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286 Marlborough Street

Portland, Connecticut 06480

PENDING$499,000

Reduced from $575,000

Beds
2
Baths
2 | 1
SqFt
4,205
Acres
1.11
Year Built
1850
Matt Caiola

Matt Caiola

Luxury Real Estate Advisor

MCMATT CAIOLALUXURY PROPERTIES
Higgins Group Private Brokerage

Request a private showing and get Matt's read on price, condition, and next steps.

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Price Reduced

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

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

Property + 12 nearby

Estimate Your Payment

Estimated Monthly Payment

Rates: Freddie Mac PMMS via FRED
$3,403

per 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.

Listed By

Krob Robinson

(860) 810-2567

Eagle Eye Realty PLLC

(860) 263-9102

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.