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234 Brookside Road

Darien, Connecticut 06820

PENDING$4,750,000
Beds
6
Baths
6 | 1
SqFt
6,829
Acres
1.40
Year Built
1937
Matt Caiola

Matt Caiola

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Pool3-Car Garage6 FireplacesVirtual Tour

About This Home

Set along a picturesque stretch in one of Darien's most sought-after neighborhoods, 234 Brookside Road offers a rare blend of timeless architecture, privacy, and modern comfort. Surrounded by mature trees and beautifully landscaped grounds, this exceptional property provides a serene, retreat-like setting just minutes from town, top-rated schools, and the coastline. This HOBI award-winning residence welcomes you with a gracious entry that opens into expansive, light-filled interiors designed for both elegance and ease. A thoughtfully planned, free-flowing layout connects formal living and dining rooms-ideal for entertaining-with inviting casual spaces suited to everyday living. The well-appointed kitchen serves as the heart of the home, featuring high-end appliances and seamless flow to family gathering areas and outdoor living spaces. Upstairs, the tranquil primary suite features a vaulted ceiling, dual walk-in closets, and a spacious spa-inspired bath. Each of the four additional bedrooms offers an en suite bath, ensuring comfort and privacy for family and guests. Complementing the approximately 5,700-square-foot main house is a fully equipped 1,100-square-foot guest house with living and dining areas, a full kitchen, a wood-burning fireplace, and a private suite with a full bathroom. Set on 1.4 level acres, the outdoor spaces include a gunite pool and spa, outdoor kitchen, and fireplace-perfect for entertaining or relaxing in complete privacy year-round.

Key Facts

City/Town
Darien
Neighborhood
N/A
Property / Style
Single Family · Cape Cod
Year Built
1937
Days on Market
110 days
Beds
6
Baths
6 full · 1 half
Living Area
6,829 sq ft
Lot Size
1.40 acres
Garage / Parking
3 garage
Property Taxes
$33,904 / Annually

Market Snapshot

The Darien Market

Single Family · trailing 12 months

Median Days on Market

51

25 active listings

Median $ / Sq Ft

$733

25 active listings

Sale-to-List Ratio

106.3%

211 sales

How this home compares

List Price

$4.75M

vs $3.80M median

25.0% above median

Price / Sq Ft

$696

vs $733 median

5.0% below median

Days on Market

110 days

vs 51 days median

59 days longer than median

Based on 25 active and 211 closed sales (trailing 12 mo) of single family in Darien. Source: SmartMLS · As of July 27, 2026.

Location

234 Brookside Road, Darien, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$28,627

per month

  • Principal & Interest$24,219
  • Property Taxes$2,825
  • Insurance$1,583
  • 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
Cape Cod
Year Built
1937
New Construction
No/Resale
Living Area
6,829 sq ft

Schools

Elementary
Ox Ridge
High
Darien

Interior

Heating
Hydro AirZoned
Heat Fuel
Propane
Cooling
Central Air
Fireplaces
6
Laundry
Upper Level
Appliances
Gas CooktopWall OvenMicrowaveRefrigeratorFreezerDishwasherWasherDryerWine Chiller
Basement
FullUnfinished
In-Law Apartment
YesDetached
Interior Features
Auto Garage Door Opener

Exterior & Lot

Lot Size
1.40 acres
Zoning
R2
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Flood Zone
No
Pool
GuniteHeatedSpaIn Ground Pool
Construction
Clapboard
Roof
Asphalt Shingle
Foundation
Masonry
Lot Description
Level LotProfessionally Landscaped

Listing & Financials

Property Taxes
$33,904 / Annually
Days on Market
110
MLS #
24164395
MLS Status
Under Contract

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Kristin Nemec

(203) 829-8998

William Pitt Sotheby's Int'l

(203) 655-8234

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 12:31 PM UTC.