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
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
1380 Old Academy Road
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1380 Old Academy Road
1380 Old Academy Road
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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
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1380 Old Academy Road
Sold

1380 Old Academy Road

1380 Old Academy Road, Fairfield, Connecticut 06824

$3,000,000
THANK YOU FOR YOUR STRONG INTEREST; SELLER REQUESTS HIGHEST & BEST OFFERS BY 4PM SAT 2/28 . 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 livi

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
  • Laundry room Upper Level
  • APPLIANCES Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
  • other interior Features Audio System, Auto Garage Door Opener, Security System

Area & Lot

  • Status Sold
  • Date Sold April 16, 2026
  • Living Area3,961 Sq.Ft.
  • Lot Area1.91 Acres
  • MLS® ID24153510
  • TypeOther
  • YEAR BUILT2000
  • NeighborhoodFairfield
  • Architecture StylesColonial
  • Water FrontageBeach Rights
  • Elementary SchoolDwight
  • Middle SchoolRoger Ludlowe
  • High SchoolFairfield Ludlowe

Exterior

  • Garage Space3.0
  • water SourcePublic Water Connected
  • PoolGunite, Heated, Safety Fence, In Ground Pool
  • roofAsphalt Shingle
  • lot featuresLevel Lot, Professionally Landscaped
  • parkingAttached Garage
  • HEAT TYPEHot Air
  • AIR CONDITIONINGCentral Air
  • sewerSeptic
  • SubstructureConcrete
  • other exterior FeaturesPatio

Financial

  • Sales Price$3,000,000
  • 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 an elite boutique real estate team in Fairfield County with extensive industry expertise, having sold over $800 million in luxury real estate. Cindy’s team is deeply focused on the client experience, guiding clients through every step of the home buying or selling process to ensure an exceptional experience from start to finish.

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