206 Umpawaug Road
Redding, Connecticut 06896
- Beds
- 7
- Baths
- 8 | 5
- SqFt
- 13,094
- Acres
- 7.00
- Year Built
- 2008
- Neighborhood
- Umpawaug
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Exquisite Nantucket-style country estate magnificently sited on seven sprawling acres in Redding, CT's coveted Umpawaug neighborhood. Comprised of three extraordinary residences, this masterfully crafted 2008 HOBI award-winning compound offers 13,904 sf of carefully constructed living space with meticulous architectural details, effortlessly balancing timeless elegance with modern function. The main residence greets with a sweeping two story entry bathed in natural light, flanked by gracious formal living & dining rooms with fireplaces. The heart of the home, a chef's kitchen with custom cabinetry, high-end appliances, butler's pantry & French doors to an expansive terrace, seamlessly integrated with spectacular grounds. Additional main-level highlights include great room & study with fireplaces, steps from a serene covered porch; mudroom, full bath, & attached three-car garage. Upstairs, a primary suite sanctuary with fireplace, sitting room with wet bar, dressing room with custom cabinetry & spa-like bath with soaking tub & steam shower. Completing the 2nd floor, four additional bedrooms featuring en-suite baths & walk-in closets, family room and laundry. On the 3rd level, 2nd office, gym, half bath & ample storage. Elevator to wine cellar, home theater, billiards room & walkout au pair suite; commercial grade utilities & generator. Award-winning pool house, carriage house with in-law suite, heated gunite pool, spa & manicured grounds complete a remarkable legacy property.
Key Facts
- City/Town
- Redding
- Neighborhood
- Umpawaug
- Property / Style
- Single Family · Colonial
- Year Built
- 2008
- Days on Market
- 115 days
- Beds
- 7
- Baths
- 8 full · 5 half
- Living Area
- 13,094 sq ft
- Lot Size
- 7.00 acres
- Garage / Parking
- 6 garage
- Property Taxes
- $82,781 / Annually
Market Snapshot
The Redding Market
Single Family · trailing 12 months
Active Listings
25
16 under contract
Median List Price
$1.02M
25 active listings
Median Closed Price
$950,000
95 sales
Median Days on Market
57
25 active listings
Median $ / Sq Ft
$282
25 active listings
Sale-to-List Ratio
100.1%
95 sales
How this home compares
List Price
$7.72M
vs $1.02M median
7.5× the median
Price / Sq Ft
$590
vs $282 median
2.1× the median
Days on Market
115 days
vs 57 days median
58 days longer than median
Based on 25 active and 95 closed sales (trailing 12 mo) of single family in Redding. Source: SmartMLS · As of September 10, 2026.
Location
206 Umpawaug Road, Redding, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 3, 2026per month
- Principal & Interest$39,919
- Property Taxes$6,898
- Insurance$2,575
- 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
- Year Built
- 2008
- New Construction
- No/Resale
- Living Area
- 13,094 sq ft
- Below Grade
- 2,806 sq ft
Schools
- Elementary
- Redding
- High
- Joel Barlow
Interior
- Heating
- Hot Air
- Heat Fuel
- OilPropane
- Cooling
- Central Air
- Fireplaces
- 8
- Laundry
- Upper Level
- Laundry Location
- 1- Upper (Main Residence)2- Pool House
- Appliances
- Oven/RangeMicrowaveSubzeroDishwasherWasherDryerWine Chiller
- Basement
- FullHeatedStorageFully FinishedLiveable SpaceFull With Walk-Out
- In-Law Apartment
- YesOver GarageSeparate Entry
- Interior Features
- Audio SystemAuto Garage Door OpenerElevatorSecurity System
- Additional Rooms
- FoyerLaundry RoomMud RoomSitting RoomWine Cellar
Exterior & Lot
- Lot Size
- 7.00 acres
- Zoning
- R-2
- Garage / Parking
- 6 garage spacesAttached GarageDetached Garage
- Waterfront Details
- Not Applicable
- Water Source
- Private Well
- Sewer
- Septic
- Pool
- GuniteHeatedPool HouseSpaIn Ground Pool
- Construction
- ShakeStone
- Color
- Natural
- Roof
- Wood Shingle
- Foundation
- Masonry
- Exterior Features
- GrillTerraceBreezewayGarden AreaLightingGuest HouseFrench DoorsPatio
- Lot Description
- Level LotClearedProfessionally Landscaped
Listing & Financials
- Property Taxes
- $82,781 / Annually
- Days on Market
- 115
- MLS #
- 24164249
- 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 9/10/2026. 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 9/10/2026 at 5:40 AM UTC.