14 High Point Road, Westport, Connecticut 06880

About this home

Classic Colonial 5 Bedroom 5 - 1/2 Bath set on over 1 acre with a Gunite Swimming Pool on Westport's longest and perhaps, most sought after Cul-De-Sac! Almost 4700 sq ft on 1st & 2nd floors (hardwood flooring throughout), Plus 1400 sq ft in the fully finished, daylight, walk-out lower level. On the Main level the Gracious Living Room with Fireplace & Box Bay Window, is so large it easily accommodates the grand piano. Stroll through the Cocktail Lounge with built-ins, wet-bar & wine fridge to the delightful sunny, oversized Dining Room with dozens of windows & French Doors that lead to the rear deck. Circle back to the large Eat-In Kitchen with Island that seats four and a dedicated Dining Area by the Bay Window, this all seamlessly flows into the Family Room with Fireplace, Built-In Bookshelves and French Doors opening to the rear deck with views of the pool below. Rounding out the first floor are a Home Office, Ensuite Guest Bedroom with a Full Bath and Walk-In Closet, Half Bath in hall. The 2nd floor has an Enormous Primary Suite with Spa Bath, 3 Walk-In closets & Office or Dressing Room attached to the suite. The 2nd level has 3 more spacious family bedrooms, including one with an ensuite bath and walk-in closet and two more that have ample closet space and share a hall bath. The daylight, walkout lower level has a full bath, tv/media room, gym/playroom with sink, d/w, and fridge and a bonus storage room. Generac Generator! Walls freshly painted! Newer -Roof, HVAC, Septic!

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 $3,352,000, ranging $2,650,000 to $4,400,000.

Within a 15-minute walk, sold in the last year
• 1 Angora Road5 bd · 5 ba · 4,628 sq ft · 0.1 mi away
  $2,650,000$572/sq ft2026-07-15
• 119 Long Lots Road5 bd · 5 ba · 5,616 sq ft · 0.2 mi away
  $3,352,000$596/sq ft2026-06-19
• 48 Bayberry Lane6 bd · 6 ba · 6,775 sq ft · 0.3 mi away
  $4,400,000$649/sq ft2026-08-14
• 10 Sprucewood Lane5 bd · 5 ba · 5,526 sq ft · 0.4 mi away
  $3,276,000$592/sq ft2026-06-29
• 1 Greystone Farm Lane5 bd · 6 ba · 5,182 sq ft · 0.4 mi away
  $4,199,000$810/sq ft2026-06-30

More homes in Westport

Closest in price to this one.

• 166 Long Lots Road4 bed · 5 bath · 5,629 sq ft$2,995,000
• 7 Webb Road6 bed · 5 bath · 5,506 sq ft$2,995,000
• 142 Easton Road5 bed · 6 bath · 7,192 sq ft$2,950,000
• 12 Murvon Court4 bed · 3 bath · 2,234 sq ft$2,900,000
• 4 Bradley Street5 bed · 4 bath · 3,255 sq ft$2,885,000
• 4 Surrey Lane5 bed · 4 bath · 3,571 sq ft$2,795,000

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