Westport, CT / SOLD

5 High Point RoadWestport, CT 06880

The buyer could have saved $53,125 in brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 50% rebate. Actual savings depend on final purchase price and commission received. Based on the recorded closed price; this is a hypothetical estimate, not a statement of actual commission or rebate paid.

Sale Price$4,250,000ClosedJune 29, 2025

5 High Point Road — exterior photo
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Estimated buyer rebate

The buyer could have saved $53,125 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

See how the commission rebate works ↗

*Estimate assumes a 2.5% buyer-agent commission and a 50% rebate. Actual savings depend on final purchase price and commission received. Based on the recorded closed price; this is a hypothetical estimate, not a statement of actual commission or rebate paid.

At a glance

Closed · MLS #24081110
Bedrooms
5
BathroomsBaths
5 full / 2 half
Square feet
8,835
Year built
2007
Acres
1.06
Property taxes
$30,825

July 2024-June 2025

Read the full listing description

Set on a pristine, level acre on one of Westport's most popular cul-de-sacs, this exquisite stone & shingle home combines timeless craftsmanship with modern luxury. Featuring 9' & 10' ceilings, extensive millwork, and five fireplaces with custom mantles, the home is built for elegant living and entertaining throughout nearly 9000sqft. The main level offers a chef's kitchen that flows into a warm family room with a stone fireplace and French doors to the patio, a cherry-paneled study, formal living room with marble fireplace, and a dining room that easily seats 20. Upstairs are five spacious bedrooms and four full baths, including a luxurious primary suite with 12ft ceilings, a fireplace and an oversized double shower with steam. A large playroom offers a potential in-law/au pair suite with its own bedroom and full bathroom. The finished walkout lower level includes a media room with large screen, gym, games room, a second family room with a fireplace, and full bath. The walk-up attic offers approx. 1500 sq ft for future expansion. Outside, enjoy a private backyard oasis with a heated 20x50 Gunite pool and spa (2018), new stone walls and planting beds, patio with wood-burning fireplace, and professionally landscaped evergreens and ornamentals for privacy. High Point Road is a mile-long cul-de-sac that feels like its own neighborhood, uniquely within walking distance to all three schools: award-winning Staples HS, Bedford Middle, and Long Lots Elem. Book your showing today!

Schools

Elementary
Long Lots
Middle
Bedford
High
Staples

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

Price history

DateEventPrice
Closed price$4,250,000
Original list price$3,950,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $4,250,000 closed price × assumed 2.5% buyer-agent commission × 50% rebate = $53,125. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered or actual compensation. This is a hypothetical estimate, not a rebate paid on this sale.

Listed by William Raveis Real Estate

Amy Swanson

SmartMLS · Listing #24081110 · Closed

Listing data checked: Sep 25, 2026, 5:35 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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