37 Giles Hill Rd

Redding, CT 06896

$1,700,000
Last Sold Price
5
Beds
6,101 Sq. Ft.
$279 / Sq. Ft.
6,101
Sq. Ft.
$279
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Closed 9/3/25
Closed 9/3/25
a view of swimming pool

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...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.
  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
Garages Number
3
Neighborhood
N/A
Style
Colonial, Farm House
Garage Parking Info
Detached Garage
Swimming Pool
Yes
LISTING UPDATED: 09/03/2025 07:20 PM

Property Details for 37 Giles Hill Road

StatusClosed
MLS #24110300
Days on Market26
Taxes$27,416 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built1985
Lot Size4.57 AC / 199,069 SF
CountyFairfield County
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Location

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

Sold By Compass Connecticut, LLC, Jessica Sigmund

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Building Information for 37 Giles Hill Road

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

Payment Calculator

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$10,756 per month

30 year fixed, 6.36% Interest

Principal and Interest

$8,471

Property Taxes

$2,285

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

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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: -73.35546
  • Middle Jr High School: John Read
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $27,416
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
  • Listing Key: 397F7638C6B5F7CCE063E201100A7308
  • 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
  • Listing Key: 397F7638C6B5F7CCE063E201100A7308
  • 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
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
Aug 27, 2025

Closed (Public Record)

Public Record #1913522062

$1,700,000

+4.5% / yr

Sep 4, 1996

Closed (Public Record)

Public Record #91143557

$480,000—
DateEvent & SourcePrice
08/27/2025

Closed (Public Record)

Public Record #1913522062

$1,700,000

+4.5% / yr

09/04/1996

Closed (Public Record)

Public Record #91143557

$480,000

For completeness, we 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 Record2024$27,416 ($2,285 / month)
Home Facts
Lot Size199,069 SqFtStyleMulti-Family Dwelling (2-4)ZoningR-2CountyWESTERN CONNECTICUTAPNREDD M:31 L:94Fireplace TypeHas Fireplace

Schools near 37 Giles Hill Road

This home is within Redding School District.
Rating
School
Type
Grades
Distance
Redding Elementary School
Public - PK to 4
John Read Middle School
Public - 5 to 8
Joel Barlow High School
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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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, Inc., its subsidiaries, affiliates and their agents and associated third parties 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, Inc., its subsidiaries, affiliates and their agents and associated third parties make 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.