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7 Beds
5 Baths
5,003 sqft

$1,349,000

381 Deering Avenue, Portland ME, 04103

Built in1925
Property size5,003 sqft
Property typeResidential
Courtesy of Waypoint Brokers Collective

Overview

Active

Listed Aug 12, 2026

Updated 47h ago

Exceptional opportunity to own a gorgeous home with bonus unit in the heart of Portland's sought-after Oakdale neighborhood. Offering over 5,000 square feet across three finished levels, this expansive property seamlessly blends historic character with modern amenities and significant systems updates, creating a rare investment or owner-occupant opportunity. With two spacious residences offering excellent rental income potential, this property provides exceptional flexibility for investors, multigenerational living, or those looking to offset their mortgage while enjoying one of Portland's most desirable neighborhoods. The first-floor residence features three bedrooms, one and a half baths, a generous living room, formal dining room, spacious bedrooms, and a bright bonus sunroom. Occupying the second and third floors, the upper residence lives like a single-family home with a spacious living area, formal dining room, updated kitchen, four generously sized bedrooms, the potential to finish a fifth bedroom, and three inviting sun porches that provide flexible space for relaxing or working from home. Throughout the home, beautifully restored original trim, built-ins, hardwood floors, and timeless architectural details showcase its historic charm, while thoughtful updates to the property's major systems provide peace of mind. Whether you're seeking strong rental income, multi-generational living, or the chance to owner-occupy one of Portland's most impressive two-unit homes, this property offers exceptional space, flexibility, and long-term value in one of the city's most charming neighborhoods.

$8,975/mo

Est. mortgage payment based on a $1,349,000 home price.

All estimates are provided by Luxury Presence for informational purposes only. Actual amounts may vary.

Additional information

MLS® ID
1675911

Interior Features

Bedrooms
7
Bathrooms
5
Fireplace
Yes
Heating
Yes
Basement
Yes

Exterior Features

Lot Size
0.15 Acres

Other Property Details

Taxes
$13,436
Tax Frequency
Annually
Garage
Yes
MLS provider logo

Listing Contact: [email protected]

Listed by Alessandra Malone with Waypoint Brokers Collective [email protected]

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved. All information deemed reliable but not guaranteed and should be independently verified. All properties are subject to prior sale, change, or withdrawal. Neither listing broker(s) nor Blue Lobster Real Estate shall be responsible for any typographical errors, misinformation, misprints and shall be held totally harmless.

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Data is refreshed every 3 hours. Listing last updated at 6:49 AM UTC, 10/9/2026

 

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