248 Turtle Back Road, New Canaan, Connecticut 06840

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.

Flood risk: check the FEMA flood map for this address.

Schools

Taxes

Interior

Building & Exterior

Lot & Land

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

What's nearby

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $3,053,000, ranging $2,678,671 to $4,700,000.

Within a 15-minute walk, sold in the last year
• 108 Logan Road6 bd · 8 ba · 6,069 sq ft · 0.5 mi away
  $3,325,000$547/sq ft2026-08-26
• 54 Saint George Lane4 bd · 5 ba · 5,244 sq ft · 0.5 mi away
  $3,053,000$582/sq ft2026-06-25
• 1191 Oenoke Ridge5 bd · 6 ba · 6,557 sq ft · 0.6 mi away
  $4,700,000$716/sq ft2026-08-04
• 176 Logan Road5 bd · 4 ba · 4,428 sq ft · 0.7 mi away
  $2,678,671$604/sq ft2026-03-31
Within about a mile and a half, sold in the last 2 years
• 253 Turtle Back Road4 bd · 5 ba · 5,754 sq ft · 0.1 mi away
  $2,800,000$486/sq ft2024-11-21

Public record

From the New Canaan assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

More homes in New Canaan

Closest in price to this one.

• 565 Oenoke Ridge4 bed · 5 bath · 4,927 sq ft$4,000,000
• 25 Hillcrest Road6 bed · 7 bath · 7,900 sq ft$3,995,000
• 38 Gerrish Lane5 bed · 6 bath · 5,374 sq ft$3,895,000
• 760 Valley Road6 bed · 8 bath · 7,450 sq ft$4,200,000
• 51 Briscoe Road5 bed · 7 bath · 8,243 sq ft$4,250,000
• 16 Orchard Lane5 bed · 6 bath · 5,903 sq ft$4,395,000

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