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227 East Main Street

Middletown, Connecticut 06457

ACTIVE - NEW$649,900
Beds
9
Baths
3 | 3
SqFt
3,180
Acres
0.17
Year Built
1991
Matt Caiola

Matt Caiola

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About This Home

Exceptional 3-Unit Mixed-Use Investment Opportunity A rare opportunity to own a well-maintained three-unit property offering townhouse-style living, private garages, excellent parking, and strong income-producing potential in the heart of Middletown. 227 East Main Street is an attractive investment opportunity for both seasoned investors and owner-occupants looking to build equity while generating rental income. The property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bathroom, and 1 half bathroom. The desirable layouts include bright, comfortable living spaces and eat-in kitchens, creating a residential feel that appeals to a broad range of tenants. One of the property's most compelling features is the private under-building garage for each unit, complete with direct access. This added convenience provides residents with the feel and functionality of a single-family home-an especially desirable feature in a multi-family property. Additional highlights include separate utilities, hardwood flooring, abundant natural light, basement storage, Washer dryer hook-ups in each unit, ample off-street parking, and a rear driveway providing convenient access behind the building. Separate utilities offer practical advantages for ownership and day-to-day management. Situated near downtown Middletown, Wesleyan University, Middlesex Health, shopping, dining, parks, and major commuter routes. Agent owner related.

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Multi-Family · Units are Side-by-Side
Year Built
1991
Days on Market
0 days
Beds
9
Baths
3 full · 3 half
Living Area
3,180 sq ft
Lot Size
0.17 acres
Garage / Parking
3 garage · 6 total
Property Taxes
$10,833 / Annually

Market Snapshot

The Middletown Market

Multi-Family · trailing 12 months

Median Days on Market

58

10 active listings

Median $ / Sq Ft

$148

10 active listings

Sale-to-List Ratio

103.0%

47 sales

How this home compares

List Price

$649,900

vs $534,450 median

21.6% above median

Price / Sq Ft

$204

vs $148 median

37.8% above median

Days on Market

0 days

vs 58 days median

58 days fresher than median

Based on 10 active and 47 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of August 18, 2026.

Location

227 East Main Street, Middletown, Connecticut

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$4,465

per month

  • Principal & Interest$3,345
  • Property Taxes$903
  • Insurance$217
  • HOA$0

Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.

Location

City/Town
Middletown
Neighborhood
N/A
County
Middlesex

Residence

Property Type
Multi-Family
Subtype
3 Family
Style
Units are Side-by-Side
Year Built
1991
New Construction
No/Resale
Living Area
3,180 sq ft

Schools

Elementary
Per Board of Ed
Middle
Per Board of Ed
High
Per Board of Ed

Interior

Heating
Baseboard
Heat Fuel
Electric
Cooling
Window Unit
Laundry
All Units Have Hook-UpsBasement Hook-Up(s)
Basement
Partial

Exterior & Lot

Lot Size
0.17 acres
Zoning
MXI
Garage / Parking
3 garage spaces6 total parking spacesUnder House GaragePavedOff Street ParkingDrivewayPaved
Waterfront Details
Not Applicable
Water Source
Public Water Connected
Sewer
Public Sewer Connected
Construction
Vinyl Siding
Color
Beige
Roof
Shingle
Foundation
Concrete
Lot Description
Level Lot

Listing & Financials

Property Taxes
$10,833 / Annually
Days on Market
0
MLS #
24199960
MLS Status
Active

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Listed By

Tanya Reyes

(860) 538-4448

William Raveis Real Estate

(860) 344-1658

This information is believed to be accurate, but without warranty.

The IDX display contains information sourced from SmartMLS, Inc. as of 8/18/2026. 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 8/18/2026 at 1:41 AM UTC.