8 Windy Hill Rd

Redding, CT 06896

$1,195,000
Price
4
Beds
3,907 Sq. Ft.
$306 / Sq. Ft.
3,907
Sq. Ft.
$306
per Sq. Ft.
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Listed By CompassOpen: 5/2 01:00PM - 03:00PM
Listed By CompassOpen: 5/2 01:00PM - 03:00PM

Description

Set on over 2 private acres in a coveted neighborhood in SW Redding, this sun-filled 4 BR Colonial blends timeless style, scale and effortless living. Designed for both entertaining and daily life, the main level centers around a spacious EIK w/center island, all-new appliances and seamless flow to the adjoining family room w/gas fireplace. Sliders open to the deck and grounds beyond, creating an easy indoor-outdoor flow. A formal dining room is ideal for gatherings, while a second living room w/fireplace...Set on over 2 private acres in a coveted neighborhood in SW Redding, this sun-filled 4 BR Colonial blends timeless style, scale and effortless living. Designed for both entertaining and daily life, the main level centers around a spacious EIK w/center island, all-new appliances and seamless flow to the adjoining family room w/gas fireplace. Sliders open to the deck and grounds beyond, creating an easy indoor-outdoor flow. A formal dining room is ideal for gatherings, while a second living room w/fireplace provides an inviting retreat. A dedicated home office with a wall of custom built-ins & a powder room complete the main floor. Upstairs, the expansive primary suite is a sanctuary, featuring dual walk-in closets and a large bath w/soaking tub. 3 additional bedrooms share an updated hall bath, while 2nd floor laundry adds convenience. The finished lower level adds versatility with a spacious recreation/media room, dedicated gym & half bath. Outside, the property truly shines. A level, usable yard is anchored by a heated gunite saltwater pool w/travertine surrounds, creating a private resort-like setting for summer entertaining and quiet afternoons. The charming barn has outstanding potential to become a pool house or studio. Minutes from Route 7, downtown Ridgefield, MetroNorth, and Topstone Park, this home delivers the rare combination of neighborhood living, privacy and convenience, just in time for summer.

Listing Agent

  1. Brianna Carvalho

    Brianna Carvalho

    Listing Agent

    Compass

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Property Details for 8 Windy Hill Road

Basement Description
Full, Fully Finished
Direct Waterfront
No
Expected Active Date
05-01-2026
Garages Number
2
Neighborhood
Umpawaug
Style
Colonial
Garage Parking Info
Attached Garage
Swimming Pool
Yes

Open Houses

Saturday, May 2nd1:00 PM - 3:00 PM
PublicView contact
Sunday, May 3rd1:00 PM - 3:00 PM
PublicView contact
LISTING UPDATED: 05/01/2026 04:05 AM

Property Details for 8 Windy Hill Road

StatusActive
MLS #24171032
Days on Market1
Taxes$18,126 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1998
Lot Size2.29 AC / 99,752 SF
CountyFairfield County
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Location

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Building Information for 8 Windy Hill Road

Stories-Year Built1998Building Size-Lot Size2.29 AC / 99,752 SF

Payment Calculator

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$7,528 per month

30 year fixed, 6.46% Interest

Principal and Interest

$6,017

Property Taxes

$1,511

HOA Dues

$0

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Property Information for 8 Windy Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Route 7 to Old Redding Road, Right on Windy Hill
  • Elementary School: Redding
  • High School: Joel Barlow
  • Latitude: 41.2911
  • Longitude: -73.42459
  • Middle Jr High School: John Read
  • Neighborhood Amenities: Golf Course, Health Club, Lake, Library, Park, Playground/Tot Lot, Shopping/Mall
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $18,126
Interior and Exterior Features
Exterior Features
  • Exterior Features: Barn, Deck, Garden Area, Patio
  • Pool Description: Gunite, Heated, Salt Water, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Cook Top, Wall Oven, Refrigerator, Dishwasher
  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Audio System, Auto Garage Door Opener, Central Vacuum, Security System
  • Laundry Room Info: Upper Level
  • Rooms Additional: Gym
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 13.0
Room 2
  • Room Entry Order: 10
  • Room Features: Wall/Wall Carpet
  • Room Length: 32.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 13.0
Room 3
  • Room Entry Order: 11
  • Room Features: Half Bath,Wall/Wall Carpet
  • Room Length: 23.0
  • Room Level: Lower
  • Room Type: Media Room
  • Room Width: 13.0
Room 4
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 13.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 15.0
Room 5
  • Listing Key: 508BDF487EC1521CE063E201100A7B71
  • Room Entry Order: 3
  • Room Features: Balcony/Deck,Breakfast Nook,Granite Counters,Dining Area,Island,Sliders
  • Room Length: 20.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 15.0
Room 6
  • Room Entry Order: 4
  • Room Features: Balcony/Deck,Dining Area,Fireplace,Hardwood Floor,Sliders
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 24.0
Room 7
  • Room Entry Order: 5
  • Room Features: Book Shelves,Built-Ins,Hardwood Floor
  • Room Length: 11.0
  • Room Level: Main
  • Room Type: Office
  • Room Width: 14.0
Room 8
  • Room Entry Order: 6
  • Room Features: Double-Sink,Full Bath,Walk-In Closet,Wall/Wall Carpet
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Primary Bedroom
  • Room Width: 24.0
Room 9
  • Listing Key: 508BDF487EC1521CE063E201100A7B71
  • Room Entry Order: 7
  • Room Features: Wall/Wall Carpet
  • Room Length: 15.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 13.0
Room 10
  • Room Entry Order: 8
  • Room Features: Wall/Wall Carpet
  • Room Length: 11.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 16.0
Room 11
  • Room Entry Order: 9
  • Room Features: Wall/Wall Carpet
  • Room Length: 10.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Property
Property and Assessments
  • Color: Taupe
  • Construction Description: Frame
  • Exclusions: Washer & dryer, microwave, deep freezer, grill, window treatments and curtain rods. Please see attached Exclusion list for details.
  • Exterior Siding: Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1998
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Est Heated Below Grade: 900
  • Living Area SQFT Per Public Records: 3007
Lot Information
  • Lot Description: Fence - Full, Level Lot, Professionally Landscaped
  • Parcel Number: 271729
  • Sq Ft Est Heated Above Grade: 3007.0
  • Sq Ft Total: 3907.0
  • Zoning: R-2
Utilities
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: Yes
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 8 Windy Hill Road

DateEvent & SourcePriceAppreciation
Aug 15, 2022

Closed (Public Record)

Public Record #1496078080

$1,025,000

+1.0% / yr

Nov 6, 2006

Closed (Public Record)

Public Record #210475535

$875,000—
DateEvent & SourcePrice
08/15/2022

Closed (Public Record)

Public Record #1496078080

$1,025,000

+1.0% / yr

11/06/2006

Closed (Public Record)

Public Record #210475535

$875,000

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

Public Records for 8 Windy Hill Road

Taxable ValueLand$171,600Additions$442,000Total$613,600
Tax Record2024$18,126 ($1,510 / month)
Home Facts
Beds4Baths3Total Finished SqFt3,007 SqFtAbove Grade Finished SqFt3,007 SqFtStories2Lot Size99,752 SqFtStyleSingle Family ResidenceYear Built1998ZoningR-2CountyFAIRFIELDAPNREDD M:28 L:49Fireplace TypeHas Fireplace

Schools near 8 Windy Hill Road

This home is within Redding School District.
Rating
School
Type
Grades
Distance
Redding Elementary School
Public - PK to 4
John Read Middle School
Public - 5 to 8
Joel Barlow High School
Public - 9 to 12
Rating
School
Distance
Redding Elementary School
PublicPK to 4

John Read Middle School
Public5 to 8

Joel Barlow High School
Public9 to 12

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 8 Windy Hill Road, Redding, CT 06896

8 Windy Hill Road is a single family home for sale in Redding, CT 06896. This property was listed for sale on April 29, 2026 by Compass, it's currently listed at $1,195,000. It has been on the market for a total of 1 days and was last sold on August 15, 2022. This listing's school districts are Redding School District, Regional School District 09. Nearby schools include Redding Elementary School, John Read Middle School and Joel Barlow High School. 8 Windy Hill Road is a 4-bed, 4-bath, 3,907 sqft single family home built in 1998.

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, Inc., its subsidiaries, affiliates and their agents and associated third parties 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, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

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.