505 Country Club Road
New Canaan, Connecticut 06840
- Beds
- 6
- Baths
- 6 | 3
- SqFt
- 11,607
- Acres
- 4.00
- Year Built
- 2008
- Property Type
- Single Family
Matt Caiola
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About This Home
Custom built in 2009 for this site and held by one family since, this New Canaan estate sits on four private acres with a pond, a gunite pool and wooded land that continues beyond the lawn. Three levels and 8,942 square feet above grade are finished with custom millwork and Venetian plaster, and a geothermal system heats and cools the entire house. The kitchen, family room, pantry and office were rebuilt together in 2018 and open to the way a household actually gathers. Seven fireplaces warm the interior and an eighth anchors the patio. Six en suite bedrooms, six full and three half baths, a second-floor laundry room and a cedar closet make the upper floors easy to live in. The lower level runs at full ceiling height with a media room, gym, bar, wine closet and fireplace. Nearly 1,800 square feet of open porch and flagstone terraces extend the main rooms outdoors. The pool house has a cathedral ceiling, a full bath, a kitchen and a grill, and an outdoor shower which makes the pool area a self-contained retreat. New Canaan is widely considered the most beautifully preserved New England town within one hour of New York City. Boutiques, fine dining, outstanding schools and services gather in one walkable village center, with the residential community radiating outward in quiet, leafy tranquility.
Key Facts
- City/Town
- New Canaan
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial,Other
- Year Built
- 2008
- Days on Market
- 2 days
- Beds
- 6
- Baths
- 6 full · 3 half
- Living Area
- 11,607 sq ft
- Lot Size
- 4.00 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $55,143 / Annually
Market Snapshot
The New Canaan Market
Single Family · trailing 12 months
Active Listings
35
21 under contract
Median List Price
$3.63M
35 active listings
Median Closed Price
$2.83M
210 sales
Median Days on Market
55
35 active listings
Median $ / Sq Ft
$658
35 active listings
Sale-to-List Ratio
102.2%
210 sales
How this home compares
List Price
$6.50M
vs $3.63M median
79.2% above median
Price / Sq Ft
$560
vs $658 median
14.9% below median
Days on Market
2 days
vs 55 days median
53 days fresher than median
Based on 35 active and 210 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of November 2, 2026.
Location
505 Country Club Road, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$35,411
- Property Taxes$4,595
- Insurance$2,165
- 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,Other
- Year Built
- 2008
- New Construction
- No/Resale
- Living Area
- 11,607 sq ft
- Below Grade
- 2,665 sq ft
Schools
- Elementary
- West
- High
- New Canaan
Interior
- Heating
- Other
- Cooling
- Zoned
- Fireplaces
- 7
- Laundry
- Lower LevelUpper Level
- Laundry Location
- Main floor and second floor
- Appliances
- Gas CooktopWall OvenMicrowaveRange HoodRefrigeratorFreezerSubzeroDishwasherWasherDryerWine Chiller
- Basement
- FullHeatedCooledInterior AccessPartially FinishedWalk-outLiveable Space
- Interior Features
- Audio SystemAuto Garage Door OpenerCable - Pre-wiredSecurity System
Exterior & Lot
- Lot Size
- 4.00 acres
- Zoning
- 4AC
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront
- Direct waterfront
- Waterfront Details
- PondWalk to WaterView
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedPool HouseSpaIn Ground Pool
- Construction
- Shingle
- Color
- gray
- Roof
- Wood Shingle
- Foundation
- Concrete
- Exterior Features
- TerracePorchGuttersFrench DoorsUnderground Sprinkler
- Lot Description
- Professionally Landscaped
Listing & Financials
- Property Taxes
- $55,143 / Annually
- Days on Market
- 2
- MLS #
- 24191769
- MLS Status
- Coming Soon
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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 11/2/2026. 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 11/2/2026 at 4:30 PM UTC.