8 Windy Hill Road
Redding, CT 06877
- 4 Beds
- 3 Baths
- 3,907 sqft (on 2.29 acres)
4 Beds
3 Baths
3,907 sqft
(on 2.29 acres)
Local Information
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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
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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 |
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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 |
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Days on Market: 34 |
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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 |
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Price List Price: $1,195,000Price Per Sqft: $306 |
Status Change & Dates Off Market Date: Thu May 14 2026Possession Timing: Early July |
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MLS Status: Under Contract |
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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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Listing Agent Listing ID: 24171032 |
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Building Area Building Area: 3907 Square Feet |
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Community Features: Golf, Health Club, Lake, Library, Park, Playground, Shopping/Mall |
Other Playground |
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No HOA |
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Lot Area: 2.29 Acres |
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BasementMls Number: 24171032Zillow Contingency Status: Under ContractAttic: Storage, Pull Down StairsAttribution Contact: (516) 319-7609Above Grade Unfinished Area: 3007Activation Date: Fri May 01 2026 |
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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
| Date | Price | Event | Source |
|---|---|---|---|
| 05/14/2026 | $1,195,000 | Pending | Smart MLS #24171032 |
| 05/01/2026 | $1,195,000 | Listed For Sale | Smart MLS #24171032 |
| 08/15/2022 | $1,025,000 | Sold | Smart MLS #170485072 |
| 05/31/2022 | $975,000 | Contingent | Smart MLS #170485072 |
| 04/29/2022 | $975,000 | Listed For Sale | Smart MLS #170485072 |
| 11/03/2006 | $875,000 | Sold | Smart MLS #98293683 |
| 04/01/1999 | $503,600 | Sold | 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 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.Assigned Schools
These are the assigned schools for 8 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.
LGBTQ Local Legal Protections
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.

