299 Redding Road
Redding, Connecticut 06896
Reduced from $899,000
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 3,876
- Acres
- 2.00
- Year Built
- 1979
- Neighborhood
- Georgetown
- 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
Back on the market with a fresh new lawn, this completely move-in ready home blends timeless architectural character with the seamless luxury today's lifestyle demands. The gourmet chef's kitchen boasts a stunning waterfall quartz island and high-end appliances. The open-concept main level features two living rooms with beautiful fireplaces and a spacious dining room, along with a first-floor bedroom-ideal for guests or a home office-and a mudroom with a laundry area. Upstairs, the expansive primary suite serves as a true private retreat, featuring a generous walk-in closet and a spa-like bathroom. Two additional bedrooms on this level provide ample space for family or guests. The finished, versatile attic showcases cathedral ceilings and currently serves as a family room and gym, offering endless possibilities for your lifestyle needs. The finished walk-out basement is an entertainer's dream, complete with a wet bar, built-in speakers, and a contemporary powder room. Outside, enjoy a spacious deck, while a two-car attached garage and semi-circular driveway accommodate multiple vehicles. Perfectly positioned in the desirable Georgetown neighborhood, this home offers peaceful wooded surroundings with convenient access to shopping, dining, and major routes.
Key Facts
- City/Town
- Redding
- Neighborhood
- Georgetown
- Property / Style
- Single Family · Colonial
- Year Built
- 1979
- Days on Market
- 148 days
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 3,876 sq ft
- Lot Size
- 2.00 acres
- Garage / Parking
- 2 garage · 6 total
- Property Taxes
- $12,203 / Annually
Market Snapshot
The Redding Market
Single Family · trailing 12 months
Active Listings
27
14 under contract
Median List Price
$995,000
27 active listings
Median Closed Price
$932,000
94 sales
Median Days on Market
59
27 active listings
Median $ / Sq Ft
$312
27 active listings
Sale-to-List Ratio
100.6%
94 sales
How this home compares
List Price
$859,000
vs $995,000 median
13.7% below median
Price / Sq Ft
$222
vs $312 median
28.8% below median
Days on Market
148 days
vs 59 days median
89 days longer than median
Based on 27 active and 94 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of November 3, 2026.
Location
299 Redding Road, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 29, 2026per month
- Principal & Interest$4,683
- Property Taxes$1,017
- Insurance$286
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Redding
- Neighborhood
- Georgetown
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1979
- New Construction
- No/Resale
- Living Area
- 3,876 sq ft
- Below Grade
- 1,260 sq ft
Schools
- Elementary
- Redding
- High
- Joel Barlow
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Ceiling FansSplit System
- Fireplaces
- 2
- Laundry
- Main Level
- Appliances
- Oven/RangeMicrowaveRange HoodRefrigeratorDishwasherWasherDryer
- Basement
- FullHeatedCooledPartially FinishedFull With Walk-Out
Exterior & Lot
- Lot Size
- 2.00 acres
- Zoning
- R-2
- Garage / Parking
- 2 garage spaces6 total parking spacesAttached GarageDrivewayPaved
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Shingle
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- Block
- Lot Description
- Some WetlandsLightly WoodedTreed
Listing & Financials
- Property Taxes
- $12,203 / Annually
- Days on Market
- 148
- MLS #
- 24181978
- MLS Status
- Active
Similar Properties
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 11/3/2026. 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 11/3/2026 at 9:30 PM UTC.