Off market dec 2018 for $4.2M

$7,716,126

Est. refi paymentEst. refi $21,221/mo

•

15,750

sq ft

153 Chichester Rd, New Canaan, CT 06840

About this home

Dramatic impressive and masterfully built, this timeless stone and shingle English Manor House sits high on 4.6 private gated acres. Harmony & state-of-the-art amenities prevail throughout this 15,000sf estate designed for easy living and gracious entertaining. This “Smart House” includes 5,600sf activities building w/in-law apt, vanishing edge salt water pool and spa, 9 fireplaces, elevator, pool house, terrace w/outdoor kitchen & fireplace, garage space for 7 vehicles. Special and very convenient location to town & schools. Additional Rooms: Bedroom 6 on LL is 12x15.5 w/bath and 2-story Activity Room on the main floor is 34X49 w/fplc, built-ins and full bath. Apartment in Activities Bldg includes full kitch, LR, BR, Bath, laundry, terrace and garage. Extensive addendum in documents.

Single-familyProperty Type

2006Year Built

4.6 acresLot Size

$490Est. Price/Sq.Ft.

7 car garageParking

Listed by Mary Higgins • Halstead Real Estate

Listed by B.K. Bates • Houlihan Lawrence

Bought with Hannelore Kaplan • William Raveis Real Estate

Source:Smart MLS #170062874

Redfin Estimate

$7,716,126

$3.5M since sold in December 2018$186K since October

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 32.8% higher than the average sale price ($5.81M) of 6 comparable homes.

SOLD AUG 14, 2026
$6,838,000
A
5 beds8 baths9,473 sq ft
256 Country Club Rd, New Canaan, CT 06840
SOLD SEP 1, 2026
$4,700,000
B
5 beds7.5 baths7,443 sq ft
146 Lambert Rd, New Canaan, CT 06840
SOLD OCT 5, 2026
$7,000,000
C
5 beds5 baths7,259 sq ft
30 Oenoke Ln, New Canaan, CT 06840
SOLD APR 29, 2026
$6,785,000
D
7 beds8 baths9,114 sq ft
584 West Rd, New Canaan, CT 06840
SOLD APR 1, 2026
$5,715,000
E
6 beds6.5 baths8,020 sq ft
91 Sunset Hill Rd, New Canaan, CT 06840
SOLD MAY 28, 2026
$3,825,000
F
5 beds8.5 baths9,062 sq ft
73 Lake Wind Rd, New Canaan, CT 06840

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Earn from this home

Sell

$4,454,136

Est. take-home

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Est. cash available

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Market trends in 06840, CT

Last updated October 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-list price

106.9%

1.1% MoM

Median sale price

$2.3M

$126K MoM

Avg. days on market

20d

2 days MoM

Recently sold homes

103

8 MoM

New listings for sale

$6,495,000
6 beds7.5 baths11,607 sq ft
505 Country Club Rd, New Canaan, CT 06840
OPEN SAT, 12PM TO 2PM
$1,290,000
3 beds3.5 baths1,494 sq ft
176 Summer St Unit C, New Canaan, CT 06840
$1,599,000
5 beds3 baths3,184 sq ft
114 Pequot Ln, New Canaan, CT 06840
$2,895,000
4 beds4.5 baths6,222 sq ft
7 Park Ln, New Canaan, CT 06840
$5,999,500
5 beds6 baths10,655 sq ft
48 Driftway Ln, New Canaan, CT 06840
See all

Provided by Redfin

Sale history for 153 Chichester Rd

Date

Event

Price

GMLS #102441

Dec 31, 2018

Sold

$4,200,000

$267/sq ft

Jul 24, 2018

Delisted

—

Mar 20, 2018

Listed

$4,890,000

$310/sq ft

+24

Handsome, impressive & masterfully built, this timeless stone and shingle House sits on 4.6 private gated acres. Harmony & state-of-art amenities prevail throughout this 15,000SF estate designed for easy living & gracious entertaining. High ceilings thru out all floors. This ''smart house'' includes an attached 5,600SF 2 story multiple use building with own entrance and walk out in-law apt. Lovely vanishing edge salt water pool & spa, pool house, terrace with outdoor kitchen & FP, 9 FPs, garaging for 7 vehicles and much more. A fabulous walk out lower level w gym, wine cellar, game room w fp & bath. Special & very convenient location to New Canaan town & schools. Incredible value!

Smart MLS #170062874

Dec 31, 2018

Sold

$4,200,000

$267/sq ft

Jul 24, 2018

Listing Removed

—

May 7, 2018

Price Changed

$4,890,000

$310/sq ft

Mar 20, 2018

Listed

$5,295,000

$336/sq ft

Smart MLS #99171889

Jun 15, 2017

Listing Removed

—

Jan 31, 2017

Listed

$6,300,000

$400/sq ft

GMLS #98697

Feb 1, 2017

Listed

$6,300,000

$400/sq ft

Smart MLS #99158572

Dec 15, 2016

Listing Removed

—

Sep 13, 2016

Listed

$7,923,000

$503/sq ft

GMLS #97787

Sep 13, 2016

Listed

$7,923,000

$503/sq ft

Smart MLS #99055943

Aug 4, 2014

Listing Removed

—

Mar 5, 2014

Listed

$8,950,000

$568/sq ft

Smart MLS #98540532

Nov 1, 2012

Listing Removed

—

May 24, 2012

Listed

$950,000

$60/sq ft

Smart MLS #98505539

Sep 4, 2012

Listing Removed

—

Jun 20, 2011

Listed

$10,923,000

$694/sq ft

Public Records

Oct 14, 2005

Sold

$3,200,000

$203/sq ft

Public Records

Feb 16, 1952

Sold

$78,500

$5/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$63,249 (+3.1%)

$742,210 + $2,597,210

$3,339,420

2022

$61,345 (+1.2%)

$742,210 + $2,597,210

$3,339,420

2021

$60,644

$742,210 + $2,597,210

$3,339,420

2020

$60,644 (−0.4%)

$742,210 + $2,597,210

$3,339,420

2019

$60,911 (−34.0%)

$742,210 + $2,597,210

$3,339,420

2018

$92,277 (+1.7%)

$763,420 + $4,677,470

$5,440,890

2017

$90,700 (+2.2%)

$763,420 + $4,677,470

$5,440,890

2016

$88,741 (+5.0%)

$763,420 + $4,677,470

$5,440,890

2014

$84,551

$763,420 + $4,677,470

$5,440,890

Tax history for 153 Chichester Rd

Year

Property tax

Land + Additions

Assessment*

2023

$63,249 (+3.1%)

$742,210 + $2,597,210

$3,339,420

2022

$61,345 (+1.2%)

$742,210 + $2,597,210

$3,339,420

2021

$60,644

$742,210 + $2,597,210

$3,339,420

2020

$60,644 (−0.4%)

$742,210 + $2,597,210

$3,339,420

2019

$60,911 (−34.0%)

$742,210 + $2,597,210

$3,339,420

2018

$92,277 (+1.7%)

$763,420 + $4,677,470

$5,440,890

2017

$90,700 (+2.2%)

$763,420 + $4,677,470

$5,440,890

2016

$88,741 (+5.0%)

$763,420 + $4,677,470

$5,440,890

2014

$84,551

$763,420 + $4,677,470

$5,440,890

*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

4.6 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Fairfield County

APN

184298

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: 7

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 20
Laundry Room Location: 2nd Floor
Interior Features: Audio System, Auto Garage Door Opener, Cable - Available, Central Vacuum, Elevator, Security System
In-Law Apartment: Yes
In-Law Access: Lower Level
Fireplaces Total: 9
Cooling System: Central Air, Zoned
Appliances Included: Oven/Range, Counter Grill, Wall Oven, Microwave, Refrigerator, Icemaker, Dishwasher, Washer, Dryer

Bathroom Information
# of Baths (Full): 7
# of Baths (Half): 4

Bedroom Information
Beds Total: 6

Room Information
Rooms Additional: Bonus Room, Exercise Room, Foyer, Laundry Room, Mud Room, Sitting Room, Staff Quarters, Wine Cellar, Workshop
Room Count: 15
Basement Description: Full, Full With Walk-Out, Heated, Cooled, Interior Access, Walk-out
Has Attic
Attic Description: Walk-up

Exterior

Exterior Features
Roof Information: Wood Shingle
Exterior Siding: Shingle, Stone
Exterior Features: Balcony, French Doors, Grill, Gutters, Lighting, Stone Wall, Terrace, Underground Sprinkler, Underground Utilities

Lot Information
Lot Description: Dry, Lightly Wooded, Treed, Fence - Partial

Pool Information
Swimming Pool
Pool Description: Pool House, In Ground Pool, Spa, Infinity Edge, Heated, Salt Water, Gunite

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

Property Information
Property Type: Single Family For Sale
Driveway Type: Asphalt, Heated

Financial

Assessments Information
Assessed Value: $5,440,890

Utilities

Utility Information
Water Source: Public Water Connected
Sewage System: Septic
Hot Water Description: 100 Gallon Tank, Oil
Heat Type: Hydro Air, Radiant, Zoned
Heat Fuel Type: Oil
Fuel Tank Location: In Basement
Energy Features: Generator, Programmable Thermostat, Thermopane Windows

Location

School Information
Middle Jr High School: Saxe Middle
High School: New Canaan
Elementary School: West

Location Information
State: Connecticut
Directions: Merritt X36, left on 106, left on Weed St, left on Wahackme Rd, Right on Chichester Rd
County: Fairfield

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 4.6 acres
Style: Other
Year Built: —
Year Renovated: —
County: Fairfield County
APN: 184298

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 6

Around this home

Schools

West School

Public PreK-4 • Assigned • 0.9mi

10/10

Saxe Middle School

Public 5-8 • Assigned • 2.3mi

10/10

New Canaan High School

Public 9-12 • Assigned • 2.3mi

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

5/10 Heat Factor

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

6/10 Wind Factor

55% 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

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

$7.33M – $8.87M

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Home values near 153 Chichester Rd

Data from public records.

Address	Redfin Estimate
160 Chichester Road, New Canaan, CT - Beds \| - Baths \| - Sq. Ft.	$2,865,813
65 Chichester Road, New Canaan, CT 5 Beds \| 6 Baths \| 6311 Sq. Ft.	$4,085,495

Address	Redfin Estimate
177 Chichester Road, New Canaan, CT 4 Beds \| 4 Baths \| 3383 Sq. Ft.	$3,223,005
136 Chichester Road, New Canaan, CT 3 Beds \| 2.5 Baths \| 1416 Sq. Ft.	$2,534,779

Address	Redfin Estimate
188 Chichester Road, New Canaan, CT 3 Beds \| 3 Baths \| 2528 Sq. Ft.	$2,421,433
82 Chichester Road, New Canaan, CT 3 Beds \| 3 Baths \| 2731 Sq. Ft.	$1,971,689

Property information provided by Smart MLS when last listed in 2018. 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 153 Chichester Rd

Tax history for 153 Chichester 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 153 Chichester Rd

More real estate resources