This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
$765,000
This is a carousel with tiles that activate property listing cards. Use the previous and next buttons to navigate.
1/1
Property Description
Welcome to this well-maintained Colonial nestled in Scarborough's Pleasant Hill neighborhood. Set on a beautifully landscaped lot with a spacious front yard, this home offers a comfortable blend of indoor and outdoor living spaces designed for everyday enjoyment and entertaining. Inside, you'll find a thoughtful layout featuring a welcoming living room with a fireplace, a formal dining room, and an additional sitting room that provides flexibility for a variety of uses. The screened-in sun porch creates the perfect spot to enjoy warm-weather evenings, while the back deck overlooks the yard and offers additional space for gatherings, outdoor dining, or simply relaxing. Upstairs, the primary bedroom includes an en suite bathroom, complemented by three additional bedrooms and a full bath. The partially finished basement adds valuable bonus space that can adapt to your needs, whether for hobbies, recreation, a home office, or storage. Additional features include a two-car garage and generator hookup for added convenience and peace of mind. Ideally located near Pleasant Hill Preserve's miles of trails and natural surroundings, this home also offers easy access to local beaches, including Higgins Beach, just a short drive away. Enjoy the convenience of nearby shopping, dining, commuter routes, and all that Scarborough's coastal community has to offer while returning home to a peaceful neighborhood setting.
Full Property Details
Full Property Details for 5 Winding Way
General
- Sold For: $765,000
- HOA FEE: $35/month
- HOA FEE FREQ.: Annually
- Taxes: $8,386 (25)
- Status: Closed
- Type: Single Family
- Source: MREIS
- MLS ID: 1667679
- Added to Site: 55 day(s) ago
Interior
- Number of Rooms: 9
- Interior Features: Primary Bedroom w/Bath
- Fireplace: Yes
- Number of Fireplaces: 1
- Appliances: Dishwasher, Dryer, Microwave, Electric Range, Refrigerator, Washer
- Flooring: Carpet, Tile, Wood
Rooms
Bathrooms
- Total Bathrooms: 3
- Full Bathrooms: 2
- Half Bathrooms: 1
Bedrooms
- Total Bedrooms: 4
Other Rooms
- Laundry: Main Level
Additional Information
- Equipment: Air Radon Mitigation System
Exterior
- Porch/Patio/Deck: Deck, Porch-Screened
Parking
- Garage: Yes
- Attached garage: Yes
- Garage Spaces: 2
- Parking Features: Paved, 1 - 4 Spaces
Location
- County: Cumberland
Community
- Association: Yes
Heating & Cooling
- Cooling Type: None
- Heating Type: Oil, Wood, Baseboard, Hot Water
Utilities
- Sewer: Quasi-Public
- Water: Public
Structural Information
- Architectural Style: Colonial
- Construction: Wood Frame, Clapboard
- Basement: Yes
- Basement Desc.: Bulkhead, Interior Entry, Finished, Partial, Unfinished
- Roof: Shingle
- Square Feet: 2,804
- Sq. Ft. Source: Public Records
- Finished Total: 2,804 Sq. Ft.
- Finished Above Grnd: 2,272 Sq. Ft.
- Finished Below Grnd: 532 Sq. Ft.
- Year Built: 1989
Lot Features
- Lot Size (Acres): 0.57
- Lot Size (Sq. Ft.): 24,829.2
- Zoning: RF
- Lot Description: Near Public Beach, Neighborhood, Cul-de-Sac, Level, Landscaped
Financial Considerations
- Association Fee: $425
- Assoc Fee Freq.: Annually
- Tax Amount: $8,386
- Tax Year: 25
Disclosures and Reports
- Lot Number: 59
Listed by Keller Williams Realty (207) 879-9800
Sold by Portside Real Estate Group (207) 747-4236
Get Pre-Approved Today
Schools
Schools serving 5 Winding Way
School District:Scarborough
| Name | Grades | Distance |
|---|---|---|
Pleasant Hill School 143 Highland Avenue, Scarborough, ME 04074 | K-2 | 0.7 mi |
Wentworth School 20 Quentin Drive, Scarborough, ME 04074 | 3-5 | 2.5 mi |
Scarborough Middle School 21 Quentin Drive, Scarborough, ME 04074 | 6-8 | 2.7 mi |
Scarborough High School 11 Municipal Drive, Scarborough, ME 04074 | 9-12 | 2.3 mi |
Disclaimer:
School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.
Price & Sales History for 5 Winding Way
Date
Details
Price
Change
Source
7/29/2026
Sold
$765,000
2.14%
MLS
6/17/2026
Listed
$749,000
—
MLS
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.
5 Winding Way, Scarborough, ME 04074 (MLS# 1667679) is a Single Family property that was sold at $765,000 on July 29, 2026. Want to learn more about 5 Winding Way? Do you have questions about finding other Single Family real estate for sale in Scarborough? You can browse all Scarborough real estate or contact a Coldwell Banker agent to request more information.

