50 Brookbend Road, Fairfield, CT 06824
Property image
Property image
UNDER CONTRACT
1.78 ACRES

$2,050,000

  • 5 Beds
  • 4.5 Baths
  • 4,512 sqft (on 1.78 acres)

50 Brookbend Road, Fairfield, CT 06824

Est. Mortgage $13,928/mo*
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Home Highlights

Single-Family Home
Built in 1950
1.78 acre lot
$454/sqft
3 Car Garage

Local Information

  • Map ViewExplore the area around 50 Brookbend Road.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

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.
Last check for updates: about 17 hours ago
Listing courtesy of Kate Cacciatore, (917) 952-1195
William Raveis Real Estate, (917) 952-1195
Source: Smart MLS, MLS#24193848
Also Listed on Smart MLS.

Home Details for 50 Brookbend Road

Interior Features

Interior Details
Basement: Full,UnfinishedNumber of Rooms: 10Types of Rooms: Master Bedroom, Bedroom, Dining Room, Family Room, Great Room, Kitchen, Living Room
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 5Number of Bathrooms (full): 4Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 4512 Square Feet
Appliances & Utilities
Appliances: Cooktop, Oven, Refrigerator, Freezer, Dishwasher, Trash Compactor, Washer, Dryer, Gas Water Heater, Water HeaterDishwasherDryerLaundry: Main Level,Mud RoomRefrigeratorWasher
Heating & Cooling
Heating: Hot Water,Natural GasHas CoolingAir Conditioning: Central Air,Window Unit(s)Has HeatingHeating Fuel: Hot Water
Fireplace & Spa
Number of Fireplaces: 3Has a Fireplace
Windows, Doors, Floors & Walls
Door: French Doors

Exterior Features

Exterior Home Features
Roof: AsphaltPatio / Porch: PatioOther Structures: Shed(s)Exterior: Rain Gutters, Garden, Stone Wall, Underground SprinklerFoundation: Concrete PerimeterGardenNo Private Pool
Parking & Garage
Number of Garage Spaces: 3Number of Covered Spaces: 3No CarportHas a GarageHas an Attached GarageParking Spaces: 3Parking: Attached,Garage Door Opener
Frontage
Not on Waterfront
Water & Sewer
Sewer: Public Sewer
Finished Area
Finished Area (above surface): 4120 Square FeetFinished Area (below surface): 392 Square Feet

Days on Market

Days on Market: 55

Property Information

Year Built
Year Built: 1950
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family ResidenceArchitecture: Colonial
Building
Construction Materials: Shake Siding, CedarNot a New ConstructionDoes Not Include Home Warranty
Property Information
Parcel Number: 128573

Price & Status

Price
List Price: $2,050,000Price Per Sqft: $454
Status Change & Dates
Off Market Date: Wed Sep 02 2026Possession Timing: Neg

Active Status

MLS Status: Under Contract

Location

Direction & Address
City: FairfieldCommunity: Winton Park
School Information
Elementary School: RiverfieldJr High / Middle School: Roger LudloweHigh School: Fairfield Ludlowe

Agent Information

Listing Agent
Listing ID: 24193848

Building

Building Area
Building Area: 4512 Square Feet

Community

Community Features: Health Club, Library, Private School(s), Near Public Transport, Shopping/Mall

HOA

No HOA

Lot Information

Lot Area: 1.78 Acres

Miscellaneous

BasementMls Number: 24193848Zillow Contingency Status: Under ContractAttic: Pull Down StairsAttribution Contact: (917) 952-1195Above Grade Unfinished Area: 4120Activation Date: Sat Aug 08 2026

Additional Information

Health ClubLibraryPrivate School(s)Near Public TransportShopping/Mall

Around this home

What Locals Say about Fairfield

At least 343 Trulia users voted on each feature.

  • 91 % Say it's dog friendly

  • 87 % Say car is needed

  • 85 % Say parking is easy

  • 82 % Say yards are well-kept

  • 79 % Say there's holiday spirit

  • 76 % Say people would walk alone at night

  • 71 % Say kids play outside

  • 66 % Say they plan to stay for at least 5 years

  • 66 % Say it's quiet

  • 64 % Say there's wildlife

  • 61 % Say neighbors are friendly

  • 61 % Say there are sidewalks

  • 59 % Say streets are well-lit

  • 57 % Say it's walkable to restaurants

  • 50 % Say there are community events

  • 48 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • teddyabby
    "It’s safe and pretty and everyone looks out for one another. There is a bunch of cute parks and a nice walkable downtown."
    0
    Flag
  • Bnsdkbr225
    "Friendly and beautiful. Close to Lake Mohegan and parks. Lake rights to Lake Hill’s association . "
    0
    Flag
  • Kevin.cohen318
    "Great place to raise a family, incredibly safe and has all the amenities you could want on a year round basis."
    0
    Flag
  • Alexande.pappas
    "Yes walking miking kids walking to school we have public beaches lake’s plenty of restaurants churches"
    0
    Flag
  • Samuel Rivera
    "Great town for families with kids. Fairfield offers great schools, good supermarkets, tons of restaurants and entertainment "
    0
    Flag
  • Timothy Moss
    "Very family friendly. Great place to live for people of any age. I’ve lived here for 10 years now….."
    0
    Flag
  • Kevin.cohen318
    "5 minutes to either I-95, the Merritt Parkway or metro north, train to NYC is just over an hour each way. Great town that’s close to everything but not too close to anything."
    1
    Flag
  • Trulia User
    "My neighbor is safe and friendly and very clean as well. I've lived in this neighborhood over 18 years and absolutely love it. Thank you "
    3
    Flag
  • Trulia User
    "A very well maintained area . Homes streets ,business ,beaches schools ,library’s ( 3 ) . So much to offer !"
    0
    Flag
  • Sauerh
    "My neighborhood is family-oriented with distinct yet harmonious homes with well- kept yards. We are a short trip from Bridgeport, Norwalk, and Stamford with excellent connections via Metro North and I-95."
    5
    Flag
  • Isabellecj
    "Great neighborhood , good schools, close to town and railway station and beach . Very safe and quiet , properties well maintained and kids friendly . Love my neighborhood!"
    3
    Flag
  • Collin M.
    "Tons of events. Parties. Free concerts etc. there is so much fun things to do and see here. Beaches are amazing!"
    0
    Flag
  • Ab h
    "Walk to absolutely everything from hop on the train to yankee stadium or going to your dentist. Beautiful beaches and parks at your fingertips and children’s activities galore."
    0
    Flag
  • Juan G.
    "Quiet, clean and a good place to raise your kids. The school system it’s awesome and you know your kids are in good hands. "
    1
    Flag
  • Imeiers
    "We have neighbourhood block parties, the best trick or treating in town and a wonderful community spirit. Easily one of the best neighbourhoods in Fairfield. "
    5
    Flag
  • Troy P.
    "I work in Fairfield and it’s a wonderful town. The drive from New Haven is pretty easy with 2 route options either 95 or the merit parkway. "
    0
    Flag
  • Juan G.
    "Best in Connecticut, I have lived here for 6 years and my kids love it. If you want a place to raise your kids this it is the place "
    0
    Flag
  • Sar K.
    "Block parties, neighborhood watch, strong neighbor community, varying ages, active community, holiday celebrations: memorial parade, pancake breakfast, Christmas tree lighting, movies at the beach, music on the green, amazing local restaurants, 4th of July fireworks and much more"
    3
    Flag
  • DE
    "Very safe and relatively diverse. Great schools and decent restaurants. The beach is close by and some good golf courses."
    1
    Flag
  • Raquel.noi
    "Would love it, plenty of space for the dogs to run. Walking trails, beautiful neighborhoods to got for a walk. You will love it here!!"
    0
    Flag
  • Raquel
    "Great place, great community environment! It is such nice to go for walks and feel safe. We love that we found our home here!"
    0
    Flag
  • Raquel
    "Great family environment, lots of parks. Neighbors are friendly and welcoming. A lot of activities for kids. "
    0
    Flag
  • Lisalberts
    "It’s friendly and easy to walk or ride bikes around. The schools are wonderful. A real community feel."
    0
    Flag
  • Alek M.
    "Great town to raise a family, good schools and safe neighborhoods for your kids. Friendly people and clean area all around."
    1
    Flag
  • Fortress.management
    "Excellent schools, great town amenities makes it a great area to raise a family. Commuting to NYC is a little over an hour. Vibrant restaurant scene."
    0
    Flag
  • John S. W. J.
    "A great family oriented town. We love the parks the beaches and the community atmosphere. We couldn’t imagine living anywhere else"
    0
    Flag
  • Blythe A. B.
    "Driving to the train station is easy but parking passes are hard to come by unless you find street parking. waiting list is 18 months. "
    0
    Flag
  • Blythe A. B.
    "Everyone walks their dogs. sidewalks are well maintained. there are plenty of parks as well, both dog parks and free space parks. it is well kept by all dog owners, and it’s expected that you pick up after them!"
    0
    Flag
  • Bellaamore99
    "Close to parks, Wholefoods , Homedepo, shopping and metronorth train. Great neighbores . And feel very safe. "
    5
    Flag
  • Mjcejbart
    "Dog walking Mecca at lake Mohegan. All dogs welcome. Very dog friendly. Nice lake and trails to enjoy with or without a dog. "
    0
    Flag
  • Cheetah4455
    "Christmas walk around in Toilsome Hill. Meet the neighbors and everyone brings a different plate of food"
    1
    Flag
  • al .P
    "Lots of dogs on leaches . Not having your dog on a leach is not a good idea . You know your dog but the other does not know your dog "
    1
    Flag
  • Nour Y.
    "One dog can annoy a lot of families since homes are close to each other so multiple dogs barking is even worse"
    5
    Flag
  • Bassickrachel
    "I do see dogs frequently. People seem friendly, neighbors are quiet. I love airfield for the commute and small Town atmosphere."
    1
    Flag
  • Bassickrachel
    "Excellent I am 5 minutes from I-95 and Fairfield Metro Train Station. It is close to grocery stores and it is quite with friendly people."
    0
    Flag
  • Dennis
    "Many dogs that are very pleasant. Owners stop and chat while dogs play. Great way to meet your neighbors."
    0
    Flag
  • Larry
    "Moved here from Dallas and absolutely love it. I commute to downtown New Haven by car and it’s about 30-35 minutes."
    0
    Flag

Market trends in Fairfield

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$986K
$28.33KMoM
Sale-to-List Price
103.8%
0.2%MoM
Price per sq ft
$473
$1MoM
Available listings
129
33MoM

Home Value

Trulia Estimate
$2.04M
Since last month
Decreased$11K (-0.6%)
Since last year
Increased$161K (+8.6%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +41% in the last 10 years
MonthEstimated value
2026
September 2026$2.04M
August 2026$2.05M
July 2026$2.21M
June 2026$2.12M
May 2026$2.12M
April 2026$2.03M
March 2026$2.03M
February 2026$1.96M
January 2026$1.94M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
1123 Round Hill Road, Fairfield, CT
0.37
Single-Family Home
$2,850,000
09/16/26
5
5.5
5,014
610 Unquowa Road, Fairfield, CT
0.31
Single-Family Home
$1,658,000
05/06/26
4
3.5
2,786
1054 Mill Plain Road, Fairfield, CT
0.22
Single-Family Home
$2,300,000
09/03/26
5
4.5
7,318
570 Unquowa Road, Fairfield, CT
0.33
Single-Family Home
$1,975,000
05/21/26
4
4.5
4,520
1091 Round Hill Road, Fairfield, CT
0.35
Single-Family Home
$1,500,000
04/01/26
4
2.5
3,122
20 Saint Marc Lane, Fairfield, CT
0.36
Single-Family Home
$2,025,000
06/12/26
5
4.5
3,715
533 North Benson Road, Fairfield, CT
0.47
Single-Family Home
$1,350,000
08/03/26
6
4.5
3,631
20 Ermine Street, Fairfield, CT
0.38
Single-Family Home
$1,100,000
05/01/26
4
2
1,925
12 Sconset Drive, Fairfield, CT
0.38
Single-Family Home
$1,525,000
07/27/26
4
3.5
2,399
232 Pell Meadow Drive, Fairfield, CT
0.53
Single-Family Home
$1,947,000
01/12/26
4
3.5
4,378

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
761 Round Hill Road, Fairfield, CT 06824
0.09
$2,053,400
4
3.5
3,967
Off Market
230 Winton Road, Fairfield, CT 06430
0.14
$2,455,200
4
5
6,000
Off Market
327 Brookbend Road, Fairfield, CT 06824
0.16
$2,931,100
6
6.5
6,103
Off Market
361 Brookbend Road, Fairfield, CT 06430
0.18
$1,908,000
4
4
4,500
Off Market
584 Barlow Road, Fairfield, CT 06824
0.22
$2,112,600
4
3.5
3,008
Off Market
29 Taunton Road, Fairfield, CT 06430
0.21
$1,121,100
4
2.5
2,700
Off Market
158 Taunton Road, Fairfield, CT 06824
0.20
$875,700
3
1.5
1,836
Off Market
1054 Mill Plain Road, Fairfield, CT 06824
0.22
$2,300,000
5
4.5
7,318
Recently Sold
245 Taunton Road, Fairfield, CT 06824
0.21
$1,187,700
4
1.5
2,246
Off Market
886 Mill Plain Road, Fairfield, CT 06824
0.26
$915,300
3
2
1,416
Off Market
15 Phyfe Road, Fairfield, CT 06824
0.26
$1,165,200
4
2.5
2,744
Off Market
1110 Mill Plain Road, Fairfield, CT 06430
0.26
$794,600
3
1.5
1,544
Off Market

Price and Tax history

DateEventPrice
Sep 2, 2026
Source: Smart MLS #24193848
Pending
$2,050,000
Aug 20, 2026
Source: Smart MLS #24193848
PriceChange
$2,050,000
Price decreased by 7%
Aug 8, 2026
Source: Smart MLS #24193848
Listed For Sale
$2,195,000

LGBTQ Local Legal Protections

Kate Cacciatore, William Raveis Real Estate, (917) 952-1195
Agent Phone: (917) 952-1195
IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Information is deemed reliable but not guaranteed.

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Frequently asked questions about 50 Brookbend Road

  • What is the estimated monthly payment for 50 Brookbend Road?
    Based on a $2,050,000 list price with 20% down at today's rates, the estimated monthly payment for 50 Brookbend Road in Fairfield, CT is approximately $14,124 (about $11,162 principal & interest, $2,887 property taxes, and $75 homeowner's insurance). This is an estimate. Actual payment depends on your loan terms.
  • How does the list price for 50 Brookbend Road compare to homes in Fairfield?
    50 Brookbend Road in Fairfield, CT is listed at $2,050,000, about 108% above the $986K median sale price in Fairfield.
  • What do residents say about Fairfield?
    Residents describe Fairfield, CT as dog-friendly, easy to park in, and well-kept. Most residents say you need a car. See homes for sale in Fairfield, CT.
  • What are the closest schools to 50 Brookbend Road?
    The closest schools to 50 Brookbend Road in Fairfield, CT are Fairfield Ludlowe High School (rated 9/10), Riverfield School (Elementary, rated 7/10), Roger Ludlowe Middle School (rated 8/10).
  • Does 50 Brookbend Road have air conditioning?
    Yes, 50 Brookbend Road in Fairfield, CT has air conditioning.
  • Does 50 Brookbend Road have laundry facilities?
    Yes, 50 Brookbend Road in Fairfield, CT has in-unit laundry.
50 Brookbend Road, Fairfield, CT 06824 is a 5 bedroom, 5 bathroom, 4,512 sqft single-family home built in 1950. This property is currently available for sale and was listed by Smart MLS on Jul 29, 2026. The MLS # for this home is MLS# 24193848.