OFF MARKET

Off Market Dec 2017 for $265K

$534,353

•

1,104

sq ft

20 Winding Way, Portland, ME 04102

About this home

Move right in! Enjoy simple, single level living in this updated Rosemont ranch. Beautiful oak & tile floors, a new granite & stainless kitchen and the renovated bathroom mean you'll have plenty of time to walk to the nearby Portland Trails & explore. On chilly days, relax by the cozy fireplace while the new energy efficient windows & doors keep in the toasty warmth. With easy access to shopping, the Old Port & the airport, you'll see why this is one of Portland's most desirable neighborhoods.

Single-familyProperty Type

1956Year Built

7,840 sq ftLot Size

$484Est. Price/Sq.Ft.

1 spaceParking

Listed by Scott Townsend • Keller Williams Realty

Contact: scottandsunny@kw.com

Bought with Tiffany Hampton • EXP Realty

Redfin checked: 3 minutes ago

•Source:MREIS #1331198

Redfin Estimate

$534,353

$269K since sold in December 2017$10K since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 11.5% higher than the average sale price ($479K) of 6 comparable homes.

SOLD MAY 11, 2026
$645,000
A
3 beds1 bath1,092 sq ft
117 Colonial Rd, Portland, ME 04102
SOLD NOV 20, 2025
$495,000
B
3 beds1 bath1,230 sq ft
17 Sandy Ter, Portland, ME 04102
SOLD JUN 5, 2026
$462,000
C
3 beds1 bath1,159 sq ft
77 Dorset St, Portland, ME 04102
SOLD DEC 18, 2025
$458,000
D
3 beds1 bath1,040 sq ft
159 Bancroft St, Portland, ME 04102
SOLD OCT 27, 2025
$422,105
E
3 beds1 bath928 sq ft
131 Colonial Rd, Portland, ME 04102
SOLD AUG 14, 2026
$394,000
F
3 beds1.5 baths1,113 sq ft
62 Dorset St, Portland, ME 04102

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Earn from this home

Sell

$328,596

Est. take-home

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Rent

$1,811/mo

Redfin rental estimate

List your home for rent

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

OPEN THU, 2:30PM TO 4:30PM
$325,000
3 beds1.5 baths1,036 sq ft
65 Dougherty Ct #203, Portland, ME 04102
OPEN THU, 2:30PM TO 4:30PM
$268,800
1 bed1 bath512 sq ft
65 Dougherty Ct #101, Portland, ME 04102
$619,000
3 beds2 baths1,372 sq ft
56 Four Winds Rd, Portland, ME 04102
$525,000
3 beds1.5 baths2,024 sq ft
130 Capisic St, Portland, ME 04102
OPEN SEP 12, 11AM TO 1PM
$475,000
3 beds1.5 baths1,746 sq ft
37 Longwood Dr, Portland, ME 04102
$599,000
3 beds1.5 baths1,440 sq ft
29A Pine St, Portland, ME 04102
$445,000
3 beds1 bath1,230 sq ft
1363 Congress St #3, Portland, ME 04102
See all

Provided by Redfin

Sale history for 20 Winding Way

Date

Event

Price

MREIS #1331198

Dec 4, 2017

Sold

$265,000

$240/sq ft

Nov 2, 2017

Listed

$275,000

$249/sq ft

MREIS #1327164

Oct 13, 2017

Sold

$274,000

$248/sq ft

Oct 5, 2017

Price Changed

$289,000

$262/sq ft

Sep 23, 2017

Listed

$294,900

$267/sq ft

+29

Classic construction features such as oak floors, plaster walls and wood burning fireplace are highlighted by the thoughtful renovation of the kitchen, bath and cosmetic finishes. New kitchen cabinets, granite counter and stainless appliances are complimented by fresh new light fixtures and calming paint colors. Bath has all new fixtures, tile floor and new light fixtures. New windows, new front door and storm door will help keep the heat in and the cold out while you sit by the fire. Plus a 2 car garage!

Year

Property tax

Land + Additions

Assessment*

2024

$5,181 (+4.2%)

$81,200 + $264,000

$345,200

2023

$4,974 (+5.9%)

$81,200 + $264,000

$345,200

2022

$4,698 (+4.8%)

$81,200 + $264,000

$345,200

2021

$4,484 (+22.7%)

$81,200 + $264,000

$345,200

2020

$3,653

$58,300 + $98,400

$156,700

2019

$3,653 (+3.7%)

$58,300 + $98,400

$156,700

2018

$3,523 (+3.8%)

$58,300 + $98,400

$156,700

2017

$3,393 (+2.6%)

$58,300 + $98,400

$156,700

2016

$3,308 (+2.3%)

$58,300 + $98,400

$156,700

2015

$3,233 (+3.2%)

$58,300 + $98,400

$156,700

2014

$3,134

$58,300 + $98,400

$156,700

Tax history for 20 Winding Way

Year

Property tax

Land + Additions

Assessment*

2024

$5,181 (+4.2%)

$81,200 + $264,000

$345,200

2023

$4,974 (+5.9%)

$81,200 + $264,000

$345,200

2022

$4,698 (+4.8%)

$81,200 + $264,000

$345,200

2021

$4,484 (+22.7%)

$81,200 + $264,000

$345,200

2020

$3,653

$58,300 + $98,400

$156,700

2019

$3,653 (+3.7%)

$58,300 + $98,400

$156,700

2018

$3,523 (+3.8%)

$58,300 + $98,400

$156,700

2017

$3,393 (+2.6%)

$58,300 + $98,400

$156,700

2016

$3,308 (+2.3%)

$58,300 + $98,400

$156,700

2015

$3,233 (+3.2%)

$58,300 + $98,400

$156,700

2014

$3,134

$58,300 + $98,400

$156,700

*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

7,841 Sq. Ft.

Year renovated

—

Sq. Ft.

1,104

Year built

1956

Style

Single Family Residential

County

Cumberland County

APN

125046

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 27, 2026.

Property details

Parking

Parking Information
Has Garage
Parking Features: 1 - 4 Spaces, Paved, Detached
Vehicle Storage: 2 Car, Detached

Interior

Bathroom Information
# of Baths (Full): 1

Room 1 Information
Type: Living Room
Level: First
Features: Wood-Burning Fireplace

Room 2 Information
Type: Bedroom 1
Level: First
Features: Closet

Room 3 Information
Type: Dining Room
Level: First
Features: Formal

Room 4 Information
Type: Bedroom 2
Level: First
Features: Closet

Room 5 Information
Type: Kitchen
Level: First
Features: Eat-In Kitchen

Room 6 Information
Type: Bedroom 3
Level: First
Features: Closet

Basement Information
Basement Entry: Interior, Walk-Out Access, Full, Unfinished

Interior Features
# of Rooms: 6
Interior Features: 1st Floor Bedroom, Bathtub, One-Floor Living, Shower
Refrigerator, Microwave, Electric Range, Dishwasher
Flooring: Wood, Tile

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Exterior

Building Information
Construction Materials: Wood Siding, Vinyl Siding, Wood Frame
Foundation Details: Concrete Perimeter
Total Building Area (Sq. Ft.): 1,104
Building Area Source: Public Records

Property Information
Property Sub Type: Single Family Residence
Year Built: 1956
Above-Grade Finished Area (Sq. Ft.): 1,104

Lot Information
Lot Size (Sq. Ft.): $7,840.80
Lot Size (Acres): 0.18
Lot Size Source: Public Records
Lot Features: Well Landscaped, Rolling/Sloping, Open, Level, Intown, Near Shopping, Near Turnpike/Interstate, Neighborhood, Suburban, Near Public Transit
Road Surface Type: Paved
Zoning: R3

Financial

Tax Information
Annual Tax Amount: $3,393

Utilities

Utility Information
Has Heating
Heating: Hot Water, Forced Air, Baseboard
Electric: Circuit Breakers
Sewer: Public Sewer
Utilities: Utilities On
Utilities On: Yes
Water Source: Public
Water Heater: Off Heating System

Location

Location Information
Unparsed Address: 20 Winding Way, Portland, ME 04102
Directions: Capisic St to Starbird Rd to right on Winding Way

Public facts

Beds: 3
Baths: 1.0
Sq. Ft.: 1,104
Stories: 1.0
Lot Size: 7,841 square feet
Style: Single Family Residential
Year Built: 1956
Year Renovated: —
County: Cumberland County
APN: 125046

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

60% 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 • 04102

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

$508,000 – $615,000

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Nearby similar homes

$499,000

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FOR SALE BY OWNER

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New listings for sale in 04102

OPEN THU, 2:30PM TO 4:30PM

$325,000

3 beds1.5 baths1,036 sq ft

65 Dougherty Ct #203, Portland, ME 04102

OPEN THU, 2:30PM TO 4:30PM

$268,800

1 bed1 bath512 sq ft

65 Dougherty Ct #101, Portland, ME 04102

$619,000

3 beds2 baths1,372 sq ft

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$525,000

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130 Capisic St, Portland, ME 04102

OPEN SEP 12, 11AM TO 1PM

$475,000

3 beds1.5 baths1,746 sq ft

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3 beds1.5 baths1,440 sq ft

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Home values near 20 Winding Way

Data from public records.

Address	Redfin Estimate
7 Winding Way, Portland, ME 4 Beds \| 2 Baths \| 1764 Sq. Ft.	$577,386
19 Winding Way, Portland, ME 3 Beds \| 2 Baths \| 1104 Sq. Ft.	$542,777

Address	Redfin Estimate
28 Winding Way, Portland, ME 3 Beds \| 1 Baths \| 1152 Sq. Ft.	$503,438
35 Winding Way, Portland, ME 3 Beds \| 2 Baths \| 1764 Sq. Ft.	$608,279

Address	Redfin Estimate
31 Winding Way, Portland, ME 3 Beds \| 1 Baths \| 1328 Sq. Ft.	$570,500
27 Winding Way, Portland, ME 3 Beds \| 1.5 Baths \| 1008 Sq. Ft.	$508,801

Property information provided by MREIS when last listed in 2017. This data may not match . Learn more.

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