171 Proprietors Crossing, New Canaan, Connecticut 06840

About this home

Updated to perfection, this classic 5-bedroom Connecticut Colonial offers over 5,500 square feet of curated living space, harmoniously positioned on a private, sought-after cul-de-sac within an enclave of 4+ acre estates. The residence unfolds with a sun-drenched brand new chef's kitchen featuring custom cabinetry, premium quartz countertops, and high-end appliances, all flowing through floor-to-ceiling glass sliders to an expansive deck and a grand family room anchored by a stately fireplace. A sophisticated main level offers a formal dining room, elegant living room, and a bespoke private office with picturesque views of the park-like grounds. Upstairs, the primary suite serves as a sanctuary with a dedicated sitting room and new spa-inspired bath, while a separate private-entry in-law suite provides a secluded fifth bedroom and sitting area for ultimate versatility. The newly finished 1,700-square-foot walk-out lower level elevates entertaining with a massive media/playroom, an additional family room, and potential for a custom wine cellar-all just minutes from the vibrant New Canaan town center, top-tier schools, and the Metro-North train.

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 $2,678,671, ranging $2,400,000 to $3,053,000.

Within a 15-minute walk, sold in the last year
• 1038 West Road4 bd · 3 ba · 4,562 sq ft · 0.2 mi away
  $2,500,000$548/sq ft2026-05-01
• 1038 West Road4 bd · 3 ba · 4,562 sq ft · 0.2 mi away
  $2,400,000$526/sq ft2025-11-19
• 1690 Oenoke Ridge6 bd · 7 ba · 5,552 sq ft · 0.2 mi away
  $3,000,000$540/sq ft2026-07-09
• 176 Logan Road5 bd · 4 ba · 4,428 sq ft · 0.5 mi away
  $2,678,671$604/sq ft2026-03-31
• 54 Saint George Lane4 bd · 5 ba · 5,244 sq ft · 0.5 mi away
  $3,053,000$582/sq ft2026-06-25

More homes in New Canaan

Closest in price to this one.

• 235 Hawks Hill Road5 bed · 6 bath · 5,458 sq ft$2,495,000
• 48 Brookwood Lane3 bed · 2 bath · 1,483 sq ft$2,495,000
• 40 Shadow Lane6 bed · 5 bath · 4,425 sq ft$2,395,000
• 559 Cheese Spring Road5 bed · 5 bath · 4,348 sq ft$2,395,000
• 599 North Wilton Road5 bed · 6 bath · 4,384 sq ft$2,395,000
• 667 Carter Street4 bed · 3 bath · 3,264 sq ft$2,595,000

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