Fairfield, CT / 1 DAY ON MARKET

550 Wellington DriveFairfield, CT 06824

Asking price$1,925,000Active

Open house

  • Saturday, September 19, 202612:00 pm – 2:00 pm ET
  • Sunday, September 20, 20261:00 pm – 3:00 pm ET

Our Take

550 Wellington Drive sits at the end of a quiet Greenfield Hill cul-de-sac on 2.47 secluded acres. The home centers its daily life around a kitchen connected to multiple gathering spaces, including a living room, vaulted family room, playroom, sunroom and wood-paneled office. Four upstairs bedrooms separate sleeping areas from the main living spaces, with recently updated bathrooms. Outdoors, mature landscaping surrounds a pool, expansive deck and screened-in porch, with room for dining and entertaining. A three-car garage completes the property.

Estimated buyer rebate

Buy with Cress and Save $19,250 on brokerage fees*

When you buy with Cress, we give you back a portion of the brokerage commission we receive.

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*Estimate assumes a 2.5% buyer-agent commission and a 40% rebate. Actual savings depend on final purchase price and commission received.

At a glance

Active · MLS #24206227
Bedrooms
4
BathroomsBaths
3 full / 1 half
Square feet
4,779
Year built
1985
Acres
2.47
Property taxes
$27,664

July 2026-June 2027

What stands out

  • Greenfield Hill cul-de-sac setting
  • 2.47 secluded acres
  • Vaulted family room and sunroom
  • Wood-paneled office and oversized playroom
  • Kitchen at the heart of the home
  • Four upstairs bedrooms with updated bathrooms
  • Pool, expansive deck, and screened-in porch
  • Three-car garage
Read the full listing description

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.

Schools

Elementary
Dwight
Middle
Roger Ludlowe
High
Fairfield Ludlowe

Schools as reported by SmartMLS. Confirm attendance assignments with the district.

A closer look at the location

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550 Wellington Drive, Fairfield, CT 06824

Price history

DateEventPrice
Originally listed$1,925,000

Intermediate price changes and previous listings may not be included.

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*Estimate: $1,925,000 asking price × assumed 2.5% buyer-agent commission × 40% rebate = $19,250. Actual savings depend on the final purchase price and commission Cress receives. The assumed commission is not a representation of this listing's offered compensation.

Listed by Brown Harris Stevens · (203) 254-1500

Wendy Ryan

SmartMLS · Listing #24206227 · Active

Listing data checked: Sep 17, 2026, 7:04 PM EDT.

Listing information is deemed reliable but not guaranteed. Cress commentary is separate from the MLS listing description. Contact Cress about a correction.

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