Off Market Apr 2015 for $2.2M

$3,315,467

Est. refi paymentEst. refi $15,966/mo

•

8,275

sq ft

165 Old Redding Rd, Weston, CT 06883

About this home

Completely renovated in 1988 and majestically nestled on 12.64 acres. The Harlan Estate is embraced by nearby Trout Brook Valley Preserve and the Saugatuck River Valley. This pristine property offers privacy, perennial views, and the perfect pinch of pizzazz. Enjoy rolling landscapes replete with gentle streams, native and perennial plantings, flowering trees, and meandering stonewalls. Follow the covered breezeway from the main residence to a magnificent guesthouse with gunite pool, spa, and surrounding stone patio. Over 8,000 sq ft of custom living space offering 5 bedrooms, 4 full and 1 half-baths, guest house, 2,200 bottle wine cellar, cedar closet, gunite pool, Omni synthetic grass tennis court, gazebo and professional gourmet kitchen.

An approved 2 acre building lot is part of this 12.64 acre estate. The lot is currently taxed at $6,650; if it were to be merged into the main property, it would save approximately $6,000, net of reflecting a small increase due to the extra acreage at the main property.

Single-familyProperty Type

1938Year Built

12.64 acresLot Size

$401Est. Price/Sq.Ft.

5 car garageParking

Listed by Molly Lane • William Raveis Real Estate

Bought with Non Member • Non-Member

Source:Smart MLS #99066380

Redfin Estimate

$3,315,467

$1.0M since sold in April 2015$1.4M since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 80.7% higher than the average sale price ($1.83M) of 6 comparable homes.

SOLD AUG 15, 2026
$1,170,000
A
5 beds4 baths4,344 sq ft
195 Steep Hill Rd, Weston, CT 06883
SOLD AUG 3, 2026
$1,400,000
B
5 beds4 baths4,202 sq ft
4041 Redding Rd, Fairfield, CT 06824
SOLD JUL 23, 2026
$2,000,000
C
4 beds4.5 baths4,312 sq ft
23 Old Stage Coach Rd, Weston, CT 06883
SOLD DEC 1, 2025
$1,252,500
D
5 beds4.5 baths4,898 sq ft
29 Old Stage Coach Rd, Weston, CT 06883
SOLD AUG 18, 2026
$1,850,000
E
5 beds4.5 baths5,700 sq ft
3233 North St, Fairfield, CT 06824
SOLD JUL 20, 2026
$3,335,000
F
5 beds4.5 baths6,456 sq ft
290 Lyons Plain Rd, Weston, CT 06883

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Sell

$1,757,074

Est. take-home

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Est. cash available

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Rent

$4,324/mo

Redfin rental estimate

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Market trends in 06883, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

106.1%

+0.2% MoM

Median sale price

$1.5M

$43K MoM

Avg. days on market

29d

0 days MoM

Recently sold homes

4 MoM

New listings for sale

OPEN TODAY, 1PM TO 3PM
$1,850,000
6 beds4.5 baths6,852 sq ft
24 Langner Ln, Weston, CT 06883
COMING SOON
$1,850,000
5 beds5.5 baths5,866 sq ft
10 Weddington Ln, Weston, CT 06883
$1,595,000
4 beds3.5 baths4,883 sq ft
227 Newtown Tpke, Weston, CT 06883
OPEN TODAY, 12PM TO 3PM
$2,000,000
3 beds3 baths3,039 sq ft
46 Valley Forge Rd, Weston, CT 06883
$1,299,900
5 beds3 baths3,437 sq ft
1 Greenlea Ln, Weston, CT 06883
OPEN TODAY, 2PM TO 4PM
$2,449,000
5 beds6 baths6,073 sq ft
5 Aspetuck Gln, Weston, CT 06883
$3,200,000
4 beds5 baths6,198 sq ft
32 Bernhard Dr, Weston, CT 06883
OPEN TODAY, 1PM TO 3PM
$2,189,000
5 beds4.5 baths5,912 sq ft
36 Old Orchard Dr, Weston, CT 06883
$1,795,000
5 beds4 baths4,577 sq ft
158 Steep Hill Rd, Weston, CT 06883
$1,795,000
6 beds4 baths4,900 sq ft
143 Old Hyde Rd, Weston, CT 06883
See all

Provided by Redfin

Sale history for 165 Old Redding Rd

Date

Event

Price

Public Records

Oct 19, 2021

Sold

$900,000

$109/sq ft

Smart MLS #170316169

Jul 31, 2021

Listing Removed

—

Mar 18, 2021

Relisted

—

Dec 3, 2020

Listing Removed

—

Oct 20, 2020

Relisted

—

Oct 19, 2020

Listing Removed

—

Jul 14, 2020

Listed

$1,795,000

$217/sq ft

Smart MLS #170195163

Jul 14, 2020

Listing Removed

—

Apr 13, 2020

Relisted

—

Apr 12, 2020

Listing Removed

—

May 24, 2019

Listed

$1,995,000

$241/sq ft

Public Records

May 1, 2015

Sold

$1,980,000

$239/sq ft

Smart MLS #99066380

Apr 30, 2015

Sold

$2,280,000

$276/sq ft

Feb 7, 2015

Listing Removed

—

May 22, 2014

Listed

$2,425,000

$293/sq ft

Smart MLS #99027030

Nov 15, 2013

Listing Removed

—

May 15, 2013

Listed

$2,050,000

$248/sq ft

Smart MLS #98496593

Dec 31, 2012

Listing Removed

—

Apr 11, 2011

Listed

$1,799,000

$217/sq ft

Smart MLS #98410158

Mar 11, 2011

Listing Removed

—

Feb 18, 2009

Listed

$3,995,000

$483/sq ft

Smart MLS #98350677

Feb 12, 2009

Listing Removed

—

Sep 21, 2007

Listed

$5,000,000

$604/sq ft

Smart MLS #98272421

Sep 20, 2007

Listing Removed

—

Mar 3, 2006

Listed

$5,500,000

$665/sq ft

Public Records

Sep 9, 2004

Sold

$416,668

$50/sq ft

Public Records

Mar 28, 2003

Sold

$1,892,000

$229/sq ft

Smart MLS #97013569

May 4, 1998

Listing Removed

—

May 4, 1997

Listed

$3,000,000

$363/sq ft

Smart MLS #96014793

May 3, 1997

Listing Removed

—

May 3, 1996

Listed

$3,000,000

$363/sq ft

Smart MLS #95014526

Apr 30, 1996

Listing Removed

—

Apr 18, 1995

Listed

$3,400,000

$411/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$51,317 (+0.3%)

$601,380 + $950,870

$1,552,250

2022

$51,178 (+0.2%)

$601,380 + $950,870

$1,552,250

2021

$51,100 (+1.7%)

$601,380 + $950,870

$1,552,250

2020

$50,246

$601,380 + $950,870

$1,552,250

2019

$50,246 (−1.4%)

$601,380 + $950,870

$1,552,250

2018

$50,965 (+1.7%)

$576,400 + $1,157,700

$1,734,100

2017

$50,133 (+1.2%)

$576,400 + $1,157,700

$1,734,100

2016

$49,526 (−1.5%)

$576,400 + $1,157,700

$1,734,100

2013

$50,279

$835,400 + $1,269,200

$2,104,600

Tax history for 165 Old Redding Rd

Year

Property tax

Land + Additions

Assessment*

2023

$51,317 (+0.3%)

$601,380 + $950,870

$1,552,250

2022

$51,178 (+0.2%)

$601,380 + $950,870

$1,552,250

2021

$51,100 (+1.7%)

$601,380 + $950,870

$1,552,250

2020

$50,246

$601,380 + $950,870

$1,552,250

2019

$50,246 (−1.4%)

$601,380 + $950,870

$1,552,250

2018

$50,965 (+1.7%)

$576,400 + $1,157,700

$1,734,100

2017

$50,133 (+1.2%)

$576,400 + $1,157,700

$1,734,100

2016

$49,526 (−1.5%)

$576,400 + $1,157,700

$1,734,100

2013

$50,279

$835,400 + $1,269,200

$2,104,600

*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

4.5

Stories

Lot width

—

Lot depth

—

Lot size

8.73 Acres

Year renovated

2007

Sq. Ft.

6,695

Year built

1938

Style

Single Family Residential

County

Fairfield County

APN

404769

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 12, 2023.

Property details

Parking

Garage Information
Garage & Parking: Attached Garage, Detached Garage, Paved
Garages Number: 5

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 14
Laundry Room Location: 2nd Flr
Interior Features: Audio System, Central Vacuum, Security System
In-Law Apartment: Yes
Fireplaces Total: 3
Cooling System: Central Air, Heat Pump, Zoned
Appliances Included: Counter Grill, Cook Top, Dishwasher, Dryer, Freezer, Microwave, Oven/Range, Refrigerator, Wall Oven, Washer

Bathroom Information
# of Baths (Full): 4
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Foyer, Laundry Room, Wine Cellar, Workshop
Room Count: 12
Basement Description: Full, Heated, Partially Finished, Storage, Walk-out
Has Attic
Attic Description: Pull-Down Stairs, Storage Space

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Brick, Stucco
Exterior Features: Balcony, Cabana, French Doors, Gazebo, Guest House, Shed, Underground Sprinkler, Tennis Court, Terrace

Lot Information
Lot Description: Level Lot, Sloping Lot, Treed, Fence - Stone

Pool Information
Swimming Pool
Pool Description: Gunite, In Ground Pool, Pool House, Spa

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

Property Information
Waterfront Description: Beach Rights, Brook
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 6695

Financial

Assessments Information
Assessed Value: $1,958,200

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Heat Type: Hot Air, Radiant, Zoned
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Generator, Thermopane Windows

Location

HOA Information
Association Amenities: Golf Course, Health Club, Medical Facilities, Park, Playground/Tot Lot, Pool, Tennis Courts

School Information
Middle Jr High School: Weston
High School: Weston
Elementary School: Hurlbutt

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Health Club, Library, Medical Facilities, Park, Playground/Tot Lot, Pool, Tennis Courts
Directions: Driveway on Old Redding Road; Property runs along Valley Forge as well
County: Fairfield

Public facts

Beds: 5
Baths: 4.5
Sq. Ft.: 6,695
Stories: 2.0
Lot Size: 8.73 acres
Style: Single Family Residential
Year Built: 1938
Year Renovated: 2007
County: Fairfield County
APN: 404769

Home facts updated by county records on Jul 12, 2023

Other

Documents & Disclosures
Supplement Count Public: 3

Around this home

Schools

Weston Intermediate School

Public 3-5 • Assigned • 2.8mi

10/10

Weston Middle School

Public 6-8 • Assigned • 2.7mi

9/10

Weston High School

Public 9-12 • Assigned • 2.8mi

10/10

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

5/10 Heat Factor

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

6/10 Wind Factor

27% chance of strong winds in next 30 years

4/10 Air Factor

5 unhealthy days expected this year, 7 days in 30 years

Provided by First Street

Historical weather

Weston, CT • 06883

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.7 hours in June and 4.3 hours in December, placing it below the U.S. average for solar exposure.

8.7 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$3.15M – $3.81M

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Home values near 165 Old Redding Rd

Data from public records.

Address	Redfin Estimate
160 Old Redding Road, Weston, CT 4 Beds \| 3.5 Baths \| 3376 Sq. Ft.	$1,232,632
152 Old Redding Road, Weston, CT 4 Beds \| 3.5 Baths \| 3637 Sq. Ft.	$1,333,506

Address	Redfin Estimate
146 Old Redding Road, Weston, CT 4 Beds \| 4 Baths \| 3765 Sq. Ft.	$1,481,612
10 Bernhard Drive, Weston, CT 5 Beds \| 6 Baths \| 5328 Sq. Ft.	$1,840,724

Address	Redfin Estimate
159 Old Redding Road, Weston, CT 5 Beds \| 4 Baths \| 3369 Sq. Ft.	$1,593,275
15 Bernhard Drive, Weston, CT 4 Beds \| 3 Baths \| 4168 Sq. Ft.	$1,483,920

Property information provided by Smart MLS when last listed in 2014. This data may not match . Learn more.

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