37 Giles Hill Rd

Redding, CT 06896

$1,995,000
Price
5
Beds
6,101 Sq. Ft.
$327 / Sq. Ft.
6,101
Sq. Ft.
$327
per Sq. Ft.

Description

Impeccable attention to detail both inside & 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 CT farmhouse is like new in every way, but steeped in New England tradition w/split rail perimeter fencing, over a dozen stone walls, wood shutters w/S hooks, charming front porch, lush rolling lawn, plus mature flowering trees & gardens. The enchanting compound features extensive professional landscape...Impeccable attention to detail both inside & 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 CT farmhouse is like new in every way, but steeped in New England tradition w/split rail perimeter fencing, over a dozen stone walls, wood shutters w/S hooks, charming front porch, lush rolling lawn, plus mature flowering trees & gardens. The enchanting compound features extensive professional landscape & hardscape including terraced gardens w/stone retaining walls & steps leading to the free form, saltwater pool. The outdoor oasis also includes a sport court for tennis/full court basketball; whimsical chicken coop/garden shed; custom cedar raised bed vegetable/cutting gardens set in pea gravel w/stone surround; plus two tiered mahogany deck w/awning for outdoor dining. Over 6,100 sf of finished living space including 761 sf studio/gym loft over the detached 3 car garage w/French doors to the balcony. Total 5 BR, 3 full & 1 half baths, including luxe primary suite & walk-up to spacious 3rd floor bonus guest room. Extensive recent improvements: state of the art chef's kitchen w/Viking & Sub-Zero appliances, double islands & mother of pearl backsplash, open to the stunning great room w/wall of windows; 40 year architectural roof; HVAC; Generac whole house generator; full exterior repainting incl. split rail fencing around entire property (2024); & more. Exquisite in every way!
  1. Listed by Laura Ancona • William Pitt Sotheby's Int'l
    P: (203)-438-9531 C: (203)-733-7053 lancona@wpsir.com

Property Details for 37 Giles Hill Road

Basement Description
Full, Storage, Fully Finished, Interior Access
Direct Waterfront
No
Expected Active Date
04-23-2025
Garages Number
3
Neighborhood
N/A
Style
Colonial, Farm House
Garage Parking Info
Detached Garage
Swimming Pool
Yes
LISTING UPDATED: 06/10/2025 10:03 PM

Property Details for 37 Giles Hill Road

StatusActive
MLS #24088909
Days on Market51
Taxes$26,655 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built1985
Lot Size4.57 AC / 199,069 SF
CountyFairfield County

Location

Listing Courtesy of William Pitt Sotheby's Int'l, Laura Ancona
Add your commute

Building Information for 37 Giles Hill Road

Stories-Year Built1985Building Size-Lot Size4.57 AC / 199,069 SF

Payment Calculator

$12,674 per month

30 year fixed, 6.845% Interest

Principal and Interest

$10,453

Property Taxes

$2,221

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 37 Giles Hill Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Newtown Tpke or Black Rock Tpke to Giles Hill to #37 down accessway
  • Elementary School: Redding
  • High School: Joel Barlow
  • Latitude: 41.299873
  • Longitude: -73.355458
  • Middle Jr High School: John Read
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2024-June 2025
  • Property Tax: $26,655
Virtual Tour
Interior and Exterior Features
Exterior Features
  • Exterior Features: Lighting, Shed, Awnings, Tennis Court, Porch, Deck, Garden Area, Stone Wall, Underground Sprinkler
  • Pool Description: In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Gas Range, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher, Washer, Dryer
  • Attic Description: Heated, Finished, Floored, Walk-up
  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 2
  • Interior Features: Security System
  • Laundry Room Info: Main Level
  • Rooms Additional: Foyer, Gym, Laundry Room, Mud Room
  • Rooms Total: 13
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,French Doors,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 13.5
Room 2
  • Room Entry Order: 10
  • Room Features: Ceiling Fan,Full Bath,Wall/Wall Carpet
  • Room Length: 39.0
  • Room Level: Other
  • Room Type: Bedroom
  • Room Width: 21.0
Room 3
  • Room Entry Order: 11
  • Room Features: Built-Ins,Hardwood Floor,Laminate Floor
  • Room Length: 23.0
  • Room Level: Lower
  • Room Type: Media Room
  • Room Width: 9.0
Room 4
  • Room Entry Order: 12
  • Room Features: Hardwood Floor,Laminate Floor
  • Room Length: 17.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 13.5
Room 5
  • Room Entry Order: 13
  • Room Features: Balcony/Deck,Hardwood Floor,Laminate Floor
  • Room Length: 34.0
  • Room Level: Other
  • Room Type: Loft
  • Room Width: 24.5
Room 6
  • Room Entry Order: 2
  • Room Features: Hardwood Floor
  • Room Length: 16.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 14.0
Room 7
  • Room Entry Order: 3
  • Room Features: Granite Counters,Fireplace,Island,Pantry,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 15.0
Room 8
  • Room Entry Order: 4
  • Room Features: Vaulted Ceiling,Balcony/Deck,Dining Area,French Doors,Hardwood Floor
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Great Room
  • Room Width: 20.0
Room 9
  • Room Entry Order: 5
  • Room Features: Built-Ins,French Doors,Patio/Terrace,Hardwood Floor
  • Room Length: 23.0
  • Room Level: Main
  • Room Type: Family Room
  • Room Width: 21.5
Room 10
  • Room Entry Order: 6
  • Room Features: Vaulted Ceiling,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 23.0
  • Room Level: Upper
  • Room Type: Primary BR Suite
  • Room Width: 19.5
Room 11
  • Room Entry Order: 7
  • Room Features: Beams,Ceiling Fan,Jack & Jill Bath,Wall/Wall Carpet
  • Room Length: 19.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 12
  • Room Entry Order: 8
  • Room Features: Ceiling Fan,Jack & Jill Bath,Wall/Wall Carpet
  • Room Length: 16.5
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.5
Room 13
  • Room Entry Order: 9
  • Room Features: Full Bath,Wall/Wall Carpet
  • Room Length: 13.5
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 12.0
Property
Property and Assessments
  • Construction Description: Frame
  • Exterior Siding: Clapboard, Wood
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 1985
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Sq Ft Description: As measured
  • Sq Ft Est Heated Below Grade: 712
  • Living Area SQFT Per Public Records: 0
Lot Information
  • Lot Description: Fence - Wood, Fence - Stone, Level Lot, Professionally Landscaped, Rolling
  • Parcel Number: 269202
  • Sq Ft Est Heated Above Grade: 5389.0
  • Sq Ft Total: 6101.0
  • Zoning: R-2
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Domestic
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 37 Giles Hill Road

DateEvent & SourcePriceAppreciation
Sep 4, 1996

Closed (Public Record)

Public Record #91143557

$480,000—
DateEvent & SourcePrice
09/04/1996

Closed (Public Record)

Public Record #91143557

$480,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 37 Giles Hill Road

Taxable ValueLand$217,100Additions$711,000Total$928,100
Tax Record2023$26,655 ($2,221 / month)
Home Facts
Beds0Lot Size199,069 SqFtStyleSingle Family ResidenceZoningR-2CountyFAIRFIELDAPNREDD M:31 L:94Fireplace TypeHas Fireplace

Schools near 37 Giles Hill Road

This home is within Redding School District.
Rating
School
Type
Grades
Distance
Public - PK to 4
Public - 5 to 8
Public - 9 to 12
Rating
School
Distance
Redding Elementary School
PublicPK to 4

John Read Middle School
Public5 to 8

Joel Barlow High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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37 Giles Hill Road is a single family home for sale in Redding, CT 06896. This property was listed for sale on April 17, 2025 by William Pitt Sotheby's Int'l, it's currently listed at $1,995,000. It has been on the market for a total of 51 days and was last sold on September 4, 1996. This listing's school districts are Redding School District, Regional School District 09. Nearby schools include Redding Elementary School, John Read Middle School and Joel Barlow High School. 37 Giles Hill Road is a 5-bed, 3.5-bath, 6,101 sqft single family home built in 1985.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of William Pitt Sotheby's Int'l, Laura Ancona

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.