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
2 Pat Dr Middleton, MA 2 Pat Dr, Middleton, MA 01923 \| Single Family Residential	3 beds \| 2 baths \| 2,625 sq.ft.	$1,118,888	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.99% Airbnb Rental Income: $2363 Traditional Rental Income: $3438 Airbnb ROI: -0.6% Traditional ROI: 0.99%
267 Centre St Middleton, MA 267 Centre St, Middleton, MA 01923 \| Other	N/A beds \| N/A baths \| N/A	$499,999	Airbnb cash on cash: -0.04% Traditional cash on cash: 1.08% Airbnb Rental Income: $1559 Traditional Rental Income: $1638 Airbnb ROI: -0.04% Traditional ROI: 1.08%
360 Andover St #1310 Middleton, MA 360 Andover St #1310, Middleton, MA 01923 \| Townhouse	3 beds \| 2 baths \| 1,336 sq.ft.	$649,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 2.29% Airbnb Rental Income: $2363 Traditional Rental Income: $3305 Airbnb ROI: -0.23% Traditional ROI: 2.29%
123 Forest St Middleton, MA Rare opportunity to secure 1.5 acres of land in a prime Middleton location with limited co...	2 beds \| 1 baths \| 1,120 sq.ft.	$600,000	Airbnb cash on cash: -0.37% Traditional cash on cash: 1.87% Airbnb Rental Income: $1607 Traditional Rental Income: $2402 Airbnb ROI: -0.37% Traditional ROI: 1.87%
Investment Properties for Sale in Other Cities of Massachusetts
11 Robinwood Ave Boston , MA Right in the heart of Jamaica Plain, just steps from Jamaica Pond and the vibrant shops & ...	5 beds \| 4 baths \| 3,390 sq.ft.	$2,399,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $4593 Airbnb ROI: N/A Traditional ROI: 0.27%
121 Portland St #505 Boston , MA 121 Portland St #505, Boston, MA 02114 \| Condo/Coop	1 beds \| 1 baths \| 481 sq.ft.	$575,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 0.77% Airbnb Rental Income: $4476 Traditional Rental Income: $2212 Airbnb ROI: 3.25% Traditional ROI: 0.77%
112 Roslindale Ave #2 Boston , MA 112 Roslindale Ave #2, Boston, MA 02131 \| Condo/Coop	3 beds \| 2 baths \| 1,183 sq.ft.	$599,900	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.76% Airbnb Rental Income: $3257 Traditional Rental Income: $3187 Airbnb ROI: 1.58% Traditional ROI: 2.76%
32 Lime St Boston , MA	4 beds \| 5 baths \| 5,194 sq.ft.	$9,450,000	Airbnb cash on cash: -1.66% Traditional cash on cash: -1.48% Airbnb Rental Income: $6280 Traditional Rental Income: $6608 Airbnb ROI: -1.66% Traditional ROI: -1.48%
78 Hutchings St #1 Boston , MA 78 Hutchings St #1, Boston, MA 02121 \| Condo/Coop	3 beds \| 2 baths \| 1,837 sq.ft.	$599,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 3.2% Airbnb Rental Income: $3221 Traditional Rental Income: $3338 Airbnb ROI: 1.7% Traditional ROI: 3.2%
280 Beacon St #1 Boston , MA 280 Beacon St #1, Boston, MA 02116 \| Condo/Coop	1 beds \| 1 baths \| 685 sq.ft.	$699,000	Airbnb cash on cash: -1.25% Traditional cash on cash: -0.33% Airbnb Rental Income: $1893 Traditional Rental Income: $1986 Airbnb ROI: -1.25% Traditional ROI: -0.33%
2 Larose Pl #13 Boston , MA 2 Larose Pl #13, Boston, MA 02135 \| Condo/Coop	2 beds \| 1 baths \| 735 sq.ft.	$529,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.91% Airbnb Rental Income: $1502 Traditional Rental Income: $2121 Airbnb ROI: -1.23% Traditional ROI: 0.91%
75 Burbank St #501 Boston , MA 75 Burbank St #501, Boston, MA 02115 \| Condo/Coop	1 beds \| 1 baths \| 425 sq.ft.	$496,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.75% Airbnb Rental Income: $2175 Traditional Rental Income: $1833 Airbnb ROI: 0.29% Traditional ROI: 0.75%
28-32 Atlantic Ave #424 Boston , MA 28-32 Atlantic Ave #424, Boston, MA 02110 \| Condo/Coop	2 beds \| 1 baths \| 1,023 sq.ft.	$1,370,000	Airbnb cash on cash: -1.8% Traditional cash on cash: -1.87% Airbnb Rental Income: $3073 Traditional Rental Income: $2284 Airbnb ROI: -1.8% Traditional ROI: -1.87%
125 Bay Road Eastham , MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| 2 baths \| 1,662 sq.ft.	$2,195,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.17% Airbnb Rental Income: $2826 Traditional Rental Income: $3577 Airbnb ROI: -0.52% Traditional ROI: 0.17%
496 Shore Road unit: 21 #21 Truro , MA The Captains Quarters, is the most sought after '' YEAR ROUND'', rental and investment pro...	3 beds \| 2 baths \| 2,018 sq.ft.	$1,299,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.78% Airbnb Rental Income: $2850 Traditional Rental Income: $3609 Airbnb ROI: -0.4% Traditional ROI: 0.78%
15 Shannon Road Harwich , MA Step into this beautifully renovated 3 bed 2 bath home featuring a brand-new kitchen and b...	3 beds \| 2 baths \| 1,124 sq.ft.	$629,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 3.49% Airbnb Rental Income: $3107 Traditional Rental Income: $3001 Airbnb ROI: 2.47% Traditional ROI: 3.49%
73 Joshua Jethro Road Chatham , MA PERFECT HOUSE FOR A POOL! Located in Chatham's highly sought after Riverbay Estates commun...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,520,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 1.11% Airbnb Rental Income: $2063 Traditional Rental Income: $3418 Airbnb ROI: -0.23% Traditional ROI: 1.11%
1 Franklin St Ph 4E Boston , MA 1 Franklin St Ph 4E, Boston, MA 02110 \| Condo/Coop	3 beds \| 4 baths \| 3,435 sq.ft.	$7,495,000	Airbnb cash on cash: -2.98% Traditional cash on cash: -2.56% Airbnb Rental Income: $3038 Traditional Rental Income: $5277 Airbnb ROI: -2.98% Traditional ROI: -2.56%
5 Great Hills Road Truro , MA Discover a perfect seaside retreat in this light-filled contemporary home, water views gre...	5 beds \| 3 baths \| 2,456 sq.ft.	$1,799,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.87% Airbnb Rental Income: $1633 Traditional Rental Income: $4180 Airbnb ROI: -0.93% Traditional ROI: 0.87%

Real Estate investment in Middleton, MA

There are 4 properties for sale in the city of Middleton . The median list price in Middleton is $624,500 and the average price per square foot is $369. In December 2025, the average monthly cash on cash return in Middleton is 1.00%. The average monthly rental income in Middleton is $2,854.

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

There are 4 investment properties available for sale in Middleton.

In 2025, the best neighborhood to buy investment property is Middleton.

The ROI for Short-Term is higher than the Long-Term in Middleton with average rental income of $1,985.

Your search for investment property begins and ends here

Investment Property for Sale in Middleton, MA

2 Pat Dr

Middleton, MA

3 beds | 2 baths | 2,625 sq.ft.

$1,118,888

Airbnb cash on cash: -0.6%

Traditional cash on cash: 0.99%

Airbnb Rental Income: $2363

Traditional Rental Income: $3438

Airbnb ROI: -0.6%

Traditional ROI: 0.99%

267 Centre St

Middleton, MA

N/A beds | N/A baths | N/A

$499,999

Airbnb cash on cash: -0.04%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $1559

Traditional Rental Income: $1638

Airbnb ROI: -0.04%

Traditional ROI: 1.08%

360 Andover St #1310

Middleton, MA

3 beds | 2 baths | 1,336 sq.ft.

$649,000

Airbnb cash on cash: -0.23%

Traditional cash on cash: 2.29%

Airbnb Rental Income: $2363

Traditional Rental Income: $3305

Airbnb ROI: -0.23%

Traditional ROI: 2.29%

123 Forest St

Middleton, MA

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

$600,000

Airbnb cash on cash: -0.37%

Traditional cash on cash: 1.87%

Airbnb Rental Income: $1607

Traditional Rental Income: $2402

Airbnb ROI: -0.37%

Traditional ROI: 1.87%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

5 beds | 4 baths | 3,390 sq.ft.

$2,399,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.27%

Airbnb Rental Income: $null

Traditional Rental Income: $4593

Airbnb ROI: N/A

Traditional ROI: 0.27%

Boston , MA

1 beds | 1 baths | 481 sq.ft.

$575,000

Airbnb cash on cash: 3.25%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $4476

Traditional Rental Income: $2212

Airbnb ROI: 3.25%

Traditional ROI: 0.77%

Boston , MA

3 beds | 2 baths | 1,183 sq.ft.

$599,900

Airbnb cash on cash: 1.58%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $3257

Traditional Rental Income: $3187

Airbnb ROI: 1.58%

Traditional ROI: 2.76%

Boston , MA

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

$9,450,000

Airbnb cash on cash: -1.66%

Traditional cash on cash: -1.48%

Airbnb Rental Income: $6280

Traditional Rental Income: $6608

Airbnb ROI: -1.66%

Traditional ROI: -1.48%

Boston , MA

3 beds | 2 baths | 1,837 sq.ft.