21 Calhoun Drive
Greenwich, Connecticut 06831
- Beds
- 5
- Baths
- 6 | 2
- SqFt
- 6,143
- Acres
- 1.80
- Year Built
- 1923
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
A rare opportunity in one of Greenwich's most coveted in-town settings. 21 Calhoun Drive combines the presence and character of a classic Greenwich estate with exceptional privacy, generous scale and close proximity to everything that makes Greenwich living so desirable. Set amid mature landscaping on an oversized approximately 1.8-acre property in a one-acre zone, the estate offers nearly twice the typical lot size and exceptional flexibility for the future. Gracious entertaining rooms, comfortable everyday living spaces and architectural details give the residence a depth and personality rarely found in newer construction, while the established grounds provide both privacy and room to further enhance the property. What truly distinguishes 21 Calhoun is the opportunity it presents. Offered with a building permit and engineering for a guest house, the property provides the flexibility to enjoy the existing residence, thoughtfully expand over time, or create a substantial multi-generational Greenwich compound. The oversized acreage also creates compelling possibilities for additional outdoor amenities, including potential sports or recreation areas, subject to applicable requirements and approvals. With its established residence, unusually generous acreage, valuable planning already in place and significant future potential, 21 Calhoun represents a compelling opportunity to acquire a substantial Greenwich estate at a value increasingly difficult to replicate.
Key Facts
- City/Town
- Greenwich
- Neighborhood
- N/A
- Property / Style
- Single Family · Tudor
- Year Built
- 1923
- Days on Market
- 0 days
- Beds
- 5
- Baths
- 6 full · 2 half
- Living Area
- 6,143 sq ft
- Lot Size
- 1.80 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $37,450 / Annually
- HOA Fee
- $1,600 / Annually
Market Snapshot
The Greenwich Market
Single Family · trailing 12 months
Active Listings
41
16 under contract
Median List Price
$3.30M
41 active listings
Median Closed Price
$2.33M
166 sales
Median Days on Market
46
41 active listings
Median $ / Sq Ft
$859
41 active listings
Sale-to-List Ratio
101.2%
166 sales
How this home compares
List Price
$6.15M
vs $3.30M median
86.4% above median
Price / Sq Ft
$1,001
vs $859 median
16.5% above median
Days on Market
0 days
vs 46 days median
46 days fresher than median
Based on 41 active and 166 closed sales (trailing 12 mo) of single family in Greenwich. Source: SmartMLS · As of September 9, 2026.
Location
21 Calhoun Drive, Greenwich, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 3, 2026per month
- Principal & Interest$31,780
- Property Taxes$3,121
- Insurance$2,050
- HOA$133
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Greenwich
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Tudor
- Year Built
- 1923
- New Construction
- No/Resale
- Living Area
- 6,143 sq ft
Schools
- Elementary
- Glenville
- High
- Greenwich
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Central Air
- Fireplaces
- 6
- Laundry
- Lower LevelMain Level
- Appliances
- Gas RangeWall OvenMicrowaveRefrigeratorFreezerDishwasherWine Chiller
- Basement
- Full
Exterior & Lot
- Lot Size
- 1.80 acres
- Zoning
- RA-1
- Garage / Parking
- 3 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Septic
- Pool
- Indoor Pool
- Construction
- BrickStucco
- Roof
- ShingleSlate
- Foundation
- Stone
- Exterior Features
- Patio
- Lot Description
- Level Lot
HOA / Association
- Fee
- $1,600 / Annually
Listing & Financials
- Property Taxes
- $37,450 / Annually
- Days on Market
- 0
- MLS #
- 24205524
- MLS Status
- Active
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/9/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/9/2026 at 5:15 AM UTC.