Off market may 2021 for $2.3M

$3,747,843

Est. refi paymentEst. refi $15,783/mo

•

5,562

sq ft

36 Chestnut Woods Rd, Redding, CT 06896

About this home

Most spectacular country estate on 11.58 acres with scenic pond in prestigious West Redding location. This breathtaking country compound includes the gracious main home with 5,562 sf including 1,003 sf 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 & full bath; legal rental cottage with living room, kitchen & full bath (additional 741 sf); & state of the art pool house (additional 504 sf). Highest attention to detail both inside & out w/apprx $500K in recent improvements by current owner including brand new slate roof; stunning kitchen & baths; new a/c; new lighting; full studio renovation; new pool house; updates in cottage including hardwood installation; full interior painting; fit out of main garage as a catering kitchen; hardwood installation in lower level; sun porch w/retractable screen; & so many other tasteful touches which have polished this home to exquisite perfection. Casual elegance abounds w/6 fireplaces including the LR w/exposed beams, dining room, paneled library, MBR suite, 2nd ensuite BR, & lower level billiards room. Picturesque grounds w/heated gunite pool; private pond; outbuildings including detached garage & barn/shed; plus potential to subdivide & 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 & just 61 miles to Midtown!

Single-familyProperty Type

1942Year Built

11.58 acresLot Size

$674Est. Price/Sq.Ft.

4 car garageParking

Listed by Laura Ancona • William Pitt Sotheby's Int'l

Bought with Laura Ancona • William Pitt Sotheby's Int'l

Source:Smart MLS #170375137

Redfin Estimate

$3,747,843

$1.4M since sold in May 2021$91K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 131.3% higher than the average sale price ($1.62M) of 6 comparable homes.

SOLD OCT 6, 2026
$1,800,000
A
4 beds4.5 baths6,108 sq ft
24 Mark Twain Ln, Redding, CT 06896
SOLD MAY 27, 2026
$1,585,000
B
4 beds3.5 baths4,548 sq ft
36-40 Fox Run Rd, Redding, CT 06896
SOLD DEC 23, 2025
$1,525,000
C
4 beds3.5 baths4,146 sq ft
61 Marchant Rd, Redding, CT 06896
SOLD AUG 21, 2026
$1,560,000
D
4 beds4 baths4,786 sq ft
74 George Hull Hill Rd, Redding, CT 06896
SOLD DEC 18, 2025
$1,550,000
E
4 beds4.5 baths4,620 sq ft
33 Peaceable St, Redding, CT 06896
SOLD JUL 31, 2026
$1,700,000
F
4 beds3.5 baths3,854 sq ft
42 Topstone Rd, Redding, CT 06896

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Earn from this home

Sell

$1,829,632

Est. take-home

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Est. cash available

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Market trends in 06896, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

103.3%

0.6% MoM

Median sale price

$967K

$284 MoM

Avg. days on market

41d

8 days MoM

Recently sold homes

3 MoM

New listings for sale

NEW 16 HRS AGO
$1,295,000
4 beds3.5 baths3,990 sq ft
11 Fox Run Rd, Redding, CT 06896
$975,000
4 beds3.5 baths4,325 sq ft
123 Cross Hwy, Redding, CT 06896
$1,500,000
4 beds3 baths3,588 sq ft
Redding, CT 06896
$849,000
4 beds2.5 baths2,930 sq ft
72 Orchard Dr, Redding, CT 06896
3D WALKTHROUGH
$1,395,000
6 beds4 baths4,033 sq ft
12 Werf Dr, Redding, CT 06896
$1,100,000
4 beds2.5 baths2,947 sq ft
77 Wayside Ln, Redding, CT 06896
VIDEO TOUR
$7,400,000
6 beds6 baths9,420 sq ft
63 Turney Rd, Redding, CT 06896
$899,000
5 beds3 baths3,183 sq ft
24 Deer Spring Rd, Redding, CT 06896
See all

Provided by Redfin

Sale history for 36 Chestnut Woods Rd

Date

Event

Price

Smart MLS #170375137

May 28, 2021

Sold

$2,380,000

$428/sq ft

Apr 22, 2021

Contingent

—

Mar 1, 2021

Listed

$2,750,000

$494/sq ft

Feb 25, 2021

Coming Soon

$2,750,000

$494/sq ft

Smart MLS #170285791

Apr 28, 2020

Listing Removed

—

Apr 1, 2020

Listed

$2,495,000

$449/sq ft

Smart MLS #170170569

Dec 6, 2019

Listing Removed

—

Mar 7, 2019

Listed

$2,495,000

$449/sq ft

Public Records

Aug 2, 2012

Sold

$2,150,000

$387/sq ft

Smart MLS #98518218

Oct 19, 2011

Listed

$2,499,000

$449/sq ft

Smart MLS #98496499

Oct 19, 2011

Listing Removed

—

Mar 11, 2011

Listed

$2,999,999

$539/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$46,270 (+5.6%)

$331,000 + $1,340,000

$1,671,000

2022

$43,815 (+1.5%)

$347,000 + $967,200

$1,314,200

2021

$43,158

$347,000 + $967,200

$1,314,200

2020

$43,158

$347,000 + $967,200

$1,314,200

2019

$43,158 (+3.5%)

$347,000 + $967,200

$1,314,200

2018

$41,686 (+2.6%)

$347,000 + $967,200

$1,314,200

2017

$40,612 (+1.3%)

$482,700 + $888,400

$1,371,100

2016

$40,091 (+9.4%)

$482,700 + $888,400

$1,371,100

2014

$36,661

$482,700 + $785,400

$1,268,100

Tax history for 36 Chestnut Woods Rd

Year

Property tax

Land + Additions

Assessment*

2023

$46,270 (+5.6%)

$331,000 + $1,340,000

$1,671,000

2022

$43,815 (+1.5%)

$347,000 + $967,200

$1,314,200

2021

$43,158

$347,000 + $967,200

$1,314,200

2020

$43,158

$347,000 + $967,200

$1,314,200

2019

$43,158 (+3.5%)

$347,000 + $967,200

$1,314,200

2018

$41,686 (+2.6%)

$347,000 + $967,200

$1,314,200

2017

$40,612 (+1.3%)

$482,700 + $888,400

$1,371,100

2016

$40,091 (+9.4%)

$482,700 + $888,400

$1,371,100

2014

$36,661

$482,700 + $785,400

$1,268,100

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Beds

—

Baths

—

Stories

—

Lot width

—

Lot depth

—

Lot size

11.58 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Fairfield County

APN

271169

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Detached Garage
Garages Number: 4

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 11
Laundry Room Info: Lower Level
In-Law Apartment: Yes
In-Law Access: First Floor
Fireplaces Total: 6
Cooling System: Central Air
Appliances Included: Gas Range, Refrigerator, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 5
# of Baths (Half): 2

Bedroom Information
Beds Total: 4

Room Information
Rooms Additional: Foyer, Laundry Room, Mud Room
Room Count: 11
Basement Description: Full, Partially Finished
Has Attic

Exterior

Exterior Features
Roof Information: Slate
Exterior Siding: Brick, Stone
Exterior Features: Balcony, Barn, Cabana, French Doors, Garden Area, Guest House, Lighting, Patio, Underground Sprinkler

Lot Information
Lot Description: Level Lot, Fence - Partial, Fence - Stone

Pool Information
Swimming Pool
Pool Description: Pool House, In Ground Pool, Heated

Building Information
Foundation Type: Concrete, Stone
Construction Description: Frame
Color: White

Property Information
Waterfront Description: Pond
Property Type: Single Family For Sale
Driveway Type: Private, Paved

Financial

Assessments Information
Assessed Value: $1,314,200

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil
Heat Type: Hot Air, Radiator
Heat Fuel Type: Oil, Propane
Fuel Tank Location: Above Ground

Location

School Information
Middle Jr High School: John Read
High School: Joel Barlow
Elementary School: Redding

Location Information
State: Connecticut
Directions: Topstone or Marchant to Chestnut Woods to #36
Direct Waterfront
County: Fairfield

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 11.58 acres
Style: Other
Year Built: —
Year Renovated: —
County: Fairfield County
APN: 271169

Home facts updated by county records on Jul 13, 2023

Around this home

Schools

K - 12
Preschool & daycare

John Read Middle School

Public 5-8 • Assigned • 2.0mi

9/10

Joel Barlow High School

Public 9-12 • Assigned • 5.3mi

9/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 98° expected this year, 15 days in 30 years

4/10 Wind Factor

22% chance of strong winds in next 30 years

4/10 Air Factor

3 unhealthy days expected this year, 5 days in 30 years

Provided by First Street

Historical weather

Redding, CT • 06896

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

Try the sun simulator tool to see how light moves across the property at different times of day and year.

Provided by Shadowmap

Estimated sale price

$3.56M – $4.31M

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New listings for sale in 06896

NEW 16 HRS AGO

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11 Fox Run Rd, Redding, CT 06896

Luxury appliances • In ground pool • Separate structure

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3D WALKTHROUGH

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Wraparound driveway • Classic fireplace • Open-concept layout

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VIDEO TOUR

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39.23 acres • Pristine woodlands • Abundant wildlife

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Chef's kitchen • Expansive deck • Primary suite

Home values near 36 Chestnut Woods Rd

Data from public records.

Address	Redfin Estimate
41 Chestnut Woods Road, Redding, CT 5 Beds \| 3.5 Baths \| 5200 Sq. Ft.	$1,529,528
48 Chestnut Woods Road, Redding, CT 4 Beds \| 3.5 Baths \| 5501 Sq. Ft.	$2,227,824
49 Chestnut Woods Road, Redding, CT 3 Beds \| 3 Baths \| 1680 Sq. Ft.	$916,318
29 Chestnut Woods Road, Redding, CT 3 Beds \| 2.5 Baths \| 3354 Sq. Ft.	$1,452,444
45 Chalburn Road, Redding, CT 5 Beds \| 3.5 Baths \| 3916 Sq. Ft.	$2,768,496
68 Topstone Road, Redding, CT 1 Beds \| 2.5 Baths \| 1786 Sq. Ft.	$1,045,673
14 Charlie Hill Road, Redding, CT 4 Beds \| 4 Baths \| 5400 Sq. Ft.	$1,928,986

Address	Redfin Estimate
23 Chestnut Woods Road, Redding, CT 3 Beds \| 3.5 Baths \| 3322 Sq. Ft.	$1,604,576
45 Chestnut Woods Road, Redding, CT 4 Beds \| 2 Baths \| 1974 Sq. Ft.	$745,547
54 Chestnut Woods Road, Redding, CT 3 Beds \| 3 Baths \| 1874 Sq. Ft.	$937,548
47 Chestnut Woods Road, Redding, CT 4 Beds \| 3.5 Baths \| 3788 Sq. Ft.	$1,439,702
69 Topstone Road, Redding, CT 4 Beds \| 2.5 Baths \| 4284 Sq. Ft.	$954,479
46 Chalburn Road, Redding, CT 3 Beds \| 2 Baths \| 2255 Sq. Ft.	$1,701,829
52 Topstone Road, Redding, CT 3 Beds \| 2.5 Baths \| 2518 Sq. Ft.	$1,285,102

Address	Redfin Estimate
53 Chestnut Woods Road, Redding, CT 4 Beds \| 4 Baths \| 3425 Sq. Ft.	$1,762,647
33 Chestnut Woods Road, Redding, CT 4 Beds \| 6.5 Baths \| 7241 Sq. Ft.	$5,167,128
43 Chestnut Woods Road, Redding, CT 4 Beds \| 2.5 Baths \| 2684 Sq. Ft.	$1,159,067
1 Chestnut Woods Road, Redding, CT 3 Beds \| 3 Baths \| 2783 Sq. Ft.	$2,225,484
67 Topstone Road, Redding, CT 3 Beds \| 2 Baths \| 2500 Sq. Ft.	$1,075,059
48 Chalburn Road, Redding, CT 3 Beds \| 2.5 Baths \| 1634 Sq. Ft.	$906,593
44 Chalburn Road, Redding, CT 4 Beds \| 3 Baths \| 3983 Sq. Ft.	$1,432,039

Property information provided by Smart MLS when last listed in 2021. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06896, CT

Sale history for 36 Chestnut Woods Rd

Tax history for 36 Chestnut Woods Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06896

Home values near 36 Chestnut Woods Rd

More real estate resources