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
5 Robert St Winslow, ME	3 beds \| 1 baths \| 1,512 sq.ft.	$349,900	Airbnb cash on cash: 0.78% Traditional cash on cash: 5.53% Airbnb Rental Income: $1326 Traditional Rental Income: $2478 Airbnb ROI: 0.78% Traditional ROI: 5.53%
17 Hapworth Ln Winslow, ME Great home to fix up, has a lot of potential. Open the windows in the summer and hear the ...	3 beds \| 1 baths \| 920 sq.ft.	$199,900	Airbnb cash on cash: 2.4% Traditional cash on cash: 6.98% Airbnb Rental Income: $1326 Traditional Rental Income: $1785 Airbnb ROI: 2.4% Traditional ROI: 6.98%
941 Augusta Rd Winslow, ME Remodeled home, New shingles, new siding, new windows, doors, and new slab in the garage!T...	3 beds \| 1 baths \| 1,441 sq.ft.	$349,900	Airbnb cash on cash: 0.26% Traditional cash on cash: 7.28% Airbnb Rental Income: $1326 Traditional Rental Income: $3222 Airbnb ROI: 0.26% Traditional ROI: 7.28%
15 Bolduc Ave Winslow, ME Classic simplicity best describes this updated 3-bedroom ranch located in a great neighbor...	3 beds \| 1 baths \| 1,080 sq.ft.	$275,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 4.91% Airbnb Rental Income: $1326 Traditional Rental Income: $1825 Airbnb ROI: 1.4% Traditional ROI: 4.91%
5 Mar Val Ter #B1 Winslow, ME Welcome to 5 Mar Val Terrace, Unit B1 an inviting 2-bedroom, 1-bath ground-level condo off...	2 beds \| 1 baths \| 1,122 sq.ft.	$193,000	Airbnb cash on cash: 2.25% Traditional cash on cash: 5.33% Airbnb Rental Income: $1568 Traditional Rental Income: $1683 Airbnb ROI: 2.25% Traditional ROI: 5.33%
701 Augusta Rd Winslow, ME Set back from the road, this Winslow country Cape offers a peaceful place to slow down and...	4 beds \| 2 baths \| 1,845 sq.ft.	$324,000	Airbnb cash on cash: N/A Traditional cash on cash: 6.25% Airbnb Rental Income: $null Traditional Rental Income: $2710 Airbnb ROI: N/A Traditional ROI: 6.25%
441 S Reynolds Rd Rd Winslow, ME Investor & Handyman Special - Prime Opportunity in Winslow! Attention savvy buyers! Thi...	2 beds \| 1 baths \| 720 sq.ft.	$179,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 9.37% Airbnb Rental Income: $1568 Traditional Rental Income: $2088 Airbnb ROI: 3.68% Traditional ROI: 9.37%
3 Blue Heron Ln Winslow, ME Have you been waiting for an affordable waterfront happy place to make family memories or ...	1 beds \| 1 baths \| 634 sq.ft.	$275,000	Airbnb cash on cash: -0.67% Traditional cash on cash: 4.34% Airbnb Rental Income: $916 Traditional Rental Income: $1985 Airbnb ROI: -0.67% Traditional ROI: 4.34%
1 #1 Industrial Rd Winslow, ME 1 #1 Industrial Rd, Winslow, ME 04901 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$175,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 5.97% Airbnb Rental Income: $796 Traditional Rental Income: $1477 Airbnb ROI: -0.05% Traditional ROI: 5.97%
5 Mar-Val Ter Winslow, ME Beautifully Remodeled 2-Bedroom Condo in Quiet Winslow Neighborhood Welcome home to thi...	2 beds \| N/A baths \| 1,000 sq.ft.	$179,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 9.09% Airbnb Rental Income: $1568 Traditional Rental Income: $2040 Airbnb ROI: 3.68% Traditional ROI: 9.09%
51 N Reynolds Rd Winslow, ME 51 N Reynolds Rd, Winslow, ME 04901 \| Single Family Residential	2 beds \| 1 baths \| 1,544 sq.ft.	$365,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 3.66% Airbnb Rental Income: $1568 Traditional Rental Income: $2153 Airbnb ROI: 0.64% Traditional ROI: 3.66%
95 N Reynolds Rd Winslow, ME Be the first to live in this brand new spacious 5 bedroom 2.5 bath ranch! If space is what...	5 beds \| 2 baths \| 3,058 sq.ft.	$464,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.59% Airbnb Rental Income: $null Traditional Rental Income: $3470 Airbnb ROI: N/A Traditional ROI: 6.59%
0 S Reynolds Road, Lot 2 Winslow, ME 0 S Reynolds Road, Lot 2, Winslow, ME 04901 \| Single Family Residential	3 beds \| 2 baths \| 1,280 sq.ft.	$320,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 3.74% Airbnb Rental Income: $1326 Traditional Rental Income: $1926 Airbnb ROI: 0.39% Traditional ROI: 3.74%
0 China Rd Winslow, ME 0 China Rd, Winslow, ME 04901 \| Other	N/A beds \| N/A baths \| 1,456 sq.ft.	$175,000	Airbnb cash on cash: -0.05% Traditional cash on cash: 7.07% Airbnb Rental Income: $796 Traditional Rental Income: $1661 Airbnb ROI: -0.05% Traditional ROI: 7.07%
0 S Reynolds Rd Lot 1 Winslow, ME 0 S Reynolds Rd Lot 1, Winslow, ME 04901 \| Single Family Residential	2 beds \| 2 baths \| 902 sq.ft.	$268,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 7.81% Airbnb Rental Income: $1568 Traditional Rental Income: $2660 Airbnb ROI: 1.71% Traditional ROI: 7.81%
423 Maple Ridge Rd Winslow, ME 423 Maple Ridge Rd, Winslow, ME 04901 \| Single Family Residential	3 beds \| 2 baths \| 1,080 sq.ft.	$270,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 7.65% Airbnb Rental Income: $1326 Traditional Rental Income: $2637 Airbnb ROI: 0.89% Traditional ROI: 7.65%
12 Harry St Winslow, ME Opportunity meets charm in this well-located Winslow ranch. Whether you're a first-time bu...	2 beds \| 1 baths \| 1,074 sq.ft.	$299,900	Airbnb cash on cash: 1.28% Traditional cash on cash: 5.64% Airbnb Rental Income: $1568 Traditional Rental Income: $2348 Airbnb ROI: 1.28% Traditional ROI: 5.64%
218 S Reynolds Rd Winslow, ME OPEN HOUSE Sunday 3/8/26 from 12:30-2:00Set privately along the South Reynolds Road, t...	4 beds \| 3 baths \| 3,000 sq.ft.	$719,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $3382 Airbnb ROI: N/A Traditional ROI: 2.48%
653 Abbott Rd Winslow, ME 653 Abbott Rd, Winslow, ME 04901 \| Single Family Residential	3 beds \| 2 baths \| 960 sq.ft.	$289,900	Airbnb cash on cash: 0.67% Traditional cash on cash: 6.5% Airbnb Rental Income: $1326 Traditional Rental Income: $2509 Airbnb ROI: 0.67% Traditional ROI: 6.5%
96 Clinton Ave Winslow, ME 96 Clinton Ave, Winslow, ME 04901 \| Single Family Residential	4 beds \| 2 baths \| 1,509 sq.ft.	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.8% Airbnb Rental Income: $null Traditional Rental Income: $3243 Airbnb ROI: N/A Traditional ROI: 9.8%
8 St John St Winslow, ME Well-maintained 4 bedroom, 1 bath ranch located in Winslow. Conveniently situated close to...	4 beds \| 1 baths \| 1,775 sq.ft.	$329,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.02% Airbnb Rental Income: $null Traditional Rental Income: $2686 Airbnb ROI: N/A Traditional ROI: 6.02%

Real Estate investment in Winslow, ME

There are 21 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 $157. In March 2026, the average monthly cash on cash return in Winslow is 6.00%. The average monthly rental income in Winslow is $1,956.

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

There are 21 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 $1,956.

Your search for investment property begins and ends here

Investment Property for Sale in Winslow, ME

5 Robert St

Winslow, ME

3 beds | 1 baths | 1,512 sq.ft.

$349,900

Airbnb cash on cash: 0.78%

Traditional cash on cash: 5.53%

Airbnb Rental Income: $1326

Traditional Rental Income: $2478

Airbnb ROI: 0.78%

Traditional ROI: 5.53%

17 Hapworth Ln

Winslow, ME

3 beds | 1 baths | 920 sq.ft.

$199,900

Airbnb cash on cash: 2.4%

Traditional cash on cash: 6.98%

Airbnb Rental Income: $1326

Traditional Rental Income: $1785

Airbnb ROI: 2.4%

Traditional ROI: 6.98%

941 Augusta Rd

Winslow, ME

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

$349,900

Airbnb cash on cash: 0.26%

Traditional cash on cash: 7.28%

Airbnb Rental Income: $1326

Traditional Rental Income: $3222

Airbnb ROI: 0.26%

Traditional ROI: 7.28%

15 Bolduc Ave

Winslow, ME

3 beds | 1 baths | 1,080 sq.ft.

$275,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 4.91%

Airbnb Rental Income: $1326

Traditional Rental Income: $1825

Airbnb ROI: 1.4%

Traditional ROI: 4.91%

5 Mar Val Ter #B1

Winslow, ME

2 beds | 1 baths | 1,122 sq.ft.

$193,000

Airbnb cash on cash: 2.25%

Traditional cash on cash: 5.33%

Airbnb Rental Income: $1568

Traditional Rental Income: $1683

Airbnb ROI: 2.25%

Traditional ROI: 5.33%

701 Augusta Rd

Winslow, ME

4 beds | 2 baths | 1,845 sq.ft.

$324,000

Airbnb cash on cash: N/A

Traditional cash on cash: 6.25%

Airbnb Rental Income: $null

Traditional Rental Income: $2710

Airbnb ROI: N/A

Traditional ROI: 6.25%

441 S Reynolds Rd Rd

Winslow, ME

2 beds | 1 baths | 720 sq.ft.

$179,000

Airbnb cash on cash: 3.68%

Traditional cash on cash: 9.37%

Airbnb Rental Income: $1568

Traditional Rental Income: $2088

Airbnb ROI: 3.68%

Traditional ROI: 9.37%

3 Blue Heron Ln

Winslow, ME

1 beds | 1 baths | 634 sq.ft.

$275,000

Airbnb cash on cash: -0.67%

Traditional cash on cash: 4.34%

Airbnb Rental Income: $916

Traditional Rental Income: $1985

Airbnb ROI: -0.67%