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299 Redding Road

Redding, Connecticut 06896

ACTIVE$879,000

Reduced from $899,000

Beds
4
Baths
3 | 1
SqFt
3,876
Acres
2.00
Year Built
1979
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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2-Car Garage2 FireplacesPrice Reduced

About This Home

Back on the market with a fresh new look! The sellers have professionally seeded the yard, offering the ultimate fresh start with a brand new lawn coming in nicely. Experience modern luxury in this beautifully renovated Colonial. The gourmet chef's kitchen boasts a massive waterfall quartz island and high-end appliances. 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 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. 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, 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
95 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

Median Days on Market

46

26 active listings

Median $ / Sq Ft

$281

26 active listings

Sale-to-List Ratio

100.6%

93 sales

How this home compares

List Price

$879,000

vs $1.01M median

13.2% below median

Price / Sq Ft

$227

vs $281 median

19.2% below median

Days on Market

95 days

vs 46 days median

49 days longer than median

Based on 26 active and 93 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of September 11, 2026.

Location

299 Redding Road, Redding, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,876

per month

  • Principal & Interest$4,566
  • Property Taxes$1,017
  • Insurance$293
  • 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
95
MLS #
24181978
MLS Status
Active

Similar Properties

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Listed By

Natalia Rathbauer

(914) 575-7735

William Pitt Sotheby's Int'l

(203) 968-1500

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 9/11/2026. 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 9/11/2026 at 8:40 PM UTC.