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 \| 3 baths \| 2,004 sq.ft.	$2,300,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 0.01% Airbnb Rental Income: $3643 Traditional Rental Income: $2901 Airbnb ROI: -0.01% 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 \| 1 baths \| 1,108 sq.ft.	$249,000	Airbnb cash on cash: 6.25% Traditional cash on cash: 5.73% Airbnb Rental Income: $3110 Traditional Rental Income: $2281 Airbnb ROI: 6.25% Traditional ROI: 5.73%
682 Newman Street Winter Harbor, ME .	2 beds \| 2 baths \| N/A	$250,000	Airbnb cash on cash: 8.76% Traditional cash on cash: 11.35% Airbnb Rental Income: $3110 Traditional Rental Income: $3014 Airbnb ROI: 8.76% Traditional ROI: 11.35%
Investment Properties for Sale in Other Cities of Maine
6 Proctor Road Biddeford , ME Live in comfort and style while your property helps pay the bills! This one-of-a-kind oppo...	4 beds \| 4 baths \| 3,440 sq.ft.	$1,200,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 3.55% Airbnb Rental Income: $4792 Traditional Rental Income: $5745 Airbnb ROI: 1.81% Traditional ROI: 3.55%
28 Pleasant Hill Drive Waterville , ME Welcome to this beautifully maintained and thoughtfully updated single-level home, set on ...	3 beds \| 2 baths \| 1,344 sq.ft.	$314,900	Airbnb cash on cash: 8.87% Traditional cash on cash: 2.7% Airbnb Rental Income: $4249 Traditional Rental Income: $1523 Airbnb ROI: 8.87% Traditional ROI: 2.7%
81 Smithtown Road Pittston , ME Federal style 4 bedroom 1.5 bath home situated on .70 acres. Full of character, this home ...	4 beds \| 2 baths \| 1,200 sq.ft.	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.45% Airbnb Rental Income: $null Traditional Rental Income: $3205 Airbnb ROI: N/A Traditional ROI: 9.45%
116 School Street Kennebunkport , ME Experience tranquility and elegance in this beautifully renovated home, perfectly blending...	3 beds \| 3 baths \| 1,913 sq.ft.	$925,000	Airbnb cash on cash: 2.5% Traditional cash on cash: 2.88% Airbnb Rental Income: $4214 Traditional Rental Income: $3649 Airbnb ROI: 2.5% Traditional ROI: 2.88%
298 York Street York , ME Experience modern coastal living in this airy, loft-style condo, built in 2022 and nestled...	1 beds \| 1 baths \| 798 sq.ft.	$525,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 2.06% Airbnb Rental Income: $2030 Traditional Rental Income: $2338 Airbnb ROI: 0.36% Traditional ROI: 2.06%
4 Ice House Point York , ME This property is a masterclass in harmonizing nature with refined modern design. It is a c...	4 beds \| 3 baths \| 3,976 sq.ft.	$9,889,000	Airbnb cash on cash: -0.95% Traditional cash on cash: -0.93% Airbnb Rental Income: $3533 Traditional Rental Income: $2963 Airbnb ROI: -0.95% Traditional ROI: -0.93%
33 Highland Avenue York , ME With the iconic Nubble Lighthouse straight ahead, Long Sands Beach to the south, and Short...	2 beds \| 2 baths \| 1,126 sq.ft.	$685,000	Airbnb cash on cash: -0.01% Traditional cash on cash: 1.58% Airbnb Rental Income: $2132 Traditional Rental Income: $2601 Airbnb ROI: -0.01% Traditional ROI: 1.58%
8 Cotton Drive Gorham , ME Feel instantly at home in this beautiful open-concept Colonial, built in 2016. Offering 4 ...	4 beds \| 4 baths \| 3,038 sq.ft.	$799,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.41% Airbnb Rental Income: $null Traditional Rental Income: $5576 Airbnb ROI: N/A Traditional ROI: 5.41%
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.	$599,900	Airbnb cash on cash: 1.71% Traditional cash on cash: 1.93% Airbnb Rental Income: $2597 Traditional Rental Income: $2094 Airbnb ROI: 1.71% Traditional ROI: 1.93%
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 \| 2 baths \| 2,345 sq.ft.	$1,999,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.11% Airbnb Rental Income: $2597 Traditional Rental Income: $3298 Airbnb ROI: -0.6% Traditional ROI: 0.11%
40 Claman Drive Windham , ME Welcome to 40 Claman Drive, a charming and well-maintained 2-bedroom, 2-bathroom home nest...	2 beds \| 2 baths \| 1,528 sq.ft.	$614,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.46% Airbnb Rental Income: $null Traditional Rental Income: $2938 Airbnb ROI: N/A Traditional ROI: 3.46%
34 Harbor Road Friendship , ME Step into timeless elegance with this beautifully renovated Victorian located on a large l...	4 beds \| 2 baths \| 2,251 sq.ft.	$465,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 4.55% Airbnb Rental Income: $3430 Traditional Rental Income: $2685 Airbnb ROI: 4.51% Traditional ROI: 4.55%
93 Cushnoc Road Vassalboro , ME Craving space, serenity, and a fresh startâwithout giving up convenience? Just a short d...	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 \| 3 baths \| 2,090 sq.ft.	$879,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.13% Airbnb Rental Income: $null Traditional Rental Income: $3906 Airbnb ROI: N/A Traditional ROI: 3.13%
211 Augusta Road Topsham , ME Residential, Commercial & Investors please take notice. This unique property is located in...	4 beds \| 5 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%

Real Estate investment in Winter-harbor, ME

There are 3 properties for sale in the city of Winter Harbor . The median list price in Winter Harbor is $250,000 and the average price per square foot is $161. In September 2025, the average monthly cash on cash return in Winter Harbor is 6.00%. The average monthly rental income in Winter Harbor is $2,901.

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

There are 3 investment properties available for sale in Winter-harbor.

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

The ROI for Short-Term is higher than the Long-Term in Winter-harbor with average rental income of $3,110.

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 | 3 baths | 2,004 sq.ft.

$2,300,000

Airbnb cash on cash: -0.01%

Traditional cash on cash: 0.01%

Airbnb Rental Income: $3643

Traditional Rental Income: $2901

Airbnb ROI: -0.01%

Traditional ROI: 0.01%

61 Misty Harbor Drive

Winter Harbor, ME

2 beds | 1 baths | 1,108 sq.ft.

$249,000

Airbnb cash on cash: 6.25%

Traditional cash on cash: 5.73%

Airbnb Rental Income: $3110

Traditional Rental Income: $2281

Airbnb ROI: 6.25%

Traditional ROI: 5.73%

682 Newman Street

Winter Harbor, ME

2 beds | 2 baths | N/A

$250,000

Airbnb cash on cash: 8.76%

Traditional cash on cash: 11.35%

Airbnb Rental Income: $3110

Traditional Rental Income: $3014

Airbnb ROI: 8.76%

Traditional ROI: 11.35%

Investment Properties for Sale in Other Cities of Maine

Biddeford , ME

4 beds | 4 baths | 3,440 sq.ft.

$1,200,000

Airbnb cash on cash: 1.81%

Traditional cash on cash: 3.55%

Airbnb Rental Income: $4792

Traditional Rental Income: $5745

Airbnb ROI: 1.81%

Traditional ROI: 3.55%

Waterville , ME

3 beds | 2 baths | 1,344 sq.ft.

$314,900

Airbnb cash on cash: 8.87%

Traditional cash on cash: 2.7%

Airbnb Rental Income: $4249

Traditional Rental Income: $1523

Airbnb ROI: 8.87%

Traditional ROI: 2.7%

Pittston , ME

4 beds | 2 baths | 1,200 sq.ft.

$299,000

Airbnb cash on cash: N/A

Traditional cash on cash: 9.45%

Airbnb Rental Income: $null

Traditional Rental Income: $3205

Airbnb ROI: N/A

Traditional ROI: 9.45%

Kennebunkport , ME

3 beds | 3 baths | 1,913 sq.ft.

$925,000

Airbnb cash on cash: 2.5%

Traditional cash on cash: 2.88%

Airbnb Rental Income: $4214

Traditional Rental Income: $3649

Airbnb ROI: 2.5%

Traditional ROI: 2.88%

York , ME

1 beds | 1 baths | 798 sq.ft.

$525,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 2.06%

Airbnb Rental Income: $2030

Traditional Rental Income: $2338

Airbnb ROI: 0.36%

Traditional ROI: 2.06%

York , ME

4 beds | 3 baths | 3,976 sq.ft.

$9,889,000