40 Deer Hill Road
Redding, Connecticut 06896
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,690
- Acres
- 2.12
- Year Built
- 1988
- Neighborhood
- Redding Center
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Tucked away on a quiet, tree-lined street in the center of town, 40 Deer Hill Road offers the rare balance of privacy, comfort, and everyday convenience. The moment you step inside, you are greeted by cascading natural light from a dramatic wall of windows. At the heart of the home is the main living area, an inviting space anchored by a fireplace, soaring cathedral ceilings, and windows that frame the changing seasons and bring the outdoors in. Just beyond, the deck serves as a private retreat, perfect for morning coffee or summer dinners overlooking the serene property. The updated eat-in kitchen is designed for both everyday living and entertaining, featuring a center island, double ovens, and generous space to gather. With comfort and flexibility in mind, the home also features a first-floor primary suite with a fireplace, private deck, dual walk in closets and a spacious primary bath w/oversized shower and soaking tub, creating a true retreat. The main level is rounded out with a second bedroom, 2 additional baths, dining room, & an office. Upstairs are 2 large bedrooms sharing a full bath. A bonus room above the garage offers versatility, ideal as a second office, playroom, media room, or guest space. With extensive improvements, peaceful surroundings, and a location that offers convenient access to town, schools, commuter routes & dining, this is a home that effortlessly combines everyday ease with the space to relax, gather, & truly enjoy.OFFER DEADLINE TUES 4/28 12PM
Key Facts
- City/Town
- Redding
- Neighborhood
- Redding Center
- Property / Style
- Single Family · Contemporary
- Year Built
- 1988
- Days on Market
- 97 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 3,690 sq ft
- Lot Size
- 2.12 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $17,629 / Annually
Market Snapshot
The Redding Market
Single Family · trailing 12 months
Active Listings
24
24 under contract
Median List Price
$1.26M
24 active listings
Median Closed Price
$947,500
96 sales
Median Days on Market
54
24 active listings
Median $ / Sq Ft
$296
24 active listings
Sale-to-List Ratio
100.0%
96 sales
How this home compares
List Price
$1.13M
vs $1.26M median
10.7% below median
Price / Sq Ft
$305
vs $296 median
In line with median
Days on Market
97 days
vs 54 days median
43 days longer than median
Based on 24 active and 96 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of July 28, 2026.
Location
40 Deer Hill Road, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,736
- Property Taxes$1,469
- Insurance$375
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Redding
- Neighborhood
- Redding Center
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Contemporary
- Year Built
- 1988
- New Construction
- No/Resale
- Living Area
- 3,690 sq ft
Schools
- Elementary
- Redding
- High
- Joel Barlow
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- RefrigeratorDishwasherWasherDryer
- Basement
- Crawl SpaceFullUnfinishedInterior AccessFull With Walk-Out
- Interior Features
- Auto Garage Door OpenerOpen Floor Plan
Exterior & Lot
- Lot Size
- 2.12 acres
- Zoning
- R-2
- Garage / Parking
- 2 garage spacesAttached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Deck
- Lot Description
- Lightly WoodedSloping Lot
Listing & Financials
- Property Taxes
- $17,629 / Annually
- Days on Market
- 97
- MLS #
- 24169044
- MLS Status
- Under Contract
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 7/28/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 7/28/2026 at 7:10 AM UTC.