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5 Beds
8 Baths
6,143 sqft

$6,150,000

21 Calhoun Drive, Greenwich CT, 06831

Price per sqft$1,001.14
Built in1923
Property size6,143 sqft
Property typeResidential

Overview

Active

Listed Sep 9, 2026

Updated 23h ago

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 guest house, 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.

$40,916/mo

Est. mortgage payment based on a $6,150,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
125808

Interior Features

Bedrooms
5
Bathrooms
8
Fireplace
Yes
Cooling
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
1.8 Acres

Other Property Details

Taxes
$29,276
Tax Frequency
Annually
Garage
Yes
Pool
Yes
MLS provider logo

Listed by Danielle Malloy with Serhant Connecticut LLC
Listing Contact:  

The IDX display contains information sourced from the Greenwich Association of REALTORS® as of 10/5/2026. This data is intended solely for personal, non-commercial use and is not to be utilized for any other purposes except to identify potential properties for purchase. Although the MLS data displayed is typically considered reliable, it is not guaranteed to be accurate by the MLS. Buyers are responsible for verifying the accuracy of all information and are advised to conduct their own investigations or seek professional assistance. Other sources besides the Listing Agent may have contributed to the MLS data presented. Unless expressly specified in writing, the Broker/Agent has not confirmed any information obtained from external sources. The Broker/Agent may or may not have acted as the Listing and/or Selling Agent and cannot guarantee the accuracy of property locations displayed on any map. Any compensation offers are solely made to participants of the MLS where the listing is registered.

©2026 Greenwich Association of REALTORS® all rights reserved.

Data last updated on 10/5/2026 at 3:10 AM UTC

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