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149 Old Redding Road

Redding, Connecticut 06896

ACTIVE$1,075,000
Beds
3
Baths
3 | 1
SqFt
2,754
Acres
1.01
Year Built
1958
Matt Caiola

Matt Caiola

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,874

per 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.

Listed By

Peggy Jorgensen

(203) 733-4876

Compass Connecticut, LLC

(203) 293-9715

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.