Airbnb Properties for Sale in Winchester, MA

Looking for a vacation rental investment in Winchester, MA with high ROI ?

Explore a range of newly added short-term rental homes in Winchester, MA. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Winchester, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
666 Main Street #LV2 Winchester, MA Welcome to 666 Main Street, Unit LV2, Winchester. This beautiful well maintained 2 bedroom...	2 beds \| 2 baths \| 1,160 sq.ft.	$679,000	Airbnb cash on cash: 2.59% Traditional cash on cash: 1.51% Airbnb Rental Income: $4660 Traditional Rental Income: $3007 Airbnb ROI: 2.59% Traditional ROI: 1.51%
Airbnb 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: 1.2% Traditional cash on cash: 0.27% Airbnb Rental Income: $8205 Traditional Rental Income: $4593 Airbnb ROI: 1.2% Traditional ROI: 0.27%
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: 5.08% Traditional cash on cash: 2.59% Airbnb Rental Income: $6174 Traditional Rental Income: $3102 Airbnb ROI: 5.08% Traditional ROI: 2.59%
11 Elinor Lane West Harwich , MA Charming Coastal Retreat with Rental Property Near Pleasant Street Beach. This spacious 4-...	4 beds \| 3 baths \| 2,066 sq.ft.	$1,350,000	Airbnb cash on cash: 2.27% Traditional cash on cash: 1.68% Airbnb Rental Income: $5855 Traditional Rental Income: $3943 Airbnb ROI: 2.27% Traditional ROI: 1.68%
5 Glacier Drive Truro , MA Charming Cape on the Market! Welcome to this beautifully renovated 3-bedroom, 2-1/2 b...	3 beds \| 3 baths \| 1,734 sq.ft.	$979,000	Airbnb cash on cash: 9.7% Traditional cash on cash: 1.98% Airbnb Rental Income: $12501 Traditional Rental Income: $3202 Airbnb ROI: 9.7% Traditional ROI: 1.98%
210 E Central Street #210 Natick , MA PRICE IMPROVEMENT! Donât miss this great opportunity to own Half Duplex in Natick. MOVE ...	3 beds \| 2 baths \| 1,166 sq.ft.	$550,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 3.44% Airbnb Rental Income: $5577 Traditional Rental Income: $2877 Airbnb ROI: 6.52% Traditional ROI: 3.44%
24 Adams Rd Grafton , MA Welcome home to 24 Adams Rd. This bright and well maintained multilevel home sits on .88 a...	3 beds \| 1 baths \| 1,280 sq.ft.	$518,000	Airbnb cash on cash: 9.48% Traditional cash on cash: 3.45% Airbnb Rental Income: $7116 Traditional Rental Income: $2819 Airbnb ROI: 9.48% Traditional ROI: 3.45%
34 Horizon Drive Chatham , MA Deeded Access to stunning Lover's Lake, only a 3-minute walk! Welcome to 34 Horizon Drive,...	3 beds \| 3 baths \| 2,400 sq.ft.	$999,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 2.34% Airbnb Rental Income: $6827 Traditional Rental Income: $3558 Airbnb ROI: 4.43% Traditional ROI: 2.34%
8 Daffodil Ct #8 Grafton , MA Welcome to desirable Hilltop Farms built by industry leader Pulte Homes! This beautiful to...	3 beds \| 3 baths \| 2,170 sq.ft.	$509,900	Airbnb cash on cash: 8.74% Traditional cash on cash: 3.96% Airbnb Rental Income: $7116 Traditional Rental Income: $3462 Airbnb ROI: 8.74% Traditional ROI: 3.96%
22 Angus Avenue South Yarmouth , MA Adorable home situated on a quiet dead end road with a fenced in yard yet central to every...	2 beds \| 1 baths \| 816 sq.ft.	$439,000	Airbnb cash on cash: 5.94% Traditional cash on cash: 3.76% Airbnb Rental Income: $4057 Traditional Rental Income: $2296 Airbnb ROI: 5.94% Traditional ROI: 3.76%
103 Park Street Wrentham , MA Welcome to this beautiful expanded Ranch! You'll fall in love with all the updates, especi...	3 beds \| 2 baths \| 2,556 sq.ft.	$659,900	Airbnb cash on cash: 4.63% Traditional cash on cash: 3.72% Airbnb Rental Income: $5133 Traditional Rental Income: $3523 Airbnb ROI: 4.63% Traditional ROI: 3.72%
33 Almira Road South Yarmouth , MA A new home is the beginning of a life filled with fresh experiences and opportunities. 33 ...	2 beds \| 2 baths \| 1,563 sq.ft.	$659,000	Airbnb cash on cash: 3.41% Traditional cash on cash: 3.16% Airbnb Rental Income: $4057 Traditional Rental Income: $3036 Airbnb ROI: 3.41% Traditional ROI: 3.16%
51 Chilton Lane Brewster , MA Welcome to your new peaceful retreat on Chilton Lane! This 2-bedroom, 2-bathroom condo is ...	2 beds \| 2 baths \| 935 sq.ft.	$384,900	Airbnb cash on cash: 4.92% Traditional cash on cash: 3.23% Airbnb Rental Income: $3802 Traditional Rental Income: $2371 Airbnb ROI: 4.92% Traditional ROI: 3.23%
12 Bettys Lane Harwich , MA This charming and updated home offers the ease of one-floor living with a perfect blend of...	3 beds \| 2 baths \| 1,192 sq.ft.	$759,000	Airbnb cash on cash: 3.33% Traditional cash on cash: 2.66% Airbnb Rental Income: $4543 Traditional Rental Income: $3125 Airbnb ROI: 3.33% Traditional ROI: 2.66%
168 Shore Road #8 Truro , MA This large bright, open ,one plus ,two full bath '' year round'', end unit rarely comes on...	1 beds \| 2 baths \| 517 sq.ft.	$695,000	Airbnb cash on cash: 2.41% Traditional cash on cash: 1.04% Airbnb Rental Income: $3673 Traditional Rental Income: $1984 Airbnb ROI: 2.41% Traditional ROI: 1.04%
78 Robertson St Quincy , MA Welcome, Welcome!! Come to see this gorgeous lovely single family home located just two mi...	3 beds \| 2 baths \| 1,348 sq.ft.	$589,900	Airbnb cash on cash: 5.2% Traditional cash on cash: 3.36% Airbnb Rental Income: $5048 Traditional Rental Income: $3002 Airbnb ROI: 5.2% Traditional ROI: 3.36%

Vacation Rentals in Winchester

There are 1 vacation rental properties available for sale in the city of Winchester . The median list price of Airbnb properties available for sale in Winchester is $829,450 and the average price per square foot is $544. The cash on cash return on vacation rentals in Winchester is 3.00%. The average monthly short term rental income in Winchester is $4,660.

Winchester, MA Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 1 Airbnb properties available for sale in Winchester.

In 2024, the best neighborhood to buy short term rental property is Winchester.

In December 2024, the average Airbnb occupancy rate in Winchester is 50%.

Airbnb data on vacation rentals in Winchester, MA is available at Mashvisor. You can access data such as listings, real-time pricing trends, Winchester, MA market insights, guest information and booking details, seasonality trends and historical Winchester, MA Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Winchester, MA

666 Main Street #LV2

Winchester, MA

2 beds | 2 baths | 1,160 sq.ft.

$679,000

Airbnb cash on cash: 2.59%

Traditional cash on cash: 1.51%

Airbnb Rental Income: $4660

Traditional Rental Income: $3007

Airbnb ROI: 2.59%

Traditional ROI: 1.51%

Airbnb 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: 1.2%

Traditional cash on cash: 0.27%

Airbnb Rental Income: $8205

Traditional Rental Income: $4593

Airbnb ROI: 1.2%

Traditional ROI: 0.27%

Harwich , MA

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

$799,000

Airbnb cash on cash: 5.08%

Traditional cash on cash: 2.59%

Airbnb Rental Income: $6174

Traditional Rental Income: $3102

Airbnb ROI: 5.08%

Traditional ROI: 2.59%

West Harwich , MA

4 beds | 3 baths | 2,066 sq.ft.

$1,350,000

Airbnb cash on cash: 2.27%

Traditional cash on cash: 1.68%

Airbnb Rental Income: $5855

Traditional Rental Income: $3943

Airbnb ROI: 2.27%

Traditional ROI: 1.68%

Truro , MA

3 beds | 3 baths | 1,734 sq.ft.

$979,000

Airbnb cash on cash: 9.7%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $12501

Traditional Rental Income: $3202

Airbnb ROI: 9.7%

Traditional ROI: 1.98%

Natick , MA

3 beds | 2 baths | 1,166 sq.ft.

$550,000

Airbnb cash on cash: 6.52%

Traditional cash on cash: 3.44%

Airbnb Rental Income: $5577

Traditional Rental Income: $2877

Airbnb ROI: 6.52%

Traditional ROI: 3.44%

Grafton , MA

3 beds | 1 baths | 1,280 sq.ft.

$518,000

Airbnb cash on cash: 9.48%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $7116

Traditional Rental Income: $2819

Airbnb ROI: 9.48%

Traditional ROI: 3.45%

Chatham , MA

3 beds | 3 baths | 2,400 sq.ft.

$999,000

Airbnb cash on cash: 4.43%

Traditional cash on cash: 2.34%

Airbnb Rental Income: $6827

Traditional Rental Income: $3558

Airbnb ROI: 4.43%

Traditional ROI: 2.34%

Grafton , MA

3 beds | 3 baths | 2,170 sq.ft.

$509,900

Airbnb cash on cash: 8.74%

Traditional cash on cash: 3.96%