34 Pequot Trail
Westport, Connecticut 06880
- Beds
- 5
- Baths
- 3 | 1
- SqFt
- 3,782
- Acres
- 1.13
- Year Built
- 1960
- Neighborhood
- Old Hill
- 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
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
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
70
56 under contract
Median List Price
$4.70M
70 active listings
Median Closed Price
$2.42M
303 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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.
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.