77 Wayside Lane
Redding, Connecticut 06896
- Beds
- 4
- Baths
- 2 | 1
- SqFt
- 2,947
- Acres
- 3.24
- Year Built
- 1997
- Neighborhood
- Umpawaug
- 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
Idyllic country charm meets modern luxury in this turnkey Cape Cod home, nestled on 3.24 private acres complete with your own tranquil, spring-fed pond! Step inside through a dramatic two-story entry to find gleaming, richly-hued hardwood floors flowing seamlessly throughout the entire home. Thoughtfully designed for both entertaining and everyday comfort, the layout features elegant formal living and dining rooms bathed in natural light. At the heart of the home is the chef's kitchen with chic creamy-white cabinetry, timeless soapstone countertops, premium appliances, and a generous center island. It opens directly to an inviting family room anchored by a cozy fireplace and sunny bay-window seating and to a charming screened porch. The highly desirable main-level primary suite serves as a peaceful retreat, featuring a lavish en-suite spa-inspired bath designed for pure relaxation. Upstairs, you will discover three generously proportioned bedrooms, a stylishly updated full bath, and an expansive bonus room illuminated by bright skylights-a versatile space ready to become your home office, private gym, media lounge, or playroom. Peace of mind comes built-in with extensive improvements, including fresh exterior paint (2023), a comprehensive kitchen renovation (2021), a new roof (2015), updated interior painting (2015-2021-2026), and a stylishly renovated hall bath(2022). A truly ideal blend of classic architectural charm, modern luxury, and scenic country privacy. A win-win!
Key Facts
- City/Town
- Redding
- Neighborhood
- Umpawaug
- Property / Style
- Single Family · Cape Cod
- Year Built
- 1997
- Days on Market
- 0 days
- Beds
- 4
- Baths
- 2 full · 1 half
- Living Area
- 2,947 sq ft
- Lot Size
- 3.24 acres
- Garage / Parking
- 2 garage · 3 total
- Property Taxes
- $18,316 / 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
$939,500
92 sales
Median Days on Market
62
27 active listings
Median $ / Sq Ft
$327
27 active listings
Sale-to-List Ratio
100.4%
92 sales
How this home compares
List Price
$1.10M
vs $995,000 median
10.6% above median
Price / Sq Ft
$373
vs $327 median
14.1% above median
Days on Market
0 days
vs 62 days median
62 days fresher than median
Based on 27 active and 92 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of November 6, 2026.
Location
77 Wayside Lane, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Nov 5, 2026per month
- Principal & Interest$5,961
- Property Taxes$1,526
- Insurance$367
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Redding
- Neighborhood
- Umpawaug
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Cape Cod
- Year Built
- 1997
- New Construction
- No/Resale
- Living Area
- 2,947 sq ft
Schools
- Elementary
- Redding
- High
- Joel Barlow
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 1
- Laundry
- Main Level
- Appliances
- Cook TopWall OvenMicrowaveRange HoodRefrigeratorIcemakerDishwasherWasherDryerWine Chiller
- Basement
- FullUnfinishedStorageGarage AccessInterior AccessConcrete Floor
- Interior Features
- Auto Garage Door OpenerCable - Pre-wiredCentral Vacuum
- Additional Rooms
- Bonus RoomExercise RoomFoyerLaundry RoomMud Room
Exterior & Lot
- Lot Size
- 3.24 acres
- Zoning
- R-2
- Garage / Parking
- 2 garage spaces3 total parking spacesAttached GarageDrivewayPrivateGravel
- Waterfront
- Direct waterfront
- Waterfront Details
- PondWalk to WaterView
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- Edgecomb Grey
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- Underground UtilitiesGuttersFrench Doors
- Lot Description
- Level LotRolling
Listing & Financials
- Property Taxes
- $18,316 / Annually
- Days on Market
- 0
- MLS #
- 24217394
- 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 11/6/2026. 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 11/6/2026 at 1:05 AM UTC.