256 Country Club Road
New Canaan, Connecticut 06840
- Beds
- 5
- Baths
- 7 | 2
- SqFt
- 9,473
- Acres
- 2.75
- Year Built
- 1999
- Neighborhood
- Oenoke Ridge
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Set just four minutes from town on nearly three acres adjacent to protected Land Trust property, this exceptional residence offers the privacy, scale, and tranquility of a country estate without sacrificing convenience. Sprawling lawns, stone walls, and a fully finished pool house with pool accessed through a dramatic hornbeam archway, underscore the property's exceptional outdoor living experience. The entry foyer establishes the home's architectural character, unfolding into a generous front to back gallery anchored by mahogany doors that open directly to the 33 foot covered porch and outdoor terrace. Detailed millwork, oak floors, and beautifully proportioned rooms create a sense of continuity throughout, while French doors across the principal living spaces provide a seamless connection between indoor and outdoor living. The kitchen, family room, and informal dining area are thoughtfully arranged in an open, flowing layout oriented toward the grounds, balancing everyday comfort with effortless entertaining. A well appointed mudroom serves the practical demands of daily life with equal attention to detail. The primary suite is distinguished by soaring 12 foot ceilings and dual walk in closets. Four additional en suite bedrooms, a substantial bonus room, and a third floor guest suite/lounge complete the upper levels. The lower level is finished with a generous recreation space, half bath, media room, and a gaming room that walks out to a private terrace.
Key Facts
- City/Town
- New Canaan
- Neighborhood
- Oenoke Ridge
- Property / Style
- Single Family · Colonial
- Year Built
- 1999
- Days on Market
- 56 days
- Beds
- 5
- Baths
- 7 full · 2 half
- Living Area
- 9,473 sq ft
- Lot Size
- 2.75 acres
- Garage / Parking
- 5 garage
- Property Taxes
- $45,540 / Annually
Market Snapshot
The New Canaan Market
Single Family · trailing 12 months
Active Listings
34
51 under contract
Median List Price
$3.02M
34 active listings
Median Closed Price
$2.74M
212 sales
Median Days on Market
41
34 active listings
Median $ / Sq Ft
$658
34 active listings
Sale-to-List Ratio
100.6%
212 sales
How this home compares
List Price
$7.15M
vs $3.02M median
2.4× the median
Price / Sq Ft
$755
vs $658 median
14.7% above median
Days on Market
56 days
vs 41 days median
15 days longer than median
Based on 34 active and 212 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of July 27, 2026.
Location
256 Country Club Road, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$36,456
- Property Taxes$3,795
- Insurance$2,383
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- New Canaan
- Neighborhood
- Oenoke Ridge
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1999
- New Construction
- No/Resale
- Living Area
- 9,473 sq ft
- Below Grade
- 1,546 sq ft
Schools
- Elementary
- West
- High
- New Canaan
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 4
- Laundry
- Upper Level
- Laundry Location
- Second Floor Hall
- Appliances
- Gas RangeOven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryerWine Chiller
- Basement
- FullHeatedStorageCooledPartially FinishedWalk-outLiveable Space
- In-Law Apartment
- PossibleDetached
- Interior Features
- Audio SystemAuto Garage Door OpenerOpen Floor PlanSecurity System
- Additional Rooms
- Bonus RoomExercise RoomFoyerMud Room
Exterior & Lot
- Lot Size
- 2.75 acres
- Zoning
- 2AC
- Garage / Parking
- 5 garage spacesAttached GarageDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Pool
- GuniteHeatedPool HouseIn Ground Pool
- Construction
- Clapboard
- Color
- White
- Roof
- Wood Shingle
- Foundation
- Concrete
- Exterior Features
- TerracePorchGuttersLightingGuest HouseFrench DoorsUnderground SprinklerPatio
- Lot Description
- Open Lot
Listing & Financials
- Property Taxes
- $45,540 / Annually
- Days on Market
- 56
- MLS #
- 24178654
- MLS Status
- Under Contract
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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 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 7:25 AM UTC.