248 Turtle Back Road
New Canaan, Connecticut 06840
- Beds
- 5
- Baths
- 5 | 1
- SqFt
- 5,291
- Acres
- 3.41
- Year Built
- 1963
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
30
20 under contract
Median List Price
$3.27M
30 active listings
Median Closed Price
$2.80M
212 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 3, 2026per 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
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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 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.