For Sale
Single family home for sale at 21 Calhoun Dr, Greenwich, CT 06831 | MLS# 24205524 | Listing updated on 2026-10-25
Photo 1 of Single family home for sale at 21 Calhoun Dr, Greenwich, CT 06831 | MLS# 24205524 | Listing updated on 2026-10-25
Photo 2 of Single family home for sale at 21 Calhoun Dr, Greenwich, CT 06831 | MLS# 24205524 | Listing updated on 2026-10-25
Photo 3 of Single family home for sale at 21 Calhoun Dr, Greenwich, CT 06831 | MLS# 24205524 | Listing updated on 2026-10-25
Photo 4 of Single family home for sale at 21 Calhoun Dr, Greenwich, CT 06831 | MLS# 24205524 | Listing updated on 2026-10-25
16+
Beds Icon

Street View

$6,150,000

Monthly Est:$30,611

  • Beds Icon5 Beds
  • Beds Icon
    8 Baths
  • Beds Icon6,143sqft

21 Calhoun Dr, Greenwich, CT 06831

$30,611/moEst:

Get Pre-Approved

  • Single Family Residence

  • Built in 1923

  • $133.33/mo HOA

  • 1.8 acres lot

  • $1,001/sq.ft

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.

  • Houzeo last checked: 37 minutes ago
  • Listing updated: October 25, 2026 at 9:40 pm
  • Listing Provided by: Danielle Malloy | Serhant Connecticut, LLC
  • Source: SMART MLS-CT | MLS#: 24205524 SMART MLS-CT

Property Details

  • Status

    Active

  • Type

    Single Family Residence

  • No. of Stories

    -

  • County

    Fairfield County

  • City

    Greenwich

  • Neighborhood

    --

  • Year Built

    1923

  • HOA Fees

    $133.33/mo

  • Finished Area

    6,143 sqft

  • Lot Size

    1.8 acres lot

  • Basement Area

    - sqft

  • MLS Name

    SMART MLS

  • MLS Number

    24205524

  • MLS Status

    Active

  • Days on Market

    52

Continue Your Journey in App

Find your dream home, receive real-time updates, and many more!

Location

HOA Management

1

HOA Fees

$1,600/ Annually

Amenities

Amenities and services may be covered by one or multiple associations and service providers.

Snow Removal Snow Removal

Road Maintenance Road Maintenance

Disclaimer: Amenities are based on third-party information and may vary; buyers must independently verify all amenities, as information is deemed reliable but not guaranteed.

Facts & Features

Rooms

  • Bedrooms & bathrooms

    Bedrooms: 5

    Bathrooms: 8

Interior

  • Heating

    Natural Gas, Hot Water

  • Sewer

    Septic

  • Appliances

    Gas Range, Wall Oven, Microwave, Refrigerator, Freezer, Dishwasher, Wine Chiller

  • Exterior Features

    Patio

  • Cooling

    Central Air

Construction

  • Year Built

    Year Built: 1923

  • Home type

    Single Family Residence

  • Architectural Style

    Tudor

  • Foundation Details

    Stone

  • Roof

    Shingle, Slate

Utilities & Energy

  • Water Source

    Public Water Connected

  • Parking Features

    Attached Garage

  • Pool Features

    Indoor Pool

  • Basement

    Full

  • Laundry Features

    Lower Level, Main Level

Other Features

  • Lot Features

    Level Lot

  • Subdivision Name

    N/a

Price History

DateEventPrice

09/09/2026

Source: mls_logoSMART MLS-CT #24205524

Listed for Sale

$6,150,000 +22263.64%

$1,001/sqft

07/31/2020

Source: #170318192

Sold

$27,500

$4/sqft

Nearby Homes

Based on information provided to and compiled by the SMART MLS, Inc. through Oct 31, 2026, 04:45AM. IDX information is provided exclusively for consumers’ personal, non-commercial use. It may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. The data is deemed reliable but is not guaranteed accurate by the MLS. ©2026 SMART MLS, Inc. All Rights Reserved.

Advertising Broker: Derek Greene | The Greene Realty Group

Skip to Main Content