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$2,699,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 4 Full Baths
  • 1 Partial Bath
  • 3,600 Sq. Ft.
  • 2 Car Garage
  • Updated 1 day ago

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Open House: 1:00 PM - 3:00 PM

Sunday 7/5 1:00 PM - 3:00 PM

34 Woodside Avenue,Westport, CT 06880

34 Woodside AvenueWestportCT06880

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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.

Full Property Details for 34 Woodside Ave

General

  • Price: $2,699,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24185246
  • Updated: 7/3/2026
  • Added to Site: 2 day(s) ago

Interior

  • Number of Rooms: 10
  • Rooms/Areas: Mud Room, Music Room
  • Interior Features: Audio System, Auto Garage Door Opener, Central Vacuum, Intercom, Open Floor Plan, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Gas Range, Oven/Range, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Disposal, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 5
  • Full Bathrooms: 4
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Remodeled, Cathedral Ceiling, Built-Ins, Gas Log Fire, Upper
  • Bedroom 1: Bedroom - Full Bath, Hardwood Floor, Main
  • Bedroom 2: Bedroom - Built-Ins, Wall/Wall Carpet, Upper
  • Bedroom 3: Bedroom - Built-Ins, Wall/Wall Carpet, Upper

Other Rooms

  • Living Room: Living Room - Ceiling Fan, Combination Liv/Din Rm, Fireplace, Wide Board Floor, Main
  • Kitchen: Kitchen - Granite Counters, Pantry, Tile Floor, Main
  • Dining Room: Dining Room - Combination Liv/Din Rm, Wide Board Floor, Main
  • Office: Office - Engineered Wood Floor, Gas Log Fireplace, Lower
  • Library: Library - Skylight, Vaulted Ceiling, Hardwood Floor, Lower
  • Game room: Yes
  • Game Room: Rec/Play Room - Book Shelves, Full Bath, Lower
  • Rec Room: Book Shelves, Full Bath, Lower
  • Laundry: Lower Level

Exterior

  • Exterior Features: Shed, Porch, Gutters, Garden Area, Lighting, Stone Wall, Underground Sprinkler
  • Color: creme

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Old Hill
  • Driving Directions: Kings Highway to Woodside Avenue

School Information

  • Elementary School: Kings Highway
  • Middle School: Coleytown
  • High School: Staples

Community

  • Community Name: Old Hill

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Natural Gas
  • Heating Fuel: Natural Gas
  • Water Heater: 50 Gallon Tank

Utilities

  • Sewer: Public Sewer Connected
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Antique
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard, Wood
  • Basement Desc.: Full, Heated, Sump Pump, Fully Finished, Garage Access, Interior Access
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,600
  • Above Ground: 3,200 Sq. Ft.
  • Below Ground: 400 Sq. Ft.
  • Year Built: 1858

Lot Features

  • Lot Size (Acres): 0.77
  • Zoning: AA
  • Lot Description: Fence - Full, Dry

Water Features

  • Water Front Desc.: Beach Rights

Green Features

  • Energy Features: Thermopane Windows

Financial Considerations

  • Assessment Amount: $813,800
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: See inclusions/exclusions document.
  • Property ID: 413050

Listed by William Pitt Sotheby's Int'l, Cyd Hamer

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Listing agent

— 34 Woodside Ave —

  • Cyd Hamer

    William Pitt Sotheby's Int'l

Agent Contact: (917) 744-5089 Office Contact: (203) 227-1246

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 34 Woodside Ave

School District:Westport School District
NameGradesDistance
King's Highway Elementary School
125 Post Road West, Westport, CT 06880
K-50.5 mi
Coleytown Middle School
255 North Avenue, Westport, CT 06880
6-82.8 mi
Staples High School
70 North Avenue, Westport, CT 06880
9-122.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 34 Woodside Ave Get Price Alerts and Save Property

Date
Details
Price
Change
Source
7/02/2026
Listed
$2,699,000
36.66%
MLS
6/22/2022
Sold
$1,975,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 34 Woodside Ave

Year
Property Taxes
Change
Tax Assessment
Change
2025
$15,348
5%
$813,800
3%
2023
$14,641
1%
$786,300
—
2023
$14,429
13%
$786,300
12%
2022
$12,727
—
$704,300
—
2021
$12,727
—
$704,300
-7%
2020
$12,691
-1%
$759,500
—
2019
$12,805
—
$759,500
—
2018
$12,805
—
$759,500
—
2017
$12,805
—
$759,500
—
2016
$12,805
-2%
$759,500
5%
2015
$13,092
1%
$723,700
—
2014
$12,983
-1%
$723,700
—
2011
$13,077
—
$723,700
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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NMLS#: 1598647

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Listed by William Pitt Sotheby's Int'l, Cyd Hamer

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34 Woodside Avenue, Westport, CT 06880 (MLS# 24185246) is a Single Family property with 4 bedrooms, 4 full bathrooms and 1 partial bathroom. 34 Woodside Avenue is currently listed for $2,699,000 and was received on July 02, 2026. Want to learn more about 34 Woodside Avenue? Do you have questions about finding other Single Family real estate for sale in Westport? You can browse all Westport real estate or contact a Coldwell Banker agent to request more information.

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