299 Redding Road
Redding, Connecticut 06896
- 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
Experience modern luxury in this beautifully renovated Colonial. Newly seeded lawn! A grand double-door entry opens to a bright foyer. The all-new gourmet chef's kitchen boasts a massive waterfall quartz island, high-end appliances, and pot filler. The open-concept main level flows into a spacious living room with brick fireplace, while a secondary family room features a dramatic floor-to-ceiling stone fireplace and custom built-ins. Upstairs, the expansive primary suite serves as a true private retreat, featuring a generous walk-in closet and a stunning spa-like bathroom complete with a deep soaking tub and a double sink. Two additional bedrooms on this level provide ample space for family or guests. The newly finished, versatile attic showcases beautiful cathedral ceilings and currently serves as a family room and gym, offering endless possibilities for your lifestyle needs. The main level features a first-floor bedroom, ideal for guests or home office, plus a mud room with laundry area. The finished walk-out basement is an entertainer's dream with wet bar, movie theater with built-in speakers, and contemporary powder room. Outside, enjoy a private backyard with spacious deck. Two-car attached garage and semi-circular driveway accommodate multiple vehicles. Perfectly positioned in desirable Georgetown neighborhood, offering 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
- 50 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
- $11,326 / 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
$899,000
vs $1.26M median
28.7% below median
Price / Sq Ft
$232
vs $296 median
21.6% below median
Days on Market
50 days
vs 54 days median
4 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
299 Redding Road, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$4,584
- Property Taxes$944
- Insurance$300
- 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
- $11,326 / Annually
- Days on Market
- 50
- MLS #
- 24181978
- MLS Status
- Active
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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 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 7:05 AM UTC.