Skip to main content

23 Punch Bowl Drive

Westport, Connecticut 06880

ACTIVE - NEW$2,500,000
Beds
5
Baths
4 | 1
SqFt
4,017
Acres
1.25
Year Built
1958
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

Call Matt
Pool4-Car Garage4 Fireplaces

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

City/Town
Westport
Neighborhood
Coleytown
Property / Style
Single Family · Georgian Colonial
Year Built
1958
Days on Market
0 days
Beds
5
Baths
4 full · 1 half
Living Area
4,017 sq ft
Lot Size
1.25 acres
Garage / Parking
4 garage
Property Taxes
$21,692 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$16,325

per 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

City/Town
Westport
Neighborhood
Coleytown
County
Fairfield

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

Similar Properties

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

Listed By

Sandy Petrino

(203) 520-1541

William Pitt Sotheby's Int'l

(203) 227-1246

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.