Off Market Jul 2024 for $1.9M

$2,536,085

Est. refi paymentEst. refi $8,681/mo

•

2,855

sq ft

14 Chester Rd, Darien, CT 06820

About this home

Move right into this spectacular home in one of the most sought-after neighborhoods in Darien. It's located just steps from Woodland Park and within walking distance of Holmes Elementary, Middlesex Middle School, and Darien High School, as well as the newly developed Darien Commons and the Noroton Heights train station. As you enter, you will find an inviting living room with a wood-burning fireplace and a private office attached. The elegant dining room is the perfect space for entertaining family and friends. A sun-filled family room with high ceilings, floor-to-ceiling windows, and sliders to an outdoor deck is located right off the kitchen. The kitchen was renovated in 2021 complete with custom cabinetry, quartz counters, a large island, and top-of-the-line appliances. The spacious upstairs includes four bedrooms and two full baths. A third-floor bonus room is located off one of the bedrooms and can be used as an extra play space or a quiet place for reading, studying, or watching movies. This home is not to be missed!

Single-familyProperty Type

1931Year Built

9,147 sq ftLot Size

$888Est. Price/Sq.Ft.

2 car garageParking

Listed by Sarah Caras • Houlihan Lawrence

Bought with Kristin Nemec • William Pitt Sotheby's Int'l

Source:Smart MLS #24004539

Redfin Estimate

$2,536,085

$605K since sold in July 2024$51K since July

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 22.8% higher than the average sale price ($2.07M) of 6 comparable homes.

SOLD JUN 29, 2026
$1,550,000
A
4 beds2.5 baths2,108 sq ft
6 Park Ln, Darien, CT 06820
SOLD JUN 1, 2026
$2,258,000
B
4 beds2.5 baths2,450 sq ft
3 Abbey Rd, Darien, CT 06820
SOLD JUL 31, 2026
$2,365,000
C
4 beds2.5 baths3,264 sq ft
19 Chester Rd, Darien, CT 06820
SOLD AUG 6, 2026
$2,495,033
D
4 beds2 baths2,692 sq ft
33 Walmsley Rd, Darien, CT 06820
SOLD MAY 19, 2026
$2,400,000
E
4 beds2.5 baths2,850 sq ft
86 Middlesex Rd, Darien, CT 06820
SOLD AUG 13, 2026
$1,325,000
F
4 beds2 baths1,402 sq ft
13 Devon Rd, Darien, CT 06820

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Earn from this home

Sell

$903,429

Est. take-home

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Refinance

Est. cash available

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Rent

$5,690/mo

Redfin rental estimate

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Market trends in 06820, CT

Last updated July 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

112.0%

+1.8% MoM

Median sale price

$3.0M

$202K MoM

Avg. days on market

12d

1 days MoM

Recently sold homes

30 MoM

New listings for sale

COMING SOON
$1,050,000
4 beds1.5 baths1,883 sq ft
29 Lynn Ct, Darien, CT 06820
OPEN SAT, 1PM TO 2:30PM
$949,000
2 beds1 bath910 sq ft
64 Noroton Ave, Darien, CT 06820
OPEN SAT, 1PM TO 3PM
$2,250,000
4 beds3.5 baths3,511 sq ft
1644 Boston Post Rd, Darien, CT 06820
$1,999,000
4 beds2.5 baths3,065 sq ft
2 Stony Brook Rd S, Darien, CT 06820
OPEN SUN, 1PM TO 3PM
$1,495,000
4 beds2 baths3,182 sq ft
1646 Boston Post Rd, Darien, CT 06820
COMING SOON
$7,500,000
5 beds7 baths10,213 sq ft
460 Middlesex Rd, Darien, CT 06820
$1,299,000
3 beds2 baths3,094 sq ft
53 Maple St, Darien, CT 06820
$3,950,000
5 beds5.5 baths5,500 sq ft
700 Hollow Tree Ridge Rd, Darien, CT 06820
See all

Provided by Redfin

Sale history for 14 Chester Rd

Date

Event

Price

Smart MLS #24004539

Jul 15, 2024

Sold

$1,930,800

$676/sq ft

May 10, 2024

Pending

—

May 2, 2024

Listed

$1,725,000

$604/sq ft

Apr 29, 2024

Coming Soon

$1,725,000

$604/sq ft

Public Records

Nov 21, 2016

Sold

$1,350,000

$473/sq ft

Smart MLS #99120992

Nov 21, 2016

Listing Removed

—

Nov 18, 2016

Sold

$1,350,000

$473/sq ft

Sep 23, 2015

Listed

$1,395,000

$489/sq ft

Move right in to this picture perfect home with fantastic curb appeal in sought-after neighborhood. The perfect combination of spacious casual and formal rooms for everyday living. Substantial millwork and beautiful hardwood floors mark the interior. Sun-filled great room with high ceilings, French doors and floor-to-ceiling windows. The kitchen boasts custom cabinetry, granite counters, large island and top-of-the-line appliances. Private, cozy first floor office with built-ins. The second floor ncludes a master bedroom with renovated en suite master bath. Plus large third floor playroom, renovated in 2015. Perfectly landscaped, yet easy to maintain yard with large deck, perfect for entertaining. Walk to schools and Woodland Park.

Living room heated by heat pump not cast iron baseboard

Smart MLS #99119471

Sep 21, 2015

Listing Removed

—

Sep 11, 2015

Listed

$1,649,000

$578/sq ft

Public Records

Jul 1, 2011

Sold

$1,425,000

$499/sq ft

Public Records

May 26, 2000

Sold

$663,209

$232/sq ft

Public Records

Apr 2, 1993

Sold

$438,000

$153/sq ft

Public Records

Oct 3, 1988

Sold

$409,000

$143/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$16,762 (+2.2%)

$499,380 + $452,480

$951,860

2022

$16,401 (+8.0%)

$499,380 + $452,480

$951,860

2021

$15,182 (+3.1%)

$499,380 + $402,150

$901,530

2020

$14,722 (−0.8%)

$499,380 + $402,150

$901,530

2019

$14,848 (+1.0%)

$499,380 + $402,150

$901,530

2018

$14,706 (−0.5%)

$502,320 + $412,230

$914,550

2017

$14,779 (+2.5%)

$502,320 + $412,230

$914,550

2016

$14,422 (+5.1%)

$502,320 + $412,230

$914,550

2014

$13,727

$502,320 + $412,230

$914,550

Tax history for 14 Chester Rd

Year

Property tax

Land + Additions

Assessment*

2023

$16,762 (+2.2%)

$499,380 + $452,480

$951,860

2022

$16,401 (+8.0%)

$499,380 + $452,480

$951,860

2021

$15,182 (+3.1%)

$499,380 + $402,150

$901,530

2020

$14,722 (−0.8%)

$499,380 + $402,150

$901,530

2019

$14,848 (+1.0%)

$499,380 + $402,150

$901,530

2018

$14,706 (−0.5%)

$502,320 + $412,230

$914,550

2017

$14,779 (+2.5%)

$502,320 + $412,230

$914,550

2016

$14,422 (+5.1%)

$502,320 + $412,230

$914,550

2014

$13,727

$502,320 + $412,230

$914,550

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

Public record

Beds

Baths

2.5

Stories

Lot width

—

Lot depth

—

Lot size

9,147

Year renovated

2021

Sq. Ft.

2,855

Year built

1931

Style

Single Family Residential

County

Fairfield County

APN

105285

Parking Spaces

Basement

Yes

Accessible

HOA Dues

—

Garage

Yes

Features

—

Last updated by owner on Jul 18, 2024.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage
Garages Number: 2

Interior

Virtual Tour Information

Interior Information
Total Rooms: 11
Laundry Room Location: Main Level
Laundry Room Info: Main Level
Interior Features: Security System
In-Law Apartment: No
Fireplaces Total: 1
Cooling System: Central Air, Wall Unit
Appliances Included: Gas Range, Microwave, Refrigerator, Freezer, Subzero, Dishwasher, Disposal, Washer, Dryer

Bathroom Information
# of Baths (Full): 2
# of Baths (Half): 1

Bedroom Information
Beds Total: 4

Room Information
Basement Description: Full, Unfinished
Has Attic
Attic Description: Partially Finished, Walk-up

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Brick, Stucco
Exterior Features: Deck, Underground Sprinkler

Lot Information
Lot Description: Level Lot

Building Information
Foundation Type: Masonry
Construction Description: Frame

Property Information
Waterfront Description: Beach Rights
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 2855

Financial

Assessments Information
Assessed Value: $1,250,340

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Public Sewer Connected
Hot Water Description: Natural Gas, 80 Gallon Tank
Heat Type: Hot Water
Heat Fuel Type: Natural Gas

Location

School Information
High School: Darien
Elementary School: Holmes

Location Information
State: Connecticut
Nearby Amenities: Library, Paddle Tennis, Park, Playground/Tot Lot, Tennis Courts
Directions: Middlesex Road to Chester Road
County: Fairfield

Public facts

Beds: 4
Baths: 2.5
Sq. Ft.: 2,855
Stories: 2.0
Parking Spaces: 2
Basement: Yes
Accessible: No
Lot Size: 9,147 square feet
Style: Single Family Residential
Year Built: 1931
Year Renovated: 2021
County: Fairfield County
APN: 105285
HOA Dues: —
Garage: Yes
Features: —

Home facts updated by owner on Jul 18, 2024

Other

Documents & Disclosures
Supplement Count Public: 4

Around this home

Schools

Holmes Elementary School

Public PreK-5 • Assigned • 0.4mi

9/10

Middlesex Middle School

Public 6-8 • Assigned • 0.5mi

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

$2.41M – $2.92M

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Mike Parelli Real Estate LLC

New listings for sale in 06820

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OPEN SAT, 1PM TO 2:30PM

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Home values near 14 Chester Rd

Data from public records.

Address	Redfin Estimate
5 Chester Road, Darien, CT 4 Beds \| 2.5 Baths \| 2832 Sq. Ft.	$2,176,272
18 Chester Road, Darien, CT 4 Beds \| 2.5 Baths \| 2194 Sq. Ft.	$1,953,010

Address	Redfin Estimate
10 Chester Road, Darien, CT 3 Beds \| 2.5 Baths \| 2073 Sq. Ft.	$2,030,448
17 Chester Road, Darien, CT 3 Beds \| 2 Baths \| 2088 Sq. Ft.	$1,903,050

Address	Redfin Estimate
3 Chester Road, Darien, CT 3 Beds \| 2.5 Baths \| 2156 Sq. Ft.	$1,937,926
20 Chester Road, Darien, CT 4 Beds \| 2.5 Baths \| 2133 Sq. Ft.	$2,183,183

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

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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 14 Chester Rd

Tax history for 14 Chester Rd

Public record

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 14 Chester Rd

More real estate resources