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
Sold for $3,000,000
$3,000,000
1380 Old Academy Road, Fairfield, CT 06824
4beds
3,961sqft
Single Family Residence
Built in 2000
1.91 Acres Lot
$3,064,300 Zestimate®
$757/sqft
$7,707 Estimated rent
Home value
$3,064,300
$2.76M - $3.40M
$7,707/mo
Zestimate® history
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Zillow last checked:
Listing updated:
Listed by:
Cindy Raney & Team,
Cindy Raney (203)257-8320,
Coldwell Banker Realty 203-227-8424
Bought with:
Meredith Cohen, RES.0795887
Serhant Connecticut, LLC
Source: Smart MLS,MLS#: 24153510
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 6
- Full bathrooms: 5
- 1/2 bathrooms: 1
Rooms
- Room types: Exercise Room, Wine Cellar
Primary bedroom
- Features: Cathedral Ceiling(s), Bedroom Suite, Gas Log Fireplace, Full Bath, Walk-In Closet(s), Wall/Wall Carpet
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bedroom
- Features: Jack & Jill Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bedroom
- Features: Bedroom Suite, Full Bath, Walk-In Closet(s), Hardwood Floor
- Level: Upper
Bathroom
- Features: Hardwood Floor
- Level: Main
Bathroom
- Features: Full Bath, Tile Floor
- Level: Upper
Dining room
- Features: Hardwood Floor
- Level: Main
Family room
- Features: Fireplace, Patio/Terrace, Hardwood Floor
- Level: Main
Kitchen
- Features: Bay/Bow Window, Quartz Counters, Dining Area, Wet Bar, Kitchen Island, Patio/Terrace
- Level: Main
Living room
- Features: Fireplace, Hardwood Floor
- Level: Main
Office
- Features: Built-in Features, Patio/Terrace, Hardwood Floor
- Level: Main
Rec play room
- Features: Wall/Wall Carpet
- Level: Lower
Heating
- Forced Air, Oil
Cooling
- Central Air
Appliances
- Included: Oven, Range Hood, Refrigerator, Dishwasher, Washer, Dryer, Wine Cooler, Water Heater
- Laundry: Upper Level, Mud Room
Features
- Sound System, Entrance Foyer, Smart Thermostat, Wired for Sound
- Basement: Full,Heated,Storage Space,Finished,Cooled,Liveable Space
- Attic: Storage,Pull Down Stairs
- Number of fireplaces: 3
Interior area
- Total structure area: 3,961
- Total interior livable area: 3,961 sqft
- Finished area above ground: 3,961
Property
Parking
- Total spaces: 3
- Parking features: Attached, Garage Door Opener
- Attached garage spaces: 3
Features
- Patio & porch: Patio
- Has private pool: Yes
- Pool features: Gunite, Heated, Fenced, In Ground
- Waterfront features: Beach Access
Lot
- Size: 1.91 Acres
- Features: Level, Landscaped
Details
- Parcel number: 133126
- Zoning: AAA
- Other equipment: Generator
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Colonial
- Property subtype: Single Family Residence
Materials
- Clapboard
- Foundation: Concrete Perimeter
- Roof: Asphalt
Condition
- New construction: No
- Year built: 2000
Utilities & green energy
- Sewer: Septic Tank
- Water: Public
Community & HOA
Community
- Features: Park, Putting Green, Stables/Riding, Tennis Court(s)
- Security: Security System
- Subdivision: Greenfield Hill
HOA
- Has HOA: No
Location
- Region: Fairfield
Financial & listing details
- Price per square foot: $757/sqft
- Tax assessed value: $1,095,850
- Annual tax amount: $31,111
- Date on market: 2/11/2026
- Exclusions: Light fixture in the front entry way and light fixture over the kitchen table excluded, but negotiable.
Price history
| Date | Event | Price |
|---|---|---|
| 4/16/2026 | Sold | $3,000,000+15.6%$757/sqft |
Source:  Smart MLS #24153510 Report a problem | ||
| 3/6/2026 | Pending sale | $2,595,000$655/sqft |
Source: Smart MLS #24153510 Report a problem | ||
| 2/25/2026 | Listed for sale | $2,595,000+10.4%$655/sqft |
Source: Smart MLS #24153510 Report a problem | ||
| 7/29/2005 | Sold | $2,351,000+76.2%$594/sqft |
Source: Smart MLS #98234454 Report a problem | ||
| 6/26/2001 | Sold | $1,334,000$337/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | $31,111 +1.8% | $1,095,850 |
| 2024 | $30,574 +1.4% | $1,095,850 |
| 2023 | $30,147 +1% | $1,095,850 |
| 2022 | $29,851 +1% | $1,095,850 |
| 2021 | $29,566 -7.6% | $1,095,850 -8.2% |
| 2020 | $31,989 | $1,194,060 |
| 2019 | $31,989 +1.6% | $1,194,060 |
| 2018 | $31,475 +2.1% | $1,194,060 |
| 2017 | $30,831 -3.5% | $1,194,060 -7.3% |
| 2015 | $31,942 +1.6% | $1,288,490 |
| 2014 | $31,439 +2% | $1,288,490 |
| 2013 | $30,834 +6.5% | $1,288,490 |
| 2011 | $28,952 +13.5% | $1,288,490 -2.7% |
| 2010 | $25,508 +2% | $1,323,700 |
| 2009 | $25,018 +1.7% | $1,323,700 |
| 2008 | $24,594 +6.7% | $1,323,700 |
| 2007 | $23,046 +4.4% | $1,323,700 |
| 2006 | $22,066 +1.5% | $1,323,700 +51.1% |
| 2005 | $21,733 +10.4% | $876,330 +4.2% |
| 2004 | $19,682 +8.8% | $841,120 |
| 2003 | $18,084 +381.3% | $841,120 +553.8% |
| 2001 | $3,757 +85.3% | $128,660 |
| 2000 | $2,028 | $128,660 |
Find assessor info on the county website
Neighborhood: 06824
Nearby homes
- $1,913,1003 bd3 ba2.7k sqft1412 Old Academy Rd, Fairfield, CT 06824Off Market
- $2,066,5004 bd4 ba3.8k sqft1412B Old Academy Aka #1381, Fairfield, CT 04937Off Market
- $1,735,2003 bd2 ba4.1k sqft1296 Old Academy Rd, Fairfield, CT 06824Off Market
- $1,958,8004 bd3 ba3.5k sqft1381 Old Academy Rd, Fairfield, CT 06824Off Market
- $1,327,1003 bd2 ba2.1k sqft105 Dunham Rd, Fairfield, CT 06824Off Market
- $1,802,1004 bd4 ba3.8k sqft1313 Old Academy Rd, Fairfield, CT 06824Off Market
- $1,581,0005 bd3 ba2.4k sqft131 Dunham Rd, Fairfield, CT 06824Off Market
- $1,845,0004 bd5 ba3.7k sqft1009 Redding Rd, Fairfield, CT 06824Off Market
Nearby schools
GreatSchools rating
- 10/10Dwight Elementary SchoolGrades: K-5Distance: 0.6 mi
- 8/10Roger Ludlowe Middle SchoolGrades: 6-8Distance: 2.7 mi
- 9/10Fairfield Ludlowe High SchoolGrades: 9-12Distance: 2.6 mi
Schools provided by the listing agent
- Elementary: Dwight
- Middle: Roger Ludlowe
- High: Fairfield Ludlowe
Source: Smart MLS. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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- Connecticut
- Fairfield County
- Fairfield
- 06824
- 1380 Old Academy Road
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