356 Main Street
Portland, Connecticut 06480
- Beds
- 9
- Baths
- 4
- SqFt
- 3,720
- Acres
- 1.03
- Year Built
- 1827
- Property Type
- 4 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
Investor alert in the heart of Portland! Welcome to 354-356 Main Street, a rare 4-unit multifamily offering incredible upside, strong rental potential, and a layout that works beautifully for both investors and owner-occupants. Priced with condition in mind, property is being sold as-is. Two units are currently month-to-month and well below market rent, creating a major value-add opportunity from day one. Projected rents offer impressive income potential, with units estimated around $1,600/month, the spacious townhouse-style unit around $2,000/month, and the 3-bedroom unit around $1,800/month. This property also features a huge backyard, offering outdoor space rarely found with multifamily properties. Whether tenants want room to relax, garden, grill, or enjoy extra green space, this yard adds major appeal. Need storage, workspace, or a place to bring your hobbies to life? The detached garage needs work, but with the right handy buyer, it could be transformed into an amazing workshop, storage space, or dream setup for mechanics, gearheads, contractors, or anyone needing extra room. Major Bonus: The oil furnaces were replaced aproximatley 4 years ago. Perfect for investors looking to increase rents and build long-term cash flow, or an owner-occupant looking to live in one unit while the others help pay the mortgage. OPEN HOUSE SAT/SUN 1-3PM You will be able to get into ALL 4 units and basement
Key Facts
- City/Town
- Portland
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Other
- Year Built
- 1827
- Days on Market
- 19 days
- Beds
- 9
- Baths
- 4 full
- Living Area
- 3,720 sq ft
- Lot Size
- 1.03 acres
- Property Taxes
- $8,196 / Annually
Market Snapshot
The Portland Market
Multi-Family · trailing 12 months
Active Listings
1
2 under contract
Median List Price
$449,000
1 active listing
Median Closed Price
$400,000
5 sales
Median Days on Market
35
1 active listing
Median $ / Sq Ft
$123
1 active listing
Sale-to-List Ratio
105.4%
5 sales
How this home compares
List Price
$499,900
vs $449,000 median
11.3% above median
Price / Sq Ft
$134
vs $123 median
8.9% above median
Days on Market
19 days
vs 35 days median
16 days fresher than median
Based on 1 active and 5 closed sales (trailing 12 mo) of multi-family in Portland. Source: SmartMLS · As of July 28, 2026.
Location
356 Main Street, Portland, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,549
- Property Taxes$683
- Insurance$167
- HOA$0
Estimates only. Actual rates, taxes, insurance, and HOA fees vary. Consult a lender for current rates.
Location
- City/Town
- Portland
- Neighborhood
- N/A
- County
- Middlesex
Residence
- Property Type
- Multi-Family
- Subtype
- Quadruplex
- Style
- Other
- Year Built
- 1827
- New Construction
- No/Resale
- Living Area
- 3,720 sq ft
Schools
- Elementary
- Per Board of Ed
- High
- Per Board of Ed
Interior
- Heating
- Hot Water
- Heat Fuel
- Oil
- Cooling
- Ceiling FansWall Unit
- Laundry
- None
- Basement
- FullUnfinished
Exterior & Lot
- Lot Size
- 1.03 acres
- Zoning
- R10
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Aluminum
- Roof
- Shingle
- Foundation
- Stone
- Lot Description
- Lightly WoodedLevel Lot
Listing & Financials
- Property Taxes
- $8,196 / Annually
- Days on Market
- 19
- MLS #
- 24182877
- MLS Status
- Under Contract - Continue to Show
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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 4:25 AM UTC.