34 Woodside Avenue, Westport, Connecticut 06880

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.

Flood risk: check the FEMA flood map for this address.

Schools

Taxes

Interior

Building & Exterior

Lot & Land

Energy

What it would cost per month

An estimate you can adjust — not a quote, and not an offer of credit. Principal and interest only, plus the taxes and HOA already on this listing. Insurance, PMI and closing costs are not included. Rate seeded at 6.5% (August 2026); change it to whatever your lender quotes.

What's nearby

Distances are straight-line from the property, not driving or walking routes. Places data © OpenStreetMap contributors.

Recent comparable sales

The 5 closest recent sales to this home, nearest match first — same building where possible, then the surrounding streets, widening only when there is nothing closer. These are recorded sale prices from the MLS, not estimates. No automated valuation is shown, because what a home is worth depends on condition, layout and timing that a formula cannot see — call John at 203·883·3399 to read them properly against this home.

5 comparable sales — median $2,199,000, ranging $2,050,000 to $3,100,000.

Within a 15-minute walk, sold in the last year
• 11 Old Hill Road4 bd · 5 ba · 3,935 sq ft · 0.3 mi away
  $2,645,000$672/sq ft2026-02-17
• 19 Old Hill Road4 bd · 3 ba · 3,495 sq ft · 0.3 mi away
  $3,100,000$886/sq ft2025-08-21
• 33 Pequot Trail5 bd · 5 ba · 4,035 sq ft · 0.3 mi away
  $2,100,000$520/sq ft2026-01-07
• 34 Pequot Trail5 bd · 4 ba · 3,782 sq ft · 0.3 mi away
  $2,050,000$542/sq ft2026-08-19
• 60 Sylvan Road North4 bd · 4 ba · 3,430 sq ft · 0.4 mi away
  $2,199,000$641/sq ft2025-11-12

Public record

From the Westport assessor's public property record. These figures describe the property as the town has it on file and can differ from the listing — a finished basement or an addition may not be reflected in the assessor's living area.

More homes in Westport

Closest in price to this one.

• 56 Charcoal Hill Road5 bed · 3 bath · 3,072 sq ft$2,670,000
• 4 Crawford Road5 bed · 4 bath · 4,471 sq ft$2,799,000
• 27 Bauer Pl Extension5 bed · 6 bath · 4,529 sq ft$2,850,000
• 30 Saint Johns Place5 bed · 4 bath · 3,999 sq ft$2,895,000
• 166 Long Lots Road4 bed · 5 bath · 5,629 sq ft$2,995,000
• 4 Bradley Street5 bed · 4 bath · 3,255 sq ft$2,997,000

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