8 Windy Hill Road, Redding, CT 06877
UNDER CONTRACT
2.29 ACRES

8 Windy Hill Road
Redding, CT 06877

  • 4 Beds
  • 3 Baths
  • 3,907 sqft (on 2.29 acres)

$1,195,000

Est. Mortgage $7,713/mo*

$1,195,000

Est. Mortgage $7,713/mo*
4 Beds
3 Baths
3,907 sqft
(on 2.29 acres)

Local Information

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

Description

Set on over 2 private acres in a coveted neighborhood in SW Redding, this sun-filled 4 BR Colonial blends timeless style, scale and effortless living. Designed for both entertaining and daily life, the main level centers around a spacious EIK w/center island, all-new appliances and seamless flow to the adjoining family room w/gas fireplace. Sliders open to the deck and grounds beyond, creating an easy indoor-outdoor flow. A formal dining room is ideal for gatherings, while a second living room w/fireplace provides an inviting retreat. A dedicated home office with a wall of custom built-ins & a powder room complete the main floor. Upstairs, the expansive primary suite is a sanctuary, featuring dual walk-in closets and a large bath w/soaking tub. 3 additional bedrooms share an updated hall bath, while 2nd floor laundry adds convenience. The finished lower level adds versatility with a spacious recreation/media room, dedicated gym & half bath. Outside, the property truly shines. A level, usable yard is anchored by a heated gunite saltwater pool w/travertine surrounds, creating a private resort-like setting for summer entertaining and quiet afternoons. The charming barn has outstanding potential to become a pool house or studio. Minutes from Route 7, downtown Ridgefield, MetroNorth, and Topstone Park, this home delivers the rare combination of neighborhood living, privacy and convenience, just in time for summer. Offer Deadline - Monday 5/4 @ 3pm

Home Highlights

Parking
2 Car Garage
Outdoor
Patio, Deck, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$306
Listed
34 days ago

Home Details for 8 Windy Hill Road

Interior Features

Interior Details
Basement: Full,FinishedNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Kitchen, Living Room, Media Room, Office, Rec Play Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 4Number of Bathrooms (full): 2Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 3907 Square Feet
Appliances & Utilities
Appliances: Cooktop, Oven, Refrigerator, Dishwasher, Water HeaterDishwasherLaundry: Upper LevelRefrigerator
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 2Has a Fireplace
Security
Security: Security System

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Deck, PatioFencing: FullOther Structures: Barn(s)Exterior: GardenFoundation: Concrete PerimeterGardenHas a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas an Attached GarageParking Spaces: 2Parking: Attached,Garage Door Opener
Pool
Pool: Gunite, Heated, Salt Water, In GroundPool
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3007 Square FeetFinished Area (below surface): 900 Square Feet

Days on Market

Days on Market: 34

Property Information

Year Built
Year Built: 1998
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
Not Included in Sale: Washer & dryer, microwave, deep freezer, grill, window treatments and curtain rods. Please see attached Exclusion list for details.Parcel Number: 271729

Price & Status

Price
List Price: $1,195,000Price Per Sqft: $306
Status Change & Dates
Off Market Date: Thu May 14 2026Possession Timing: Early July

Active Status

MLS Status: Under Contract

Location

Direction & Address
City: ReddingCommunity: Umpawaug
School Information
Elementary School: ReddingJr High / Middle School: John ReadHigh School: Joel Barlow

Agent Information

Listing Agent
Listing ID: 24171032

Building

Building Area
Building Area: 3907 Square Feet

Community

Community Features: Golf, Health Club, Lake, Library, Park, Playground, Shopping/Mall
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 2.29 Acres

Miscellaneous

BasementMls Number: 24171032Zillow Contingency Status: Under ContractAttic: Storage, Pull Down StairsAttribution Contact: (516) 319-7609Above Grade Unfinished Area: 3007Activation Date: Fri May 01 2026

Additional Information

GolfHealth ClubLakeLibraryParkPlaygroundShopping/Mall
Last check for updates: about 14 hours ago
Listing courtesy of Brianna Carvalho, (516) 319-7609
Compass Connecticut, LLC, (516) 319-7609
Source: Smart MLS, MLS#24171032
Also Listed on Smart MLS.

Price History for 8 Windy Hill Road

DatePriceEventSource
05/14/2026$1,195,000PendingSmart MLS #24171032
05/01/2026$1,195,000Listed For SaleSmart MLS #24171032
08/15/2022$1,025,000Sold
Smart MLS #170485072
05/31/2022$975,000ContingentSmart MLS #170485072
04/29/2022$975,000Listed For SaleSmart MLS #170485072
11/03/2006$875,000Sold
Smart MLS #98293683
04/01/1999$503,600Sold
Smart MLS #98034520

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Comparable Sales for 8 Windy Hill Road

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
0.18
Single-Family Home
$725,000
07/24/25
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
0.76
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
0.97
Single-Family Home
$1,150,000
06/30/25
4
3
3,020
0.55
Single-Family Home
$675,000
07/21/25
3
2
1,364

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Assigned Schools

These are the assigned schools for 8 Windy Hill Road.
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."

LGBTQ Local Legal Protections

Brianna Carvalho, Compass Connecticut, LLC, (516) 319-7609
Agent Phone: (516) 319-7609
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.
8 Windy Hill Road, Redding, CT 06877 is a 4 bedroom, 4 bathroom, 3,907 sqft single-family home built in 1998. This property is currently available for sale and was listed by Smart MLS on Apr 29, 2026. The MLS # for this home is MLS# 24171032.