52 Winding Way

Closed 7/17/19
Closed 7/17/19
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Last Sold Price
$405,000
5 beds2,406 sqft$168/sqft
52 Winding Way, Portland, ME 04102

Description

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!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!
LISTING CLOSED: 07/17/2019 12:00 AM

  1. Listed by Payson Swan • Swan Real Estate
    P: (207) 415-8140 C: (207) 415-8140 pswanrealestate@gmail.com

Property Details for 52 Winding Way

Status
Closed
MLS #
1417158
Days on Market
3
Taxes
$5,107 / year
HOA Fees
-
Condo/Co-op Fees
-
Property Type
Single Family
MLS Type
Residential / Single Family Residence
Year Built
1956
Lot Size
0.16 AC / 6,969 SF
County
Cumberland County
Architectural Style
Garrison
Style
Garrison
Has Waterfront
No
Zoning
RES

Recent comparable sales

Median sold price

$490,000

Avg days on market

25

Sale-to-list ratio

96.8%

Portland, ME

9 comparable properties found

$430,000 | 21 Drake Street, Portland, ME 04103
1/48
1

$430,000

Sold 09/16/25

5
Bedrooms
1,984
Square Feet
0.53
Acres

21 Drake Street, Portland, ME 04103

$490,000 | 244 Ray Street, Portland, ME 04103
1/43
2

$490,000

Sold 10/31/25

5
Bedrooms
2,256
Square Feet
0.26
Acres

244 Ray Street, Portland, ME 04103

$520,000 | 47 Fall Brook Street, Portland, ME 04103
1/42
3

$520,000

Sold 12/23/25

5
Bedrooms
2,137
Square Feet
0.19
Acres

47 Fall Brook Street, Portland, ME 04103

$1,135,000 | 39 Lawn Avenue, Portland, ME 04103
1/57
4

$1,135,000

Sold 12/03/24

5
Bedrooms
2,404
Square Feet
0.12
Acres

39 Lawn Avenue, Portland, ME 04103

$489,000 | 186 Lane Avenue, Portland, ME 04103
1/52
5

$489,000

Sold 05/16/25

5
Bedrooms
1,970
Square Feet
0.18
Acres

186 Lane Avenue, Portland, ME 04103

$458,200 | 1670 Forest Avenue, Portland, ME 04103
1/36
6

$458,200

Sold 10/06/25

5
Bedrooms
1,478
Square Feet
0.15
Acres

1670 Forest Avenue, Portland, ME 04103

$416,000 | 71 Chesley Avenue, Portland, ME 04103
1/12
7

$416,000

Sold 12/13/24

4
Bedrooms
2,200
Square Feet
0.18
Acres

71 Chesley Avenue, Portland, ME 04103

$879,000 | 314 Stevens Avenue, Portland, ME 04103
1/6
8

$879,000

Sold 04/28/25

5
Bedrooms
2,400
Square Feet
0.1
Acres

314 Stevens Avenue, Portland, ME 04103

$514,500 | 1479 Washington Avenue, Portland, ME 04103
1/49
9

$514,500

Sold 07/03/25

5
Bedrooms
2,312
Square Feet
0.2
Acres

1479 Washington Avenue, Portland, ME 04103

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Location

Listing Courtesy of Swan Real Estate

Sold By Morrison Real Estate

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Building Information for 52 Winding Way

Stories-Year Built1956Building Size-Lot Size0.16 AC / 6,969 SF

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$2,484 per month

30 year fixed, 6.55% Interest

Principal and Interest

$2,059

Property Taxes

$426

HOA Dues

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Property Information for 52 Winding Way

Summary
Location and General Information
  • Location: Near Shopping, Neighborhood
  • Page: 154
  • Zoning Overlay: No
  • Directions: CAPISIC STREET TO LITTLE ROAD TO WINDING WAY
  • Latitude: 43.66754
  • Longitude: -$70.31
  • Transportation: Near Airport
Taxes and HOA
  • Association: No
  • Parcel Number: PTLD-000225-000000-C016001
  • Tax Lot: 16
  • Tax Book Number: 13303
  • Tax Map Number: 225-C
  • Tax Year: 2018
  • Tax Annual Amount: $5,107.00
Parking
  • Parking Features: 1 - 4 Spaces, Paved
  • Parking: 1 - 4 Spaces
  • Vehicle Storage: 1 Car, Attached
  • Has Attached Garage: Yes
  • Garage Spaces: 1.0
  • Has Garage: Yes
Property
Lot Information
  • Lot Features: Open, Near Shopping, Neighborhood
  • Lot Size Acres: 0.16
  • Lot Size Area: 0.16
  • Lot Size Source: Public Records
  • Lot Size Square Feet: 6969.6
  • Lot Size Units: Acres
  • Roads: Public
  • Site: Open
Property and Assessments
  • Above Grade Finished Area: 1998.0
  • Below Grade Finished Area: 408.0
  • Building Area Source: Seller
  • Building Area Total: 2406.0
  • Property Sub Type: Single Family Residence
  • Property Type: Residential
  • Construction: Wood Frame
  • Year Built: 1956
Building Features
  • Foundation Details: Concrete Perimeter
  • Foundation Materials: Poured Concrete
  • Construction Materials: Vinyl Siding, Wood Frame
Financial Information
  • List Price/SqFt: $199.70
Green Features
  • Energy Efficiency: Ceiling Fans, Other/See Internal Remarks
  • Green Energy Efficient: Other/See Internal Remarks
  • HERS Certified: No
Utilities
  • Heat Fuel: Oil, Pellets
  • Electric: Circuit Breakers
  • Gas: No Gas
  • Recreational Water: Nearby
  • Sewer: Public Sewer
  • Water Source: Public
  • Water Heater: Off Heating System
Interior and Exterior Features
Exterior Features
  • Exterior: Vinyl Siding
  • Roof: Shingle
  • Driveway: Paved
Interior Features
  • Amenities: 1st Floor Bedroom, Bathtub, Laundry - 1st Floor, Pantry, Shower
  • Appliances: Washer, Refrigerator, Microwave, Dryer, Disposal, Dishwasher, Cooktop
  • Appliances Included: Cooktop, Dishwasher, Disposal, Dryer, Microwave, Refrigerator, Washer
  • Bathrooms Full: 2
  • Bathrooms Total Decimal: 2.0
  • Bathrooms Total Integer: 2
  • Bedrooms Total: 5
  • Equipment: Other Equipment, Internet Access Available
  • Fireplaces Total: 1
  • Laundry Features: Laundry - 1st Floor, Main Level
  • Other Equipment: Other Equipment, Internet Access Available
  • # Full Baths Level 1: 1
  • # Full Baths Level 2: 1
  • Rooms Total: 9
  • Basement: Interior, Walk-Out Access, Finished, Full
  • Basement: Walk-Out Access, Finished, Full
  • Basement Entry: Interior
  • Has Fireplace: Yes
  • Patio And Porch Features: Deck
  • Has Cooling: No
  • Heating: Hot Water, Baseboard
  • Has Heating: Yes
  • Flooring: Wood, Tile
  • Interior Features: 1st Floor Bedroom, Bathtub, Pantry, Shower
Room Information
Laundry
  • Laundry Room Amenities: Laundry - 1st Floor, Main Level
Rental
Rent Information
  • Land Lease: No

Property History for 52 Winding Way

DateEvent & SourcePriceAppreciation
Jul 17, 2019

Sold

Maine Listings #1417158

$405,000—
Jun 4, 2019

Pending

Maine Listings #1417158

—
May 31, 2019

Listed (Active)

Maine Listings #1417158

$399,000—
DateEvent & SourcePrice
07/17/2019

Sold

Maine Listings #1417158

$405,000
06/04/2019

Pending

Maine Listings #1417158

—
05/31/2019

Listed (Active)

Maine Listings #1417158

$399,000

For completeness, we often displays two records for one sale: the MLS record and the public record.

Public Records for 52 Winding Way

Taxable ValueLand$132,400Additions$550,600Total$683,000
Tax Record2025$8,182 ($682 / month)
Home Facts
Beds5Baths2.5Total Finished SqFt1,998 SqFtAbove Grade Finished SqFt1,998 SqFtStories2Lot Size7,192 SqFtStyleSingle Family ResidenceYear Built1956Year Renovated1956CountyCUMBERLANDAPNPTLD M:225 B:C016001

Schools near 52 Winding Way

This home is within Portland Public Schools.
Rating
School
Type
Grades
Distance
Amanda C Rowe School
Public - PK to 5
Lincoln Middle School
Public - 6 to 8
Deering High School
Public - 9 to 12
Casco Bay High School
Public - 9 to 12
Rating
School
Distance
Amanda C Rowe School
PublicPK to 5

Lincoln Middle School
Public6 to 8

Deering High School
Public9 to 12

Casco Bay High School
Public9 to 12

School ratings and boundaries are provided by GreatSchools.org and Pitney Bowes. This information should only be used as a reference. Proximity or boundaries shown here are not a guarantee of enrollment. Please reach out to schools directly to verify all information and enrollment eligibility.

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Nearby home values

AddressSold priceBedsBathsSqftLot (Sqft)
This home: 52 Winding Way, Portland, ME 04102
$405,000
5
2,406
6,969
22 Meadowbrook Lane, Portland, ME 04102
$650,000
3
2.5
1,520
7,680
58 Winding Way, Portland, ME 04102
–
4
1.5
1,698
9,801
23 Meadowbrook Lane, Portland, ME 04102
$397,900
4
1,822
6,969
64 Winding Way, Portland, ME 04102
$305,000
3
1,540
9,583
45 Winding Way, Portland, ME 04102
–
2
2
707
2,714

Explore Nearby Homes

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Listing Courtesy of Swan Real Estate

Listing data is derived in whole or in part from the Maine IDX and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified. © 2026 Maine Real Estate Information System, Inc. All Rights Reserved.