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6 Twin Circle Drive

Westport, Connecticut 06880

PENDING$5,000,000
Beds
6
Baths
5 | 2
SqFt
8,717
Acres
1.39
Year Built
2013
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

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Tennis CourtPool3-Car Garage3 Fireplaces

About This Home

Nestled on a quiet cul-de-sac in one of Westport's most convenient locations, 6 Twin Circle Drive offers luxury living with exceptional indoor and outdoor spaces. Just moments to Bedford Middle School, Staples High School, downtown Westport, trains, shopping, restaurants, Longshore, and Compo Beach, this property combines privacy, recreation, and convenience. The resort-style backyard features a pool with spa, expansive lounging areas, full outdoor kitchen, and a rare post-tension concrete tennis court - the premier surface used at elite clubs and college facilities. A truly extraordinary amenity rarely found in residential homes. The home offers an open floor plan filled with natural light and thoughtfully designed spaces. The gourmet chef's kitchen features high-end appliances, abundant workspace, and two dishwashers. Main-level highlights include elegant entertaining spaces, a private meditation room, and seamless indoor-outdoor flow. The primary suite is a retreat with a spa-inspired bath, steam shower, and dressing room with abundant closets. Upstairs, an incredible playroom with six built-in beds creates the perfect sleepover space or playroom. The walk-out lower level offers versatility with a media room, gym, office, and guest suite ideal for extended family, au pair, or guests. Rarely does a Westport luxury home offer resort-style amenities, premier tennis facilities, flexible living space, and walk-to-school convenience in such a private setting.

Key Facts

City/Town
Westport
Neighborhood
Long Lots
Property / Style
Single Family · Colonial
Year Built
2013
Days on Market
77 days
Beds
6
Baths
5 full · 2 half
Living Area
8,717 sq ft
Lot Size
1.39 acres
Garage / Parking
3 garage
Property Taxes
$35,764 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

56

71 active listings

Median $ / Sq Ft

$820

71 active listings

Sale-to-List Ratio

100.0%

303 sales

How this home compares

List Price

$5.00M

vs $4.60M median

8.7% above median

Price / Sq Ft

$574

vs $820 median

30.0% below median

Days on Market

77 days

vs 56 days median

21 days longer than median

Based on 71 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.

Location

6 Twin Circle Drive, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$30,141

per month

  • Principal & Interest$25,494
  • Property Taxes$2,980
  • Insurance$1,667
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Westport
Neighborhood
Long Lots
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial
Year Built
2013
New Construction
No/Resale
Living Area
8,717 sq ft
Below Grade
1,940 sq ft

Schools

Elementary
Long Lots
High
Staples

Interior

Heating
Zoned
Cooling
Attic FanCentral AirZoned
Fireplaces
3
Laundry
Upper Level
Laundry Location
2nd Floor
Appliances
Cook TopOven/RangeCounter GrillWall OvenMicrowaveRefrigeratorFreezerIcemakerDishwasherWasherDryer
Basement
FullHeatedFully FinishedCooledInterior AccessWalk-outLiveable Space
Interior Features
Audio SystemCentral VacuumSecurity System
Additional Rooms
Exercise RoomFoyerLaundry RoomMud RoomStaff QuartersWorkshop

Exterior & Lot

Lot Size
1.39 acres
Zoning
AA
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Pool
In Ground Pool
Construction
ShakeCedar
Color
Light Gray
Roof
Wood Shingle
Foundation
Concrete
Exterior Features
GuttersLightingFrench DoorsPatioGrillTennis CourtPorchDeckUnderground Sprinkler
Lot Description
Fence - WoodFence - PrivacyFence - FullLevel LotOn Cul-De-Sac

Listing & Financials

Property Taxes
$35,764 / Annually
Days on Market
77
MLS #
24168601
MLS Status
Under Contract - Continue to Show

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Judy Michaelis

(203) 247-5000

Coldwell Banker Realty

(203) 227-8424

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 10:01 AM UTC.