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$2,225,000

  • For Sale
  • Under Contract
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,264 Sq. Ft.
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This storybook charmer sits on a rare half acre of flat, dry land directly abutting Woodland Park, creating a setting that feels both private and enchanting. Summer entertaining comes naturally here; think firepit conversations, dinners on the patio, and long evenings surrounded by nature. The four-bedroom, two-and-a-half bath layout offers great flow, with the kitchen opening to the family room and a classic dining and living room arrangement anchored by a fireplace. All of this in one of Darien's most beloved neighborhoods, walkable to schools, train, and shopping.

Full Property Details for 19 Chester Rd

General

  • Price: $2,225,000
  • Taxes: (July 2025-June 2026)
  • Status: Under Contract
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24170445
  • Updated: 5/20/2026
  • Added to Site: 69 day(s) ago

Interior

  • Number of Rooms: 9
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Appliances: Gas Cooktop, Wall Oven, Microwave, Range Hood, Subzero, Dishwasher, Washer, Dryer

Rooms

Bathrooms

  • Total Bathrooms: 3
  • Full Bathrooms: 2
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Cathedral Ceiling, Full Bath, Walk-In Closet, Hardwood Floor, 19 x 15, Upper
  • Bedroom 1: Bedroom - Wall/Wall Carpet, Hardwood Floor, 12 x 12, Upper
  • Bedroom 2: Bedroom - Walk-In Closet, Hardwood Floor, 14 x 14, Upper
  • Bedroom 3: Bedroom - Balcony/Deck, Hardwood Floor, 15 x 12, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 26 x 13, Main
  • Family Room: Family Room - Built-Ins, Ceiling Fan, Hardwood Floor, 18 x 19, Main
  • Kitchen: Kitchen - Breakfast Bar, Wet Bar, Hardwood Floor, 15 x 16, Main
  • Dining Room: Dining Room - Patio/Terrace, 15 x 12, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Book Shelves, Built-Ins, Wall/Wall Carpet, On 3rd Floor, 14 x 12, Upper
  • Rec Room: Book Shelves, Built-Ins, Wall/Wall Carpet, On 3rd Floor, 14 x 12, Upper
  • Laundry: Main Level

Exterior

  • Exterior Features: Porch-Screened, Shed, Porch, Patio
  • Color: White

Parking

  • Total Spaces: 4
  • Parking: Driveway

Location

  • County: Fairfield
  • Driving Directions: Middlesex to Chester

School Information

  • Elementary School: Holmes
  • Middle School: Middlesex
  • High School: Darien

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Water, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: Oil, 40 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Tudor
  • Construction Status: No/Resale
  • Exterior Const.: Shingle, Brick
  • Basement Desc.: Full, Unfinished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,264
  • Above Ground: 3,264 Sq. Ft.
  • Year Built: 1931

Lot Features

  • Lot Size (Acres): 0.5
  • Driveway/Sidewalk: Gravel
  • Zoning: R13
  • Lot Description: Borders Open Space, Level Lot, On Cul-De-Sac, Professionally Landscaped

Water Features

  • Water Front Desc.: Beach Rights

Green Features

  • Energy Features: Programmable Thermostat

Financial Considerations

  • Assessment Amount: $1,178,730
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: See exclusion/inclusion list
  • Property ID: 2463566

Listed by Houlihan Lawrence, Heather Hilleman

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Listing agent

— 19 Chester Rd —

  • Heather Hilleman

    Houlihan Lawrence

Agent Contact: (917) 363-5414 Office Contact: (203) 655-8238

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 19 Chester Rd

School District:Darien School District
NameGradesDistance
Holmes Elementary School, Darien, CT
18 Hoyt Street, Darien, CT 06820
K-50.4 mi
Middlesex Middle School
204 Hollow Tree Ridge Road, Darien, CT 06820
6-80.5 mi
Darien High School
80 High School Lane, Darien, CT 06820
9-121 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 19 Chester Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/05/2026
Listed
$2,225,000
69.2%
MLS
8/17/2012
Sold
$1,315,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 19 Chester Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$18,247
5%
$1,178,730
—
2023
$17,316
16%
$1,178,730
39%
2023
$14,961
2%
$849,590
—
2022
$14,638
2%
$849,590
—
2021
$14,307
3%
$849,590
—
2020
$13,874
-1%
$849,590
—
2019
$13,993
2%
$849,590
—
2018
$13,713
—
$852,810
—
2017
$13,781
2%
$852,810
—
2016
$13,449
3%
$852,810
—
2015
$13,091
2%
$852,810
—
2014
$12,801
4%
$852,810
-9%
2012
$12,341
—
$937,020
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 19 Chester Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Houlihan Lawrence, Heather Hilleman

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19 Chester Road, Darien, CT 06820 (MLS# 24170445) is a Single Family property with 4 bedrooms, 2 full bathrooms and 1 partial bathroom. 19 Chester Road is currently listed for $2,225,000 and was received on May 01, 2026. Want to learn more about 19 Chester Road? Do you have questions about finding other Single Family real estate for sale in Darien? You can browse all Darien real estate or contact a Coldwell Banker agent to request more information.

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