Real Estate Investment Properties for Sale in Medway, MA

Looking for investment property in Medway, MA with high ROI ?

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
10 Longmeadow Lane Medway, MA Experience your own private retreat. Set over 300 feet off the road, this stunning, fully ...	4 beds \| 2 baths \| 3,354 sq.ft.	$835,000	Airbnb cash on cash: 0.77% Traditional cash on cash: 2.66% Airbnb Rental Income: $3218 Traditional Rental Income: $3965 Airbnb ROI: 0.77% Traditional ROI: 2.66%
2 Kingson Ln #2 Medway, MA Welcome to Woodside, one of Medwayâs premier townhouse communities. This gently lived in...	2 beds \| 3 baths \| 2,280 sq.ft.	$585,000	Airbnb cash on cash: -1.51% Traditional cash on cash: 3.52% Airbnb Rental Income: $1472 Traditional Rental Income: $3783 Airbnb ROI: -1.51% Traditional ROI: 3.52%
Investment Properties for Sale in Other Cities of Massachusetts
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%
20 Hardings Beach Road Chatham , MA In a coveted Harding's Beach location, this fully renovated Chatham home offers sweeping v...	4 beds \| 4 baths \| 2,770 sq.ft.	$1,995,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 1.38% Airbnb Rental Income: $5632 Traditional Rental Income: $4925 Airbnb ROI: 1.15% Traditional ROI: 1.38%
125 Bay Road Eastham , MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| 3 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%
73 Joshua Jethro Road Chatham , MA Located in Chatham's highly sought after Riverbay Estates community, this 3-bedroom, 2-bat...	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%
53 Chilton Lane Brewster , MA Enjoy the scenic pond view from the living room and main bedroom of this condo! In fact, i...	2 beds \| 2 baths \| 935 sq.ft.	$389,500	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.64% Airbnb Rental Income: $3072 Traditional Rental Income: $2594 Airbnb ROI: 3.03% Traditional ROI: 3.64%
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 \| 3 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: 3.16% Traditional cash on cash: 4.41% Airbnb Rental Income: $2328 Traditional Rental Income: $2075 Airbnb ROI: 3.16% Traditional ROI: 4.41%
996 Main Street Cotuit , MA Relaxed coastal living meets glorious views at this harbor front retreat in the heart of C...	4 beds \| 2 baths \| 4,303 sq.ft.	$5,500,000	Airbnb cash on cash: -0.66% Traditional cash on cash: -0.68% Airbnb Rental Income: $5178 Traditional Rental Income: $4048 Airbnb ROI: -0.66% Traditional ROI: -0.68%
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%
205 Forest Street Harwich , MA This stunning home has been thoughtfully reimagined and meticulously renovated to create a...	4 beds \| 4 baths \| 3,192 sq.ft.	$2,475,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.11% Airbnb Rental Income: $null Traditional Rental Income: $5442 Airbnb ROI: N/A Traditional ROI: 1.11%

Real Estate investment in Medway, MA

There are 2 properties for sale in the city of Medway . The median list price in Medway is $710,000 and the average price per square foot is $252. In September 2025, the average monthly cash on cash return in Medway is 3.00%. The average monthly rental income in Medway is $3,874.

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

There are 2 investment properties available for sale in Medway.

In 2025, the best neighborhood to buy investment property is Medway.

The ROI for Short-Term is higher than the Long-Term in Medway with average rental income of $2,345.

Your search for investment property begins and ends here

Investment Property for Sale in Medway, MA

10 Longmeadow Lane

Medway, MA

4 beds | 2 baths | 3,354 sq.ft.

$835,000

Airbnb cash on cash: 0.77%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $3218

Traditional Rental Income: $3965

Airbnb ROI: 0.77%

Traditional ROI: 2.66%

2 Kingson Ln #2

Medway, MA

2 beds | 3 baths | 2,280 sq.ft.

$585,000

Airbnb cash on cash: -1.51%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $1472

Traditional Rental Income: $3783

Airbnb ROI: -1.51%

Traditional ROI: 3.52%

Investment Properties for Sale in Other Cities of Massachusetts

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%

Chatham , MA

4 beds | 4 baths | 2,770 sq.ft.

$1,995,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $5632

Traditional Rental Income: $4925

Airbnb ROI: 1.15%

Traditional ROI: 1.38%

Eastham , MA

3 beds | 3 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%

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%

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%

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%

Truro , MA

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

$1,850,000

Airbnb cash on cash: 0.39%