1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
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1380 Old Academy Road
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1380 Old Academy Road
1380 Old Academy Road
1380 Old Academy Road
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1380 Old Academy Road
1380 Old Academy Road
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1380 Old Academy Road
Coming Soon

1380 Old Academy Road

1380 Old Academy Road, Fairfield, CT 06824

$2,595,000
One approaches 1380 Old Academy Road through a stone wall, where a paved drive opens to a gravel courtyard arrival framed by mature trees and open skies. Old Academy is the kind of street where homes feel settled rather than transitional, and where people arrive, put down roots, and tend to stay. Inside, the house is generous without feeling oversized. Tall ceilings, dormers, and bay windows draw natural light deep into the living spaces, allowing it to move easily throughout the day. The main living areas are grounded by multiple fireplaces, and the layout supports everyday living with ease while expanding naturally when the house is full. The finished lower level adds meaningful flexibility, with room for fitness, media, or wine storage. A cabana-style mudroom with a full bath and direct outdoor access extends the way the home lives across seasons. Upstairs, the bedrooms are designed with privacy in mind, offering thoughtful connections that work well for both family and guests. Outdoors, the property becomes a destination in its own right. A Gunite pool bordered by stone terraces, an outdoor fireplace, a putting green, and a side porch with rocking chairs create spaces meant for lingering rather than passing through. Manicured grounds, full irrigation, and a three-car garage complete the setting. Carefully maintained and continually improved, this is Greenfield Hill living that feels grounded and enduring. A home that continues to work season to season, year after year

4
beds

6
baths

3,961 Sq.Ft. LIVING AREA

1.91 Acres lot

Cindy Raney

Cindy Raney

Features & Amenities

Interior

  • total bedrooms4
  • Total bathrooms6
  • full bathrooms5
  • half bathroom1
  • APPLIANCES Dishwasher, Dryer, Refrigerator, Oven, Washer, Range Hood, Wine Cooler
  • other interior Features Sound System, Entrance Foyer

Area & Lot

  • Status Coming Soon
  • Living Area3,961 Sq.Ft.
  • Total Area3,961 Sq.Ft.
  • Lot Area1.91 Acres
  • MLS® ID24153510
  • TypeResidential
  • YEAR BUILT2000
  • NeighborhoodFairfield
  • Architecture StylesColonial
  • Water FrontageBeach Access
  • Elementary SchoolDwight
  • Middle SchoolRoger Ludlowe
  • High SchoolFairfield Ludlowe

Exterior

  • Garage Space3.0
  • water SourcePublic
  • PoolGunite, Heated, Outdoor Pool, In Ground
  • roofAsphalt
  • lot featuresLevel
  • parkingGarage Door Opener, Attached
  • HEAT TYPEOil, Forced Air
  • AIR CONDITIONINGCentral Air
  • sewerSeptic Tank
  • SubstructureConcrete Perimeter
  • security FeaturesSecurity System

Financial

  • Sales Price$2,595,000
  • Buyer Agency Compensation 2%
  • Real Estate Tax $31,111/yr
  • Zoning AAA

Fairfield

Fairfield, Connecticut is an affluent town located on the shoreline of the Long Island Sound.

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Work With Us

Cindy Raney & Team is the elite, boutique real estate team in Fairfield County. They are extremely well versed in the industry, having sold over half a billion dollars in luxury real estate. Cindy’s team is particularly focused on the client experience, helping them throughout the home buying or selling process to ensure that their experience with the team is exceptional.

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