23 Benedict Hill Rd, New Canaan, CT 06840

Off market jul 2025 for $2.8M

$3,525,597

Est. refi paymentEst. refi $12,423/mo

•

6,070

sq ft

23 Benedict Hill Rd, New Canaan, CT 06840

About this home

Welcome to this exquisite stone and shingle home, an extraordinary masterpiece built in the timeless English Cotswold tradition. Updated in 1999 and again in the early 2000's, this impeccably designed home showcases unparalleled craftsmanship, and captivates with its attention to every detail, offering a truly custom living experience. As you step inside, you'll be greeted by the allure of Palladian windows, arched doorways, and meticulously crafted custom moldings that adorn the interiors. The ambiance of this home is one of elegance and charm, with a seamless blend of classic antiques and modern comforts, creating a harmonious living space. The heart of this enchanting estate is its stone pool, where you can bask in the sunlight and enjoy refreshing swims on warm summer days. A gated entrance leads to the meticulously landscaped gardens surrounding the fenced-in property, which boasts a myriad of vibrant flora and whimsical sculptures. This stone and shingle manor house offers a rare opportunity to reside in a truly unique and captivating residence. Embrace the charm of the English Cotswold tradition, paired with modern luxury and convenience, in this exceptional home.

Single-familyProperty Type

1969Year Built

3.3 acresLot Size

$581Est. Price/Sq.Ft.

3 car garageParking

Buyer's agent

Anissa Paolillo Redfin Corporation

Listed by Melissa Engel • Douglas Elliman of Connecticut

Listed by John Engel • Douglas Elliman of Connecticut

Source:Smart MLS #24080383

Redfin Estimate

$3,525,597

$726K since sold in July 2025$387K since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 12.2% higher than the average sale price ($3.14M) of 6 comparable homes.

SOLD SEP 9, 2026
$2,300,000
A
5 beds5 baths4,384 sq ft
599 N Wilton Rd, New Canaan, CT 06840
SOLD AUG 31, 2026
$2,600,000
B
5 beds4.5 baths4,348 sq ft
559 Cheese Spring Rd, New Canaan, CT 06840
SOLD AUG 31, 2026
$3,575,000
C
4 beds6 baths5,958 sq ft
610 Cheese Spring Rd, New Canaan, CT 06840
SOLD JUL 15, 2026
$3,600,000
D
5 beds4.5 baths5,300 sq ft
245 Benedict Hill Rd, New Canaan, CT 06840
SOLD JUN 15, 2026
$3,175,000
E
5 beds4.5 baths5,674 sq ft
374 Michigan Rd, New Canaan, CT 06840
SOLD JUL 3, 2026
$3,600,000
F
5 beds6 baths6,715 sq ft
323 Smith Ridge Rd, New Canaan, CT 06840

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Earn from this home

Sell

$1,128,143

Est. take-home

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Refinance

Est. cash available

Get cash now or lower your monthly rate

Rent

$4,791/mo

Redfin rental estimate

List your home for rent

Market trends in 06840, CT

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

108.1%

+0.4% MoM

Median sale price

$2.4M

$69K MoM

Avg. days on market

18d

1 days MoM

Recently sold homes

114

29 MoM

New listings for sale

$3,300,000
3 beds3.5 baths5,520 sq ft
321 Oenoke Rdg, New Canaan, CT 06840
NEW 9 HRS AGO
$880,000
3 beds1 bath960 sq ft
38 Urban St, New Canaan, CT 06840
COMING SOON
$1,049,000
3 beds1 bath1,450 sq ft
40 Ogden Rd, New Canaan, CT 06840
$850,000
3 beds2.5 baths1,360 sq ft
78 Hoyt St #78, New Canaan, CT 06840
$6,200,000
6 beds4.5 baths5,657 sq ft
631 West Rd, New Canaan, CT 06840
$3,450,000
5 beds4.5 baths3,715 sq ft
284 Park St, New Canaan, CT 06840
$3,695,000
6 beds6.5 baths7,102 sq ft
34 Sherwood Ln, New Canaan, CT 06840
$3,600,000
5 beds5.5 baths5,135 sq ft
716 Cheese Spring Rd, New Canaan, CT 06840
$1,499,000
4 beds3 baths2,478 sq ft
27 White Oak Shade Ln, New Canaan, CT 06840
$1,600,000
6 beds4 baths1,896 sq ft
164 New Norwalk Rd, New Canaan, CT 06840
See all

Provided by Redfin

Sale history for 23 Benedict Hill Rd

Date

Event

Price

Smart MLS #24080383

Jul 18, 2025

Sold

$2,800,000

$461/sq ft

Jun 4, 2025

Pending

—

Mar 13, 2025

Listed

$2,899,000

$478/sq ft

Smart MLS #24039135

Mar 10, 2025

Listing Removed

—

Sep 13, 2024

Listed

$2,950,000

$486/sq ft

Smart MLS #24007219

Aug 2, 2024

Listing Removed

—

Jun 17, 2024

Price Changed

$3,095,000

$510/sq ft

Apr 17, 2024

Listed

$3,295,000

$543/sq ft

SMARTMLS #170572159

Nov 20, 2023

Rental Removed

$17,000

$3/sq ft

Aug 24, 2023

Price Changed

$17,000

$3/sq ft

Jul 21, 2023

Listed for Rent

$22,000

$4/sq ft

Smart MLS #98190054

Mar 9, 2005

Listing Removed

—

Mar 9, 2004

Listed

$2,800,000

$461/sq ft

Smart MLS #98172430

Feb 11, 2004

Listing Removed

—

Aug 13, 2003

Listed

$3,250,000

$535/sq ft

Public Records

Jan 16, 2003

Sold

$2,025,000

$334/sq ft

Smart MLS #98135106

Jul 3, 2002

Listed

$2,389,000

$394/sq ft

Smart MLS #98115629

Apr 1, 2002

Listing Removed

—

Nov 6, 2001

Listed

$2,469,000

$407/sq ft

Smart MLS #98084723

Nov 30, 2001

Listing Removed

—

Oct 13, 2000

Listed

$2,585,000

$426/sq ft

Public Records

Aug 10, 1999

Sold

$740,000

$122/sq ft

Smart MLS #98026934

Sep 8, 1999

Listing Removed

—

Sep 12, 1998

Listed

$740,000

$122/sq ft

Public Records

Sep 24, 1982

Sold

$94,000

$15/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$32,530 (+3.1%)

$554,890 + $1,162,630

$1,717,520

2022

$31,551 (+1.2%)

$554,890 + $1,162,630

$1,717,520

2021

$31,190

$554,890 + $1,162,630

$1,717,520

2020

$31,190 (−0.4%)

$554,890 + $1,162,630

$1,717,520

2019

$31,328 (−8.3%)

$554,890 + $1,162,630

$1,717,520

2018

$34,168 (+1.7%)

$587,160 + $1,427,440

$2,014,600

2017

$33,583 (+2.2%)

$587,160 + $1,427,440

$2,014,600

2016

$32,858 (+5.0%)

$587,160 + $1,427,440

$2,014,600

2014

$31,307

$587,160 + $1,427,440

$2,014,600

Tax history for 23 Benedict Hill Rd

Year

Property tax

Land + Additions

Assessment*

2023

$32,530 (+3.1%)

$554,890 + $1,162,630

$1,717,520

2022

$31,551 (+1.2%)

$554,890 + $1,162,630

$1,717,520

2021

$31,190

$554,890 + $1,162,630

$1,717,520

2020

$31,190 (−0.4%)

$554,890 + $1,162,630

$1,717,520

2019

$31,328 (−8.3%)

$554,890 + $1,162,630

$1,717,520

2018

$34,168 (+1.7%)

$587,160 + $1,427,440

$2,014,600

2017

$33,583 (+2.2%)

$587,160 + $1,427,440

$2,014,600

2016

$32,858 (+5.0%)

$587,160 + $1,427,440

$2,014,600

2014

$31,307

$587,160 + $1,427,440

$2,014,600

*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

6.5

Stories

Lot width

—

Lot depth

—

Lot size

3.3 Acres

Year renovated

—

Sq. Ft.

5,170

Year built

1969

Style

Single Family Residential

County

Fairfield County

APN

188245

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
Garages Number: 3

Interior

Virtual Tour Information

Interior Information
Total Rooms: 13
Laundry Room Info: Lower Level
Interior Features: Auto Garage Door Opener, Cable - Available, Security System
Cooling System: Central Air
Appliances Included: Gas Cooktop, Wall Oven, Refrigerator, Freezer, Dishwasher, Compactor, Washer, Dryer

Bathroom Information
# of Baths (Full): 6
# of Baths (Half): 1

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Foyer, Laundry Room, Mud Room, Sitting Room, Wine Cellar
Basement Description: Partial, Fully Finished, Partial With Walk-Out
Has Attic
Attic Description: Finished, Floored, Walk-up

Exterior

Exterior Features
Roof Information: Wood Shingle, Metal
Exterior Siding: Shingle, Stone

Lot Information
Lot Description: Secluded, Lightly Wooded, Dry, Level Lot, Cleared, Professionally Landscaped

Pool Information
Swimming Pool
Pool Description: Gunite, Heated, Salt Water, In Ground Pool

Building Information
Foundation Type: Concrete
Construction Description: Frame

Property Information
Radon Mitigation Air
Radon Mitigation Water
Property Type: Single Family For Sale
Living Area SQFT Per Public Record: 5170

Financial

Assessments Information
Assessed Value: $1,852,900

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Domestic
Heat Type: Hot Air
Heat Fuel Type: Oil
Fuel Tank Location: In Basement

Location

School Information
High School: New Canaan
Elementary School: East

Location Information
State: Connecticut
Nearby Amenities: Private School(s), Public Rec Facilities, Public Transportation, Shopping/Mall
Directions: Take Valley Road to Benedict Hill Road
County: Fairfield

Public facts

Beds: 5
Baths: 6.5
Sq. Ft.: 5,170
Stories: 2.0
Lot Size: 3.3 acres
Style: Single Family Residential
Year Built: 1969
Year Renovated: —
County: Fairfield County
APN: 188245

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 3

Around this home

Schools

East School

Public K-4 • Assigned • 2.9mi

10/10

Saxe Middle School

Public 5-8 • Assigned • 4.1mi

10/10

New Canaan High School

Public 9-12 • Assigned • 4.3mi

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

4/10 Heat Factor

7 days above 99° expected this year, 16 days in 30 years

6/10 Wind Factor

27% 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

New Canaan, CT • 06840

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

$3.35M – $4.06M

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Home values near 23 Benedict Hill Rd

Data from public records.

Address	Redfin Estimate
67 Benedict Hill Rd, New Canaan, CT 3 Beds \| 3 Baths \| 2840 Sq. Ft.	$2,110,130
181 Benedict Hill Rd, New Canaan, CT 5 Beds \| 6 Baths \| 4925 Sq. Ft.	$3,027,324

Address	Redfin Estimate
187 Benedict Hill Rd, New Canaan, CT 7 Beds \| 6.5 Baths \| 5267 Sq. Ft.	$3,472,076
35 Benedict Hill Rd, New Canaan, CT 5 Beds \| 3.5 Baths \| 3313 Sq. Ft.	$1,834,161

Address	Redfin Estimate
77 Benedict Hill Rd, New Canaan, CT 5 Beds \| 4 Baths \| 3069 Sq. Ft.	$2,522,300
81 Benedict Hill Rd, New Canaan, CT 6 Beds \| 7 Baths \| 7807 Sq. Ft.	$4,101,775

Property information provided by Smart MLS when last listed in 2023. This data may not match . Learn more.

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About this home

Redfin Estimate

Earn from this home

Market trends in 06840, CT

Sale history for 23 Benedict Hill Rd

Tax history for 23 Benedict Hill Rd

Public record

Property details

Around this home

Schools

Lifestyle

Climate risks

Historical weather

Sun exposure

Nearby similar homes

New listings for sale in 06840

Home values near 23 Benedict Hill Rd

More real estate resources