27 White Oak Shade Lane, New Canaan, Connecticut 06840

About this home

Set on charming White Oak Shade Lane, this spacious expanded saltbox features four-bedrooms, three full baths and offers space, privacy, and a location few properties can match. Downtown New Canaan and Darien are each a short drive away, along with convenient access to the train and parkway. Inside, generous room proportions and a practical floor plan support both comfortable living and flexible entertaining. The primary bedroom serves as a private retreat with a full bath and large closet, while three additional bedrooms offer flexibility for family, guests, or a home office all supported by a generously sized hall bath. Outside, the half-acre grounds offer a large bluestone terrace in addition to ample room to cultivate a garden, enjoy a playdate, or expand the current footprint; a canvas ready for its next owner's vision. The cul-de-sac setting invites fun neighborhood events and means minimal traffic and privacy, a combination that's increasingly hard to find in such a central location.

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 $1,625,000, ranging $1,175,000 to $2,275,000.

Within a 15-minute walk, sold in the last year
• 254 White Oak Shade Road4 bd · 3 ba · 2,461 sq ft · 0.5 mi away
  $2,275,000$924/sq ft2026-06-10
• 234 Marvin Ridge Road3 bd · 2 ba · 2,175 sq ft · 0.5 mi away
  $1,490,000$685/sq ft2025-12-10
• 12 Gerdes Road4 bd · 4 ba · 2,671 sq ft · 0.5 mi away
  $1,175,000$439/sq ft2026-10-08
• 216 White Oak Shade Road4 bd · 4 ba · 2,404 sq ft · 0.6 mi away
  $1,625,000$675/sq ft2026-01-22
Within about a mile and a half, sold in the last 2 years
• 151 Butler Lane4 bd · 4 ba · 3,078 sq ft · 0.4 mi away
  $2,139,000$694/sq ft2025-04-28

More homes in New Canaan

Closest in price to this one.

• 68 Old Stamford Road5 bed · 3 bath · 2,788 sq ft$1,495,000
• 21 Hampton Lane3 bed · 3 bath · 2,432 sq ft$1,595,000
• 76 Comstock Hill Road3 bed · 3 bath · 3,688 sq ft$1,695,000
• 20 Lincoln Drive4 bed · 2 bath · 2,156 sq ft$1,249,000
• 145 Weed Street4 bed · 3 bath · 2,300 sq ft$1,150,000
• 40 Ogden Road3 bed · 1 bath · 1,450 sq ft$1,049,000

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