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227 E Main St , Middletown, CT 06457

$600,000

9
beds
3 full · 3 half
baths
3,180
sqft
1991
year built

Exceptional Mixed Use 3-Unit Investment Opportunity in Middletown! Well-maintained three-unit property offering the feel of townhouse-style living with the income potential of a multifamily investment. Each spacious unit features 3 bedrooms, 1 full bath, 1 half bath, an eat-in kitchen, abundant natural light, basement storage, and washer/dryer hookups. A standout feature is the private under-building garage for each unit with direct access, plus ample off-street parking and a rear driveway. Separate utilities provide added convenience for ownership and management. Ideally located near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. An excellent opportunity for an investor or owner-occupant looking to generate rental income while building equity. Property being Sold As Is. Agent/Owner related.

  • Bedrooms
    9
  • Bathrooms
    3 full · 3 half
  • Year Built
    1991
  • Architectural Style
    Units are Side-by-Side
  • Construction Materials
    Vinyl Siding, Concrete
  • Foundation
    Concrete Perimeter
  • Garage Spaces
    3.0
  • Parking Features
    Driveway, Paved, Off Street
  • Living Area
    3180.0
  • Cooling
    Window Unit(s)
  • Heating
    Baseboard, Electric
  • Basement
    Partial

  • Acres
    0.17
  • Lot Features
    Level
  • Water
    Public

  • County
    Middlesex
  • City
    Middletown
  • Zip Code
    06457
  • High School
    Per Board of Ed
  • Middle School
    Per Board of Ed
  • Elementary School
    Per Board of Ed

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Frequently Asked Questions

How do I schedule a tour of 227 E Main St?

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 227 E Main St.

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

How do I get more information about 227 E Main St?

Click Ask a Question to talk with our team. You already know it is a 9 bed, 3 bath, listed for $600,000. We can talk through recent upgrades, potential seller motivation, how this triplex compares to others in Middletown, and can even get you in to see the property quickly.

How much is the monthly mortgage payment for 227 E Main St?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 227 E Main St at around $4,317. 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 227 E Main St?

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 Middlesex 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 227 E Main St?

In most cases, yes. Whether 227 E Main St is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Middletown'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 227 E Main St?

We can handle that for you. Our preferred local agent specializes in residential incomes in Middletown 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 $600,000 with 3,180 sqft of space—that comes out to approximately $189 per square foot.

How long has this property been on the market?

227 E Main St was listed on September 23, 2026, which means it's been on the market for 52 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 1991, making it approximately 35 years old.

What is the lot size of this property?

227 E Main St sits on a 0.17-acre lot, which is 7,405 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

  • Elementary: Per Board of Ed
  • Middle: Per Board of Ed
  • High: Per Board of Ed

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

What are the property taxes for 227 E Main St?

The most recent public record shows annual property taxes for 227 E Main St were approximately $10,833. 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 227 E Main St still available for sale?

This home is under contract, but may still accept backup offers. Click ♥ to track updates or connect with our local expert to see if it's still worth pursuing.

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 14, 2026 at 02:17AM | Source: SmartMLS | MLS#: 24209312