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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. NOT LOCATED IN A FLOOD ZONE.

Highlights

  • Residential
  • Single Family Residence
  • Built in 1845
  • 1.33 Acre Lot
  • 3 Car Garage
  • 57 days on Market

  • Bedrooms
    5
  • Bathrooms
    4 full · 1 half
  • Year Built
    1845
  • Architectural Style
    Antique
  • Construction Materials
    Frame, Clapboard
  • Foundation
    Concrete Perimeter
  • Garage Spaces
    3.0
  • Living Area
    5740.0
  • Interior Features
    Entrance Foyer
  • Appliances
    Dishwasher, Refrigerator, Freezer, Range Hood
  • Cooling
    Central Air
  • Heating
    Natural Gas, Hot Water
  • Basement
    Full, Unfinished

  • Acres
    1.33
  • Lot Features
    Level
  • Water
    Public

  • County
    Fairfield
  • City
    Fairfield
  • Zip Code
    06824
  • High School
    Fairfield Ludlowe
  • Middle School
    Roger Ludlowe
  • Elementary School
    Roger Sherman

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Frequently Asked Questions

How do I schedule a tour of 415 Post Rd?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 415 Post Rd.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 415 Post Rd?

Click Ask a Question to talk with our team. You already know it is a 5 bed, 4 bath, listed for $3,975,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Fairfield, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 415 Post Rd?

With a 20% down payment and a 30-year fixed loan at an illustrative 6.75% rate, the ez Mortgage Calculator estimates the monthly payment for 415 Post Rd at around $25,492. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 415 Post Rd?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Fairfield County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 415 Post Rd?

In most cases, yes. Whether 415 Post Rd is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Fairfield's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 415 Post Rd?

We can handle that for you. Our preferred local agent specializes in residentials in Fairfield and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

What is the price per square foot for this home?

This home is listed at $3,975,000 with 5,740 sqft of space—that comes out to approximately $693 per square foot.

How long has this property been on the market?

415 Post Rd was listed on September 12, 2026, which means it's been on the market for 57 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1845, making it approximately 181 years old.

What is the lot size of this property?

415 Post Rd sits on a 1.33-acre lot, which is 57,935 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Roger Sherman
  • Middle: Roger Ludlowe
  • High: Fairfield Ludlowe

Want to see how these schools compare? Check out our Fairfield County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 415 Post Rd?

The most recent public record shows annual property taxes for 415 Post Rd were approximately $47,267. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 415 Post Rd still available for sale?

Yes, this home is still available! Click the ♥ to favorite it so you don't miss any changes—or ask our local expert to schedule a time to see it in person.

Source: ez Home Search, MLS Data

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Listing information provided exclusively 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. Information deemed reliable but not guaranteed by the MLS. Copyright 2026, SmartMLS. All rights reserved.

Last Updated: November 08, 2026 at 02:55AM | Source: SmartMLS | MLS#: 24206348