5 Cross Road, Darien, Connecticut 06820

About this home

Set within Darien's coveted private Tokeneke Association, 5 Cross Road is a quintessential stone Colonial gracefully positioned on a private .70 acre property. Timeless architectural character, exceptional privacy, and inviting living spaces define this distinctive residence in one of the town's most sought-after coastal neighborhoods.The thoughtfully updated kitchen serves as the heart of the home, while an extraordinary family room with soaring ceilings and abundant natural light offers a dramatic yet welcoming setting for everyday living and entertaining. A desirable first-floor primary suite provides comfort and convenience, creating an ideal layout for modern living. Classic details and generous rooms throughout complement the home's enduring stone facade and beautifully secluded grounds. Enjoy the rare combination of a tranquil residential setting, private association lifestyle, and convenient access to Darien's village, schools, train, beaches, and waterfront. A special Tokeneke offering where classic New England charm meets effortless, refined living.

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

HOA & Fees

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 $4,325,000, ranging $3,205,000 to $5,500,000.

Within a 15-minute walk, sold in the last year
• 6 Searles Road5 bd · 5 ba · 4,740 sq ft · 0.3 mi away
  $4,600,000$970/sq ft2026-09-23
• 90 Five Mile River Road5 bd · 5 ba · 5,060 sq ft · 0.4 mi away
  $4,250,000$839/sq ft2026-05-08
• 18 Winding Lane4 bd · 4 ba · 3,972 sq ft · 0.5 mi away
  $3,205,000$806/sq ft2026-03-27
Within about a mile and a half, sold in the last 2 years
• 3 Edgehill Drive5 bd · 5 ba · 3,919 sq ft · 0.1 mi away
  $4,325,000$1,103/sq ft2025-07-16
• 13 Edgehill Drive5 bd · 5 ba · 3,240 sq ft · 0.2 mi away
  $5,500,000$1,697/sq ft2026-08-27

Public record

From the Darien 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.

Recorded sales

Deed transfers on file with the Darien 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.

• 2016-10-17$2,689,000Single Family

More homes in Darien

Closest in price to this one.

• 15 Wildcat Road4 bed · 4 bath · 6,021 sq ft$3,850,000
• 700 Hollow Tree Ridge Road5 bed · 6 bath · 5,500 sq ft$3,699,500
• 222 Brookside Road5 bed · 6 bath · 10,000 sq ft$3,900,000
• 20 Lighthouse Way4 bed · 4 bath · 4,093 sq ft$3,925,000
• 18 Bates Farm Lane5 bed · 5 bath · 4,423 sq ft$3,600,000
• 31 Hancock Lane3 bed · 5 bath · 4,733 sq ft$3,595,000

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