206 Umpawaug Rd

Redding, CT 06896

$7,725,000
Price
7
Beds
13,094 Sq. Ft.
$590 / Sq. Ft.
13,094
Sq. Ft.
$590
per Sq. Ft.
Get preapproved with Rocket Mortgage1
Welcome to 206 Umpawaug Road!
Masterfully Crafted 2009 HOBI Award-Winning Compound on 7 Magnificent Acres
Gracious Entry With Custom Millwork
Formal Living Room With Fireplace With Access To Covered Patio With Fireplace
Soaked With Natural Light
Distinguished Study With Custom Built-Ins & Millwork
Exquisite Coffered Ceilings, Fireplace & Wet Bar
Great Room For Sophisticated Gatherings
Chef's Kitchen With French Doors to Multiple Outdoor Living Spaces
Chef's Kitchen with Custom Cabinetry, Oversized Island & Designer Appliances
Stunning Sightlines Through Hall With Venetian Plaster Ceilings & Custom Lighting to Covered Porch
Mudroom With Full Bath, Elevator & 3-Car Attached Garage Access For Optimal Convenience
Butler's Pantry For Effortless Entertaining
Formal Dining Room Overlooking Picturesque Grounds
Formal Dining Room With Fireplace & Custom Built-Ins
Primary Bedroom Suite With Sitting Room With Wet Bar (Second Level)
Primary Suite Built-Ins & Fireplace (Second Level)
Primary Suite Custom Walk-In Closet (Second Level)
Primary Suite En-Suite Full Bath With Soaking Tub, Oversized Shower, Double Vanities & Private Commode (Second Level)
Front Bedroom with Built-Ins, Fireplace, Walk-In & Linen Closets (Second Level)
Front Bedroom En Suite Full Bathroom With Marble Finishes (Second Level)
Rear Bedroom With French Doors, Balcony & Walk-In Closet (Second Level)
Rear Bedroom En Suite Full Bath (Second Level)
Family Room With Private Powder Room (Second Level)
Office & Fitness Center With Half Bathroom & Ample Walk-In Attic Storage (Third Level)
Office With Custom Maple Built-In Cabinetry (Third Level)
Fitness Center (Third Level)
Wine Cellar & Tasting Room With Built-In Wet Bar & Dishwasher (Lower Level)
Home Theatre With Projector & Surround-Sound (Lower Level)
Billiards Room (Lower Level)
Custom Paneled Elevator Serving Three Floors (Lower, Main, Second)
Multiple Outdoor Gathering Spaces With Built-In Wolf Grilling Station
2012 Pool House of The Year by Tom Falciglia & Architect Jonathan Wagner
Modern Marvel With Retractable Glass Doors & 10' Custom LED Architectural Lighting
Cedar Lined Interior With Fireplace & Wet Bar
Kitchenette, Private Laundry, Half Bath, Outdoor Shower, Gas Fire Pit & Secondary Built-In Wolf Grill
Carriage Residence With Private In-Law/Au-Pair Suite
Soaring Vaulted Ceilings with Ample Natural Light
Sleek Kitchenette, Living Area With Fireplace, Studio Bedroom, Full Bathroom & Three Walk-In Closets (Upper Level)
A Picture Perfect Legacy Estate - Truly In A Class of Its Own

Description

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...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.
  1. Listed by Lauren Parr • Houlihan Lawrence
    P: (347)-852-2599 C: (347)-852-2599 lparr@houlihanlawrence.com

Property Details for 206 Umpawaug Road

Basement Description
Full, Heated, Storage, Fully Finished, Liveable Space, Full With Walk-Out
Direct Waterfront
No
Expected Active Date
05-21-2026
Garages Number
6
Neighborhood
Umpawaug
Style
Colonial
Garage Parking Info
Attached Garage, Detached Garage
Swimming Pool
Yes
LISTING UPDATED: 05/21/2026 04:05 AM

Property Details for 206 Umpawaug Road

StatusActive
MLS #24164249
Days on Market4
Taxes$80,254 / year
HOA Fees-
Condo/Co-op Fees-
Property TypeSingle Family
MLS TypeResidential
Year Built2008
Lot Size7.00 AC / 304,920 SF
CountyFairfield County
Get preapproved with Rocket Mortgage1

Location

Listing Courtesy of Houlihan Lawrence, Lauren Parr
Add your commute

Building Information for 206 Umpawaug Road

Stories-Year Built2008Building Size-Lot Size7.00 AC / 304,920 SF

Payment Calculator

Get preapproved with Rocket Mortgage1

$45,182 per month

30 year fixed, 6.36% Interest

Principal and Interest

$38,495

Property Taxes

$6,688

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Know your buying power with a preapproval and custom rate in minutes

Rocket Mortgage1

Property Information for 206 Umpawaug Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Route 107 North to Umpawaug Road; #206.
  • Elementary School: Redding
  • High School: Joel Barlow
  • Latitude: 41.303775
  • Longitude: -73.421475
  • Middle Jr High School: John Read
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $80,254
Interior and Exterior Features
Exterior Features
  • Exterior Features: Grill, Terrace, Breezeway, Garden Area, Lighting, Guest House, French Doors, Patio
  • Pool Description: Gunite, Heated, Pool House, Spa, In Ground Pool
  • Waterfront Description: Not Applicable
Interior Features
  • Appliances Included: Oven/Range, Microwave, Subzero, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Heated, Partially Finished, Floored, Walk-up
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 8
  • Home Automation: Built In Audio, Entertainment System, Lighting, Security System, Thermostat(s)
  • Interior Features: Audio System, Auto Garage Door Opener, Elevator, Security System
  • Laundry Room Info: Upper Level
  • Laundry Room Location: 1- Upper (Main Residence); 2- Pool House
  • Rooms Additional: Foyer, Laundry Room, Mud Room, Sitting Room, Wine Cellar
  • Rooms Total: 16
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,French Doors,Patio/Terrace,Hardwood Floor
  • Room Length: 15.0
  • Room Level: Main
  • Room Type: Living Room
  • Room Width: 17.0
Room 2
  • Room Entry Order: 10
  • Room Features: Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 15.0
Room 3
  • Room Entry Order: 11
  • Room Features: Balcony/Deck,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 21.0
  • Room Level: Upper
  • Room Type: Bedroom
  • Room Width: 14.0
Room 4
  • Room Entry Order: 12
  • Room Length: 8.0
  • Room Level: Upper
  • Room Type: Office
  • Room Width: 11.0
Room 5
  • Listing Key: 4E7FA212534C4DF8E0631A01100ACD2B
  • Room Entry Order: 13
  • Room Features: Half Bath,Hardwood Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Family Room
  • Room Width: 15.0
Room 6
  • Room Entry Order: 14
  • Room Features: Book Shelves,Built-Ins,Hardwood Floor,On 3rd Floor
  • Room Length: 17.0
  • Room Level: Upper
  • Room Type: Office
  • Room Width: 18.0
Room 7
  • Room Entry Order: 15
  • Room Features: Hardwood Floor,On 3rd Floor
  • Room Length: 25.0
  • Room Level: Upper
  • Room Type: Rec/Play Room
  • Room Width: 15.0
Room 8
  • Room Entry Order: 16
  • Room Features: Tile Floor,On 3rd Floor
  • Room Level: Upper
  • Room Type: Half Bath
Room 9
  • Listing Key: 4E7FA212534C4DF8E0631A01100ACD2B
  • Room Entry Order: 17
  • Room Features: Bedroom Suite,French Doors,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 12.0
  • Room Level: Lower
  • Room Type: Bedroom
  • Room Width: 25.0
Room 10
  • Room Entry Order: 18
  • Room Features: Wall/Wall Carpet
  • Room Length: 30.0
  • Room Level: Lower
  • Room Type: Rec/Play Room
  • Room Width: 23.0
Room 11
  • Room Entry Order: 19
  • Room Features: Wet Bar,Tile Floor
  • Room Length: 16.0
  • Room Level: Lower
  • Room Type: Other
  • Room Width: 12.0
Room 12
  • Room Entry Order: 2
  • Room Features: Built-Ins,Fireplace,Hardwood Floor
  • Room Length: 16.0
  • Room Level: Main
  • Room Type: Dining Room
  • Room Width: 19.0
Room 13
  • Room Entry Order: 20
  • Room Features: Wall/Wall Carpet
  • Room Length: 16.0
  • Room Level: Lower
  • Room Type: Media Room
  • Room Width: 23.0
Room 14
  • Room Entry Order: 21
  • Room Features: Tile Floor
  • Room Level: Lower
  • Room Type: Half Bath
Room 15
  • Room Entry Order: 22
  • Room Features: 9 ft+ Ceilings,Studio,Fireplace,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Length: 19.0
  • Room Level: Other
  • Room Type: Studio Apt
  • Room Width: 27.0
Room 16
  • Room Entry Order: 23
  • Room Features: Vaulted Ceiling,Full Bath,Walk-In Closet
  • Room Length: 12.0
  • Room Level: Other
  • Room Type: Bedroom
  • Room Width: 14.0
Room 17
  • Room Entry Order: 24
  • Room Features: Wet Bar,Fireplace,Partial Bath,Patio/Terrace,Sliders,Tile Floor
  • Room Length: 22.0
  • Room Level: Other
  • Room Type: Sun Room
  • Room Width: 19.0
Room 18
  • Room Entry Order: 3
  • Room Features: Built-Ins,Dining Area,French Doors,Island,Pantry,Hardwood Floor
  • Room Length: 30.0
  • Room Level: Main
  • Room Type: Kitchen
  • Room Width: 18.0
Room 19
  • Room Entry Order: 4
  • Room Features: Fireplace,Hardwood Floor
  • Room Length: 18.0
  • Room Level: Main
  • Room Type: Great Room
  • Room Width: 25.0
Room 20
  • Room Entry Order: 5
  • Room Features: Built-Ins,Fireplace,French Doors,Hardwood Floor
  • Room Length: 14.0
  • Room Level: Main
  • Room Type: Study
  • Room Width: 17.0
Property
Property and Assessments
  • Color: Natural
  • Construction Description: Frame
  • Exclusions: Inquire with Listing Agent
  • Exterior Siding: Shake, Stone
  • Foundation Type: Masonry
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Wood Shingle
  • Year Built: 2008
  • Year Built Source: Owner
  • Bank Owned Property: No
  • In Law Access: Over Garage, Separate Entry
  • In Law Apartment: Yes
  • Sq Ft Description: 10,288 Total AbvGr SF (Main - 8,565 SF; Pool House - 773; Carriage - 950)
  • Sq Ft Est Heated Below Grade: 2806
  • Living Area SQFT Per Public Records: 0
Lot Information
  • Lot Description: Level Lot, Cleared, Professionally Landscaped
  • Parcel Number: 2540984
  • Sq Ft Est Heated Above Grade: 10288.0
  • Sq Ft Total: 13094.0
  • Zoning: R-2
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Oil, Propane
  • Hot Water Description: Oil, Domestic
  • Radon Mitigation Air: Yes
  • Radon Mitigation Water: Yes
  • Sewage System: Septic
  • Water Source: Private Well
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 206 Umpawaug Road

DateEvent & SourcePriceAppreciation
Sep 5, 2012

Closed (Public Record)

Public Record #338032983

$2,700,000

-21.9% / yr

Aug 8, 2011

Closed (Public Record)

Public Record #313322658

$3,527,000—
DateEvent & SourcePrice
09/05/2012

Closed (Public Record)

Public Record #338032983

$2,700,000

-21.9% / yr

08/08/2011

Closed (Public Record)

Public Record #313322658

$3,527,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 206 Umpawaug Road

Taxable ValueLand$481,300Additions$2,235,500Total$2,716,800
Tax Record2024$80,254 ($6,688 / month)
Home Facts
Beds0Lot Size304,920 SqFtStyleSingle Family ResidenceZoningR-2CountyWESTERN CONNECTICUTAPNREDD M:20 L:62Fireplace TypeHas Fireplace

Schools near 206 Umpawaug Road

This home is within Redding School District.
Rating
School
Type
Grades
Distance
Redding Elementary School
Public - PK to 4
John Read Middle School
Public - 5 to 8
Joel Barlow High School
Public - 9 to 12
Rating
School
Distance
Redding Elementary School
PublicPK to 4

John Read Middle School
Public5 to 8

Joel Barlow High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

Similar Homes

Explore Nearby Homes

More information about 206 Umpawaug Road, Redding, CT 06896

206 Umpawaug Road is a single family home for sale in Redding, CT 06896. This property was listed for sale on May 18, 2026 by Houlihan Lawrence, it's currently listed at $7,725,000. It has been on the market for a total of 4 days and was last sold on September 5, 2012. This listing's school districts are Redding School District, Regional School District 09. Nearby schools include Redding Elementary School, John Read Middle School and Joel Barlow High School. 206 Umpawaug Road is a 7-bed, 13-bath, 13,094 sqft single family home built in 2008.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Houlihan Lawrence, Lauren Parr

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.