34 High Point Road, Westport, Connecticut 06880

About this home

Refined living awaits on one of Westport's most coveted cul-de-sac settings, nestled within the sought-after Long Lots neighborhood. The exceptional residence unfolds across four finished levels, offering six ensuite bedrooms, two additional half baths, and a thoughtfully designed layout that balances grand scale with everyday functionality. A glass-doored entry introduces interiors defined by opulence and impeccable craftsmanship. Formal living and dining rooms are elegantly appointed, complemented by a butler's pantry for seamless entertaining. The chef's kitchen is both stunning and highly functional. Flowing effortlessly into a sunlit breakfast room and family room with fireplace and wet bar, all have a front row view to the spacious backyard. A private office and well-designed utility room enhance daily living, while direct access to the three-car garage ensures convenience. The second level hosts five beautifully appointed ensuite bedrooms, including a luxurious primary suite complete with fireplace, bespoke walk-in closets, and a spa-inspired bath. An additional study or lounge space provides flexibility for work or relaxation. The third floor offers a sixth ensuite bedroom along with generous bonus space, ideal for guests or extended stays. The finished lower level is designed for recreation and wellness, featuring a media room, gym, game room, and ample storage. Comprised of park-like acre with room for a pool, the property offers both privacy and possibilities.

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

Schools

Taxes

Interior

Building & Exterior

Lot & Land

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 $3,276,000, ranging $1,917,500 to $4,400,000.

Within a 15-minute walk, sold in the last year
• 48 Bayberry Lane6 bd · 6 ba · 6,775 sq ft · 0.2 mi away
  $4,400,000$649/sq ft2026-08-14
• 71 High Point Road5 bd · 4 ba · 6,310 sq ft · 0.4 mi away
  $1,917,500$303/sq ft2026-07-23
• 10 Sprucewood Lane5 bd · 5 ba · 5,526 sq ft · 0.4 mi away
  $3,276,000$592/sq ft2026-06-29
• 119 Long Lots Road5 bd · 5 ba · 5,616 sq ft · 0.5 mi away
  $3,352,000$596/sq ft2026-06-19
• 4 Jennings Court5 bd · 7 ba · 8,110 sq ft · 0.5 mi away
  $3,100,000$382/sq ft2025-11-06

More homes in Westport

Closest in price to this one.

• 2 Windy Hill Road6 bed · 8 bath · 8,185 sq ft$4,600,000
• 1 Twin Oaks Lane5 bed · 7 bath · 8,521 sq ft$4,550,000
• 19 Mortar Rock Road6 bed · 8 bath · 8,190 sq ft$4,699,000
• 159 Easton Road6 bed · 8 bath · 8,594 sq ft$4,450,000
• 22 Evergreen Avenue5 bed · 5 bath · 5,103 sq ft$4,850,000
• 5 Franklin Avenue5 bed · 6 bath · 4,879 sq ft$4,299,000

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