New Canaan, CT / 8 DAYS ON MARKET

248 Turtle Back RoadNew Canaan, CT 06840

Asking price$4,000,000Active

Our Take

248 Turtle Back Road in New Canaan is a 1963 white Colonial with five bedrooms and five full and one half bath on 3.41 acres. A circular drive leads through grounds with Japanese maples, rhododendrons, azaleas, specimen plantings, mature trees, flagstone terraces, and fieldstone walls. The home has a copper roof, while sun-filled interiors and views from nearly every room connect the house with its grounds. The property is set on Turtle Back Road, near downtown New Canaan.

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*Estimate assumes a 2.5% buyer-agent commission and a 50% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24178727
Bedrooms
5
BathroomsBaths
5 full / 1 half
Square feet
5,291
Year built
1963
Acres
3.41
Property taxes
$23,070

July 2026-June 2027

What stands out

  • Japanese maples, rhododendrons, and azaleas
  • Flagstone terraces and fieldstone walls
  • Circular drive to a white Colonial
  • Specimen plantings beneath mature trees
  • Copper roof and established gardens
  • Sun-filled interiors with views from nearly every room
  • Nearly three and a half acres
Read the full listing description

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.

Schools

Elementary
West
Middle
Saxe Middle
High
New Canaan

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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248 Turtle Back Road, New Canaan, CT 06840

Price history

DateEventPrice
Originally listed$4,000,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $4,000,000 asking price × assumed 2.5% buyer-agent commission × 50% rebate = $50,000. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by Compass Connecticut, LLC · (203) 442-6626

John Dunn

SmartMLS · Listing #24178727 · Active

Listing data checked: Sep 18, 2026, 7:04 AM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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