20 Winding Brook Lane, Redding, CT 06896
SOLD
SEP 26, 2025

20 Winding Brook Lane
Redding, CT 06896

  • 5 Beds
  • 3 Baths
  • 2,606 sqft (on 2 acres)

$739,000

Last Sold: Sep 26, 2025
6% over list $700K
$284/sqft
Est. Refi. Payment $4,814/mo*

$739,000

Last Sold: Sep 26, 2025
6% over list $700K
$284/sqft
Est. Refi. Payment $4,814/mo*
5 Beds
3 Baths
2,606 sqft
(on 2 acres)

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

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.
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. This description is from September 27, 2025

Home Highlights

Parking
2 Car Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
$284/sqft
Listed
180+ days ago

Home Details for 20 Winding Brook Lane

Interior Features

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

Exterior Features

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

Property Information

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

Price & Status

Price
List Price: $699,900Price Per Sqft: $284/sqft
Status Change & Dates
Off Market Date: Wed Sep 10 2025Possession Timing: Negotiable

Active Status

MLS Status: Closed

Location

Direction & Address
City: ReddingCommunity: Redding Center
School Information
Elementary School: Per Board of EdJr High / Middle School: Per Board of EdHigh School: Joel Barlow

Building

Building Area
Building Area: 2606 Square Feet

HOA

No HOA

Lot Information

Lot Area: 2 Acres

Miscellaneous

BasementMls Number: 24118249Above Grade Unfinished Area: 2606
Last check for updates: about 7 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

Price History for 20 Winding Brook Lane

DatePriceEventSource
09/26/2025$739,000Sold
Smart MLS #24118249
09/19/2025$699,900PendingSmart MLS #24118249
08/09/2025$699,900Listed For SaleSmart MLS #24118249

Market trends in Redding

Last updated April 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
29
13
MoM
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Property Tax and Assessment

Year2025
Tax$12,755
Assessment$431,800
Home facts updated by county records

Homeowner tools

Estimated monthly rent$5,330/mo

Comparable Sales for 20 Winding Brook Lane

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.07
Single-Family Home
$884,000
08/08/25
4
3
3,019
0.34
Single-Family Home
$955,000
08/22/25
4
3
2,278
0.47
Single-Family Home
$630,000
01/21/26
5
3
1,508
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
0.48
Single-Family Home
$1,600,000
07/24/25
5
5
5,945

Nearby homes

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Assigned Schools

These are the assigned schools for 20 Winding Brook Lane.
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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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.
20 Winding Brook Lane, Redding, CT 06896 is a 5 bedroom, 3 bathroom, 2,606 sqft single-family home built in 1971. This property is not currently available for sale. 20 Winding Brook Lane was last sold on Sep 26, 2025 for $739,000 (6% higher than the asking price of $699,900). The current Trulia Estimate for 20 Winding Brook Lane is $769,200.