1380 Old Academy Road, Fairfield, CT 06824

• 4 beds |
• 6 baths |
• 3,961 sqft

Property Description

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

Listing Status:

Active

Date Added:

February 11, 2026

Data Last Updated:

February 28, 2026 at 4:53PM

Listing Office:

Coldwell Banker Realty : (203) 227-8424

Listing Agent:

Cindy Raney : (203) 257-8320

MLS ID:

24153510

Interior

• General: Audio SystemAuto Garage Door OpenerSecurity System
• Rooms: Exercise RoomFoyerMud RoomWine Cellar
• Appliances: Wall OvenRange HoodRefrigeratorDishwasherWasherDryerWine Chiller
• Laundry: Upper Level
• Basement: FullHeatedStorageFully FinishedCooledLiveable Space
• A/C: Central Air
• Heating: Hot AirOil
• Fireplace: Fireplaces: 3

Exterior

• General: Patio
• Style: Colonial
• Pool: GuniteHeatedSafety FenceIn Ground Pool

Construction

• Roofing: Asphalt Shingle

Location

• County: Fairfield

Lot

• Zoning: AAA133126

Utilities

• Water: Public Water Connected
• Sewer: Septic

Financial

• Exclusions: Light fixture in the front entry way and light fixture over the kitchen table excludedbut negotiable.