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 2025

In 2025, North Adamsis the best city to buy investment properties. Find more investment properties today!

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
11 Robinwood Ave Boston, MA Right in the heart of Jamaica Plain, just steps from Jamaica Pond and the vibrant shops & ...	5 beds \| 4 baths \| 3,390 sq.ft.	$2,399,000	Airbnb cash on cash: -1.5% Traditional cash on cash: 0.27% Airbnb Rental Income: $991 Traditional Rental Income: $4593 Airbnb ROI: -1.5% Traditional ROI: 0.27%
125 Bay Road Eastham, MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| N/A baths \| 1,662 sq.ft.	$2,195,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 0.17% Airbnb Rental Income: $5959 Traditional Rental Income: $3577 Airbnb ROI: 0.76% Traditional ROI: 0.17%
496 Shore Road unit: 21 #21 Truro, MA The Captains Quarters, is the most sought after '' YEAR ROUND'', rental and investment pro...	3 beds \| 2 baths \| 2,018 sq.ft.	$1,350,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.71% Airbnb Rental Income: $4038 Traditional Rental Income: $3609 Airbnb ROI: 0.36% Traditional ROI: 0.71%
496 Shore Road unit: 16 #16 Truro, MA This '' rare'' two bed'' , two full bath, ''YEAR ROUND'', second floor, direct ocean front...	2 beds \| 2 baths \| 607 sq.ft.	$720,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 1.08% Airbnb Rental Income: $2819 Traditional Rental Income: $2420 Airbnb ROI: 0.69% Traditional ROI: 1.08%
195 Ellis Landing Road Brewster, MA Just steps to beautiful Cape Cod Bay, sun and fun in the sand, breathtaking sunsets ... yo...	2 beds \| 1 baths \| 828 sq.ft.	$1,150,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.19% Airbnb Rental Income: $3072 Traditional Rental Income: $2064 Airbnb ROI: 0.48% Traditional ROI: 0.19%
73 Joshua Jethro Road Chatham, MA PERFECT HOUSE FOR A POOL! Located in Chatham's highly sought after Riverbay Estates commun...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,570,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.04% Airbnb Rental Income: $6412 Traditional Rental Income: $3418 Airbnb ROI: 2.24% Traditional ROI: 1.04%
5 Great Hills Road Truro, MA Discover a perfect seaside retreat in this light-filled contemporary home, water views gre...	5 beds \| 3 baths \| 2,456 sq.ft.	$1,850,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.82% Airbnb Rental Income: $4353 Traditional Rental Income: $4180 Airbnb ROI: 0.39% Traditional ROI: 0.82%
3 Seagull Lane Harwich, MA This home is full of possibility! It has lots of Old World charm but tastefully updated wi...	4 beds \| 2 baths \| 2,218 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $3102 Airbnb ROI: N/A Traditional ROI: 2.59%
663 Crowells Bog Road Brewster, MA Expanded 4 bedroom Cape-style home ideally located between Sheep Pond and Long Pond in Bre...	4 beds \| 4 baths \| 3,738 sq.ft.	$1,589,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.01% Airbnb Rental Income: $6080 Traditional Rental Income: $5430 Airbnb ROI: 1.63% Traditional ROI: 2.01%
5 Glacier Drive Truro, MA Don't miss out on this beautifully renovated Cape Style home! This 3 bedroom home is move-...	3 beds \| N/A baths \| 1,734 sq.ft.	$989,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 1.93% Airbnb Rental Income: $4038 Traditional Rental Income: $3202 Airbnb ROI: 1.9% Traditional ROI: 1.93%
307 W Main Street unit: 7 #7 Hyannis, MA Colonial Court Condominiums-NOW Vacant, bright morning sun and affordable 2 bedroom, 1 bat...	2 beds \| 1 baths \| 824 sq.ft.	$275,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 4.41% Airbnb Rental Income: $2345 Traditional Rental Income: $2075 Airbnb ROI: 3.21% Traditional ROI: 4.41%
266 School Street Cotuit, MA This lovingly maintained cottage offers the perfect blend of Cape Cod charm and modern con...	2 beds \| 1 baths \| 1,000 sq.ft.	$625,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.8% Airbnb Rental Income: $2892 Traditional Rental Income: $2346 Airbnb ROI: 1.59% Traditional ROI: 1.8%
38 Indian Trail Chatham, MA BREATHTAKING SUNSETS OVER NANTUCKET SOUND. Perched above Buck's Creek with panoramic views...	4 beds \| 4 baths \| 3,878 sq.ft.	$4,750,000	Airbnb cash on cash: -0.28% Traditional cash on cash: 0.1% Airbnb Rental Income: $5632 Traditional Rental Income: $6165 Airbnb ROI: -0.28% Traditional ROI: 0.1%
8 Cottage Street Wareham, MA Can you picture window boxes filled with seasonal flowers and crushed shells framing the f...	3 beds \| 1 baths \| 964 sq.ft.	$350,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 4.85% Airbnb Rental Income: $2118 Traditional Rental Income: $2265 Airbnb ROI: 2.76% Traditional ROI: 4.85%
118 Driftwood Lane South Yarmouth, MA Cape Cod Luxury Waterfront Living on Follins Pond~Bass River! Imagine waking up to blue sk...	4 beds \| N/A baths \| 3,978 sq.ft.	$3,424,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.69% Airbnb Rental Income: $2497 Traditional Rental Income: $7060 Airbnb ROI: -0.94% Traditional ROI: 0.69%
35 Bayshore Drive Mashpee, MA Welcome to The Osprey-a stunning marshfront retreat overlooking the tranquil waters of Ham...	4 beds \| 4 baths \| 3,236 sq.ft.	$1,395,500	Airbnb cash on cash: 2.07% Traditional cash on cash: 2.65% Airbnb Rental Income: $5855 Traditional Rental Income: $5443 Airbnb ROI: 2.07% Traditional ROI: 2.65%
44 Franklin Street Provincetown, MA Rebuilt from the ground up, this West End gem is a rare find-crafted with intention, desig...	3 beds \| 4 baths \| 2,443 sq.ft.	$3,599,000	Airbnb cash on cash: -0.52% Traditional cash on cash: -0.11% Airbnb Rental Income: $3979 Traditional Rental Income: $4467 Airbnb ROI: -0.52% Traditional ROI: -0.11%
56 Goddard Memorial Dr Worcester, MA Welcome to this beautifully and move in ready attached single-family home, filled with nat...	3 beds \| 2 baths \| 1,702 sq.ft.	$380,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 7.07% Airbnb Rental Income: $2169 Traditional Rental Income: $3218 Airbnb ROI: 2.59% Traditional ROI: 7.07%
314 Cockle Cove Road South Chatham, MA Wake up to shimmering views of Nantucket Sound from your luxurious family compound, just s...	4 beds \| N/A baths \| 3,120 sq.ft.	$2,995,000	Airbnb cash on cash: -0.46% Traditional cash on cash: -0.1% Airbnb Rental Income: $3039 Traditional Rental Income: $3352 Airbnb ROI: -0.46% Traditional ROI: -0.1%
552 Orleans Road North Chatham, MA Chatham's Best-Priced Waterfront Home! Enjoy lovely views of Frost Fish Creek from this ch...	3 beds \| N/A baths \| 1,144 sq.ft.	$1,450,000	Airbnb cash on cash: -0.41% Traditional cash on cash: 0.81% Airbnb Rental Income: $1861 Traditional Rental Income: $2998 Airbnb ROI: -0.41% Traditional ROI: 0.81%
11 Pershing Drive East Falmouth, MA Welcome to this stylishly update 3 Bed/2 Bath split-leveled home offering bright, versatil...	3 beds \| 2 baths \| 1,656 sq.ft.	$724,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.22% Airbnb Rental Income: $null Traditional Rental Income: $3244 Airbnb ROI: N/A Traditional ROI: 3.22%
173 Hillsdale Rd Egremont, MA Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlif...	5 beds \| 5 baths \| 4,842 sq.ft.	$2,300,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 1.88% Airbnb Rental Income: $7612 Traditional Rental Income: $7316 Airbnb ROI: 1.34% Traditional ROI: 1.88%
35 Cobblestone Lane #35 Worcester, MA Updated townhome style condo in Quabbin Estates! Spacious first level with open floorplan ...	3 beds \| 3 baths \| 2,016 sq.ft.	$349,900	Airbnb cash on cash: 2.03% Traditional cash on cash: 8.52% Airbnb Rental Income: $2169 Traditional Rental Income: $3751 Airbnb ROI: 2.03% Traditional ROI: 8.52%
13 Old Colony Way Provincetown, MA This beautiful, centrally located single-family home has been lovingly updated with custom...	4 beds \| N/A baths \| 2,086 sq.ft.	$2,599,000	Airbnb cash on cash: -0.64% Traditional cash on cash: 0.13% Airbnb Rental Income: $2470 Traditional Rental Income: $3727 Airbnb ROI: -0.64% Traditional ROI: 0.13%
77 The Heights Mashpee, MA JUST REDUCED $200,000! Incredible opportunity to own a bright and airy golf front home in ...	4 beds \| N/A baths \| 3,808 sq.ft.	$1,795,000	Airbnb cash on cash: 0.37% Traditional cash on cash: 1.46% Airbnb Rental Income: $4714 Traditional Rental Income: $5550 Airbnb ROI: 0.37% Traditional ROI: 1.46%
56 Sherwood Road Harwich, MA Built in 1984, this 3-bedroom 2 bath ranch style home has lots to offer! Over 1200 square ...	3 beds \| 2 baths \| 1,744 sq.ft.	$695,000	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.35% Airbnb Rental Income: $3107 Traditional Rental Income: $3255 Airbnb ROI: 2.03% Traditional ROI: 3.35%
23 Zylpha Road Harwich Port, MA Nestled in the popular Campgrounds neighborhood in Harwich Port, this charm-filled Dutch g...	4 beds \| 2 baths \| 1,680 sq.ft.	$1,475,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 0.81% Airbnb Rental Income: $6449 Traditional Rental Income: $3279 Airbnb ROI: 2.2% Traditional ROI: 0.81%
81 Province Lands Road unit: 5 #5 Provincetown, MA This spacious 2-bedroom, 1.5-bath condo offers the perfect blend of comfort, convenience, ...	2 beds \| 2 baths \| 1,045 sq.ft.	$1,092,500	Airbnb cash on cash: 0.23% Traditional cash on cash: 0.52% Airbnb Rental Income: $3088 Traditional Rental Income: $2671 Airbnb ROI: 0.23% Traditional ROI: 0.52%
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.	$769,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 2.61% Airbnb Rental Income: $2074 Traditional Rental Income: $3049 Airbnb ROI: 0.51% Traditional ROI: 2.61%
2136 Winthrop St Dighton, MA Three Bedroom Executive Ranch provides single level living. Home Built in 2000. Central Ai...	3 beds \| 1 baths \| 2,072 sq.ft.	$599,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.83% Airbnb Rental Income: $null Traditional Rental Income: $2814 Airbnb ROI: N/A Traditional ROI: 2.83%
120 King St Raynham, MA Fully renovated in 2018, this home checks every box! Updates include new roof, siding, hug...	3 beds \| 2 baths \| 1,572 sq.ft.	$559,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.92% Airbnb Rental Income: $null Traditional Rental Income: $3178 Airbnb ROI: N/A Traditional ROI: 3.92%
297 Sheldon Rd Barre, MA NEW PRICE FOR QUICK SALE! This 2007-built house w/ 3.24 acres on a quiet road in Barre may...	3 beds \| 2 baths \| 1,456 sq.ft.	$405,000	Airbnb cash on cash: 0.25% Traditional cash on cash: 5.65% Airbnb Rental Income: $1418 Traditional Rental Income: $3043 Airbnb ROI: 0.25% Traditional ROI: 5.65%
8 Hatch Rd Medford, MA Elegant West Medford Colonial offering 3,000+ sf of refined living where timeless characte...	3 beds \| 4 baths \| 3,006 sq.ft.	$1,195,000	Airbnb cash on cash: -0.22% Traditional cash on cash: 2.74% Airbnb Rental Income: $2279 Traditional Rental Income: $4998 Airbnb ROI: -0.22% Traditional ROI: 2.74%
18 Coltsway 18 Wayland, MA This rare free-standing Stoneridge Village residence offers the privacy of a single-family...	3 beds \| 3 baths \| 2,010 sq.ft.	$861,900	Airbnb cash on cash: 1.27% Traditional cash on cash: 1.21% Airbnb Rental Income: $4701 Traditional Rental Income: $3680 Airbnb ROI: 1.27% Traditional ROI: 1.21%
80 Elmwood Rd Winchendon, MA Welcome to 80 Elmwood Rd! A beautifully maintained 3-bedroom, 2.5-bath young colonial buil...	3 beds \| 3 baths \| 1,768 sq.ft.	$455,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 6.37% Airbnb Rental Income: $3257 Traditional Rental Income: $3673 Airbnb ROI: 3.68% Traditional ROI: 6.37%
5 Depot Road Truro, MA Perched above Pamet River, this fully renovated antique exudes timeless charm. Once inside...	4 beds \| 3 baths \| 2,400 sq.ft.	$1,649,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 1.13% Airbnb Rental Income: $3618 Traditional Rental Income: $3966 Airbnb ROI: 0.38% Traditional ROI: 1.13%
16 Pine Ridge Rd Medford, MA Welcome to 16 Pine Ridge Road, a timeless Colonial style home offering the beauty and tran...	5 beds \| 4 baths \| 2,955 sq.ft.	$1,948,500	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.36% Airbnb Rental Income: $3621 Traditional Rental Income: $5538 Airbnb ROI: -0.14% Traditional ROI: 1.36%
70 Main St Egremont, MA Charming 1790 Historic Home in the Heart of South EgremontNestled on a picturesque 0.8-acr...	4 beds \| 2 baths \| 2,148 sq.ft.	$589,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 5.29% Airbnb Rental Income: $4620 Traditional Rental Income: $3802 Airbnb ROI: 5.03% Traditional ROI: 5.29%

Real Estate investment in Massachusetts

There are 4,214 properties available for sale in the state of Massachusetts. North Adams, Danvers and Boston are the best rental property markets in Massachusetts. The average median price of properties for sale in these cities are $590,483 and the average price per square foot is $0. Their average monthly cash on cash return is 5.33%.

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

There are 4,214 investment properties available for sale in Massachusetts.

In 2025, North Adams is the best city to buy investment properties. Find more investment properties today!

In 2025, North Adams (11%) and Danvers (3%) 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

11 Robinwood Ave

Boston, MA

5 beds | 4 baths | 3,390 sq.ft.

$2,399,000

Airbnb cash on cash: -1.5%

Traditional cash on cash: 0.27%

Airbnb Rental Income: $991

Traditional Rental Income: $4593

Airbnb ROI: -1.5%

Traditional ROI: 0.27%

125 Bay Road

Eastham, MA

3 beds | N/A baths | 1,662 sq.ft.

$2,195,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 0.17%

Airbnb Rental Income: $5959

Traditional Rental Income: $3577

Airbnb ROI: 0.76%

Traditional ROI: 0.17%

496 Shore Road unit: 21 #21

Truro, MA

3 beds | 2 baths | 2,018 sq.ft.

$1,350,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $4038

Traditional Rental Income: $3609

Airbnb ROI: 0.36%

Traditional ROI: 0.71%

496 Shore Road unit: 16 #16

Truro, MA

2 beds | 2 baths | 607 sq.ft.

$720,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $2819

Traditional Rental Income: $2420

Airbnb ROI: 0.69%

Traditional ROI: 1.08%

195 Ellis Landing Road

Brewster, MA

2 beds | 1 baths | 828 sq.ft.

$1,150,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $3072

Traditional Rental Income: $2064

Airbnb ROI: 0.48%

Traditional ROI: 0.19%

73 Joshua Jethro Road

Chatham, MA

3 beds | 2 baths | 2,307 sq.ft.

$1,570,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 1.04%

Airbnb Rental Income: $6412

Traditional Rental Income: $3418

Airbnb ROI: 2.24%

Traditional ROI: 1.04%

5 Great Hills Road

Truro, MA

5 beds | 3 baths | 2,456 sq.ft.

$1,850,000

Airbnb cash on cash: 0.39%

Traditional cash on cash: 0.82%

Airbnb Rental Income: $4353

Traditional Rental Income: $4180

Airbnb ROI: 0.39%

Traditional ROI: 0.82%

3 Seagull Lane

Harwich, MA

4 beds | 2 baths | 2,218 sq.ft.

$799,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.59%

Airbnb Rental Income: $null

Traditional Rental Income: $3102

Airbnb ROI: N/A