OFF MARKET

Off Market Apr 2018 for $305K

$548,194

•

707

sq ft

45 Winding Way, Portland, ME 04108

About this home

Come enjoy this near total renovation of a year-round cottage which was quite cute but now, even more so. Totally new & , moved kitchen first floor full bath is new while another full bath was added on the second floor. The 2 bedrooms are up with the master opening onto a two level deck which offers enough glimpses of "blue" to remind you that you're only about 250 yards from the rocky shore. Walkout (small) basement, insulation and vapor barriers added, In top condition with some furnishings!!

Single-familyProperty Type

1920Year Built

2,613 sq ftLot Size

$775Est. Price/Sq.Ft.

Listed by Raymond Goodhue Jr. • Port Island Realty

Bought with Theresa Folsom • Bean Group

Redfin checked: a minute ago

•Source:MREIS #1337662

Redfin Estimate

$548,194

$243K since sold in April 2018$21K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 4.4% higher than the average sale price ($525K) of 6 comparable homes.

SOLD AUG 14, 2026
$394,000
A
3 beds1.5 baths1,113 sq ft
62 Dorset St, Portland, ME 04102
SOLD MAY 8, 2026
$647,000
B
3 beds1.5 baths1,638 sq ft
36 Colonial Rd, Portland, ME 04102
BOUGHT WITH REDFIN JUN 22, 2026
$375,800
C
2 beds1 bath689 sq ft
24 Westminster Ave, Portland, ME 04103
SOLD MAY 5, 2026
$805,000
D
3 beds1.5 baths1,312 sq ft
40 Kenilworth St, Portland, ME 04102
SOLD AUG 21, 2026
$540,000
E
3 beds2 baths1,390 sq ft
84 Dorset St, Portland, ME 04102
SOLD AUG 27, 2026
$390,000
F
3 beds1 bath1,043 sq ft
38 Lucas St, Portland, ME 04102

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Earn from this home

Sell

$312,643

Est. take-home

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Rent

$2,125/mo

Redfin rental estimate

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Market trends in 04102, ME

Last updated August 2026

Buyer's Market

Seller's Market

Seller's market

Sale-to-List Price

101.1%

+0.2% MoM

Median sale price

$642K

$42K MoM

Avg. days on market

31d

4 days MoM

Recently sold homes

5 MoM

New listings for sale

FOR SALE BY OWNER
$719,000
3 beds2 baths1,250 sq ft
248 Pleasant Ave, Portland, ME 04108
See all

Provided by Redfin

Sale history for 45 Winding Way

Year

Property tax

Land + Additions

Assessment*

2024

$5,136 (+4.2%)

$165,300 + $176,900

$342,200

2023

$4,931 (+5.9%)

$165,300 + $176,900

$342,200

2022

$4,657 (+4.8%)

$165,300 + $176,900

$342,200

2021

$4,445 (−12.3%)

$165,300 + $176,900

$342,200

2020

$5,070

$125,900 + $91,600

$217,500

2019

$5,070 (+3.7%)

$125,900 + $91,600

$217,500

2018

$4,889 (+3.8%)

$125,900 + $91,600

$217,500

2017

$4,709 (+2.6%)

$125,900 + $91,600

$217,500

2016

$4,591 (+2.3%)

$125,900 + $91,600

$217,500

2015

$4,487 (+3.1%)

$125,900 + $91,600

$217,500

2014

$4,350

$125,900 + $91,600

$217,500

Tax history for 45 Winding Way

Year

Property tax

Land + Additions

Assessment*

2024

$5,136 (+4.2%)

$165,300 + $176,900

$342,200

2023

$4,931 (+5.9%)

$165,300 + $176,900

$342,200

2022

$4,657 (+4.8%)

$165,300 + $176,900

$342,200

2021

$4,445 (−12.3%)

$165,300 + $176,900

$342,200

2020

$5,070

$125,900 + $91,600

$217,500

2019

$5,070 (+3.7%)

$125,900 + $91,600

$217,500

2018

$4,889 (+3.8%)

$125,900 + $91,600

$217,500

2017

$4,709 (+2.6%)

$125,900 + $91,600

$217,500

2016

$4,591 (+2.3%)

$125,900 + $91,600

$217,500

2015

$4,487 (+3.1%)

$125,900 + $91,600

$217,500

2014

$4,350

$125,900 + $91,600

$217,500

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

Public record

Beds

Baths

Stories

Lot width

—

Lot depth

—

Lot size

2,614 Sq. Ft.

Year renovated

—

Sq. Ft.

707

Year built

1920

Style

Single Family Residential

County

Cumberland County

APN

116864

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 27, 2026.

Property details

Interior

Bathroom Information
# of Baths (Full): 2

Basement Information
Basement Entry: Walk-Out Access

Interior Features
# of Rooms: 4
Flooring: Wood

Exterior

Building Information
Construction Materials: Vinyl Siding, Clapboard, Wood Frame
Roof: Shingle
Total Building Area (Sq. Ft.): 707
Building Area Source: Public Records

Property Information
Property Sub Type: Single Family Residence
Year Built: 1920
Above-Grade Finished Area (Sq. Ft.): 707

Lot Information
Lot Size (Sq. Ft.): $2,613.60
Lot Size (Acres): 0.06
Lot Size Source: Public Records
Lot Features: Rural
Road Surface Type: Gravel, Dirt, Paved
Zoning: IR-2

Waterfront Information
Water Body Name: Atlantic Ocean
Water Body Type: Ocean
Water View: Seasonal

Financial

Tax Information
Annual Tax Amount: $4,709

Utilities

Utility Information
Has Heating
Heating: Stove, Direct Vent Heater
Electric: Circuit Breakers
Sewer: Public Sewer
Utilities On: No
Water Source: Public
Water Heater: Electric

Location

Location Information
Unparsed Address: 45 Winding Way, Portland, ME 04108
Directions: Casco Bay Lines to Peaks Island. Right off Welch to Island. Turn right onto Whitehead to Seashore Follow Seashore turning left onto Great Pond Rd. Go to end, turn right onto Winding Way, Winding Way House is 3rd on right.

Public facts

Beds: 2
Baths: 2.0
Sq. Ft.: 707
Stories: 2.0
Lot Size: 2,614 square feet
Style: Single Family Residential
Year Built: 1920
Year Renovated: —
County: Cumberland County
APN: 116864

Home facts updated by county records on Jul 27, 2026

Around this home

Schools

Amanda C Rowe School

Public PreK-5 • Assigned • 0.8mi

4/10

Lincoln Middle School

Public 6-8 • Assigned • 1.0mi

6/10

Deering High School

Public 9-12 • Assigned • 0.9mi

2/10

Provided by GreatSchools

Lifestyle

Provided by Walk Score and Local Logic

Climate risks

1/10 Flood Factor

Minimal risk of a flood reaching the building in the next 30 years

1/10 Fire Factor

Unlikely to be in a wildfire in next 30 years

4/10 Heat Factor

7 days above 89° expected this year, 16 days in 30 years

6/10 Wind Factor

64% chance of strong winds in next 30 years

2/10 Air Factor

1 unhealthy days expected this year, 1 days in 30 years

Provided by First Street

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 8.4 hours in June and 4.2 hours in December, placing it below the U.S. average for solar exposure.

8.4 hrs

4.2 hrs

JuneDecember

Provided by Shadowmap

Estimated sale price

$521,000 – $631,000

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Nearby similar homes

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FOR SALE BY OWNER

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3D WALKTHROUGH

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New listings for sale in 04108

FOR SALE BY OWNER

$719,000

3 beds2 baths1,250 sq ft

248 Pleasant Ave, Portland, ME 04108

Home values near 45 Winding Way

Data from public records.

Address	Redfin Estimate
58 Winding Way, Portland, ME 4 Beds \| 1.5 Baths \| 1698 Sq. Ft.	$614,683
52 Winding Way, Portland, ME 5 Beds \| 2 Baths \| 2406 Sq. Ft.	$703,733

Address	Redfin Estimate
28 Winding Way, Portland, ME 3 Beds \| 1 Baths \| 1152 Sq. Ft.	$516,737
64 Winding Way, Portland, ME 3 Beds \| 1.5 Baths \| 1540 Sq. Ft.	$612,890

Address	Redfin Estimate
61 Winding Way, Portland, ME 3 Beds \| 2 Baths \| 1582 Sq. Ft.	$636,329
31 Winding Way, Portland, ME 3 Beds \| 1 Baths \| 1328 Sq. Ft.	$577,586

Property information provided by MREIS when last listed in 2018. This data may not match . Learn more.

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