Real Estate Investment Properties for Sale in Massachusetts

Looking for investment property in Massachusetts with high ROI ?

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

Q: Which city in Massachusetts to invest in for highest ROI on long term rental properties in 2026

In 2026, North Adamsis the best city to buy investment properties. Find more investment properties today!

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
588 S Orleans Road Orleans, MA Lush lawns and hydrangeas flanking a winding seashell driveway create a storybook entrance...	3 beds \| 3 baths \| 2,841 sq.ft.	$1,595,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 1.04% Airbnb Rental Income: $1488 Traditional Rental Income: $3944 Airbnb ROI: -0.92% Traditional ROI: 1.04%
61 Oak Hill Road Chatham, MA Easy one-floor living in Chatham can be yours in this sun-filled 2 bedroom home that inclu...	2 beds \| 2 baths \| 1,688 sq.ft.	$895,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 2.25% Airbnb Rental Income: $957 Traditional Rental Income: $3062 Airbnb ROI: -0.69% Traditional ROI: 2.25%
30 Orange St Fall River, MA This two-family townhouse-style home offers a versatile layout ideal for both investors an...	4 beds \| 2 baths \| 1,411 sq.ft.	$455,000	Airbnb cash on cash: 2.47% Traditional cash on cash: 5.74% Airbnb Rental Income: $2478 Traditional Rental Income: $3270 Airbnb ROI: 2.47% Traditional ROI: 5.74%
7915 Eastern Ave #1011 Washington, DC 7915 Eastern Ave #1011, Washington, DC 20910 \| Condo/Coop	2 beds \| 2 baths \| 1,032 sq.ft.	$365,000	Airbnb cash on cash: -3.1% Traditional cash on cash: 1.3% Airbnb Rental Income: $641 Traditional Rental Income: $1853 Airbnb ROI: -3.1% Traditional ROI: 1.3%
8005 13th St #411 Washington, DC 8005 13th St #411, Washington, DC 20910 \| Condo/Coop	1 beds \| 1 baths \| 1,039 sq.ft.	$325,000	Airbnb cash on cash: -2.21% Traditional cash on cash: 2.57% Airbnb Rental Income: $917 Traditional Rental Income: $2036 Airbnb ROI: -2.21% Traditional ROI: 2.57%
27 Whereaway Lane Wellfleet, MA PRIVATE OASIS! Set on over one private acre in the heart of Wellfleet, this beautifully pr...	4 beds \| 3 baths \| 2,343 sq.ft.	$1,495,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.54% Airbnb Rental Income: $2005 Traditional Rental Income: $4462 Airbnb ROI: -0.61% Traditional ROI: 1.54%
22 Bay View Road Truro, MA Set high above the shoreline with sweeping views of Cape Cod Bay, Provincetown and Highlan...	5 beds \| 5 baths \| 6,616 sq.ft.	$3,849,500	Airbnb cash on cash: -0.73% Traditional cash on cash: 0.45% Airbnb Rental Income: $3316 Traditional Rental Income: $6784 Airbnb ROI: -0.73% Traditional ROI: 0.45%
615 Chequessett Neck Road Wellfleet, MA Set on a prime stretch of Wellfleet harbor this striking beachfront home distills the very...	5 beds \| 5 baths \| 4,454 sq.ft.	$5,399,000	Airbnb cash on cash: -1.43% Traditional cash on cash: -0.31% Airbnb Rental Income: $2090 Traditional Rental Income: $7174 Airbnb ROI: -1.43% Traditional ROI: -0.31%
26 Ryder Road Harwich, MA This spacious 4-bdrm home offers multiple living areas with living room on 1st floor and f...	4 beds \| 2 baths \| 2,288 sq.ft.	$575,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 4.94% Airbnb Rental Income: $2416 Traditional Rental Income: $3556 Airbnb ROI: 1.71% Traditional ROI: 4.94%
120 Bearses Way Hyannis, MA Fall in love with this adorable 2-bedroom ranch perfectly situated in the heart of downtow...	2 beds \| 1 baths \| 480 sq.ft.	$369,900	Airbnb cash on cash: 0.57% Traditional cash on cash: 3.42% Airbnb Rental Income: $1226 Traditional Rental Income: $1822 Airbnb ROI: 0.57% Traditional ROI: 3.42%
10 Metropolitan Ave Ashland, MA Spacious 3 bed 2 bath home in a fabulous Ashland location, ready for its new owners! First...	3 beds \| 2 baths \| 1,779 sq.ft.	$550,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 4.28% Airbnb Rental Income: $1884 Traditional Rental Income: $3406 Airbnb ROI: 0.34% Traditional ROI: 4.28%
16 Meadowbank Rd Billerica, MA Opportunity knocks at 16 Meadowbank Road in Billerica! This spacious home is ready for its...	2 beds \| 2 baths \| 1,602 sq.ft.	$459,900	Airbnb cash on cash: -1.25% Traditional cash on cash: 4.76% Airbnb Rental Income: $802 Traditional Rental Income: $3064 Airbnb ROI: -1.25% Traditional ROI: 4.76%
2 Wallace Rd #Dh-B Stockbridge, MA Looking for one-level living in the heart of the Berkshires? Comfort, convenience and move...	1 beds \| 1 baths \| 658 sq.ft.	$278,800	Airbnb cash on cash: 1.06% Traditional cash on cash: 4.2% Airbnb Rental Income: $1259 Traditional Rental Income: $1684 Airbnb ROI: 1.06% Traditional ROI: 4.2%
18 Highcrest Rd Lenox, MA Condo at Twelve Oaks Village. End of Cul-de-sac with Mountain views. This unit offers lots...	4 beds \| 5 baths \| 2,691 sq.ft.	$1,279,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 3.02% Airbnb Rental Income: $1494 Traditional Rental Income: $5526 Airbnb ROI: -0.74% Traditional ROI: 3.02%
35 Bayshore Drive Mashpee, MA Set along the marshfront with views of Hamblin Pond, this beautiful home offers a peaceful...	4 beds \| 4 baths \| 3,236 sq.ft.	$1,395,500	Airbnb cash on cash: -0.86% Traditional cash on cash: 2.63% Airbnb Rental Income: $1314 Traditional Rental Income: $5443 Airbnb ROI: -0.86% Traditional ROI: 2.63%
9 Burt St Acushnet, MA Welcome to 9 Burt St. - a stunning updated cape tucked into one of Acushnet's most desirab...	3 beds \| 2 baths \| 2,285 sq.ft.	$545,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 4.4% Airbnb Rental Income: $856 Traditional Rental Income: $3276 Airbnb ROI: -1.01% Traditional ROI: 4.4%
724 Commercial Street Provincetown, MA Welcome to Seaview House, an extraordinary coastal retreat offering sweeping, unobstructed...	4 beds \| 4 baths \| 4,277 sq.ft.	$3,700,000	Airbnb cash on cash: -1% Traditional cash on cash: 0.21% Airbnb Rental Income: $1742 Traditional Rental Income: $5417 Airbnb ROI: -1% Traditional ROI: 0.21%
4 Clement Street Sandwich, MA Nestled on a quiet cul-de-sac in historic Sandwich Village, this charming, sun-filled Cape...	3 beds \| 2 baths \| 1,428 sq.ft.	$649,900	Airbnb cash on cash: -0.39% Traditional cash on cash: 3.06% Airbnb Rental Income: $1419 Traditional Rental Income: $3087 Airbnb ROI: -0.39% Traditional ROI: 3.06%
173 Hillsdale Rd Egremont, MA Surrounded on three sides by Nature Conservancy-protected land, 173 Hillsdale Road is one ...	5 beds \| 5 baths \| 4,842 sq.ft.	$2,000,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 2.32% Airbnb Rental Income: $3786 Traditional Rental Income: $7316 Airbnb ROI: -0.03% Traditional ROI: 2.32%
497 S Main St Great Barrington, MA Multi-family in a convenient location, walking distance to town and shopping, bus line nea...	3 beds \| 3 baths \| 2,480 sq.ft.	$465,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 6.57% Airbnb Rental Income: $2423 Traditional Rental Income: $3914 Airbnb ROI: 1.78% Traditional ROI: 6.57%
25 Whitney Pond Rd Groton, MA Your dream waterfront property awaits on Whitney Pond-a hidden gem, tucked away in a quiet...	2 beds \| 2 baths \| 1,257 sq.ft.	$599,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 3.13% Airbnb Rental Income: $1331 Traditional Rental Income: $3065 Airbnb ROI: -0.7% Traditional ROI: 3.13%
28 Ellsworth Street Medford, MA Welcome to this classic 3-bedroom, 1.5-bath bungalow offering timeless character and a gre...	3 beds \| 2 baths \| 1,323 sq.ft.	$749,900	Airbnb cash on cash: -0.04% Traditional cash on cash: 2.4% Airbnb Rental Income: $1792 Traditional Rental Income: $3007 Airbnb ROI: -0.04% Traditional ROI: 2.4%
240 Bradford Street #3 Provincetown, MA This 1,588 sq ft standalone cottage offers the rare combination of privacy, comfort, and c...	1 beds \| 2 baths \| 1,696 sq.ft.	$1,395,000	Airbnb cash on cash: -1.17% Traditional cash on cash: 0.26% Airbnb Rental Income: $1138 Traditional Rental Income: $2618 Airbnb ROI: -1.17% Traditional ROI: 0.26%
59 Olympia Ave #4 SHREWSBURY, MA Beautiful townhouse in the heart of Shrewsbury! Enjoy urban-style living in a suburban set...	3 beds \| 3 baths \| 1,833 sq.ft.	$749,900	Airbnb cash on cash: -0.29% Traditional cash on cash: 3.45% Airbnb Rental Income: $2084 Traditional Rental Income: $4157 Airbnb ROI: -0.29% Traditional ROI: 3.45%
28 Arthur St unit: 3 Beverly, MA Welcome to the heart of highly sought-after Beverly! This bright, pet-friendly top-level 2...	2 beds \| 1 baths \| 873 sq.ft.	$449,900	Airbnb cash on cash: 0.08% Traditional cash on cash: 2.44% Airbnb Rental Income: $1720 Traditional Rental Income: $2238 Airbnb ROI: 0.08% Traditional ROI: 2.44%
159 Wilder Road Bolton, MA Captivating Shaker Reproduction Colonial set well back on one of Bolton's most scenic road...	4 beds \| 3 baths \| 3,585 sq.ft.	$1,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.89% Airbnb Rental Income: $null Traditional Rental Income: $4364 Airbnb ROI: N/A Traditional ROI: 1.89%
176 Beacon Street South Yarmouth, MA This charming and move-in-ready home offers the perfect blend of comfort and style. Enjoy ...	2 beds \| 2 baths \| 1,473 sq.ft.	$739,000	Airbnb cash on cash: -0.49% Traditional cash on cash: 2.72% Airbnb Rental Income: $1227 Traditional Rental Income: $3049 Airbnb ROI: -0.49% Traditional ROI: 2.72%
679 N Falmouth Highway North Falmouth, MA This four-bedroom, two-bath Cape in North Falmouth offers easy access to Megansett Beach, ...	4 beds \| 2 baths \| 1,758 sq.ft.	$769,000	Airbnb cash on cash: 0.12% Traditional cash on cash: 3.21% Airbnb Rental Income: $1792 Traditional Rental Income: $3517 Airbnb ROI: 0.12% Traditional ROI: 3.21%
92 Prospect Street Lunenburg, MA OPEN HOUSE CANCELLED You've seen this one - the pretty yellow hip roof colonial at 92 Pros...	4 beds \| 3 baths \| 2,508 sq.ft.	$650,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.49% Airbnb Rental Income: $null Traditional Rental Income: $4360 Airbnb ROI: N/A Traditional ROI: 4.49%
11 Bramblewood St Bridgewater, MA OPEN HOUSE 6/10 from 11-1 PM! PRICE REDUCED!! YOU DESERVE TO LIVE THIS WELL!! NEW to the ...	4 beds \| 2 baths \| 2,539 sq.ft.	$830,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.08% Airbnb Rental Income: $null Traditional Rental Income: $3884 Airbnb ROI: N/A Traditional ROI: 3.08%
23 Palmer St #1 WALTHAM, MA Stunning 2016-built townhouse offering the perfect blend of modern design, comfort, and co...	4 beds \| 3 baths \| 1,961 sq.ft.	$949,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.77% Airbnb Rental Income: $3089 Traditional Rental Income: $4370 Airbnb ROI: 0.52% Traditional ROI: 2.77%
3 Caileigh Ct #3 Andover, MA Desirable Lincoln Woods Condominium in a prime location with close proximity to schools, c...	2 beds \| 3 baths \| 2,638 sq.ft.	$999,900	Airbnb cash on cash: -2.23% Traditional cash on cash: 0.79% Airbnb Rental Income: $1351 Traditional Rental Income: $3743 Airbnb ROI: -2.23% Traditional ROI: 0.79%
30 Norris Path Teaticket, MA Half a mile from Great Pond and just minutes to Bristol Beach, this spacious Falmouth home...	5 beds \| 4 baths \| 3,056 sq.ft.	$1,100,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 2.9% Airbnb Rental Income: $2625 Traditional Rental Income: $4511 Airbnb ROI: 0.44% Traditional ROI: 2.9%
48 Vaughn Hill Rd Bolton, MA Charming southern-style Cape, privately set at the end of a drive on 4.5 acres with sweepi...	4 beds \| 4 baths \| 4,808 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.13% Airbnb Rental Income: $null Traditional Rental Income: $5503 Airbnb ROI: N/A Traditional ROI: 2.13%
20 Jessies Landing Chatham, MA Welcome to this beautifully crafted residence in Jessie's Landing, an exclusive Eastward C...	3 beds \| 4 baths \| 2,940 sq.ft.	$3,299,900	Airbnb cash on cash: -0.9% Traditional cash on cash: 0.37% Airbnb Rental Income: $1541 Traditional Rental Income: $4966 Airbnb ROI: -0.9% Traditional ROI: 0.37%
151 Hickory Lane Northbridge, MA OPEN HOUSE CANCELLED, OFFER ACCEPTED CUL-DE-SAC SERENITY MEETS EVERYDAY COMFORT! Perfe...	4 beds \| 4 baths \| 3,234 sq.ft.	$724,900	Airbnb cash on cash: N/A Traditional cash on cash: 6.1% Airbnb Rental Income: $null Traditional Rental Income: $5537 Airbnb ROI: N/A Traditional ROI: 6.1%

Real Estate investment in Massachusetts

There are 4,617 properties available for sale in the state of Massachusetts. North Adams, Spencer and Sutton are the best rental property markets in Massachusetts. The average median price of properties for sale in these cities are $240,283 and the average price per square foot is $0. Their average monthly cash on cash return is 12.00%.

Massachusetts Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 4,617 investment properties available for sale in Massachusetts.

In 2026, North Adams is the best city to buy investment properties. Find more investment properties today!

In 2026, North Adams (26%) and Spencer (5%) has the highest cash on cash return for long term rentals in Massachusetts.

Your search for investment property begins and ends here

Investment Property for Sale in Massachusetts

588 S Orleans Road

Orleans, MA

3 beds | 3 baths | 2,841 sq.ft.

$1,595,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $1488

Traditional Rental Income: $3944

Airbnb ROI: -0.92%

Traditional ROI: 1.04%

61 Oak Hill Road

Chatham, MA

2 beds | 2 baths | 1,688 sq.ft.

$895,000

Airbnb cash on cash: -0.69%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $957

Traditional Rental Income: $3062

Airbnb ROI: -0.69%

Traditional ROI: 2.25%

30 Orange St

Fall River, MA

4 beds | 2 baths | 1,411 sq.ft.

$455,000

Airbnb cash on cash: 2.47%

Traditional cash on cash: 5.74%

Airbnb Rental Income: $2478

Traditional Rental Income: $3270

Airbnb ROI: 2.47%

Traditional ROI: 5.74%

7915 Eastern Ave #1011

Washington, DC

2 beds | 2 baths | 1,032 sq.ft.

$365,000

Airbnb cash on cash: -3.1%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $641

Traditional Rental Income: $1853

Airbnb ROI: -3.1%

Traditional ROI: 1.3%

8005 13th St #411

Washington, DC

1 beds | 1 baths | 1,039 sq.ft.

$325,000

Airbnb cash on cash: -2.21%

Traditional cash on cash: 2.57%

Airbnb Rental Income: $917

Traditional Rental Income: $2036

Airbnb ROI: -2.21%

Traditional ROI: 2.57%

27 Whereaway Lane

Wellfleet, MA

4 beds | 3 baths | 2,343 sq.ft.

$1,495,000

Airbnb cash on cash: -0.61%

Traditional cash on cash: 1.54%

Airbnb Rental Income: $2005

Traditional Rental Income: $4462

Airbnb ROI: -0.61%

Traditional ROI: 1.54%

22 Bay View Road

Truro, MA

5 beds | 5 baths | 6,616 sq.ft.

$3,849,500

Airbnb cash on cash: -0.73%

Traditional cash on cash: 0.45%

Airbnb Rental Income: $3316

Traditional Rental Income: $6784

Airbnb ROI: -0.73%

Traditional ROI: 0.45%

615 Chequessett Neck Road

Wellfleet, MA

5 beds | 5 baths | 4,454 sq.ft.

$5,399,000

Airbnb cash on cash: -1.43%

Traditional cash on cash: -0.31%

Airbnb Rental Income: $2090

Traditional Rental Income: $7174

Airbnb ROI: -1.43%