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523 Brookside Road

New Canaan, Connecticut 06840

ACTIVE - NEW$1,995,000
Beds
5
Baths
3 | 1
SqFt
3,286
Acres
2.59
Year Built
1959
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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2-Car Garage2 Fireplaces

About This Home

Nestled at the end of a long private drive south of the Merritt Parkway, this classic Colonial offers timeless character, generous living space, and a highly convenient location. Beautifully expanded and thoughtfully updated 15 years ago, the home showcases exceptional craftsmanship, enduring quality, and solid construction described as having "great bones." The main level is rich with architectural detail - an elegant front-to-back Living Room with fireplace and exquisite custom built-in cabinetry and the Dining Room with beautiful built-in details. At the heart of the home is an expansive Kitchen featuring high-end appliances, custom built-ins, and a second fireplace in the casual dining area-an inviting space for morning coffee, relaxed meals, or entertaining. The adjacent light-filled Family Room offers beautiful views of the changing seasons and provides a comfortable extension of the main living areas. The house includes four spacious bedrooms and 2.5 baths, while a private suite above the garage adds a fifth bedroom with full bath, offering flexibility for guests, a private office or additional living space. Finished recreational space on the lower level provides room to work, play, exercise and the generous terrace creates an inviting setting for outdoor dining and entertaining. With its distinctive architecture, thoughtful layout, and quality details, the home offers an exceptional foundation for personalization, including some cosmetic updating to the exterior.

Key Facts

City/Town
New Canaan
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1959
Days on Market
0 days
Beds
5
Baths
3 full · 1 half
Living Area
3,286 sq ft
Lot Size
2.59 acres
Garage / Parking
2 garage
Property Taxes
$21,324 / Annually

Market Snapshot

The New Canaan Market

Single Family · trailing 12 months

Median Days on Market

60

31 active listings

Median $ / Sq Ft

$676

31 active listings

Sale-to-List Ratio

102.2%

212 sales

How this home compares

List Price

$2.00M

vs $3.05M median

34.6% below median

Price / Sq Ft

$607

vs $676 median

10.2% below median

Days on Market

0 days

vs 60 days median

60 days fresher than median

Based on 31 active and 212 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of September 8, 2026.

Location

523 Brookside Road, New Canaan, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$12,751

per month

  • Principal & Interest$10,309
  • Property Taxes$1,777
  • Insurance$665
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
New Canaan
Neighborhood
N/A
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
1959
New Construction
No/Resale
Living Area
3,286 sq ft
Below Grade
300 sq ft

Schools

Elementary
South
High
New Canaan

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
2
Laundry
Lower Level
Appliances
Gas RangeRange HoodSubzeroDishwasherWasherDryer
Basement
FullPartially Finished
Interior Features
Security System

Exterior & Lot

Lot Size
2.59 acres
Zoning
1AC
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
Shingle
Color
Taupe
Roof
Wood Shingle
Foundation
BlockConcrete
Exterior Features
Terrace
Lot Description
Rear LotLightly WoodedProfessionally Landscaped

Listing & Financials

Property Taxes
$21,324 / Annually
Days on Market
0
MLS #
24201426
MLS Status
Active

Similar Properties

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Listed By

Lisa O'rourke

(203) 326-0532

William Pitt Sotheby's Int'l

(203) 966-2633

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/8/2026. 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 9/8/2026 at 6:10 PM UTC.