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34 Woodside Avenue

Westport, Connecticut 06880

PENDING$2,699,000
Beds
4
Baths
4 | 1
SqFt
3,600
Acres
0.77
Year Built
1858
Matt Caiola

Matt Caiola

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2-Car Garage3 Fireplaces

About This Home

Steeped in history yet thoughtfully reimagined for modern living, this expanded and recently updated antique home offers the rare combination of timeless character, exceptional functionality, and a coveted location just an easy stroll to downtown Westport. Designed for both everyday living and easy entertaining, the home features warm gathering spaces and private retreats. A chef's kitchen with Thermador range and walk-in pantry opens to the home's inviting living and dining areas. Over $600K of recent updates including the stunning, newly-redesigned primary suite - a true sanctuary, with a new focal wall with custom cabinetry and gas fireplace, a well-equipped bath with dual sinks, tub and shower, plus a distinctive turreted sitting room, an idyllic space to relax. Multiple home office options. A new outbuilding elevates the property to an entirely new level. Designed as a private wellness retreat, this extraordinary Onsen-inspired space features hot and cold plunge pools, a sauna, shower, gas fireplace, and loft, creating a resort-quality experience. Outside, the sunny, level property features a new, walled-garden, crushed-stone patio and a 2nd patio, allowing for entertaining, gardening, and enjoying the peaceful surroundings. Room for pool! Town water/gas/sewer. Rich in character, beautifully updated, and uniquely equipped for modern wellness and work-from-home living, this exceptional residence offers a lifestyle rarely found in this historic, near-town neighborhood.

Key Facts

City/Town
Westport
Neighborhood
Old Hill
Property / Style
Single Family · Antique
Year Built
1858
Days on Market
24 days
Beds
4
Baths
4 full · 1 half
Living Area
3,600 sq ft
Lot Size
0.77 acres
Garage / Parking
2 garage
Property Taxes
$15,352 / Annually

Market Snapshot

The Westport Market

Single Family · trailing 12 months

View area

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

$2.70M

vs $4.60M median

41.3% below median

Price / Sq Ft

$750

vs $820 median

8.5% below median

Days on Market

24 days

vs 56 days median

32 days fresher 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

34 Woodside Avenue, Westport, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$15,940

per month

  • Principal & Interest$13,761
  • Property Taxes$1,279
  • Insurance$900
  • 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
Antique
Year Built
1858
New Construction
No/Resale
Living Area
3,600 sq ft
Below Grade
400 sq ft

Schools

Elementary
Kings Highway
High
Staples

Interior

Heating
Hot Air
Heat Fuel
Natural Gas
Cooling
Central Air
Fireplaces
3
Laundry
Lower Level
Appliances
Gas RangeOven/RangeRange HoodRefrigeratorSubzeroIcemakerDishwasherDisposalWasherDryerWine Chiller
Basement
FullHeatedSump PumpFully FinishedGarage AccessInterior Access
In-Law Apartment
PossibleLower Level
Interior Features
Audio SystemAuto Garage Door OpenerCentral VacuumIntercomOpen Floor PlanSecurity System
Additional Rooms
Mud RoomMusic Room

Exterior & Lot

Lot Size
0.77 acres
Zoning
AA
Garage / Parking
2 garage spacesAttached Garage
Waterfront Details
Beach Rights
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
ClapboardWood
Color
creme
Roof
Asphalt Shingle
Foundation
Block
Exterior Features
ShedPorchGuttersGarden AreaLightingStone WallUnderground Sprinkler
Lot Description
Fence - FullDry

Listing & Financials

Property Taxes
$15,352 / Annually
Days on Market
24
MLS #
24185246
MLS Status
Under Contract

Similar Properties

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

Listed By

Cyd Hamer

(917) 744-5089

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 10:55 AM UTC.