44 Umpawaug Road, Redding, CT 06896
OFF MARKET

44 Umpawaug Road
Redding, CT 06896

  • 4 Beds
  • 4 Baths
  • 3,268 sqft (on 3.22 acres)

$1,427,100

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $9,384/mo*

$1,427,100

Trulia Estimate
as of Aug 24, 2026
Est. Refi. Payment $9,384/mo*
4 Beds
4 Baths
3,268 sqft
(on 3.22 acres)

Home Value

Trulia Estimate
$1.43M
Since last month
Increased$3K (+0.2%)
Since last year
Increased$72K (+5.3%)
Since last sale
Increased$195K (+15.8%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +77% in the last 10 years
MonthEstimated value
2026
August 2026$1.42M
July 2026$1.42M
June 2026$1.44M
May 2026$1.44M
April 2026$1.42M
March 2026$1.42M
February 2026$1.37M
January 2026$1.38M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.12
Single-Family Home
$767,000
11/03/25
4
2.5
2,958
0.51
Single-Family Home
$939,000
02/17/26
4
3.5
4,641
0.66
Single-Family Home
$1,475,000
07/31/26
3
3.5
4,943
0.75
Single-Family Home
$940,000
03/30/26
4
3.5
3,578
0.18
Single-Family Home
$750,000
08/07/26
3
1.5
2,265
0.50
Single-Family Home
$840,000
08/21/26
3
3
2,182
0.91
Single-Family Home
$1,160,000
09/18/25
4
3.5
3,156
0.93
Single-Family Home
$1,400,000
07/09/26
4
3
3,907
0.22
Single-Family Home
$579,350
07/24/26
3
2
1,952

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
0.12
$767,000
4
2.5
2,958
Recently Sold
0.14
$814,100
3
3
2,674
Off Market
0.18
$750,000
3
1.5
2,265
Recently Sold
0.22
$579,350
3
2
1,952
Recently Sold
0.24
$585,900
2
1.5
1,540
Off Market
0.25
$879,200
3
2.5
2,550
Off Market
0.25
$778,500
3
2
1,769
Off Market
0.26
$997,300
3
2.5
3,594
Off Market
0.28
$1,226,000
4
3
3,020
Off Market
0.26
$499,000
-
-
-
For Sale
0.31
$788,100
3
2
1,974
Off Market

Local Information

  • Map ViewExplore the area around 44 Umpawaug Road.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2001
Lot Size
3.22 acres
Living Area
3,268 sqft
Price/Sqft
$437
Parking
3 Car Garage

About this House

Welcome to 44 Hilltop House; a stylish, sophisticated Contemporary retreat lovingly built by current owners featuring clean lines, vaulted ceilings, light wood, skylights, french doors and extra wide doorways and hallways to access the main floor rooms. The inviting Foyer opens to the large vaulted ceiling living room with skylights, gas fireplace and french doors leading out to the large side lawn, stone paths wending throughout professionally landscaped gardens lead to a stone terrace; formal dining room with french doors steps out to the lovely gardens; Kitchen featuring stainless appliances, granite counters and a tiled island, a walk-in pantry, a butler's pantry with a bar sink plus 2nd DW. A breakfast nook with sliders leads to a screened porch overlooking the gardens and terraces. Completing the main floor: a library/home ofc with french doors, a guest powder room, the primary bedroom suite, a separate laundry room; and a mudroom w 2nd powder rm leading to the 3 car garage. On the upper level find 3 bedrooms and 2 full baths (one ensuite) and a media/family room overlooking the Living Rm. The large lower level is waiting to be developed into more square footage; a game room; a home gym. This home has been designed to maximize the beauty of a Redding country setting and with comfort and quality as primary considerations. The cul-de-sac is owned and maintained by the 4 adjoining properties. Hilltop House borders on 2.50 A of Redding Land Trust never to be developed. Location is very convenient to the shops, banks, pharmacies, and great restaurants in the historic village of Georgetown and the charming town of Ridgefield - catching the Metro North train to Norwalk, Stamford and on to Manhattan is just a short drive to the Branchville Station..
44 Umpawaug Road, Redding, CT 06896 is a 4 bedroom, 5 bathroom, 3,268 sqft single-family home built in 2001. It last sold for $1,230,000 on Dec 7, 2023 (3% above the $1,200,000 asking price). It is currently off market. The Trulia Estimate is $1,427,100, with a rent estimate of $6,348/month.
Last check for updates: about 11 hours ago
Listed by Sharon Hoverman, (203) 733-5073
Coldwell Banker Realty, (203) 438-9000
Margi Esten, (203) 241-8453
Coldwell Banker Realty, (203) 438-9000
Bought with: Sharon Hoverman, (203) 733-5073, Coldwell Banker Realty, (203) 438-9000
Co-Buyer's Agent: Margi Esten, (203) 241-8453, Coldwell Banker Realty, (203) 438-9000
Source: Smart MLS, MLS#170602532

Home Details for 44 Umpawaug Road

Interior Features

Interior Details
Basement: Full,Crawl Space,Unfinished,Concrete,Interior Entry,Storage SpaceNumber of Rooms: 9Types of Rooms: Master Bedroom, Bedroom, Master Bathroom, Bathroom, Dining Room, Family Room, Kitchen, Library, Living Room
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 5Number of Bathrooms (full): 3Number of Bathrooms (half): 2
Dimensions and Layout
Living Area: 3268 Square Feet
Appliances & Utilities
Appliances: Gas Cooktop, Oven, Refrigerator, Dishwasher, Washer, Dryer, Water HeaterDishwasherDryerLaundry: Main Level,Mud RoomRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: Screened, TerraceExterior: Garden, Stone WallFoundation: Concrete PerimeterGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageHas Open ParkingParking Spaces: 3Parking: Attached,Private,Asphalt
Frontage
Not on Waterfront
Water & Sewer
Sewer: Septic Tank
Finished Area
Finished Area (above surface): 3268 Square Feet

Property Information

Year Built
Year Built: 2001
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Contemporary
Building
Construction Materials: Shingle Siding, Wood SidingNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 1947851

Price & Status

Price
List Price: $1,200,000
Status Change & Dates
Off Market Date: Thu Nov 16 2023Possession Timing: Nego

Active Status

MLS Status: Closed

Location

Direction & Address
City: ReddingCommunity: Umpawaug
School Information
Elementary School: ReddingJr High / Middle School: John ReadHigh School: Joel Barlow

Building

Building Area
Building Area: 3268 Square Feet

Community

Community Features: Lake, Library, Medical Facilities, Park, Playground, Shopping/Mall, Tennis Court(s)
Other
Playground

HOA

No HOA

Lot Information

Lot Area: 3.22 Acres

Miscellaneous

BasementMls Number: 170602532Attic: Access Via HatchAbove Grade Unfinished Area: 3268

Additional Information

HOA Amenities: None

Price and Tax history

DateEventPrice
Dec 7, 2023
Source: Smart MLS #170602532
Sold
$1,230,000
Nov 18, 2023
Source: Smart MLS #170602532
Pending
$1,200,000
Oct 20, 2023
Source: Smart MLS #170602532
Listed For Sale
$1,200,000
Dec 12, 2000
Source: Smart MLS #98040711
Sold
$242,500
May 19, 2000
Source: Smart MLS #98040740
Sold
$260,000

Market trends in Redding

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
34
5
MoM

Around this home

The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Redding

At least 41 Trulia users voted on each feature.
  • 96 % Say there's wildlife

  • 91 % Say parking is easy

  • 88 % Say car is needed

  • 87 % Say there's holiday spirit

  • 86 % Say it's dog friendly

  • 84 % Say it's quiet

  • 76 % Say yards are well-kept

  • 71 % Say they plan to stay for at least 5 years

  • 68 % Say neighbors are friendly

  • 63 % Say there are community events

  • 59 % Say people would walk alone at night

  • 42 % Say kids play outside

  • 33 % Say it's walkable to restaurants

  • 12 % Say it's walkable to grocery stores

  • 12 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Drewluca
    "Many families; safe; lots of space. Great place to live and raise kids. Friendly and close enough to everything to make it pleasant. "
  • Helga P.
    "We work from home. Therefore, we do not have a commute unless we have outside business meetings or other work related engagements. "
  • Betsy M.
    "We have potlucks and cookouts on our lane, and spontaneous get-togethers for cocktails. People always Everyone on our lane pitches in to help one another whenever needed. I wouldn’t say that’s the case for Redding as a whole, but definitely true on our lane!"
  • Agustahalla
    "A great place for small children. We work from home. This is a very peaceful place without being too remote. I love living here. ;-)"
  • Agustahalla
    "Quiet. Relatively safe for children. Great things to do outdoors near by. The town has organized great camps for kids through the summertime."
  • Jenbain23
    "My commute varies as I work at different locations. Fairfield County in general is horrible for rush hour traffic but when traveling North it could be less congested. "
  • Jenbain23
    "Love the neighborhood, but I don’t love the amount of people in town who have little awareness of appropriate fiscal responsibility with town finances."
  • Deidreyw
    "Nice small town, with plenty to do nearby. Great schools, many stores/shopping areas in surrounding towns and safe areas."
  • Deidreyw
    "It’s a nice small town with great schools, a lot of parks, and things to do in the area if you have little ones. Also, really nice restaurants in the area, so you don’t need to go far. There is a train station nearby and close to lots of shopping, highways and New York City!"
  • einarulfsson
    "Redding is the best Value in Fairfield County, amazing Schools, parks and recreation available."
  • Janeausten
    "Fabulous town full of wonderful parks and hiking trails. Town library started by Mark Twain and a hub of activity. Summer Concerts on the Green gather young and old to enjoy music and fun together. Excellent schools- always in top 10. "
  • Pdunay
    "Live and work here. Beautiful and peaceful country life. Great schools and very safe. "
  • rtklarsfeld
    "Part of prestigious Farview Farm Association with pool club and tennis courts. Completely updated in 2013. Custom gourmet kitchen of your dreams with double European dishwashers, Wolf 6 burner range, double ovens, warming drawer, Sub-Zero All Refrigerator and All Freezer . 3 car garage. Finished lower level 785 sq/ft for a total of 4,422 sq/ft."

LGBTQ Local Legal Protections

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Frequently asked questions about 44 Umpawaug Road

  • What is 44 Umpawaug Road estimated to be worth?
    Trulia's estimated value for 44 Umpawaug Road in Redding, CT is $1,427,100.
  • What is the price history for 44 Umpawaug Road?
    44 Umpawaug Road in Redding, CT last sold for $1,230,000 in December 2023.
  • Is Redding a buyer's or seller's market?
    Redding is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Redding?
    Residents describe Redding, CT as easy to park in, dog-friendly, and quiet. Most residents say you need a car. See recently sold homes in Redding, CT.
  • Does 44 Umpawaug Road have air conditioning?
    Yes, 44 Umpawaug Road in Redding, CT has air conditioning.
  • Does 44 Umpawaug Road have laundry facilities?
    Yes, 44 Umpawaug Road in Redding, CT has in-unit laundry.

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