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256 Country Club Road

New Canaan, Connecticut 06840

PENDING$7,150,000
Beds
5
Baths
7 | 2
SqFt
9,473
Acres
2.75
Year Built
1999
Matt Caiola

Matt Caiola

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Guest HousePool5-Car Garage4 Fireplaces

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

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$42,634

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Christine Saxe

(203) 273-1548

Compass Connecticut, LLC

(203) 442-6626

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.