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356 Main Street

Portland, Connecticut 06480

PENDING$499,900
Beds
9
Baths
4
SqFt
3,720
Acres
1.03
Year Built
1827
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

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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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,399

per 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

Similar Properties

Homes with a close match in area, property type, and price.

Listed By

Jeni Mascaro

(860) 558-8993

LPT Realty

(877) 366-2213

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.