23 Punch Bowl Drive
Westport, Connecticut 06880
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,017
- Acres
- 1.25
- Year Built
- 1958
- Neighborhood
- Coleytown
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Tucked away on 1.25 serene acres in Westport's sought-after Coleytown neighborhood, this timeless 5-bedroom Georgian Colonial seamlessly blends grand architectural elegance with comfortable everyday living. Welcomed by an inviting, large front porch this impressive home offers exceptional space both inside and out. Inside, the grand main level flows effortlessly between a large formal living room, a gracious formal dining room, and a designated home office. At the heart of the home, a spacious, sunny kitchen connects directly to a casual den/TV room, while double doors lead from both the kitchen and dining room onto a lovely patio ideal for outdoor dining and entertaining. One of the home's most show-stopping features is the massive bonus room,expertly crafted from real barn wood and complete with exposed timber beams, wide plank wood floors, and a dedicated fireplace, perfect for cozy evenings or hosting large gatherings. Throughout the main house, you will find a total of 3 fireplaces creating a warm, inviting atmosphere. Upstairs, the expansive primary suite serves as a peaceful retreat featuring a massive walk-in closet and a remarkably large primary bathroom. A second spacious bedroom functions as its own suite, featuring a private bathroom and an exclusive balcony overlooking the grounds. The resort-style backyard oasis centers around an inground pool and a fun, fully equipped pool house featuring a private bathroom and its own fireplace for chilly evening gathering.
Key Facts
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
62
39 under contract
Median List Price
$5.17M
62 active listings
Median Closed Price
$2.42M
304 sales
Median Days on Market
38
62 active listings
Median $ / Sq Ft
$835
62 active listings
Sale-to-List Ratio
100.0%
304 sales
How this home compares
List Price
$2.50M
vs $5.17M median
51.7% below median
Price / Sq Ft
$622
vs $835 median
25.5% below median
Days on Market
0 days
vs 38 days median
38 days fresher than median
Based on 62 active and 304 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of October 7, 2026.
Location
23 Punch Bowl Drive, Westport, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 1, 2026per month
- Principal & Interest$13,684
- Property Taxes$1,808
- Insurance$833
- 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
- Georgian Colonial
- Year Built
- 1958
- New Construction
- No/Resale
- Living Area
- 4,017 sq ft
Schools
- Elementary
- Coleytown
- High
- Staples
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Attic FanCeiling FansCentral AirZoned
- Fireplaces
- 4
- Laundry
- Upper Level
- Appliances
- Gas CooktopOven/RangeRefrigeratorDishwasher
- Basement
- FullUnfinishedStorageGarage Access
- Interior Features
- Auto Garage Door Opener
Exterior & Lot
- Lot Size
- 1.25 acres
- Zoning
- AA
- Garage / Parking
- 4 garage spacesAttached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Public Water Connected
- Sewer
- Septic
- Pool
- Pool HouseIn Ground Pool
- Construction
- BrickWood
- Color
- Brick, White
- Roof
- Shingle
- Foundation
- BlockConcrete
- Exterior Features
- PorchCabanaGarden AreaLightingFrench DoorsPatio
- Lot Description
- Fence - PartialTreedLevel LotSloping Lot
Listing & Financials
- Property Taxes
- $21,692 / Annually
- Days on Market
- 0
- MLS #
- 24212307
- 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 10/7/2026. 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 10/7/2026 at 12:01 AM UTC.