21 Calhoun Drive, Greenwich, Connecticut 06831

About this home

A rare opportunity in one of Greenwich's most coveted in-town settings, 21 Calhoun Drive combines the timeless presence and character of a classic Greenwich estate with exceptional privacy, generous scale and remarkable potential. Set amid mature landscaping on approximately 1.8 acres in a one-acre zone, the property offers nearly twice the typical lot size while remaining just moments from the heart of Greenwich. Inside, gracious entertaining rooms, comfortable everyday living spaces and distinctive architectural details create a home with warmth, character and a sense of permanence rarely replicated today. A newly renovated kitchen brings a fresh, modern sensibility to the residence and serves as a beautiful centerpiece for daily living and entertaining. A private wellness retreat, complete with an indoor pool and dedicated fitness space, brings resort-style amenities into the comfort and privacy of home. Beyond the main residence, the expansive grounds offer an exceptional opportunity to further enhance the estate. Fully permitted plans provide the option to add a Cottage, along with the potential for a pickleball or tennis court an increasingly rare offering this close to town. With its substantial acreage, established landscaping, private wellness amenities and extraordinary flexibility for the future, this is a unique opportunity to enjoy a private estate setting without sacrificing the convenience of in-town Greenwich 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 $4,600,000, ranging $1,980,000 to $4,925,000.

Within a 15-minute walk, sold in the last year
• 34 Edgewood Drive4 bd · 6 ba · 5,244 sq ft · 0.4 mi away
  $4,600,000$877/sq ft2025-12-05
Within about a mile and a half, sold in the last 2 years
• 48 Glenville Road5 bd · 4 ba · 5,627 sq ft · 0.2 mi away
  $2,800,000$497/sq ft2024-10-17
• 36 Edgewood Drive4 bd · 5 ba · 5,812 sq ft · 0.4 mi away
  $4,925,000$847/sq ft2025-06-09
• 20 Sherwood Farm Lane6 bd · 8 ba · 7,930 sq ft · 0.5 mi away
  $4,600,000$580/sq ft2025-12-08
• 35 & 37 Rockview Drive7 bd · 5 ba · 4,944 sq ft · 0.7 mi away
  $1,980,000$400/sq ft2024-11-22

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.

• 2019-03-19$3,100,000Single Family

More homes in Greenwich

Closest in price to this one.

• 991 Lake Avenue5 bed · 7 bath · 9,493 sq ft$6,750,000
• 23 Wyckham Hill Lane6 bed · 8 bath · 8,335 sq ft$6,995,000
• 31 Meadow Wood Drive3 bed · 4 bath · 2,425 sq ft$6,995,000
• 38 Partridge Hollow Road5 bed · 8 bath · 10,981 sq ft$6,995,000
• 16 Annjim Drive5 bed · 6 bath · 6,997 sq ft$5,250,000
• 64 Hillside Road5 bed · 8 bath · 6,975 sq ft$7,495,000

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