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50 Brookbend Road

Fairfield, Connecticut 06824

COMING SOON - NEW$2,195,000
Beds
5
Baths
4 | 1
SqFt
4,512
Acres
1.78
Year Built
1950
Matt Caiola

Matt Caiola

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3-Car Garage3 Fireplaces

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.

Key Facts

City/Town
Fairfield
Neighborhood
University
Property / Style
Single Family · Colonial
Year Built
1950
Days on Market
0 days
Beds
5
Baths
4 full · 1 half
Living Area
4,512 sq ft
Lot Size
1.78 acres
Garage / Parking
3 garage
Property Taxes
$22,250 / Annually

Market Snapshot

The Fairfield Market

Single Family · trailing 12 months

View area

Median Days on Market

34

88 active listings

Median $ / Sq Ft

$496

88 active listings

Sale-to-List Ratio

102.0%

570 sales

How this home compares

List Price

$2.19M

vs $1.60M median

37.3% above median

Price / Sq Ft

$486

vs $496 median

In line with median

Days on Market

0 days

vs 34 days median

34 days fresher than median

Based on 88 active and 570 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of July 29, 2026.

Location

50 Brookbend Road, Fairfield, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$13,778

per month

  • Principal & Interest$11,192
  • Property Taxes$1,854
  • Insurance$732
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Fairfield
Neighborhood
University
County
Fairfield
Subdivision
Winton Park

Residence

Property Type
Single Family
Style
Colonial
Year Built
1950
New Construction
No/Resale
Living Area
4,512 sq ft
Below Grade
392 sq ft

Schools

Elementary
Riverfield
High
Fairfield Ludlowe

Interior

Heating
Hot Water
Heat Fuel
Natural Gas
Cooling
Central AirWindow Unit
Fireplaces
3
Laundry
Main Level
Appliances
Cook TopWall OvenRefrigeratorFreezerDishwasherCompactorWasherDryer
Basement
FullUnfinished
In-Law Apartment
YesOver Garage
Interior Features
Auto Garage Door Opener
Additional Rooms
FoyerLaundry RoomMud Room

Exterior & Lot

Lot Size
1.78 acres
Zoning
AA
Garage / Parking
3 garage spacesAttached Garage
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Septic
Flood Zone
No
Construction
ShakeCedar
Roof
Asphalt Shingle
Foundation
Concrete
Exterior Features
ShedGuttersGarden AreaStone WallFrench DoorsUnderground SprinklerPatio
Lot Description
Level LotClearedProfessionally Landscaped

Listing & Financials

Property Taxes
$22,250 / Annually
Days on Market
0
MLS #
24193848
MLS Status
Coming Soon

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Kate Cacciatore

(917) 952-1195

William Raveis Real Estate

(203) 255-6841

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 7/29/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.

Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.

Data last updated on 7/29/2026 at 7:40 AM UTC.