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550 Wellington Drive

Fairfield, Connecticut 06824

COMING SOON - NEW$1,925,000
Beds
4
Baths
3 | 1
SqFt
4,779
Acres
2.47
Year Built
1985
Matt Caiola

Matt Caiola

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Pool3-Car Garage3 Fireplaces

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

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$12,946

per 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

Similar Properties

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

Listed By

Wendy Ryan

(203) 964-7450

Brown Harris Stevens

(203) 254-1500

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.