1380 Old Academy Rd

Fairfield, CT 06824

$2,595,000
Price
4
Beds
3,961 Sq. Ft.
$655 / Sq. Ft.
3,961
Sq. Ft.
$655
per Sq. Ft.
Coming Soon
Coming Soon

Description

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...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
  1. Listed by Cindy Raney • Coldwell Banker Realty
    P: (203)-257-8320 C: (203)-257-8320 cindy@cindyraney.com

Property Details for 1380 Old Academy Road

Basement Description
Full, Heated, Storage, Fully Finished, Cooled, Liveable Space
Direct Waterfront
No
Expected Active Date
02-25-2026
Garages Number
3
Neighborhood
Greenfield Hill
Style
Colonial
Garage Parking Info
Attached Garage
Swimming Pool
Yes
LISTING UPDATED: 02/11/2026 08:35 PM

Property Details for 1380 Old Academy Road

StatusComing Soon
MLS #24153510
Days on Market-
Taxes$31,111 / year
HOA Fees-
Condo/Co-op Fees-
Compass TypeSingle Family
MLS TypeResidential
Year Built2000
Lot Size1.91 AC / 83,199 SF
CountyFairfield County

Location

Listing Courtesy of Coldwell Banker Realty, Cindy Raney
Add your commute

Building Information for 1380 Old Academy Road

Stories-Year Built2000Building Size-Lot Size1.91 AC / 83,199 SF

Payment Calculator

$15,240 per month

30 year fixed, 6.15% Interest

Principal and Interest

$12,648

Property Taxes

$2,593

HOA Dues

$0

The Payment Calculator is for illustrative purposes only.

Property Information for 1380 Old Academy Road

Summary
Property and Location
  • Acres Source: Public Records
  • Directions: Bronson or Redding Road to Old Academy Rd.
  • Elementary School: Dwight
  • Flood Zone: No
  • High School: Fairfield Ludlowe
  • Latitude: 41.17536
  • Longitude: -73.299215
  • Middle Jr High School: Roger Ludlowe
  • Neighborhood Amenities: Park, Putting Green, Stables/Riding, Tennis Courts
  • State: Connecticut
HOA and Fees
  • Home Owner's Assocation: No
  • Tax Year: July 2025-June 2026
  • Property Tax: $31,111
Interior and Exterior Features
Exterior Features
  • Exterior Features: Patio
  • Pool Description: Gunite, Heated, Safety Fence, In Ground Pool
  • Waterfront Description: Beach Rights
Interior Features
  • Appliances Included: Wall Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Chiller
  • Attic Description: Storage Space, Pull-Down Stairs
  • Cooling System: Central Air
  • Heat Type: Hot Air
  • Attic YN: Yes
  • Fireplaces Total: 3
  • Home Automation: Security System, Thermostat(s), Wired For Audio
  • Interior Features: Audio System, Auto Garage Door Opener, Security System
  • Laundry Room Info: Upper Level
  • Rooms Additional: Exercise Room, Foyer, Mud Room, Wine Cellar
  • Rooms Total: 9
Room 1
  • Room Entry Order: 1
  • Room Features: Fireplace,Hardwood Floor
  • Room Level: Main
  • Room Type: Living Room
Room 2
  • Room Entry Order: 10
  • Room Features: Jack & Jill Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 3
  • Room Entry Order: 11
  • Room Features: Bedroom Suite,Full Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 4
  • Room Entry Order: 12
  • Room Features: Wall/Wall Carpet
  • Room Level: Lower
  • Room Type: Rec/Play Room
Room 5
  • Listing Key: 4A6F29011A3D25E0E0631A01100A2515
  • Room Entry Order: 2
  • Room Features: Built-Ins,Patio/Terrace,Hardwood Floor
  • Room Level: Main
  • Room Type: Office
Room 6
  • Room Entry Order: 3
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Dining Room
Room 7
  • Room Entry Order: 4
  • Room Features: Bay/Bow Window,Quartz Counters,Dining Area,Wet Bar,Island,Patio/Terrace
  • Room Level: Main
  • Room Type: Eat-In Kitchen
Room 8
  • Room Entry Order: 5
  • Room Features: Fireplace,Patio/Terrace,Hardwood Floor
  • Room Level: Main
  • Room Type: Family Room
Room 9
  • Listing Key: 4A6F29011A3D25E0E0631A01100A2515
  • Room Entry Order: 6
  • Room Features: Hardwood Floor
  • Room Level: Main
  • Room Type: Half Bath
Room 10
  • Room Entry Order: 7
  • Room Features: Cathedral Ceiling,Bedroom Suite,Gas Log Fireplace,Full Bath,Walk-In Closet,Wall/Wall Carpet
  • Room Level: Upper
  • Room Type: Primary BR Suite
Room 11
  • Room Entry Order: 8
  • Room Features: Jack & Jill Bath,Walk-In Closet,Hardwood Floor
  • Room Level: Upper
  • Room Type: Bedroom
Room 12
  • Room Entry Order: 9
  • Room Features: Full Bath,Tile Floor
  • Room Level: Upper
  • Room Type: Jack & Jill Bath
Property
Property and Assessments
  • Construction Description: Frame
  • Exclusions: Light fixture in the front entry way and light fixture over the kitchen table excluded, but negotiable.
  • Exterior Siding: Clapboard
  • Foundation Type: Concrete
  • Fuel Tank Location: In Basement
  • New Construction Type: No/Resale
  • Roof: Asphalt Shingle
  • Year Built: 2000
  • Year Built Source: Public Records
  • Bank Owned Property: No
  • Living Area SQFT Per Public Records: 3961
Lot Information
  • Lot Description: Level Lot, Professionally Landscaped
  • Parcel Number: 133126
  • Sq Ft Est Heated Above Grade: 3961.0
  • Sq Ft Total: 3961.0
  • Zoning: AAA
Utilities
  • Energy Features: Generator
  • Heat Fuel Type: Oil
  • Hot Water Description: Oil, Upright Tank
  • Sewage System: Septic
  • Water Source: Public Water Connected
Multi Family
Income and Expenses
  • Occupied By: Owner

Property History for 1380 Old Academy Road

DateEvent & SourcePriceAppreciation
Oct 3, 2008

Closed (Public Record)

Public Record #327037753

$1—
Oct 3, 2008

Closed (Public Record)

Public Record #327037754

$1

-99.0% / yr

Jul 29, 2005

Closed (Public Record)

Public Record #164911217

$2,351,000

+14.9% / yr

Jun 26, 2001

Closed (Public Record)

Public Record #90997632

$1,334,000

+154.1% / yr

Feb 15, 2000

Closed (Public Record)

Public Record #90994119

$375,000—
DateEvent & SourcePrice
10/03/2008

Closed (Public Record)

Public Record #327037753

$1
10/03/2008

Closed (Public Record)

Public Record #327037754

$1

-99.0% / yr

07/29/2005

Closed (Public Record)

Public Record #164911217

$2,351,000

+14.9% / yr

06/26/2001

Closed (Public Record)

Public Record #90997632

$1,334,000

+154.1% / yr

02/15/2000

Closed (Public Record)

Public Record #90994119

$375,000

For completeness, Compass often displays two records for one sale: the MLS record and the public record.

Public Records for 1380 Old Academy Road

Taxable ValueLand$354,130Additions$741,720Total$1,095,850
Tax Record2024$31,111 ($2,593 / month)
Home Facts
Beds4Baths5.5Total Finished SqFt3,961 SqFtAbove Grade Finished SqFt3,961 SqFtUnfinished Basement SqFt731 SqFtStories2Lot Size83,264 SqFtStyleSingle Family ResidenceYear Built2000ZoningAAACountyFAIRFIELDAPNFFLD M:221 B:10

Schools near 1380 Old Academy Road

This home is within Fairfield School District.
Rating
School
Type
Grades
Distance
Dwight Elementary School
Public - K to 5
Roger Ludlowe Middle School
Public - 6 to 8
Fairfield Ludlowe High School
Public - 9 to 12
Fairfield Country Day School
Private - K to 9
Rating
School
Distance
Dwight Elementary School
PublicK to 5

Roger Ludlowe Middle School
Public6 to 8

Fairfield Ludlowe High School
Public9 to 12

Fairfield Country Day School
PrivateK to 9

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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More information about 1380 Old Academy Road, Fairfield, CT 06824

1380 Old Academy Road is a single family home Coming Soon in Fairfield, CT 06824. This property is currently priced at $2,595,000. This listing's school district is Fairfield School District. Nearby schools include Dwight Elementary School, Roger Ludlowe Middle School and Fairfield Ludlowe High School. 1380 Old Academy Road is a 4-bed, 6-bath, 3,961 sqft single family home built in 2000.

No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass makes no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.

Listing Courtesy of Coldwell Banker Realty, Cindy Raney

Based on information from one of the following Multiple Listing Services: Darien MLS, Smart MLS and Greenwich Multiple Listing Service. Information being provided is for the visitor’s personal, noncommercial use and may not be used for any purpose other than to identify prospective properties visitor may be interested in purchasing. The data contained herein is copyrighted by Darien MLS, Smart MLS and Greenwich Multiple Listing Service is protected by all applicable copyright laws. Any dissemination of this information is in violation of copyright laws and is strictly prohibited. Property information referenced on this web site comes from the Internet Data Exchange (IDX) program of the MLS. This web site may reference real estate listing(s) held by a brokerage firm other than the broker and/or agent who owns this web site. For the avoidance of doubt, the accuracy of all information, regardless of source, is deemed reliable but not guaranteed and should be personally verified through personal inspection by and/or with the appropriate professionals.