55 Calhoun Drive
Greenwich, Connecticut 06831
- Beds
- 6
- Baths
- 7 | 3
- SqFt
- 8,273
- Acres
- 1.42
- Year Built
- 1929
- Property Type
- Single Family

Matt Caiola
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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
Active Listings
42
24 under contract
Median List Price
$3.54M
42 active listings
Median Closed Price
$2.40M
176 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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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.