About This Home

This 5-bedroom, 8-bathroom single family at 21 Calhoun Drive in Greenwich, CT is listed for $6,150,000 ($1,001 per sqft). Built in 1923, the home offers 6,143 sqft of living space on a 1.80 acres lot.

Key Features

  • Built in 1923
  • 1.80 acre lot
  • Fireplace

Property Details

6 full, 2 half
3-car garage
1923

Amenities

FireplaceA/C
Listing Description

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.

Monthly Cost Estimate

$34,491/mo

20% down · 6.5% · 30 years

Principal$4,448
Interest$26,650
Insurance$1,794
HOA$1,600

Estimates only. Actual payments may vary.

Location

21 Calhoun Drive

Greenwich, CT 06831

Features & Amenities

Exterior Features

Patio

Property Details

Outdoor Features

Patio

Heating

Hot Water(Heating)

Cooling

Central Air

Appliances

Gas RangeWall OvenMicrowaveRefrigeratorFreezerDishwasherWine Chiller

Questions & Answers

This 5-bedroom, 8-bathroom single family at 21 Calhoun Drive is listed at $6,150,000 ($1,001/sqft). The estimated monthly payment is $34,492 based on 20% down, a 30-year loan at 6.5% interest, estimated insurance, HOA fees.

HOA fees are $1600/month.

Key features include: Built in 1923, 1.80 acre lot, Fireplace. Exterior Features: Patio.

This property is listed by Danielle Malloy and can be reached at 2039219987.

DM

Danielle Malloy

Agent at SERHANT CONNECTICUT LLC

(203) 921-9987
Agent website

Listed by SERHANT CONNECTICUT LLC · Broker phone: (646) 480-7665 · View on Broker Site · Broker website

MLS# 24205524· Source: SmartMLS, Inc.· 15 days on PropertySimple

Copyright © 2026 SmartMLS, Inc. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

21 Calhoun Drive, Greenwich, CT 06831

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