25 Contentment Island Road, Darien, Connecticut 06820

About this home

Introducing one of Tokeneke's most iconic waterfront estates available for the first time in 40 years. A rare opportunity to rent a brand-new coastal masterpiece. "Never again" panoramic views of the Long Island Sound that will take your breath away due to the unique location of the Main House. Unparalleled serenity, beauty and access to the water, in the heart of Darien's most coveted enclave. Set on approximately 2.88 acres of exquisitely landscaped grounds with 180 feet of your own private beach! Moor your boat, enjoy the beach, kayak, take a dip in the heated waterfront pool.

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

Availability, Pets & Lease

Interior

Building & Exterior

Lot & Land

What's nearby

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable rentals

The 5 closest recent leases to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded lease 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 rentals — median $30,000/mo, ranging $17,500/mo to $45,000/mo.

Within about a mile and a half, leased in the last 2 years
• 6 Searles Road5 bd · 5 ba · 4,740 sq ft · 0.9 mi away
  $17,500/mo2025-03-17
• 7 Whaling Road5 bd · 6 ba · 6,748 sq ft · 1.0 mi away
  $30,000/mo2026-10-02
• 7 Whaling Road5 bd · 6 ba · 6,748 sq ft · 1.0 mi away
  $45,000/mo2026-05-08
• 14 Five Mile River Road6 bd · 9 ba · 6,860 sq ft · 1.2 mi away
  $35,000/mo2026-08-13
Same town, leased in the last 3 years
• 155 Pear Tree Point Road4 bd · 3 ba · 4,794 sq ft · 1.6 mi away
  $20,000/mo2025-12-01

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.

More rentals in Darien

Closest in price to this one.

• 20 Marianne Road5 bed · 8 bath · 6,521 sq ft$30,000/mo
• 61 Five Mile River Road4 bed · 3 bath · 3,207 sq ft$25,000/mo
• 9 Tory Hole Road5 bed · 4 bath · 3,553 sq ft$20,000/mo
• 16 Overbrook Lane5 bed · 5 bath · 5,166 sq ft$17,000/mo
• 31 LaForge Road4 bed · 4 bath · 2,532 sq ft$17,000/mo
• 13 Fox Hill Lane5 bed · 7 bath · 5,600 sq ft$15,000/mo

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