5 Windy Hill Road
Redding, CT 06896
- 5 Beds
- 4 Baths
- 4,631 sqft (on 2.96 acres)
5 Beds
4 Baths
4,631 sqft
(on 2.96 acres)
Local Information
-- mins to
Home Highlights
Property Type
Single-Family Home
Year Built
1997
Lot Size
2.96 acres
Living Area
4,631 sqft
Price/Sqft
$284
Parking
5 Car Garage
About this House
Come home to your own private oasis in the desirable town of Redding, coined “the Vermont of Connecticut.” Whether you love to entertain or want to spend your days lounging poolside with a book, your own private paradise has it all! Imagine your family and friends gathering around your newly surfaced gunite pool and spa with brand new lighting and the sound of a soothing waterfall in the background. Nestled within a highly sought after, quiet neighborhood, you will love to call this place home. This custom Colonial has been meticulously maintained and lovingly cared for by its owners. As you step into the main foyer, with limestone floors and arched doorways, you will be stunned by the soaring ceilings. The heart of this magnificent home is the oversized eat-in-kitchen with a large island that leads seamlessly into the great room with 18-ft ceilings and a brand new Palladian window at its center. Rounding out the first floor is an office or 5th bedroom w/a full bath. Upstairs, there are 4 generously sized bedrooms including the primary suite complete with a walk-in-closet and large ensuite bath. The remaining 3 bedrooms share a full bath. The finished lower level presents endless possibilities, from an entertainment center to a dedicated home gym, complete with a full bath and a kitchenette. Sliding doors lead to the pool area, seamlessly blending indoor and outdoor living. Car enthusiasts will be delighted by the 2 car attached + 3 car detached garage and circular driveway. Minutes from Route 7 and conveniently located near downtown Ridgefield, MetroNorth, and Topstone Park, this home offers a wonderful walking-friendly neighborhood as well as privacy and accessibility. Don't miss out on the opportunity to make this lovely property your new home just in time for summer!
5 Windy Hill Road, Redding, CT 06896 is a 5 bedroom, 4 bathroom, 4,631 sqft single-family home built in 1997. It last sold for the $975,000 asking price on Aug 7, 2023. It is currently off market. The Trulia Estimate is $1,314,800, with a rent estimate of $7,462/month.
Home Details for 5 Windy Hill Road
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Interior Details Basement: Full,Partially Finished,Heated,Cooled,Interior EntryNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Dining Room, Great Room, Kitchen, Living Room, Office, Rec Play Room |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 4Number of Bathrooms (full): 4 |
Dimensions and Layout Living Area: 4631 Square Feet |
Appliances & Utilities Appliances: Electric Cooktop, Microwave, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Upper LevelMicrowaveRefrigeratorWasher |
Heating & Cooling Heating: Zoned,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Zoned |
Fireplace & Spa Number of Fireplaces: 2Has a Fireplace |
Windows, Doors, Floors & Walls Window: Thermopane WindowsDoor: French Doors |
Security Security: Security System |
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Exterior Home Features Roof: AsphaltPatio / Porch: DeckExterior: Stone WallFoundation: Concrete PerimeterHas a Private Pool |
Parking & Garage Number of Garage Spaces: 5Number of Covered Spaces: 5No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 5Parking: Attached,Detached,Garage Door Opener,Private,Circular Driveway,Paved |
Pool Pool: In Ground, Pool/Spa Combo, Heated, GunitePool |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 3731 Square FeetFinished Area (below surface): 900 Square Feet |
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Year Built Year Built: 1997 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial |
Building Construction Materials: Wood SidingNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 1788097 |
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Price List Price: $975,000 |
Status Change & Dates Off Market Date: Fri Jun 16 2023Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: ReddingCommunity: Umpawaug |
School Information Elementary School: ReddingJr High / Middle School: John ReadHigh School: Joel Barlow |
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Building Area Building Area: 4631 Square Feet |
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Community Features: Golf, Lake, Library, Park |
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No HOA |
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Lot Area: 2.96 Acres |
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Energy Efficiency Features: Thermostat, Windows |
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BasementMls Number: 170568749Attic: Access Via HatchAbove Grade Unfinished Area: 3731 |
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GolfLakeLibraryPark |
Last check for updates: about 3 hours ago
Listed by Caroline Besancon, (203) 240-2602
Berkshire Hathaway NE Prop., (203) 438-9501
Brianna Carvalho, (516) 319-7609
Berkshire Hathaway NE Prop., (203) 438-9501
Bought with: Jim Dilillo, (203) 470-2678, Howard Hanna Rand Realty, (203) 790-7653
Source: Smart MLS, MLS#170568749

Price History for 5 Windy Hill Road
| Date | Price | Event | Source |
|---|---|---|---|
| 08/07/2023 | $975,000 | Sold | Smart MLS #170568749 |
| 06/16/2023 | $975,000 | Pending | Berkshire Hathaway HomeServices New England Properties #170568749 |
| 05/26/2023 | $975,000 | Contingent | Berkshire Hathaway HomeServices New England Properties #170568749 |
| 05/19/2023 | $975,000 | Listed For Sale | Smart MLS #170568749 |
| 06/28/2001 | $825,500 | Sold | Smart MLS #98092543 |
| 01/16/1997 | $175,000 | Sold | N/A |
Market trends in Redding
Last updated June 2026
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
38
11MoM
Property Tax and Assessment
| Year | 2025 |
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| Tax | $21,396 |
| Assessment | $724,300 |
Home facts updated by county records
Comparable Sales for 5 Windy Hill Road
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.13 | Single-Family Home | $1,400,000 | 07/09/26 | 4 | 3 | 3,907 | |
0.30 | Single-Family Home | $800,000 | 06/23/26 | 4 | 2.5 | 3,092 | |
0.63 | Single-Family Home | $1,195,000 | 05/28/26 | 5 | 3.5 | 4,407 | |
0.64 | Single-Family Home | $1,600,000 | 11/18/25 | 5 | 3 | 3,407 | |
0.56 | Single-Family Home | $950,000 | 04/15/26 | 3 | 2.5 | 2,455 | |
0.47 | Single-Family Home | $725,000 | 11/05/25 | 4 | 2 | 3,024 | |
0.63 | Single-Family Home | $1,585,000 | 05/27/26 | 4 | 3.5 | 4,548 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 5 Windy Hill Road.
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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