Real Estate Investment Properties for Sale in Winslow, ME

Looking for investment property in Winslow, ME with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
100 N Pond Road Winslow, ME Modern cape offering 4 bedrooms, 3 baths, and 3,100 sq ft of thoughtfully designed living ...	4 beds \| 3 baths \| 3,100 sq.ft.	$549,000	Airbnb cash on cash: N/A Traditional cash on cash: 7.1% Airbnb Rental Income: $null Traditional Rental Income: $4470 Airbnb ROI: N/A Traditional ROI: 7.1%
941 Augusta Road Winslow, ME Well-maintained 3 bedroom, 1.5 bath home located just outside of in-town Winslow, offering...	3 beds \| 2 baths \| 1,441 sq.ft.	$334,900	Airbnb cash on cash: -0.56% Traditional cash on cash: 7.64% Airbnb Rental Income: $996 Traditional Rental Income: $3222 Airbnb ROI: -0.56% Traditional ROI: 7.64%
15 Marcoux Street Winslow, ME Turn-key, updated, and ready for summer--this one check's all the boxes. This fully renova...	4 beds \| 2 baths \| 1,428 sq.ft.	$389,900	Airbnb cash on cash: N/A Traditional cash on cash: 7.62% Airbnb Rental Income: $null Traditional Rental Income: $3249 Airbnb ROI: N/A Traditional ROI: 7.62%
54 Bay Street Winslow, ME Step back in time with this charming 1860 property that blends historic character with mod...	N/A beds \| 3 baths \| 2,066 sq.ft.	$250,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 10.15% Airbnb Rental Income: $818 Traditional Rental Income: $3048 Airbnb ROI: -0.67% Traditional ROI: 10.15%
8 St John Winslow, ME Well-maintained 4 bedroom, 1 bath ranch located in Winslow. Conveniently situated close to...	4 beds \| 1 baths \| 1,775 sq.ft.	$324,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.14% Airbnb Rental Income: $null Traditional Rental Income: $2686 Airbnb ROI: N/A Traditional ROI: 6.14%
335 Benton Avenue Winslow, ME Spacious raised ranch with 3 bedrooms, 1 bath, bonus room and utility room. Huge deck over...	3 beds \| 2 baths \| 1,176 sq.ft.	$240,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 9.82% Airbnb Rental Income: $996 Traditional Rental Income: $2853 Airbnb ROI: 0.07% Traditional ROI: 9.82%
3 Marcoux Street Winslow, ME Well-maintained 4-unit property with a new roof (11/2024). Three units have been extensive...	N/A beds \| 4 baths \| 3,328 sq.ft.	$499,500	Airbnb cash on cash: -0.77% Traditional cash on cash: 7.02% Airbnb Rental Income: $818 Traditional Rental Income: $4131 Airbnb ROI: -0.77% Traditional ROI: 7.02%

Real Estate investment in Winslow, ME

There are 7 properties for sale in the city of Winslow . The median list price in Winslow is $199,000 and the average price per square foot is $148. In May 2026, the average monthly cash on cash return in Winslow is 8.00%. The average monthly rental income in Winslow is $3,222.

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

There are 7 investment properties available for sale in Winslow.

In 2026, the best neighborhood to buy investment property is Winslow.

The ROI for Long-Term is higher than the Short-Term in Winslow with average rental income of $3,222.

Your search for investment property begins and ends here

Investment Property for Sale in Winslow, ME

100 N Pond Road

Winslow, ME

4 beds | 3 baths | 3,100 sq.ft.

$549,000

Airbnb cash on cash: N/A

Traditional cash on cash: 7.1%

Airbnb Rental Income: $null

Traditional Rental Income: $4470

Airbnb ROI: N/A

Traditional ROI: 7.1%

941 Augusta Road

Winslow, ME

3 beds | 2 baths | 1,441 sq.ft.

$334,900

Airbnb cash on cash: -0.56%

Traditional cash on cash: 7.64%

Airbnb Rental Income: $996

Traditional Rental Income: $3222

Airbnb ROI: -0.56%

Traditional ROI: 7.64%

15 Marcoux Street

Winslow, ME

4 beds | 2 baths | 1,428 sq.ft.

$389,900

Airbnb cash on cash: N/A

Traditional cash on cash: 7.62%

Airbnb Rental Income: $null

Traditional Rental Income: $3249

Airbnb ROI: N/A

Traditional ROI: 7.62%

54 Bay Street

Winslow, ME

N/A beds | 3 baths | 2,066 sq.ft.

$250,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 10.15%

Airbnb Rental Income: $818

Traditional Rental Income: $3048

Airbnb ROI: -0.67%

Traditional ROI: 10.15%

8 St John

Winslow, ME

4 beds | 1 baths | 1,775 sq.ft.

$324,900

Airbnb cash on cash: N/A

Traditional cash on cash: 6.14%

Airbnb Rental Income: $null

Traditional Rental Income: $2686

Airbnb ROI: N/A

Traditional ROI: 6.14%

335 Benton Avenue

Winslow, ME

3 beds | 2 baths | 1,176 sq.ft.

$240,000

Airbnb cash on cash: 0.07%

Traditional cash on cash: 9.82%

Airbnb Rental Income: $996

Traditional Rental Income: $2853

Airbnb ROI: 0.07%

Traditional ROI: 9.82%

3 Marcoux Street

Winslow, ME

N/A beds | 4 baths | 3,328 sq.ft.

$499,500

Airbnb cash on cash: -0.77%

Traditional cash on cash: 7.02%

Airbnb Rental Income: $818

Traditional Rental Income: $4131

Airbnb ROI: -0.77%

Traditional ROI: 7.02%

Real Estate investment in Winslow, ME

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

How many investment properties are available for sale in Winslow?

Which neighborhoods in Winslow to invest in 2026?

Long-Term vs. Short-Term Rentals in Winslow, Maine: Which will earn the best returns?

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