Real Estate Investment Properties for Sale in Middleton, MA

Looking for investment property in Middleton, MA with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5 Wennerberg Road Middleton, MA Excellent Opportunity Awaits for this conveniently located property in desirable Middleton...	3 beds \| 2 baths \| 1,854 sq.ft.	$629,900	Airbnb cash on cash: 0.62% Traditional cash on cash: 4.41% Airbnb Rental Income: $2363 Traditional Rental Income: $4008 Airbnb ROI: 0.62% Traditional ROI: 4.41%
Investment Properties for Sale in Other Cities of Massachusetts
15 Blackwood St #1 Boston , MA 15 Blackwood St #1, Boston, MA 02115 \| Condo/Coop	2 beds \| 1 baths \| 1,132 sq.ft.	$849,000	Airbnb cash on cash: -0.89% Traditional cash on cash: -0.15% Airbnb Rental Income: $2387 Traditional Rental Income: $2385 Airbnb ROI: -0.89% Traditional ROI: -0.15%
40 Traveler St #507 Boston , MA Welcome to Siena Condominium, where modern city living meets elevated comfort. This south-...	1 beds \| 1 baths \| 741 sq.ft.	$780,000	Airbnb cash on cash: -1.54% Traditional cash on cash: 0.18% Airbnb Rental Income: $1891 Traditional Rental Income: $2633 Airbnb ROI: -1.54% Traditional ROI: 0.18%
772 E 6th St #1 Boston , MA Location Location!! Beautifully renovated in 2019 and meticulously maintained, this sunny ...	1 beds \| 2 baths \| 883 sq.ft.	$719,900	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.51% Airbnb Rental Income: $1803 Traditional Rental Income: $2062 Airbnb ROI: -0.6% Traditional ROI: 0.51%
99 E Brookline St #2 Boston , MA 99 E Brookline St #2, Boston, MA 02118 \| Condo/Coop	2 beds \| 1 baths \| 660 sq.ft.	$649,000	Airbnb cash on cash: 0.09% Traditional cash on cash: 0.57% Airbnb Rental Income: $2387 Traditional Rental Income: $2086 Airbnb ROI: 0.09% Traditional ROI: 0.57%
35 Fay St #202 Boston , MA 35 Fay St #202, Boston, MA 02118 \| Condo/Coop	1 beds \| 1 baths \| 1,004 sq.ft.	$775,000	Airbnb cash on cash: -1.82% Traditional cash on cash: -0.5% Airbnb Rental Income: $1753 Traditional Rental Income: $2228 Airbnb ROI: -1.82% Traditional ROI: -0.5%
32 Lime St Boston , MA	4 beds \| 5 baths \| 5,194 sq.ft.	$8,850,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.43% Airbnb Rental Income: $null Traditional Rental Income: $6608 Airbnb ROI: N/A Traditional ROI: -1.43%
15 Estrella St #1 Boston , MA 15 Estrella St #1, Boston, MA 02130 \| Condo/Coop	3 beds \| 1 baths \| 1,130 sq.ft.	$525,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 2.25% Airbnb Rental Income: $2817 Traditional Rental Income: $2677 Airbnb ROI: 1.2% Traditional ROI: 2.25%
11 Wayne St Boston , MA 11 Wayne St, Boston, MA 02121 \| Multi Family	6 beds \| 4 baths \| 4,819 sq.ft.	$1,350,000	Airbnb cash on cash: -1.63% Traditional cash on cash: 2.22% Airbnb Rental Income: $1225 Traditional Rental Income: $5664 Airbnb ROI: -1.63% Traditional ROI: 2.22%
198 Byron St Boston , MA 198 Byron St, Boston, MA 02128 \| Single Family Residential	3 beds \| 1 baths \| 2,385 sq.ft.	$1,150,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 0.22% Airbnb Rental Income: $2238 Traditional Rental Income: $2708 Airbnb ROI: -0.74% Traditional ROI: 0.22%
580 Washington St #1214 Boston , MA 580 Washington St #1214, Boston, MA 02111 \| Condo/Coop	1 beds \| 1 baths \| 799 sq.ft.	$895,000	Airbnb cash on cash: -1.67% Traditional cash on cash: -0.81% Airbnb Rental Income: $2152 Traditional Rental Income: $2321 Airbnb ROI: -1.67% Traditional ROI: -0.81%
13 Wellington St Boston , MA Beautiful townhouse on quiet, tree-lined street minutes from T, Prudential Center, Symphon...	4 beds \| 3 baths \| 3,110 sq.ft.	$3,675,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.4% Airbnb Rental Income: $2506 Traditional Rental Income: $4312 Airbnb ROI: -1.1% Traditional ROI: -0.4%
36 Martin St Boston , MA 36 Martin St, Boston, MA 02132 \| Single Family Residential	4 beds \| 1 baths \| 1,688 sq.ft.	$1,025,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.84% Airbnb Rental Income: $null Traditional Rental Income: $3011 Airbnb ROI: N/A Traditional ROI: 0.84%
1 Franklin St #1205 Boston , MA Move in and see why Millennium Tower Boston is the evolution of luxury residential living!...	2 beds \| 2 baths \| 1,161 sq.ft.	$1,675,000	Airbnb cash on cash: -2.15% Traditional cash on cash: 0.19% Airbnb Rental Income: $2517 Traditional Rental Income: $5552 Airbnb ROI: -2.15% Traditional ROI: 0.19%

Real Estate investment in Middleton, MA

There are 1 properties for sale in the city of Middleton . The median list price in Middleton is $549,990 and the average price per square foot is $234. In May 2026, the average monthly cash on cash return in Middleton is 4.00%. The average monthly rental income in Middleton is $4,008.

Middleton, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 1 investment properties available for sale in Middleton.

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

The ROI for Long-Term is higher than the Short-Term in Middleton with average rental income of $4,008.

Your search for investment property begins and ends here

Investment Property for Sale in Middleton, MA

5 Wennerberg Road

Middleton, MA

3 beds | 2 baths | 1,854 sq.ft.

$629,900

Airbnb cash on cash: 0.62%

Traditional cash on cash: 4.41%

Airbnb Rental Income: $2363

Traditional Rental Income: $4008

Airbnb ROI: 0.62%

Traditional ROI: 4.41%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

2 beds | 1 baths | 1,132 sq.ft.

$849,000

Airbnb cash on cash: -0.89%

Traditional cash on cash: -0.15%

Airbnb Rental Income: $2387

Traditional Rental Income: $2385

Airbnb ROI: -0.89%

Traditional ROI: -0.15%

Boston , MA

1 beds | 1 baths | 741 sq.ft.

$780,000

Airbnb cash on cash: -1.54%

Traditional cash on cash: 0.18%

Airbnb Rental Income: $1891

Traditional Rental Income: $2633

Airbnb ROI: -1.54%

Traditional ROI: 0.18%

Boston , MA

1 beds | 2 baths | 883 sq.ft.

$719,900

Airbnb cash on cash: -0.6%

Traditional cash on cash: 0.51%

Airbnb Rental Income: $1803

Traditional Rental Income: $2062

Airbnb ROI: -0.6%

Traditional ROI: 0.51%

Boston , MA

2 beds | 1 baths | 660 sq.ft.

$649,000

Airbnb cash on cash: 0.09%

Traditional cash on cash: 0.57%

Airbnb Rental Income: $2387

Traditional Rental Income: $2086

Airbnb ROI: 0.09%

Traditional ROI: 0.57%

Boston , MA

1 beds | 1 baths | 1,004 sq.ft.

$775,000

Airbnb cash on cash: -1.82%

Traditional cash on cash: -0.5%

Airbnb Rental Income: $1753

Traditional Rental Income: $2228

Airbnb ROI: -1.82%

Traditional ROI: -0.5%

Boston , MA

4 beds | 5 baths | 5,194 sq.ft.

$8,850,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.43%

Airbnb Rental Income: $null

Traditional Rental Income: $6608

Airbnb ROI: N/A

Traditional ROI: -1.43%

Boston , MA

3 beds | 1 baths | 1,130 sq.ft.

$525,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $2817

Traditional Rental Income: $2677

Airbnb ROI: 1.2%

Traditional ROI: 2.25%

Boston , MA

6 beds | 4 baths | 4,819 sq.ft.

$1,350,000

Airbnb cash on cash: -1.63%

Traditional cash on cash: 2.22%