8 Windy Hill Rd
Redding, CT 06896
- 4 Beds
- 3 Baths
- 3,787 sqft (on 2.29 acres)
4 Beds
3 Baths
3,787 sqft
(on 2.29 acres)
Local Information
-- mins to
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
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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 |
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Exterior Home Features Roof: Asphalt, Shake ShingleDeckExterior: WoodPatio |
Pool Pool |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1998 |
Property Type / Style Property Type: Single Family HomeArchitecture: Colonial |
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Units in Building: 1 |
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Lot Area: 2.29 acres |
Price History for 8 Windy Hill Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 08/16/2022 | $1,025,000 | Sold | N/A |
| 11/01/2018 | $859,000 | ListingRemoved | Agent Provided |
| 04/03/2018 | $859,000 | Listed For Sale | Agent Provided |
| 11/06/2006 | $875,000 | Sold | N/A |
| 07/17/1998 | $515,000 | Sold | N/A |
Market trends in Redding
Last updated May 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
49
20MoM
Property Tax and Assessment
| Year | 2025 |
|---|---|
| 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
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 8 Windy Hill Rd.
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.
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Homes for sale near 8 Windy Hill Rd
Off Market Homes Near 8 Windy Hill Rd
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.

