248 Turtle Back Road
New Canaan, Connecticut 06840
Reduced from $4,000,000
- 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
Classic New England architecture, beautifully proportioned interiors and exceptional privacy come together at 248 Turtle Back Road, a distinguished five-bedroom Colonial offering 5,291 square feet of living space in one of New Canaan's most desirable settings. Inside, the home is filled with warmth, character and natural light. The impressive great room features a vaulted beamed ceiling, creating a dramatic yet inviting space for everyday living and entertaining. An eat-in kitchen with center island, generous cabinetry and French doors is complemented by a dining room overlooking the gorgeous backyard, family room and den, providing both open gathering spaces and quieter places to retreat. Upstairs, the primary suite offers a private dressing room and en-suite bath, joined by three additional bedrooms, including an en-suite guest room. The fully finished walk-out lower level significantly expands the home's versatility with an additional bedroom and full bath, sunroom with wet bar, recreation room, office and exercise space. Outside, the home is set on 3.41 beautifully landscaped acres, where specimen plantings, mature trees, stone walls and terraces create a remarkable sense of privacy and established beauty. A circular drive, greenhouse and garage parking for 5 complete the property. Set just minutes from the heart of New Canaan, 248 Turtle Back Road pairs substantial, character-filled interiors with the privacy and scale that are rare to find this close to town.
Key Facts
- City/Town
- New Canaan
- Neighborhood
- N/A
- Property / Style
- Single Family · Colonial
- Year Built
- 1963
- Days on Market
- 65 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
35
23 under contract
Median List Price
$3.69M
35 active listings
Median Closed Price
$2.81M
211 sales
Median Days on Market
63
35 active listings
Median $ / Sq Ft
$673
35 active listings
Sale-to-List Ratio
102.2%
211 sales
How this home compares
List Price
$3.63M
vs $3.69M median
In line with median
Price / Sq Ft
$685
vs $673 median
In line with median
Days on Market
65 days
vs 63 days median
In line with median
Based on 35 active and 211 closed sales (trailing 12 mo) of single family in New Canaan. Source: SmartMLS · As of November 12, 2026.
Location
248 Turtle Back Road, New Canaan, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$19,646
- Property Taxes$1,923
- Insurance$1,208
- 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
- 65
- MLS #
- 24178727
- MLS Status
- Active
Similar Properties
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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 11/12/2026. 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 11/12/2026 at 10:46 PM UTC.