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.
Offer Deadline - Monday 5/4 @ 3pm
Single-familyProperty Type
1998Year Built
2.29 acresLot Size
$358Price/Sq.Ft.
2 car garageParking
Listed by Brianna Carvalho• Compass Connecticut, LLC
Est. $1,525 per month, based on comparable rentals
Sale and tax history for 8 Windy Hill Rd
Sale History
Tax History
Date
Event
Price
Smart MLS #24171032
Jul 9, 2026
Sold
$1,400,000
$358/sq ft
May 14, 2026
Pending
—
May 4, 2026
Contingent
—
May 1, 2026
Listed
$1,195,000
$306/sq ft
Apr 29, 2026
Coming Soon
$1,195,000
$306/sq ft
Smart MLS #170485072
Aug 15, 2022
Sold
$1,025,000
$262/sq ft
May 12, 2022
Contingent
—
Apr 29, 2022
Listed
$975,000
$250/sq ft
Move right in and enjoy living in this warm and inviting 4 BR colonial located in a desirable SW Redding neighborhood. This exceptional property with 2+ level acres is highlighted by a superb gunite saltwater pool, expansive travertine patio and a professional landscape design featuring flowering plants, shrubs and, as an added bonus, a veggie garden! The charming barn serves as a wonderful sheltered seating location -- perfect for relaxing after a swim. It could be a "further finished" pool house with changing rooms and entertaining space -- the possibilities are endless! This casually elegant home enjoys an open-concept Kitchen/Family Room with HW floors, FP and a wall of doors with access to --and views of -- the fabulous backyard as well a a formal Living Room with fp and spacious formal Dining Room. The Library with custom built-ins is just perfect for relaxing with a good book -- or working from home! The upper level includes a Primary Bedroom suite with walk-in closet, fully-updated bath with dual sinks, separate shower and hydro-tub, and three additional spacious bedrooms, full bath and laundry room. A large lower level with half-bath offers a multitude of uses -- playroom, media room, gym or additional "at-home" office space. This extraordinary "quintessential Connecticut" property is simply perfect -- a private, neighborhood setting yet only minutes from shopping, restaurants, commuter routes and train to NYC!
Smart MLS #170065235
Nov 1, 2018
Listing Removed
—
Mar 25, 2018
Listed
$859,000
$220/sq ft
Smart MLS #99195037
Oct 31, 2017
Listing Removed
—
Jul 31, 2017
Listed
$875,000
$224/sq ft
Public Records
Nov 6, 2006
Sold
$875,000
$224/sq ft
Smart MLS #98293683
Jul 21, 2006
Listed
$949,000
$243/sq ft
Smart MLS #98034520
Feb 4, 1999
Listed
$513,000
$131/sq ft
Smart MLS #98002611
Jan 31, 1999
Listing Removed
—
Jan 28, 1998
Listed
$498,000
$127/sq ft
Smart MLS #96019738
Sep 30, 1997
Listing Removed
—
Jun 12, 1996
Listed
$485,000
$124/sq ft
Year
Property tax
Land + Additions
Assessment*
2023
$16,991 (+8.7%)
$171,600 + $442,000
$613,600
2022
$15,633 (+1.5%)
$161,400 + $307,500
$468,900
2021
$15,399
$161,400 + $307,500
$468,900
2020
$15,399
$161,400 + $307,500
$468,900
2019
$15,399 (+3.5%)
$161,400 + $307,500
$468,900
2018
$14,874 (+13.0%)
$161,400 + $307,500
$468,900
2017
$13,163 (+1.3%)
$181,300 + $263,100
$444,400
2016
$12,994 (+1.1%)
$181,300 + $263,100
$444,400
2014
$12,848
$181,300 + $263,100
$444,400
Public record
Beds
4
Baths
3
Stories
2
Lot width
—
Lot depth
—
Lot size
2.29 Acres
Year renovated
—
Sq. Ft.
3,007
Year built
1998
Style
Single Family Residential
County
Fairfield County
APN
271729
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 13, 2023.
Property details
Parking
Garage Information
Garage & Parking: Attached Garage
Garages Number: 2
Interior
Interior Information
Total Rooms: 9
Laundry Room Info: Upper Level
Interior Features: Audio System, Auto Garage Door Opener, Central Vacuum, Security System