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248 Turtle Back Road

New Canaan, Connecticut 06840

COMING SOON - NEW$4,000,000
Beds
5
Baths
5 | 1
SqFt
5,291
Acres
3.41
Year Built
1963
Matt Caiola

Matt Caiola

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5-Car Garage3 Fireplaces

About This Home

Welcome to a property where a collector's garden of Japanese maples, rhododendrons, and azaleas - in every shade from gold to crimson to blush pink - announces something extraordinary before you've even reached the front door. A circular drive leads to this classic New England white Colonial, set on nearly three and a half acres on prestigious Turtle Back Road, where grounds shaped with the care of a private arboretum unfold: flagstone terraces, fieldstone walls, and specimen plantings set against a canopy of mature trees. From its copper roof to its storied gardens, every element of this five-bedroom, six-bath New Canaan property feels distinctive. With nearly 5,200 square feet of living space, the home offers generous accommodations while maintaining real warmth and character. Positioned to embrace its surroundings, sun-filled interiors and tranquil views from nearly every room create a seamless connection between indoors and out. Whether entertaining on a grand scale or savoring the simple pleasures of everyday life, the property offers a rare sense of space, comfort, and retreat. Just minutes from the heart of New Canaan, this exceptional home provides easy access to downtown amenities, award-winning schools, parks, and Metro-North - while feeling worlds away from it all. Seldom does a property offer such a rare combination of privacy, beauty, and one of Fairfield County's most sought-after addresses.

Key Facts

City/Town
New Canaan
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1963
Days on Market
0 days
Beds
5
Baths
5 full · 1 half
Living Area
5,291 sq ft
Lot Size
3.41 acres
Garage / Parking
5 garage
Property Taxes
$23,070 / Annually

Market Snapshot

The New Canaan Market

Single Family · trailing 12 months

Median Days on Market

61

30 active listings

Median $ / Sq Ft

$678

30 active listings

Sale-to-List Ratio

102.2%

212 sales

How this home compares

List Price

$4.00M

vs $3.27M median

22.2% above median

Price / Sq Ft

$756

vs $678 median

11.5% above median

Days on Market

0 days

vs 61 days median

61 days fresher than median

Based on 30 active and 212 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of September 8, 2026.

Location

248 Turtle Back Road, New Canaan, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$23,926

per month

  • Principal & Interest$20,670
  • Property Taxes$1,923
  • Insurance$1,333
  • 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
1963
New Construction
No/Resale
Living Area
5,291 sq ft
Below Grade
1,100 sq ft

Schools

Elementary
West
High
New Canaan

Interior

Heating
Hot Water
Heat Fuel
OilPropane
Cooling
Central Air
Fireplaces
3
Laundry
Main Level
Appliances
Gas CooktopOven/RangeRefrigeratorSubzeroDishwasherWasherDryer
Basement
FullHeatedFully FinishedCooledLiveable SpaceFull With Walk-Out
Additional Rooms
Exercise RoomFoyerGreenhouseSteam/SaunaSitting Room

Exterior & Lot

Lot Size
3.41 acres
Zoning
4AC
Garage / Parking
5 garage spacesAttached GarageDetached Garage
Waterfront Details
Not Applicable
Water Source
Private Well
Sewer
Septic
Construction
ClapboardWood
Roof
Metal
Foundation
Concrete
Lot Description
Fence - PartialLevel LotProfessionally Landscaped

Listing & Financials

Property Taxes
$23,070 / Annually
Days on Market
0
MLS #
24178727
MLS Status
Coming Soon

Similar Properties

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

Listed By

John Dunn

(203) 388-5353

Compass Connecticut, LLC

(203) 442-6626

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/8/2026. 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 9/8/2026 at 9:01 AM UTC.