Google street view image for 1 Chester Rd, Darien, CT 06820

Off market oct 1989 for $366K

$2,383,081

Est. refi paymentEst. refi $1,373/mo

•

3.5 ba

•

2,903

sq ft

1 Chester Rd, Darien, CT 06820

About this home

1 Chester Rd is a 2,903 square foot house on a 10,019 square foot lot with 5 bedrooms and 3.5 bathrooms. - it last sold on October 31, 1989 for $366,000. Based on Redfin's Darien data, we estimate the home's value is $2,383,081.

Single-familyProperty Type

1935Year Built

10,019 sq ftLot Size

$821Est. Price/Sq.Ft.

Source:Public Records

Redfin Estimate

$2,383,081

$2.0M since sold in October 1989$34K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 8.5% higher than the average sale price ($2.20M) of 6 comparable homes.

SOLD AUG 19, 2026
$3,352,000
A
5 beds3.5 baths3,621 sq ft
29 Hillcrest Ave, Darien, CT 06820
SOLD AUG 24, 2026
$1,776,000
B
4 beds3 baths2,745 sq ft
105 Holmes Ave, Darien, CT 06820
SOLD AUG 28, 2026
$1,985,000
C
5 beds3.5 baths2,977 sq ft
333 West Ave #5, Darien, CT 06820
SOLD SEP 23, 2026
$1,750,000
D
4 beds2.5 baths2,427 sq ft
2 Fairfield Ave, Darien, CT 06820
SOLD AUG 9, 2026
$1,915,000
E
5 beds4 baths3,115 sq ft
8 Glenwood Dr, Darien, CT 06820
SOLD MAY 19, 2026
$2,400,000
F
4 beds2.5 baths2,850 sq ft
86 Middlesex Rd, Darien, CT 06820

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Earn from this home

Sell

$2,244,207

Est. take-home

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Refinance

Est. cash available

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Rent

$6,122/mo

Redfin rental estimate

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Market trends in 06820, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

106.9%

2.0% MoM

Median sale price

$2.9M

$131K MoM

Avg. days on market

17d

4 days MoM

Recently sold homes

21 MoM

New listings for sale

NEW 14 HRS AGO
$6,985,000
7 beds10 baths9,058 sq ft
451 Mansfield Ave, Darien, CT 06820
OPEN SUN, 1PM TO 4PM
$4,995,000
6 beds5 baths6,040 sq ft
8 Bouton Ln, Darien, CT 06820
$5,025,000
6 beds3 baths4,477 sq ft
6 Berry Ln, Darien, CT 06820
OPEN SAT, 1PM TO 3PM
$4,725,000
6 beds6 baths6,459 sq ft
12 Seagate Rd, Darien, CT 06820
$1,850,000
4 beds3 baths3,414 sq ft
101 Hoyt St, Darien, CT 06820
$1,649,000
3 beds3 baths2,007 sq ft
27 Lakeside Ave, Darien, CT 06820
$2,699,000
5 beds4.5 baths4,084 sq ft
53 Country Club Rd, Darien, CT 06820
$7,995,000
5 beds6.5 baths5,172 sq ft
3 Coves End Rd, Darien, CT 06820
$1,895,000
4 beds2.5 baths2,456 sq ft
9 Wilson Ridge Rd E, Darien, CT 06820
$3,795,000
4 beds4 baths4,361 sq ft
5 Cross Rd, Darien, CT 06820
See all

Provided by Redfin

Sale history for 1 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2023

$15,864 (+2.2%)

$503,300 + $397,530

$900,830

2022

$15,521 (+2.3%)

$503,300 + $397,530

$900,830

2021

$15,170 (+3.1%)

$503,300 + $397,530

$900,830

2020

$14,711 (−0.8%)

$503,300 + $397,530

$900,830

2019

$14,837 (−3.9%)

$503,300 + $397,530

$900,830

2018

$15,443 (−0.5%)

$506,240 + $454,160

$960,400

2017

$15,520 (+2.5%)

$506,240 + $454,160

$960,400

2016

$15,146 (+5.1%)

$506,240 + $454,160

$960,400

2014

$14,416

$506,240 + $454,160

$960,400

Tax history for 1 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2023

$15,864 (+2.2%)

$503,300 + $397,530

$900,830

2022

$15,521 (+2.3%)

$503,300 + $397,530

$900,830

2021

$15,170 (+3.1%)

$503,300 + $397,530

$900,830

2020

$14,711 (−0.8%)

$503,300 + $397,530

$900,830

2019

$14,837 (−3.9%)

$503,300 + $397,530

$900,830

2018

$15,443 (−0.5%)

$506,240 + $454,160

$960,400

2017

$15,520 (+2.5%)

$506,240 + $454,160

$960,400

2016

$15,146 (+5.1%)

$506,240 + $454,160

$960,400

2014

$14,416

$506,240 + $454,160

$960,400

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

Property details

Interior

Basement Information
Basement Sq. Ft: 156
Basement Type: Full

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

Heating & Cooling
Heating Type: Central Forced Air

Fireplace Information
# of Fireplaces: 2
Has Fireplace

Room Information
# of Rooms: 10

Exterior

Exterior Information
Physical Condition: Very Good
Building Style Type: Colonial
Exterior Wall: Wood Siding/Shingle

Property Information
Living Sq. Ft: 2,903
Gross Sq. Ft: 2,903
# of Units: 1
# of Stories: 2

Lot Information
# of Buildings: 1
Land Sq. Ft: 10,019
Municipality Name: DARIEN
Acres: 0.23
Zoning Code: R13
State Use Description: 1-FAMILY RESIDENCE

Financial

Assessor Information
Assessment Year: 2023

Public facts

Beds: 5
Baths: 3.5
Sq. Ft.: 2,903
Stories: 2.0
Lot Size: 10,019 square feet
Style: Single Family Residential
Year Built: 1935
Year Renovated: 2009
County: Fairfield County
APN: 105271

Home facts updated by county records on Jul 13, 2023

Around this home

Schools

Holmes Elementary School

Public PreK-5 • Assigned • 0.3mi

9/10

Middlesex Middle School

Public 6-8 • Assigned • 0.6mi

10/10

Darien 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 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

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

$2.26M – $2.74M

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Nearby similar homes

$725,000

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New listings for sale in 06820

NEW 14 HRS AGO

$6,985,000

7 beds10 baths9,058 sq ft

451 Mansfield Ave, Darien, CT 06820

OPEN SUN, 1PM TO 4PM

$4,995,000

6 beds5 baths6,040 sq ft

8 Bouton Ln, Darien, CT 06820

$5,025,000

6 beds3 baths4,477 sq ft

6 Berry Ln, Darien, CT 06820

OPEN SAT, 1PM TO 3PMVIDEO TOUR

$4,725,000

6 beds6 baths6,459 sq ft

12 Seagate Rd, Darien, CT 06820

$1,850,000

4 beds3 baths3,414 sq ft

101 Hoyt St, Darien, CT 06820

$1,649,000

3 beds3 baths2,007 sq ft

27 Lakeside Ave, Darien, CT 06820

$2,699,000

5 beds4.5 baths4,084 sq ft

53 Country Club Rd, Darien, CT 06820

$7,995,000

5 beds6.5 baths5,172 sq ft

3 Coves End Rd, Darien, CT 06820

$1,895,000

4 beds2.5 baths2,456 sq ft

9 Wilson Ridge Rd E, Darien, CT 06820

Home values near 1 Chester Rd

Data from public records.

Address	Redfin Estimate
5 Chester Road, Darien, CT 4 Beds \| 2.5 Baths \| 2832 Sq. Ft.	$2,086,627
12 Chester Road, Darien, CT 4 Beds \| 2.5 Baths \| 2388 Sq. Ft.	$2,237,245

Address	Redfin Estimate
10 Chester Road, Darien, CT 3 Beds \| 2.5 Baths \| 2073 Sq. Ft.	$1,896,877
9 Chester Road, Darien, CT 4 Beds \| 3.5 Baths \| 3771 Sq. Ft.	$2,531,049

Address	Redfin Estimate
3 Chester Road, Darien, CT 3 Beds \| 2.5 Baths \| 2156 Sq. Ft.	$1,821,104
11 Chester Road, Darien, CT 4 Beds \| 3.5 Baths \| 3314 Sq. Ft.	$2,507,572

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06820, CT

Sale history for 1 Chester Rd

Tax history for 1 Chester Rd

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06820

Home values near 1 Chester Rd

More real estate resources