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
161 Birch Harbor Rd Winter Harbor, ME Move in ready to this New England log home situated on almost 8 country acres. Land abuts ...	3 beds \| 1 baths \| 1,680 sq.ft.	$445,000	Airbnb cash on cash: 2.66% Traditional cash on cash: 3.6% Airbnb Rental Income: $2376 Traditional Rental Income: $2181 Airbnb ROI: 2.66% Traditional ROI: 3.6%
25 Belleview Ave Winter Harbor, ME Charming home in down-town Winter Harbor on a quiet street with a spacious & private yard....	4 beds \| 2 baths \| 2,248 sq.ft.	$389,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 6.79% Airbnb Rental Income: $2564 Traditional Rental Income: $2940 Airbnb ROI: 4.07% Traditional ROI: 6.79%
112 Hillcrest Dr Winter Harbor, ME Inviting 3 bedroom home with a thoughtful floorplan, plus an addition offering a sizeable ...	3 beds \| 1 baths \| 2,451 sq.ft.	$375,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 7.24% Airbnb Rental Income: $2376 Traditional Rental Income: $2997 Airbnb ROI: 3.81% Traditional ROI: 7.24%
29 Loons Call Winter Harbor, ME A lavish home with an exceptional shoreline. MDI is nice, but looking across Frenchman Bay...	4 beds \| 4 baths \| 3,250 sq.ft.	$1,350,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 3.89% Airbnb Rental Income: $2564 Traditional Rental Income: $6229 Airbnb ROI: 0.48% Traditional ROI: 3.89%
2 Crane Rd Winter Harbor, ME 2 Crane Rd, Winter Harbor, ME 04693 \| Single Family Residential	3 beds \| 1 baths \| 1,120 sq.ft.	$239,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 7.56% Airbnb Rental Income: $2376 Traditional Rental Income: $2330 Airbnb ROI: 5.17% Traditional ROI: 7.56%
61 Hillcrest Dr Winter Harbor, ME 61 Hillcrest Dr, Winter Harbor, ME 04693 \| Manufactured Home	2 beds \| 2 baths \| 1,320 sq.ft.	$265,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 3.67% Airbnb Rental Income: $1743 Traditional Rental Income: $1596 Airbnb ROI: 2.34% Traditional ROI: 3.67%
800 Summer Harbor Rd Winter Harbor, ME 800 Summer Harbor Rd, Winter Harbor, ME 04693 \| Single Family Residential	3 beds \| 4 baths \| 3,676 sq.ft.	$2,200,000	Airbnb cash on cash: -1.52% Traditional cash on cash: -1.33% Airbnb Rental Income: $2376 Traditional Rental Income: $2181 Airbnb ROI: -1.52% Traditional ROI: -1.33%
20 Rand Ln Winter Harbor, ME 20 Rand Ln, Winter Harbor, ME 04693 \| Single Family Residential	5 beds \| 4 baths \| 2,634 sq.ft.	$595,000	Airbnb cash on cash: -0.45% Traditional cash on cash: 5.95% Airbnb Rental Income: $1605 Traditional Rental Income: $4704 Airbnb ROI: -0.45% Traditional ROI: 5.95%
102 Sargent St Winter Harbor, ME 102 Sargent St, Winter Harbor, ME 04693 \| Single Family Residential	1 beds \| 1 baths \| 630 sq.ft.	$399,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 0.9% Airbnb Rental Income: $1626 Traditional Rental Income: $1309 Airbnb ROI: 0.52% Traditional ROI: 0.9%
430 Main St Winter Harbor, ME 430 Main St, Winter Harbor, ME 04693 \| Single Family Residential	6 beds \| 4 baths \| 4,074 sq.ft.	$1,595,000	Airbnb cash on cash: -1.64% Traditional cash on cash: 1.49% Airbnb Rental Income: $1605 Traditional Rental Income: $5794 Airbnb ROI: -1.64% Traditional ROI: 1.49%
MAP9LOT1B Newman St Winter Harbor, ME MAP9LOT1B Newman St, Winter Harbor, ME 04693 \| Other	N/A beds \| N/A baths \| N/A	$89,000	Airbnb cash on cash: 8.49% Traditional cash on cash: 11.65% Airbnb Rental Income: $1468 Traditional Rental Income: $1309 Airbnb ROI: 8.49% Traditional ROI: 11.65%

Real Estate investment in Winter-harbor, ME

There are 11 properties for sale in the city of Winter Harbor . The median list price in Winter Harbor is $322,307 and the average price per square foot is $140. In September 2026, the average monthly cash on cash return in Winter Harbor is 4.00%. The average monthly rental income in Winter Harbor is $2,330.

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

There are 11 investment properties available for sale in Winter-harbor.

In 2026, 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 $2,330.

Your search for investment property begins and ends here

Investment Property for Sale in Winter Harbor, ME

161 Birch Harbor Rd

Winter Harbor, ME

3 beds | 1 baths | 1,680 sq.ft.

$445,000

Airbnb cash on cash: 2.66%

Traditional cash on cash: 3.6%

Airbnb Rental Income: $2376

Traditional Rental Income: $2181

Airbnb ROI: 2.66%

Traditional ROI: 3.6%

25 Belleview Ave

Winter Harbor, ME

4 beds | 2 baths | 2,248 sq.ft.

$389,000

Airbnb cash on cash: 4.07%

Traditional cash on cash: 6.79%

Airbnb Rental Income: $2564

Traditional Rental Income: $2940

Airbnb ROI: 4.07%

Traditional ROI: 6.79%

112 Hillcrest Dr

Winter Harbor, ME

3 beds | 1 baths | 2,451 sq.ft.

$375,000

Airbnb cash on cash: 3.81%

Traditional cash on cash: 7.24%

Airbnb Rental Income: $2376

Traditional Rental Income: $2997

Airbnb ROI: 3.81%

Traditional ROI: 7.24%

29 Loons Call

Winter Harbor, ME

4 beds | 4 baths | 3,250 sq.ft.

$1,350,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 3.89%

Airbnb Rental Income: $2564

Traditional Rental Income: $6229

Airbnb ROI: 0.48%

Traditional ROI: 3.89%

2 Crane Rd

Winter Harbor, ME

3 beds | 1 baths | 1,120 sq.ft.

$239,000

Airbnb cash on cash: 5.17%

Traditional cash on cash: 7.56%

Airbnb Rental Income: $2376

Traditional Rental Income: $2330

Airbnb ROI: 5.17%

Traditional ROI: 7.56%

61 Hillcrest Dr

Winter Harbor, ME

2 beds | 2 baths | 1,320 sq.ft.

$265,000

Airbnb cash on cash: 2.34%

Traditional cash on cash: 3.67%

Airbnb Rental Income: $1743

Traditional Rental Income: $1596

Airbnb ROI: 2.34%

Traditional ROI: 3.67%

800 Summer Harbor Rd

Winter Harbor, ME

3 beds | 4 baths | 3,676 sq.ft.

$2,200,000

Airbnb cash on cash: -1.52%

Traditional cash on cash: -1.33%

Airbnb Rental Income: $2376

Traditional Rental Income: $2181

Airbnb ROI: -1.52%

Traditional ROI: -1.33%

20 Rand Ln

Winter Harbor, ME

5 beds | 4 baths | 2,634 sq.ft.

$595,000

Airbnb cash on cash: -0.45%

Traditional cash on cash: 5.95%

Airbnb Rental Income: $1605

Traditional Rental Income: $4704

Airbnb ROI: -0.45%