8 Windy Hill Rd, Redding, CT 06896
OFF MARKET

8 Windy Hill Rd
Redding, CT 06896

  • 4 Beds
  • 3 Baths
  • 3,787 sqft (on 2.29 acres)

$1,266,600

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $8,151/mo*

$1,266,600

Trulia Estimate
as of Jun 30, 2026
Est. Refi. Payment $8,151/mo*
4 Beds
3 Baths
3,787 sqft
(on 2.29 acres)

Local Information

  • Map ViewExplore the area around 8 Windy Hill Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Add this to your list of Must-See homes! Welcome home to this wonderful colonial in one of Redding's most sought-after neighborhoods close to shopping, restaurants, and Metro North. Enjoy entertaining in the open kitchen-family room area, outside on the deck, or poolside. The master bedroom suite offers a walk-in closet and fully updated bath with dual sinks, separate shower, and hydro-tub. Three more bedrooms, laundry, and full bath accompany the MBR on the upper level. The main level offers a formal living room and dining room with hardwood floors and fireplace; office with built-ins; newly updated kitchen with granite countertops and stainless appliances flowing into the family room which has a fireplace and a wall of doors that open up to the back deck; mudroom; and a half bath. The lower level has media room, rec room, half bath, and a section that offers plenty of storage. The expansive property is professionally landscaped, a level back yard, sloping front yard, a heated salt water gunite pool, garden, and a barn that can be finished for a pool house with changing rooms, bar, and kitchen. The NY Times, in a recent article, has dubbed Redding as "the Vermont of Connecticut". Come enjoy the quiet life while remaining close to civilization. Pool is now open!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
Garage
Outdoor
Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 8 Windy Hill Rd

Interior Features

Interior Details
BasementAtticNumber of Rooms: 9
Heating & Cooling
Heating: OilAir ConditioningHeating Fuel: Oil
Levels, Entrance, & Accessibility
Stories: 2
Appliances & Utilities
Cable ReadyDishwasherDryerRefrigeratorWasher
Fireplace & Spa
Fireplace

Exterior Features

Exterior Home Features
Roof: Asphalt, Shake ShingleDeckExterior: WoodPatio
Pool
Pool
Parking & Garage
GarageParking: Garage Attached

Property Information

Year Built
Year Built: 1998
Property Type / Style
Property Type: Single Family HomeArchitecture: Colonial

Community

Units in Building: 1

Lot Information

Lot Area: 2.29 acres

Price History for 8 Windy Hill Rd

DatePriceEventSource
08/16/2022$1,025,000Sold
N/A
11/01/2018$859,000ListingRemovedAgent Provided
04/03/2018$859,000Listed For SaleAgent Provided
11/06/2006$875,000Sold
N/A
07/17/1998$515,000Sold
N/A

Market trends in Redding

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
49
20
MoM
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Property Tax and Assessment

Year2025
Tax$18,126
Assessment$613,600
Home facts updated by county records

Comparable Sales for 8 Windy Hill Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.06
Single-Family Home
$1,199,000
07/16/25
4
3.5
3,045
0.27
Single-Family Home
$800,000
06/23/26
4
2.5
3,092
0.18
Single-Family Home
$725,000
07/24/25
5
3.5
3,786
0.24
Single-Family Home
$725,000
07/28/25
5
3.5
3,786
0.43
Single-Family Home
$950,000
04/15/26
3
2.5
2,455
0.51
Single-Family Home
$1,195,000
05/28/26
5
3.5
4,407
0.59
Single-Family Home
$725,000
11/05/25
4
2
3,024
0.43
Single-Family Home
$785,000
05/26/26
3
2
1,610
0.76
Single-Family Home
$1,600,000
11/18/25
5
3
3,407
0.75
Single-Family Home
$798,000
07/10/25
3
2.5
2,909

Nearby homes

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Assigned Schools

These are the assigned schools for 8 Windy Hill Rd.
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Redding

At least 41 Trulia users voted on each feature.
  • 96 % Say there's wildlife

  • 91 % Say parking is easy

  • 88 % Say car is needed

  • 87 % Say there's holiday spirit

  • 86 % Say it's dog friendly

  • 84 % Say it's quiet

  • 76 % Say yards are well-kept

  • 71 % Say they plan to stay for at least 5 years

  • 68 % Say neighbors are friendly

  • 63 % Say there are community events

  • 59 % Say people would walk alone at night

  • 42 % Say kids play outside

  • 33 % Say it's walkable to restaurants

  • 12 % Say it's walkable to grocery stores

  • 12 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Drewluca
    "Many families; safe; lots of space. Great place to live and raise kids. Friendly and close enough to everything to make it pleasant. "
  • Helga P.
    "We work from home. Therefore, we do not have a commute unless we have outside business meetings or other work related engagements. "
  • Betsy M.
    "We have potlucks and cookouts on our lane, and spontaneous get-togethers for cocktails. People always Everyone on our lane pitches in to help one another whenever needed. I wouldn’t say that’s the case for Redding as a whole, but definitely true on our lane!"
  • Agustahalla
    "A great place for small children. We work from home. This is a very peaceful place without being too remote. I love living here. ;-)"
  • Agustahalla
    "Quiet. Relatively safe for children. Great things to do outdoors near by. The town has organized great camps for kids through the summertime."
  • Jenbain23
    "My commute varies as I work at different locations. Fairfield County in general is horrible for rush hour traffic but when traveling North it could be less congested. "
  • Jenbain23
    "Love the neighborhood, but I don’t love the amount of people in town who have little awareness of appropriate fiscal responsibility with town finances."
  • Deidreyw
    "Nice small town, with plenty to do nearby. Great schools, many stores/shopping areas in surrounding towns and safe areas."
  • Deidreyw
    "It’s a nice small town with great schools, a lot of parks, and things to do in the area if you have little ones. Also, really nice restaurants in the area, so you don’t need to go far. There is a train station nearby and close to lots of shopping, highways and New York City!"
  • einarulfsson
    "Redding is the best Value in Fairfield County, amazing Schools, parks and recreation available."
  • Janeausten
    "Fabulous town full of wonderful parks and hiking trails. Town library started by Mark Twain and a hub of activity. Summer Concerts on the Green gather young and old to enjoy music and fun together. Excellent schools- always in top 10. "
  • Pdunay
    "Live and work here. Beautiful and peaceful country life. Great schools and very safe. "
  • rtklarsfeld
    "Part of prestigious Farview Farm Association with pool club and tennis courts. Completely updated in 2013. Custom gourmet kitchen of your dreams with double European dishwashers, Wolf 6 burner range, double ovens, warming drawer, Sub-Zero All Refrigerator and All Freezer . 3 car garage. Finished lower level 785 sq/ft for a total of 4,422 sq/ft."

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Homes for sale near 8 Windy Hill Rd

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Off Market Homes Near 8 Windy Hill Rd

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8 Windy Hill Rd, Redding, CT 06896 is a 4 bedroom, 4 bathroom, 3,787 sqft single-family home built in 1998. This property is not currently available for sale. 8 Windy Hill Rd was last sold on Aug 16, 2022 for $1,025,000. The current Trulia Estimate for 8 Windy Hill Rd is $1,266,600.