37 Giles Hill Road, Redding, CT 06896 (MLS # 24110300)

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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.

DAYS ON MARKET 1 LAST UPDATED 7/9/2025
YEAR BUILT 1985 GARAGE SPACES 3.0
COUNTY Fairfield STATUS Active
PROPERTY TYPE(S) Single Family

SCHOOLS
Elementary School Redding
Jr. High School John Read
High School Joel Barlow


ADDITIONAL DETAILS
AIR Central Air, Zoned
AIR CONDITIONING Yes
APPLIANCES Dishwasher, Dryer, Gas Range, Microwave, Range Hood, Refrigerator, Washer
BASEMENT Finished, Full, Storage Space, Yes
CONSTRUCTION Clapboard, Frame, Wood Siding
EXTERIOR Garden, Tennis Court(s)
FIREPLACE Yes
GARAGE Yes
HEAT Forced Air, Oil
INTERIOR Entrance Foyer
LOT 4.57 acre(s)
LOT DESCRIPTION Level, Rolling Slope
POOL DESCRIPTION Outdoor Pool, In Ground
SEWER Septic Tank
STYLE Colonial, Farm House
TAXES 27416
WATER Well
ZONING R-2
MORTGAGE CALCULATOR
   

TOTAL MONTHLY PAYMENT

0
P
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*Estimate only



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Listing courtesy of William Pitt Sotheby's Int'l
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