Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$2,225,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 1 Partial Bath
  • 3,264 Sq. Ft.
  • Updated 6 hours ago

Next open house:

Open House: 1:00 PM - 3:00 PM

Saturday 5/9 1:00 PM - 3:00 PM

19 Chester Road,Darien, CT 06820

19 Chester RoadDarienCT06820

Get directions
See This Home
Save This Home
See This Home
Save This Home
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: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24170445
  • Updated: Today (5/5/2026)
  • Added to Site: Today

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

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

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

$
Down Payment
%
$
%

$
$

*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

Get Pre-Approved

Listed by Houlihan Lawrence, Heather Hilleman

Similar Properties near 19 Chester Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

33 Fairview Ave, Darien, CT 06820 - Photo 1 Just Listed
$2,395,000

33 Fairview Ave  Darien, CT 06820

  • Single Family
  • Active
  • Updated 1 day ago
  • 4
    Beds
  • 3
    Total Baths
  • 3,102
    Sq. Ft.
Listed by Compass Connecticut, LLC
39 Wedgemere Rd, Stamford, CT 06905 - Photo 1
$2,395,000

39 Wedgemere Rd  Stamford, CT 06905

  • Single Family
  • Active
  • 4
    Beds
  • 4
    Total Baths
  • 6,920
    Sq. Ft.
Listed by Houlihan Lawrence
61 Hobson St, Stamford, CT 06902 - Photo 1
$2,160,000

61 Hobson St  Stamford, CT 06902

  • Single Family
  • Active
  • 5
    Beds
  • 4
    Total Baths
  • 3,644
    Sq. Ft.
Listed by William Raveis Real Estate
20 Roton Ave, Norwalk, CT 06853 - Photo 1 Just Listed
$2,450,000

20 Roton Ave  Norwalk, CT 06853

  • Single Family
  • Active
  • Updated 6 hours ago
  • 4
    Beds
  • 5
    Total Baths
  • 4,006
    Sq. Ft.
Listed by William Raveis Real Estate

Just Listed near 19 Chester Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

128 1/2 Ponus Ave, Norwalk, CT 06850 - Photo 1 Just Listed
$375,000

128 1/2 Ponus Ave  Norwalk, CT 06850

  • Land Residential
  • Active
  • Updated 2 days ago
  • 0.8
    Acres
Listed by Kelly Higgins Team (203) 650-3483
48 Dean St, Stamford, CT 06902 - Photo 1 Just Listed
$399,000

48 Dean St  #4  Stamford, CT 06902

  • Townhouse
  • Active
  • Updated 5 days ago
  • 2
    Beds
  • 2
    Total Baths
  • 1,038
    Sq. Ft.
Listed by Aaron Goldberg (203) 561-0362
20 Brushwood Rd, Stamford, CT 06903 - Photo 1 Just Listed
$1,850,000

20 Brushwood Rd  Stamford, CT 06903

  • Single Family
  • Active
  • Updated 2 days ago
  • 6
    Beds
  • 4
    Total Baths
  • 4,716
    Sq. Ft.
Listed by Barbara Zaccagnini (203) 618-0172 and Coldwell Banker Realty
1458 Bedford St, Stamford, CT 06905 - Photo 1 Just Listed
$12,000

1458 Bedford St  Stamford, CT 06905

  • Commercial Lease
  • Active
Listed by The Rosato Team (203) 622-4000

Price Reduced near 19 Chester Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

1016 Long Ridge Rd, Stamford, CT 06903 - Photo 1 Price Reduced
-$100,000 (-9.1%)
$999,000

1016 Long Ridge Rd  Stamford, CT 06903

  • Single Family
  • Active
  • Updated 5 days ago
  • 6
    Beds
  • 4
    Total Baths
  • 3,585
    Sq. Ft.
Listed by Alpha Capital Realty, LLC
9 Sylvester Ct, Norwalk, CT 06855 - Photo 1 Price Reduced
-$100,000 (-2.64%)
$3,695,000

9 Sylvester Ct  Norwalk, CT 06855

  • Single Family
  • Active
  • Updated 1 day ago
  • 5
    Beds
  • 4
    Total Baths
  • 4,241
    Sq. Ft.
Listed by William Raveis Real Estate
49 Spring Hill Ln N, Stamford, CT 06903 - Photo 1 Price Reduced
-$75,000 (-5.26%)
$1,350,000

49 Spring Hill Ln N  Stamford, CT 06903

  • Single Family
  • Active
  • Updated 8 minutes ago
  • 4
    Beds
  • 4
    Total Baths
  • 4,324
    Sq. Ft.
Listed by Keller Williams Prestige Prop.
17 Reservoir Ave, Norwalk, CT 06850 - Photo 1 Price Reduced
-$100,000 (-12.52%)
$699,000

17 Reservoir Ave  Norwalk, CT 06850

  • Single Family
  • Active
  • Updated 4 days ago
  • 4
    Beds
  • 2
    Total Baths
  • 948
    Sq. Ft.
Listed by BHGRE Shore & Country

Recent Sales near 19 Chester Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

76 Deepwood Rd, Darien, CT 06820 - Photo 1 Sold
$2,287,500

76 Deepwood Rd  Darien, CT 06820

  • Single Family
  • Closed
  • 5
    Beds
  • 4
    Total Baths
  • 3,897
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by Houlihan Lawrence
76 Deepwood Rd, Darien, CT 06820 - Photo 1 Sold
$2,287,500

76 Deepwood Rd  Darien, CT 06820

  • Land Residential
  • Closed
  • 1.01
    Acres
Listed by William Pitt Sotheby's Int'l
Sold by Houlihan Lawrence
19 Anthony Ln, Darien, CT 06820 - Photo 1 Sold
$2,054,000

19 Anthony Ln  Darien, CT 06820

  • Single Family
  • Closed
  • 4
    Beds
  • 3
    Total Baths
  • 2,400
    Sq. Ft.
Listed by Houlihan Lawrence
Sold by Compass Connecticut, LLC
3 Revere Rd, Darien, CT 06820 - Photo 1 Sold
$2,350,000

3 Revere Rd  Darien, CT 06820

  • Single Family
  • Closed
  • Updated 3 days ago
  • 5
    Beds
  • 3
    Total Baths
  • 3,395
    Sq. Ft.
Listed by Compass Connecticut, LLC
Sold by William Raveis Real Estate

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 05, 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.

Tour this property