119 Proprietors Crossing, New Canaan, Connecticut 06840

About this home

119 Proprietors Crossing is an entertainer's dream, featuring stunning architecture by James E. Gearity. Nestled on four private acres, this six-bedroom estate blends timeless elegance with modern luxury. A private drive leads to an elegant fountain, setting an unforgettable tone. Inside, a soaring foyer showcases a dramatic Baccarat chandelier and seven fireplaces, enhancing the warm atmosphere. Spacious entertaining areas flow seamlessly to a tranquil terrace. The heart of the home includes a chef's kitchen that opens to a Great Room with a remarkable 35.5 foot vaulted ceiling, centered around a large quartz island with integrated audio. A formal dining room beneath another Baccarat chandelier sets the stage for memorable gatherings. The West wing hosts the primary suite, featuring a cozy retreat and a study with a hidden staircase leading to a gym and an 800-square-foot dressing room. An adjacent Junior Primary Suite has its own entrance and living area. Upstairs, four additional bedrooms include two ensuite and two with a jack-and-jill bath. The finished lower level boasts a media room, fitness center, and wine cellar. Outdoors, curated grounds offer a dining pavilion, outdoor kitchen, and a newly constructed pool and spa, with space for a tennis/pickle-ball court. Engineered for efficiency, the estate features commercial-grade systems, radiant heat, and a rare Welsh slate roof. A four-car garage and an elevator service complete this exceptional offering.

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

Schools

Taxes

Interior

Building & Exterior

Lot & Land

Energy

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 $5,250,000, ranging $3,200,000 to $8,000,000.

Within a 15-minute walk, sold in the last year
• 26 Pequot Lane6 bd · 8 ba · 12,385 sq ft · 0.2 mi away
  $5,250,000$423/sq ft2026-04-06
Within about a mile and a half, sold in the last 2 years
• 928 West Road7 bd · 9 ba · 11,494 sq ft · 0.4 mi away
  $8,000,000$696/sq ft2026-04-17
• 42 Alan Lane6 bd · 9 ba · 13,007 sq ft · 0.5 mi away
  $7,495,000$576/sq ft2024-12-03
• 1421 Oenoke Ridge6 bd · 11 ba · 10,940 sq ft · 0.9 mi away
  $3,200,000$292/sq ft2025-02-05
• 1247 Oenoke Ridge5 bd · 9 ba · 13,457 sq ft · 1.0 mi away
  $4,250,000$315/sq ft2025-12-19

Recorded sales

Deed transfers on file with the New Canaan land records, newest first. These are recordings rather than MLS sales, so they include transfers that were never listed. Nominal and $0 transfers (estate, trust and family conveyances) are excluded.

• 2020-01-24$3,995,000Single Family
• 2010-10-06$3,600,000Single Family

More homes in New Canaan

Closest in price to this one.

• 46 Norholt Drive6 bed · 10 bath · 9,429 sq ft$7,499,000
• 48 Driftway Lane5 bed · 7 bath · 10,655 sq ft$6,999,000
• 62 Summersweet Lane6 bed · 9 bath · 16,126 sq ft$6,595,000
• 190 Brookwood Lane6 bed · 8 bath · 10,495 sq ft$8,250,000
• 259 & 253 Frogtown Road7 bed · 10 bath · 13,026 sq ft$8,747,000
• 67 Carter Street5 bed · 8 bath · 9,300 sq ft$5,500,000

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