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 |
|---|---|---|---|
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. |
$234,900 |
Airbnb cash on cash: 2.9%
|
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%
|
15 Bolduc AvenueWinslow, MEClassic simplicity best describes this updated 3-bedroom ranch located in a great neighbor... |
3 beds | N/A baths | 1,080 sq.ft. |
$299,900 |
Airbnb cash on cash: 1.2%
|
5 Mar Val TerraceWinslow, MEWelcome to 5 Mar Val Terrace, Unit B1 an inviting 2-bedroom, 1-bath ground-level condo off... |
2 beds | N/A baths | 1,122 sq.ft. |
$199,900 |
Airbnb cash on cash: 2.12%
|
701 Augusta RoadWinslow, MESet back from the road, this Winslow country Cape offers a peaceful place to slow down and... |
4 beds | N/A baths | 1,845 sq.ft. |
$324,000 |
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: -0.61%
|
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: 0.47%
|
242 China RoadWinslow, MEWelcome to this charming 3-bedroom, 2-bathroom single-level ranch offering comfort, space,... |
3 beds | N/A baths | 1,456 sq.ft. |
$359,000 |
Airbnb cash on cash: 1.43%
|
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: 3.68%
|
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: 1.3%
|
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: 3.7%
|
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: -0.79%
|
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. |
$498,000 |
Airbnb cash on cash: N/A
|
5 Chickadee TrailWinslow, MEBeautiful, cozy, and peaceful doesn't begin to describe this well cared for condo. Locate... |
2 beds | N/A baths | 1,483 sq.ft. |
$365,000 |
Airbnb cash on cash: 0.64%
|
5 Second StreetWinslow, MEBeautiful 3-Bedroom Colonial in Winslow! Nestled on a quiet dead-end street, this stunn... |
3 beds | N/A baths | 2,354 sq.ft. |
$359,000 |
Airbnb cash on cash: 0.1%
|
2 Whippoorwill DriveWinslow, ME13029 - Why 2 Whippoorwill Drive? Experience easy living in this charming ranch-style con... |
2 beds | N/A baths | 1,508 sq.ft. |
$369,500 |
Airbnb cash on cash: 1.94%
|
13 Poulin StreetWinslow, MEQuaint and easy to maintain, this Winslow ranch features warm wood floors, vinyl windows, ... |
2 beds | N/A baths | 1,040 sq.ft. |
$219,500 |
Airbnb cash on cash: 3.9%
|
Real Estate investment in Winslow, ME
There are 17 properties for sale in the city of Winslow . The median list price in Winslow is $299,900 and the average price per square foot is $173. In December 2025, the average monthly cash on cash return in Winslow is 7.00%. The average monthly rental income in Winslow is $2,806.