6 Twin Circle Drive
Westport, Connecticut 06880
- Beds
- 6
- Baths
- 5 | 2
- SqFt
- 8,717
- Acres
- 1.39
- Year Built
- 2013
- Neighborhood
- Long Lots
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
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
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
71
56 under contract
Median List Price
$4.60M
71 active listings
Median Closed Price
$2.42M
303 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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
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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 10:01 AM UTC.