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55 Calhoun Drive

Greenwich, Connecticut 06831

ACTIVE$8,795,000
Beds
6
Baths
7 | 3
SqFt
8,273
Acres
1.42
Year Built
1929
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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5-Car Garage4 Fireplaces

About This Home

Majestic six bedroom manor, completely rebuilt with exceptional quality and craftsmanship, and sited on stunning 1.4 park-like acres in coveted Calhoun Drive Association. This distinguished residence is gracefully elevated to offer sweeping views of expansive lawns, lovely gardens and specimen trees. Impressive, sophisticated interiors throughout offer soaring ceilings, gleaming hardwood floors and sunlit living space. A grand foyer opens to a gracious floor plan of spacious rooms perfect for formal entertaining and casual living. Highlights include an airy sun room, coffered ceiling family room & breakfast room, all opening to a expansive terrace with stunning lawn and garden views. Generous space for a new custom kitchen. Luxurious primary suite features two marble Waterworks bathrooms, walk in closets and a sitting room with access to a private balcony. An additional private guest suite provides enhanced comfort for guests. A welcoming garden level offers a media room, wet bar, wine cellar, gym with full bath and playroom with access to a private outdoor covered terrace. The main residence has a three car garage. There is a charming two story carriage house with storage for two more cars. This stately home, located on a quiet cul-de-sac, is close to downtown Greenwich with fine shopping and dining and transportation to NYC.

Key Facts

City/Town
Greenwich
Neighborhood
N/A
Property / Style
Single Family · Colonial
Year Built
1929
Days on Market
67 days
Beds
6
Baths
7 full · 3 half
Living Area
8,273 sq ft
Lot Size
1.42 acres
Garage / Parking
5 garage
Property Taxes
$55,325 / Annually
HOA Fee
$1,700 / Other

Market Snapshot

The Greenwich Market

Single Family · trailing 12 months

Median Days on Market

43

42 active listings

Median $ / Sq Ft

$858

42 active listings

Sale-to-List Ratio

100.4%

176 sales

How this home compares

List Price

$8.79M

vs $3.54M median

2.5× the median

Price / Sq Ft

$1,063

vs $858 median

23.9% above median

Days on Market

67 days

vs 43 days median

24 days longer than median

Based on 42 active and 176 closed sales (trailing 12 mo) of single family in Greenwich. Source: SmartMLS · As of July 27, 2026.

Location

55 Calhoun Drive, Greenwich, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$52,527

per month

  • Principal & Interest$44,843
  • Property Taxes$4,610
  • Insurance$2,932
  • HOA$142

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
Colonial
Year Built
1929
New Construction
No/Resale
Living Area
8,273 sq ft
Below Grade
1,336 sq ft

Schools

Elementary
Glenville
High
Greenwich

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
4
Laundry
Upper Level
Appliances
None
Basement
PartialPartially FinishedPartial With Walk-Out

Exterior & Lot

Lot Size
1.42 acres
Zoning
RA-1
Garage / Parking
5 garage spacesAttached GarageDetached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Construction
WoodStucco
Roof
Slate
Foundation
Concrete
Lot Description
Level LotRolling

HOA / Association

Fee
$1,700 / Other

Listing & Financials

Property Taxes
$55,325 / Annually
Days on Market
67
MLS #
24177074
MLS Status
Active

Similar Properties

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Listed By

Barbara Wells

(203) 912-5644

Houlihan Lawrence

(203) 869-0700

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/27/2026. 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 7/27/2026 at 5:45 AM UTC.