OFF MARKET

Off Market Jul 2019 for $405K

$693,845

•

2,406

sq ft

52 Winding Way, Portland, ME 04102

About this home

Charming and sophisticated in the quiet Rosemont location this five bedroom home offers a finished basement, craftroom, first floor bedroom, four bedrooms upstairs, brick fireplace, and is wired for ethernet. The gorgeous updated kitchen is complete with high end appliances and a lift shelf in the island. This beautiful city lot is convenient to downtown, portland trails, and new nearby school. So much to offer!

Single-familyProperty Type

1956Year Built

6,969 sq ftLot Size

$288Est. Price/Sq.Ft.

1 car garageParking

Listed by Payson Swan • Swan Real Estate

Bought with Stephanie Morrison • Morrison Real Estate

Redfin checked: 2 minutes ago

•Source:MREIS #1417158

Redfin Estimate

$693,845

$289K since sold in July 2019$9,000 since August

Recently sold homes
Estimate history
Homes for sale

This home's estimate is 6.8% higher than the average sale price ($650K) of 6 comparable homes.

SOLD MAY 15, 2026
$678,500
A
4 beds2 baths1,540 sq ft
10 Meadowbrook Ln, Portland, ME 04102
SOLD JUL 23, 2026
$820,000
B
4 beds1.5 baths2,235 sq ft
381 Ludlow St, Portland, ME 04102
SOLD JUL 17, 2026
$675,000
C
4 beds2 baths2,004 sq ft
76 Edwards St, Portland, ME 04102
SOLD JUN 8, 2026
$475,000
D
4 beds2 baths1,776 sq ft
15 Craigie St, Portland, ME 04102
SOLD JUN 30, 2026
$611,000
E
4 beds2 baths1,756 sq ft
17 Belfield St, Portland, ME 04103
SOLD JUL 7, 2026
$640,000
F
3 beds2 baths1,283 sq ft
11 Glen Haven Rd E, Portland, ME 04102

Claim this home to receive a free report every month with insights on the changing estimate.

Earn from this home

Sell

$374,934

Est. take-home

List your home with Redfin and save $6,938

Rent

$2,755/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 52 Winding Way

Year

Property tax

Land + Additions

Assessment*

2024

$7,368 (+4.2%)

$80,200 + $410,700

$490,900

2023

$7,074 (+5.9%)

$80,200 + $410,700

$490,900

2022

$6,681 (+4.8%)

$80,200 + $410,700

$490,900

2021

$6,377 (+15.4%)

$80,200 + $410,700

$490,900

2020

$5,524

$57,400 + $179,600

$237,000

2019

$5,524 (+8.2%)

$57,400 + $179,600

$237,000

2018

$5,107 (+3.8%)

$57,400 + $169,800

$227,200

2017

$4,919 (+2.6%)

$57,400 + $169,800

$227,200

2016

$4,796 (+2.3%)

$57,400 + $169,800

$227,200

2015

$4,687 (+3.1%)

$57,400 + $169,800

$227,200

2014

$4,544

$57,400 + $169,800

$227,200

Tax history for 52 Winding Way

Year

Property tax

Land + Additions

Assessment*

2024

$7,368 (+4.2%)

$80,200 + $410,700

$490,900

2023

$7,074 (+5.9%)

$80,200 + $410,700

$490,900

2022

$6,681 (+4.8%)

$80,200 + $410,700

$490,900

2021

$6,377 (+15.4%)

$80,200 + $410,700

$490,900

2020

$5,524

$57,400 + $179,600

$237,000

2019

$5,524 (+8.2%)

$57,400 + $179,600

$237,000

2018

$5,107 (+3.8%)

$57,400 + $169,800

$227,200

2017

$4,919 (+2.6%)

$57,400 + $169,800

$227,200

2016

$4,796 (+2.3%)

$57,400 + $169,800

$227,200

2015

$4,687 (+3.1%)

$57,400 + $169,800

$227,200

2014

$4,544

$57,400 + $169,800

$227,200

*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

7,405 Sq. Ft.

Year renovated

—

Sq. Ft.

1,998

Year built

1956

Style

Single Family Residential

County

Cumberland County

APN

125015

Parking Spaces

—

Basement

—

Accessible

—

HOA Dues

—

Garage

—

Features

—

Last updated by owner on Jul 27, 2026.

Property details

Parking

Parking Information
Has Garage
Attached Garage: Yes
# of Garage Spaces: 1
Parking Features: 1 - 4 Spaces, Paved
Vehicle Storage: 1 Car, Attached

Interior

Bathroom Information
# of Baths (Full): 2

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

Interior Features
# of Rooms: 9
Interior Features: 1st Floor Bedroom, Bathtub, Pantry, Shower
Washer, Refrigerator, Microwave, Dryer, Disposal, Dishwasher, Cooktop
Flooring: Wood, Tile
Other Equipment: Other Equipment, Internet Access Available

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

Fireplace Information
# of Fireplaces: 1
Has Fireplace

Exterior

Building Information
Construction Materials: Vinyl Siding, Wood Frame
Foundation Details: Concrete Perimeter
Roof: Shingle
Total Building Area (Sq. Ft.): 2,406
Building Area Source: Seller

Exterior Features
Patio & Porch Features: Deck

Property Information
Property Sub Type: Single Family Residence
Year Built: 1956
Above-Grade Finished Area (Sq. Ft.): 1,998
Below-Grade Finished Area (Sq. Ft.): 408
Green Energy Efficient: Other/See Internal Remarks

Lot Information
Lot Size (Sq. Ft.): $6,969.60
Lot Size (Acres): 0.16
Lot Size Source: Public Records
Lot Features: Open, Near Shopping, Neighborhood
Zoning: RES

Financial

Tax Information
Annual Tax Amount: $5,107
Tax Year: 2018

Utilities

Utility Information
Has Heating
Heating: Hot Water, Baseboard
Electric: Circuit Breakers
Sewer: Public Sewer
Water Source: Public
Water Heater: Off Heating System

Location

Location Information
Unparsed Address: 52 Winding Way, Portland, ME 04102
Directions: CAPISIC STREET TO LITTLE ROAD TO WINDING WAY

Public facts

Beds: 5
Baths: 2.0
Sq. Ft.: 1,998
Stories: 2.0
Lot Size: 7,405 square feet
Style: Single Family Residential
Year Built: 1956
Year Renovated: —
County: Cumberland County
APN: 125015

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

63% 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

$660,000 – $798,000

Reach more buyers when you sell with Redfin. Save up to $6,938 in fees. 3 minutes to get started.

Get a free, detailed breakdown of how we calculated your estimate.

Nearby similar homes

$386,460

3 beds1 bath656 sq ft

2 Firefly St #303, Portland, ME 04102

$499,000

3 beds1.5 baths1,318 sq ft

15 Rudman Rd, Portland, ME 04102

$735,000

3 beds1.5 baths1,861 sq ft

26 Adelaide St, Portland, ME 04103

OPEN SEP 12, 11AM TO 1PM

$475,000

3 beds1.5 baths1,746 sq ft

37 Longwood Dr, Portland, ME 04102

$655,000

3 beds2.5 baths2,066 sq ft

51 Old Mast Rd, Portland, ME 04102

OPEN SAT, 10AM TO 12PM

$625,000

4 beds2 baths1,680 sq ft

45 Runnells St, Portland, ME 04103

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

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

Home values near 52 Winding Way

Data from public records.

Address	Redfin Estimate
58 Winding Way, Portland, ME 4 Beds \| 1.5 Baths \| 1698 Sq. Ft.	$603,831
64 Winding Way, Portland, ME 3 Beds \| 1.5 Baths \| 1540 Sq. Ft.	$576,226

Address	Redfin Estimate
28 Winding Way, Portland, ME 3 Beds \| 1 Baths \| 1152 Sq. Ft.	$502,540
41 Winding Way, Portland, ME 2 Beds \| 1 Baths \| 1008 Sq. Ft.	$544,083

Address	Redfin Estimate
61 Winding Way, Portland, ME 3 Beds \| 2 Baths \| 1582 Sq. Ft.	$620,319
67 Winding Way, Portland, ME 3 Beds \| 2 Baths \| 1516 Sq. Ft.	$593,539

Property information provided by MREIS when last listed in 2019. This data may not match . Learn more.

More real estate resources

Zip Codes
Cities
Neighborhoods
Minor Civil Divisions
Popular Searches

04105 homes for sale
04106 homes for sale
04107 homes for sale
04074 homes for sale
04101 homes for sale

Download the Redfin App on the Apple App Store

Download the Redfin App from the Google Play Store

Join us

Become an Agent

Get referrals

Careers

Find homes faster

About us

Find us

Subsidiaries

Affiliated Business

Countries

United States

Canada

Updated September 2025: By searching, you agree to the Terms of Use, and Privacy Policy.

Do not sell or share my personal information.

REDFIN and all REDFIN variants, WALK SCORE, and the R logos, are trademarks of Redfin Corporation, registered or pending in the USPTO.

California DRE #01521930

Redfin is licensed to do business in New York as Redfin Real Estate. NY Standard Operating Procedures

New Mexico Real Estate Licenses

TREC: Info About Brokerage Services, Consumer Protection Notice

All mortgage lending products and information are provided by Rocket Mortgage, LLC | NMLS #3030; www.NMLSConsumerAccess.org. Licensed in 50 states. This site is not authorized by the New York State Department of Financial Services for mortgage solicitation or loan applications activities related to properties located in the State of New York.

Redfin Corporation is an affiliated business of Rocket Limited Partnership. Each company, and their subsidiaries, are separate legal entities operated and managed through its own management and governance structures.

If you are using a screen reader, or having trouble reading this website, please call Redfin Customer Support for help at 1-844-759-7732.

REDFIN IS COMMITTED TO AND ABIDES BY THE FAIR HOUSING ACT AND EQUAL OPPORTUNITY ACT. READ REDFIN'S FAIR HOUSING POLICY AND THE NEW YORK STATE FAIR HOUSING NOTICE.

GreatSchools Ratings provided by GreatSchools.org.

Wells homes for sale
Cumberland homes for sale
Buxton homes for sale
Sebago homes for sale
Harpswell homes for sale

Houses for rent in Portland	Agents near me	Cape Elizabeth, ME homes for sale	Portland Housing Market
Houses for sale near me	Portland, ME homes for sale	Bangor, ME homes for sale
Land for sale near me	Scarborough, ME homes for sale	Kittery, ME homes for sale
Open Houses near me	South Portland, ME homes for sale	Portland Property Records
Condos for sale near me	Falmouth, ME homes for sale	ME New Listings

Falmouth homes for sale
Scarborough homes for sale
Cape Elizabeth homes for sale