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206 Umpawaug Road

Redding, Connecticut 06896

ACTIVE$7,725,000
Beds
7
Baths
8 | 5
SqFt
13,094
Acres
7.00
Year Built
2008
Matt Caiola

Matt Caiola

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Guest HouseElevatorWine CellarPool6-Car Garage8 Fireplaces

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$49,392

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Lauren Parr

(347) 852-2599

Houlihan Lawrence

(203) 438-0455

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.