38 Prospect Road, Westport, Connecticut 06880

About this home

A bold expression of sculptural architecture and modern organic design, this one-of-a-kind Green's Farms estate with stone cottage is set on 1.19 artfully layered acres with stacked stone walls, gardens, and striking stone and white stucco facade. Walls of glass flood the interiors with natural light, seamlessly connecting the home to the private grounds with heated pool and spa. Every space is composed with architectural precision, balancing dramatic scale with warmth and livability. The main level features a statement dining room anchored by a dramatic fireplace, sophisticated living room and private office showcasing elevated millwork and custom built-ins, and an expansive family room which extends to a covered outdoor terrace with fireplace, creating an exquisite setting for effortless entertaining and relaxed outdoor living. The kitchen is defined by sleek wood cabinetry, striking natural stone, a curated suite of professional-grade appliances, and a fully appointed scullery. Upstairs, five ensuite bedrooms include a serene primary suite with fireplace, 2 private terraces, dual walk-in closets, and a spa-inspired bath finished in natural stone and refined wood detailing. The finished lower level offers a gym, recreation/game room, media lounge, 6th bedroom, and 1 1/2 baths. Moments from beaches, train, shopping, & dining, this extraordinary residence offers exceptional craftsmanship and an effortless indoor-outdoor lifestyle in Westport's most coveted neighborhood.

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 $4,560,000, ranging $3,879,000 to $5,499,000.

Within a 15-minute walk, sold in the last year
• 49 Hillspoint Road5 bd · 7 ba · 8,550 sq ft · 0.3 mi away
  $4,225,000$494/sq ft2026-06-12
• 11 Wake Robin Road5 bd · 6 ba · 7,583 sq ft · 0.4 mi away
  $4,560,000$601/sq ft2026-08-31
Within about a mile and a half, sold in the last 2 years
• 11 Edgemarth Hill Road6 bd · 7 ba · 7,541 sq ft · 0.2 mi away
  $4,917,500$652/sq ft2025-05-23
• 19 Center Street6 bd · 8 ba · 7,861 sq ft · 0.7 mi away
  $3,879,000$493/sq ft2025-08-15
• 11 Tierney Lane6 bd · 9 ba · 9,550 sq ft · 0.7 mi away
  $5,499,000$575/sq ft2025-10-15

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.

• 9 Over Rock Lane6 bed · 9 bath · 9,200 sq ft$9,860,000
• 11 Manitou Court7 bed · 9 bath · 9,415 sq ft$8,995,000
• 4 Sherwood Island Lane7 bed · 7 bath · 6,215 sq ft$10,500,000
• 11 Dogwood Lane6 bed · 8 bath · 9,100 sq ft$10,650,000
• 10 Beltas Farm Lane6 bed · 8 bath · 9,505 sq ft$8,450,000
• 14 Owenoke Park5 bed · 7 bath · 6,050 sq ft$10,985,000

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