37 Giles Hill
Redding, CT 06896
Map
- 5 beds
- 4 baths
- 6,101 sqft
- ~5 acre lot
- $303 per sqft
- 1985 build
- – on site
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 checked:
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Last updated Jul 9, 2025
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MLS# 24110300 —
The Building
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Year Built:1985
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Year Built Source:Public Records
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New Construction Type:No/Resale
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Style:Colonial, Farm House
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Roof Information:Asphalt Shingle
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Attic:Yes
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Attic Description:Heated, Finished, Floored, Walk-up
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Exterior Siding:Clapboard, Wood
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Foundation Type:Concrete
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Basement Description:Full, Storage, Fully Finished, Interior Access
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Exterior Features:Lighting, Shed, Awnings, Tennis Court, Porch, Deck, Garden Area, Stone Wall, Underground Sprinkler
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Energy Features:Generator
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SqFt Total:6101
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SqFt Description:As measured
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SqFt Est Heated Above Grade:5389
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SqFt Est Heated Below Grade:712
Interior
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Interior Features:Security System
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Fireplaces Total:2
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Laundry Room:Main Level
Location
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Directions:Newtown Tpke or Black Rock Tpke to Giles Hill to #37 down accessway
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Neighborhood:N/A
The Property
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Parcel Number:269202
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Property Type:Single Family For Sale
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Zoning:R-2
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Acres:4.57
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Acres Source:Public Records
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Lot Description:Fence - Wood, Fence - Stone, Level Lot, Professionally Landscaped, Rolling
Listing Agent
- Contact info:
- Agent phone:
- (203) 438-9531
Taxes
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Tax Year:July 2025-June 2026
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Property Taxes:27416
Beds
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Beds Total:5
Baths
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Total Baths:4
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Full Baths:3
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Half Baths:1
The Listing
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https://www.seetheproperty.com/u/481319
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Virtual Tour Branded URL:https://www.seetheproperty.com/481319
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Home Warranty Offered:No
Heating & Cooling
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Heat Type:Hot Air
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Heat Fuel Type:Oil
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Cooling System:Central Air, Zoned
Utilities
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Water Source:Private Well
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Sewage System:Septic
Appliances
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Appliances Included:Gas Range, Microwave, Range Hood, Refrigerator, Subzero, Dishwasher, Washer, Dryer
Schools
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Elementary School:Redding
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Middle Or Junior School:John Read
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High School:Joel Barlow
The Community
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Swimming Pool:Yes
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Pool Description:In Ground Pool
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Direct Waterfront:No
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Waterfront Description:Not Applicable
Parking
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Garage & Parking:Detached Garage
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Garages Number:3
Monthly cost estimate
Asking price
$1,849,000
| Expense | Monthly cost |
|---|---|
|
Mortgage
This calculator is intended for planning and education purposes only. It relies on assumptions and information provided by you regarding your goals, expectations and financial situation, and should not be used as your sole source of information. The output of the tool is not a loan offer or solicitation, nor is it financial or legal advice. |
$9,900
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| Taxes | N/A |
| Insurance | $508 |
| Utilities | $559 See report |
| Total | $10,967/mo.* |
| *This is an estimate |
Walk Score®
Provided by WalkScore® Inc.
Walk Score is the most well-known measure of walkability for any address. It is based on the distance to a variety of nearby services and pedestrian friendliness. Walk Scores range from 0 (Car-Dependent) to 100 (Walker’s Paradise).
Bike Score®
Provided by WalkScore® Inc.
Bike Score evaluates a location's bikeability. It is calculated by measuring bike infrastructure, hills, destinations and road connectivity, and the number of bike commuters. Bike Scores range from 0 (Somewhat Bikeable) to 100 (Biker’s Paradise).
Air Pollution Index
Provided by ClearlyEnergy
The air pollution index is calculated by county or urban area using the past three years data. The index ranks the county or urban area on a scale of 0 (best) - 100 (worst) across the United Sates.
Sale history
| Date | Event | Source | Price | % Change |
|---|---|---|---|---|
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7/9/25
Jul 9, 2025
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Listed / Active | SMART_MLS | $1,849,000 | 42.8% (3.0% / YR) |
|
1/10/11
Jan 10, 2011
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SMART_MLS | $1,295,000 |
