$1,700,000
SOLD SEP 3, 2025

37 Giles Hill Rd Redding, CT 06896

5 Beds
3.5 Baths
6,101 Sq Ft
4.57 Acres

Recently Sold

$279 Per Sq Ft

8% Below List Price

35 Days on Market

Highlights

  • Tennis Courts
  • In Ground Pool
  • 4.57 Acre Lot
  • Redding Elementary School Rated A
  • Sub-Zero Refrigerator
  • Colonial Architecture

About This Home

As of September 2025

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.

Last Agent to Sell the Property

Laura Ancona

William Pitt Sotheby's Int'l License #RES.0770587 Listed on: 07/09/2025

William Pitt Sotheby's Int'l

Last Buyer's Agent

Jessica Sigmund

Compass Connecticut, LLC License #RES.0809434

Compass Connecticut, LLC

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $27,416

Year Built

  • Built in 1985

Lot Details

  • 4.57 Acre Lot
  • Stone Wall
  • Sprinkler System
  • Garden
  • Property is zoned R-2

Home Design

  • Colonial Architecture
  • Farmhouse Style Home
  • Concrete Foundation
  • Frame Construction
  • Asphalt Shingled Roof
  • Wood Siding
  • Clap Board Siding

Interior Spaces

  • Vaulted Ceiling
  • 2 Fireplaces
  • Awning
  • Mud Room
  • Entrance Foyer
  • Home Gym
  • Home Security System

Kitchen

  • Gas Range
  • Range Hood
  • Microwave
  • Sub-Zero Refrigerator
  • Dishwasher
  • Viking Appliances

Bedrooms and Bathrooms

  • 5 Bedrooms

Laundry

  • Laundry Room
  • Laundry on main level
  • Dryer
  • Washer

Attic

  • Attic Floors
  • Walkup Attic
  • Finished Attic

Finished Basement

  • Basement Fills Entire Space Under The House
  • Interior Basement Entry
  • Basement Storage

Parking

  • 3 Car Garage
  • Parking Deck

Outdoor Features

  • In Ground Pool
  • Tennis Courts
  • Deck
  • Exterior Lighting
  • Shed
  • Porch

Schools

  • Redding Elementary School
  • John Read Middle School
  • Joel Barlow High School

Utilities

  • Zoned Heating and Cooling
  • Floor Furnace
  • Heating System Uses Oil
  • Power Generator
  • Private Company Owned Well
  • Oil Water Heater
  • Fuel Tank Located in Basement

Listing and Financial Details

  • Assessor Parcel Number 269202

Home Details

Home Type

Single Family

Est. Annual Taxes

$27,416

Year Built

Built in 1985

Lot Details

0

Listing Details

  • Neighborhood: N/A
  • Property Type: Single Family For Sale
  • Style: Colonial, Farm House
  • Sq Ft Est Heated Above Grade: 5389
  • Sq Ft Est Heated Below Grade: 712
  • Total Sq Ft: 6101
  • Year Built: 1985
  • New Construction: No/Resale
  • Direct Waterfront: No
  • Home Warranty Offered: No
  • Directions: Newtown Tpke or Black Rock Tpke to Giles Hill to #37 down accessway
  • Financing Used: Cash
  • Street Type: Road
  • Special Features: None
  • Property Sub Type: Detached

Interior Features

  • Total Bedrooms: 5
  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1
  • Fireplaces: 2
  • Attic Description: Heated, Finished, Floored, Walk-up
  • Basement Description: Full, Storage, Fully Finished, Interior Access
  • Interior Amenities: Security System
  • Appliances: Gas Range, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher, Washer, Dryer
  • Additional Rooms: Foyer, Gym, Laundry Room, Mud Room
  • Laundry Room Info: Main Level
  • Attic: Yes

Exterior Features

  • Exterior Features: Lighting, Shed, Awnings, Tennis Court, Porch, Deck, Garden Area, Stone Wall, Underground Sprinkler
  • Exterior Siding: Clapboard, Wood
  • Foundation Type: Concrete
  • Roof Information: Asphalt Shingle
  • Waterfront Description: Not Applicable
  • Swimming Pool: Yes
  • Pool: In Ground Pool
  • Construction Description: Frame

Garage/Parking

  • Garages Number: 3
  • Garage And Parking: Detached Garage

Utilities

  • Cooling System: Central Air, Zoned
  • Heat Type: Hot Air
  • Heat Fuel Type: Oil
  • Fuel Tank Location: In Basement
  • Hot Water Description: Oil, Domestic
  • Water Source: Private Well
  • Sewer: Septic

Green Features

  • Energy Features: Generator

Lot Info

  • Acres: 4.57
  • Lot Description: Fence - Wood Fence - Stone Level Lot Professionally Landscaped Rolling
  • Zoning: R-2
  • Parcel #: 269202

Tax Info

  • Tax Year: July 2025-June 2026
  • Property Tax: 27416

MLS Schools

  • Elementary School: Redding
  • Middle Jr High School: John Read
  • High School: Joel Barlow

Range of Values:

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Value Increase
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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Property History

Date Event Price List to Sale Price per Sq Ft
09/03/2025 09/03/25 Sold $1,700,000 -5.3% $279 / Sq Ft
08/13/2025 08/13/25 Pending -- -- --
07/22/2025 07/22/25 Price Changed $1,795,000 -2.9% $294 / Sq Ft
07/09/2025 07/09/25 For Sale $1,849,000 -- $303 / Sq Ft
Source: SmartMLS

Tax History Compared to Growth

Source: Public Records

Agents Affiliated with this Home

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Map

Source: SmartMLS

MLS Number: 24110300

SmartMLS

APN: REDD 00091100