187 Umpawaug Rd, Redding, CT 06896
OFF MARKET

187 Umpawaug Rd
Redding, CT 06896

  • 7 Beds
  • 7.5 Baths
  • 9,720 sqft (on 47.16 acres)

$8,110,800

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $52,127/mo*

$8,110,800

Trulia Estimate
as of Jul 9, 2026
Est. Refi. Payment $52,127/mo*
7 Beds
7.5 Baths
9,720 sqft
(on 47.16 acres)

Local Information

  • Map ViewExplore the area around 187 Umpawaug Rd.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Maple Hill Farm,tucked away on nearly 50 acres in rural Redding, CT is a Gentleman's Farm unlike any other. This unique country estate is both a luxurious retreat and a self-sustaining working farm and is one of the town's most coveted and intriguing properties. At the heart of the estate is the main residence,a multi-faceted country manor blending contemporary style with unrivaled amenities. The owners are dedicated stewards of this exceptional farm, which also features 3 antique guest homes, a state-of-the-art private recording studio and performing arts venue, a working barn, a sugar house, boat house, orchard, fields, old stone walls and a 300-foot stream with multiple waterfalls cascading into a 3-acre pond stocked with largemouth bass and brown trout. Additional amenities include a pig and chicken coop, tennis court, riding ring, ballfield, horse stalls and paddocks. Acres of riding and hiking trails traverse the property's woods and open space. In a nod to Winnie-the-Pooh a local chainsaw artist added a whimsical component to the trails by creating wood carvings of A.A. Milne's beloved characters. Maple Hill Farm,  situated an hour from NYC, epitomizes a refined way of life with its verdant setting and unparalleled array of living, farming, entertaining and recreational opportunities. The property is deeply rooted in the highly desirable community of Redding, which takes pride in its past as it looks to its future. Maple Hill Farm...an incomparable residence, a sustainable farm and an idyllic haven from the hustle and bustle of urban life.
187 Umpawaug Rd, Redding, CT 06896 is a 7 bedroom, 9 bathroom, 9,720 sqft single-family home built in 2014. It last sold for $7,095,500 on Sep 27, 2023. It is currently off market. The Trulia Estimate is $8,110,800, with a rent estimate of $6,797/month.

Home Highlights

Parking
No Info
Outdoor
Patio, Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago

Home Details for 187 Umpawaug Rd

Interior Features

Heating & Cooling
Heating: OtherAir ConditioningCooling System: CentralHeating Fuel: Other
Interior Details
AtticNumber of Rooms: 13
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Hardwood
Security
Security System

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherPatio
Pool
Pool

Property Information

Year Built
Year Built: 2014
Property Type / Style
Property Type: Single Family Home

Community

Units in Building: 1

Lot Information

Lot Area: 47.16 acres

Building

Fitness & Sports
Tennis Court

Price History for 187 Umpawaug Rd

DatePriceEventSource
09/27/2023$7,095,500Sold
N/A
01/01/2023ListingRemovedSmart MLS #170537259
11/21/2022$11,000,000PriceChange
Smart MLS #170537259
08/17/2022$13,000,000Listed For SaleSmart MLS #170292028
04/07/2021ListingRemovedWilliam Pitt and Julia B. Fee Sotheby's International Realty
01/10/2021$16,000,000PriceChange
Agent Provided
05/15/2020$19,000,000Listed For SaleAgent Provided
11/29/2012$11,875,000Sold
Smart MLS #99004337
11/19/1994$855,000Sold
Smart MLS #94011154

Market trends in Redding

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
Sale-to-List Price
Price per sq ft
Available listings
49
20
MoM
Skip to last item
  • Results are loading
Skip to first item

Property Tax and Assessment

Year2025
Tax$76,468
Assessment$2,588,640
Home facts updated by county records

Comparable Sales for 187 Umpawaug Rd

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
0.64
Single-Family Home
$1,600,000
11/18/25
5
3
3,407
0.85
Single-Family Home
$1,585,000
05/27/26
4
3.5
4,548
0.49
Single-Family Home
$800,000
06/23/26
4
2.5
3,092
0.67
Single-Family Home
$1,199,000
07/16/25
4
3.5
3,045
0.25
Single-Family Home
$785,000
05/26/26
3
2
1,610
0.45
Single-Family Home
$725,000
11/05/25
4
2
3,024
0.77
Single-Family Home
$725,000
07/24/25
5
3.5
3,786
0.87
Single-Family Home
$1,335,000
05/28/26
4
4
4,548
0.81
Single-Family Home
$1,245,000
11/05/25
4
3
4,020
0.81
Single-Family Home
$725,000
07/28/25
5
3.5
3,786

Nearby homes

Get a sense of prices in the area by checking nearby homes.
Skip to last item
Skip to first item

Assigned Schools

These are the assigned schools for 187 Umpawaug Rd.
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

Apartments for Rent

Skip to last item
Skip to first item

Homes for sale near 187 Umpawaug Rd

Skip to last item
Skip to first item

Off Market Homes Near 187 Umpawaug Rd

Skip to last item
Skip to first item