20 Gray Squirrel Drive, New Canaan, Connecticut 06840

About this home

Privately set at the end of a quiet cul-de-sac, this classic Colonial offers exceptional privacy, beautifully proportioned living spaces and a one-of-a-kind detached barn on a level 2-acre lot. The 4-bedroom home features a warm, timeless floor plan designed for both everyday living and entertaining. An open foyer leads to an inviting living room with built-in bookshelves and window seating, while the cozy den is ideal for work or study. A dedicated dining room, eat-in kitchen and sun-filled breakfast nook flow seamlessly to the patio and private backyard. The family room is filled with natural light and anchored by one of two first-floor fireplaces. Upstairs, the spacious primary suite features a large bath and oversized walk-in closet, along with three additional bedrooms and a full bath. The lower level offers flexible space and future potential. The true bonus feature is the detached barn, built in 2019 with workshop and finished living space. From an entertaining space to artist's studio, home office, gardening retreat or workshop, the possibilities are endless. Together, the cul-se-sac location, private setting, traditional layout, plus barn create something truly special.

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 $2,100,000, ranging $1,450,000 to $2,725,000.

Within a 15-minute walk, sold in the last year
• 463 White Oak Shade Road4 bd · 3 ba · 3,224 sq ft · 0.3 mi away
  $2,300,100$713/sq ft2026-09-01
• 34 Horton Lane4 bd · 4 ba · 3,512 sq ft · 0.4 mi away
  $2,725,000$775/sq ft2026-07-13
• 213 Marvin Ridge Road4 bd · 4 ba · 3,846 sq ft · 0.4 mi away
  $2,100,000$546/sq ft2025-11-14
• 224 Marvin Ridge Road3 bd · 3 ba · 3,122 sq ft · 0.5 mi away
  $1,450,000$464/sq ft2026-06-18
• 44 Putnam Road5 bd · 4 ba · 3,724 sq ft · 0.6 mi away
  $1,817,000$487/sq ft2025-12-16

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.

• 523 Brookside Road5 bed · 4 bath · 3,286 sq ft$1,995,000
• Gravel Island Road4 bed · 3 bath · 4,183 sq ft$1,999,000
• 327 Jelliff Mill Road5 bed · 5 bath · 3,383 sq ft$2,000,000
• 12 Norholt Drive4 bed · 3 bath · 2,802 sq ft$2,250,000
• 761 New Norwalk Road5 bed · 4 bath · 2,904 sq ft$1,699,000
• 178 Pocconock Trail5 bed · 4 bath · 4,543 sq ft$2,295,000

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