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
94 West Street Medway, MA Tucked away on a country road just one mile from I-495, this inviting raised ranch offers ...	3 beds \| 2 baths \| 1,587 sq.ft.	$599,000	Airbnb cash on cash: 0.6% Traditional cash on cash: 3.58% Airbnb Rental Income: $2233 Traditional Rental Income: $3339 Airbnb ROI: 0.6% Traditional ROI: 3.58%
4 Shaw St Medway, MA Enjoy your morning coffee with stunning views of the Charles River from your oversized dec...	4 beds \| 1 baths \| 2,217 sq.ft.	$679,000	Airbnb cash on cash: 2.17% Traditional cash on cash: 2.4% Airbnb Rental Income: $3647 Traditional Rental Income: $3001 Airbnb ROI: 2.17% Traditional ROI: 2.4%
252 Main St Medway, MA 252 Main St, Medway, MA 02053 \| Single Family Residential	3 beds \| 1 baths \| 1,244 sq.ft.	$349,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 6.06% Airbnb Rental Income: $2233 Traditional Rental Income: $2807 Airbnb ROI: 2.6% Traditional ROI: 6.06%
28 Fisher St Medway, MA 28 Fisher St, Medway, MA 02053 \| Other	N/A beds \| N/A baths \| N/A	$300,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 4.9% Airbnb Rental Income: $1266 Traditional Rental Income: $2103 Airbnb ROI: 0.52% Traditional ROI: 4.9%
37 North Medway, MA Built in 1900, this 1,110 sq ft Colonial offers character and functional living space. The...	3 beds \| 1 baths \| 1,110 sq.ft.	$454,999	Airbnb cash on cash: 1.43% Traditional cash on cash: 3.38% Airbnb Rental Income: $2233 Traditional Rental Income: $2500 Airbnb ROI: 1.43% Traditional ROI: 3.38%
34 Broken Tree Rd Medway, MA An original owner, custom built distinguished residence offers an exceptional opportunity ...	4 beds \| 4 baths \| 4,788 sq.ft.	$1,175,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 2.65% Airbnb Rental Income: $3647 Traditional Rental Income: $5490 Airbnb ROI: 0.23% Traditional ROI: 2.65%
3 Stable Way Medway, MA Do not miss your opportunity to own this beautiful custom Colonial in one of Medway's most...	4 beds \| 3 baths \| 3,166 sq.ft.	$1,125,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.95% Airbnb Rental Income: $3647 Traditional Rental Income: $4355 Airbnb ROI: 0.51% Traditional ROI: 1.95%
21 Autumn Road Medway, MA Welcome home to this beautifully updated 3-bedroom, 2-bath gem, ideally located in a fanta...	3 beds \| 2 baths \| 1,586 sq.ft.	$675,000	Airbnb cash on cash: 0.4% Traditional cash on cash: 3.43% Airbnb Rental Income: $2233 Traditional Rental Income: $3579 Airbnb ROI: 0.4% Traditional ROI: 3.43%
35 Milford St Medway, MA Welcome home to this beautifully crafted newer construction Colonial in a fantastic Medway...	3 beds \| 2 baths \| 3,024 sq.ft.	$997,000	Airbnb cash on cash: -0.56% Traditional cash on cash: 2.12% Airbnb Rental Income: $2233 Traditional Rental Income: $4157 Airbnb ROI: -0.56% Traditional ROI: 2.12%
7 Hemlock Dr Medway, MA 7 Hemlock Dr, Medway, MA 02053 \| Single Family Residential	3 beds \| 1 baths \| 1,416 sq.ft.	$529,900	Airbnb cash on cash: 0.97% Traditional cash on cash: 2.68% Airbnb Rental Income: $2233 Traditional Rental Income: $2522 Airbnb ROI: 0.97% Traditional ROI: 2.68%
92 Lovering St Medway, MA 92 Lovering St, Medway, MA 02053 \| Single Family Residential	4 beds \| 2 baths \| 2,467 sq.ft.	$700,000	Airbnb cash on cash: 2% Traditional cash on cash: 2.09% Airbnb Rental Income: $3647 Traditional Rental Income: $2910 Airbnb ROI: 2% Traditional ROI: 2.09%
15 Little Tree Rd Medway, MA 15 Little Tree Rd, Medway, MA 02053 \| Single Family Residential	4 beds \| 3 baths \| 3,204 sq.ft.	$975,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 0.88% Airbnb Rental Income: $3647 Traditional Rental Income: $2910 Airbnb ROI: 0.82% Traditional ROI: 0.88%
284 Village St Medway, MA 284 Village St, Medway, MA 02053 \| Single Family Residential	4 beds \| 2 baths \| 1,804 sq.ft.	$629,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 2.58% Airbnb Rental Income: $3647 Traditional Rental Income: $2910 Airbnb ROI: 2.48% Traditional ROI: 2.58%
17 Farm St Medway, MA 17 Farm St, Medway, MA 02053 \| Single Family Residential	3 beds \| 1 baths \| 1,858 sq.ft.	$725,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.77% Airbnb Rental Income: $2233 Traditional Rental Income: $2793 Airbnb ROI: 0.11% Traditional ROI: 1.77%
10 Charles View Ln Medway, MA 10 Charles View Ln, Medway, MA 02053 \| Single Family Residential	4 beds \| 4 baths \| 3,237 sq.ft.	$979,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 0.35% Airbnb Rental Income: $3647 Traditional Rental Income: $2910 Airbnb ROI: 0.28% Traditional ROI: 0.35%
2 Harmony Way #2 Medway, MA 2 Harmony Way #2, Medway, MA 02053 \| Townhouse	3 beds \| 2 baths \| 2,696 sq.ft.	$749,900	Airbnb cash on cash: -1% Traditional cash on cash: 1.99% Airbnb Rental Income: $2233 Traditional Rental Income: $3759 Airbnb ROI: -1% Traditional ROI: 1.99%
58 Adams St Medway, MA 58 Adams St, Medway, MA 02053 \| Single Family Residential	3 beds \| 2 baths \| 1,600 sq.ft.	$725,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.37% Airbnb Rental Income: $2233 Traditional Rental Income: $2522 Airbnb ROI: 0.11% Traditional ROI: 1.37%
10 Charles View Ln #10 Medway, MA 10 Charles View Ln #10, Medway, MA 02053 \| Condo/Coop	4 beds \| 4 baths \| 3,237 sq.ft.	$979,900	Airbnb cash on cash: 0.28% Traditional cash on cash: 0.35% Airbnb Rental Income: $3647 Traditional Rental Income: $2910 Airbnb ROI: 0.28% Traditional ROI: 0.35%
328 Village St #328 Medway, MA 328 Village St #328, Medway, MA 02053 \| Townhouse	3 beds \| 2 baths \| 2,408 sq.ft.	$749,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 1.26% Airbnb Rental Income: $2233 Traditional Rental Income: $2522 Airbnb ROI: 0.04% Traditional ROI: 1.26%
20 Broad St #3 Medway, MA 20 Broad St #3, Medway, MA 02053 \| Townhouse	3 beds \| 3 baths \| 1,576 sq.ft.	$599,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.49% Airbnb Rental Income: $2233 Traditional Rental Income: $2522 Airbnb ROI: -0.03% Traditional ROI: 1.49%
20 Broad St #5 Medway, MA 20 Broad St #5, Medway, MA 02053 \| Townhouse	3 beds \| 2 baths \| 1,700 sq.ft.	$599,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.49% Airbnb Rental Income: $2233 Traditional Rental Income: $2522 Airbnb ROI: -0.03% Traditional ROI: 1.49%
21 Summer St Medway, MA 21 Summer St, Medway, MA 02053 \| Other	N/A beds \| N/A baths \| N/A	$200,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 8.38% Airbnb Rental Income: $1266 Traditional Rental Income: $2103 Airbnb ROI: 1.86% Traditional ROI: 8.38%

Real Estate investment in Medway, MA

There are 26 properties for sale in the city of Medway . The median list price in Medway is $689,587 and the average price per square foot is $281. In September 2026, the average monthly cash on cash return in Medway is 2.00%. The average monthly rental income in Medway is $2,910.

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

There are 26 investment properties available for sale in Medway.

In 2026, the best neighborhood to buy investment property is Medway.

The ROI for Long-Term is higher than the Short-Term in Medway with average rental income of $2,910.

Your search for investment property begins and ends here

Investment Property for Sale in Medway, MA

94 West Street

Medway, MA

3 beds | 2 baths | 1,587 sq.ft.

$599,000

Airbnb cash on cash: 0.6%

Traditional cash on cash: 3.58%

Airbnb Rental Income: $2233

Traditional Rental Income: $3339

Airbnb ROI: 0.6%

Traditional ROI: 3.58%

4 Shaw St

Medway, MA

4 beds | 1 baths | 2,217 sq.ft.

$679,000

Airbnb cash on cash: 2.17%

Traditional cash on cash: 2.4%

Airbnb Rental Income: $3647

Traditional Rental Income: $3001

Airbnb ROI: 2.17%

Traditional ROI: 2.4%

252 Main St

Medway, MA

3 beds | 1 baths | 1,244 sq.ft.

$349,000

Airbnb cash on cash: 2.6%

Traditional cash on cash: 6.06%

Airbnb Rental Income: $2233

Traditional Rental Income: $2807

Airbnb ROI: 2.6%

Traditional ROI: 6.06%

28 Fisher St

Medway, MA

N/A beds | N/A baths | N/A

$300,000

Airbnb cash on cash: 0.52%

Traditional cash on cash: 4.9%

Airbnb Rental Income: $1266

Traditional Rental Income: $2103

Airbnb ROI: 0.52%

Traditional ROI: 4.9%

37 North

Medway, MA

3 beds | 1 baths | 1,110 sq.ft.

$454,999

Airbnb cash on cash: 1.43%

Traditional cash on cash: 3.38%

Airbnb Rental Income: $2233

Traditional Rental Income: $2500

Airbnb ROI: 1.43%

Traditional ROI: 3.38%

34 Broken Tree Rd

Medway, MA

4 beds | 4 baths | 4,788 sq.ft.

$1,175,000

Airbnb cash on cash: 0.23%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $3647

Traditional Rental Income: $5490

Airbnb ROI: 0.23%

Traditional ROI: 2.65%

3 Stable Way

Medway, MA

4 beds | 3 baths | 3,166 sq.ft.

$1,125,000

Airbnb cash on cash: 0.51%

Traditional cash on cash: 1.95%

Airbnb Rental Income: $3647

Traditional Rental Income: $4355

Airbnb ROI: 0.51%

Traditional ROI: 1.95%

21 Autumn Road

Medway, MA

3 beds | 2 baths | 1,586 sq.ft.

$675,000

Airbnb cash on cash: 0.4%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $2233

Traditional Rental Income: $3579

Airbnb ROI: 0.4%