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227 East Main Street

Middletown, Connecticut 06457

ACTIVE$749,900

Reduced from $850,000

Beds
9
Baths
3 | 3
SqFt
3,180
Acres
0.17
Year Built
1991
Matt Caiola

Matt Caiola

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MCMATT CAIOLALUXURY PROPERTIES
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3-Car GaragePrice Reduced

About This Home

Outstanding Mixed-Use Investment Opportunity at 227 East Main Street, Middletown, CT Now offered at a newly reduced price, 227 East Main Street presents an exceptional opportunity for investors or owner-occupants seeking strong income potential and long-term value. This well-maintained mixed-use property features three spacious townhouse-style residential units, each offering 3 bedrooms, 1 full bath, 1 half bath, bright living spaces, and eat-in kitchens-highly desirable layouts that help attract and retain tenants. A standout feature is that each unit includes its own private under-house garage with direct access, creating the convenience and feel of a single-family home. The property also offers ample off-street parking and a driveway behind the building, providing easy access and added convenience for residents and guests. Separate utilities, hardwood floors, abundant natural light, and additional basement storage further enhance the property's appeal and ease of management. Ideally located near downtown Middletown, shopping, dining, parks, major commuter routes, Wesleyan University, and Middlesex Health, this property benefits from strong rental demand and excellent accessibility. With its price improvement, desirable townhouse-style units, private garages, ample parking, and proven income-producing potential, 227 East Main Street is a compelling investment opportunity in the heart of Middletown. Agent owner related.

Key Facts

City/Town
Middletown
Neighborhood
N/A
Property / Style
Multi-Family · 3sides - Units Are Side-by-Side
Year Built
1991
Days on Market
109 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

59

10 active listings

Median $ / Sq Ft

$148

10 active listings

Sale-to-List Ratio

103.0%

47 sales

How this home compares

List Price

$749,900

vs $534,450 median

40.3% above median

Price / Sq Ft

$236

vs $148 median

59.5% above median

Days on Market

109 days

vs 59 days median

50 days longer 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
$5,012

per month

  • Principal & Interest$3,859
  • Property Taxes$903
  • Insurance$250
  • 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
3sides - 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
PartialGarage AccessConcrete Floor

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
Flood Zone
No
Construction
Vinyl Siding
Color
Beige
Roof
Asphalt ShingleGable
Foundation
Concrete
Exterior Features
Sidewalk
Lot Description
N/A

Listing & Financials

Property Taxes
$10,833 / Annually
Days on Market
109
MLS #
24171799
MLS Status
Active

Similar Properties

Homes with a close match in area, property type, and price.

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 2:50 AM UTC.