36 Chestnut Woods Rd #R, Redding, CT 06896
OFF MARKET

36 Chestnut Woods Rd #R
Redding, CT 06896

  • 4 Beds
  • 6 Baths
  • 5,562 sqft

$1,563,100

Trulia Estimate
as of May 6, 2026
Est. Refi. Payment $10,041/mo*

$1,563,100

Trulia Estimate
as of May 6, 2026
Est. Refi. Payment $10,041/mo*
4 Beds
6 Baths
5,562 sqft

Homes for sale near 36 Chestnut Woods Rd #R

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Apartments for Rent

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Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

For rent, for sale at $2,495,000, or rent to own. This FURNISHED Rental includes full use of home, grounds, pool, and pool house but not caretaker cottage. Caretaker to remain on site. Spectacular country estate on 11.58 acres with scenic pond in prestigious West Redding location. This breathtaking compound includes the gracious main home with 5,562 square feet including 1,003 square feet in the dramatic lower level media/bar/billiard room; total 4 bedrooms, 5/2 fully remodeled baths; additional studio or guest quarters with private entry, bedroom, and full bath; plus state of the art pool house (additional 504 square feet). Highest attention to detail both inside and out with $400K in recent improvements by current owner including stunning kitchen and baths; new a/c; new lighting; full studio renovation; full pool house renovation; fit out of main garage as a catering kitchen; hardwood installation in lower level; sun porch with retractable screen; and so many other tasteful touches which have polished this home to exquisite perfection. Casual elegance abounds with 6 fireplaces including the living room with exposed beams; dining room; paneled library; master bedroom suite; 2nd ensuite bedroom; and lower level billiards room. Picturesque grounds include heated gunite pool; private pond; outbuildings including detached garage and barn/shed; plus potential to subdivide and permits in place to build a new large barn if desired. Bucolic privacy adjoining the 54 acre Connecticut Audubon Society's Edward Steichen Memorial Wildlife Preserve.
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.

Home Highlights

Parking
No Info
Outdoor
No Info
A/C
Heating only
HOA
None
Price/Sqft
No Info
Listed
No Info

Home Details for 36 Chestnut Woods Rd #R

Interior Features

Heating & Cooling
Heating: OtherHeating Fuel: Other
Interior Details
Number of Rooms: 11Wet Bar
Levels, Entrance, & Accessibility
Floors: Hardwood

Exterior Features

Exterior Home Features
Roof: OtherExterior: OtherSprinkler System

Property Information

Year Built
Year Built: 1942
Property Type / Style
Property Type: Multi Family

Price History for 36 Chestnut Woods Rd #R

DatePriceEventSource
04/29/2020$10,500ListingRemovedAgent Provided
04/09/2020$10,500Listed For RentAgent Provided
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Comparable Sales for 36 Chestnut Woods Rd #R

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
2.02
Multi-Family Home
$740,000
07/02/25
4
2
1,960
2.58
Multi-Family Home
$755,000
06/06/25
4
2.5
2,688
3.12
Multi-Family Home
$460,000
01/30/26
4
2
1,964
2.99
Multi-Family Home
$625,000
11/18/25
2
3
1,662
3.71
Multi-Family Home
$780,000
07/07/25
5
3
2,789
3.29
Multi-Family Home
$380,000
10/06/25
2
1
1,200
4.00
Multi-Family Home
$580,000
05/07/25
4
3
2,640
4.13
Multi-Family Home
$685,000
07/30/25
4
3
2,764
3.71
Multi-Family Home
$800,000
10/15/25
2
2
1,808
4.45
Multi-Family Home
$550,000
08/11/25
5
2.5
4,000

Assigned Schools

These are the assigned schools for 36 Chestnut Woods Rd #R.
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

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."

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Homes for rent near 36 Chestnut Woods Rd #R

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Off Market Homes Near 36 Chestnut Woods Rd #R

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36 Chestnut Woods Rd #R, Redding, CT 06896 is a 4 bedroom, 6 bathroom, 5,562 sqft multi-family built in 1942. This property is not currently available for sale. The current Trulia Estimate for 36 Chestnut Woods Rd #R is $1,563,100.