2 Windy Hill Road, Westport, Connecticut 06880

About this home

Resort-style living meets modern luxury at 2 Windy Hill Road. Set on a private landscaped acre, this newly completed 8,100+ SF estate by HOBI Award-winning builder Cypress Development was thoughtfully designed for the way today's luxury buyer lives, entertains, and unwinds. A dramatic two-story foyer introduces light-filled interiors highlighted by soaring ceilings, white oak flooring, natural stone finishes, and walls of European windows and doors. At the heart of the home, the chef's kitchen features marble countertops and backsplash, Sub-Zero and Wolf appliances, custom oak cabinetry, dual dishwashers, and a stunning waterfall island that seamlessly connects to the home's gathering spaces. The primary suite serves as a private retreat with vaulted oak-beamed ceilings, fireplace, sitting area, private balcony overlooking the pool, custom dressing room, and spa-like bath with heated floors and dual showers. Designed for both entertaining and wellness, the lower level includes a glass-enclosed gym, custom marble-topped bar, recreation space, guest suite, and a dedicated area ready for a golf simulator or theater. Outside, enjoy a gunite pool with automatic cover, covered outdoor living area, expansive granite patios, outdoor kitchen provisions, and a large flat lawn surrounded by mature landscaping, stone walls, and privacy plantings. A rare offering that delivers the comfort of everyday living with the amenities of a private resort.

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

Schools

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 $4,000,000, ranging $2,625,000 to $5,250,000.

Within a 15-minute walk, sold in the last year
• 32 Webb Road8 bd · 9 ba · 8,412 sq ft · 0.2 mi away
  $4,100,000$487/sq ft2026-07-15
• 20 Fresenius Road7 bd · 9 ba · 7,105 sq ft · 0.3 mi away
  $4,000,000$562/sq ft2026-08-13
• 19A Darbrook Road6 bd · 8 ba · 7,354 sq ft · 0.6 mi away
  $2,625,000$356/sq ft2026-03-04
• 72 Compo Road North5 bd · 7 ba · 6,302 sq ft · 0.7 mi away
  $3,225,000$511/sq ft2026-07-30
• 19 Twin Circle Drive7 bd · 9 ba · 10,140 sq ft · 0.7 mi away
  $5,250,000$517/sq ft2025-09-16

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.

• 19 Mortar Rock Road6 bed · 8 bath · 8,190 sq ft$4,699,000
• 21 Lockwood Circle6 bed · 7 bath · 6,611 sq ft$4,495,000
• 1 Twin Oaks Lane5 bed · 7 bath · 8,521 sq ft$4,750,000
• 159 Easton Road6 bed · 8 bath · 8,356 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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