550 Wellington Drive
Fairfield, Connecticut 06824
- Beds
- 4
- Baths
- 3 | 1
- SqFt
- 4,779
- Acres
- 2.47
- Year Built
- 1985
- Neighborhood
- Greenfield Hill
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Tucked at the end of a quiet Greenfield Hill cul-de-sac, 550 Wellington Drive feels like a true retreat-private, peaceful and designed for the way you actually want to live. Set on 2.47 secluded acres, this 4-bed, 4,776sqft home offers an exceptional amount of space to gather, entertain and spread out, with a floor plan that gives everyone a place of their own. The 1st floor is especially expansive, with a gracious living room, dramatic vaulted family room, oversized playroom, sunroom and sophisticated wood-paneled office-spaces that easily adapt for entertaining, working from home, play or simply finding a quiet corner to unwind. The kitchen sits at the heart of the home, creating an easy connection between everyday living and the many gathering spaces. Upstairs, four bedrooms provide a comfortable separation from the main living areas, complemented by recently updated bathrooms. Outside is where 550 Wellington truly becomes an escape. Surrounded by mature landscaping and complete privacy, the backyard resembles a private resort with pool, expansive deck, screened-in porch and abundant space for outdoor dining, entertaining and long summer days at home. A three-car garage completes the offering. Spacious yet inviting, private yet close to everything Greenfield Hill has to offer, 550 Wellington Drive is a homemade for gathering, entertaining and getting away-without ever having to leave home.
Key Facts
- City/Town
- Fairfield
- Neighborhood
- Greenfield Hill
- Property / Style
- Single Family · Colonial
- Year Built
- 1985
- Days on Market
- 1 day
- Beds
- 4
- Baths
- 3 full · 1 half
- Living Area
- 4,779 sq ft
- Lot Size
- 2.47 acres
- Garage / Parking
- 3 garage
- Property Taxes
- $27,664 / Annually
Market Snapshot
The Fairfield Market
Single Family · trailing 12 months
Active Listings
95
65 under contract
Median List Price
$1.40M
95 active listings
Median Closed Price
$1.15M
588 sales
Median Days on Market
42
95 active listings
Median $ / Sq Ft
$483
95 active listings
Sale-to-List Ratio
102.3%
588 sales
How this home compares
List Price
$1.93M
vs $1.40M median
37.6% above median
Price / Sq Ft
$403
vs $483 median
16.6% below median
Days on Market
1 day
vs 42 days median
41 days fresher than median
Based on 95 active and 588 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of September 12, 2026.
Location
550 Wellington Drive, Fairfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$9,999
- Property Taxes$2,305
- Insurance$642
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Fairfield
- Neighborhood
- Greenfield Hill
- County
- Fairfield
Residence
- Property Type
- Single Family
- Style
- Colonial
- Year Built
- 1985
- New Construction
- No/Resale
- Living Area
- 4,779 sq ft
Schools
- Elementary
- Dwight
- High
- Fairfield Ludlowe
Interior
- Heating
- Hot Air
- Heat Fuel
- Oil
- Cooling
- Attic FanCentral AirZoned
- Fireplaces
- 3
- Laundry
- Main Level
- Laundry Location
- Main Level
- Appliances
- Electric CooktopWall OvenMicrowaveRefrigeratorDishwasherWasherDryer
- Basement
- FullUnfinishedStorageInterior AccessConcrete Floor
- In-Law Apartment
- YesFirst FloorSeparate Entry
- Interior Features
- Auto Garage Door OpenerCable - Pre-wired
- Additional Rooms
- FoyerLaundry Room
Exterior & Lot
- Lot Size
- 2.47 acres
- Zoning
- AAA
- Garage / Parking
- 3 garage spacesDetached Garage
- Waterfront Details
- Beach Rights
- Water Source
- Public Water Connected
- Sewer
- Septic
- Flood Zone
- No
- Pool
- VinylIn Ground Pool
- Construction
- ShakeClapboard
- Color
- Gray
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Exterior Features
- PorchWrap Around DeckGuttersFrench DoorsPatio
- Lot Description
- Fence - FullLightly WoodedDryLevel LotOn Cul-De-SacProfessionally Landscaped
Listing & Financials
- Property Taxes
- $27,664 / Annually
- Days on Market
- 1
- MLS #
- 24206227
- MLS Status
- Coming Soon
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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 9/12/2026. 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 9/12/2026 at 12:20 AM UTC.