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.
Coming soon 06/18
$4,795,000
2 Windy Hill Road, Westport, CT 06880
6beds
8,185sqft
Single Family Residence
Built in 2026
1 Acres Lot
$-- Zestimate®
$586/sqft
$-- HOA
What's special
- 2 days |
- 704 |
- 29 |
Zillow last checked:
Listing updated:
Listed by:
Jacob Bivona (203)705-8180,
Keller Williams Prestige Prop. 203-327-6700,
Wendy Ryan 203-964-7450,
Brown Harris Stevens
Source: Smart MLS,MLS#: 24182984
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Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 6
- Bathrooms: 8
- Full bathrooms: 6
- 1/2 bathrooms: 2
Rooms
- Room types: Bonus Room, Gym, Laundry
Primary bedroom
- Features: Cathedral Ceiling(s), Balcony/Deck, Beamed Ceilings, Fireplace, Full Bath, Walk-In Closet(s)
- Level: Upper
Bedroom
- Features: Full Bath, Walk-In Closet(s)
- Level: Upper
Bedroom
- Features: Full Bath, Walk-In Closet(s)
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Walk-In Closet(s)
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Walk-In Closet(s)
- Level: Upper
Bedroom
- Features: High Ceilings, Walk-In Closet(s)
- Level: Lower
Bathroom
- Level: Lower
Dining room
- Features: High Ceilings, Built-in Features, Quartz Counters, Dry Bar, Hardwood Floor
- Level: Main
Family room
- Features: High Ceilings, Built-in Features, Fireplace, Patio/Terrace, Sliders, Hardwood Floor
- Level: Main
Kitchen
- Features: High Ceilings, Quartz Counters, Dining Area, Wet Bar, Kitchen Island, Pantry
- Level: Main
Living room
- Features: High Ceilings, Hardwood Floor
- Level: Main
Media room
- Features: High Ceilings, Entertainment Center
- Level: Lower
Office
- Features: High Ceilings, Hardwood Floor
- Level: Main
Rec play room
- Features: High Ceilings
- Level: Lower
Heating
- Forced Air, Zoned, Natural Gas
Cooling
- Central Air, Zoned
Appliances
- Included: Cooktop, Oven/Range, Microwave, Range Hood, Refrigerator, Subzero, Ice Maker, Dishwasher, Washer, Dryer, Wine Cooler, Gas Water Heater, Tankless Water Heater, Humidifier
- Laundry: Upper Level
Features
- Sound System, Wired for Data, Open Floorplan, Entrance Foyer, Smart Thermostat, Wired for Sound
- Doors: French Doors
- Basement: Full,Heated,Finished
- Attic: Pull Down Stairs
- Number of fireplaces: 2
Interior area
- Total structure area: 8,185
- Total interior livable area: 8,185 sqft
- Finished area above ground: 5,825
- Finished area below ground: 2,360
Property
Parking
- Total spaces: 3
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 3
Features
- Patio & porch: Patio
- Exterior features: Balcony, Rain Gutters, Lighting, Underground Sprinkler
- Has private pool: Yes
- Pool features: Gunite, Heated, In Ground
- Fencing: Partial
Lot
- Size: 1 Acres
- Features: Level, Cul-De-Sac, Landscaped
Details
- Parcel number: 411794
- Zoning: AA
- Other equipment: Generator Ready
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Modern
- Property subtype: Single Family Residence
Materials
- Vertical Siding, Wood Siding
- Foundation: Concrete Perimeter
- Roof: Metal
Condition
- Completed/Never Occupied
- Year built: 2026
Details
- Warranty included: Yes
Utilities & green energy
- Sewer: Public Sewer
- Water: Public
Green energy
- Green verification: Home Energy Score
Community & HOA
Community
- Features: Near Public Transport, Golf, Health Club, Library, Playground, Public Rec Facilities, Shopping/Mall
- Security: Security System
- Subdivision: Long Lots
HOA
- Has HOA: No
Location
- Region: Westport
Financial & listing details
- Price per square foot: $586/sqft
- Tax assessed value: $582,900
- Annual tax amount: $10,993
- Date on market: 6/10/2026
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 7/3/2025 | Listing removed | $5,100,000$623/sqft |
Source:  Smart MLS #24065416 Report a problem | ||
| 12/24/2024 | Listed for sale | $5,100,000+363.6%$623/sqft |
Source: Smart MLS #24065416 Report a problem | ||
| 9/20/2024 | Sold | $1,100,000+46.7%$134/sqft |
Source: Public Record Report a problem | ||
| 7/13/2007 | Sold | $750,000$92/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $10,993 +1.3% | $582,900 |
| 2024 | $10,854 +1.5% | $582,900 |
| 2023 | $10,696 +1.5% | $582,900 |
| 2022 | $10,533 | $582,900 |
| 2021 | $10,533 +10.2% | $582,900 +1.9% |
| 2020 | $9,555 -0.9% | $571,800 |
| 2019 | $9,641 | $571,800 |
| 2018 | $9,641 | $571,800 |
| 2017 | $9,641 | $571,800 |
| 2016 | $9,641 | $571,800 |
Find assessor info on the county website
Monthly payment
Est. payment$--/mo
Payment breakdown
Explore the cost of this home by adjusting the details. Changes won't be saved.All calculations are estimates and provided by Zillow, Inc. for informational purposes only. Actual amounts may vary.
HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: Staples
Nearby schools
GreatSchools rating
- 9/10Long Lots SchoolGrades: K-5Distance: 1.2 mi
- 9/10Bedford Middle SchoolGrades: 6-8Distance: 1.1 mi
- 10/10Staples High SchoolGrades: 9-12Distance: 0.9 mi
Schools provided by the listing agent
- Elementary: Long Lots
- Middle: Bedford
- High: Staples
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Fairfield County
- Westport
- 06880
- Staples
- 2 Windy Hill Road
Nearby cities
Nearby neighborhoods
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