About the Home
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
Rooms & Interior
Room Details
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Family Room (Main Level)
Fireplace, Patio/Terrace, Hardwood Floor
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Primary Br Suite (Upper Level)
Cathedral Ceiling, Bedroom Suite, Gas Log Fireplace, Full Bath, Walk-In Closet, Wall/Wall Carpet
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Bedroom (Upper Level)
Bedroom Suite, Full Bath, Walk-In Closet, Hardwood Floor
-
Rec/Play Room (Lower Level)
Wall/Wall Carpet
-
Office (Main Level)
Built-Ins, Patio/Terrace, Hardwood Floor
-
Bedroom (Upper Level)
Jack & Jill Bath, Walk-In Closet, Hardwood Floor
-
Dining Room (Main Level)
Hardwood Floor
-
Eat In Kitchen (Main Level)
Bay/Bow Window, Quartz Counters, Dining Area, Wet Bar, Island, Patio/Terrace
-
Half Bath (Main Level)
Hardwood Floor
-
Living Room (Main Level)
Fireplace, Hardwood Floor
-
Bedroom (Upper Level)
Jack & Jill Bath, Walk-In Closet, Hardwood Floor
-
Jack & Jill Bath (Upper Level)
Full Bath, Tile Floor
-
Primary Br Suite (Upper Level)
Cathedral Ceiling, Bedroom Suite, Gas Log Fireplace, Full Bath, Walk-In Closet, Wall/Wall Carpet
-
Bedroom (Upper Level)
Bedroom Suite, Full Bath, Walk-In Closet, Hardwood Floor
-
Rec/Play Room (Lower Level)
Wall/Wall Carpet
-
Family Room (Main Level)
Fireplace, Patio/Terrace, Hardwood Floor
-
Office (Main Level)
Built-Ins, Patio/Terrace, Hardwood Floor
-
Bedroom (Upper Level)
Jack & Jill Bath, Walk-In Closet, Hardwood Floor
-
Dining Room (Main Level)
Hardwood Floor
-
Eat In Kitchen (Main Level)
Bay/Bow Window, Quartz Counters, Dining Area, Wet Bar, Island, Patio/Terrace
-
Half Bath (Main Level)
Hardwood Floor
-
Living Room (Main Level)
Fireplace, Hardwood Floor
-
Bedroom (Upper Level)
Jack & Jill Bath, Walk-In Closet, Hardwood Floor
-
Jack & Jill Bath (Upper Level)
Full Bath, Tile Floor
-
Other Rooms
Exercise room, Foyer, Mud room, Wine cellar
Home Features
Heating
- Fireplaces: 3
- Heating: hot air
- Heat fuel type: oil
- Fuel tank: in basement
Interior Features
- Audio system
- Auto garage door opener
- Security system
Appliances
- Wall oven
- Range hood
- Refrigerator
- Dishwasher
- Washer
- Dryer
- Wine chiller
Home Automation
- Security system
- Thermostat(s)
- Wired for audio
Attic
- Storage space
- Pull-down stairs
Basement
- Full
- Heated
- Storage
- Fully finished
- Cooled
- Liveable space
Property Details
Parking
- Garage spaces: 3
- Attached garage
Swimming Pool
- Gunite
- Heated
- Safety fence
- In ground pool
Lot Details
- Lot surface: 1.91 acres
- Level lot
- Professionally landscaped
Utilities
- Water: public water connected
- Sewage: septic
Near-by Amenities
- Park
- Putting green
- Stables/riding
- Tennis courts
Construction Details
- Style
- colonial
- Construction year
- 2000
- Exterior Siding
- clapboard
- Foundation
- concrete
- Roof
- asphalt shingle
Area & Town
This home is located in Greenfield Hills neighborhood, in the town of Fairfield.
- $1.60M med. price
- 14 homes for sale
- $970K med. price
- 107 homes for sale
Finance & Listing Info
| Status |
Under contract |
| Listing date |
February 11, 2026 |
| List price |
$ 2,595,000 |
| Current price |
$ 2,595,000 |
| Tax amount |
$ 31,111 |
| Tax year |
july 2025-june 2026 |
| MLS ID |
#24153510 |
| List Agent |
Cindy Raney |
| List Office |
Coldwell Banker Realty |
(c) 2026 Based on information provided to and compiled by the Smart MLS, Inc.
