Real Estate Investment Properties for Sale in Winter Harbor, ME

Looking for investment property in Winter Harbor, ME with high ROI ?

Explore a variety of short-term homes & houses in Winter Harbor, ME. Invest wisely with VRBO & Winter Harbor, 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 Winter Harbor, ME

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1 Mark Island Winter Harbor, ME Rare opportunity to own a 4+/- acre private Maine Island in the heart of Acadia, complete ...	3 beds \| N/A baths \| 2,004 sq.ft.	$2,300,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 0.01% Airbnb Rental Income: $1967 Traditional Rental Income: $2901 Airbnb ROI: -0.67% Traditional ROI: 0.01%
61 Misty Harbor Drive Winter Harbor, ME 2 Bedroom End Unit Condo right in town. New bathroom, interior is newly painted along with...	2 beds \| N/A baths \| 1,108 sq.ft.	$249,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 5.73% Airbnb Rental Income: $1960 Traditional Rental Income: $2281 Airbnb ROI: 2.18% Traditional ROI: 5.73%
Investment Properties for Sale in Other Cities of Maine
6 Proctor Road Biddeford , ME Call Bob Letellier (207) 590-5178. Attention Investors and Business owners! Here we are of...	N/A beds \| N/A baths \| 3,440 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $5745 Airbnb ROI: N/A Traditional ROI: 3.39%
28 Pleasant Hill Drive Waterville , ME Welcome to this beautifully maintained and thoughtfully updated single-level home, set on ...	3 beds \| N/A baths \| 1,344 sq.ft.	$304,900	Airbnb cash on cash: 1.68% Traditional cash on cash: 2.81% Airbnb Rental Income: $1665 Traditional Rental Income: $1523 Airbnb ROI: 1.68% Traditional ROI: 2.81%
265 Nubble Road York , ME Welcome to 265 Nubble Road! A rare offering on one of York's most iconic stretches. Surrou...	N/A beds \| N/A baths \| 2,631 sq.ft.	$1,275,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.24% Airbnb Rental Income: $null Traditional Rental Income: $2103 Airbnb ROI: N/A Traditional ROI: -0.24%
4 Ice House Point York , ME This property is a masterclass in harmonizing nature with refined modern design. It is a c...	4 beds \| N/A baths \| 3,976 sq.ft.	$9,889,000	Airbnb cash on cash: -0.93% Traditional cash on cash: -0.93% Airbnb Rental Income: $3760 Traditional Rental Income: $2963 Airbnb ROI: -0.93% Traditional ROI: -0.93%
85 Upper A Street Portland , ME Serenity Cottage will steal a little piece of your heart just like it has for the current ...	2 beds \| 1 baths \| 1,000 sq.ft.	$579,000	Airbnb cash on cash: 2.11% Traditional cash on cash: 2.03% Airbnb Rental Income: $2790 Traditional Rental Income: $2094 Airbnb ROI: 2.11% Traditional ROI: 2.03%
11 Ocean Spray Road Portland , ME Breath taking views at this one of a kind Peaks Island home! This newly renovated home sit...	2 beds \| N/A baths \| 2,345 sq.ft.	$1,999,900	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.11% Airbnb Rental Income: $2790 Traditional Rental Income: $3298 Airbnb ROI: -0.52% Traditional ROI: 0.11%
34 Harbor Road Friendship , ME Step into timeless elegance with this beautifully renovated Victorian located on a large l...	4 beds \| N/A baths \| 2,251 sq.ft.	$465,000	Airbnb cash on cash: 3.7% Traditional cash on cash: 4.55% Airbnb Rental Income: $3005 Traditional Rental Income: $2685 Airbnb ROI: 3.7% Traditional ROI: 4.55%
93 Cushnoc Road Vassalboro , ME Craving space, serenity, and a fresh startÃ¢â¬âwithout giving up convenience? Just a sh...	3 beds \| 2 baths \| 2,900 sq.ft.	$639,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 4.14% Airbnb Rental Income: $4141 Traditional Rental Income: $3398 Airbnb ROI: 3.91% Traditional ROI: 4.14%
17 Dyvonne Terrace Bridgton , ME BRIDGTON- Imagine waking up to +/-240' of serene Beaver Pond waterfront with breathtaking ...	3 beds \| N/A baths \| 2,090 sq.ft.	$785,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 3.63% Airbnb Rental Income: $1666 Traditional Rental Income: $3906 Airbnb ROI: -0.08% Traditional ROI: 3.63%
211 Augusta Road Topsham , ME Residential, Commercial & Investors please take notice. This unique property is located in...	4 beds \| N/A baths \| 4,214 sq.ft.	$1,495,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.31% Airbnb Rental Income: $null Traditional Rental Income: $6604 Airbnb ROI: N/A Traditional ROI: 3.31%
586 Webb Cove Drive Enfield , ME Gorgeous 2 bedroom, 2 bath waterfront home situated on +\- 3.9 acres. This home is nestled...	2 beds \| N/A baths \| 2,000 sq.ft.	$599,999	Airbnb cash on cash: -0.63% Traditional cash on cash: 4.21% Airbnb Rental Income: $1242 Traditional Rental Income: $3553 Airbnb ROI: -0.63% Traditional ROI: 4.21%
87 Farview Drive Sanford , ME Welcome to 87 Farview Drive in Sanford, a well-maintained 2013 Colonial set on just over h...	4 beds \| N/A baths \| 2,336 sq.ft.	$492,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.62% Airbnb Rental Income: $null Traditional Rental Income: $4107 Airbnb ROI: N/A Traditional ROI: 6.62%
11 Depot Road Eliot , ME Back on the Market at an Improved Price! This bright and spacious 3-bedroom home (plus ...	3 beds \| N/A baths \| 3,300 sq.ft.	$1,189,000	Airbnb cash on cash: 2.63% Traditional cash on cash: 2.26% Airbnb Rental Income: $5488 Traditional Rental Income: $3976 Airbnb ROI: 2.63% Traditional ROI: 2.26%
122 Onamor Drive Newfield , ME Welcome to Rock Haven Lake! Enjoy waterfront living in this year round home tucked along ...	2 beds \| N/A baths \| 1,902 sq.ft.	$599,900	Airbnb cash on cash: 0.3% Traditional cash on cash: 4.27% Airbnb Rental Income: $1602 Traditional Rental Income: $3368 Airbnb ROI: 0.3% Traditional ROI: 4.27%
1025 Douglas Drive Northport , ME Perched on the scenic side of Caswell Hill, this inviting home offers breathtaking, ever-c...	3 beds \| N/A baths \| 2,805 sq.ft.	$550,000	Airbnb cash on cash: 1.93% Traditional cash on cash: 5.1% Airbnb Rental Income: $2569 Traditional Rental Income: $3581 Airbnb ROI: 1.93% Traditional ROI: 5.1%

Real Estate investment in Winter-harbor, ME

There are 2 properties for sale in the city of Winter Harbor . The median list price in Winter Harbor is $1,274,500 and the average price per square foot is $819. In October 2025, the average monthly cash on cash return in Winter Harbor is 3.00%. The average monthly rental income in Winter Harbor is $2,591.

Winter-harbor, ME Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 2 investment properties available for sale in Winter-harbor.

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

The ROI for Long-Term is higher than the Short-Term in Winter-harbor with average rental income of $2,591.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Harbor, ME

1 Mark Island

Winter Harbor, ME

3 beds | N/A baths | 2,004 sq.ft.

$2,300,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 0.01%

Airbnb Rental Income: $1967

Traditional Rental Income: $2901

Airbnb ROI: -0.67%

Traditional ROI: 0.01%

61 Misty Harbor Drive

Winter Harbor, ME

2 beds | N/A baths | 1,108 sq.ft.

$249,000

Airbnb cash on cash: 2.18%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $1960

Traditional Rental Income: $2281

Airbnb ROI: 2.18%

Traditional ROI: 5.73%

Investment Properties for Sale in Other Cities of Maine

Biddeford , ME

N/A beds | N/A baths | 3,440 sq.ft.

$1,200,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.39%

Airbnb Rental Income: $null

Traditional Rental Income: $5745

Airbnb ROI: N/A

Traditional ROI: 3.39%

Waterville , ME

3 beds | N/A baths | 1,344 sq.ft.

$304,900

Airbnb cash on cash: 1.68%

Traditional cash on cash: 2.81%

Airbnb Rental Income: $1665

Traditional Rental Income: $1523

Airbnb ROI: 1.68%

Traditional ROI: 2.81%

York , ME

N/A beds | N/A baths | 2,631 sq.ft.

$1,275,000

Airbnb cash on cash: N/A

Traditional cash on cash: -0.24%

Airbnb Rental Income: $null

Traditional Rental Income: $2103

Airbnb ROI: N/A

Traditional ROI: -0.24%

York , ME

4 beds | N/A baths | 3,976 sq.ft.

$9,889,000

Airbnb cash on cash: -0.93%

Traditional cash on cash: -0.93%

Airbnb Rental Income: $3760

Traditional Rental Income: $2963

Airbnb ROI: -0.93%

Traditional ROI: -0.93%

Portland , ME

2 beds | 1 baths | 1,000 sq.ft.

$579,000

Airbnb cash on cash: 2.11%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $2790

Traditional Rental Income: $2094

Airbnb ROI: 2.11%

Traditional ROI: 2.03%

Portland , ME

2 beds | N/A baths | 2,345 sq.ft.

$1,999,900

Airbnb cash on cash: -0.52%

Traditional cash on cash: 0.11%

Airbnb Rental Income: $2790

Traditional Rental Income: $3298

Airbnb ROI: -0.52%

Traditional ROI: 0.11%

Friendship , ME

4 beds | N/A baths | 2,251 sq.ft.

$465,000

Airbnb cash on cash: 3.7%