Pending

$2,050,000

Est. $14,116/mo —

•

4,512

sq ft

50 Brookbend Rd, Fairfield, CT 06824

About this home

An extraordinarily rare opportunity in Fairfield's coveted Winton Park Association. Offered for the first time in over 4 decades, this timeless 5-bedroom, 4.5-bath Colonial is set on nearly 2 breathtaking, park-like acres, offering estate-like privacy w/an unparalleled walk-to-town lifestyle. A gracious foyer welcomes you inside, where a magnificent staircase, wide-plank hardwood floors & exquisite millwork define the home's enduring character. Oversized windows & beautifully scaled rooms reflect craftsmanship rarely found today. The step-down living room showcases elegant paneling, custom built-ins & a wood-burning fireplace, while the formal dining room opens through French doors to a private patio for effortless indoor/outdoor entertaining. The spacious eat-in kitchen overlooks spectacular grounds & opens to a sun-filled family room w/custom built-ins, 2nd fireplace & French doors to an enchanting brick patio w/tranquil waterfall. Upstairs offers 4 spacious bedrooms & 3 full baths including a gracious primary suite w/abundant closet space & ensuite bath. Private guest suite w/separate entrance, vaulted ceilings, fireplace, 5th bedroom & full bath. Expansive, level grounds offer endless possibilities for a pool, pool house, ADU or future expansion in a setting rarely found just moments from downtown, Metro-North, award-winning schools & beaches. Complete w/natural gas, public sewer, irrigation & attached 3-car garage. A legacy property ready for its next chapter.

Single-familyProperty Type

1950Year Built

1.78 acresLot Size

$454Price/Sq.Ft.

3 car garageParking

Listed by Kate Cacciatore • William Raveis Real Estate

Contact: Agent Attribution Contact: (917) 952-1195 | Office Attribution Contact: (203) 255-6841

Source:Smart MLS #24193848

Payment calculator

$14,116 per month

Principal and interest$11,188

Property taxes

$2,279

HOA dues

Home insurance

$649

Utilities

Add

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Affordability tools

Open houses

No upcoming open houses.

Nearby open houses (10)

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15 Geraldine Cir, Trumbull, CT 06611
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49 Wiebe Ave, Stratford, CT 06614
5,662 sq ft lot • Built 1951
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5 Harvann Rd, Norwalk, CT 06850
8,712 sq ft lot • Built 1964
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3 beds2 baths2,148 sq ft
45 Marie Dr, Stratford, CT 06614
0.23 acre lot • 2 garage spots • Built 1966
OPEN SUN, 12PM TO 2PM3D WALKTHROUGH
$700,000
2 beds2 baths1,285 sq ft
33 N Water St #703, Norwalk, CT 06854
$731 HOA • Parking • Built 2007
OPEN SUN, 12PM TO 2PM3D WALKTHROUGH
$925,000
2 beds2 baths1,600 sq ft
39 Whitney Gln #39, Westport, CT 06880
$280 HOA • Parking • Pool
OPEN SUN, 12PM TO 3PM
$715,000
4 beds2.5 baths2,248 sq ft
44 Geraldine Cir, Trumbull, CT 06611
0.56 acre lot • 2 garage spots • Built 1955
OPEN SUN, 1PM TO 3PM
$349,000
3 beds2 baths1,444 sq ft
1 Linden St Unit A10, Norwalk, CT 06851
$460 HOA • Parking • Pool
OPEN SUN, 1PM TO 3PM
$3,395,000
5 beds6.5 baths4,854 sq ft
12 Bauer Pl, Westport, CT 06880
0.27 acre lot • 2 garage spots • Built 2025
OPEN SUN, 2PM TO 4PM
$995,000
4 beds2.5 baths3,351 sq ft
195 Wood House Rd, Fairfield, CT 06824
2.27 acre lot • 2 garage spots • Built 1993

Around this home

Schools

K - 12
Preschool & daycare

Riverfield School

Public K-5 • Assigned • 0.7mi

10/10

Roger Ludlowe Middle School

Public 6-8 • Assigned • 0.4mi

9/10

Fairfield Ludlowe High School

Public 9-12 • Assigned • 0.3mi

8/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Market insights

50 Brookbend Rd · $2,050,000

DAYS ON MARKET

The average home goes pending in 43 days.

SALE-TO-LIST

Most homes are selling 2% above list price.

LIST PRICE

Median sale price in this area is $803,339. (61% lower than this home)

PRICE DROP

17% of homes in this area have had a price drop in the past month.

Property details

Interior
Exterior
Finance

Kitchen

Bathroom

Bedroom

Living

Dining

Interior features
Auto garage door opener
In-law apartment located over the garage
Foyer
Mud room
Full, unfinished basement
Attic with pull-down stairs
Three fireplaces
Central air and window-unit cooling

Bedrooms
5 bedrooms

Bathrooms
4 full bathrooms
1 half bathroom

Kitchen
Cooktop
Wall oven
Refrigerator
Freezer
Dishwasher
Compactor

Laundry & utility
Washer
Dryer
Laundry room on the main level

Sale and tax history for 50 Brookbend Rd

Sale History
Tax History

Year

Property tax

Land + Additions

Assessment*

2023

$21,560 (+1.0%)

$459,480 + $324,240

$783,720

2022

$21,349 (+1.0%)

$459,480 + $324,240

$783,720

2021

$21,145 (−14.3%)

$459,480 + $324,240

$783,720

2020

$24,660

$535,500 + $385,000

$920,500

2019

$24,660 (+1.6%)

$535,500 + $385,000

$920,500

2018

$24,264 (+2.1%)

$535,500 + $385,000

$920,500

2017

$23,767 (+1.5%)

$535,500 + $385,000

$920,500

2016

$23,427 (+0.4%)

$535,500 + $385,000

$920,500

2014

$23,336

$562,310 + $394,100

$956,410

Public record

Beds

Baths

4.5

Stories

Lot width

—

Lot depth

—

Lot size

1.78 Acres

Year renovated

—

Finished Sq. Ft.

4,120

Unfinished Sq. Ft.

—

Total Sq. Ft.

4,120

Year built

1950

Style

Single Family Residential

County

Fairfield County

APN

128573

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jun 13, 2023.

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

6 days above 97° expected this year, 13 days in 30 years

6/10 Wind Factor

67% 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

Fairfield, CT • 06824

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

94/ 100

Exceptional sunlight

Sunscore

This home ranks in the top 12% for direct sun exposure in Fairfield. There appears to be minimal shading by surrounding buildings, terrain, and vegetation.

9.2 hrs

5.4 hrs

JuneDecember

Provided by Shadowmap

Redfin Estimate for 50 Brookbend Rd

$1,982,834

$67K under list price of $2.05M

Nearby comparable homes

The Redfin Estimate uses 6 recent nearby sales, priced between $1.5M to $2.9M.

SOLD SEP 16, 2026
$2,850,000 Last sold price
5 beds5.5 baths5,014 sq ft
1123 Round Hill Rd, Fairfield, CT 06824
$114/sq ft
smaller lot
21 years older
SOLD AUG 21, 2026
$2,320,000 Last sold price
4 beds4.5 baths3,978 sq ft
298 S Benson Rd, Fairfield, CT 06824
$129/sq ft
smaller lot
64 years newer
SOLD AUG 17, 2026
$1,850,000 Last sold price
4 beds3.5 baths2,962 sq ft
200 Henry St, Fairfield, CT 06824
$171/sq ft
smaller lot
76 years newer
SOLD JUN 15, 2026
$1,499,000 Last sold price
5 beds3.5 baths3,229 sq ft
164 Wakeman Rd, Fairfield, CT 06824
$10/sq ft
smaller lot
20 years older
SOLD OCT 16, 2026
$2,100,000 Last sold price
5 beds3.5 baths2,732 sq ft
239 Beach Rd, Fairfield, CT 06824
$315/sq ft
smaller lot
50 years older
SOLD MAY 21, 2026
$1,975,000 Last sold price
4 beds4.5 baths4,520 sq ft
570 Unquowa Rd, Fairfield, CT 06824
$17/sq ft
smaller lot
62 years newer

Rental earnings

Est. $10,935 per month, based on comparable rentals

This home is pending

The seller has accepted an offer, and this property is now .

Have questions?

Jared Randall

Fairfield Redfin Agent

Jared Randall typically replies in about 7 minutes

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Details provided by Smart MLS and may not match the public record. Learn more.

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GreatSchools Ratings provided by GreatSchools.org.

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About this home

Payment calculator

Affordability tools

Open houses

Nearby open houses (10)

Around this home

Schools

Lifestyle

Market insights

Property details

Sale and tax history for 50 Brookbend Rd

Public record

Climate risks

Historical weather

Sun exposure

Redfin Estimate for 50 Brookbend Rd

This home is pending

Have questions?

Nearby similar homes

New listings for sale in 06824

More real estate resources