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

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
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
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
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Aug 13, 2026per 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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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.