2 Windy Hill Road

Westport, CT 06880

$5,100,000
Price
6
Beds
6
Baths
2
1/2 Baths
8,185 Sq. Ft.
$623 / Sq. Ft.
8,185
Sq. Ft.
$623
per Sq. Ft.

Description

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...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!
  1. Listed by Jacob Bivona • Keller Williams Prestige Prop.
    P: (203)-705-8180 C: (203)-705-8180 jbivona.re@gmail.com

Property Details for 2 Windy Hill Road

Basement Description
Full, Heated, Fully Finished, Interior Access
Direct Waterfront
No
Garages Number
3
Neighborhood
In-Town
Style
Colonial, Modern
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 12/24/2024 04:11 PM

Property Details for 2 Windy Hill Road

StatusActive
MLS #24065416
Days on Market3
Taxes-
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built2025
Lot Size1.00 AC / 43,560 SF
CountyFairfield County

Building Information for 2 Windy Hill Road

Stories-Year Built2025Building Size-Lot Size1.00 AC / 43,560 SF

Property Information for 2 Windy Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Roseville to Windy Hill
  • Elementary School: Long Lots
  • High School: Staples
  • Latitude: 41.144214
  • Longitude: -73.339736
  • Middle Jr High School: Bedford
  • Neighborhood Amenities: Commuter Bus, Golf Course, Library, Paddle Tennis, Playground/Tot Lot, Public Rec Facilities, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2024-June 2025
  • Property Tax: $0
Virtual Tour
Interior and Exterior Features
Exterior Features
  • Exterior Features: Gutters, Lighting, Hot Tub, French Doors, Patio, Balcony, Porch, Garden Area, Underground Sprinkler
  • Pool Description: Heated, Spa, In Ground Pool
  • Waterfront Description: Beach Rights, Water Community
Interior Features
  • Appliances Included: Allowance, Cook Top, Oven/Range, Microwave, Range Hood, Refrigerator, Freezer, Dishwasher, Washer, Dryer, Wine Chiller
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air
  • Attic YN: No
  • Fireplaces Total: 2
  • Home Automation: Entertainment System, Lighting, Thermostat(s)
  • Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Sauna, Security System
  • Laundry Room Info: Upper Level
  • Laundry Room Location: Second Floor
  • Rooms Additional: Bonus Room, Foyer, Gym, Laundry Room, Mud Room, Sauna
  • Rooms Total: 14
Room 1
  • Room Entry Order: 1
  • Room Features: 9 ft+ Ceilings,Built-Ins,Fireplace,Patio/Terrace,Sliders,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 2
  • Room Entry Order: 10
  • Room Features: Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 11
  • Room Features: 9 ft+ Ceilings,Entertainment Center
  • Room Level: Lower
  • Room Type: Media Room
Room 4
  • Room Entry Order: 12
  • Room Features: 9 ft+ Ceilings
  • Room Level: Lower
  • Room Type: Rec/Play Room
Room 5
  • Room Entry Order: 13
  • Room Features: 9 ft+ Ceilings
  • Room Level: Lower
  • Room Type: Bedroom
Room 6
  • Room Entry Order: 14
  • Room Level: Lower
  • Room Type: Full Bath
Room 7
  • Room Entry Order: 2
  • Room Features: 9 ft+ Ceilings,Built-Ins,Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 8
  • Room Entry Order: 3
  • Room Features: 9 ft+ Ceilings,Quartz Counters,Dining Area,Wet Bar,Island,Pantry
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 9
  • Room Entry Order: 4
  • Room Features: 9 ft+ Ceilings,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 10
  • Room Entry Order: 5
  • Room Features: 9 ft+ Ceilings,Built-Ins,Hardwood Floor
  • Room Level: Main
  • Room Type: Office
Room 11
  • Room Entry Order: 6
  • Room Features: Vaulted Ceiling,Balcony/Deck,Fireplace,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 12
  • Room Entry Order: 7
  • Room Features: Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 13
  • Room Entry Order: 8
  • Room Features: Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Room 14
  • Room Entry Order: 9
  • Room Features: Full Bath,Walk-In Closet
  • Room Level: Upper
  • Room Type: Bedroom
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Vertical Siding, Wood
  • Foundation Type: Concrete
  • New Construction Type: Under Construction
  • Roof: Metal
  • Year Built: 2025
  • Year Built Source: Owner
  • Bank Owned Property: No
  • Sq Ft Est Heated Below Grade: 2360
Lot Information
  • Lot Description: Some Wetlands, Level Lot, Cleared, Professionally Landscaped
  • Parcel Number: 411794
  • Sq Ft Est Heated Above Grade: 5825.0
  • Sq Ft Total: 8185.0
  • Zoning: AA
Utilities
  • Energy Features: Energy Star Rated, Extra Insulation, Generator Ready, Programmable Thermostat, Thermopane Windows
  • Heat Fuel Type: Natural Gas
  • Hot Water Description: Natural Gas, Tankless Hotwater
  • Sewage System: Public Sewer Connected
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Vacant
Unit 1
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 2
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 3
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 4
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 5
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 6
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 7
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 8
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 9
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 10
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 11
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 12
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 13
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD
Unit 14
  • Listing Key: 29F48609CDE9A04EE063D501100A45DD

Property History for 2 Windy Hill Road

DateEvent & SourcePriceAppreciation
DateEvent & SourcePrice

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 2 Windy Hill Road

Taxable ValueLand$419,000Additions$163,900Total$582,900
Tax Record2023$10,854 ($904 / month)
Home Facts
Beds4Baths3Total Finished SqFt2,144 SqFtAbove Grade Finished SqFt2,144 SqFtStories1Lot Size43,560 SqFtStyleSingle Family ResidenceYear Built1963ZoningAACountyFAIRFIELDAPNWPOR M:E10 L:070-000Fireplace TypeHas Fireplace

Schools near 2 Windy Hill Road

This home is within Westport School District.
Rating
School
Type
Grades
Distance
Long Lots School
Public - K to 5
Bedford Middle School
Public - 6 to 8
Staples High School
Public - 9 to 12
Green's Farms Segregated
Public - 1 to 5
Rating
School
Distance
Long Lots School
PublicK to 5

Bedford Middle School
Public6 to 8

Staples High School
Public9 to 12

Green's Farms Segregated
Public1 to 5

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 2 Windy Hill Road, Westport, CT 06880

2 Windy Hill Road is a single family home for sale in Westport, CT 06880. This property was listed for sale on December 23, 2024 by Keller Williams Prestige Prop., it's currently listed at $5,100,000. It has been on the market for a total of 3 days and was last sold on September 16, 2024. This listing's school district is Westport School District. Nearby schools include Long Lots School, Bedford Middle School and Staples High School. 2 Windy Hill Road is a 6-bed, 7-bath, 8,185 sqft single family home built in 2025.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Keller Williams Prestige Prop., Jacob Bivona

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.