OPEN HOUSE SATURDAY IS CANCELLED! Welcome to 142 Longfellow Street, nestled in the quiet leafy streets of Portland's Deering Highlands, one of the city's most sought-after neighborhoods. This home has not been offered for sale in more than two decades. Tastefully renovated while retaining its classic Craftsman charm, it boasts updated systems including a new state-of-the-art boiler and water heater, Andersen architecturally authentic windows throughout, and a no-maintenance gutter system. Its large city lot with spacious back yard offers privacy and mature landscaping with a shady brick patio and private sunny deck off the kitchen. Heavy oak cabinets, granite countertops, newer appliances, and an adjacent sunroom make its eat-in kitchen the heart of the home, perfect for large family gatherings. Its front-to-back living/dining area features a cozy window seat and French doors. You'll find three bedrooms upstairs along with a private office space. When company stays, a comfy den on the first floor with an ensuite bath doubles as a guest room. This home also features a spacious and practical tiled mudroom/pantry and a finished walk-out ground-floor bonus room with full-sized windows and a fireplace (wood-stove insert) for use as a family room or office.
Single-familyProperty Type
1920Year Built
10,454 sq ftLot Size
$477Price/Sq.Ft.
1 spaceParking
Listed by Rollie Heckethorn• Tim Dunham Realty
Contact: 207-729-7297
Bought with Sophia Rosendo Sierra Boler• Portside Real Estate Group
Est. $1,819 per month, based on comparable rentals
Sale and tax history for 142 Longfellow St
Sale History
Tax History
Date
Event
Price
MREIS #1668221
Jul 24, 2026
Sold
$1,150,000
$477/sq ft
Jun 22, 2026
Listed
$1,098,000
$456/sq ft
Year
Property tax
Land + Additions
Assessment*
2024
$9,290 (+4.2%)
$137,400 + $481,500
$618,900
2023
$8,918 (+5.9%)
$137,400 + $481,500
$618,900
2022
$8,423 (+4.8%)
$137,400 + $481,500
$618,900
2021
$8,040 (+8.4%)
$137,400 + $481,500
$618,900
2020
$7,415
$137,400 + $180,700
$318,100
2019
$7,415 (+3.7%)
$137,400 + $180,700
$318,100
2018
$7,151 (+3.8%)
$137,400 + $180,700
$318,100
2017
$6,887 (+2.6%)
$137,400 + $180,700
$318,100
2016
$6,715 (+2.3%)
$137,400 + $180,700
$318,100
2015
$6,562 (+3.1%)
$137,400 + $180,700
$318,100
2014
$6,362
$137,400 + $180,700
$318,100
Public record
Public record
Zoning
Permits
Beds
3
Baths
2
Stories
2
Lot width
—
Lot depth
—
Lot size
10,454 Sq. Ft.
Year renovated
—
Sq. Ft.
2,134
Year built
1920
Style
Single Family Residential
County
Cumberland County
APN
118586
Parking Spaces
—
Basement
—
Accessible
—
HOA Dues
—
Garage
—
Features
—
Last updated by owner on Jul 27, 2026.
R5
Residential
To provide appropriate areas of the city for medium-density residential development characterized by singlefamily, two-family and low-intensity multifamily dwellings on individual lots; to ensure the stability of established medium-density neighborhoods by controlling residential conversions; and to provide for planned residential unit development on substantially-sized parcels.
May 5, 2026 • Active
Hvac
Heat pump
HVAC
Permit history is from public records and may be incomplete or inaccurate. Redfin and its agents make no representations about the property condition or permit status. Buyers should independently verify all information.
Property details
Parking
Parking Information
Parking Features: Paved, 1 - 4 Spaces, On Site, Off Street
Interior
Virtual Tour
Bathroom Information
# of Baths (Full): 2
Room 1 Information
Type: Dining Room
Length (Ft.): 129
Width (Ft.): 125
Level: First
Features: Built-Ins, Formal
Room 2 Information
Type: Bedroom 2
Length (Ft.): 129
Width (Ft.): 106
Level: Second
Room 3 Information
Type: Living Room
Length (Ft.): 129
Width (Ft.): 1,710
Level: First
Room 4 Information
Type: Office
Length (Ft.): 94
Width (Ft.): 1,711
Level: Second
Room 5 Information
Type: Bedroom 1
Length (Ft.): 129
Width (Ft.): 120
Level: Second
Features: Closet
Room 6 Information
Type: Sunroom
Length (Ft.): 1,211
Width (Ft.): 139
Level: First
Features: Four-Season, Gas Fireplace, Heated, Skylight
Room 7 Information
Type: Kitchen
Length (Ft.): 1,211
Width (Ft.): 124
Level: First
Room 8 Information
Type: Bedroom 3
Length (Ft.): 104
Width (Ft.): 120
Level: Second
Room 9 Information
Type: Laundry
Length (Ft.): 170
Width (Ft.): 125
Level: Basement
Room 10 Information
Type: Den
Length (Ft.): 109
Width (Ft.): 1,711
Level: First
Features: Sunken/Raised
Room 11 Information
Type: Family Room
Length (Ft.): 238
Width (Ft.): 139
Level: Basement
Features: Heat Stove
Basement Information
Basement Entry: Interior Entry, Walk-Out Access, Daylight, Full