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
236 Thomas St Middleboro, MA BACK ON MARKET-BUYER'S LOSS, YOUR GAIN! This fully updated 3-bedroom, 1.5-bath home offers...	3 beds \| 2 baths \| 1,639 sq.ft.	$549,900	Airbnb cash on cash: N/A Traditional cash on cash: 4.09% Airbnb Rental Income: $null Traditional Rental Income: $3283 Airbnb ROI: N/A Traditional ROI: 4.09%
663 Wareham Street #6 Middleboro, MA Welcome to Stonebridge Condominiumâone of Middleboroâs most sought-after communitiesâ...	2 beds \| 2 baths \| 1,712 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $2958 Airbnb ROI: N/A Traditional ROI: 3.09%
425 A Wareham Street 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%
3905 Pheasant Ln Middleboro, MA 3905 Pheasant Ln, Middleboro, MA 02346 \| Single Family Residential	2 beds \| 2 baths \| 1,600 sq.ft.	$415,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.49% Airbnb Rental Income: $null Traditional Rental Income: $3010 Airbnb ROI: N/A Traditional ROI: 2.49%
503 Hastings Rd Middleboro, MA 503 Hastings Rd, Middleboro, MA 02346 \| Single Family Residential	2 beds \| 2 baths \| 1,620 sq.ft.	$395,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.6% Airbnb Rental Income: $null Traditional Rental Income: $2962 Airbnb ROI: N/A Traditional ROI: 2.6%
39 Riverside Dr #39 Middleboro, MA 39 Riverside Dr #39, Middleboro, MA 02347 \| Condo/Coop	3 beds \| 2 baths \| 1,428 sq.ft.	$499,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.64% Airbnb Rental Income: $null Traditional Rental Income: $3581 Airbnb ROI: N/A Traditional ROI: 4.64%
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%
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%
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%
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%
240 N Main St Middleboro, MA 240 N Main St, Middleboro, MA 02346 \| Multi Family	4 beds \| 2 baths \| 2,258 sq.ft.	$525,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.77% Airbnb Rental Income: $null Traditional Rental Income: $3521 Airbnb ROI: N/A Traditional ROI: 4.77%
806 Waverly Street Middleboro, MA Welcome to this beautifully maintained single-level Carlisle Ranch, tucked in the sought-a...	3 beds \| 2 baths \| 1,456 sq.ft.	$400,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.27% Airbnb Rental Income: $null Traditional Rental Income: $3204 Airbnb ROI: N/A Traditional ROI: 3.27%
135 East Grove St Middleboro, MA 135 East Grove St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,600 sq.ft.	$429,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.82% Airbnb Rental Income: $null Traditional Rental Income: $3332 Airbnb ROI: N/A Traditional ROI: 5.82%
2602 Pheasant Middleboro, MA 2602 Pheasant, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,802 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $3258 Airbnb ROI: N/A Traditional ROI: 2.79%
302 Wood St Middleboro, MA Brand NEW CONSTRUCTION! Featuring 3 spacious bedrooms and 2.5 baths, this home showcases q...	3 beds \| 3 baths \| 1,768 sq.ft.	$729,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.9% Airbnb Rental Income: $null Traditional Rental Income: $3672 Airbnb ROI: N/A Traditional ROI: 2.9%
226 Cedar Street Middleboro, MA Experience the perfect balance of elegance and comfort in this exceptional home featuring ...	4 beds \| 3 baths \| 2,754 sq.ft.	$1,035,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.48% Airbnb Rental Income: $null Traditional Rental Income: $4624 Airbnb ROI: N/A Traditional ROI: 2.48%
620 Plymouth St Middleboro, MA 620 Plymouth St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 1 baths \| 2,084 sq.ft.	$639,900	Airbnb cash on cash: N/A Traditional cash on cash: 2.19% Airbnb Rental Income: $null Traditional Rental Income: $2728 Airbnb ROI: N/A Traditional ROI: 2.19%
162 East Grove St Middleboro, MA 162 East Grove St, Middleboro, MA 02346 \| Other	N/A beds \| N/A baths \| N/A	$4,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.9% Airbnb Rental Income: $null Traditional Rental Income: $1453 Airbnb ROI: N/A Traditional ROI: -1.9%
312 Wood St Middleboro, MA TO BE BUILT! Featuring 3 spacious bedrooms and 2.5 baths, this home showcases quality con...	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%
48 Cross St Middleboro, MA 48 Cross St, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 2,170 sq.ft.	$669,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $3221 Airbnb ROI: N/A Traditional ROI: 2.79%
12 Surrey Dr Middleboro, MA 12 Surrey Dr, Middleboro, MA 02347 \| Single Family Residential	4 beds \| 3 baths \| 2,790 sq.ft.	$815,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $4452 Airbnb ROI: N/A Traditional ROI: 3.52%
3402 Island Dr Middleboro, MA 3402 Island Dr, Middleboro, MA 02346 \| Single Family Residential	3 beds \| 2 baths \| 1,344 sq.ft.	$369,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.52% Airbnb Rental Income: $null Traditional Rental Income: $3135 Airbnb ROI: N/A Traditional ROI: 3.52%
18 Leilo Dr #18 Middleboro, MA 18 Leilo Dr #18, Middleboro, MA 02346 \| Townhouse	3 beds \| 1 baths \| 1,328 sq.ft.	$420,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.28% Airbnb Rental Income: $null Traditional Rental Income: $2648 Airbnb ROI: N/A Traditional ROI: 3.28%

Real Estate investment in Middleboro, MA

There are 26 properties for sale in the city of Middleboro . The median list price in Middleboro is $549,900 and the average price per square foot is $296. In December 2025, the average monthly cash on cash return in Middleboro is 3.00%. The average monthly rental income in Middleboro is $3,258.

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

There are 26 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

236 Thomas St

Middleboro, MA

3 beds | 2 baths | 1,639 sq.ft.

$549,900

Airbnb cash on cash: N/A

Traditional cash on cash: 4.09%

Airbnb Rental Income: $null

Traditional Rental Income: $3283

Airbnb ROI: N/A

Traditional ROI: 4.09%

663 Wareham Street #6

Middleboro, MA

2 beds | 2 baths | 1,712 sq.ft.

$429,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.09%

Airbnb Rental Income: $null

Traditional Rental Income: $2958

Airbnb ROI: N/A

Traditional ROI: 3.09%

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%

3905 Pheasant Ln

Middleboro, MA

2 beds | 2 baths | 1,600 sq.ft.

$415,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.49%

Airbnb Rental Income: $null

Traditional Rental Income: $3010

Airbnb ROI: N/A

Traditional ROI: 2.49%

503 Hastings Rd

Middleboro, MA

2 beds | 2 baths | 1,620 sq.ft.

$395,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.6%

Airbnb Rental Income: $null

Traditional Rental Income: $2962

Airbnb ROI: N/A

Traditional ROI: 2.6%

39 Riverside Dr #39

Middleboro, MA

3 beds | 2 baths | 1,428 sq.ft.

$499,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.64%

Airbnb Rental Income: $null

Traditional Rental Income: $3581

Airbnb ROI: N/A

Traditional ROI: 4.64%

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%

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