Real Estate Investment Properties for Sale in Winslow, ME
Looking for investment property in Winslow, ME with high ROI ?
Explore a variety of short-term homes & houses in Winslow, ME. Invest wisely with VRBO & Winslow, ME Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Winslow, ME
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
65 Wood StreetWinslow, MEHere's your chance to own a beautifully maintained 3-unit property that blends classic cha... |
N/A beds | N/A baths | 3,172 sq.ft. |
$485,000 |
Airbnb cash on cash: -0.85%
|
85 Halifax StreetWinslow, MECustom-Built 2-Bedroom Home with Character: This 2-bedroom, 1.5-bath custom-built home fea... |
2 beds | N/A baths | 1,730 sq.ft. |
$254,900 |
Airbnb cash on cash: 3.7%
|
29 Halifax StreetWinslow, MEDuplex located in-town Winslow featuring two spacious units ââ¬â one with 4 bedrooms a... |
N/A beds | N/A baths | 2,000 sq.ft. |
$200,000 |
Airbnb cash on cash: -0.1%
|
701 Augusta RoadWinslow, MECharming Winslow Country Cape in excellent condition. The large, private backyard features... |
5 beds | N/A baths | 1,845 sq.ft. |
$339,000 |
Airbnb cash on cash: N/A
|
2 and 3 Blue Heron LaneWinslow, MEAmazing 2 for 1 special! The waterside cabin is seasonal with a main living area and bedro... |
3 beds | N/A baths | 1,982 sq.ft. |
$499,900 |
Airbnb cash on cash: -0.05%
|
1 S Ridge DriveWinslow, MELet's talk....This is a spacious and beautifully crafted, 3-bedroom, 2.5-bathroom contempo... |
3 beds | N/A baths | 2,913 sq.ft. |
$595,000 |
Airbnb cash on cash: 0.94%
|
441 S Reynolds RdWinslow, MEInvestor & Handyman Special - Prime Opportunity in Winslow! Attention savvy buyers! Thi... |
2 beds | N/A baths | 720 sq.ft. |
$179,000 |
Airbnb cash on cash: 5.24%
|
21 Cardinal WayWinslow, MEOne level living at its finest! This first floor, 2 bedroom, 2 full bath condo is located... |
2 beds | N/A baths | 1,508 sq.ft. |
$369,500 |
Airbnb cash on cash: 2.07%
|
436 N Pond RoadWinslow, MEDiscover the perfect blend of country living and convenience with this charming mobile hom... |
2 beds | N/A baths | 854 sq.ft. |
$229,000 |
Airbnb cash on cash: 4.93%
|
54 Bay StreetWinslow, MEStep back in time with this charming 1860 property that blends historic character with mod... |
N/A beds | N/A baths | 2,066 sq.ft. |
$299,000 |
Airbnb cash on cash: -0.85%
|
105 S Pond RoadWinslow, MEDiscover the charm and character of this beautifully unique home set on more than 10 peace... |
4 beds | N/A baths | 3,210 sq.ft. |
$595,000 |
Airbnb cash on cash: N/A
|
23 Monument StreetWinslow, ME3-unit building in convenient Winslow location. This building is a "fixer upper" but has ... |
N/A beds | N/A baths | 2,239 sq.ft. |
$169,000 |
Airbnb cash on cash: -0.2%
|
364 Cushman RoadWinslow, MESet on 5.58 peaceful acres with frontage along a scenic stream, this Winslow property comb... |
2 beds | N/A baths | 881 sq.ft. |
$224,900 |
Airbnb cash on cash: 5.04%
|
Real Estate investment in Winslow, ME
There are 13 properties for sale in the city of Winslow . The median list price in Winslow is $276,950 and the average price per square foot is $144. In October 2025, the average monthly cash on cash return in Winslow is 8.00%. The average monthly rental income in Winslow is $2,841.