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149 Old Redding Road

Redding, Connecticut 06896

ACTIVE - NEW$995,000
Beds
3
Baths
3 | 1
SqFt
2,110
Acres
1.01
Year Built
1958
Matt Caiola

Matt Caiola

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About This Home

You'll love this true nature lover's retreat, just 60 miles from NYC! Bordering 280 acre Topstone Park, this rare gem is a special place to call home. It underwent a total rebuild in 2003, resulting in a home that feels both timeless & entirely current. The professionally landscaped grounds burst with color 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. 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. Having a nature sanctuary bordering your prop. with a beach, trails & boating is the ideal place to call home.

Key Facts

City/Town
Redding
Neighborhood
N/A
Property / Style
Single Family · Split Level
Year Built
1958
Days on Market
0 days
Beds
3
Baths
3 full · 1 half
Living Area
2,110 sq ft
Lot Size
1.01 acres
Garage / Parking
2 garage
Property Taxes
$12,426 / Annually

Market Snapshot

The Redding Market

Single Family · trailing 12 months

Median Days on Market

63

24 active listings

Median $ / Sq Ft

$298

24 active listings

Sale-to-List Ratio

100.0%

98 sales

How this home compares

List Price

$995,000

vs $1.13M median

11.6% below median

Price / Sq Ft

$472

vs $298 median

58.4% above median

Days on Market

0 days

vs 63 days median

63 days fresher than median

Based on 24 active and 98 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of September 2, 2026.

Location

149 Old Redding Road, Redding, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$6,483

per month

  • Principal & Interest$5,115
  • Property Taxes$1,036
  • Insurance$332
  • 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
Year Built
1958
New Construction
No/Resale
Living Area
2,110 sq ft

Schools

Elementary
Redding
High
Joel Barlow

Interior

Heating
Hot Air
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
$12,426 / Annually
Days on Market
0
MLS #
24203939
MLS Status
Active

Similar Properties

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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 9/2/2026. 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 9/2/2026 at 7:10 PM UTC.