227 East Main Street
Middletown, Connecticut 06457
Reduced from $850,000
- Beds
- 9
- Baths
- 3 | 3
- SqFt
- 3,180
- Acres
- 0.17
- Year Built
- 1991
- Property Type
- 3 Family

Matt Caiola
Luxury Real Estate Advisor
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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
Active Listings
10
6 under contract
Median List Price
$534,450
10 active listings
Median Closed Price
$385,000
47 sales
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per 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
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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.