474 Brookside Road
New Canaan, Connecticut 06840
- Beds
- 6
- Baths
- 4 | 1
- SqFt
- 7,723
- Acres
- 3.11
- Year Built
- 1932
- Property Type
- Single Family
Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
A truly exceptional private estate, this country compound set on more than three private acres, blends timeless character, refined design, and modern luxury. Anchored by a beautifully preserved 1932 main residence and an extraordinary 2,300-square-foot poolside entertainment barn, the property is designed for both everyday living and effortless entertaining. The main residence offers five bedrooms and three full baths, including a luxurious primary suite with spa-like bath, expansive walk-in closet, and private deck overlooking the grounds. Gracious formal living and dining rooms complement a chef's kitchen opening to the family room and breakfast area. A finished lower level provides additional living and entertaining space. The poolside barn is a destination unto itself, with a dramatic Great room, wet bar and kitchenette, private gym, home office, full bath, and outdoor shower. Expansive lawns, perennial gardens, multiple outdoor fireplaces, a spectacular swimming pool, and gracious dining veranda complete the grounds. Distinct living and entertaining spaces flow effortlessly together, creating an experience like no other.
Key Facts
- City/Town
- New Canaan
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1932
- Days on Market
- 0 days
- Beds
- 6
- Baths
- 4 full · 1 half
- Living Area
- 7,723 sq ft
- Lot Size
- 3.11 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $33,075 / Annually
Market Snapshot
The New Canaan Market
Single Family · trailing 12 months
Active Listings
36
21 under contract
Median List Price
$3.25M
36 active listings
Median Closed Price
$2.80M
212 sales
Median Days on Market
49
36 active listings
Median $ / Sq Ft
$678
36 active listings
Sale-to-List Ratio
102.2%
212 sales
How this home compares
List Price
$5.89M
vs $3.25M median
81.5% above median
Price / Sq Ft
$763
vs $678 median
12.5% above median
Days on Market
0 days
vs 49 days median
49 days fresher than median
Based on 36 active and 212 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of September 10, 2026.
Location
474 Brookside Road, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$30,619
- Property Taxes$2,756
- Insurance$1,965
- 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
- 1932
- New Construction
- No/Resale
- Living Area
- 7,723 sq ft
- Below Grade
- 624 sq ft
Schools
- Elementary
- South
- High
- New Canaan
Interior
- Heating
- Hot Water
- Heat Fuel
- Propane
- Cooling
- Central Air
- Fireplaces
- 5
- Laundry
- Upper Level
- Laundry Location
- Second Floor/2nd Pool Laundry in Barn
- Appliances
- Gas RangeMicrowaveRange HoodSubzeroDishwasher
- Basement
- FullFully Finished
- In-Law Apartment
- PossibleDetached
- Interior Features
- Audio SystemCable - AvailableSecurity System
- Additional Rooms
- Bonus RoomFoyerGymMud Room
Exterior & Lot
- Lot Size
- 3.11 acres
- Zoning
- 2AC
- Garage / Parking
- 2 garage spacesDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- HeatedPool HouseIn Ground Pool
- Construction
- Shingle
- Roof
- Shingle
- Foundation
- Masonry
- Exterior Features
- Terrace
- Lot Description
- Level LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $33,075 / Annually
- Days on Market
- 0
- MLS #
- 24196978
- MLS Status
- Coming Soon
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Nikki Glazer
Compass Connecticut, LLC
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/10/2026. 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 9/10/2026 at 5:20 PM UTC.