50 Brookbend Road
Fairfield, Connecticut 06824
Reduced from $2,195,000
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 4,512
- Acres
- 1.78
- Year Built
- 1950
- Neighborhood
- University
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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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
- 47 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
- $27,349 / Annually
Market Snapshot
The Fairfield Market
Single Family · trailing 12 months
Active Listings
98
66 under contract
Median List Price
$1.40M
98 active listings
Median Closed Price
$1.15M
583 sales
Median Days on Market
43
98 active listings
Median $ / Sq Ft
$483
98 active listings
Sale-to-List Ratio
102.3%
583 sales
How this home compares
List Price
$2.05M
vs $1.40M median
46.7% above median
Price / Sq Ft
$454
vs $483 median
6.0% below median
Days on Market
47 days
vs 43 days median
4 days longer than median
Based on 98 active and 583 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of September 14, 2026.
Location
50 Brookbend Road, Fairfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$10,648
- Property Taxes$2,279
- Insurance$683
- 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
- Public Sewer Connected
- 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
- $27,349 / Annually
- Days on Market
- 47
- MLS #
- 24193848
- MLS Status
- Under Contract
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/14/2026. 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 9/14/2026 at 11:35 PM UTC.