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34 Pequot Trail

Westport, Connecticut 06880

PENDING$2,100,000
Beds
5
Baths
3 | 1
SqFt
3,782
Acres
1.13
Year Built
1960
Matt Caiola

Matt Caiola

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2-Car Garage2 Fireplaces

About This Home

Discover this serene setting in a sought after Old Hill neighborhood. Two thoughtful and beautifully executed additions have made this sprawling 12 room home flow with the versatility to fit today's varied lifestyles. Comfortable open living spaces have been designed with the flexibility to offer multi-generational spaces, a home office or simply to allow for room to grow in the way that pleases you best. The welcoming living room with its broad bay window and formal fireplace provides ample room for your guests and the Baby Grand piano! The custom country kitchen is both practical and beautiful with wide plank wood floors, cherry and glass cabinetry, granite counters and a walk-in pantry. The adjoining family room with it's cathedral ceiling is filled with natural light and includes a fireplace, wet bar and French doors that open to a wraparound deck. The most recent addition is an impressive library with long, tall windows set amid tailored built-ins. An additional exterior entry makes it ideal for home office use while the adjacent full bathroom and closet offers the possibility of a first floor bedroom suite. The informal rear foyer includes access to a laundry area, powder room and extra closets. Just beyond is a 2nd private office or den. Upstairs you'll discover the primary suite with full bathroom and walk-in closet, as well as 4 very spacious additional bedrooms. Unseen value found in the new roof, updated mechanicals and whole house generator!

Key Facts

City/Town
Westport
Neighborhood
Old Hill
Property / Style
Single Family · Colonial,Split Level
Year Built
1960
Days on Market
58 days
Beds
5
Baths
3 full · 1 half
Living Area
3,782 sq ft
Lot Size
1.13 acres
Garage / Parking
2 garage · 4 total
Property Taxes
$14,718 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

Median Days on Market

60

70 active listings

Median $ / Sq Ft

$821

70 active listings

Sale-to-List Ratio

100.0%

303 sales

How this home compares

List Price

$2.10M

vs $4.70M median

55.3% below median

Price / Sq Ft

$555

vs $821 median

32.4% below median

Days on Market

58 days

vs 60 days median

In line with median

Based on 70 active and 303 closed sales (trailing 12 mo) of single family in Westport. Source: SmartMLS · As of July 27, 2026.

Location

34 Pequot Trail, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$12,634

per month

  • Principal & Interest$10,707
  • Property Taxes$1,227
  • Insurance$700
  • HOA$0

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

Location

City/Town
Westport
Neighborhood
Old Hill
County
Fairfield

Residence

Property Type
Single Family
Style
Colonial,Split Level
Year Built
1960
New Construction
No/Resale
Living Area
3,782 sq ft

Schools

Elementary
Kings Highway
High
Staples

Interior

Heating
Hot Water
Heat Fuel
Oil
Cooling
Central Air
Fireplaces
2
Laundry
Main Level
Appliances
Cook TopWall OvenMicrowaveRefrigeratorDishwasherInstant Hot Water TapWasherDryer
Basement
Crawl SpacePartialUnfinishedStorageInterior AccessConcrete Floor
Interior Features
Auto Garage Door OpenerCable - Pre-wiredOpen Floor Plan
Additional Rooms
FoyerMud Room
Accessibility
Bath Grab Bars,Multiple Entries/Exits

Exterior & Lot

Lot Size
1.13 acres
Zoning
AA
Garage / Parking
2 garage spaces4 total parking spacesAttached GaragePavedOff Street ParkingDrivewayPrivatePavedAsphalt
Waterfront Details
Beach RightsWater Community
Water Source
Public Water Connected
Sewer
Public Sewer In StreetSeptic
Flood Zone
No
Construction
ShingleBrick
Color
White
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedPorchDeckGuttersLightingStone WallFrench Doors
Lot Description
Lightly WoodedLevel LotProfessionally LandscapedRolling

Listing & Financials

Property Taxes
$14,718 / Annually
Days on Market
58
MLS #
24178738
MLS Status
Under Contract

Similar Properties

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

Listed By

Lynn Fraund

(203) 434-8585

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 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 1:10 PM UTC.