1227 Westbrook St
Pending
Pending
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...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.
- Listed by Heather Shields • Legacy Properties Sotheby's International Realty
Property Details for 1227 Westbrook Street
Waterfront
Yes
ArchitecturalStyleColonial
Garage Spaces.00
GarageNo
ZoningR2
ViewTrees/Woods, Scenic
Subdivision NameStroudwater Village
LISTING UPDATED: 05/01/2026 02:00 PM
Property Details for 1227 Westbrook Street
| Status | Pending |
|---|---|
| MLS # | 1658834 |
| Days on Market | 3 |
| Taxes | $8,127 / year |
| HOA Fees | - |
| Condo/Co-op Fees | - |
| Property Type | Multi Family |
| MLS Type | Multi-Family |
| Year Built | 1730 |
| Lot Size | 0.38 AC / 16,552 SF |
| County | Cumberland County |
Location
Listing Courtesy of Legacy Properties Sotheby's International Realty
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Building Information for 1227 Westbrook Street
Stories2Residences2Year Built1730Building Size-Lot Size0.38 AC / 16,552 SF
Payment Calculator
$3,164 per month
30 year fixed, 6.36% Interest
Principal and Interest
$2,487
Property Taxes
$677
HOA Dues
$0
The Payment Calculator is for illustrative purposes only.
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1Property Information for 1227 Westbrook Street
Summary
Location and General Information
- Road Surface Type: Paved
- Water Body Name: Fore River
- Zip Code: 1929
- Directions: Congress Street to Westbrook Street (historic Stroudwater Village)
- Town: Portland
- State/Province: ME
- Zip Code: 04102
- County: Cumberland
- Geo Latitude: 43.657119
- Geo Longitude: -70.310259
- Tax Lot: 006-001
- Site:Level: Yes
- Site:Open: Yes
- Site:Rolling/Sloping: Yes
- Site:Sidewalks: Yes
- Site:Well Landscaped: Yes
- Site:Wooded: Yes
- Location:Historic District: Yes
- Location:Intown: Yes
- Location:Near Country Club: Yes
- Location:Near Golf Course: Yes
- Location:Near Public Beach: Yes
- Location:Near Shopping: Yes
- Location:Near Turnpike/Interstate: Yes
- Location:Office Park: Yes
- Location:Retail Strip: Yes
- Location:Shopping Mall: Yes
- Transportation:Major Road Access: Yes
- Transportation:Near Airport: Yes
- Transportation:Public Transport Access: Yes
- Transportation:Rail Available: Yes
- Water Info:Waterfront Amount +: 72.00
- Water Info:Water Frontage Owned: 72.00
- Water Info:Water Frontage Shared: .00
- Source of Water Frontage:Waterfront Other Source: Boundary Survey
- Recreational Water:Deeded: Yes
- Recreational Water:Oceanfront: Yes
- Recreational Water:River/Brook/Stream: Yes
- Construction: Wood Frame
- Water View2: Yes
- Tree Growth YN2: false
Parking
- Parking Features: 1 - 4 Spaces, Gravel, On Site
- Attached Garage: No
- Parking: 1 - 4 Spaces, On Site2
Taxes and HOA Information
- Tax Book Number: 38015
- Tax Block: E
- Tax Map Number: 213
- Tax Year: 2025
- Parcel Number: PTLD-000213-E000006-000001
- Location Information:Association Y/N: No
- Tax Annual Amount: $8,127.23
Property
Heating and Cooling
- Water Heater:Electric: No
- Water Heater:Heat Pump: Yes
- Heat Fuel: Electric
- Heat System: Heat Pump
Lot Information
- SqFt Finished Below Grade: 0.0
- SqFt Finished Above Grade: 2061.0
- Lot Size Acres: 0.38
- Source of Acreage: Public Records
- Building Area Total: 2061.0
- Lot Size Area: 0.38
- Lot Size Units: Acres
- Lot Size Square Feet: 16552.8
- Bathrooms Full: 2
- Bathrooms Half: 0
- Street Number: 1227
- Property Information:Surveyed: Yes
- Property Information:Seasonal: No
- Property Information:Owner Occupied: Yes
- Property Information:Deed: All
- Property Information:Deed Restrictions: Unknown
- Property Information:2 Detached Houses on 1 Lot: No
- Property Information:Total Half Baths: .00
- Property Information:Color: Tan
- Property Information:Other Source of Square Footage: Matterport
Parking
- Driveway:Gravel: Yes
- Driveway: Gravel
Property and Assessments
- Sign on Property: Yes
- Leased Land: No
- Property Type: Multi-Family
- Property Type Label: Multi-Family
- Year Built: 1730
Utilities
- Electric: True
- Sewer: Public Sewer
- Water Source: Public
- Other Equipment: Internet Access Available, Cable
- Utilities:Utilities On: Yes
- Gas:No Gas: Yes
- Water Heater: Heat Pump2
- Equipment: Cable, Internet Access Available
Interior and Exterior Features
Exterior Features
- Construction Materials: Shingle Siding, Clapboard, Wood Frame
- Vehicle Storage:No Vehicle Storage: Yes
- Roof: Shingle
- Patio and Porch Features:Deck: Yes
- Vehicle Storage: No Vehicle Storage
- Patio and Porch Features: Deck
- Basement Entry: Bulkhead2, Interior
Interior Features
- Basement: Bulkhead, Partial
- Flooring: Wood, Tile, Carpet
- Interior Features: 1st Floor Bedroom, Attic, Bathtub, Shower, Storage
- Cooling: Heat Pump
- Heating: Heat Pump
- Foundation Details: Concrete Perimeter, Brick/Mortar
- # Stories: 2
- # Floors: 2
- Bathrooms Total (Integer): 2
- Bathrooms Total (Decimal): 2.00
- Bathrooms Total (Notational): 2.00
- Cooling YN: Yes
- Heating YN: Yes
- Amenities: 1st Floor Bedroom, Attic, Bathtub, Shower, Storage
Multi Family
Income & Expenses Information
- Gross Income: $48,000.00
- Operating Expenses: $3,828.00
- Gross Income: $48,000.00
- Operating Expenses: $3,828.00
Multi-Family Information
- Number of Units: 2
- Building Info:# Stories: 2
- Building Info:# Floors: 2
Unit 1
- Unit 1:Lease: Yes
- Unit 1:Level: First
- Unit 1:Security Deposit: Yes
- Unit 1:Monthly Rent: $1,950.00
- Unit 1:# Full Baths: 1.00
- Unit 1:# of Half Baths: .00
- Unit 1:# of Rooms: 4.00
- Unit 1:# of Bedrooms: 3.00
- Unit 1:Dedicated Electric Meter: Yes
- Unit 1:Dedicated Gas Meter: No
- Unit 1:Dedicated Water Heater: Yes
- Unit 1:Electric: No
- Unit 1:Heat: No
- Unit 1:Range: Yes
- Unit 1:Refrigerator: Yes
- Unit 1:Sewer: Yes
- Unit 1:Water: Yes
Unit 2
- Unit 2:Lease: Yes
- Unit 2:Level: Second
- Unit 2:Monthly Rent: $2,050.00
- Unit 2:# Full Baths: 1.00
- Unit 2:# Half Baths: .00
- Unit 2:# of Rooms: 4.00
- Unit 2:# of Bedrooms: 2.00
- Unit 2:Dedicated Electric Meter: Yes
- Unit 2:Dedicated Gas Meter: No
- Unit 2:Dedicated Water Heater: Yes
- Unit 2:Electric: No
- Unit 2:Heat: No
- Unit 2:Range: Yes
- Unit 2:Refrigerator: Yes
- Unit 2:Sewer: Yes
- Unit 2:Water: Yes
Unit 3
- Unit 3:Range: Yes
- Unit 3:Sewer: Yes
Unit Information
- Units:# of 1 BD Units: 0
- Units:# of 2 BD Units: 2
- Units:# of 3 BD Units: 0
- Units:# of 4+ BD Units: 0
Property History for 1227 Westbrook Street
| Date | Event & Source | Price | Appreciation |
|---|---|---|---|
| May 1, 2026 | Pending Maine Listings #1658834 | — | |
| Apr 30, 2026 | Active Under Contract Maine Listings #1658834 | — | |
| Feb 9, 2026 | Listed (Active) Maine Listings #1658834 | $499,000 | — |
| Jun 19, 2020 | Sold Maine Listings #1420747 | $390,000 | — |
| May 7, 2020 | Pending Maine Listings #1420747 | — | |
| May 6, 2020 | Active Under Contract Maine Listings #1420747 | — | |
| Jun 19, 2019 | Listed (Active) Maine Listings #1420747 | $495,000 | — |
| Dec 25, 2018 | Expired Maine Listings #1364267 | $595,000 | — |
| Dec 25, 2018 | Expired Maine Listings #1359003 | $695,000 | — |
| Jun 25, 2018 | Listed (Active) Maine Listings #1364267 | $595,000 | — |
| Jun 25, 2018 | Listed (Active) Maine Listings #1359003 | $595,000 | — |
| Date | Event & Source | Price |
|---|---|---|
| 05/01/2026 | Pending Maine Listings #1658834 | — |
| 04/30/2026 | Active Under Contract Maine Listings #1658834 | — |
| 02/09/2026 | Listed (Active) Maine Listings #1658834 | $499,000 |
| 06/19/2020 | Sold Maine Listings #1420747 | $390,000 |
| 05/07/2020 | Pending Maine Listings #1420747 | — |
| 05/06/2020 | Active Under Contract Maine Listings #1420747 | — |
| 06/19/2019 | Listed (Active) Maine Listings #1420747 | $495,000 |
| 12/25/2018 | Expired Maine Listings #1364267 | $595,000 |
| 12/25/2018 | Expired Maine Listings #1359003 | $695,000 |
| 06/25/2018 | Listed (Active) Maine Listings #1364267 | $595,000 |
| 06/25/2018 | Listed (Active) Maine Listings #1359003 | $595,000 |
For completeness, we often displays two records for one sale: the MLS record and the public record.
Public Records for 1227 Westbrook Street
Taxable ValueLand$218,100Additions$485,300Total$703,400
Tax Record2025$8,427 ($702 / month)
Home Facts
Baths2Total Finished SqFt2,250 SqFtAbove Grade Finished SqFt2,250 SqFtStories2Lot Size16,888 SqFtStyleDuplexYear Built1730CountyCUMBERLANDAPNPTLD M:213 B:E006001
Schools near 1227 Westbrook Street
This home is within Portland Public Schools.
Rating | School | Type | Grades | Distance |
|---|---|---|---|---|
| Public - | PK to 5 | |||
| Public - | 6 to 8 | |||
| Public - | 9 to 12 | |||
| Public - | 9 to 12 |
Rating | School | Distance |
|---|---|---|
Amanda C Rowe School PublicPK to 5 | ||
King Middle School Public6 to 8 | ||
Deering High School Public9 to 12 | ||
Portland High School Public9 to 12 |
School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.
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No guarantee, warranty or representation of any kind is made regarding the completeness or accuracy of descriptions or measurements (including square footage measurements and property condition), such should be independently verified, and Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties expressly disclaims any liability in connection therewith. Photos may be virtually staged or digitally enhanced and may not reflect actual property conditions. Offers of compensation are subject to change at the discretion of the seller. No financial or legal advice provided. Equal Housing Opportunity. Subject to change at any time. Compass, Inc., its subsidiaries, affiliates and their agents and associated third parties make no guarantee, warranty or representation regarding the accuracy of any waterfront feature, water view or waterfront view.
Listing Courtesy of Legacy Properties Sotheby's International Realty
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.
