260 Umpawaug Road
Redding, Connecticut 06896
- Beds
- 3
- Baths
- 2 | 1
- SqFt
- 5,817
- Acres
- 12.04
- Year Built
- 1986
- 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
Rare West Redding Opportunity: Massive Upside, Privacy & Unmatched Potential. An exceptional property nestled in one of West Redding's most prestigious estate areas. Spanning over 5,000 sq ft of partially finished space across 3 levels, this distinctive custom-built Contemporary Colonial sits on 12.04 private, park-like acres in a secluded woodland setting. 3 bedrooms include a main level Primary suite, 3 full baths, and 3 half baths. The main living areas are bathed in natural light through walls of windows, with multiple decks taking in the spectacular, tree-lined views. The expansive walk-out lower level adds versatility and flexible living space-ready to make it your own. Adding incredible value and utility is a separate, working two-bay barn-ideal for a contractor, landscape equipment, large vehicle storage, or a workshop. While the residence requires a full interior and exterior renovation, the structure, grounds, and premier location make this a rare value-add investment and an outstanding treasure. Bring your inspiration, passion, and ingenuity to restore and preserve the deep-rooted spirit and enduring legacy of this remarkable residence. Enjoy a sought-after Redding location convenient to the train, top-rated schools, local shopping, and commuter routes-all just 65 miles to the Upper West Side of Manhattan. A real diamond-in-the-rough to be sold "as is"- Price reflects condition.
Key Facts
- City/Town
- Redding
- Neighborhood
- Umpawaug
- Property / Style
- Single Family · Colonial,Contemporary
- Year Built
- 1986
- Days on Market
- 0 days
- Beds
- 3
- Baths
- 2 full · 1 half
- Living Area
- 5,817 sq ft
- Lot Size
- 12.04 acres
- Garage / Parking
- 4 garage · 6 total
- Property Taxes
- $29,382 / Annually
Market Snapshot
The Redding Market
Single Family · trailing 12 months
Active Listings
31
11 under contract
Median List Price
$997,000
31 active listings
Median Closed Price
$915,000
97 sales
Median Days on Market
50
31 active listings
Median $ / Sq Ft
$327
31 active listings
Sale-to-List Ratio
100.6%
97 sales
How this home compares
List Price
$1.45M
vs $997,000 median
45.4% above median
Price / Sq Ft
$249
vs $327 median
23.9% below median
Days on Market
0 days
vs 50 days median
50 days fresher than median
Based on 31 active and 97 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of October 23, 2026.
Location
260 Umpawaug Road, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Oct 22, 2026per month
- Principal & Interest$7,968
- Property Taxes$2,449
- Insurance$483
- 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
- Colonial,Contemporary
- Year Built
- 1986
- New Construction
- No/Resale
- Living Area
- 5,817 sq ft
- Below Grade
- 1,000 sq ft
Schools
- Elementary
- Redding
- High
- Joel Barlow
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Central Air
- Fireplaces
- 2
- Laundry
- Lower LevelMain Level
- Appliances
- Cook TopWall OvenDishwasher
- Basement
- FullStorageInterior AccessPartially FinishedLiveable SpaceFull With Walk-Out
- In-Law Apartment
- PossibleLower Level
- Interior Features
- Auto Garage Door OpenerCable - Available
- Additional Rooms
- Bonus RoomExercise RoomWorkshop
Exterior & Lot
- Lot Size
- 12.04 acres
- Zoning
- R-2
- Garage / Parking
- 4 garage spaces6 total parking spacesBarnAttached GaragePavedDrivewayPrivatePavedAsphaltCrushed Stone
- Waterfront
- Direct waterfront
- Waterfront Details
- RiverWalk to Water
- Water Source
- Private Well
- Sewer
- Septic
- Construction
- Clapboard
- Color
- Slate Grey
- Roof
- Wood Shingle
- Foundation
- Concrete
- Exterior Features
- BarnGuttersFrench DoorsPatioBalconyUnderground UtilitiesDeckGarden AreaStone Wall
- Lot Description
- SecludedInterior LotTreedBorders Open SpaceProfessionally LandscapedRolling
Listing & Financials
- Property Taxes
- $29,382 / Annually
- Days on Market
- 0
- MLS #
- 24211675
- 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 10/23/2026. 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 10/23/2026 at 11:10 PM UTC.