286 Marlborough Street
Portland, Connecticut 06480
Reduced from $575,000
- Beds
- 2
- Baths
- 2 | 1
- SqFt
- 4,205
- Acres
- 1.11
- Year Built
- 1850
- Property Type
- 2 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
This unique property presents an exceptional opportunity for both investors and owner-occupants seeking flexibility and income potential. The upper level offers a well-appointed two-bedroom, one-bath apartment filled with natural light-perfect for immediate occupancy or reliable rental income. On the first floor, a spacious layout that previously operated as a salon provides a blank canvas for transformation. With its size and configuration, it can be thoughtfully converted into a three-bedroom residential unit, creating a true two-family property. The flexibility here is a standout feature-convert the first floor to expand into a full two-unit residential property, or maintain the commercial space below while generating rental income above. This opens the door to a variety of strategies, from live/work setups to mixed-use investment potential. Located in a desirable area with excellent visibility and accessibility, the property also carries a unique edge, having been used as a filming location-adding character and distinction. Whether you're looking to expand your portfolio or secure a flexible living arrangement with income potential, this property offers a rare combination of adaptability and value.
Key Facts
- City/Town
- Portland
- Neighborhood
- N/A
- Property / Style
- Multi-Family · Units on different Floors
- Year Built
- 1850
- Days on Market
- 118 days
- Beds
- 2
- Baths
- 2 full · 1 half
- Living Area
- 4,205 sq ft
- Lot Size
- 1.11 acres
- Garage / Parking
- 15 total
- Property Taxes
- $8,315 / 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
$499,000
vs $449,000 median
11.1% above median
Price / Sq Ft
$119
vs $123 median
In line with median
Days on Market
118 days
vs 35 days median
83 days longer 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
286 Marlborough Street, Portland, Connecticut
Estimate Your Payment
Estimated Monthly Payment
Rates: Freddie Mac PMMS via FRED · Updated Jul 23, 2026per month
- Principal & Interest$2,544
- Property Taxes$693
- Insurance$166
- 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
- Duplex
- Style
- Units on different Floors
- Year Built
- 1850
- New Construction
- No/Resale
- Living Area
- 4,205 sq ft
Schools
- Elementary
- Gildersleeve
- Middle
- Brownstone
- High
- Portland
Interior
- Heating
- Hot Water
- Heat Fuel
- Electric
- Cooling
- Window Unit
- Basement
- Full
Exterior & Lot
- Lot Size
- 1.11 acres
- Zoning
- B2
- Garage / Parking
- 15 total parking spacesPavedParking LotOff Street Parking
- Waterfront Details
- Not Applicable
- Water Source
- Public Water Connected
- Sewer
- Public Sewer Connected
- Construction
- Vinyl SidingBrick
- Color
- White
- Roof
- Asphalt Shingle
- Foundation
- MasonryStone
- Lot Description
- SecludedLevel LotRolling
Listing & Financials
- Property Taxes
- $8,315 / Annually
- Days on Market
- 118
- MLS #
- 24162055
- MLS Status
- Under Contract
Similar Properties
Homes with a close match in area, property type, and price.
Co-Listed By
Steve Annecharico
Eagle Eye Realty PLLC
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 6:50 AM UTC.