37 Giles Hill Road

Redding, CT 06896

$1,995,000 PRICE
5 Beds
3/1 Baths
6,101 Sqft
4.57 Acres
1985 Built

Open House

Sat, May 10 : 1:00PM-3:00PM

Luxurious 5-bedroom Retreat In Redding

Impeccable attention to detail both inside and out this sprawling country estate, set back privately on 4.57 pastoral acres on scenic Giles Hill, one of Redding's most coveted addresses. This quintessential Connecticut farmhouse is like new in every way, but steeped in New England tradition with split rail perimeter fencing, over a dozen stone walls, wood shutters with "S" hooks, charming front porch, lush rolling lawn, plus mature flowering trees and gardens. The enchanting compound features extensive professional landscape and hardscape including terraced gardens with stone retaining walls and steps leading to the free form, saltwater pool. The outdoor oasis also includes a sport court for tennis or full court basketball; whimsical chicken coop/garden shed; custom cedar raised bed vegetable/cutting gardens set in pea gravel with stone surround; plus two tiered mahogany deck with awning for outdoor dining. Over 6,100 square feet of finished living space including 761 square foot studio/gym loft over the detached three car garage with French doors to the balcony. Total five bedrooms, three full and one half bathrooms, including luxurious primary suite and walk-up to spacious third floor bonus guest room. Extensive recent improvements: state of the art chef's kitchen with Viking and Sub-Zero appliances, double islands, and mother of pearl backsplash, open to the stunning great room with a wall of windows; forty year architectural roof; heating, ventilation, and air conditioning; Generac whole house generator; full exterior repainting includes split rail fencing around entire property (2024); and more. Exquisite in every way!

Listed by

Laura Ancona
Real Estate Salesperson
M
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Additional Information

ADDITIONAL INFORMATION

ATTIC DESCRIPTION: Heated, Finished, Floored, Walk-up
AVERAGE DAYS ON MARKET: 12
BASEMENT DESCRIPTION: Full, Storage, Fully Finished, Interior Access
DAYS ON MARKET: 12
ELEMENTARY SCHOOL: Redding
GARAGE: Detached Garage
GARAGE COUNT: 3
HAS POOL?: Yes
HIGH SCHOOL: Joel Barlow
IS OCCUPIED?: Owner
JUNIOR HIGH SCHOOL: John Read
LIVING AREA SQFT: 6,101
PROPERTY TAX: $26,655
SEWER: Septic
STYLE: Colonial, Farm House
TAX AMOUNT: $26,655
TAX YEAR: July 2024-June 2025
TYPE: Single Family For Sale
YEAR BUILT: 1985
YEAR BUILT DETAILS: Public Records
ZONING: R-2

AMENITIES

INTERIOR/EXTERIOR FEATURES

AIR CONDITIONING: Central Air, Zoned
APPLIANCES INCLUDED: Gas Range, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher, Washer, Dryer
ATTIC: Yes
BEDS: 5
COOLING: Central Air, Zoned
EXTERIOR FEATURES: Lighting,Shed,Awnings,Tennis Court,Porch,Deck,Garden Area,Stone Wall,Underground Sprinkler
EXTERIOR SIDING: Clapboard, Wood
FIREPLACES: 2
FULL BATHS: 3
FURNACE TYPE: Oil
HALF BATHS: 1
HEAT: Oil
HEAT FUEL: Oil
HOT WATER: Oil, Domestic
LAUNDRY ROOM: Main Level
POOL DESCRIPTION: In Ground Pool
ROOF: Asphalt Shingle
ROOMS: 13

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Location for 37 Giles Hill Road, Redding, CT

Schools for 37 Giles Hill Road, Redding, CT

Our community offers residents access to a number of fine private and public schools for all grade levels. Please read below for information on each of the schools in our area.

Elementary School
Redding Elementary School
33 Lonetown Road
Redding, CT 06896

Grades: PK-4
(203) 938-2519
Middle School
John Read Middle School
486 Redding Road
Redding, CT 06896

Grades: 5-8
(203) 938-2533
High School
Joel Barlow High School
100 Black Rock Turnpike
Redding, CT 06896

Grades: 9-12
(203) 938-2508

Private Schools

SCHOOL	LOCATION	GRADE
Montessori School Of Redding	Po Box 1188, Redding, CT, 06875	PK-K
Easton Country Day School	660 Morehouse Road, Easton, CT, 06612	PK-12
Child's World Academy	477 Main Street, Monroe, CT, 06468	PK-K
St Dominic's Academy	15 Pepper Street, Monroe, CT, 06468	4-12
St. Mary Elementary School	24 Dodgingtown Road, Bethel, CT, 06801	PK-8
Emmanuel Nursery School	285 Lyons Plain Road, Weston, CT, 06883	PK-K
Housatonic Valley Waldorf School	40 Dodgingtown Road, Newtown, CT, 06470	PK-8
Pinewood Learning Center	9 Picketts Ridge Road, Redding, CT, 06896	PK-K
Montessori School Of Redding	Po Box 1188, Redding, CT, 06875	PK-K
Easton Country Day School	660 Morehouse Road, Easton, CT, 06612	PK-12
Child's World Academy	477 Main Street, Monroe, CT, 06468	PK-K
St Dominic's Academy	15 Pepper Street, Monroe, CT, 06468	4-12
St. Mary Elementary School	24 Dodgingtown Road, Bethel, CT, 06801	PK-8
Emmanuel Nursery School	285 Lyons Plain Road, Weston, CT, 06883	PK-K
Housatonic Valley Waldorf School	40 Dodgingtown Road, Newtown, CT, 06470	PK-8
Pinewood Learning Center	9 Picketts Ridge Road, Redding, CT, 06896	PK-K

*UG = ungraded.
Detailed school information provided by GreatSchools.org © 2025. All rights reserved.

Public and private school information is provided by sources including GreatSchools.org and various MLS services including the One Key, SMARTMLS, NCMLS, DARMLS and Greenwich MLS, and is subject to the terms of use on those sites. William Pitt and Julia B. Fee Sotheby’s International Realty believes the information provided by these sources to be accurate but will not be held responsible if any data as well as information such as school districts for listings is inaccurate.

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Community

Redding

Fairfield County, Connecticut

Often referred to as the “Vermont of Connecticut,” Redding is a quiet, rural community that has earned the ranking as the No. 1 Small Town in Connecticut thanks to its low crime rate, superior school...

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Request More Info for 37 Giles Hill Road, Redding, CT

Laura Ancona
Real Estate Salesperson
M

View My Profile

Schedule a Showing Best Day/Time

Yes, I would like more information from Sotheby's International Realty. Please use and/or share my information with a Sotheby's International Realty agent to contact me about my real estate needs.