Estimated Value: $1,194,000 - $2,191,000
This home is located at 59 Winding Way, Portland, ME 04106 since 04 April 2021 and is currently estimated at $1,498,880, approximately $607 per square foot. This property was built in 1900. 59 Winding Way is a home located in Cumberland County with nearby schools including Dyer Elementary School, South Portland High School, and Greater Portland Christian School.
Home Type
Est. Annual Taxes
Year Built
Lot Details
Parking
Property Views
Home Design
Interior Spaces
Flooring
Bedrooms and Bathrooms
Laundry
Basement
Eco-Friendly Details
Outdoor Features
Location
Utilities
Listing and Financial Details
Overview
Recreation
$1,250,000
Discover 139 Newbury Street, a stunning Victorian townhouse in the heart of Portland's most sought-after neighborhood. This historic gem offers endless potential and ample off-street parking (4+ spots). Currently set up as a first-floor office space with preserved architectural details and a spacious two-story apartment unit that's perfect for a live-work setup or could easily be transformed into
David Banks RE/MAX By The Bay
$1,500,000
Discover the perfect blend of historic charm and modern sophistication in this beautifully renovated 1840s townhouse, ideally located in the heart of Portland. This spacious two-unit property spans 2,400 square feet of thoughtfully designed living space, offering unparalleled versatility for investors or multi-generational living. With 4 bedrooms, 3.5 bathrooms, and a private backyard, this home
Jonathon Stinson Keller Williams Realty
$1,295,000
Originally built in 1880 and known as the William H. McDuffie House, this residence stands as a beautifully preserved piece of neighborhood history — and one of its most admired homes. A meticulous restoration blends historic bones with modern, elevated design at every turn. This 3 bedroom, 2.5 bath gem has been cared for with a level of detail that's hard to describe — but easy to feel the
David Banks RE/MAX By The Bay
$1,200,000
Exquisite West End condo, in a coveted brick building designed by John Calvin Stevens. Two bedrooms, each with en-suite bathroom, plus a den with custom built-ins. The spacious primary bedroom is a private retreat, with a lovely sitting area, a marble-lined bathroom and built-in storage closets. Formal living and dining rooms are distinguished by beautifully crafted built-ins and large windows,
Whitney Harvey Town & Shore Real Estate
$1,350,000
This exquisite home is truly the perfect blend of charm & history with modern amenities. Nestled in the heart of Portland's coveted West End. This 3 story historic row house boasts soaring ceilings on all three levels, a fully renovated kitchen with gorgeous quartz and quartzite countertops, custom cabinets, an enormous custom built island, and a Wolf range ideal for the aspiring home chef. This
Rachel Davey Vitalius Real Estate Group, LLC
$1,499,900
An exceptional and nearly unheard-of opportunity in one of the most desirable areas of the city of Portland. Situated on just over 0.75 acres, this property at 1905 Congress Street offers immense potential for investors, developers, or those looking to renovate and hold.Located in a quiet residential area, yet only minutes from the airport, I-95, and major retail corridors, the property features
Kenny Greene Real Broker
$1,295,000
This stunning shingle-style Queen Anne Victorian, built over 125 years ago in what was once Fessenden Park - a historic suburb and trolley stop from downtown Portland - has been beautifully modernized while preserving its timeless charm.A gracious front porch welcomes you with glimpses of the setting sun and invites you to relax and enjoy the quiet, one-way, tree-lined street lined with
Tom Landry Benchmark Real Estate
$1,195,000
You will fall in love with this iconic classic home in Deering Highlands. Home has not been offered for over 50 years and has been meticulously maintained. As you approach the home you will notice the exceptional professional landscaping including stone walls and established plantings. The large private rear yard has plenty of room for gardening or large gatherings. Step inside and you will be
John Hatcher Keller Williams Realty
$1,595,000
Nestled into a quiet, tree-lined street within Portland's coveted Deering Highlands, this meticulously-maintained arts and crafts style home with modern updates and fine finishes offers the perfect blend of historic charm, modern sophistication, serenity, and connectivity. Just footsteps from miles of trails, abundant green space, schools, universities, music and theater venues, and some of
Heather Shields Legacy Properties Sotheby's International Realty
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| Stevenson Charles I | -- | New England Title |
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Open | Stevenson Charles | $500,000 | |
| Previous Owner | Legere Thomas M | $251,500 |
| Date | Event | Price | Change | Sq Ft Price |
|---|---|---|---|---|
| 06/10/2021 06/10/21 | Sold | $1,025,000 | +2.3% | $415 / Sq Ft |
| 04/05/2021 04/05/21 | Pending | -- | -- | -- |
| 04/04/2021 04/04/21 | For Sale | $1,002,000 | -- | $406 / Sq Ft |
| Year | Tax Paid | Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. | Land | Improvement |
|---|---|---|---|---|
| 2024 | $11,091 | $738,900 | $317,900 | $421,000 |
| 2023 | $10,648 | $738,900 | $317,900 | $421,000 |
| 2022 | $9,973 | $732,800 | $317,900 | $414,900 |
| 2021 | $8,557 | $658,700 | $317,900 | $340,800 |
| 2020 | $11,774 | $505,100 | $377,400 | $127,700 |
| 2019 | $11,774 | $505,100 | $377,400 | $127,700 |
| 2018 | $10,406 | $505,100 | $377,400 | $127,700 |
| 2017 | $10,935 | $505,100 | $377,400 | $127,700 |
| 2016 | $10,663 | $505,100 | $377,400 | $127,700 |
| 2015 | $10,420 | $505,100 | $377,400 | $127,700 |
| 2014 | $10,102 | $505,100 | $377,400 | $127,700 |
R
Seller's Agent in 2021
Ralph Ashmore
Ashmore Realty
(207) 766-2981
1 in this area
7 Total Sales
A
Buyer's Agent in 2021
Alyce Bauerle
Portside Real Estate Group
(207) 332-4476
1 in this area
17 Total Sales
Source: Maine Listings
MLS Number: 1486476
APN: PTLD-000085-000000-S007001
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
Listing data is derived in whole or in part from Maine Real Estate Information System, Inc. (d/b/a Maine Listings) and is for consumers' personal, noncommercial use only. Dimensions are approximate and not guaranteed. All data should be independently verified.
© 2025 Maine Real Estate Information System, Inc. All Rights Reserved. Equal Housing Opportunity.
Homes.com, LLC, 17600 Laguna Canyon Rd Irvine, CA 92618 (888)-952-6393
