#24053342, John Schiaroli, Listing Office: Coldwell Banker Realty
#24065416·
Listing office: Keller Williams Prestige Prop.·
Listing agent: Jacob Bivona·
Listing office phone: (203) 327-6700
$5,100,000 List price
2 Windy Hill Rd Westport, CT 06880
6 beds
6 full, 2 partial
8,185 sqft
1.0 acres
$623 / sqft
House
Property details
About 2 Windy Hill Rd
Introducing an exceptional new construction by Cypress Development, this luxurious home on a private acre in one of Westport's most sought-after locations seamlessly merges timeless design with modern luxury. Step into an impressive two-story foyer showcasing sun-soaked interiors, hardwood floors, tall ceilings, and meticulous custom millwork. A formal living room and formal dining room set the stage for grand gatherings, while a dedicated home office accommodates today's work-from-home needs. The gourmet kitchen boasts a center island, a separate dining area, and designer finishes-flowing effortlessly into the family room anchored by a fireplace. Walls of glass open to the outdoor entertaining patio, where a pool with spa creates a resort-like escape. Retreat upstairs to a primary suite defined by vaulted ceilings with statement oak beams, a private balcony, a spa-inspired bath, and walk-in closets. 4 additional bedrooms, each with generous closets and en-suite baths, ensure ample privacy. The fully finished lower level caters to recreation and relaxation, featuring a media room, spacious rec area, gym w sauna, bar, and space for a golf simulator. A 6th bedroom and full bath accommodate overnight guests with ease. Built to 2025 energy-efficiency standards, this home has all the features that todays buyer desires. Minutes from Westport's upscale shopping, fine dining, beaches, Longshore, and train, it embodies the pinnacle of modern luxury living. Still time to customize!
Highlights
Home typeOther
HeatingForced Air
StatusActive
CoolingCentral Air, Zoned
Size8,185 sqft
BasementYes
Lot size1 Acres
Year builtNew Const., 2025
ParkingAttached Garage
MLS #24065416
Attached garage3 spaces
WaterfrontBeach, Water Access
Private poolYes
Summary
- Partial Bathrooms: 2
- Full Bathrooms: 6
- Appliances: Cooktop, Oven/Range, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Wine Cooler
- Basement: Yes
- Interior: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Sauna, Security System
- Total Bedroom Count: 6
- Garage Space: 3 spaces
- Attached Garage: Yes
- Private Pool: Yes
- Parking: Attached Garage
- Waterfront: Beach, Water Access
- Exterior: Gutters, Lighting, Hot Tub, French Doors, Patio, Balcony, Porch, Garden Area, Underground Sprinkler
- Architectural Style: Colonial
- Heating: Forced Air
- Cooling: Central Air, Zoned
- List Price: $5,100,000
- Price/SqFt: $623
- Annual Tax Amount: $10,854
- Tax Year: 2024
- Lot: Wetlands, Level, Cleared, Landscaped
- Directions: Roseville to Windy Hill
- Year Built: 2025
- Living Area: 8,185 SqFt
- Lot Size: 1 Acres
- MLS Number: 24065416
- Office Name: Keller Williams Prestige Prop.
- Office Phone: (203) 327-6700
- Office Email: jbivona.re@gmail.com
- Listing Agent: Jacob Bivona
Copyright © 2025 Smart MLS. The data relating to real estate for sale on this website appears in part through the SMARTMLS Internet Data Exchange program, a voluntary cooperative exchange of property listing data between licensed real estate brokerage firms, and is provided by SMARTMLS through a licensing agreement. Listing information is from various brokers who participate in the SMARTMLS IDX program and not all listings may be visible on the site. The property information being provided on or through the website is for the personal, non-commercial use of consumers and such information may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Some properties which appear for sale on the website may no longer be available because they are for instance, under contract, sold or are no longer being offered for sale. Property information displayed is deemed reliable but is not guaranteed.
Data displayed may be a portion of, and not a complete set of all listings published in the MLS.
Last updated on: 5/14/2025, 3:20:30 AM Eastern. If you have any questions regarding the accuracy of this data, please contact us at help@rockethomes.com.
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$5,100,000
2 Windy Hill Rd
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Price information
Property sales
| Date | Event | Price |
|---|---|---|
| Sep 20, 2024 | Home Sold | $1,100,000 |
| Jul 13, 2007 | Home Sold | $750,000 |
Tax history
| Year | Assessment | Property Tax |
|---|---|---|
| 2024 | $582,900 | $10,854 |
| 2023 | $582,900 | $10,696 |
| 2022 | $582,900 | $10,533 |
| 2021 | $582,900 | $10,533 |
| 2020 | $571,800 | $9,555 |
| 2019 | $571,800 | $9,641 |
History based on county public records data.
Nearby schools
9
Green's Farms Elementary School
Public District KG-5
0.9 mi
•17 Morningside Dr S
9
Long Lots Elementary School
Public District KG-5
1.2 mi
•13 Hyde Ln
9
Saugatuck Elementary School
Public District KG-5
1.5 mi
•170 Riverside Ave
School ratings are a score out of 10, where 10 is the highest and 1 is the lowest.
Neighborhood
The neighbors living near this home have an average income of $155,102. The majority of Westport, CT residents have income $200k+ annually. Typical family type is married, with kids. Typical level of education for residents in this area is post secondary degree.
How much money do the neighbors make?
6%
<35k
25%
35k-100k
30%
100k-200k
39%
200k+
What level of education do the neighbors have?
High School Diploma
Post Secondary Degree
Masters Degree
Doctorate
What types of families live nearby?
27%
Single, No Kids
7%
Single, with Kids
28%
Married, No Kids
38%
Married, with Kids
Are the neighbors home owners or renters?
Home Owners
Renters
How old are people in this area?
20%
<11 yrs old
12%
12-17 yrs old
7%
18-34 yrs old
45%
35-64 yrs old
16%
65+ yrs old
What do the neighbors do for fun?
Skiing/snowboarding
Men's Tennis- Tennis
Where do the neighbors shop?
Nordstrom
Bloomingdales
Brooks Brothers
Where do the neighbors go to eat?
California Pizza Kitchen
Bonefish Grill
Qdoba
What do the neighbors drive?
BMW
Lexus
Acura
What do the neighbors listen to?
Talk/Personality
News
Sports
All data provided by Home Junction and Claritas
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Frequently asked questions
Living in Westport, CT
Westport's transportation infrastructure includes a well-connected network of roads, with easy access to major highways that facilitate travel to nearby cities. The town also has a train station that provides regular commuter service to New York City and other destinations. Public transportation options are available, with bus services connecting Westport to surrounding areas. The town is also bike-friendly, with several paths and lanes designated for cyclists, and it features walkable neighborhoods, particularly in the downtown area.
The community benefits from a robust educational system, including several public schools known for their academic excellence, as well as private institutions that cater to a range of educational needs. Westport's healthcare services are comprehensive, with facilities offering a variety of medical specialties. The town also features a public library system that serves as a resource and gathering place for residents. Retail and dining options in Westport reflect the local culture, with a mix of boutique shops and restaurants that range from casual eateries to upscale dining experiences.
Westport is celebrated for its coastal charm and artistic heritage, with a community that prides itself on a rich cultural scene. The town's character is further enhanced by its vibrant arts community, numerous galleries, and the annual Westport Fine Arts Festival, which showcases local and national artists. The presence of the Westport Country Playhouse adds to the town's reputation as a hub for the performing arts.
Westport's housing market is characterized by a diverse array of options, with a significant emphasis on single-family homes that exhibit a blend of colonial, contemporary, and Cape Cod architectural styles. The area also offers a selection of condominiums and townhouses, providing alternatives to the traditional detached home. The majority of Westport's residential buildings were constructed during a period of growth in the mid-20th century, with many homes featuring waterfront views and spacious lots.
About 2 Windy Hill Rd
The listing price of 2 Windy Hill Rd property is $5,100,000.
The property 2 Windy Hill Rd is a house located in Westport, Connecticut, 06880.
Active Listing: 2 Windy Hill Rd is For Sale (Active/New) which means the seller is accepting offers.
The nearby schools for 2 Windy Hill Rd are: Green's Farms Elementary School (GreatSchools Rating 9/10), Long Lots Elementary School (GreatSchools Rating 9/10), Saugatuck Elementary School (GreatSchools Rating 9/10), Bedford Middle School (GreatSchools Rating 9/10), Coleytown Middle School (GreatSchools Rating 9/10), Nathan Hale Middle School (GreatSchools Rating 5/10), Staples High School (GreatSchools Rating 10/10), Norwalk High School (GreatSchools Rating 3/10), Fairfield Ludlowe High School (GreatSchools Rating 9/10).
According to the records, the last property tax for 2024 is $10,854 (source: MLS/based on county public records data).
The last sale was on September 20, 2024 for $1,100,000 (source: MLS/tax record).
The property at 2 Windy Hill Rd has 6 bedrooms and 6 full and 2 half bathrooms.
The property 2 Windy Hill Rd is 8,185 SqFt (source: MLS/tax record).
The year of construction for 2 Windy Hill Rd is 2025.
This home is located at 2 Windy Hill Rd in Westport, CT and zip code 06880. This 8,185 square foot home, which was built in 2025, sits on a 1.00 acre lot. Features: 6 bedrooms, 8 bathrooms. It has been listed on Rocket Homes since December 24, 2024 and is currently priced at $5,100,000.
Over 10 listings were sold over their listed price in April 2025 in Westport, CT. In the same period over 14 listings were sold below the listed price and 2 listings were sold for the listed price. The inventory of homes for sale in Westport, CT between March and April 2025 increased by 34.6%. Listings spent 206 days on the market in April 2025, and had a median list price of $1,946,846 during the same period.
From Rocket Homes Real Estate and based on county public records data.