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248 Turtle Back RoadNew Canaan, CT 06840

For Sale

$3,625,000

Smart Buyer Rebate $36,250

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.

Listed by John Dunn

·

Compass Connecticut, LLC

·

(203) 388-5353

Last updated October 24, 2026

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Source: SmartMLS #24178727

Listing Facts

  • TypeSingle-family
  • NeighborhoodNew Canaan
  • Bedrooms5
  • Bathrooms6
  • Days on Prevu53
  • Taxes$23,070/year
  • Size5,291 sqft
  • Price per sqft$685

Location

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Listing History

10/21/2026
Price Decreased
$3,625,000
09/10/2026
Status changed to Active
$4,000,000
09/08/2026
Listed by Compass Connecticut, LLC
$4,000,000
  1. 10/21/2026$3,625,000
    Price Decreased
  2. 09/10/2026$4,000,000
    Status changed to Active
  3. 09/08/2026$4,000,000
    Listed by Compass Connecticut, LLC

Property Details for 248 Turtle Back Road

Exterior

Construction

  • New Construction: No/Resale
  • Roof: Metal
  • Year Built: 1963
  • Year Built Details: Public Records
  • Architectural Style: Colonial
  • Construction Materials: Frame

Features

  • Waterfront Features: Not Applicable

Measurements

  • Lot Features: Fence - Partial, Level Lot, Professionally Landscaped
  • Lot Size Acres: 3.41

Financial

Taxes

  • Parcel Number: 184797
  • Tax Annual Amount: $23,070.00
  • Tax Year: 26

Interior

Features

  • Appliances: Gas Cooktop, Oven/Range, Refrigerator, Subzero, Dishwasher, Washer, Dryer
  • Fireplaces Total: 3

Measurements

  • Living Area: 4,191

Rooms

  • Basement: Full, Heated, Fully Finished, Cooled, Liveable Space, Full With Walk-Out
  • Bathrooms Full: 5
  • Bathrooms Half: 1
  • Bathrooms Total Integer: 6
  • Bedrooms Total: 5
  • Rooms Total: 10

Parking

Parking

  • Attached Garage: Attached Garage, Detached Garage
  • Garage Spaces: 5

Schools

Elementary School

  • Elementary School: West

High School

  • High School: New Canaan

Middle or Junior School

  • Middle Or Junior School: Saxe Middle

Utilities

Equipment

  • Cooling: Central Air
  • Heating: Hot Water
  • Laundry Features: Main Level
  • Sewer: Septic
  • Water Source: Private Well

Frequently Asked Questions

How many bedrooms and bathrooms does this single-family home have?

There are 5 bedrooms and 6 bathrooms in this single-family home at 248 Turtle Back Road.

What schools are nearby to 248 Turtle Back Road?

Nearby schools include the West Elementary School, Saxe Middle, and New Canaan High School.

Does this single-family home have parking?

Yes, there are 5 parking spaces available for 248 Turtle Back Road.

What are the annual taxes for 248 Turtle Back Road?

Annual taxes for this single-family home are estimated at $23,070.

How does 248 Turtle Back Road compare to other single-family homes in New Canaan?

This single-family home is listed 17% below the average price for single-family homes in New Canaan and has been on the market for 59 less days than the typical home in this area.

What is the square footage on this single-family home?

According to the MLS, this listing is 5,291 sqft.

248 Turtle Back Road is a 5-bedroom, 6-bath single-family home for sale in New Canaan CT 06840. On Prevu for 53 days at $3,625,000. This includes a recent price decrease of $375,000. This property features 5,291 square feet of living space, located in New Canaan. The median listing price for single-family homes in this area is $2,800,000. Nearby schools include West Elementary School, Saxe Middle, and New Canaan High School. View other single-family home listings in Fairfield County.

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Full MLS Disclaimers

Rebate estimate is indicative only and based on listing price and estimated buyer's agent commission paid by owner, if applicable. Final rebates are subject to Terms of Use and may vary due to final negotiated transaction terms.