About 34 Woodside Avenue
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.
Features of 34 Woodside Avenue
| MLS® # | 24185246 |
|---|---|
| Price | $2,699,000 |
| Bedrooms | 4 |
| Bathrooms | 5.00 |
| Full Baths | 4 |
| Half Baths | 1 |
| Square Footage | 3,600 |
| Acres | 0.77 |
| Type | Single Family For Sale |
| Style | Antique |
| Status | Active |
Community Information
| Address | 34 Woodside Avenue |
|---|---|
| Area | Old Hill |
| City | Westport |
| County | Fairfield |
| State | Connecticut |
| Zip Code | 06880 |
Amenities
| Features | Thermopane Windows |
|---|---|
| Parking | Attached Garage |
| # of Garages | 2 |
| Is Waterfront | No |
| Waterfront | Beach Rights |
| Has Pool | No |
Interior
| Interior Features | Audio System, Auto Garage Door Opener, Central Vacuum, Intercom, Open Floor Plan, Security System |
|---|---|
| Appliances | Gas Range, Oven/Range, Range Hood, Refrigerator, Subzero, Icemaker, Dishwasher, Disposal, Washer, Dryer, Wine Chiller |
| Heating | Hot Air, Natural Gas |
| Cooling | Central Air |
| Fireplace | Yes |
| # of Fireplaces | 3 |
| Has Basement | Yes |
| Basement | Full, Heated, Sump Pump, Fully Finished, Garage Access, Interior Access |
Exterior
| Exterior | Clapboard, Wood |
|---|---|
| Exterior Features | Shed, Porch, Gutters, Garden Area, Lighting, Stone Wall, Underground Sprinkler |
| Lot Description | Fence - Full, Dry |
| Roof | Asphalt Shingle |
| Foundation | Block |
School Information
| Elementary | Kings Highway |
|---|---|
| Middle | Coleytown |
| High | Staples |
Additional Information
| Date Listed | July 3rd, 2026 |
|---|---|
| Days on Market | 8 |
| Zoning | AA |
| RE / Bank Owned | No |
Listing Details
| Office | William Pitt Sotheby's Int'l |
|---|