415 Old Post Road
Fairfield, Connecticut 06824
- Beds
- 5
- Baths
- 4 | 1
- SqFt
- 5,740
- Acres
- 1.33
- Year Built
- 1845
- Neighborhood
- Beach
- Property Type
- Single Family

Matt Caiola
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Over an acre to yourself. The best of Fairfield within reach. In the heart of downtown Fairfield and the beach area, 415 Old Post Road offers something almost impossible to find: land and privacy to create a generational estate, with the life of a coastal town just beyond your gate. Only a handful of properties in the Sherman School district offer this. Fewer still could tell this story. The family who built this Italianate Victorian stayed for more than a century. Stand beneath its soaring ceilings, admire the craftsmanship, then step onto the screened-in porch. You begin to understand. Trees surround you. Church bells carry through the air. It feels like your own park. Yet the beach, schools, restaurants, shops and train are all within walking distance. For the current owners, that has meant children walking home from school with friends. Thanksgiving dinners for twenty. Additional bedroom options for overnight guests. Winter evenings around the parlor fire. A front porch filled with friends as the Memorial Day parade passes by. There is room here for the life you have imagined. Explore the possibilities for a pool, tennis court and gardens. Create a place where everyone gathers now-and where the next generation will want to return. Historic architecture. Meticulously maintained, thoughtfully updated and in pristine condition. A once-in-a-lifetime opportunity. Come discover what makes this place so hard to leave-and imagine what the next 50 years could look like.
Key Facts
Market Snapshot
The Fairfield Market
Single Family · trailing 12 months
Active Listings
95
65 under contract
Median List Price
$1.40M
95 active listings
Median Closed Price
$1.15M
583 sales
Median Days on Market
43
95 active listings
Median $ / Sq Ft
$483
95 active listings
Sale-to-List Ratio
102.3%
583 sales
How this home compares
List Price
$3.98M
vs $1.40M median
2.8× the median
Price / Sq Ft
$693
vs $483 median
43.5% above median
Days on Market
0 days
vs 43 days median
43 days fresher than median
Based on 95 active and 583 closed sales (trailing 12 mo) of single family in Fairfield. Source: SmartMLS · As of September 12, 2026.
Location
415 Old Post Road, Fairfield, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 10, 2026per month
- Principal & Interest$20,647
- Property Taxes$3,939
- Insurance$1,325
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
Residence
- Property Type
- Single Family
- Style
- Antique
- Year Built
- 1845
- New Construction
- No/Resale
- Living Area
- 5,740 sq ft
Schools
- Elementary
- Roger Sherman
- High
- Fairfield Ludlowe
Interior
- Heating
- Hot Water
- Heat Fuel
- Natural Gas
- Cooling
- Central AirSplit System
- Fireplaces
- 8
- Laundry Location
- First and second floor laundry
- Appliances
- Range HoodRefrigeratorFreezerDishwasher
- Basement
- FullUnfinished
- In-Law Apartment
- PossibleSecond FloorUpper Level
- Additional Rooms
- Bonus RoomExercise RoomFoyerLaundry Room
Exterior & Lot
- Lot Size
- 1.33 acres
- Zoning
- R3
- Garage / Parking
- 3 garage spacesDetached Garage
- Waterfront Details
- Water Community
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Flood Zone
- No
- Construction
- Clapboard
- Color
- Cream
- Roof
- Asphalt Shingle
- Foundation
- Concrete
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $47,267 / Annually
- Days on Market
- 0
- MLS #
- 24206348
- MLS Status
- Coming Soon
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This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/12/2026. This information is provided for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing or leasing. Data is deemed reliable but is not guaranteed accurate by the MLS, the listing broker, the listing agent, or Matt Caiola. Buyers and tenants should independently verify all information that matters to their decision.
Map locations may be approximate. Any offer of compensation, if applicable, is made only to participants of the MLS where the listing is filed. ©2026 Smart MLS, Inc. All rights reserved.
Data last updated on 9/12/2026 at 8:05 PM UTC.