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$1,700,000
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Property Description
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.
Full Property Details
Full Property Details for 37 Giles Hill Rd
General
- Sold For: $1,700,000
- Taxes: (July 2025-June 2026)
- Status: Closed
- Type: Single Family
- Source: SMARTMLS
- MLS ID: 24110300
- Added to Site: 227 day(s) ago
Interior
- Number of Rooms: 13
- Rooms/Areas: Foyer, Gym, Laundry Room, Mud Room
- Interior Features: Security System
- Fireplace: Yes
- Number of Fireplaces: 2
- Appliances: Gas Range, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher, Washer, Dryer
Rooms
Bathrooms
- Total Bathrooms: 4
- Full Bathrooms: 3
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 5
- Primary Suite: Vaulted Ceiling, Full Bath, Walk-In Closet, Hardwood, 23 x 19.5, Upper
- Bedroom 1: Bedroom - Ceiling Fan, Full Bath, Wall/Wall Carpet, 39 x 21, Other
- Bedroom 2: Bedroom - Full Bath, Wall/Wall Carpet, 13.5 x 12, Upper
- Bedroom 3: Bedroom - Ceiling Fan, Jack & Jill Bath, Wall/Wall Carpet, 16.5 x 12.5, Upper
- Bedroom 4: Bedroom - Beams, Ceiling Fan, Jack & Jill Bath, Wall/Wall Carpet, 19 x 14, Upper
Other Rooms
- Living Room: Living Room - Fireplace, French Doors, Hardwood Floor, 17 x 13.5, Main
- Great Room: Great Room - Vaulted Ceiling, Balcony/Deck, Dining Area, French Doors, Hardwood Floor, 23 x 20, Main
- Family Room: Family Room - Built-Ins, French Doors, Patio/Terrace, Hardwood Floor, 23 x 21.5, Main
- Kitchen: Kitchen - Granite Counters, Fireplace, Island, Pantry, Hardwood Floor, 15 x 15, Main
- Dining Room: Dining Room - Hardwood Floor, 16 x 14, Main
- Loft: Loft - Balcony/Deck, Hardwood Floor, Laminate Floor, 34 x 24.5, Other
- Game room: Yes
- Game Room: Rec/Play Room - Hardwood Floor, Laminate Floor, 17 x 13.5, Lower
- Rec Room: Hardwood Floor, Laminate Floor, 17 x 13.5, Lower
- Theater/Media: Media Room - Built-Ins, Hardwood Floor, Laminate Floor, 23 x 9, Lower
- Laundry: Main Level
Additional Information
- Pool: Yes
- Pool Description: In Ground Pool
Exterior
- Exterior Features: Lighting, Shed, Awnings, Tennis Court, Porch, Deck, Garden Area, Stone Wall, Underground Sprinkler
Parking
- Garage: Yes
- Garage Spaces: 3
- Parking: Detached Garage
Location
- County: Fairfield
- Driving Directions: Newtown Tpke or Black Rock Tpke to Giles Hill to #37 down accessway
School Information
- Elementary School: Redding
- Middle School: John Read
- High School: Joel Barlow
Heating & Cooling
- Cooling Type: Central Air, Zoned
- Heating Type: Hot Air, Oil
- Heating Fuel: Oil
- Water Heater: Oil, Domestic
Utilities
- Sewer: Septic
- Water: Private Well
Structural Information
- Architectural Style: Colonial, Farm House
- Construction Status: No/Resale
- Exterior Const.: Clapboard, Wood
- Basement Desc.: Full, Storage, Fully Finished, Interior Access
- Roof: Asphalt Shingle
- Attic: Yes
- Square Feet: 6,101
- Above Ground: 5,389 Sq. Ft.
- Below Ground: 712 Sq. Ft.
- Year Built: 1985
Lot Features
- Lot Size (Acres): 4.57
- Zoning: R-2
- Lot Description: Fence - Wood, Fence - Stone, Level Lot, Professionally Landscaped, Rolling
Green Features
- Energy Features: Generator
Financial Considerations
- Assessment Amount: $928,100
- Tax Year: July 2025-June 2026
Disclosures and Reports
- Property ID: 269202
Listed by William Pitt Sotheby's Int'l, Laura Ancona
Sold by Compass Connecticut, LLC, THE SIGMUND TEAM AT COMPASS, Jessica Sigmund
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Schools
Schools serving 37 Giles Hill Rd
School Districts:Regional High School District 09, Redding School District
| Name | Grades | Distance |
|---|---|---|
Redding Elementary School 33 Lonetown Road, Redding, CT 06896 | PK-4 | 1.7 mi |
John Read Middle School 486 Redding Road, Redding, CT 06896 | 5-8 | 2.4 mi |
Joel Barlow High School 100 Black Rock Turnpike, Redding, CT 06896 | 9-12 | 0.9 mi |
Disclaimer:
School attendance boundaries provided by Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 37 Giles Hill Rd
Date
Details
Price
Change
Source
9/03/2025
Sold
$1,700,000
-5.29%
MLS
7/22/2025
Price Reduced
$1,795,000
-2.92%
MLS
7/09/2025
Listed
$1,849,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
37 Giles Hill Road, Redding, CT 06896 (MLS# 24110300) is a Single Family property that was sold at $1,700,000 on September 03, 2025. Want to learn more about 37 Giles Hill Road? Do you have questions about finding other Single Family real estate for sale in Redding? You can browse all Redding real estate or contact a Coldwell Banker agent to request more information.

