New
$4,600,000
6 bd · 6.5 ba · 8,185 sqft · 1.00 acre lot
2 Windy Hill Rd, Westport, CT 06880
Single family · Built 2026 · $562/sqft ·
$24,298/mo est. payment
- Garage
- 3 cars
Flood factor 1/10
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.
Facts and features
Bedrooms
- Bedrooms: 6
- Primary Bedroom Level: Upper
- Bedroom 1 Level: Upper
- Bedroom 2 Level: Upper
- Bedroom 3 Level: Upper
- Bedroom 4 Level: Upper
- Bedroom 5 Level: Lower
- Primary Bedroom Features: Cathedral Ceiling,Balcony/Deck,Beams,Fireplace,Full Bath,Walk-In Closet
Other Rooms
- Total Rooms: 14
- Eat-In Kitchen Level: Main
- Eat-In Kitchen Features: 9 ft+ Ceilings, Quartz Counters, Dining Area, Wet Bar, Island, Pantry
- Full Bath Level: Lower
- Rec/Play Room Level: Lower
- Rec/Play Room Features: 9 ft+ Ceilings
- Basement Features: Full, Heated, Fully Finished, Cooled
- Office: Yes
Bathrooms
- Total Bathrooms: 8
- Full Bathrooms: 6
- 1/2 Bathrooms: 2
Interior Features
- Audio system,auto garage door opener,cable - pre-wired,humidifier,open floor plan,security system
Appliances
- Cook top
- Oven/range
- Microwave
- Range hood
- Refrigerator
- Subzero
- Icemaker
- Dishwasher
Heating and Cooling
- Cooling Features: Central Air,Zoned
- Heating Features: Hot Air,Zoned
- Heating Fuel: Natural Gas
- Heating: Yes
- Number of Fireplaces: 2
- Water Heaters: Natural Gas, Tankless Hotwater
Kitchen and Dining
- Dining Room Features: 9 ft+ Ceilings, Built-Ins, Quartz Counters, Dry Bar, Hardwood Floor
- Dining Room Level: Main
Pool and Spa
- Pool Features: Gunite,Heated,In Ground Pool
Schools
- 10
Staples High School
high · 9-12 · 0.9 mi
- 9
Bedford Middle School
middle · 6-8 · 1.1 mi
- 9
Long Lots School
elementary · K-5 · 1.2 mi
Seton Academy
middle · 7-12 · 0.5 mi
- 10
Green's Farms School
elementary · K-5 · 0.9 mi
Landmark Preschool
elementary · PK-K · 1.5 mi
Price history
- Sep 4, 2026 · Listed$4,600,000
- Aug 14, 2026 · Listing Removed—
- Jun 10, 2026 · Listed$4,795,000
- Jul 4, 2025 · Listing Removed—
- Apr 4, 2025 · Relisted$5,100,000
- Apr 2, 2025 · Listing Removed—
- Dec 24, 2024 · Listed$5,100,000
- Sep 20, 2024 · Sold$1,100,000
Tax history
- 2025$10,993 tax · $582,900 assessed
- 2023$10,696 tax · $582,900 assessed
- 2022$10,533 tax · $582,900 assessed
- 2021$10,533 tax · $582,900 assessed
- 2020$9,555 tax · $571,800 assessed
- 2019$9,641 tax · $571,800 assessed
- 2018$9,641 tax · $571,800 assessed
- 2017$9,641 tax · $571,800 assessed
Home value
$4,533,800
- Cotality$4,533,800
- Collateral Analytics$4,554,000
- Quantarium$2,316,979
Where it is
Listed by Jacob Bivona · KELLER WILLIAMS PRESTIGE PROP. · SMARTMLS
