19 Chester Road
Darien, Connecticut 06820
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 3,264
- Acres
- 0.50
- Year Built
- 1931
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
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About 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.
Key Facts
- City/Town
- Darien
- Neighborhood
- N/A
- Property / Style
- Single Family · Tudor
- Year Built
- 1931
- Days on Market
- 87 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 3,264 sq ft
- Lot Size
- 0.50 acres
- Garage / Parking
- 4 total
- Property Taxes
- $18,247 / Annually
Market Snapshot
The Darien Market
Single Family · trailing 12 months
Active Listings
24
54 under contract
Median List Price
$3.85M
24 active listings
Median Closed Price
$2.71M
212 sales
Median Days on Market
53
24 active listings
Median $ / Sq Ft
$707
24 active listings
Sale-to-List Ratio
106.3%
212 sales
How this home compares
List Price
$2.23M
vs $3.85M median
42.2% below median
Price / Sq Ft
$682
vs $707 median
In line with median
Days on Market
87 days
vs 53 days median
34 days longer than median
Based on 24 active and 212 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of July 27, 2026.
Location
19 Chester Road, Darien, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$11,345
- Property Taxes$1,521
- Insurance$742
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Darien
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Tudor
- Year Built
- 1931
- New Construction
- No/Resale
- Living Area
- 3,264 sq ft
Schools
- Elementary
- Holmes
- High
- Darien
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Gas CooktopWall OvenMicrowaveRange HoodSubzeroDishwasherWasherDryer
- Basement
- FullUnfinished
- In-Law Apartment
- No
Exterior & Lot
- Lot Size
- 0.50 acres
- Zoning
- R13
- Garage / Parking
- 4 total parking spacesDrivewayGravel
- Waterfront Details
- Beach Rights
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- ShingleBrick
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Porch-ScreenedShedPorchPatio
- Lot Description
- Borders Open SpaceLevel LotOn Cul-De-SacProfessionally Landscaped
Listing & Financials
- Property Taxes
- $18,247 / Annually
- Days on Market
- 87
- MLS #
- 24170445
- MLS Status
- Under Contract
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/27/2026 at 10:40 PM UTC.