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21 Calhoun Drive

Greenwich, Connecticut 06831

ACTIVE - NEW$6,150,000
Beds
5
Baths
6 | 2
SqFt
6,143
Acres
1.80
Year Built
1923
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$37,084

per 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

Similar Properties

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Listed By

Danielle Malloy

(203) 921-9987

Serhant Connecticut, LLC

(203) 489-7800

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.