1227 Westbrook Street, Portland, ME 04102
Local realty services provided by:Better Homes and Gardens Real Estate The Masiello Group
1227 Westbrook Street,Portland, ME 04102
$499,000
- - Beds
- 2 Baths
- - sq. ft.
- Multi-family
- Coming Soon
Listed by: heather shields
Office: legacy properties sotheby's international realty
MLS#:1658834
Source:ME_MREIS
Price summary
- Price:$499,000
About this home
A rare opportunity to reimagine a historic waterfront property with incredible potential. Set along the Stroudwater and Fore Rivers with access to Casco Bay, this unique offering combines a peaceful, tucked-away setting with a highly convenient location just minutes from Portland's amenities. Known as the Isaac Fly House, this Colonial-era home dates back to approximately 1730 and may be among the oldest residences in Portland. Rich in history and character, it remains a notable presence in the city's historic Stroudwater Village. Enhancing its potential, the property includes a thoughtfully designed construction set by Scott Simons that previously received approval from the Portland Historic Preservation Board (approval has since expired and would require reapplication). The plans envision meaningful additions and exterior/site improvements, including a garage and expanded living space, and are complemented by renderings that help bring the vision to life. The property was also surveyed in 2020. Originally built as a single-family residence, the home is currently configured as a two-unit property, with two-bedroom, one-bath units on each level. This flexible layout lends itself to a variety of uses, including multi-generational living, rental income, or conversion back to a single-family home. Situated on over a third of an acre, the lot offers ample space for expansion and site enhancements. The interior and exterior need significant improvement; the seller obtained quotes for the basement, roof, siding, and trim replacement, though no work has been completed. Buyers are encouraged to perform their own due diligence. Enjoy striking sunrise views and a setting that feels worlds away--where evenings are accompanied by the sound of the falls and days invite kayaking to Thompson's Point for waterfront concerts or exploring the nearby Fore River Preserve trails....
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Home facts
- Year built:1730
- Listing ID #:1658834
- Updated:April 23, 2026 at 03:11 PM
Rooms and interior
- Total bathrooms:2
- Full bathrooms:2
- Flooring:Carpet, Tile, Wood
- Bathrooms Description:Bathtub, Shower
- Bedroom Description:1st Floor Bedroom
- Basement Description:Bulkhead, Partial
Heating and cooling
- Heating:Heat Pump
Structure and exterior
- Year built:1730
- Lot Features:Historic District, Intown, Level, Near Golf Course, Near Public Beach, Near Public Transit, Near Shopping, Near Turnpike/Interstate, Office Park, Open, Retail Strip, Rolling/Sloping, Shopping Mall, Sidewalks, Well Landscaped, Wooded
- Architectural Style:Colonial
- Construction Materials:Clapboard, Shingle Siding, Wood Frame
- Exterior Features:Deck
- Foundation Description:Brick/Mortar, Concrete Perimeter
Utilities
- Water:Public
- Sewer:Public Sewer
Finances and disclosures
- Price:$499,000
- Tax amount:$8,127 (2025)
Features and amenities
- Amenities:Storage
Parking
- Parking description:1 - 4 Spaces, Gravel, On Site
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