55 Calhoun Drive, Greenwich, Connecticut 06831

About this home

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors and sunlit living space. A grand foyer opens to a gracious floor plan of spacious rooms perfect for formal entertaining and casual living. Highlights include an airy sun room, coffered ceiling family room & breakfast room, all opening to a expansive terrace with stunning lawn and garden views. Generous space for a new custom kitchen. Luxurious primary suite features two marble Waterworks bathrooms, walk in closets and a sitting room with access to a private balcony. An additional private guest suite provides enhanced comfort for guests. A welcoming garden level offers a media room, wet bar, wine cellar, gym with full bath and playroom with access to a private outdoor covered terrace. The main residence has a three car garage. There is a charming two story carriage house with storage for two more cars. This stately home, located on a quiet cul-de-sac, is close to downtown Greenwich with fine shopping and dining and transportation to NYC.

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 $4,775,000, ranging $2,995,000 to $7,700,000.

Within a 15-minute walk, sold in the last year
• 20 Sherwood Farm Lane6 bd · 8 ba · 7,930 sq ft · 0.6 mi away
  $4,600,000$580/sq ft2025-12-08
• 14 Meadow Drive10 bd · 9 ba · 9,483 sq ft · 0.6 mi away
  $7,700,000$811/sq ft2025-11-28
Within about a mile and a half, sold in the last 2 years
• 17 Alden Road5 bd · 6 ba · 7,993 sq ft · 0.3 mi away
  $4,775,000$597/sq ft2024-12-20
• 36 Edgewood Drive4 bd · 5 ba · 5,812 sq ft · 0.4 mi away
  $4,925,000$847/sq ft2025-06-09
• 7 Curt Terrace5 bd · 5 ba · 7,720 sq ft · 1.3 mi away
  $2,995,000$387/sq ft2026-06-30

Recorded sales

Deed transfers on file with the Greenwich 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.

• 2003-10-24$2,757,500

More homes in Greenwich

Closest in price to this one.

• 189 Shore Road4 bed · 4 bath · 4,262 sq ft$8,750,000
• 34 Carrington Drive6 bed · 9 bath · 9,440 sq ft$8,250,000
• 203 Shore Road5 bed · 6 bath · 6,723 sq ft$9,875,000
• 24 Stillman Lane5 bed · 9 bath · 6,749 sq ft$7,599,000
• 94 Porchuck Road6 bed · 9 bath · 10,134 sq ft$7,500,000
• 96 Porchuck Road6 bed · 10 bath · 10,245 sq ft$7,500,000

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