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
66 Forest St Middleboro, MA Buy through Auction.com. This foreclosure property is a great opportunity to invest in thi...	3 beds \| 2 baths \| 1,122 sq.ft.	$489,999	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $2924 Airbnb ROI: N/A Traditional ROI: 4.32%
425 A Wareham Street Middleboro, MA General Use & Single Family Zoning with 15.3 acres. This parcel includes a single-family ...	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%
162 Plympton St Middleboro, MA Undeniably one of Middleboro's finest properties, a former parcel of the Eddy Homestead ju...	3 beds \| 3 baths \| 3,010 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.73% Airbnb Rental Income: $null Traditional Rental Income: $3951 Airbnb ROI: N/A Traditional ROI: 1.73%
91 Brookside Dr Middleboro, MA Set on a serene 1.84-acre lot in a picturesque neighborhood, this spacious Colonial offers...	5 beds \| 3 baths \| 3,824 sq.ft.	$849,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.24% Airbnb Rental Income: $null Traditional Rental Income: $4363 Airbnb ROI: N/A Traditional ROI: 3.24%
29 Beach St Middleboro, MA Back on Market due to financing. Enjoy over 8 Acres of complete privacy in this Cape Cod...	3 beds \| 2 baths \| 1,884 sq.ft.	$669,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $3366 Airbnb ROI: N/A Traditional ROI: 3.39%
Lot1 Elk Run Drive Middleboro, MA ** NEW CONSTRUCTION at Elk Run Estates --Plans are in!! There is still time for special re...	4 beds \| 3 baths \| 2,300 sq.ft.	$1,089,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.02% Airbnb Rental Income: $null Traditional Rental Income: $4186 Airbnb ROI: N/A Traditional ROI: 3.02%
571 Wareham Street Middleboro, MA Step into this antique farmhouse where classic charm meets thoughtful updates. New windows...	3 beds \| 2 baths \| 1,612 sq.ft.	$489,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.67% Airbnb Rental Income: $null Traditional Rental Income: $3262 Airbnb ROI: N/A Traditional ROI: 4.67%
2804 Island Drive Middleboro, MA Welcome to carefree living in this beautifully maintained ranch-style home in a desirable ...	2 beds \| 2 baths \| 1,698 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.92% Airbnb Rental Income: $null Traditional Rental Income: $2994 Airbnb ROI: N/A Traditional ROI: 5.92%
1606 Fox Run Middleboro, MA Welcome to Oak Point, a premier 55+ community for active adults. This well-maintained, one...	2 beds \| 2 baths \| 1,646 sq.ft.	$375,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.19% Airbnb Rental Income: $null Traditional Rental Income: $3049 Airbnb ROI: N/A Traditional ROI: 3.19%
45 North Street Middleboro, MA Welcome Home to 45 North St! This spacious 3-bedroom, 2.5-bath home offers the perfect ble...	3 beds \| 3 baths \| 2,197 sq.ft.	$649,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.02% Airbnb Rental Income: $null Traditional Rental Income: $3902 Airbnb ROI: N/A Traditional ROI: 4.02%
145 Everett St Middleboro, MA 145 Everett St, Middleboro, MA 02346 \| Single Family Residential	4 beds \| 2 baths \| 2,290 sq.ft.	$679,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.3% Airbnb Rental Income: $null Traditional Rental Income: $3592 Airbnb ROI: N/A Traditional ROI: 3.3%
8 Clayton Rd Middleboro, MA 8 Clayton Rd, Middleboro, MA 02346 \| Single Family Residential	2 beds \| 1 baths \| 1,322 sq.ft.	$474,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.01% Airbnb Rental Income: $null Traditional Rental Income: $2414 Airbnb ROI: N/A Traditional ROI: 3.01%
14 Pineridge Way unit: 14 #14 Middleboro, MA 14 Pine Ridge Way U:14, a delightful condominium located in Middleboro, MA. This inviting ...	3 beds \| N/A baths \| 1,910 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.63% Airbnb Rental Income: $null Traditional Rental Income: $2749 Airbnb ROI: N/A Traditional ROI: 4.63%
114 Oak St Middleboro, MA 114 Oak St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,818 sq.ft.	$569,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.75% Airbnb Rental Income: $null Traditional Rental Income: $3271 Airbnb ROI: N/A Traditional ROI: 3.75%
22 Keith St #22 Middleboro, MA 22 Keith St #22, Middleboro, MA 02346 \| Condo/Coop	2 beds \| 1 baths \| 1,420 sq.ft.	$276,216	Airbnb cash on cash: N/A Traditional cash on cash: 6.54% Airbnb Rental Income: $null Traditional Rental Income: $2614 Airbnb ROI: N/A Traditional ROI: 6.54%
306 Wood St Middleboro, MA Brand NEW CONSTRUCTION! This stunning Colonial offers the perfect blend of modern efficien...	3 beds \| 3 baths \| 1,768 sq.ft.	$724,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $3788 Airbnb ROI: N/A Traditional ROI: 3.25%
124 Ashley Ln #12-4 Middleboro, MA 124 Ashley Ln #12-4, Middleboro, MA 02346 \| Townhouse	2 beds \| 1 baths \| 1,902 sq.ft.	$449,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.97% Airbnb Rental Income: $null Traditional Rental Income: $2195 Airbnb ROI: N/A Traditional ROI: 0.97%
7 Myrtle St Middleboro, MA 7 Myrtle St, Middleboro, MA 02346 \| Single Family Residential	4 beds \| 2 baths \| 1,485 sq.ft.	$354,900	Airbnb cash on cash: N/A Traditional cash on cash: 8.31% Airbnb Rental Income: $null Traditional Rental Income: $3603 Airbnb ROI: N/A Traditional ROI: 8.31%
77 Millstone Ln Middleboro, MA 77 Millstone Ln, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,768 sq.ft.	$672,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $3321 Airbnb ROI: N/A Traditional ROI: 2.93%
10 Corinne Pkwy Middleboro, MA Discover the charm of one-level* living in this beautifully updated 2â3 bedroom cottage ...	3 beds \| 1 baths \| 1,186 sq.ft.	$435,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.83% Airbnb Rental Income: $null Traditional Rental Income: $2520 Airbnb ROI: N/A Traditional ROI: 3.83%

Real Estate investment in Middleboro, MA

There are 22 properties for sale in the city of Middleboro . The median list price in Middleboro is $539,900 and the average price per square foot is $295. In October 2025, the average monthly cash on cash return in Middleboro is 3.00%. The average monthly rental income in Middleboro is $3,262.

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

There are 22 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

66 Forest St

Middleboro, MA

3 beds | 2 baths | 1,122 sq.ft.

$489,999

Airbnb cash on cash: N/A

Traditional cash on cash: 4.32%

Airbnb Rental Income: $null

Traditional Rental Income: $2924

Airbnb ROI: N/A

Traditional ROI: 4.32%

425 A Wareham Street

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%

162 Plympton St

Middleboro, MA

3 beds | 3 baths | 3,010 sq.ft.

$1,150,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.73%

Airbnb Rental Income: $null

Traditional Rental Income: $3951

Airbnb ROI: N/A

Traditional ROI: 1.73%

91 Brookside Dr

Middleboro, MA

5 beds | 3 baths | 3,824 sq.ft.

$849,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.24%

Airbnb Rental Income: $null

Traditional Rental Income: $4363

Airbnb ROI: N/A

Traditional ROI: 3.24%

29 Beach St

Middleboro, MA

3 beds | 2 baths | 1,884 sq.ft.

$669,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.39%

Airbnb Rental Income: $null

Traditional Rental Income: $3366

Airbnb ROI: N/A

Traditional ROI: 3.39%

Lot1 Elk Run Drive

Middleboro, MA

4 beds | 3 baths | 2,300 sq.ft.

$1,089,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.02%

Airbnb Rental Income: $null

Traditional Rental Income: $4186

Airbnb ROI: N/A

Traditional ROI: 3.02%

571 Wareham Street

Middleboro, MA

3 beds | 2 baths | 1,612 sq.ft.

$489,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.67%

Airbnb Rental Income: $null

Traditional Rental Income: $3262

Airbnb ROI: N/A

Traditional ROI: 4.67%

2804 Island Drive

Middleboro, MA

2 beds | 2 baths | 1,698 sq.ft.

$429,900

Airbnb cash on cash: N/A

Traditional cash on cash: 5.92%

Airbnb Rental Income: $null

Traditional Rental Income: $2994

Airbnb ROI: N/A