry Room Info: Main Level
Interior Features: Auto Garage Door Opener, Cable - Pre-wired, Security System
Security System, Thermostat(s)
Fireplaces Total: 2
Cooling System: Central Air, Heat Pump
Appliances Included: Gas Cooktop, Cook Top, Wall Oven, Range Hood, Refrigerator, Subzero, Dishwasher, Disposal, Washer, Dryer

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

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Bonus Room, Foyer, Laundry Room, Mud Room
Basement Description: Partial, Unfinished, Storage, Interior Access, Concrete Floor
Has Attic
Attic Description: Storage Space, Walk-up

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Shingle, Cedar
Exterior Features: Underground Utilities, Gutters, French Doors, Underground Sprinkler, Patio

Lot Information
Lot Description: Dry, Level Lot, On Cul-De-Sac, Professionally Landscaped, Open Lot

Building Information
Foundation Type: Block
Construction Description: Frame
Color: White

Property Information
Property Type: Single Family For Sale
Driveway Type: Private, Paved, Asphalt

Financial

Assessments Information
Assessed Value: $2,106,090

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: Oil, 65 Gallon Tank
Heat Type: Heat Pump, Hot Air
Heat Fuel Type: Electric, Oil
Fuel Tank Location: In Basement
Energy Features: Active Solar, Generator, Programmable Thermostat, Thermopane Windows

Location

School Information
Middle Jr High School: Middlesex
High School: Darien
Elementary School: Ox Ridge

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Park, Public Transportation, Shopping/Mall, Tennis Courts
Directions: Hollow Tree Ridge Road to Crooked Mile Road
County: Fairfield

Public facts

Beds: 5
Baths: 4.0
Sq. Ft.: 4,653
Stories: 2.0
Lot Size: 2.03 acres
Style: Single Family Residential
Year Built: 1961
Year Renovated: 2007
County: Fairfield County
APN: 102896

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 4

Around this home

Schools

Ox Ridge Elementary School

Public PreK-5 • Assigned • 0.6mi

10/10

Middlesex Middle School

Public 6-8 • Assigned • 2.2mi

10/10

Darien High School

Public 9-12 • Assigned • 1.4mi

10/10

Provided by GreatSchools

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 99° expected this year, 15 days in 30 years

6/10 Wind Factor

67% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 days in 30 years

Provided by First Street

Historical weather

Darien, CT • 06820

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

88/ 100

Very good sunlight

Sunscore

This home ranks in the top 30% for direct sun exposure in Darien. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

8.9 hrs

5.1 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$4.28M – $5.18M

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Home values near 28 Crooked Mile Rd

Data from public records.

Address	Redfin Estimate
14 Crooked Mile Rd, Darien, CT 4 Beds \| 3.5 Baths \| 4615 Sq. Ft.	$3,727,045
34 Crooked Mile Rd, Darien, CT 6 Beds \| 3.5 Baths \| 3307 Sq. Ft.	$3,181,305

Address	Redfin Estimate
25 Crooked Mile Rd, Darien, CT 3 Beds \| 2.5 Baths \| 3246 Sq. Ft.	$2,864,308
35 Crooked Mile Rd, Darien, CT 5 Beds \| 6.5 Baths \| 9351 Sq. Ft.	$5,604,512

Address	Redfin Estimate
6 Crooked Mile Rd, Darien, CT 5 Beds \| 3 Baths \| 3793 Sq. Ft.	$3,560,061
30 Crooked Mile Rd, Darien, CT 6 Beds \| 6 Baths \| 5100 Sq. Ft.	$4,219,676

Property information provided by Smart MLS when last listed in 2026. This data may not match . Learn more.

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About this home

Redfin Estimate

Market trends in 06820, CT

Homeowner tools

Sale and tax history for 28 Crooked Mile Rd

Public record

Property details

Around this home

Schools

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06820

Home values near 28 Crooked Mile Rd

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