$1,195,000
PENDING

8 Windy Hill Rd Redding, CT 06896

Estimated payment $7,990/month

Total Views 1,308
4 Beds
4 Baths
3,907 Sq Ft
$306 Price per Sq Ft

Highlights

  • Barn
  • Heated In Ground Pool
  • Deck
  • Redding Elementary School Rated A
  • Colonial Architecture
  • Attic

About This Home

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

Brianna Carvalho

Compass Connecticut, LLC Brokerage Phone: (516) 319-7609 License #RES.0817929 Listed on: 04/29/2026

Compass Connecticut, LLC

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $18,126

Year Built

  • Built in 1998

Lot Details

  • 2.29 Acre Lot
  • Garden
  • Property is zoned R-2

Home Design

  • Colonial Architecture
  • Concrete Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Wood Siding
  • Radon Mitigation System

Interior Spaces

  • Central Vacuum
  • Sound System
  • 2 Fireplaces
  • Home Gym
  • Finished Basement
  • Basement Fills Entire Space Under The House
  • Home Security System
  • Laundry on upper level

Kitchen

  • Built-In Oven
  • Cooktop
  • Dishwasher

Bedrooms and Bathrooms

  • 4 Bedrooms
  • Soaking Tub

Attic

  • Storage In Attic
  • Pull Down Stairs to Attic
  • Unfinished Attic

Parking

  • 2 Car Garage
  • Parking Deck
  • Automatic Garage Door Opener

Pool

  • Heated In Ground Pool
  • Gunite Pool
  • Saltwater Pool

Outdoor Features

  • Deck
  • Patio

Schools

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

Utilities

  • Central Air
  • Heating System Uses Oil
  • Private Company Owned Well
  • Oil Water Heater
  • Fuel Tank Located in Basement

Additional Features

  • Property is near golf course and shops
  • Barn

Listing and Financial Details

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

Home Details

Home Type

Single Family

Est. Annual Taxes

$18,126

Year Built

Built in 1998

Lot Details

2.29 Acres

Listing Details

  • Neighborhood: Umpawaug
  • Property Type: Single Family For Sale
  • Style: Colonial
  • Sq Ft Est Heated Above Grade: 3007
  • Sq Ft Est Heated Below Grade: 900
  • Total Sq Ft: 3907
  • Year Built: 1998
  • New Construction: No/Resale
  • Nearby Amenities: Golf Course, Health Club, Lake, Library, Park, Playground/Tot Lot, Shopping/Mall
  • Remarks Public Addendum: Offer Deadline - Monday 5/4 @ 3pm
  • Exclusions: Washer & dryer, microwave, deep freezer, grill, window treatments and curtain rods. Please see attached Exclusion list for details.
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Radon Mitigation Air Ynu: Yes
  • Radon Mitigation Water Ynu: Yes
  • Directions: Route 7 to Old Redding Road, Right on Windy Hill
  • Financing Used: Assumed Conventional
  • Street Type: Road
  • Office Attribution Contact: (203) 290-2477
  • Reserve Prospect: No
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 4
  • Total Bathrooms: 4
  • Full Bathrooms: 2
  • Half Bathrooms: 2
  • Fireplaces: 2
  • Attic Description: Unfinished, Storage Space, Pull-Down Stairs
  • Basement Description: Full, Fully Finished
  • Interior Amenities: Audio System, Auto Garage Door Opener, Central Vacuum, Security System
  • Appliances: Cook Top, Wall Oven, Refrigerator, Dishwasher
  • Additional Rooms: Gym
  • Laundry Room Info: Upper Level
  • Attic: Yes

Exterior Features

  • Exterior Features: Barn, Deck, Garden Area, Patio
  • Exterior Siding: Wood
  • Foundation Type: Concrete
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Not Applicable
  • Swimming Pool: Yes
  • Pool: Gunite, Heated, Salt Water, In Ground Pool
  • Construction Description: Frame

Garage/Parking

  • Garages Number: 2
  • Garage And Parking: Attached Garage

Utilities

  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Oil, Domestic
  • Water Source: Private Well
  • Sewer: Septic

Lot Info

  • Acres: 2.29
  • Lot Description: Fence - Full Level Lot Professionally Landscaped
  • Zoning: R-2
  • Parcel #: 271729

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 18126

MLS Schools

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

Map

Range of Values:

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Value Increase
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2025 $18,126 $613,600 $171,600 $442,000
2024 $17,623 $613,600 $171,600 $442,000
2023 $16,991 $613,600 $171,600 $442,000
2022 $15,633 $468,900 $161,400 $307,500
2021 $15,399 $468,900 $161,400 $307,500
2020 $15,399 $468,900 $161,400 $307,500
2019 $15,399 $468,900 $161,400 $307,500
2018 $14,874 $468,900 $161,400 $307,500
2017 $13,163 $444,400 $181,300 $263,100
2016 $12,994 $444,400 $181,300 $263,100
2015 $12,848 $444,400 $181,300 $263,100
2014 $12,848 $444,400 $181,300 $263,100
Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft Prior Sale
05/14/2026 05/14/26 Pending -- -- --
05/01/2026 05/01/26 For Sale $1,195,000 +16.6% $306 / Sq Ft
08/15/2022 08/15/22 Sold $1,025,000 +5.1% $341 / Sq Ft View Prior Sale
05/20/2022 05/20/22 Pending -- -- --
04/29/2022 04/29/22 For Sale $975,000 -- $324 / Sq Ft
Source: SmartMLS

Purchase History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Type Sale Price Title Company
Warranty Deed $1,025,000 None Available
Warranty Deed $875,000 --
Warranty Deed $515,000 --
Quit Claim Deed $90,000 --
Source: Public Records

Mortgage History

We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.

Date Status Loan Amount Loan Type
Open $700,000 Purchase Money Mortgage
Previous Owner $700,000 Purchase Money Mortgage
Previous Owner $412,000 Purchase Money Mortgage
Source: Public Records

Source: SmartMLS

MLS Number: 24171032

SmartMLS

APN: REDD-000028-000000-000049

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