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299 Redding Road

Redding, Connecticut 06896

ACTIVE$859,000

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 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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$5,986

per 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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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 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.