Off Market Feb 2023 for $2.3M

$3,867,372

Est. refi paymentEst. refi $10,965/mo

•

5,046

sq ft

587 Brookside Rd, New Canaan, CT 06840

About this home

Welcome to the most beautiful antique farmhouse in New Canaan! This is the combination dreams are made of - the charm and style that only comes with an antique, but the modern updating which today's buyers require. The first floor includes a formal dining room, family room, expansive living room, bar room, and a cook's dream eat-in kitchen. Each of these rooms opens into the next, creating a fantastic circular flow; an exceptional layout for relaxing and entertaining! Walls of windows and beautiful French doors throughout the first level showcase the lush property, make for sun drenched rooms, and offer access to a large front deck and expansive back patio. 3 fireplaces and original details blend seamlessly with the stylish living spaces. The primary suite has an expansive bedroom area, luxe en suite bath, large walk in closet, and an oversized sunroom/reading room/ office space. The ultimate private bedroom suite! The four additional bedrooms are charm-filled with updated full bathrooms. The lower level includes a large, second family room with custom built-in and walk out to the expansive garden filled property. The 1.3 acre property includes lush landscaping that offers incredible privacy, a beautiful heated pool, and the most delightful guest cottage and greenhouse! Come tour a one of a kind home, minutes from downtown New Canaan!

Single-familyProperty Type

1890Year Built

1.33 acresLot Size

$766Est. Price/Sq.Ft.

2 car garageParking

Listed by Rita Kirby • William Pitt Sotheby's Int'l

Listed by Annaliese Kirby • William Pitt Sotheby's Int'l

Bought with Mary Higgins • Brown Harris Stevens

Source:Smart MLS #170542765

Redfin Estimate

$3,867,372

$1.5M since sold in February 2023$21K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 19.6% higher than the average sale price ($3.23M) of 6 comparable homes.

SOLD JUL 21, 2026
$3,300,000
A
4 beds4.5 baths5,185 sq ft
19 Richards Ln, New Canaan, CT 06840
SOLD JUN 18, 2026
$2,000,000
B
5 beds4.5 baths6,132 sq ft
201 Ponus AVE EXT, Norwalk, CT 06854
SOLD DEC 23, 2025
$3,100,000
C
5 beds3.5 baths4,689 sq ft
339 Old Norwalk Rd, New Canaan, CT 06840
SOLD JUN 9, 2026
$3,400,000
D
4 beds4.5 baths4,980 sq ft
35 Danvers Ln, New Canaan, CT 06840
SOLD DEC 19, 2025
$3,100,000
E
5 beds4.5 baths4,880 sq ft
52 Putnam Rd, New Canaan, CT 06840
SOLD AUG 3, 2026
$4,500,000
F
5 beds3.5 baths4,379 sq ft
20 Buttonwood Ln, Darien, CT 06820

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Earn from this home

Sell

$1,903,300

Est. take-home

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Refinance

Est. cash available

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Market trends in 06840, CT

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

107.7%

+1.4% MoM

Median sale price

$2.4M

$373K MoM

Avg. days on market

19d

0 days MoM

Recently sold homes

7 MoM

New listings for sale

NEW 13 HRS AGO
$1,250,000
5 beds2 baths1,936 sq ft
16 Raymond St, New Canaan, CT 06840
COMING SOON
$2,295,000
3 beds2.5 baths2,406 sq ft
197 Park St #197, New Canaan, CT 06840
COMING SOON
$2,495,000
4 beds3.5 baths3,170 sq ft
39 Bank St #8, New Canaan, CT 06840
$355,000
1 bed1 bath758 sq ft
196 Park St #8, New Canaan, CT 06840
COMING SOON
$1,399,000
3 beds2.5 baths1,655 sq ft
179 South Ave #9, New Canaan, CT 06840
COMING SOON
$2,349,000
4 beds3.5 baths3,836 sq ft
6 Down River Rd #2, New Canaan, CT 06840
$4,595,000
6 beds6.5 baths6,246 sq ft
125 West Rd, New Canaan, CT 06840
$1,999,000
4 beds3 baths4,183 sq ft
Gravel Island Rd, New Canaan, CT 06840
COMING SOON
$3,495,000
3 beds4 baths4,407 sq ft
700 N Wilton Rd, New Canaan, CT 06840
See all

Provided by Redfin

Sale history for 587 Brookside Rd

Date

Event

Price

Smart MLS #170542765

Feb 23, 2023

Sold

$2,329,000

$462/sq ft

Jan 25, 2023

Pending

—

Jan 11, 2023

Listed

$2,349,000

$466/sq ft

Smart MLS #170320288

Feb 16, 2021

Sold

$2,175,000

$431/sq ft

Nov 3, 2020

Contingent

—

Jul 27, 2020

Listed

$2,195,000

$435/sq ft

Vintage yet modern farmhouse reimagined for the 21st century. This iconic & treasured custom-built one-of-a-kind New Canaan home has an open concept first-floor-plan & stylish sun-drenched rooms that afford casual living for today's lifestyle. New design elements in this fully renovated home were chosen for their timeless appeal. The chef's kitchen incorporates the original brick fireplace w/ modern amenities & the charming pub room is complete w/ wine fridge & sink. Many areas throughout the house & guesthouse offer quiet places to work or relax while looking out on lush outdoor gardens. The guesthouse has a first-floor apartment w/ a private entrance, a second level bonus room & office, 2-car garage & greenhouse. W/ hundreds of feet of quintessential Connecticut stone walls, heated pool & a flat & dry playing field, this home will appeal to all. Built w/ the quality, solidity & integrity of a c.1890 home that was formerly within the borders of Darien is as special as it is unique. Enjoy a prime location that is equidistant to the Darien & New Canaan town centers, the main Metro-North train line & is within minutes to the New Canaan Y, 300-acre Waveny Park, South Elementary School, Saxe Middle School, & the New Canaan High School. Community beaches are within 15 minutes! Work from home in style, with privacy, calm & serenity.

2018-2019: Exterior painted, some interior rooms painted, new well pump, new microwave, new Miele dishwasher, new hot water heater, septic updated. Main house is oil heat. LL finished room is electric heat (one room). Carriage house has propane heat and central air. ALL rooms are air-conditioned except LL finished room. Inclusions: Basement freezer, pub room wine fridge, attached lighting. Exclusions: Powder room mirror, rugs, invisible fence collar, attached TVs, washer & dryer, all personal property. Disclosures: Miele espresso machine is as-is. Irregular floor pattern in DR & one BR. Antique wood-burning stove in the guest apartment is ornamental only. Iron gates at end of driveway are ornamental only. All measurements to be verified by buyer. Screens where seen. Agent owned.

Smart MLS #170232771

Jun 23, 2020

Listing Removed

—

Nov 4, 2019

Price Changed

$2,195,000

$435/sq ft

Sep 5, 2019

Listed

$2,250,000

$446/sq ft

Smart MLS #170078445

Jul 7, 2019

Listing Removed

—

Feb 4, 2019

Price Changed

$2,250,000

$446/sq ft

Oct 31, 2018

Relisted

—

Aug 3, 2018

Listing Removed

—

May 3, 2018

Listed

$2,395,000

$475/sq ft

Smart MLS #170004535

Apr 10, 2018

Listing Removed

—

Sep 6, 2017

Listed

$2,475,000

$490/sq ft

Smart MLS #99163812

Jul 17, 2017

Listing Removed

—

Oct 17, 2016

Listed

$2,495,000

$494/sq ft

Smart MLS #99135529

Jul 17, 2016

Listing Removed

—

Mar 2, 2016

Listed

$2,695,000

$534/sq ft

Smart MLS #97031072

Nov 7, 1997

Listed

$995,000

$197/sq ft

Public Records

Jul 11, 1978

Sold

$225,000

$45/sq ft

Year

Property tax

Land + Additions

Assessment*

2023

$23,639 (+3.1%)

$576,100 + $672,000

$1,248,100

2022

$22,928 (+1.2%)

$576,100 + $672,000

$1,248,100

2021

$22,665

$576,100 + $672,000

$1,248,100

2020

$22,665 (−0.4%)

$576,100 + $672,000

$1,248,100

2019

$22,765 (+0.6%)

$576,100 + $672,000

$1,248,100

2018

$22,628 (+1.7%)

$502,110 + $832,090

$1,334,200

2017

$22,241 (+2.2%)

$502,110 + $832,090

$1,334,200

2016

$21,761 (+5.0%)

$502,110 + $832,090

$1,334,200

2014

$20,733

$502,110 + $832,090

$1,334,200

Tax history for 587 Brookside Rd

Year

Property tax

Land + Additions

Assessment*

2023

$23,639 (+3.1%)

$576,100 + $672,000

$1,248,100

2022

$22,928 (+1.2%)

$576,100 + $672,000

$1,248,100

2021

$22,665

$576,100 + $672,000

$1,248,100

2020

$22,665 (−0.4%)

$576,100 + $672,000

$1,248,100

2019

$22,765 (+0.6%)

$576,100 + $672,000

$1,248,100

2018

$22,628 (+1.7%)

$502,110 + $832,090

$1,334,200

2017

$22,241 (+2.2%)

$502,110 + $832,090

$1,334,200

2016

$21,761 (+5.0%)

$502,110 + $832,090

$1,334,200

2014

$20,733

$502,110 + $832,090

$1,334,200

*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

1.33 Acres

Year renovated

—

Sq. Ft.

—

Year built

—

Style

Other

County

Fairfield County

APN

185774

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 13, 2023.

Property details

Parking

Garage Information
Garage & Parking: Detached Garage
Garages Number: 2

Interior

Virtual Tour Information
Has Virtual Tour

Interior Information
Total Rooms: 12
Laundry Room Location: Full Laundry Room in Basement
Laundry Room Info: Lower Level
Interior Features: Audio System, Auto Garage Door Opener, Cable - Pre-wired, Open Floor Plan, Security System
In-Law Apartment: Yes
In-Law Access: First Floor
Thermostat(s)
Fireplaces Total: 3
Cooling System: Central Air, Zoned
Appliances Included: Gas Cooktop, Oven/Range, Microwave, Range Hood, Refrigerator, Freezer, Subzero, Dishwasher, Disposal, Wine Chiller

Bathroom Information
# of Baths (Full): 4
# of Baths (Half): 2

Bedroom Information
Beds Total: 5

Room Information
Rooms Additional: Bonus Room, Exercise Room, Foyer, Greenhouse, Laundry Room, Mud Room, Sitting Room, Staff Quarters
Room Count: 15
Basement Description: Full With Walk-Out, Partially Finished, Heated, Interior Access, Walk-out, Storage
Has Attic
Attic Description: Walk-up, Finished, Storage Space

Exterior

Exterior Features
Roof Information: Asphalt Shingle
Exterior Siding: Shingle
Exterior Features: Awnings, Garden Area, Guest House, Gutters, Lighting, Patio, Porch, Stone Wall, Underground Sprinkler

Lot Information
Lot Description: Dry, Level Lot, Fence - Full, Fence - Stone, Fence - Wood, Professionally Landscaped

Pool Information
Swimming Pool
Pool Description: In Ground Pool, Heated, Safety Fence

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

Property Information
Property Type: Single Family For Sale
Driveway Type: Private, Circular

Financial

Assessments Information
Assessed Value: $1,248,100

Utilities

Utility Information
Water Source: Private Well
Sewage System: Septic
Hot Water Description: Oil
Heat Type: Hot Air, Radiator, Zoned
Heat Fuel Type: Oil, Propane
Fuel Tank Location: In Basement
Energy Features: Extra Insulation, Generator, Programmable Thermostat, Storm Windows, Thermopane Windows

Location

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

Location Information
State: Connecticut
Nearby Amenities: Golf Course, Library, Paddle Tennis, Park, Playground/Tot Lot, Public Pool, Stables/Riding, Tennis Courts
Directions: North on Brookside Road to last house on the left.
County: Fairfield

Public facts

Beds: —
Baths: —
Sq. Ft.: —
Stories: —
Lot Size: 1.33 acres
Style: Other
Year Built: —
Year Renovated: —
County: Fairfield County
APN: 185774

Home facts updated by county records on Jul 13, 2023

Other

Documents & Disclosures
Supplement Count Public: 3

Around this home

Schools

Saxe Middle School

Public 5-8 • Assigned • 1.0mi

10/10

New Canaan High School

Public 9-12 • Assigned • 1.0mi

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

69% chance of strong winds in next 30 years

4/10 Air Factor

4 unhealthy days expected this year, 6 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

$3.68M – $4.45M

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COMING SOON

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Home values near 587 Brookside Rd

Data from public records.

Address	Redfin Estimate
519 Brookside Road, New Canaan, CT 4 Beds \| 2.5 Baths \| 2677 Sq. Ft.	$2,144,576
521 Brookside Road, New Canaan, CT 5 Beds \| 3.5 Baths \| 3146 Sq. Ft.	$3,005,582

Address	Redfin Estimate
569 Brookside Road, New Canaan, CT 4 Beds \| 5 Baths \| 5883 Sq. Ft.	$3,778,715
545 Brookside Road, New Canaan, CT 4 Beds \| 3 Baths \| 3283 Sq. Ft.	$2,525,990

Address	Redfin Estimate
550 Brookside Road, New Canaan, CT 6 Beds \| 7 Baths \| 7031 Sq. Ft.	$4,319,447
523 Brookside Road, New Canaan, CT 5 Beds \| 3.5 Baths \| 2986 Sq. Ft.	$2,475,881

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 587 Brookside Rd

Tax history for 587 Brookside 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 587 Brookside Rd

More real estate resources