1227 Westbrook Street, Portland, ME 04102

New Listing
$499,000
Property Type: Multi-Family Baths: 2 Square Footage: 2,061 Lot Size (sq. ft.): 16,553 Status: Active
Current Price: $499,000 List Date: 4/27/2026 Last Modified: 4/27/2026

Description

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.

Supplements: ********

More Information MLS# 1658834

Location Information

Street #: 1227 Street Name: Westbrook Street Type: Street County: Cumberland Town: Portland State/Province: ME Zip Code: 04102 Zip +4: 1929 Leased Land: No Book: 38015 Page: 325, 326 Map: 213 Block: E Lot: 006-001 Zoning: R2 Zoning Overlay: Unknown Neighborhood Association: Stroudwater Village Association: No Full Tax Amount $: 8127.23 Tax Year: 2025 Tree Growth Y/N: No Geo Lat: 43.657119 Geo Lon: -70.310259

Contract Information

Status: Active Original List Price: 499000 List Price: $499,000 Current Price: $499,000

Property Information

Surveyed: Yes Seasonal: No Owner Occupied: Yes Deed: All Deed Restrictions: Unknown 2 Detached Houses on 1 Lot: No Number of Units: 2 Total Baths: 2 Total Full Baths: 2 Color: Tan Year Built: 1730 SqFt Finished Above Grade: 2061 SqFt Finished Total: 2061 SqFt Source: Other Other Source of Square Footage: Matterport Garage: No Lot Size Acres +/-: 0.38 Source of Acreage: Public Records

Water Info

Water Frontage: Yes Waterfront Amount: 72 Water Frontage Owned: 72 Water View: Yes Water Body Name: Fore River

Source of Water Frontage

Waterfront Other Source: Boundary Survey

Building Info

# Stories: 2 # Floors: 2

Units

# of 2 BD Units: 2

Unit 1

Lease: Yes Level: First Security Deposit: Yes Monthly Rent: 1950 # Full Baths: 1 # of Rooms: 4 # of Bedrooms: 3 Dedicated Electric Meter: Yes Dedicated Gas Meter: No Dedicated Water Heater: Yes Electric: No Heat: No Range: Yes Refrigerator: Yes Sewer: Yes Water: Yes

Unit 2

Lease: Yes Level: Second Security Deposit: Yes Monthly Rent: 2050 # Full Baths: 1 # of Rooms: 4 # of Bedrooms: 2 Dedicated Electric Meter: Yes Dedicated Gas Meter: No Dedicated Water Heater: Yes Electric: No Heat: No Range: Yes Refrigerator: Yes Sewer: Yes Water: Yes

Utilities

Utilities On: Yes

Property Features

Site: Level; Open; Rolling/Sloping; Sidewalks; Well Landscaped; Wooded Location: Historic District; Intown; Near Country Club; Near Golf Course; Near Public Beach; Near Shopping; Near Turnpike/Interstate; Office Park; Retail Strip; Shopping Mall Roads: Paved; Public Transportation: Major Road Access; Near Airport; Public Transport Access; Rail Available Water Body Type: Ocean; River Recreational Water: Deeded; Oceanfront; River/Brook/Stream View: Scenic; Trees/Woods Style: Colonial Construction: Wood Frame Basement: Bulkhead; Partial Basement Entry: Bulkhead; Interior Foundation Materials: Brick/Mortar; Poured Concrete Exterior: Clapboard; Shingle Siding Roof: Shingle Heat System: Heat Pump Water Heater: Heat Pump Cooling: Heat Pump Floors: Carpet; Tile; Wood Amenities: 1st Floor Bedroom; Attic; Bathtub; Shower; Storage Patio and Porch Features: Deck Equipment: Cable; Internet Access Available Driveway: Gravel Parking: 1 - 4 Spaces; On Site Vehicle Storage: No Vehicle Storage Electric: Circuit Breakers Gas: No Gas Sewer: Public Sewer Water: Public
Listing Office: Legacy Properties Sotheby's International Realty
Last Updated: April - 27 - 2026
1227 Westbrook Street, Portland, ME 04102- MLS# 1658834
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. Copyright ©2026 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.