Real Estate Investment Properties for Sale in Islesboro, ME
Looking for investment property in Islesboro, ME with high ROI ?
Explore a variety of short-term homes & houses in Islesboro, ME. Invest wisely with VRBO & Islesboro, 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 Islesboro, ME
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
391 Main RoadIslesboro, MEPlum Point Cottage: Contemporary Island Home set on a hill with Breathtaking Ocean Views. ... |
2 beds | 2 baths | 2,154 sq.ft. |
$849,000 |
Airbnb cash on cash: 2.08%
|
135 Rebel Hill RoadIslesboro, MESlip away to Seabox Cottage, your ideal summer retreat or year-round haven. Reminiscent of... |
3 beds | 3 baths | 3,801 sq.ft. |
$899,000 |
Airbnb cash on cash: 2.18%
|
459 Main RoadIslesboro, MEWelcome to Maine summer living. This quintessential Maine summer cottage overlooks an expa... |
2 beds | 2 baths | 502 sq.ft. |
$395,000 |
Airbnb cash on cash: 7.36%
|
1317 Trim LaneIslesboro, MEOn an island in Maine sits this sweet cottage perched up from the water's edge with stunni... |
1 beds | 1 baths | 936 sq.ft. |
$2,000,000 |
Airbnb cash on cash: -1.58%
|
1159 Main RoadIslesboro, MEOceanfront retreat includes 17 acres with incredible views and 700 feet of sandy beach! O... |
4 beds | 1 baths | 2,680 sq.ft. |
$834,000 |
Airbnb cash on cash: 0.54%
|
292 Main RoadIslesboro, MEWelcome to 292 Main Road, Islesboro, MEâa large five-bedroom summer retreat perfect for ... |
5 beds | 2 baths | 2,409 sq.ft. |
$499,000 |
Airbnb cash on cash: 4.14%
|
300 Main RoadIslesboro, ME300 Main Rd is the former Island schoolhouse that is currently used as an art gallery. It ... |
1 beds | 2 baths | 2,553 sq.ft. |
$425,000 |
Airbnb cash on cash: 1.24%
|
101 Derby RoadIslesboro, MEIconic and Historic Dark Harbor Village Prime Real Estate in the heart of summer community... |
4 beds | 3 baths | 4,500 sq.ft. |
$495,000 |
Airbnb cash on cash: 1.46%
|
118 E East Shore DriveIslesboro, MEEast Shore Drive, Islesboro. Dark Harbor Village north along the shore dotted with grand ... |
5 beds | 4 baths | 2,400 sq.ft. |
$3,950,000 |
Airbnb cash on cash: -1.53%
|
364 & 367 Main RoadIslesboro, MELittle Broad Cove, Guinea, Islesboro. Easterly water views like you read about. Three be... |
4 beds | 2 baths | 4,470 sq.ft. |
$675,000 |
Airbnb cash on cash: 0.45%
|
351 Mill Creek RoadIslesboro, METhe Farrow-Farnsworth Home is an historic gem on about 40 acres overlooking Broad Cove and... |
4 beds | 4 baths | 4,064 sq.ft. |
$1,388,000 |
Airbnb cash on cash: 0.37%
|
108 Colony RoadIslesboro, METhis delightful cottage is set on a sunlit lot within walking distance of Dark Harbor Vill... |
1 beds | 1 baths | 804 sq.ft. |
$295,000 |
Airbnb cash on cash: 4.12%
|
115 Babbidge RoadIslesboro, METhis property offering includes an historic Arts and Craftsman-style Foursquare house - th... |
4 beds | 2 baths | 1,764 sq.ft. |
$625,000 |
Airbnb cash on cash: 2.02%
|
232 Mill Creek RoadIslesboro, MEDiscover Mill Creek Cottage: watch the Mill Creek rise and fall from this private 1.92± ... |
3 beds | 2 baths | 1,280 sq.ft. |
$925,000 |
Airbnb cash on cash: 2.6%
|
1317 Lot 1 Trim LaneIslesboro, MEOn an island in Maine sits this sweet cottage with room to expand or build on the elevated... |
1 beds | 1 baths | 936 sq.ft. |
$975,000 |
Airbnb cash on cash: 0.57%
|
1027 Meadow Pond RoadIslesboro, MENearly 3 acres on the tranquil island of Islesboro are now available. Property conveys pa... |
1 beds | N/A baths | 96 sq.ft. |
$185,000 |
Airbnb cash on cash: 7.09%
|
766 Billy Shore DriveIslesboro, MERarely does a property like this become available in Islesboro's storied and much-loved s... |
3 beds | 1 baths | 864 sq.ft. |
$685,000 |
Airbnb cash on cash: 3.85%
|
1235 Meadow Pond RoadIslesboro, METhis traditional extended Maine Cape is beautifully located on the north end of idyllic Is... |
4 beds | 1 baths | 1,656 sq.ft. |
$330,000 |
Airbnb cash on cash: 4.68%
|
1446 Meadow Pond RoadIslesboro, MEExperience the magic of coastal living at this seasonal camp, set on 7 acres of level land... |
2 beds | 1 baths | 500 sq.ft. |
$700,000 |
Airbnb cash on cash: 2.56%
|
Real Estate investment in Islesboro, ME
There are 19 properties for sale in the city of Islesboro . The median list price in Islesboro is $685,000 and the average price per square foot is $339. In September 2025, the average monthly cash on cash return in Islesboro is 3.00%. The average monthly rental income in Islesboro is $3,008.