$1,311,000
- 5 Beds
- 4 Baths
- 4,631 sqft (on 2.96 acres)
5 Windy Hill Road, Redding, CT 06896
Est. Refi. Payment $8,934/mo*
Refinance Your HomeCurrently Off Market - Sold Aug 7, 2023 for $975,000
Home Value
Trulia Estimate
$1.31MSince last month
Decreased$3K (-0.2%)Since last year
Increased$60K (+4.8%)Since last sale
Increased$335K (+34.3%)Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.
Trulia Estimate
The of this home's value increased by +59% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $1.31M |
| August 2026 | $1.31M |
| July 2026 | $1.32M |
| June 2026 | $1.32M |
| May 2026 | $1.33M |
| April 2026 | $1.3M |
| March 2026 | $1.32M |
| February 2026 | $1.27M |
| January 2026 | $1.28M |
2025 | |
2024 | |
2023 | |
2022 | |
2021 | |
2020 | |
2019 | |
2018 | |
2017 | |
2016 | |
Comparable sales
These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.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 | |
0.51 | Single-Family Home | $985,000 | 08/03/26 | 4 | 2.5 | 2,328 | |
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 home prices
Get a sense of expected prices in the area by checking the value of nearby homes.Address | Distance | Price | Bed | Bath | Sqft | Status |
|---|---|---|---|---|---|---|
0.07 | $1,316,600 | 5 | 5 | 5,363 | Off Market | |
0.13 | $1,400,000 | 4 | 3 | 3,907 | Recently Sold | |
0.17 | $1,292,600 | 4 | 3.5 | 3,045 | Off Market | |
0.22 | $1,759,900 | 5 | 3.5 | 4,417 | Off Market | |
0.24 | $688,500 | 2 | 2 | 1,569 | Off Market | |
0.25 | $781,400 | 5 | 3.5 | 3,786 | Off Market | |
0.28 | $1,004,200 | 3 | 2.5 | 2,500 | Off Market | |
0.30 | $800,000 | 4 | 2.5 | 3,092 | Recently Sold | |
0.35 | $1,049,600 | 3 | 2.5 | 2,798 | Off Market | |
0.35 | $885,900 | 4 | 2.5 | 3,005 | Off Market | |
0.35 | $995,000 | 6 | 4 | - | Off Market |
Local Information
-- mins to
Home Highlights
Single-Family Home
Built in 1997
2.96 acre lot
4,631 sqft
$283/sqft
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. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,311,000, with a rent estimate of $8,062/month.
Last check for updates: about 20 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

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 |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Aug 7, 2023 Source: Smart MLS #170568749 | Sold | $975,000 |
Jun 16, 2023 Source: Berkshire Hathaway HomeServices New England Properties #170568749 | Pending | $975,000 |
May 26, 2023 Source: Berkshire Hathaway HomeServices New England Properties #170568749 | Contingent | $975,000 |
May 19, 2023 Source: Smart MLS #170568749 | Listed For Sale | $975,000 |
Jun 28, 2001 Source: Smart MLS #98092543 | Sold | $825,500 |
Jan 16, 1997 Source: N/A | Sold | $175,000 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $21,396 | $724,300 |
Home facts updated by county records
Market trends in Redding
Last updated August 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
35
1MoM
Around this home
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.
LGBTQ Local Legal Protections
LGBTQ Local Legal Protections

IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.
Frequently asked questions about 5 Windy Hill Road
- What is 5 Windy Hill Road estimated to be worth?Trulia's estimated value for 5 Windy Hill Road in Redding, CT is $1,311,000.
- What is the price history for 5 Windy Hill Road?5 Windy Hill Road in Redding, CT last sold for $975,000 in August 2023.
- Is Redding a buyer's or seller's market?Redding is currently a seller's market, based on recent for-sale activity.
- What do residents say about Redding?Residents describe Redding, CT as easy to park in, dog-friendly, and quiet. Most residents say you need a car. See recently sold homes in Redding, CT.
- Does 5 Windy Hill Road have air conditioning?Yes, 5 Windy Hill Road in Redding, CT has air conditioning.
- Does 5 Windy Hill Road have a pool?Yes, 5 Windy Hill Road in Redding, CT has a pool.