More than a home, this soulful country estate is a living, breathing sanctuary-a place to reconnect with nature, beauty, and what matters most. This quintessential CT farmhouse is like new in every way, but steeped in New England tradition with split rail fencing, over a dozen stone walls, charming front porch, rolling lawn, plus mature flowering trees/gardens. Set back from the road on nearly 5 private acres along one of Redding's most scenic stretches, this exceptional estate offers a rare blend of timeless elegance, modern comfort, and bucolic privacy. Inside, over 6,000 sf of beautifully updated living space unfolds. The soaring great room and chef's kitchen-anchored by double islands, Viking and Sub-Zero appliances-form the true heart of the home. An inviting double fireplace opens to both the kitchen & living room. Five spacious bedrooms offer comfort & privacy, including a serene primary suite with vaulted ceilings & peaceful views. A finished 3rd floor adds flexibility for guests or creative pursuits. Above the detached 3 car garage, a private studio/gym offers endless possibilities for wellness, work, or quiet retreat. Step outside and you're immersed in nature: terraced gardens, a saltwater pool, sport court, and a two-tiered mahogany deck with sunset views over rolling ridgelines and neighboring horse farms. The landscape has been intentionally planted with native, pollinator-friendly species, welcoming butterflies, hummingbirds, and songbirds. Truly special.
Sold for $1,700,000
$1,700,000
37 Giles Hill Road, Redding, CT 06896
5beds
6,101sqft
Single Family Residence
Built in 1985
4.57 Acres Lot
$-- Zestimate®
$279/sqft
$7,439 Estimated rent
Home value
Not available
Estimated sales range
Not available
$7,439/mo
Zestimate® history
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List your homeWhat's special
Zillow last checked: 8 hours ago
Listing updated: September 03, 2025 at 12:20pm
Listed by:
Laura Ancona 203-733-7053,
William Pitt Sotheby's Int'l 203-438-9531
Bought with:
Jessica Sigmund, RES.0809434
Compass Connecticut, LLC
Source: Smart MLS,MLS#: 24110300
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 5
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Primary bedroom
- Features: Vaulted Ceiling(s), Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
- Area: 448.5 Square Feet
- Dimensions: 19.5 x 23
Bedroom
- Features: Beamed Ceilings, Ceiling Fan(s), Jack & Jill Bath, Wall/Wall Carpet
- Level: Upper
- Area: 266 Square Feet
- Dimensions: 14 x 19
Bedroom
- Features: Ceiling Fan(s), Jack & Jill Bath, Wall/Wall Carpet
- Level: Upper
- Area: 206.25 Square Feet
- Dimensions: 12.5 x 16.5
Bedroom
- Features: Full Bath, Wall/Wall Carpet
- Level: Upper
- Area: 162 Square Feet
- Dimensions: 12 x 13.5
Bedroom
- Features: Ceiling Fan(s), Full Bath, Wall/Wall Carpet
- Level: Other
- Area: 819 Square Feet
- Dimensions: 21 x 39
Dining room
- Features: Hardwood Floor
- Level: Main
- Area: 224 Square Feet
- Dimensions: 14 x 16
Family room
- Features: Built-in Features, French Doors, Patio/Terrace, Hardwood Floor
- Level: Main
- Area: 494.5 Square Feet
- Dimensions: 21.5 x 23
Great room
- Features: Vaulted Ceiling(s), Balcony/Deck, Dining Area, French Doors, Hardwood Floor
- Level: Main
- Area: 460 Square Feet
- Dimensions: 20 x 23
Kitchen
- Features: Granite Counters, Fireplace, Kitchen Island, Pantry, Hardwood Floor
- Level: Main
- Area: 225 Square Feet
- Dimensions: 15 x 15
Living room
- Features: Fireplace, French Doors, Hardwood Floor
- Level: Main
- Area: 229.5 Square Feet
- Dimensions: 13.5 x 17
Loft
- Features: Balcony/Deck, Hardwood Floor, Laminate Floor
- Level: Other
- Area: 833 Square Feet
- Dimensions: 24.5 x 34
Media room
- Features: Built-in Features, Hardwood Floor, Laminate Floor
- Level: Lower
- Area: 207 Square Feet
- Dimensions: 9 x 23
Rec play room
- Features: Hardwood Floor, Laminate Floor
- Level: Lower
- Area: 229.5 Square Feet
- Dimensions: 13.5 x 17
Heating
- Forced Air, Oil
Cooling
- Central Air, Zoned
Appliances
- Included: Gas Range, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher, Washer, Dryer, Water Heater
- Laundry: Main Level, Mud Room
Features
- Entrance Foyer
- Basement: Full,Storage Space,Finished,Interior Entry
- Attic: Heated,Finished,Floored,Walk-up
- Number of fireplaces: 2
Interior area
- Total structure area: 6,101
- Total interior livable area: 6,101 sqft
- Finished area above ground: 5,389
- Finished area below ground: 712
Property
Parking
- Total spaces: 3
- Parking features: Detached
- Garage spaces: 3
Features
- Patio & porch: Porch, Deck
- Exterior features: Lighting, Awning(s), Tennis Court(s), Garden, Stone Wall, Underground Sprinkler
- Has private pool: Yes
- Pool features: In Ground
- Fencing: Wood,Stone
Lot
- Size: 4.57 Acres
- Features: Level, Landscaped, Rolling Slope
Details
- Additional structures: Shed(s)
- Parcel number: 269202
- Zoning: R-2
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial,Farm House
- Property subtype: Single Family Residence
Materials
- Clapboard, Wood Siding
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 1985
Utilities & green energy
- Sewer: Septic Tank
- Water: Well
Community & neighborhood
Security
- Security features: Security System
Location
- Region: Redding
Price history
| Date | Event | Price |
|---|---|---|
| 9/3/2025 | Sold | $1,700,000-5.3%$279/sqft |
Source:  Smart MLS #24110300 Report a problem | ||
| 8/13/2025 | Pending sale | $1,795,000$294/sqft |
Source: Smart MLS #24110300 Report a problem | ||
| 7/22/2025 | Price change | $1,795,000-2.9%$294/sqft |
Source: Smart MLS #24110300 Report a problem | ||
| 7/9/2025 | Listed for sale | $1,849,000-7.3%$303/sqft |
Source: Smart MLS #24110300 Report a problem | ||
| 7/9/2025 | Listing removed | $1,995,000$327/sqft |
Source: Smart MLS #24088909 Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $27,416 +2.9% | $928,100 |
| 2024 | $26,655 +3.7% | $928,100 |
| 2023 | $25,699 +3.1% | $928,100 +24.1% |
Find assessor info on the county website
Neighborhood: 06896
Nearby schools
GreatSchools rating
- 8/10Redding Elementary SchoolGrades: PK-4Distance: 1.7 mi
- 8/10John Read Middle SchoolGrades: 5-8Distance: 2.4 mi
- 7/10Joel Barlow High SchoolGrades: 9-12Distance: 0.9 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.
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- Connecticut
- Fairfield County
- Redding
- 06896
- 37 Giles Hill Road