Real Estate Investment Properties for Sale in Winthrop, ME

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
144 Heritage Woods Ln Winthrop, ME Brand new kitchen!! Recently updated 2 bed 1 bath home with 60 feet of deep-water frontage...	2 beds \| 1 baths \| 930 sq.ft.	$615,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.05% Airbnb Rental Income: $1438 Traditional Rental Income: $1690 Airbnb ROI: -0.14% Traditional ROI: 1.05%
256 Narrows Pond Rd Winthrop, ME Move right into this beautifully updated and meticulously maintained Colonial, where moder...	3 beds \| 3 baths \| 2,204 sq.ft.	$459,900	Airbnb cash on cash: 2.31% Traditional cash on cash: 6.8% Airbnb Rental Income: $2445 Traditional Rental Income: $3784 Airbnb ROI: 2.31% Traditional ROI: 6.8%
85 Woods Grove Ln Winthrop, ME What an incredible location. Last house in and own the whole point. 672' of waterfron...	3 beds \| 2 baths \| 1,800 sq.ft.	$725,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.68% Airbnb Rental Income: $2445 Traditional Rental Income: $2064 Airbnb ROI: 0.36% Traditional ROI: 0.68%
161 Pamela Dr Winthrop, ME Welcome to this charming Cape Cod-style home in a sought-after neighborhood in Winthrop --...	3 beds \| 2 baths \| 1,350 sq.ft.	$320,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 9.01% Airbnb Rental Income: $2445 Traditional Rental Income: $3393 Airbnb ROI: 3.88% Traditional ROI: 9.01%
28 Beechwood Drive Winthrop, ME Tucked into one of the area's most desirable neighborhoods, this beautifully updated raise...	4 beds \| 1 baths \| 1,332 sq.ft.	$362,000	Airbnb cash on cash: 5.14% Traditional cash on cash: 6.85% Airbnb Rental Income: $3172 Traditional Rental Income: $3036 Airbnb ROI: 5.14% Traditional ROI: 6.85%
337 Route 133 Winthrop, ME Here is an opportunity to one of the most historic homes in the town of Winthrop, Maine. F...	5 beds \| 2 baths \| 2,759 sq.ft.	$669,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 4.16% Airbnb Rental Income: $2297 Traditional Rental Income: $3669 Airbnb ROI: 1.05% Traditional ROI: 4.16%
38 S Upper Narrows Ln Winthrop, ME Nestled on the shores of beautiful Upper Narrows Pond, this stunning waterfront home at 38...	2 beds \| 2 baths \| 2,387 sq.ft.	$799,900	Airbnb cash on cash: -0.58% Traditional cash on cash: 1.21% Airbnb Rental Income: $1438 Traditional Rental Income: $2350 Airbnb ROI: -0.58% Traditional ROI: 1.21%
89 Boot Cove Ln Winthrop, ME Welcome to 89 Boot Cove Lane, where privacy, comfort, and year-round waterfront living com...	4 beds \| 3 baths \| 2,054 sq.ft.	$629,000	Airbnb cash on cash: 2.37% Traditional cash on cash: 2.77% Airbnb Rental Income: $3172 Traditional Rental Income: $2688 Airbnb ROI: 2.37% Traditional ROI: 2.77%
64 Pineland Dr Winthrop, ME 64 Pineland Dr, Winthrop, ME 04364 \| Single Family Residential	2 beds \| 2 baths \| 840 sq.ft.	$99,900	Airbnb cash on cash: 1.99% Traditional cash on cash: 8.13% Airbnb Rental Income: $1438 Traditional Rental Income: $1606 Airbnb ROI: 1.99% Traditional ROI: 8.13%
974 Sturtevant Hill Rd Winthrop, ME 974 Sturtevant Hill Rd, Winthrop, ME 04364 \| Single Family Residential	4 beds \| 2 baths \| 3,081 sq.ft.	$465,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 3.06% Airbnb Rental Income: $3172 Traditional Rental Income: $2447 Airbnb ROI: 3.08% Traditional ROI: 3.06%
0 Us-202 Winthrop, ME 0 Us-202, Winthrop, ME 04364 \| Other	N/A beds \| N/A baths \| N/A	$99,000	Airbnb cash on cash: 5.5% Traditional cash on cash: 11.58% Airbnb Rental Income: $1242 Traditional Rental Income: $1432 Airbnb ROI: 5.5% Traditional ROI: 11.58%
247 Winthrop Center Rd Winthrop, ME Fantastic New Price! Historic Winthrop Gem Full of Character & Opportunity! If you've been...	3 beds \| 1 baths \| 2,312 sq.ft.	$295,000	Airbnb cash on cash: 5.3% Traditional cash on cash: 10.26% Airbnb Rental Income: $2445 Traditional Rental Income: $3225 Airbnb ROI: 5.3% Traditional ROI: 10.26%
41 Birch St Winthrop, ME Well-maintained 3-bedroom, 2-bath Cape situated on a private 1.62-acre lot on a public dea...	3 beds \| 2 baths \| 1,850 sq.ft.	$399,900	Airbnb cash on cash: 3.67% Traditional cash on cash: 7.94% Airbnb Rental Income: $2445 Traditional Rental Income: $3448 Airbnb ROI: 3.67% Traditional ROI: 7.94%
260 Narrows Pond Rd Winthrop, ME Quality-built and low maintenance, this charming two-bedroom, one-bath home offers comfort...	2 beds \| 1 baths \| 1,120 sq.ft.	$339,900	Airbnb cash on cash: 1.85% Traditional cash on cash: 6.02% Airbnb Rental Income: $1438 Traditional Rental Income: $2339 Airbnb ROI: 1.85% Traditional ROI: 6.02%
1 Black Island & 93 Birchwood Ln Winthrop, ME Having been in the same family since the early 1900s, Black Island on Cobbossee Lake is fo...	3 beds \| 1 baths \| 1,350 sq.ft.	$995,000	Airbnb cash on cash: -0.6% Traditional cash on cash: -0.28% Airbnb Rental Income: $2445 Traditional Rental Income: $2143 Airbnb ROI: -0.6% Traditional ROI: -0.28%
77 Wedgewood Dr Winthrop, ME 77 Wedgewood Dr, Winthrop, ME 04364 \| Single Family Residential	3 beds \| 2 baths \| 2,835 sq.ft.	$595,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 1.2% Airbnb Rental Income: $2445 Traditional Rental Income: $2064 Airbnb ROI: 0.81% Traditional ROI: 1.2%
172 Turkey Ln Winthrop, ME 172 Turkey Ln, Winthrop, ME 04364 \| Single Family Residential	3 beds \| 2 baths \| 1,598 sq.ft.	$220,000	Airbnb cash on cash: 6.09% Traditional cash on cash: 7.12% Airbnb Rental Income: $2445 Traditional Rental Income: $2064 Airbnb ROI: 6.09% Traditional ROI: 7.12%
57 Metcalf Rd Winthrop, ME 57 Metcalf Rd, Winthrop, ME 04364 \| Single Family Residential	4 beds \| 3 baths \| 2,124 sq.ft.	$450,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 3.24% Airbnb Rental Income: $3172 Traditional Rental Income: $2447 Airbnb ROI: 3.26% Traditional ROI: 3.24%
229 Route 133 Winthrop, ME 229 Route 133, Winthrop, ME 04364 \| Single Family Residential	5 beds \| 2 baths \| 2,647 sq.ft.	$750,000	Airbnb cash on cash: -0.02% Traditional cash on cash: 2.64% Airbnb Rental Income: $2297 Traditional Rental Income: $3584 Airbnb ROI: -0.02% Traditional ROI: 2.64%
7 & 11 Keyes Landing Ln Winthrop, ME 7 & 11 Keyes Landing Ln, Winthrop, ME 04364 \| Single Family Residential	3 beds \| 2 baths \| 1,597 sq.ft.	$1,200,000	Airbnb cash on cash: -0.78% Traditional cash on cash: -0.59% Airbnb Rental Income: $2445 Traditional Rental Income: $2064 Airbnb ROI: -0.78% Traditional ROI: -0.59%
537 Winthrop Center Rd Winthrop, ME 537 Winthrop Center Rd, Winthrop, ME 04364 \| Manufactured Home	4 beds \| 2 baths \| 2,128 sq.ft.	$449,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 3.25% Airbnb Rental Income: $3172 Traditional Rental Income: $2447 Airbnb ROI: 3.27% Traditional ROI: 3.25%

Real Estate investment in Winthrop, ME

There are 21 properties for sale in the city of Winthrop . The median list price in Winthrop is $599,641 and the average price per square foot is $325. In September 2026, the average monthly cash on cash return in Winthrop is 4.00%. The average monthly rental income in Winthrop is $2,447.

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

There are 21 investment properties available for sale in Winthrop.

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

The ROI for Long-Term is higher than the Short-Term in Winthrop with average rental income of $2,447.

Your search for investment property begins and ends here

Investment Property for Sale in Winthrop, ME

144 Heritage Woods Ln

Winthrop, ME

2 beds | 1 baths | 930 sq.ft.

$615,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 1.05%

Airbnb Rental Income: $1438

Traditional Rental Income: $1690

Airbnb ROI: -0.14%

Traditional ROI: 1.05%

256 Narrows Pond Rd

Winthrop, ME

3 beds | 3 baths | 2,204 sq.ft.

$459,900

Airbnb cash on cash: 2.31%

Traditional cash on cash: 6.8%

Airbnb Rental Income: $2445

Traditional Rental Income: $3784

Airbnb ROI: 2.31%

Traditional ROI: 6.8%

85 Woods Grove Ln

Winthrop, ME

3 beds | 2 baths | 1,800 sq.ft.

$725,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 0.68%

Airbnb Rental Income: $2445

Traditional Rental Income: $2064

Airbnb ROI: 0.36%

Traditional ROI: 0.68%

161 Pamela Dr

Winthrop, ME

3 beds | 2 baths | 1,350 sq.ft.

$320,000

Airbnb cash on cash: 3.88%

Traditional cash on cash: 9.01%

Airbnb Rental Income: $2445

Traditional Rental Income: $3393

Airbnb ROI: 3.88%

Traditional ROI: 9.01%

28 Beechwood Drive

Winthrop, ME

4 beds | 1 baths | 1,332 sq.ft.

$362,000

Airbnb cash on cash: 5.14%

Traditional cash on cash: 6.85%

Airbnb Rental Income: $3172

Traditional Rental Income: $3036

Airbnb ROI: 5.14%

Traditional ROI: 6.85%

337 Route 133

Winthrop, ME

5 beds | 2 baths | 2,759 sq.ft.

$669,000

Airbnb cash on cash: 1.05%

Traditional cash on cash: 4.16%

Airbnb Rental Income: $2297

Traditional Rental Income: $3669

Airbnb ROI: 1.05%

Traditional ROI: 4.16%

38 S Upper Narrows Ln

Winthrop, ME

2 beds | 2 baths | 2,387 sq.ft.

$799,900

Airbnb cash on cash: -0.58%

Traditional cash on cash: 1.21%

Airbnb Rental Income: $1438

Traditional Rental Income: $2350

Airbnb ROI: -0.58%

Traditional ROI: 1.21%

89 Boot Cove Ln

Winthrop, ME

4 beds | 3 baths | 2,054 sq.ft.

$629,000

Airbnb cash on cash: 2.37%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $3172

Traditional Rental Income: $2688

Airbnb ROI: 2.37%