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$1,195,000 Just Listed

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 2 Full Baths
  • 2 Partial Baths
  • 3,907 Sq. Ft.
  • 2 Car Garage
  • Updated 4 hours ago

Next open house:

Open House: 1:00 PM - 3:00 PM

Saturday 5/2 1:00 PM - 3:00 PM

8 Windy Hill Road,Redding, CT 06896

8 Windy Hill RoadReddingCT06896

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Join us at 8 Windy Hill Road on:

  • Open House: 1:00 PM - 3:00 PM

    Sunday 5/3 1:00 PM - 3:00 PM

    8 Windy Hill Road,Redding, CT 06896
    8 Windy Hill RoadReddingCT06896
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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.

Full Property Details for 8 Windy Hill Rd

General

  • Price: $1,195,000
  • Taxes: (July 2025-June 2026)
  • Status: Active
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24171032
  • Updated: Today (5/1/2026)
  • Added to Site: Today

Interior

  • Number of Rooms: 9
  • Rooms/Areas: Gym
  • Interior Features: Audio System, Auto Garage Door Opener, Central Vacuum, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 2
  • Appliances: Cook Top, Wall Oven, Refrigerator, Dishwasher

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 2
  • Half Bathrooms: 2

Bedrooms

  • Total Bedrooms: 4
  • Primary Bedroom: Primary Bedroom - Double-Sink, Full Bath, Walk-In Closet, Wall/Wall Carpet, 14 x 24, Upper
  • Bedroom 1: Bedroom - Wall/Wall Carpet, 10 x 12, Upper
  • Bedroom 2: Bedroom - Wall/Wall Carpet, 11 x 16, Upper
  • Bedroom 3: Bedroom - Wall/Wall Carpet, 15 x 13, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, 17 x 13, Main
  • Family Room: Family Room - Balcony/Deck, Dining Area, Fireplace, Hardwood Floor, Sliders, 14 x 24, Main
  • Kitchen: Kitchen - Balcony/Deck, Breakfast Nook, Granite Counters, Dining Area, Island, Sliders, 20 x 15, Main
  • Dining Room: Dining Room - Hardwood Floor, 13 x 15, Main
  • Office: Office - Book Shelves, Built-Ins, Hardwood Floor, 11 x 14, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Wall/Wall Carpet, 32 x 13, Lower
  • Rec Room: Wall/Wall Carpet, 32 x 13, Lower
  • Theater/Media: Media Room - Half Bath, Wall/Wall Carpet, 23 x 13, Lower
  • Laundry: Upper Level

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Salt Water, In Ground Pool

Exterior

  • Exterior Features: Barn, Deck, Garden Area, Patio
  • Color: Taupe

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 2
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Umpawaug
  • Driving Directions: Route 7 to Old Redding Road, Right on Windy Hill

School Information

  • Elementary School: Redding
  • Middle School: John Read
  • High School: Joel Barlow

Community

  • Community Name: Umpawaug

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Domestic

Utilities

  • Sewer: Septic
  • Water: Private Well

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Wood
  • Basement Desc.: Full, Fully Finished
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,907
  • Above Ground: 3,007 Sq. Ft.
  • Below Ground: 900 Sq. Ft.
  • Year Built: 1998

Lot Features

  • Lot Size (Acres): 2.29
  • Zoning: R-2
  • Lot Description: Fence - Full, Level Lot, Professionally Landscaped

Financial Considerations

  • Assessment Amount: $613,600
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Washer & dryer, microwave, deep freezer, grill, window treatments and curtain rods. Please see attached Exclusion list for details.
  • Property ID: 271729

Listed by Compass Connecticut, LLC, THE BRIANNA CARVALHO TEAM, Brianna Carvalho

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Listing agent

— 8 Windy Hill Rd —

  • Brianna Carvalho

    Compass Connecticut, LLC

Agent Contact: (516) 319-7609 Office Contact: (203) 290-2477

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 8 Windy Hill Rd

School Districts:Redding School District, Regional High School District 09
NameGradesDistance
John Read Middle School
486 Redding Road, Redding, CT 06896
5-81.5 mi
Redding Elementary School
33 Lonetown Road, Redding, CT 06896
PK-42.4 mi
Joel Barlow High School
100 Black Rock Turnpike, Redding, CT 06896
9-124.5 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 8 Windy Hill Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
5/01/2026
Listed
$1,195,000
16.59%
MLS
8/15/2022
Sold
$1,025,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 8 Windy Hill Rd

Year
Property Taxes
Change
Tax Assessment
Change
2025
$18,126
3%
$613,600
—
2023
$17,623
4%
$613,600
—
2023
$16,991
9%
$613,600
31%
2022
$15,633
2%
$468,900
—
2021
$15,399
—
$468,900
—
2020
$15,399
—
$468,900
—
2019
$15,399
4%
$468,900
—
2018
$14,874
13%
$468,900
6%
2017
$13,163
1%
$444,400
—
2016
$12,994
1%
$444,400
—
2015
$12,848
—
$444,400
—
2014
$12,848
—
$444,400
—
2011
$12,865
—
$444,400
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 8 Windy Hill Rd

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*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Listed by Compass Connecticut, LLC, THE BRIANNA CARVALHO TEAM, Brianna Carvalho

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8 Windy Hill Road, Redding, CT 06896 (MLS# 24171032) is a Single Family property with 4 bedrooms, 2 full bathrooms and 2 partial bathrooms. 8 Windy Hill Road is currently listed for $1,195,000 and was received on May 01, 2026. Want to learn more about 8 Windy Hill Road? Do you have questions about finding other Single Family real estate for sale in Redding? You can browse all Redding real estate or contact a Coldwell Banker agent to request more information.

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