OFF MARKET

Off market jun 2021 for $1M

$1,272,989

•

2,468

sq ft

59 Winding Way, Portland, ME 04108

About this home

Single-familyProperty Type

1900Year Built

0.5 acresLot Size

$516Est. Price/Sq.Ft.

1 spaceParking

Listed by Ralph Ashmore • Ashmore Realty

Bought with Alyce Bauerle • Port Island Realty

Redfin checked: 2 minutes ago

•Source:MREIS #1486476

Redfin Estimate

$1,272,989

$248K since sold in June 2021$1,000 since September

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 9.7% higher than the average sale price ($1.16M) of 6 comparable homes.

SOLD SEP 16, 2026
$1,429,000
A
3 beds2 baths1,722 sq ft
17 3rd St, Portland, ME 04108
SOLD AUG 6, 2026
$1,479,000
B
4 beds2.5 baths2,110 sq ft
6 Sea View Ave, Cape Elizabeth, ME 04107
SOLD SEP 9, 2026
$1,000,000
C
4 beds1.5 baths1,882 sq ft
72 Stonybrook Rd, Cape Elizabeth, ME 04107
SOLD APR 20, 2026
$1,475,000
D
4 beds2 baths1,540 sq ft
15 Myrtle Ave, South Portland, ME 04106
SOLD SEP 8, 2026
$612,000
E
4 beds2 baths1,803 sq ft
24 Central Ave, Portland, ME 04108
SOLD OCT 2, 2026
$965,000
F
4 beds2 baths1,546 sq ft
32 Rocky Hill Rd, Cape Elizabeth, ME 04107

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Earn from this home

Sell

$463,835

Est. take-home

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Rent

$3,375/mo

Redfin rental estimate

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Market trends in 04108, ME

Last updated September 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

95.6%

0.4% MoM

Median sale price

$660K

$63K MoM

Avg. days on market

71d

16 days MoM

Recently sold homes

1 MoM

Provided by Redfin

Sale history for 59 Winding Way

Year

Property tax

Land + Additions

Assessment*

2024

$11,091 (+4.2%)

$317,900 + $421,000

$738,900

2023

$10,648 (+6.8%)

$317,900 + $421,000

$738,900

2022

$9,973 (+16.5%)

$317,900 + $414,900

$732,800

2021

$8,557 (−27.3%)

$317,900 + $340,800

$658,700

2020

$11,774

$377,400 + $127,700

$505,100

2019

$11,774 (+3.7%)

$377,400 + $127,700

$505,100

2018

$11,355 (+3.8%)

$377,400 + $127,700

$505,100

2017

$10,935 (+2.6%)

$377,400 + $127,700

$505,100

2016

$10,663 (+2.3%)

$377,400 + $127,700

$505,100

2015

$10,420 (+3.1%)

$377,400 + $127,700

$505,100

2014

$10,102

$377,400 + $127,700

$505,100

Tax history for 59 Winding Way

Year

Property tax

Land + Additions

Assessment*

2024

$11,091 (+4.2%)

$317,900 + $421,000

$738,900

2023

$10,648 (+6.8%)

$317,900 + $421,000

$738,900

2022

$9,973 (+16.5%)

$317,900 + $414,900

$732,800

2021

$8,557 (−27.3%)

$317,900 + $340,800

$658,700

2020

$11,774

$377,400 + $127,700

$505,100

2019

$11,774 (+3.7%)

$377,400 + $127,700

$505,100

2018

$11,355 (+3.8%)

$377,400 + $127,700

$505,100

2017

$10,935 (+2.6%)

$377,400 + $127,700

$505,100

2016

$10,663 (+2.3%)

$377,400 + $127,700

$505,100

2015

$10,420 (+3.1%)

$377,400 + $127,700

$505,100

2014

$10,102

$377,400 + $127,700

$505,100

*Taxable value of land and structures on it ("additions") is determined regularly by local assessors and does not affect market price.

Public record

Public record
Permits

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

0.5 Acres

Year renovated

—

Sq. Ft.

2,468

Year built

1900

Style

Single Family Residential

County

Cumberland County

APN

116879

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 27, 2026.

Property details

Parking

Parking Information
Parking Features: 1 - 4 Spaces, Gravel

Interior

Bathroom Information
# of Baths (Full): 2

Room 1 Information
Type: Laundry
Level: First

Room 2 Information
Type: Bedroom 2
Level: Second

Room 3 Information
Type: Dining Room
Level: First

Room 4 Information
Type: Kitchen
Level: First

Room 5 Information
Type: Bedroom 3
Level: Second

Room 6 Information
Type: Bedroom 4
Level: Second

Room 7 Information
Type: Living Room
Level: First

Room 8 Information
Type: Bedroom 1
Level: First

Basement Information
Basement Entry: Crawl Space, Exterior Only

Interior Features
# of Rooms: 8
Interior Features: 1st Floor Bedroom
Flooring: Wood, Tile, Brick

Laundry Information
Laundry Features: 1st Floor Laundry, Main Level

Exterior

Building Information
Construction Materials: Shingle Siding, Wood Frame
Foundation Details: Pillar/Post/Pier
Total Building Area (Sq. Ft.): 2,468
Building Area Source: Public Records

Exterior Features
Patio & Porch Features: Deck
Other Structures: Outbuilding, Shed(s)

Property Information
Property Sub Type: Single Family Residence
Year Built: 1900
Above-Grade Finished Area (Sq. Ft.): 2,468

Lot Information
Lot Size (Sq. Ft.): $21,780
Lot Size (Acres): 0.5
Lot Size Source: Public Records
Lot Features: Rolling/Sloping, Near Golf Course, Near Public Beach, Near Public Transit
Road Surface Type: Gravel, Dirt
Zoning: IR-1

Waterfront Information
Island: Yes
Water Body Name: Atlantic Ocean
Water Body Type: Ocean
Water View: Yes

Financial

Tax Information
Annual Tax Amount: $11,218
Tax Year: 2021

Utilities

Utility Information
Has Heating
Heating: Stove, Space Heater, Heat Pump
Has Cooling
Cooling: Wall/Window Unit(s), Heat Pump
Electric: Photovoltaics Seller Owned, Circuit Breakers
Sewer: Public Sewer
Water Source: Public
Water Heater: Electric, Tank

Location

Location Information
Unparsed Address: 59 Winding Way, Portland, ME 04108

Public facts

Beds: 4
Baths: 2.0
Sq. Ft.: 2,468
Stories: 2.0
Lot Size: 0.5 acres
Style: Single Family Residential
Year Built: 1900
Year Renovated: —
County: Cumberland County
APN: 116879

Home facts updated by county records on Jul 27, 2026

Around this home

Schools

Peaks Island School

Public PreK-5 • Assigned • 0.7mi

8/10

Deering High School

Public 9-12 • Assigned • 5.6mi

2/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Historical weather

Portland, ME • 04108

Average low and high temperatures (°F)

Jan

Feb

Mar

Apr

May

Jun

Jul

Aug

Sep

Oct

Nov

Dec

Sun exposure

In this area, properties receive around 8.5 hours in June and 4.3 hours in December, placing it below the U.S. average for solar exposure.

8.5 hrs

4.3 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$1.21M – $1.46M

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Nearby similar homes

$495,000

1 bed1 bath624 sq ft

12 Stone Dr, South Portland, ME 04106

$819,000

3 beds2.5 baths1,573 sq ft

50 Myrtle St, Portland, ME 04101

$879,999

2 beds1 bath716 sq ft

494 Island Ave, Portland, ME 04108

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$3,450,000

3 beds2 baths2,148 sq ft

2 Drew Rd, South Portland, ME 04106

$899,500

5 beds2 baths2,778 sq ft

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$1,080,000

3 beds2 baths1,720 sq ft

364 Island Ave, Portland, ME 04108

Home values near 59 Winding Way

Data from public records.

Address	Redfin Estimate
46 Winding Way, Portland, ME 1 Beds \| 1 Baths \| 864 Sq. Ft.	$472,903
46 Winding Way, Peaks Island, ME 1 Beds \| 1 Baths \| 864 Sq. Ft.	$510,977

Address	Redfin Estimate
68 Winding Way, Portland, ME 3 Beds \| 2.5 Baths \| 1298 Sq. Ft.	$887,310
73 Winding Way, Peaks Island, ME 3 Beds \| 2 Baths \| 1008 Sq. Ft.	$614,542

Address	Redfin Estimate
68 Winding Way, Peaks Island, ME 3 Beds \| 2.5 Baths \| 1298 Sq. Ft.	$1,197,333
33 Great Pond Road, Portland, ME 3 Beds \| 2 Baths \| 1147 Sq. Ft.	$689,411

Property information provided by MREIS when last listed in 2021. This data may not match . Learn more.

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