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

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
391 Main Road Islesboro, ME Plum Point Cottage: Contemporary Island Home set on a hill with Breathtaking Ocean Views. ...	2 beds \| N/A baths \| 2,154 sq.ft.	$795,000	Airbnb cash on cash: -1.88% Traditional cash on cash: 2.33% Airbnb Rental Income: $470 Traditional Rental Income: $3324 Airbnb ROI: -1.88% Traditional ROI: 2.33%
135 Rebel Hill Road Islesboro, ME Slip away to Seabox Cottage, your ideal summer retreat or year-round haven. Reminiscent of...	3 beds \| N/A baths \| 3,801 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.07% Airbnb Rental Income: $null Traditional Rental Income: $3937 Airbnb ROI: N/A Traditional ROI: 3.07%
1317 Trim Lane Islesboro, ME On an island in Maine sits this sweet cottage perched up from the water's edge with stunni...	1 beds \| N/A baths \| 936 sq.ft.	$2,000,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.52% Airbnb Rental Income: $null Traditional Rental Income: $1648 Airbnb ROI: N/A Traditional ROI: -1.52%
1578 Pripet Wood Lane Islesboro, ME Tucked away on two serene acres along Islesboro's northeast shore, this beautifully reimag...	4 beds \| N/A baths \| 1,654 sq.ft.	$999,900	Airbnb cash on cash: -0.46% Traditional cash on cash: 0.69% Airbnb Rental Income: $1824 Traditional Rental Income: $2398 Airbnb ROI: -0.46% Traditional ROI: 0.69%
1159 Main Road Islesboro, ME Oceanfront retreat includes 17 acres with incredible views and 700 feet of sandy beach! S...	4 beds \| N/A baths \| 2,680 sq.ft.	$798,000	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.16% Airbnb Rental Income: $1824 Traditional Rental Income: $3008 Airbnb ROI: -0.1% Traditional ROI: 2.16%
108 Derby Road Islesboro, ME Tucked away on a quiet side street, this charming property is just a short stroll from the...	4 beds \| N/A baths \| 2,200 sq.ft.	$385,000	Airbnb cash on cash: 1.08% Traditional cash on cash: 7.04% Airbnb Rental Income: $1824 Traditional Rental Income: $3482 Airbnb ROI: 1.08% Traditional ROI: 7.04%
292 & 300 Main Road Islesboro, ME Discover a unique opportunity in Mid-Island Islesboro, where history and potential converg...	5 beds \| N/A baths \| 4,962 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $4507 Airbnb ROI: N/A Traditional ROI: 3.22%
292 Main Road Islesboro, ME Winfield Scott Pendleton House: A Historic Islesboro Gem. Step back in time and discover t...	5 beds \| N/A baths \| 2,409 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.94% Airbnb Rental Income: $null Traditional Rental Income: $3495 Airbnb ROI: N/A Traditional ROI: 4.94%
300 Main Road Islesboro, ME Step into history with this remarkable property, originally the Pendleton School, Islesbor...	1 beds \| N/A baths \| 2,553 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $2515 Airbnb ROI: N/A Traditional ROI: 3.73%
101 Derby Road Islesboro, ME Iconic and Historic Dark Harbor Village Prime Real Estate in the heart of summer community...	4 beds \| N/A baths \| 4,500 sq.ft.	$495,000	Airbnb cash on cash: 0.33% Traditional cash on cash: 6.77% Airbnb Rental Income: $1824 Traditional Rental Income: $4316 Airbnb ROI: 0.33% Traditional ROI: 6.77%
118 East Shore Drive Islesboro, ME East Shore Drive, Islesboro. Dark Harbor Village north along the shore dotted with grand ...	5 beds \| N/A baths \| 2,400 sq.ft.	$3,950,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.91% Airbnb Rental Income: $null Traditional Rental Income: $5397 Airbnb ROI: N/A Traditional ROI: -0.91%
364 & 367 Main Road Islesboro, ME Little Broad Cove, Guinea, Islesboro. Easterly water views like you read about. Three be...	4 beds \| N/A baths \| 4,470 sq.ft.	$599,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 5.71% Airbnb Rental Income: $1824 Traditional Rental Income: $4602 Airbnb ROI: -0.14% Traditional ROI: 5.71%
108 Colony Road Islesboro, ME This delightful cottage is set on a sunlit lot within walking distance of Dark Harbor Vill...	1 beds \| N/A baths \| 804 sq.ft.	$295,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.95% Airbnb Rental Income: $null Traditional Rental Income: $2030 Airbnb ROI: N/A Traditional ROI: 5.95%
115 Babbidge Road Islesboro, ME This property offering includes an historic Arts and Craftsman-style Foursquare house - th...	5 beds \| N/A baths \| 1,764 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.83% Airbnb Rental Income: $null Traditional Rental Income: $3448 Airbnb ROI: N/A Traditional ROI: 5.83%
1317 Lot 1 Trim Lane Islesboro, ME On an island in Maine sits this sweet cottage with room to expand or build on the elevated...	1 beds \| N/A baths \| 936 sq.ft.	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.49% Airbnb Rental Income: $null Traditional Rental Income: $2353 Airbnb ROI: N/A Traditional ROI: 1.49%
1027 Meadow Pond Road Islesboro, ME Nearly 3 acres on the tranquil island of Islesboro are now available. Property conveys fu...	1 beds \| N/A baths \| 96 sq.ft.	$185,000	Airbnb cash on cash: N/A Traditional cash on cash: 11.35% Airbnb Rental Income: $null Traditional Rental Income: $2272 Airbnb ROI: N/A Traditional ROI: 11.35%
766 Billy Shore Drive Islesboro, ME Rarely does a property like this become available in Islesboro's storied and much-loved s...	3 beds \| N/A baths \| 864 sq.ft.	$685,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.56% Airbnb Rental Income: $null Traditional Rental Income: $2371 Airbnb ROI: N/A Traditional ROI: 2.56%
1446 Meadow Pond Road Islesboro, ME Experience the magic of coastal living at this seasonal camp, set on 7 acres of level land...	2 beds \| N/A baths \| 500 sq.ft.	$700,000	Airbnb cash on cash: -2.18% Traditional cash on cash: 0.5% Airbnb Rental Income: $470 Traditional Rental Income: $1951 Airbnb ROI: -2.18% Traditional ROI: 0.5%
376 West Bay Road Islesboro, ME Come explore this unique opportunity encompassing 11.5+/- acre and offering western views ...	2 beds \| N/A baths \| 1,234 sq.ft.	$385,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 5.71% Airbnb Rental Income: $470 Traditional Rental Income: $2520 Airbnb ROI: -0.71% Traditional ROI: 5.71%

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 $318. In December 2025, the average monthly cash on cash return in Islesboro is 3.00%. The average monthly rental income in Islesboro is $2,764.

Islesboro, ME Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 19 investment properties available for sale in Islesboro.

In 2025, the best neighborhood to buy investment property is Islesboro.

The ROI for Short-Term is higher than the Long-Term in Islesboro with average rental income of $1,824.

Your search for investment property begins and ends here

Investment Property for Sale in Islesboro, ME

391 Main Road

Islesboro, ME

2 beds | N/A baths | 2,154 sq.ft.

$795,000

Airbnb cash on cash: -1.88%

Traditional cash on cash: 2.33%

Airbnb Rental Income: $470

Traditional Rental Income: $3324

Airbnb ROI: -1.88%

Traditional ROI: 2.33%

135 Rebel Hill Road

Islesboro, ME

3 beds | N/A baths | 3,801 sq.ft.

$899,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.07%

Airbnb Rental Income: $null

Traditional Rental Income: $3937

Airbnb ROI: N/A

Traditional ROI: 3.07%

1317 Trim Lane

Islesboro, ME

1 beds | N/A baths | 936 sq.ft.

$2,000,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.52%

Airbnb Rental Income: $null

Traditional Rental Income: $1648

Airbnb ROI: N/A

Traditional ROI: -1.52%

1578 Pripet Wood Lane

Islesboro, ME

4 beds | N/A baths | 1,654 sq.ft.

$999,900

Airbnb cash on cash: -0.46%

Traditional cash on cash: 0.69%

Airbnb Rental Income: $1824

Traditional Rental Income: $2398

Airbnb ROI: -0.46%

Traditional ROI: 0.69%

1159 Main Road

Islesboro, ME

4 beds | N/A baths | 2,680 sq.ft.

$798,000

Airbnb cash on cash: -0.1%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $1824

Traditional Rental Income: $3008

Airbnb ROI: -0.1%

Traditional ROI: 2.16%

108 Derby Road

Islesboro, ME

4 beds | N/A baths | 2,200 sq.ft.

$385,000

Airbnb cash on cash: 1.08%

Traditional cash on cash: 7.04%

Airbnb Rental Income: $1824

Traditional Rental Income: $3482

Airbnb ROI: 1.08%

Traditional ROI: 7.04%

292 & 300 Main Road

Islesboro, ME

5 beds | N/A baths | 4,962 sq.ft.

$850,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.22%

Airbnb Rental Income: $null

Traditional Rental Income: $4507

Airbnb ROI: N/A

Traditional ROI: 3.22%

292 Main Road

Islesboro, ME

5 beds | N/A baths | 2,409 sq.ft.

$499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.94%

Airbnb Rental Income: $null

Traditional Rental Income: $3495

Airbnb ROI: N/A