Real Estate Investment Properties for Sale in Middleboro, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
89 West St Middleboro, MA Investor and homebuyer opportunity! This property was recently foreclosed upon and is now ...	2 beds \| 2 baths \| 1,228 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.1% Airbnb Rental Income: $null Traditional Rental Income: $2791 Airbnb ROI: N/A Traditional ROI: 4.1%
480 Wareham St Middleboro, MA 480 Wareham St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$1,650,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.34% Airbnb Rental Income: $null Traditional Rental Income: $1453 Airbnb ROI: N/A Traditional ROI: -1.34%
45 Forest St Middleboro, MA 45 Forest St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,794 sq.ft.	$569,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 3.78% Airbnb Rental Income: $3505 Traditional Rental Income: $3284 Airbnb ROI: 2.74% Traditional ROI: 3.78%
73 Wareham St Middleboro, MA 73 Wareham St, Middleboro, MA 02346 \| Single Family Residential	4 beds \| 3 baths \| 2,693 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.56% Airbnb Rental Income: $null Traditional Rental Income: $4205 Airbnb ROI: N/A Traditional ROI: 4.56%
4 Star Ave Middleboro, MA 4 Star Ave, Middleboro, MA 02346 \| Single Family Residential	4 beds \| 2 baths \| 2,240 sq.ft.	$599,800	Airbnb cash on cash: N/A Traditional cash on cash: 3.85% Airbnb Rental Income: $null Traditional Rental Income: $3650 Airbnb ROI: N/A Traditional ROI: 3.85%
194 Bedford St Middleboro, MA 194 Bedford St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: -0.3% Airbnb Rental Income: $null Traditional Rental Income: $1434 Airbnb ROI: N/A Traditional ROI: -0.3%
441 Wareham St Middleboro, MA 441 Wareham St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.1% Airbnb Rental Income: $null Traditional Rental Income: $1502 Airbnb ROI: N/A Traditional ROI: 0.1%
0 Wareham/miller St Middleboro, MA 80 Miller St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.01% Airbnb Rental Income: $null Traditional Rental Income: $1505 Airbnb ROI: N/A Traditional ROI: -1.01%
Wood St lot: A Middleboro, MA TO BE BUILT - HOUSE PACKAGE - 2100sq.ft+ Colonial. 4 bedrooms 2 1/2 baths. Farmers Porch. ...	4 beds \| 3 baths \| 2,100 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.35% Airbnb Rental Income: $null Traditional Rental Income: $1529 Airbnb ROI: N/A Traditional ROI: -0.35%
2602 Green St Middleboro, MA 2602 Green St, Middleboro, MA 02346 \| Single Family Residential	2 beds \| 2 baths \| 1,680 sq.ft.	$365,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.46% Airbnb Rental Income: $null Traditional Rental Income: $3091 Airbnb ROI: N/A Traditional ROI: 3.46%
52 Saddleworth Way Middleboro, MA 52 Saddleworth Way, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,992 sq.ft.	$775,900	Airbnb cash on cash: 1.39% Traditional cash on cash: 2.24% Airbnb Rental Income: $3505 Traditional Rental Income: $3349 Airbnb ROI: 1.39% Traditional ROI: 2.24%
Rear Wareham St Middleboro, MA Rear Wareham St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| 1,836 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.02% Airbnb Rental Income: $null Traditional Rental Income: $1492 Airbnb ROI: N/A Traditional ROI: -1.02%
37 Rocky Gutter St Middleboro, MA 37 Rocky Gutter St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$898,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.59% Airbnb Rental Income: $null Traditional Rental Income: $1461 Airbnb ROI: N/A Traditional ROI: -0.59%
53 West St Middleboro, MA 53 West St, Middleboro, MA 02346 \| Single Family Residential	4 beds \| 1 baths \| 1,840 sq.ft.	$519,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.73% Airbnb Rental Income: $null Traditional Rental Income: $2980 Airbnb ROI: N/A Traditional ROI: 3.73%
42 Everett St Middleboro, MA 42 Everett St, Middleboro, MA 02346 \| Multi Family	4 beds \| 2 baths \| 1,762 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.65% Airbnb Rental Income: $null Traditional Rental Income: $3520 Airbnb ROI: N/A Traditional ROI: 3.65%
386 Wareham St Middleboro, MA 386 Wareham St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$275,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.03% Airbnb Rental Income: $null Traditional Rental Income: $1453 Airbnb ROI: N/A Traditional ROI: 3.03%
218 Old Center St Middleboro, MA 218 Old Center St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$120,000	Airbnb cash on cash: N/A Traditional cash on cash: 9.54% Airbnb Rental Income: $null Traditional Rental Income: $1453 Airbnb ROI: N/A Traditional ROI: 9.54%
0 Murdock St Middleboro, MA 0 Murdock St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$445,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.15% Airbnb Rental Income: $null Traditional Rental Income: $1497 Airbnb ROI: N/A Traditional ROI: 1.15%
958 Centre St Middleboro, MA 958 Centre St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,526 sq.ft.	$469,000	Airbnb cash on cash: 3.79% Traditional cash on cash: 4.84% Airbnb Rental Income: $3505 Traditional Rental Income: $3194 Airbnb ROI: 3.79% Traditional ROI: 4.84%
17 School St Middleboro, MA 17 School St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 1 baths \| 1,300 sq.ft.	$399,999	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.42% Airbnb Rental Income: $3505 Traditional Rental Income: $2584 Airbnb ROI: 4.82% Traditional ROI: 4.42%
LOT 9 Christina Way Middleboro, MA LOT 9 Christina Way, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$299,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.78% Airbnb Rental Income: $null Traditional Rental Income: $1499 Airbnb ROI: N/A Traditional ROI: 2.78%
64 Rocky Meadow St Middleboro, MA 64 Rocky Meadow St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$199,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.3% Airbnb Rental Income: $null Traditional Rental Income: $1512 Airbnb ROI: N/A Traditional ROI: 5.3%
663 Wareham St #11 Middleboro, MA 663 Wareham St #11, Middleboro, MA 02346 \| Townhouse	2 beds \| 1 baths \| 1,608 sq.ft.	$419,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.94% Airbnb Rental Income: $null Traditional Rental Income: $2418 Airbnb ROI: N/A Traditional ROI: 1.94%
89 School St Middleboro, MA Charming and move-in ready Cape-style home offering 4 bedrooms, 2 updated baths, and a spa...	4 beds \| 2 baths \| 1,778 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $3592 Airbnb ROI: N/A Traditional ROI: 4.41%
5604 Oak Point Dr Middleboro, MA 5604 Oak Point Dr, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,612 sq.ft.	$465,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 2.68% Airbnb Rental Income: $3505 Traditional Rental Income: $3309 Airbnb ROI: 1.35% Traditional ROI: 2.68%
36 Spruce Middleboro, MA 36 Spruce, Middleboro, MA 02344 \| Single Family Residential	5 beds \| 3 baths \| 2,382 sq.ft.	$724,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.38% Airbnb Rental Income: $null Traditional Rental Income: $4558 Airbnb ROI: N/A Traditional ROI: 4.38%
10 Amanda St Middleboro, MA 10 Amanda St, Middleboro, MA 02346 \| Single Family Residential	4 beds \| 2 baths \| 3,073 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.26% Airbnb Rental Income: $null Traditional Rental Income: $3847 Airbnb ROI: N/A Traditional ROI: 2.26%
71 E Main St Middleboro, MA Set far back from the road on 2.3 acres, this beautifully maintained 3-4 bedroom Cape offe...	4 beds \| 2 baths \| 1,932 sq.ft.	$724,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.74% Airbnb Rental Income: $null Traditional Rental Income: $3922 Airbnb ROI: N/A Traditional ROI: 3.74%
65 Summer Street Middleboro, MA Step back in time with this enchanting 1740 antique where 18th-century grace meets modern ...	3 beds \| 2 baths \| 2,635 sq.ft.	$599,000	Airbnb cash on cash: 2.69% Traditional cash on cash: 3.73% Airbnb Rental Income: $3505 Traditional Rental Income: $3311 Airbnb ROI: 2.69% Traditional ROI: 3.73%
536 Plymouth St Middleboro, MA 536 Plymouth St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,972 sq.ft.	$799,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 2.05% Airbnb Rental Income: $3505 Traditional Rental Income: $3278 Airbnb ROI: 1.32% Traditional ROI: 2.05%
80 Pearl St Middleboro, MA 80 Pearl St, Middleboro, MA 02346 \| Multi Family	5 beds \| 3 baths \| 2,692 sq.ft.	$715,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 4.17% Airbnb Rental Income: $3505 Traditional Rental Income: $4354 Airbnb ROI: 1.74% Traditional ROI: 4.17%
233 Tispaquin St Middleboro, MA 233 Tispaquin St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 2,184 sq.ft.	$789,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 2.22% Airbnb Rental Income: $3505 Traditional Rental Income: $3380 Airbnb ROI: 1.34% Traditional ROI: 2.22%
47 Anderson Avenue Middleboro, MA Have you been searching for a move-in ready starter home in Middleboro? This adorable 2-be...	2 beds \| 1 baths \| 962 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.85% Airbnb Rental Income: $null Traditional Rental Income: $2219 Airbnb ROI: N/A Traditional ROI: 2.85%
317 W Grove St Middleboro, MA 317 W Grove St, Middleboro, MA 02346 \| Manufactured Home	2 beds \| 1 baths \| 938 sq.ft.	$349,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.16% Airbnb Rental Income: $null Traditional Rental Income: $2189 Airbnb ROI: N/A Traditional ROI: 4.16%
36 Spruce St Middleboro, MA 36 Spruce St, Middleboro, MA 02344 \| Multi Family	5 beds \| 3 baths \| 2,382 sq.ft.	$724,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $4180 Airbnb ROI: N/A Traditional ROI: 3.83%
49 Plain St Middleboro, MA Come home to a setting that feels like your own private retreat. Set on nearly 2 wooded ac...	3 beds \| 3 baths \| 2,486 sq.ft.	$799,900	Airbnb cash on cash: 1.43% Traditional cash on cash: 3.45% Airbnb Rental Income: $3505 Traditional Rental Income: $4236 Airbnb ROI: 1.43% Traditional ROI: 3.45%

Real Estate investment in Middleboro, MA

There are 51 properties for sale in the city of Middleboro . The median list price in Middleboro is $569,000 and the average price per square foot is $305. In July 2026, the average monthly cash on cash return in Middleboro is 3.00%. The average monthly rental income in Middleboro is $3,015.

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

There are 51 investment properties available for sale in Middleboro.

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

The ROI for Short-Term is higher than the Long-Term in Middleboro with average rental income of $3,505.

Your search for investment property begins and ends here

Investment Property for Sale in Middleboro, MA

89 West St

Middleboro, MA

2 beds | 2 baths | 1,228 sq.ft.

$499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.1%

Airbnb Rental Income: $null

Traditional Rental Income: $2791

Airbnb ROI: N/A

Traditional ROI: 4.1%

480 Wareham St

Middleboro, MA

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

$1,650,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.34%

Airbnb Rental Income: $null

Traditional Rental Income: $1453

Airbnb ROI: N/A

Traditional ROI: -1.34%

45 Forest St

Middleboro, MA

3 beds | 2 baths | 1,794 sq.ft.

$569,000

Airbnb cash on cash: 2.74%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $3505

Traditional Rental Income: $3284

Airbnb ROI: 2.74%

Traditional ROI: 3.78%

73 Wareham St

Middleboro, MA

4 beds | 3 baths | 2,693 sq.ft.

$649,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.56%

Airbnb Rental Income: $null

Traditional Rental Income: $4205

Airbnb ROI: N/A

Traditional ROI: 4.56%

4 Star Ave

Middleboro, MA

4 beds | 2 baths | 2,240 sq.ft.

$599,800

Airbnb cash on cash: N/A

Traditional cash on cash: 3.85%

Airbnb Rental Income: $null

Traditional Rental Income: $3650

Airbnb ROI: N/A

Traditional ROI: 3.85%

194 Bedford St

Middleboro, MA

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

$749,900

Airbnb cash on cash: N/A

Traditional cash on cash: -0.3%

Airbnb Rental Income: $null

Traditional Rental Income: $1434

Airbnb ROI: N/A

Traditional ROI: -0.3%

441 Wareham St

Middleboro, MA

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

$650,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.1%

Airbnb Rental Income: $null

Traditional Rental Income: $1502

Airbnb ROI: N/A

Traditional ROI: 0.1%

0 Wareham/miller St

Middleboro, MA

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

$1,250,000

Airbnb cash on cash: N/A

Traditional cash on cash: -1.01%

Airbnb Rental Income: $null

Traditional Rental Income: $1505

Airbnb ROI: N/A