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
Under contract
$1,195,000
8 Windy Hill Road, Redding, CT 06896
4beds
3,907sqft
Est.: Get pre-qualified
Single Family Residence
Built in 1998
2.29 Acres Lot
$-- Zestimate®
$306/sqft
$-- HOA
What's special
- 32 days |
- 591 |
- 32 |
Likely to sell faster than
Zillow last checked:
Listing updated:
Listed by:
THE BRIANNA CARVALHO TEAM,
Brianna Carvalho (516)319-7609,
Compass Connecticut, LLC 203-290-2477
Source: Smart MLS,MLS#: 24171032
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 2
- 1/2 bathrooms: 2
Rooms
- Room types: Gym
Primary bedroom
- Features: Double-Sink, Full Bath, Walk-In Closet(s), Wall/Wall Carpet
- Level: Upper
- Area: 336 Square Feet
- Dimensions: 24 x 14
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
- Area: 195 Square Feet
- Dimensions: 13 x 15
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
- Area: 176 Square Feet
- Dimensions: 16 x 11
Bedroom
- Features: Wall/Wall Carpet
- Level: Upper
- Area: 120 Square Feet
- Dimensions: 12 x 10
Dining room
- Features: Hardwood Floor
- Level: Main
- Area: 195 Square Feet
- Dimensions: 15 x 13
Family room
- Features: Balcony/Deck, Dining Area, Fireplace, Hardwood Floor, Sliders
- Level: Main
- Area: 336 Square Feet
- Dimensions: 24 x 14
Kitchen
- Features: Balcony/Deck, Breakfast Nook, Granite Counters, Dining Area, Kitchen Island, Sliders
- Level: Main
- Area: 300 Square Feet
- Dimensions: 15 x 20
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
- Area: 221 Square Feet
- Dimensions: 13 x 17
Media room
- Features: Half Bath, Wall/Wall Carpet
- Level: Lower
- Area: 299 Square Feet
- Dimensions: 13 x 23
Office
- Features: Bookcases, Built-in Features, Hardwood Floor
- Level: Main
- Area: 154 Square Feet
- Dimensions: 14 x 11
Rec play room
- Features: Wall/Wall Carpet
- Level: Lower
- Area: 416 Square Feet
- Dimensions: 13 x 32
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Cooktop, Oven, Refrigerator, Dishwasher, Water Heater
- Laundry: Upper Level
Features
- Sound System, Central Vacuum
- Basement: Full,Finished
- Attic: Storage,Pull Down Stairs
- Number of fireplaces: 2
Interior area
- Total structure area: 3,907
- Total interior livable area: 3,907 sqft
- Finished area above ground: 3,007
- Finished area below ground: 900
Property
Parking
- Total spaces: 2
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 2
Features
- Patio & porch: Deck, Patio
- Exterior features: Garden
- Has private pool: Yes
- Pool features: Gunite, Heated, Salt Water, In Ground
- Fencing: Full
Lot
- Size: 2.29 Acres
- Features: Level, Landscaped
Details
- Additional structures: Barn(s)
- Parcel number: 271729
- Zoning: R-2
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Wood Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1998
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & HOA
Community
- Features: Golf, Health Club, Lake, Library, Park, Playground, Shopping/Mall
- Security: Security System
- Subdivision: Umpawaug
HOA
- Has HOA: No
Location
- Region: Redding
Financial & listing details
- Price per square foot: $306/sqft
- Tax assessed value: $613,600
- Annual tax amount: $18,126
- Date on market: 4/29/2026
- Exclusions: Washer & dryer, microwave, deep freezer, grill, window treatments and curtain rods. Please see attached Exclusion list for details.
Estimated market value
Not available
Estimated sales range
Not available
Not available
Price history
| Date | Event | Price |
|---|---|---|
| 5/14/2026 | Pending sale | $1,195,000$306/sqft |
Source:  Smart MLS #24171032 Report a problem | ||
| 5/1/2026 | Listed for sale | $1,195,000+16.6%$306/sqft |
Source: Smart MLS #24171032 Report a problem | ||
| 8/15/2022 | Sold | $1,025,000+5.1%$262/sqft |
Source: Smart MLS #170485072 Report a problem | ||
| 5/31/2022 | Contingent | $975,000$250/sqft |
Source: Smart MLS #170485072 Report a problem | ||
| 4/29/2022 | Listed for sale | $975,000+11.4%$250/sqft |
Source: Smart MLS #170485072 Report a problem | ||
| 11/3/2006 | Sold | $875,000+73.7%$224/sqft |
Source: Smart MLS #98293683 Report a problem | ||
| 4/1/1999 | Sold | $503,600$129/sqft |
Source: Smart MLS #98034520 Report a problem | ||
Public tax history
Tax history is unavailable.
Monthly payment
Est. payment$--/mo
Payment breakdown
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HOA fees may include property taxes on listings classified as Co-Ops. Contact the listing agent and/or owner for fee details.
Mortgage interest rates are dependent on a number of factors, including credit score, down payment, and repayment length. Interest rate data provided by Zillow Group Marketplace, Inc. as of 1/1/1970 from various mortgage lenders with which we have lead or other similar arrangements; the Estimated Payment is an average of those rates.
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Climate risks
Neighborhood: 06877
Nearby schools
GreatSchools rating
- 9/10John Read Middle SchoolGrades: 5-8Distance: 1.5 mi
- 7/10Joel Barlow High SchoolGrades: 9-12Distance: 4.5 mi
- 8/10Redding Elementary SchoolGrades: PK-4Distance: 2.4 mi
Schools provided by the listing agent
- Elementary: Redding
- Middle: John Read
- High: Joel Barlow
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
A local agent can set up tours, give advice and negotiate with sellers.
- Connecticut
- Fairfield County
- Redding
- 06877
- 8 Windy Hill Road
Nearby cities
Nearby neighborhoods
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