149 Old Redding Road
Redding, Connecticut 06896
- Beds
- 3
- Baths
- 3 | 1
- SqFt
- 2,754
- Acres
- 1.01
- Year Built
- 1958
- 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
Imagine a home where the air is fresh & the pace of life slows. This is a true nature lover's retreat, just 60 miles from NYC. This gem underwent a total rebuild in 2003, resulting in a home that feels both timeless & entirely current. The professionally landscaped grounds burst with color and texture, creating a seamless connection between the indoors & the gorgeous natural landscape.At the heart of the home a chef's kitchen serves as the ultimate gathering spot, flowing into the dining/liv. areas. Here, soaring cathedral ceilings & large windows invite the light in.The charm of this home lies in its "not a cookie-cutter" personality. You'll find delightful nods to its heritage, like original oversized planked floors & exposed brick, paired with the rustic warmth of hand-hewed beams and hardwood floors that run throughout most of the home. With 3-4 beds and 2 fpls, the layout is as functional as it is beautiful. The primary suite on main level with walk-in closet & full bath is ideal. The lower level is a revelation, with high ceilings, a massive fireplace, bath & private entrance offering incredible potential for in-laws. As a model of modern efficiency, a new roof was installed with a cutting-edge solar power system in 2023 with a prepaid 25-year assumable lease:this system currently generates more energy than the home consumes, providing a massive financial benefit. 280 acre Topstone Park borders this beauty with a beach, trails & boating. The ideal place to call home!
Key Facts
- City/Town
- Redding
- Neighborhood
- N/A
- Property / Style
- Single Family · Split Level,Other
- Year Built
- 1958
- Days on Market
- 42 days
- Beds
- 3
- Baths
- 3 full · 1 half
- Living Area
- 2,754 sq ft
- Lot Size
- 1.01 acres
- Garage / Parking
- 2 garage
- Property Taxes
- $12,425 / 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
$1.07M
vs $1.26M median
14.7% below median
Price / Sq Ft
$390
vs $296 median
31.8% above median
Days on Market
42 days
vs 54 days median
12 days fresher 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
149 Old Redding Road, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,481
- Property Taxes$1,035
- Insurance$358
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Redding
- Neighborhood
- N/A
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Split Level,Other
- Year Built
- 1958
- New Construction
- No/Resale
- Living Area
- 2,754 sq ft
Schools
- Elementary
- Redding
- High
- Joel Barlow
Interior
- Heating
- Hot AirSolarWood/Coal Stove
- Heat Fuel
- OilSolarWood
- Cooling
- Central AirZoned
- Fireplaces
- 2
- Laundry Location
- Full Room lower level
- Appliances
- Gas CooktopMicrowaveRange HoodRefrigeratorDishwasherWasherElectric Dryer
- Basement
- FullHeatedFully FinishedGarage AccessCooledWalk-outFull With Walk-Out
- In-Law Apartment
- PossibleLower Level
- Interior Features
- Cable - Pre-wiredOpen Floor PlanSecurity System
- Accessibility
- Bath Grab Bars
Exterior & Lot
- Lot Size
- 1.01 acres
- Zoning
- R-2
- Garage / Parking
- 2 garage spacesUnder House Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Shake
- Color
- Brown
- Roof
- Asphalt Shingle
- Foundation
- Block
- Exterior Features
- ShedDeckGuttersGarden AreaLightingStone WallPatio
- Lot Description
- Non Conforming LotTreedBorders Open SpaceSloping LotProfessionally Landscaped
Listing & Financials
- Property Taxes
- $12,425 / Annually
- Days on Market
- 42
- MLS #
- 24182650
- MLS Status
- Active
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 8:10 AM UTC.