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$3,000,000

  • Sold
  • Closed
  • Single Family
  • 4 Beds
  • 5 Full Baths
  • 1 Partial Bath
  • 3,961 Sq. Ft.
  • 3 Car Garage
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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

Full Property Details for 1380 Old Academy Rd

General

  • Sold For: $3,000,000
  • Taxes: (July 2025-June 2026)
  • Status: Closed
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24153510
  • Added to Site: 104 day(s) ago

Interior

  • Number of Rooms: 9
  • Rooms/Areas: Exercise Room, Foyer, Mud Room, Wine Cellar
  • Interior Features: Audio System, Auto Garage Door Opener, Security System
  • Fireplace: Yes
  • Number of Fireplaces: 3
  • Appliances: Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller

Rooms

Bathrooms

  • Total Bathrooms: 6
  • Full Bathrooms: 5
  • Half Bathrooms: 1
  • Partial Bath: Hardwood Floor, Main

Bedrooms

  • Total Bedrooms: 4
  • Primary Suite: Cathedral Ceiling, Bedroom Suite, Gas Log Fireplace, , Upper
  • Bedroom 1: Bedroom - Bedroom Suite, Full Bath, Walk-In Closet, Hardwood Floor, Upper
  • Bedroom 2: Bedroom - Jack & Jill Bath, Walk-In Closet, Hardwood Floor, Upper
  • Bedroom 3: Bedroom - Jack & Jill Bath, Walk-In Closet, Hardwood Floor, Upper

Other Rooms

  • Living Room: Living Room - Fireplace, Hardwood Floor, Main
  • Family Room: Family Room - Fireplace, Patio/Terrace, Hardwood Floor, Main
  • Eat In Kitchen: Eat-In Kitchen - Bay/Bow Window, Quartz Counters, Dining Area, Wet Bar, Island, , Main
  • Dining Room: Dining Room - Hardwood Floor, Main
  • Office: Office - Built-Ins, Patio/Terrace, Hardwood Floor, Main
  • Game room: Yes
  • Game Room: Rec/Play Room - Wall/Wall Carpet, Lower
  • Rec Room: Wall/Wall Carpet, Lower
  • Laundry: Upper Level

Additional Information

  • Pool: Yes
  • Pool Description: Gunite, Heated, Safety Fence, In Ground Pool

Exterior

  • Exterior Features: Patio

Parking

  • Garage: Yes
  • Attached garage: Yes
  • Garage Spaces: 3
  • Parking: Attached Garage

Location

  • County: Fairfield
  • Neighborhood: Greenfield Hill
  • Driving Directions: Bronson or Redding Road to Old Academy Rd.

School Information

  • Elementary School: Dwight
  • Middle School: Roger Ludlowe
  • High School: Fairfield Ludlowe

Community

  • Community Name: Greenfield Hill

Heating & Cooling

  • Cooling Type: Central Air
  • Heating Type: Hot Air, Oil
  • Heating Fuel: Oil
  • Water Heater: Oil, Upright Tank

Utilities

  • Sewer: Septic
  • Water: Public Water Connected

Structural Information

  • Architectural Style: Colonial
  • Construction Status: No/Resale
  • Exterior Const.: Clapboard
  • Basement Desc.: Full, Heated, Storage, Fully Finished, Cooled, Liveable Space
  • Roof: Asphalt Shingle
  • Attic: Yes
  • Square Feet: 3,961
  • Above Ground: 3,961 Sq. Ft.
  • Year Built: 2000

Lot Features

  • Lot Size (Acres): 1.91
  • Zoning: AAA
  • Lot Description: Level Lot, Professionally Landscaped

Water Features

  • Water Front Desc.: Beach Rights

Green Features

  • Energy Features: Generator

Financial Considerations

  • Assessment Amount: $1,095,850
  • Tax Year: July 2025-June 2026

Disclosures and Reports

  • Exclusions: Light fixture in the front entry way and light fixture over the kitchen table excluded, but negotiable.
  • Property ID: 133126

Meet the listing agent

Meet the listing agent
— 1380 Old Academy Rd —

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NMLS#: 1598647

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Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

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Schools serving 1380 Old Academy Rd

School District:Fairfield School District
NameGradesDistance
Dwight Elementary School
1600 Redding Road, Fairfield, CT 06824
PK-50.5 mi
Roger Ludlowe Middle School
689 Unquowa Road, Fairfield, CT 06824
6-82.7 mi
Fairfield Ludlowe High School
785 Unquowa Road, Fairfield, CT 06824
9-122.6 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1380 Old Academy Rd

Date
Details
Price
Change
Source
4/16/2026
Sold
$3,000,000
15.61%
MLS
2/25/2026
Listed
$2,595,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

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1380 Old Academy Road, Fairfield, CT 06824 (MLS# 24153510) is a Single Family property that was sold at $3,000,000 on April 16, 2026. This property was listed by Cindy Raney & Team from our Westport Office.Want to learn more about 1380 Old Academy Road? Do you have questions about finding other Single Family real estate for sale in Fairfield? You can browse all Fairfield real estate or contact a Coldwell Banker agent to request more information.