Portland Street
Middletown, Connecticut 06457
- Beds
- 8
- Baths
- 4
- SqFt
- 5,176
- Acres
- 0.35
- Year Built
- 1900
- Property Type
- 4 Family

Matt Caiola
Luxury Real Estate Advisor
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About This Home
Exceptional Multi-Family Investment Opportunity in CT! Located in desirable Middletown, this unique property package offers two two-family homes-for a total of four income-producing units-along with a versatile 2,898 sq ft workshop and two additional vacant land parcels. Each residential building offers approximately 1,380 sq ft with new roofs, new windows, upgraded electrical, and modernized plumbing-providing peace of mind for years to come. All properties are connected to natural gas, adding efficiency and convenience. One unit has been fully renovated, supplies to renovate the other units are located in the workshop. The standout feature is the expansive heated workshop with electricity and plumbing already in place, opening the door to endless possibilities-ideal for contractors, hobbyists, storage, or potential additional income use. Set on a combined .25-acre lot, plus two separate parcels (.08 and .02 acres), this offering provides flexibility rarely found * Expand your portfolio with strong rental income potential * Build on the additional lot (buyer to do due diligence) * Or enjoy extra outdoor space as a private side yard. Whether you're an investor looking for solid cash flow or an owner-occupant seeking supplemental income, this property delivers versatility, updates, and long-term value in one compelling package.
Key Facts
- City/Town
- Middletown
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors,Units are Side-by-Side
- Year Built
- 1900
- Days on Market
- 116 days
- Beds
- 8
- Baths
- 4 full
- Living Area
- 5,176 sq ft
- Lot Size
- 0.35 acres
- Property Taxes
- $8,719 / Annually
Market Snapshot
The Middletown Market
Multi-Family · trailing 12 months
Active Listings
10
9 under contract
Median List Price
$419,500
10 active listings
Median Closed Price
$388,000
45 sales
Median Days on Market
38
10 active listings
Median $ / Sq Ft
$152
10 active listings
Sale-to-List Ratio
103.5%
45 sales
How this home compares
List Price
$1.10M
vs $419,500 median
2.6× the median
Price / Sq Ft
$213
vs $152 median
40.1% above median
Days on Market
116 days
vs 38 days median
78 days longer than median
Based on 10 active and 45 closed sales (trailing 12 mo) of multi-family in Middletown. Source: SmartMLS · As of July 28, 2026.
Location
Portland Street, Middletown, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$5,609
- Property Taxes$727
- Insurance$367
- 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
- Quadruplex
- Style
- Units on different Floors,Units are Side-by-Side
- Year Built
- 1900
- New Construction
- No/Resale
- Living Area
- 5,176 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Baseboard
- Heat Fuel
- Natural Gas
- Cooling
- None
- Laundry
- All Units Have Hook-Ups
- Laundry Location
- basement and 2nd floor hook ups
- Basement
- PartialPartial With Hatchway
Exterior & Lot
- Lot Size
- 0.35 acres
- Zoning
- MXI
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl SidingStucco
- Roof
- Asphalt ShingleMetal
- Foundation
- Concrete
- Exterior Features
- DeckGuttersLighting
- Lot Description
- Level Lot
Listing & Financials
- Property Taxes
- $8,719 / Annually
- Days on Market
- 116
- MLS #
- 24163304
- 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 7/28/2026. 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 7/28/2026 at 7:50 AM UTC.