Recently Viewed Properties
See This Home
Save This Listing
Close

View All Photos

$2,595,000 Coming Soon

  • For Sale
  • Coming Soon
  • Single Family
  • 4 Beds
  • 5 Full Baths
  • 1 Partial Bath
  • 3,961 Sq. Ft.
  • 3 Car Garage
  • Updated 2 days ago
See This Home
Save This Home
See This Home
Save This Home
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

Full Property Details for 1380 Old Academy Rd

General

  • Price: $2,595,000
  • Taxes: (July 2025-June 2026)
  • Status: Coming Soon
  • Type: Single Family
  • Source: SMARTMLS
  • MLS ID: 24153510
  • Updated: 2/19/2026
  • Added to Site: 10 day(s) ago
  • Expected Market Date: 2/25/2026

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
Buyer's Brokerage Compensation: Contact Listing Agent
Not binding unless confirmed by separate agreement among applicable parties.

Quickly Find Out More

* Indicates a required field

Yes, I would like more information. Please use and/or share my information with a Coldwell Banker ® affiliated agent to contact me about my real estate needs. By clicking Send Message, I request to be contacted by phone or text message and consent to being contacted by automated means. I understand that my consent to receive calls or texts is not a condition of purchasing any property, goods, or services. Alternatively, I understand that I can access real estate services by email or I can contact the agent myself.

If an Coldwell Banker affiliated agent is not available in the area where I need assistance, I agree to be contacted by a real estate agent affiliated with another brand owned or licensed by Anywhere Real Estate (BHGRE®, CENTURY 21®, Corcoran®, ERA®, or Sotheby’s International Realty®). I acknowledge that I have read and agree to the Terms of Use and Privacy Notice.

We Value Your Privacy

Meet the listing agent

Meet the listing agent
— 1380 Old Academy Rd —

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

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 Pitney Bowes and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 1380 Old Academy Rd Get Price Alerts and Save Property

Date
Details
Price
Change
Source
2/11/2026
Listed
$2,595,000
10.38%
MLS
7/29/2005
Sold
$2,351,000
—
Public Record
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 1380 Old Academy Rd

Year
Property Taxes
Change
Tax Assessment
Change
2024
$31,111
2%
$1,095,850
—
2023
$30,574
1%
$1,095,850
—
2023
$30,147
1%
$1,095,850
—
2022
$29,851
1%
$1,095,850
—
2021
$29,566
-8%
$1,095,850
-8%
2020
$31,989
—
$1,194,060
—
2019
$31,989
2%
$1,194,060
—
2018
$31,475
2%
$1,194,060
—
2017
$30,831
1%
$1,194,060
—
2016
$30,389
-5%
$1,194,060
-7%
2015
$31,942
2%
$1,288,490
—
2014
$31,439
2%
$1,288,490
—
2011
$30,834
—
$1,288,490
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 1380 Old Academy Rd

$
Down Payment
%
$
%

$
$

*These costs are estimates, and the interest rates assume exceptional credit standing.

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Similar Properties near 1380 Old Academy Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

88 Merry Meet Cir, Fairfield, CT 06824 - Photo 1
$2,498,000
Open House

88 Merry Meet Cir  Fairfield, CT 06824

  • Single Family
  • Active
  • 5
    Beds
  • 8
    Total Baths
  • 8,136
    Sq. Ft.
Listed by The Agency
200 Long Mdw Rd, Fairfield, CT 06824 - Photo 1
$2,499,000

200 Long Mdw Rd  Fairfield, CT 06824

  • Single Family
  • Active
  • Updated 6 days ago
  • 4
    Beds
  • 3
    Total Baths
  • 5,015
    Sq. Ft.
Listed by Keller Williams Realty
2 Fairport Rd, Westport, CT 06880 - Photo 1
$2,600,000

2 Fairport Rd  Westport, CT 06880

  • Single Family
  • Active
  • 5
    Beds
  • 5
    Total Baths
  • 4,288
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
25 Old Rd, Westport, CT 06880 - Photo 1
$2,550,000

25 Old Rd  Westport, CT 06880

  • Single Family
  • Active
  • 5
    Beds
  • 5
    Total Baths
  • 6,330
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l

Just Listed near 1380 Old Academy Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

315 Seaside Ave, Bridgeport, CT 06605 - Photo 1 Just Listed
$499,900

315 Seaside Ave  Bridgeport, CT 06605

  • Single Family
  • Active
  • Updated 4 days ago
  • 2
    Beds
  • 1
    Total Bath
  • 955
    Sq. Ft.
Listed by Flamur Canaj (203) 452-3700
4699 Main St, Bridgeport, CT 06606 - Photo 1 Just Listed
$800

4699 Main St  #201 Room 1  Bridgeport, CT 06606

  • Commercial Lease
  • Active
Listed by YellowBrick Real Estate LLC
750 William St, Bridgeport, CT 06608 - Photo 1 Just Listed
$639,000

750 William St  Bridgeport, CT 06608

  • Multi-Family
  • Active
  • Updated 1 day ago
  • 7
    Total Beds
Listed by Eagle Eye Realty PLLC
700 Laurel Ave, Bridgeport, CT 06604 - Photo 1 Just Listed
$525,000

700 Laurel Ave  Bridgeport, CT 06604

  • Multi-Family
  • Active
  • Updated 5 days ago
  • 4
    Total Beds
Listed by Alpha Capital Realty, LLC

Price Reduced near 1380 Old Academy Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

186 Louisiana Ave, Bridgeport, CT 06610 - Photo 1 Price Reduced
-$5,000 (-3.57%)
$135,000

186 Louisiana Ave  #D  Bridgeport, CT 06610

  • Apartment
  • Active
  • Updated 2 days ago
  • 1
    Bed
  • 1
    Total Bath
  • 650
    Sq. Ft.
Listed by Kelly Durrschmidt (203) 878-7424
472 Huntington Turnpike, Bridgeport, CT 06610 - Photo 1 Price Reduced
-$70,000 (-15.73%)
$375,000

472 Huntington Turnpike  Bridgeport, CT 06610

  • Business
  • Active
Listed by NextHome Real Estate Services
31 Whittier St, Bridgeport, CT 06605 - Photo 1 Price Reduced
-$50,001 (-2.78%)
$1,749,999

31 Whittier St  Bridgeport, CT 06605

  • Multi-Family
  • Active
  • Updated 5 days ago
  • 16
    Total Beds
Listed by Alpha Capital Realty, LLC
208 Fairview Ave, Bridgeport, CT 06606 - Photo 1 Price Reduced
-$24,000 (-3.7%)
$625,000

208 Fairview Ave  Bridgeport, CT 06606

  • Multi-Family
  • Active
  • Updated 17 hours ago
  • 7
    Total Beds
Listed by ResComm Realty, LLC

Recent Sales near 1380 Old Academy Rd

This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.

21 Queens Grant Dr, Fairfield, CT 06824 - Photo 1 Sold
$2,880,000

21 Queens Grant Dr  Fairfield, CT 06824

  • Single Family
  • Closed
  • 6
    Beds
  • 8
    Total Baths
  • 14,110
    Sq. Ft.
Listed by William Raveis Real Estate
Sold by William Raveis Real Estate
2821 Congress St, Fairfield, CT 06824 - Photo 1 Sold
$2,700,000

2821 Congress St  Fairfield, CT 06824

  • Single Family
  • Closed
  • 5
    Beds
  • 5
    Total Baths
  • 3,703
    Sq. Ft.
Listed by Brown Harris Stevens
Sold by Serhant Connecticut, LLC
125 Brett Ln, Fairfield, CT 06824 - Photo 1 Sold
$2,337,000

125 Brett Ln  Fairfield, CT 06824

  • Single Family
  • Closed
  • 6
    Beds
  • 9
    Total Baths
  • 7,843
    Sq. Ft.
Listed by Linna Yuen and Bross Chingas Bross Team at Coldwell Banker Realty
Sold by Unrepresented Buyer
56 Charcoal Hill Rd, Westport, CT 06880 - Photo 1 Sold
$2,535,000

56 Charcoal Hill Rd  Westport, CT 06880

  • Single Family
  • Closed
  • 5
    Beds
  • 3
    Total Baths
  • 3,072
    Sq. Ft.
Listed by William Pitt Sotheby's Int'l
Sold by Bross Chingas Bross Team at Coldwell Banker Realty

1380 Old Academy Road, Fairfield, CT 06824 (MLS# 24153510) is a Single Family property with 4 bedrooms, 5 full bathrooms and 1 partial bathroom. 1380 Old Academy Road is currently listed for $2,595,000 and was received on February 11, 2026. This property is 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.

Tour this property