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
Luxury Real Estate Advisor
Request a private showing and get Matt's read on price, condition, and next steps.
About This Home
Exceptional 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.
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
9
10 under contract
Median List Price
$649,900
9 active listings
Median Closed Price
$375,000
47 sales
Median Days on Market
90
9 active listings
Median $ / Sq Ft
$158
9 active listings
Sale-to-List Ratio
102.8%
47 sales
How this home compares
List Price
$600,000
vs $649,900 median
7.7% below median
Price / Sq Ft
$189
vs $158 median
19.6% above median
Days on Market
0 days
vs 90 days median
90 days fresher than median
Based on 9 active and 47 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of September 24, 2026.
Location
227 East Main Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Sep 17, 2026per month
- Principal & Interest$3,177
- Property Taxes$903
- Insurance$200
- 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 #
- 24209312
- MLS Status
- Active
Similar Properties
Homes with a close match in area, property type, and price.
This information is believed to be accurate, but without warranty.
The IDX display contains information sourced from SmartMLS, Inc. as of 9/24/2026. 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 9/24/2026 at 3:35 AM UTC.