34 Woodside Avenue
Westport, Connecticut 06880
- Beds
- 4
- Baths
- 4 | 1
- SqFt
- 3,600
- Acres
- 0.77
- Year Built
- 1858
- 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
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
Market Snapshot
The Westport Market
Single Family · trailing 12 months
Active Listings
71
56 under contract
Median List Price
$4.60M
71 active listings
Median Closed Price
$2.42M
303 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per 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
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
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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 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.