$794,500
- 5 Beds
- 3 Baths
- 2,606 sqft (on 2 acres)
20 Winding Brook Lane, Redding, CT 06896
Est. Refi. Payment $5,457/mo*
Refinance Your HomeCurrently Off Market - Sold Sep 26, 2025 for $739,000
Home Value
Trulia Estimate
$795KSince last month
Increased$9K (+1.2%)Since last year
Increased$70K (+9.6%)Since last sale
Increased$54K (+7.4%)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 +75% in the last 10 years
| Month | Estimated value |
|---|---|
2026 | |
| September 2026 | $793K |
| August 2026 | $794K |
| July 2026 | $784K |
| June 2026 | $780K |
| May 2026 | $771K |
| April 2026 | $758K |
| March 2026 | $755K |
| February 2026 | $757K |
| January 2026 | $745K |
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 |
|---|---|---|---|---|---|---|---|
0.21 | Single-Family Home | $1,050,000 | 07/01/26 | 5 | 2.5 | 3,104 | |
0.47 | Single-Family Home | $630,000 | 01/21/26 | 5 | 3 | 1,508 | |
0.40 | Single-Family Home | $725,000 | 09/11/26 | 3 | 2.5 | 2,111 | |
0.39 | Single-Family Home | $975,000 | 05/21/26 | 4 | 3 | 3,982 | |
0.56 | Single-Family Home | $955,000 | 01/09/26 | 4 | 2.5 | 3,080 | |
0.60 | Single-Family Home | $915,000 | 11/05/25 | 4 | 2.5 | 2,177 | |
0.81 | Single-Family Home | $718,617 | 02/17/26 | 5 | 3 | 2,458 | |
1.07 | Single-Family Home | $599,000 | 10/10/25 | 5 | 3 | 2,639 | |
0.53 | Single-Family Home | $610,000 | 06/23/26 | 2 | 2 | 1,481 |
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 | $952,400 | 4 | 3 | 3,019 | Off Market | |
0.11 | $910,000 | 4 | 3.5 | 3,454 | For Sale | |
0.10 | $968,900 | 4 | 2.5 | 3,288 | Off Market | |
0.21 | $1,075,000 | 4 | 3.5 | 3,341 | For Sale | |
0.21 | $1,050,000 | 5 | 2.5 | 3,104 | Recently Sold | |
0.29 | $868,400 | 4 | 2.5 | 2,034 | Off Market | |
0.28 | $996,500 | 4 | 2.5 | 2,700 | Off Market | |
0.28 | $619,600 | 2 | 1.5 | 1,784 | Off Market | |
0.34 | $1,028,400 | 4 | 3 | 2,278 | Off Market | |
0.39 | $975,000 | 4 | 3 | 3,982 | Recently Sold | |
0.42 | $1,635,500 | 4 | 5 | 5,509 | Off Market |
Local Information
-- mins to
Home Highlights
Single-Family Home
Built in 1971
2 acre lot
2,606 sqft
$305/sqft
2 Car Garage
About this House
This expansive 5-bedroom, 3-bath ranch-style home offers over 2,600 sq. ft. of living space across 1.5 stories, set on a private 2-acre lot with level backyard. Classic cedarwood shingles, a slate foyer, and hardwood floors throughout the main level create a warm, timeless feel. The layout includes a family room with fireplace, a formal living room, and a versatile main-level den or office that could also serve as a formal dining room. The spacious eat-in kitchen opens to a screened-in porch, perfect for relaxing or entertaining. Additional features include 9 total rooms, a full unfinished basement with ample space for storage, oil hot water baseboard heat, central air, whole house generator and an attached 2-car garage. Enjoy a prime location near Saugatuck Falls and Putnam Park with easy access to scenic hiking trails and an ideal commute to New York and Southern Fairfield County.
20 Winding Brook Lane, Redding, CT 06896 is a 5 bedroom, 3 bathroom, 2,606 sqft single-family home built in 1971. It last sold for $739,000 on Sep 26, 2025 (6% above the $699,900 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $794,500, with a rent estimate of $5,708/month.
Last check for updates: about 6 hours ago
Listed by Matt Rose, (203) 470-9115
Keller Williams Realty, (203) 438-9494
Bought with: Susan C. Leone, (203) 209-2075, Higgins Group Bedford Square, (203) 226-0300
Source: Smart MLS, MLS#24118249

Home Details for 20 Winding Brook Lane
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Interior Details Basement: Full,Unfinished,Storage Space,Walk-Out AccessNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Den, Family Room, Kitchen, Living Room, Sun Room |
Beds & Baths Number of Bedrooms: 5Number of Bathrooms: 3Number of Bathrooms (full): 3 |
Dimensions and Layout Living Area: 2606 Square Feet |
Appliances & Utilities Appliances: Gas Range, Dishwasher, Water HeaterDishwasherLaundry: Main Level |
Heating & Cooling Heating: Hot Water,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Hot Water |
Fireplace & Spa Number of Fireplaces: 1Has a Fireplace |
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Exterior Home Features Roof: AsphaltFoundation: Concrete PerimeterNo Private Pool |
Parking & Garage Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached |
Frontage Not on Waterfront |
Water & Sewer Sewer: Septic Tank |
Finished Area Finished Area (above surface): 2606 Square Feet |
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Year Built Year Built: 1971 |
Property Type / Style Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Ranch |
Building Construction Materials: Shake SidingNot a New ConstructionDoes Not Include Home Warranty |
Property Information Parcel Number: 269608 |
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Price List Price: $699,900 |
Status Change & Dates Off Market Date: Wed Sep 10 2025Possession Timing: Negotiable |
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MLS Status: Closed |
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Direction & Address City: ReddingCommunity: Redding Center |
School Information Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Joel Barlow |
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Building Area Building Area: 2606 Square Feet |
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No HOA |
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Lot Area: 2 Acres |
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BasementMls Number: 24118249Above Grade Unfinished Area: 2606 |
Price and Tax history
| Date | Event | Price |
|---|---|---|
Sep 26, 2025 Source: Smart MLS #24118249 | Sold | $739,000 |
Sep 19, 2025 Source: Smart MLS #24118249 | Pending | $699,900 |
Aug 9, 2025 Source: Smart MLS #24118249 | Listed For Sale | $699,900 |
| Year | Property tax | Tax assessment |
|---|---|---|
| 2025 | $12,755 | $431,800 |
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

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Frequently asked questions about 20 Winding Brook Lane
- What is 20 Winding Brook Lane estimated to be worth?Trulia's estimated value for 20 Winding Brook Lane in Redding, CT is $794,500.
- What is the price history for 20 Winding Brook Lane?20 Winding Brook Lane in Redding, CT last sold for $739,000 in September 2025.
- 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 20 Winding Brook Lane have air conditioning?Yes, 20 Winding Brook Lane in Redding, CT has air conditioning.
- Does 20 Winding Brook Lane have laundry facilities?Yes, 20 Winding Brook Lane in Redding, CT has laundry facilities.