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415 Old Post Road

Fairfield, Connecticut 06824

COMING SOON - NEW$3,975,000
Beds
5
Baths
4 | 1
SqFt
5,740
Acres
1.33
Year Built
1845
Matt Caiola

Matt Caiola

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3-Car Garage8 Fireplaces

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

City/Town
Fairfield
Neighborhood
Beach
Property / Style
Single Family · Antique
Year Built
1845
Days on Market
0 days
Beds
5
Baths
4 full · 1 half
Living Area
5,740 sq ft
Lot Size
1.33 acres
Garage / Parking
3 garage
Property Taxes
$47,267 / Annually

Market Snapshot

The Fairfield Market

Single Family · trailing 12 months

View area

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$25,911

per 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

City/Town
Fairfield
Neighborhood
Beach
County
Fairfield

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

Similar Properties

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Listed By

Cindy Raney

(203) 625-1820

Coldwell Banker Realty

(203) 227-8424

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.