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
199 State St #401 Boston, MA 199 State St #401, Boston, MA 02109 \| Condo/Coop	2 beds \| 2 baths \| 2,456 sq.ft.	$3,195,000	Airbnb cash on cash: -2.15% Traditional cash on cash: -2.01% Airbnb Rental Income: $3419 Traditional Rental Income: $3070 Airbnb ROI: -2.15% Traditional ROI: -2.01%
183-185A Massachusetts Ave #803 Boston, MA 183-185A Massachusetts Ave #803, Boston, MA 02115 \| Condo/Coop	2 beds \| 2 baths \| 1,220 sq.ft.	$1,695,000	Airbnb cash on cash: -1.9% Traditional cash on cash: -1.48% Airbnb Rental Income: $2889 Traditional Rental Income: $2872 Airbnb ROI: -1.9% Traditional ROI: -1.48%
40 Traveler St #507 Boston, MA Welcome to Siena Condominium, where modern city living meets elevated comfort. This south-...	1 beds \| 1 baths \| 741 sq.ft.	$710,000	Airbnb cash on cash: -1.36% Traditional cash on cash: 0.29% Airbnb Rental Income: $2077 Traditional Rental Income: $2633 Airbnb ROI: -1.36% Traditional ROI: 0.29%
10 Boylston Pl #10 Boston, MA 10 Boylston Pl #10, Boston, MA 02130 \| Townhouse	3 beds \| 2 baths \| 1,976 sq.ft.	$1,190,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 0.68% Airbnb Rental Income: $2858 Traditional Rental Income: $3660 Airbnb ROI: -0.65% Traditional ROI: 0.68%
1 Franklin St #5105 Boston, MA 1 Franklin St #5105, Boston, MA 02110 \| Condo/Coop	3 beds \| 3 baths \| 2,196 sq.ft.	$3,550,000	Airbnb cash on cash: -2.54% Traditional cash on cash: -2.3% Airbnb Rental Income: $4204 Traditional Rental Income: $4111 Airbnb ROI: -2.54% Traditional ROI: -2.3%
267 Middle St Weymouth, MA FRESHLY RE-MODELED Colonial right in the heart of Weymouth! This 20yrs young home has been...	3 beds \| 2 baths \| 1,872 sq.ft.	$675,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.73% Airbnb Rental Income: $2879 Traditional Rental Income: $2934 Airbnb ROI: 1.58% Traditional ROI: 2.73%
5 Moss Hill Rd Boston, MA 5 Moss Hill Rd, Boston, MA 02130 \| Single Family Residential	5 beds \| 4 baths \| 3,100 sq.ft.	$2,249,999	Airbnb cash on cash: N/A Traditional cash on cash: 0.4% Airbnb Rental Income: $null Traditional Rental Income: $5562 Airbnb ROI: N/A Traditional ROI: 0.4%
4 Mount Vernon Ave #3 Charlestown, MA 4 Mount Vernon Ave #3, Charlestown, MA 02129 \| Condo/Coop	2 beds \| 2 baths \| 1,332 sq.ft.	$1,350,000	Airbnb cash on cash: -0.79% Traditional cash on cash: -0.44% Airbnb Rental Income: $2899 Traditional Rental Income: $2662 Airbnb ROI: -0.79% Traditional ROI: -0.44%
19 Salem St #2 Charlestown, MA 19 Salem St #2, Charlestown, MA 02129 \| Condo/Coop	1 beds \| 1 baths \| 745 sq.ft.	$649,999	Airbnb cash on cash: -0.72% Traditional cash on cash: -0.29% Airbnb Rental Income: $1867 Traditional Rental Income: $1630 Airbnb ROI: -0.72% Traditional ROI: -0.29%
7 Marlborough St #1 Boston, MA 7 Marlborough St #1, Boston, MA 02116 \| Condo/Coop	4 beds \| 3 baths \| 2,179 sq.ft.	$4,375,000	Airbnb cash on cash: -2.02% Traditional cash on cash: -1.57% Airbnb Rental Income: $2911 Traditional Rental Income: $4053 Airbnb ROI: -2.02% Traditional ROI: -1.57%
58 High St #5 Charlestown, MA 58 High St #5, Charlestown, MA 02129 \| Condo/Coop	2 beds \| 2 baths \| 1,293 sq.ft.	$1,270,000	Airbnb cash on cash: -0.61% Traditional cash on cash: -0.3% Airbnb Rental Income: $2899 Traditional Rental Income: $2594 Airbnb ROI: -0.61% Traditional ROI: -0.3%
102 Prince Valley Road Truro, MA Tucked away on 3.01 acres in the heart of the Cape Cod National Seashore, this custom-buil...	3 beds \| 3 baths \| 1,615 sq.ft.	$1,395,000	Airbnb cash on cash: 0.58% Traditional cash on cash: 1% Airbnb Rental Income: $3482 Traditional Rental Income: $3253 Airbnb ROI: 0.58% Traditional ROI: 1%
12 Pond Street Chatham, MA Few homes command Oyster Pond like 12 Pond Street. Three soaring peaks, the center crowned...	4 beds \| 4 baths \| 4,512 sq.ft.	$6,575,000	Airbnb cash on cash: -0.77% Traditional cash on cash: -0.29% Airbnb Rental Income: $3457 Traditional Rental Income: $5620 Airbnb ROI: -0.77% Traditional ROI: -0.29%
15 Kenney St #2 Brookline, MA 15 Kenney St #2, Brookline, MA 02130 \| Condo/Coop	2 beds \| 1 baths \| 840 sq.ft.	$525,000	Airbnb cash on cash: 1.57% Traditional cash on cash: 1.28% Airbnb Rental Income: $2969 Traditional Rental Income: $2145 Airbnb ROI: 1.57% Traditional ROI: 1.28%
30 Orange St Fall River, MA Welcome to 30 Orange Street in Fall River This townhouse-style two-family property off...	4 beds \| 2 baths \| 1,411 sq.ft.	$409,000	Airbnb cash on cash: 7.84% Traditional cash on cash: 6.49% Airbnb Rental Income: $4770 Traditional Rental Income: $3270 Airbnb ROI: 7.84% Traditional ROI: 6.49%
7915 Eastern Ave #1011 Washington, DC 7915 Eastern Ave #1011, Washington, DC 20910 \| Condo/Coop	2 beds \| 2 baths \| 1,032 sq.ft.	$348,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 1.3% Airbnb Rental Income: $1668 Traditional Rental Income: $1853 Airbnb ROI: -0.6% 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: -2.12% Traditional cash on cash: 2.57% Airbnb Rental Income: $948 Traditional Rental Income: $2036 Airbnb ROI: -2.12% Traditional ROI: 2.57%
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.	$3,499,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.6% Airbnb Rental Income: $2398 Traditional Rental Income: $6784 Airbnb ROI: -0.93% Traditional ROI: 0.6%
85 Jennie Clark Road Eastham, MA A pristine Cape Cod sanctuary in a coveted Eastham neighborhood! Perfectly positioned on a...	3 beds \| 3 baths \| 1,705 sq.ft.	$999,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.88% Airbnb Rental Income: $null Traditional Rental Income: $3360 Airbnb ROI: N/A Traditional ROI: 1.88%
9 Wesquansett Road Orleans, MA NEW PRICE, NOW $125,000 BELOW ASSESSED VALUE! Priced now with future updates in mind, this...	4 beds \| 2 baths \| 1,972 sq.ft.	$825,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 2.24% Airbnb Rental Income: $2523 Traditional Rental Income: $3103 Airbnb ROI: 0.69% Traditional ROI: 2.24%
114 Old Jail Lane Barnstable, MA Spacious, versatile, open floor plan. Perched atop a gentle hill in the Village of Barnsta...	4 beds \| 6 baths \| 4,816 sq.ft.	$2,995,000	Airbnb cash on cash: -0.7% Traditional cash on cash: 1.51% Airbnb Rental Income: $2741 Traditional Rental Income: $8217 Airbnb ROI: -0.7% Traditional ROI: 1.51%
19 Spring Street Hyannis, MA Welcome to 19 Spring st, a charming, recently renovated single-family home offering comfor...	2 beds \| 1 baths \| 1,045 sq.ft.	$550,000	Airbnb cash on cash: 0.98% Traditional cash on cash: 2.57% Airbnb Rental Income: $1934 Traditional Rental Income: $2241 Airbnb ROI: 0.98% Traditional ROI: 2.57%
140 Seapuit Road Osterville, MA Set within Osterville's coveted Seapuit neighborhood, this magnificent home combines archi...	3 beds \| 5 baths \| 5,049 sq.ft.	$3,390,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 0.11% Airbnb Rental Income: $2013 Traditional Rental Income: $5970 Airbnb ROI: -1.32% Traditional ROI: 0.11%
36 Upland Ave Webster, MA This 3-bedroom, 2-full-bath home offers a flexible layout with a bedroom and full bathroom...	3 beds \| 2 baths \| 1,507 sq.ft.	$394,900	Airbnb cash on cash: 3.27% Traditional cash on cash: 6.38% Airbnb Rental Income: $2730 Traditional Rental Income: $3238 Airbnb ROI: 3.27% Traditional ROI: 6.38%
42 8th St #4209 Charlestown, MA 42 8th St #4209, Charlestown, MA 02129 \| Condo/Coop	1 beds \| 1 baths \| 793 sq.ft.	$639,000	Airbnb cash on cash: -1.4% Traditional cash on cash: -0.87% Airbnb Rental Income: $1867 Traditional Rental Income: $1683 Airbnb ROI: -1.4% Traditional ROI: -0.87%
38 Indian Trail Chatham, MA This exceptional coastal retreat was designed to capture sweeping views of tidal salt mars...	4 beds \| 4 baths \| 4,967 sq.ft.	$4,295,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 0.15% Airbnb Rental Income: $3457 Traditional Rental Income: $6165 Airbnb ROI: -0.72% Traditional ROI: 0.15%
12 Piedmont St #2 Boston, MA 12 Piedmont St #2, Boston, MA 02116 \| Condo/Coop	2 beds \| 2 baths \| 1,880 sq.ft.	$1,995,000	Airbnb cash on cash: -1.04% Traditional cash on cash: -0.81% Airbnb Rental Income: $3924 Traditional Rental Income: $3504 Airbnb ROI: -1.04% Traditional ROI: -0.81%
3 Avery St #305 Boston, MA 3 Avery St #305, Boston, MA 02111 \| Condo/Coop	2 beds \| 2 baths \| 1,268 sq.ft.	$849,000	Airbnb cash on cash: -1.96% Traditional cash on cash: -2.41% Airbnb Rental Income: $4137 Traditional Rental Income: $2906 Airbnb ROI: -1.96% Traditional ROI: -2.41%
580 Washington St #1410 Boston, MA 580 Washington St #1410, Boston, MA 02111 \| Condo/Coop	2 beds \| 2 baths \| 1,308 sq.ft.	$1,585,000	Airbnb cash on cash: -1.73% Traditional cash on cash: -1.72% Airbnb Rental Income: $4137 Traditional Rental Income: $3277 Airbnb ROI: -1.73% Traditional ROI: -1.72%
121 Portland St #603 Boston, MA 121 Portland St #603, Boston, MA 02114 \| Condo/Coop	1 beds \| 2 baths \| 815 sq.ft.	$749,999	Airbnb cash on cash: -1.2% Traditional cash on cash: 0.87% Airbnb Rental Income: $2293 Traditional Rental Income: $3165 Airbnb ROI: -1.2% Traditional ROI: 0.87%
374 Chestnut Hill Ave #54 BRIGHTON, MA 374 Chestnut Hill Ave #54, BRIGHTON, MA 02135 \| Condo/Coop	2 beds \| 1 baths \| 852 sq.ft.	$499,000	Airbnb cash on cash: 0.28% Traditional cash on cash: 0.65% Airbnb Rental Income: $2697 Traditional Rental Income: $2229 Airbnb ROI: 0.28% Traditional ROI: 0.65%
24 Mill St #3 Boston, MA 24 Mill St #3, Boston, MA 02122 \| Condo/Coop	3 beds \| 2 baths \| 1,317 sq.ft.	$729,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 1.82% Airbnb Rental Income: $1919 Traditional Rental Income: $3133 Airbnb ROI: -0.71% Traditional ROI: 1.82%
416 Silver Leaf Dr Becket, MA This sweet little waterfront sat by itself for 3 years. Need lots of TLC to bring it back ...	3 beds \| 2 baths \| 1,350 sq.ft.	$250,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 10.85% Airbnb Rental Income: $2222 Traditional Rental Income: $3170 Airbnb ROI: 4.46% Traditional ROI: 10.85%
28 Lakefield Road South Yarmouth, MA Welcome to this beautifully renovated 3-bedroom ranch in desirable South Yarmouth! Thought...	3 beds \| 1 baths \| 1,056 sq.ft.	$587,000	Airbnb cash on cash: 1.17% Traditional cash on cash: 2.7% Airbnb Rental Income: $2131 Traditional Rental Income: $2425 Airbnb ROI: 1.17% Traditional ROI: 2.7%
18 High Crest Rd Lenox, MA Luxury Living at Twelve Oaks Village - Privacy, Elegance & Mountain Views Discover an exce...	4 beds \| 5 baths \| 3,691 sq.ft.	$1,035,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 3.96% Airbnb Rental Income: $1831 Traditional Rental Income: $5526 Airbnb ROI: -0.39% Traditional ROI: 3.96%
13 N Glen Drive Mashpee, MA Experience the luxurious Willowbend lifestyle in this exceptionally elegant home situated ...	4 beds \| 4 baths \| 4,067 sq.ft.	$3,100,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 0.65% Airbnb Rental Income: $2848 Traditional Rental Income: $5868 Airbnb ROI: -0.63% Traditional ROI: 0.65%
724 Commercial Street Provincetown, MA Welcome to Seaview House, an extraordinary coastal retreat offering sweeping, unobstructed...	4 beds \| 4 baths \| 4,277 sq.ft.	$3,499,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 0.26% Airbnb Rental Income: $3336 Traditional Rental Income: $5417 Airbnb ROI: -0.61% Traditional ROI: 0.26%

Real Estate investment in Massachusetts

There are 8,893 properties available for sale in the state of Massachusetts. North Adams, Haverhill and Danvers are the best rental property markets in Massachusetts. The average median price of properties for sale in these cities are $481,433 and the average price per square foot is $0. Their average monthly cash on cash return is 4.67%.

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

There are 8,893 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 (9%) and Haverhill (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

199 State St #401

Boston, MA

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

$3,195,000

Airbnb cash on cash: -2.15%

Traditional cash on cash: -2.01%

Airbnb Rental Income: $3419

Traditional Rental Income: $3070

Airbnb ROI: -2.15%

Traditional ROI: -2.01%

183-185A Massachusetts Ave #803

Boston, MA

2 beds | 2 baths | 1,220 sq.ft.

$1,695,000

Airbnb cash on cash: -1.9%

Traditional cash on cash: -1.48%

Airbnb Rental Income: $2889

Traditional Rental Income: $2872

Airbnb ROI: -1.9%

Traditional ROI: -1.48%

40 Traveler St #507

Boston, MA

1 beds | 1 baths | 741 sq.ft.

$710,000

Airbnb cash on cash: -1.36%

Traditional cash on cash: 0.29%

Airbnb Rental Income: $2077

Traditional Rental Income: $2633

Airbnb ROI: -1.36%

Traditional ROI: 0.29%

10 Boylston Pl #10

Boston, MA

3 beds | 2 baths | 1,976 sq.ft.

$1,190,000

Airbnb cash on cash: -0.65%

Traditional cash on cash: 0.68%

Airbnb Rental Income: $2858

Traditional Rental Income: $3660

Airbnb ROI: -0.65%

Traditional ROI: 0.68%

1 Franklin St #5105

Boston, MA

3 beds | 3 baths | 2,196 sq.ft.

$3,550,000

Airbnb cash on cash: -2.54%

Traditional cash on cash: -2.3%

Airbnb Rental Income: $4204

Traditional Rental Income: $4111

Airbnb ROI: -2.54%

Traditional ROI: -2.3%

267 Middle St

Weymouth, MA

3 beds | 2 baths | 1,872 sq.ft.

$675,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $2879

Traditional Rental Income: $2934

Airbnb ROI: 1.58%

Traditional ROI: 2.73%

5 Moss Hill Rd

Boston, MA

5 beds | 4 baths | 3,100 sq.ft.

$2,249,999

Airbnb cash on cash: N/A

Traditional cash on cash: 0.4%

Airbnb Rental Income: $null

Traditional Rental Income: $5562

Airbnb ROI: N/A

Traditional ROI: 0.4%

4 Mount Vernon Ave #3

Charlestown, MA

2 beds | 2 baths | 1,332 sq.ft.

$1,350,000

Airbnb cash on cash: -0.79%

Traditional cash on cash: -0.44%

Airbnb Rental Income: $2899

Traditional Rental Income: $2662

Airbnb ROI: -0.79%