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2 Windy Hill Road

Westport, CT 06880
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Bed 6

Bed

Bath 8

Bath

SqFt8,185

Sqft

Acres1

Acre(Lot)

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.

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Detail Ic Property Details

Property Type : Residential

Price : $4,795,000

AD Id : 82921075

MLS Id : 24182984

Beds : 6

Lot Size : 1 Acre

Living Area Size : 8,185

Year Built : 2026

Garage : 3

County : Fairfield

  • Map Map

Map

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Feature Features

  • Bedroom Information

    Total beds: 6

    Bathroom Information

    Total Baths: 8 Full Baths: 6 Half Baths: 2

    Room Information

    Rooms Total: 14 Has Basement: Yes Basement: Full, Finished
  • Roofing Information

    Metal
  • Interior Features

    Sound System, Entrance Foyer, Open Floorplan Roof: Metal Appliances: Cooktop, Dishwasher, Dryer, Ice Maker, Microwave, Range, Oven, Refrigerator, Washer, Gas Water Heater, Humidifier, Range Hood, Wine Cooler Laundry Features: Laundry Room
  • Heating & Cooling

    Has Heating: Yes Heating: Natural Gas, Forced Air, Zoned Has Cooling: Yes Cooling: Central Air, Zoned

  • Building Information

    Year Built: 2026 Building Area Total: 8185 Construction Materials: Wood Siding, Frame, Vertical Siding Patio And Porch Features: Patio Pool Features: Gunite, Heated, Outdoor Pool, In Ground Private Pool: No
  • Exterior Features

    Exterior Features: Balcony

  • Lot Information

    Lot Size Acres: 1 Lot Description: Level, Cul-De-Sac

  • Listing Price Information

    Listing Price: $4795000

  • Tax Information

    Parcel Number: 411794

  • Parking Information

    Garage Door Opener, Attached

    Garage Information

    Has Garage: Yes Has Attached Garage: Yes Garage Space: 3

  • School Information

    Elementary School: Long Lots
    Junior High School: Bedford
    Senior High School: Staples
  • Location Information

    Direction: Roseville rd to Windy Hill rd WaterSource: Public Security Features: Security System
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Nearby Home Value

Address Estimate Bed Bath Sq. Ft Lot Size
Clapboard Hill Road #NE.., Westport, CT, 06880 $7,926,000 6 7 7,200 7,200 SqFt
10 Grist Mill Lane, Westport, CT, 06880 $1,689,000 3 3 2,138 2,138 SqFt
28 Bulkley Avenue, Westport, CT, 06880 $2,500,000 5 5 3,917 3,917 SqFt
69 Beachside Avenue, Westport, CT, 06880 $7,350,000 6 7 6,585 6,585 SqFt
36 Maple Avenue, Westport, CT, 06880 $5,199,000 6 7 2,448 2,448 SqFt
61 Clapboard Hill Road, Westport, CT, 06880 $3,850,000 4 4 3,418 3,418 SqFt
11 Beachside Common, Westport, CT, 06880 $22,825,000 8 10 9,439 9,439 SqFt
25 Old Road, Westport, CT, 06880 $2,200,000 5 5 4,474 4,474 SqFt
22 Sturges Commons, Westport, CT, 06880 $3,500,000 5 8 4,911 4,911 SqFt
11 Clapboard Hill Road, Westport, CT, 06880 $3,995,000 6 8 5,628 5,628 SqFt

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed.

ByOwner last updated this listing 06/12/2026 @ 21:56

MLS: 24182984 LISTED BY: Jacob Bivona, Keller Williams Prestige Prop. SOURCE: SmartMLS

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