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248 Turtle Back Road

New Canaan, Connecticut 06840

ACTIVE$3,625,000

Reduced from $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 FireplacesPrice Reduced

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$22,777

per 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

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 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.