2 Windy Hill Road
Westport, CT, 06880 $ 4,795,000
Bedrooms6 Baths6.2 Sq 8,185 Monthly Estimate*
$ 29,524
for $4,795,000 with 6 bedrooms and 6 full baths, 2 half baths. This 8,185 square foot home was built in 2026 on a lot size of 1.
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. Additional photos coming soon. Showings start June 18, 2026.
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Single Family Coming Soon
FeaturesGeneralZoning AA
Neighborhood Long Lots
County Fairfield
Tax Year July 2025-June 2026
Property Type Single Family For Sale
Status Coming Soon
Acres 1
Directions Roseville rd to Windy Hill rd
High School Staples
City Westport
Elementary School Long Lots
Sq Ft Total 8185
Year Built 2026
Style Colonial Modern
Year Built Source Owner
Pool Description Gunite Heated In Ground Pool
Energy Features Home Energy Rating Generator Ready
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InteriorCooling System Central Air Zoned
Total Rooms 14
Basement Description Full Heated Fully Finished
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ExteriorWater Source Public Water Connected
Lot Description Fence - Partial Level Lot On Cul-De-Sac Professionally Landscaped
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* Excluded FeaturesList ByJacob BivonaListing Agent
Keller Williams Prestige Prop.Broker
jbivona.re@gmail.comEmail
Affordability Calculator
- Monthly Principal & Interest
- $29,524
- Monthly Property Taxes
- --
- Monthly Home Insurance
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Default based on a 30-year fixed rate of 6.25% with 20% down. The estimated payment is offered for convenience and is not an offer of credit. Due to market fluctuations, interest rates are subject to change at any time and without notice. Your individual rate may vary. Rates may differ for FHA, VA or jumbo loans.
Learn more about how to save NearbySingle family listings in Westport, CT
Average List Price $3,910,333
Percent of Sale Price 18%
About Westport, CT 26,742 Population
4% Since 2002
$ 169,979 Median Income
48.33 Median Age
40% Households with Children
Trends Information provided by ATTOM Data Solutions.
3041933 Elementary School
1967866 Middle School
Staples High School High School
Pricing History| Date | Price | Price Change | Description |
|---|
| 6/10/2026 | $4,795,000 | | Listed Price |