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
65 Oak St Middleboro, MA Fantastic opportunity to own a renovated two-family home with so much to offer, convenient...	7 beds \| 2 baths \| 2,214 sq.ft.	$699,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.51% Airbnb Rental Income: $null Traditional Rental Income: $3577 Airbnb ROI: N/A Traditional ROI: 3.51%
143 Plympton St Middleboro, MA Buy through Auction.com. This foreclosure property is a great opportunity to invest in thi...	3 beds \| 2 baths \| 2,008 sq.ft.	$436,800	Airbnb cash on cash: N/A Traditional cash on cash: 5.53% Airbnb Rental Income: $null Traditional Rental Income: $3296 Airbnb ROI: N/A Traditional ROI: 5.53%
358 Marion Rd Middleboro, MA OPEN HOUSE CANCELLED. Set back from the street on a beautiful and private 1.8-acre lot, th...	3 beds \| 3 baths \| 1,910 sq.ft.	$775,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.58% Airbnb Rental Income: $null Traditional Rental Income: $3390 Airbnb ROI: N/A Traditional ROI: 2.58%
425 A Wareham St Middleboro, MA General Use & Single Family Zoning with 15.2 acres. This parcel includes a single-family h...	3 beds \| 1 baths \| 810 sq.ft.	$1,190,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.69% Airbnb Rental Income: $null Traditional Rental Income: $2474 Airbnb ROI: N/A Traditional ROI: 0.69%
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%
8 Susan Ln Middleboro, MA WELCOME HOME to this charming Cape in desirable Middleboro! Nestled on a quiet street, thi...	4 beds \| 2 baths \| 1,658 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.73% Airbnb Rental Income: $null Traditional Rental Income: $3583 Airbnb ROI: N/A Traditional ROI: 4.73%
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%
15 E Grove St Middleboro, MA Welcome to 15 E Grove St, a beautifully maintained 4-bedroom, 2-bath Dutch Colonial. The m...	4 beds \| 2 baths \| 2,313 sq.ft.	$590,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.46% Airbnb Rental Income: $null Traditional Rental Income: $3679 Airbnb ROI: N/A Traditional ROI: 4.46%
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%
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%
308 Wood St Middleboro, MA TO BE BUILT - LOT 3! Featuring 3 spacious bedrooms and 2.5 baths, this home showcases qual...	3 beds \| 3 baths \| 1,768 sq.ft.	$719,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.02% Airbnb Rental Income: $null Traditional Rental Income: $3719 Airbnb ROI: N/A Traditional ROI: 3.02%
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%
53 Miller St Middleboro, MA This gambrel-style Colonial is situated on a busy street and offers a circular turnaround ...	3 beds \| 1 baths \| 1,584 sq.ft.	$355,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.15% Airbnb Rental Income: $null Traditional Rental Income: $2652 Airbnb ROI: N/A Traditional ROI: 5.15%
6 Rock St Middleboro, MA 6 Rock St, Middleboro, MA 02346 \| Single Family Residential	4 beds \| 1 baths \| 2,862 sq.ft.	$699,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $2947 Airbnb ROI: N/A Traditional ROI: 2.16%
0 Murdock St Middleboro, MA 0 Murdock St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.11% Airbnb Rental Income: $null Traditional Rental Income: $1497 Airbnb ROI: N/A Traditional ROI: 1.11%
958 Centre St Middleboro, MA 958 Centre St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,526 sq.ft.	$479,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.7% Airbnb Rental Income: $null Traditional Rental Income: $3194 Airbnb ROI: N/A Traditional ROI: 4.7%
12 Southwick St Middleboro, MA 12 Southwick St, Middleboro, MA 02346 \| Single Family Residential	5 beds \| 1 baths \| 1,784 sq.ft.	$449,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.53% Airbnb Rental Income: $null Traditional Rental Income: $2937 Airbnb ROI: N/A Traditional ROI: 4.53%
17 School St Middleboro, MA	3 beds \| 1 baths \| 1,300 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.69% Airbnb Rental Income: $null Traditional Rental Income: $2584 Airbnb ROI: N/A Traditional ROI: 3.69%
30 Millstone Ln Middleboro, MA 30 Millstone Ln, Middleboro, MA 02346 \| Single Family Residential	4 beds \| 2 baths \| 3,862 sq.ft.	$899,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.28% Airbnb Rental Income: $null Traditional Rental Income: $3858 Airbnb ROI: N/A Traditional ROI: 2.28%
33 Warren Ave Middleboro, MA Spacious, move-in ready ranch offering easy living! The open living room flows seamlessly ...	2 beds \| 1 baths \| 1,496 sq.ft.	$539,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.6% Airbnb Rental Income: $null Traditional Rental Income: $2443 Airbnb ROI: N/A Traditional ROI: 2.6%
106 Old East Grv Middleboro, MA 106 Old East Grv, Middleboro, MA 02346 \| Single Family Residential	2 beds \| 1 baths \| 1,475 sq.ft.	$490,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.84% Airbnb Rental Income: $null Traditional Rental Income: $2412 Airbnb ROI: N/A Traditional ROI: 2.84%
500 Wareham St Middleboro, MA 500 Wareham St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 2,000 sq.ft.	$599,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.53% Airbnb Rental Income: $null Traditional Rental Income: $3315 Airbnb ROI: N/A Traditional ROI: 3.53%
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%
305 Plymouth St Middleboro, MA 305 Plymouth St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 1 baths \| 1,498 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $2804 Airbnb ROI: N/A Traditional ROI: 3.3%
1 Carmen Park Dr Middleboro, MA 1 Carmen Park Dr, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 1 baths \| 1,629 sq.ft.	$540,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.14% Airbnb Rental Income: $null Traditional Rental Income: $2801 Airbnb ROI: N/A Traditional ROI: 3.14%
4 May Ave Middleboro, MA 4 May Ave, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 1 baths \| 1,596 sq.ft.	$499,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.58% Airbnb Rental Income: $null Traditional Rental Income: $2827 Airbnb ROI: N/A Traditional ROI: 3.58%
93 Ashley Ln #93 Middleboro, MA 93 Ashley Ln #93, Middleboro, MA 02346 \| Townhouse	2 beds \| 1 baths \| 1,674 sq.ft.	$405,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.1% Airbnb Rental Income: $null Traditional Rental Income: $2425 Airbnb ROI: N/A Traditional ROI: 2.1%
5 Oak St Middleboro, MA 5 Oak St, Middleboro, MA 02346 \| Multi Family	6 beds \| 3 baths \| 3,730 sq.ft.	$900,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.16% Airbnb Rental Income: $null Traditional Rental Income: $4603 Airbnb ROI: N/A Traditional ROI: 3.16%
49 Anderson Ave Middleboro, MA 49 Anderson Ave, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 1 baths \| 1,086 sq.ft.	$515,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.86% Airbnb Rental Income: $null Traditional Rental Income: $2538 Airbnb ROI: N/A Traditional ROI: 2.86%

Real Estate investment in Middleboro, MA

There are 36 properties for sale in the city of Middleboro . The median list price in Middleboro is $569,950 and the average price per square foot is $303. In April 2026, the average monthly cash on cash return in Middleboro is 3.00%. The average monthly rental income in Middleboro is $2,727.

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

There are 36 investment properties available for sale in Middleboro.

The ROI for Short-Term is higher than the Long-Term in Middleboro with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Middleboro, MA

65 Oak St

Middleboro, MA

7 beds | 2 baths | 2,214 sq.ft.

$699,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.51%

Airbnb Rental Income: $null

Traditional Rental Income: $3577

Airbnb ROI: N/A

Traditional ROI: 3.51%

143 Plympton St

Middleboro, MA

3 beds | 2 baths | 2,008 sq.ft.

$436,800

Airbnb cash on cash: N/A

Traditional cash on cash: 5.53%

Airbnb Rental Income: $null

Traditional Rental Income: $3296

Airbnb ROI: N/A

Traditional ROI: 5.53%

358 Marion Rd

Middleboro, MA

3 beds | 3 baths | 1,910 sq.ft.

$775,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.58%

Airbnb Rental Income: $null

Traditional Rental Income: $3390

Airbnb ROI: N/A

Traditional ROI: 2.58%

425 A Wareham St

Middleboro, MA

3 beds | 1 baths | 810 sq.ft.

$1,190,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.69%

Airbnb Rental Income: $null

Traditional Rental Income: $2474

Airbnb ROI: N/A

Traditional ROI: 0.69%

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%

8 Susan Ln

Middleboro, MA

4 beds | 2 baths | 1,658 sq.ft.

$549,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.73%

Airbnb Rental Income: $null

Traditional Rental Income: $3583

Airbnb ROI: N/A

Traditional ROI: 4.73%

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