523 Brookside Road
New Canaan, Connecticut 06840
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 3,286
- Acres
- 2.59
- Year Built
- 1959
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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 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
- 61 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
Active Listings
32
24 under contract
Median List Price
$3.85M
32 active listings
Median Closed Price
$2.81M
210 sales
Median Days on Market
61
32 active listings
Median $ / Sq Ft
$677
32 active listings
Sale-to-List Ratio
102.4%
210 sales
How this home compares
List Price
$2.00M
vs $3.85M median
48.1% below median
Price / Sq Ft
$607
vs $677 median
10.3% below median
Days on Market
61 days
vs 61 days median
In line with median
Based on 32 active and 210 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of November 8, 2026.
Location
523 Brookside Road, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$10,812
- 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
- Asphalt Shingle
- Foundation
- BlockConcrete
- Exterior Features
- Terrace
- Lot Description
- Rear LotLightly WoodedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $21,324 / Annually
- Days on Market
- 61
- MLS #
- 24201426
- 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 11/8/2026. 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 11/8/2026 at 8:50 AM UTC.