Real Estate Investment Properties for Sale in Winchester, MA

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

Explore a variety of short-term homes & houses in Winchester, MA. Invest wisely with VRBO & Winchester, 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 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%
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: 1.2% Traditional cash on cash: 1.01% Airbnb Rental Income: $8205 Traditional Rental Income: $6236 Airbnb ROI: 1.2% Traditional ROI: 1.01%
4 Rabbit Run Eastham , MA Panoramic views with contemporary flare and coastal charm make this distinctive Cape Cod p...	4 beds \| 5 baths \| 3,250 sq.ft.	$1,995,000	Airbnb cash on cash: 1.01% Traditional cash on cash: 1.37% Airbnb Rental Income: $5976 Traditional Rental Income: $5465 Airbnb ROI: 1.01% Traditional ROI: 1.37%
239 Chatham Road Harwich , MA 239 Chatham Road is under a mile to Red River Beach and has room for all your guests! This...	4 beds \| 3 baths \| 2,290 sq.ft.	$850,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 2.95% Airbnb Rental Income: $6174 Traditional Rental Income: $3748 Airbnb ROI: 4.47% Traditional ROI: 2.95%
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%
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: 3% Traditional cash on cash: 1.98% Airbnb Rental Income: $5178 Traditional Rental Income: $3202 Airbnb ROI: 3% Traditional ROI: 1.98%
80 Old Colony Road Hyannis , MA Back On The Market! Large, stylishly updated home with a flexible floor plan and town sewe...	3 beds \| 2 baths \| 2,512 sq.ft.	$725,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 3.22% Airbnb Rental Income: $4423 Traditional Rental Income: $3313 Airbnb ROI: 3.49% Traditional ROI: 3.22%
22 Felicity Lane Osterville , MA Welcome to 22 Felicity Lane...a beautifully built Archibald home that exudes elegance and ...	3 beds \| 3 baths \| 2,923 sq.ft.	$1,395,000	Airbnb cash on cash: 0.89% Traditional cash on cash: 1.34% Airbnb Rental Income: $4027 Traditional Rental Income: $3743 Airbnb ROI: 0.89% Traditional ROI: 1.34%
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: 7.04% Traditional cash on cash: 3.4% Airbnb Rental Income: $5901 Traditional Rental Income: $2855 Airbnb ROI: 7.04% Traditional ROI: 3.4%
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: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $2627 Airbnb ROI: N/A Traditional ROI: 3.05%
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%
13 Luka Dr #7 Grafton , MA Welcome to charming end unit at Providence Road Commons where comfort meets convenience. S...	3 beds \| 3 baths \| 2,312 sq.ft.	$679,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.4% Airbnb Rental Income: $null Traditional Rental Income: $4261 Airbnb ROI: N/A Traditional ROI: 3.4%
111 Old Main Street South Yarmouth , MA Classic old-world charm meets modern convenience at 111 Old Main St, nestled in the desira...	4 beds \| 3 baths \| 1,951 sq.ft.	$750,000	Airbnb cash on cash: 5.79% Traditional cash on cash: 4.28% Airbnb Rental Income: $6568 Traditional Rental Income: $4225 Airbnb ROI: 5.79% Traditional ROI: 4.28%
33 The Heights Mashpee , MA Incredible opportunity to own a one of a kind double lot with spectacular golf, pond and c...	4 beds \| 6 baths \| 5,830 sq.ft.	$3,500,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.05% Airbnb Rental Income: $10317 Traditional Rental Income: $8052 Airbnb ROI: 1.16% Traditional ROI: 1.05%
425 Wareham Street Middleboro , MA Single Family with 1.09 acres of land and 160' frontage on Wareham Street (RT 28). Genera...	2 beds \| 1 baths \| 1,592 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.93% Airbnb Rental Income: $null Traditional Rental Income: $2557 Airbnb ROI: N/A Traditional ROI: 3.93%
57 Pleasant St Ludlow , MA Offer deadline by 10/1/24. 8AM. Wonderful Opportunity to own this 4 Bedroom, 3 Bath Cape. ...	4 beds \| 3 baths \| 1,634 sq.ft.	$369,997	Airbnb cash on cash: N/A Traditional cash on cash: 6.24% Airbnb Rental Income: $null Traditional Rental Income: $2984 Airbnb ROI: N/A Traditional ROI: 6.24%

Real Estate investment in Winchester, MA

There are 2 properties for sale in the city of Winchester . The median list price in Winchester is $829,450 and the average price per square foot is $544. In December 2024, the average monthly cash on cash return in Winchester is 2.00%. The average monthly rental income in Winchester is $3,203.

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

There are 2 investment properties available for sale in Winchester.

In 2024, the best neighborhood to buy investment property is Winchester.

The ROI for Short-Term is higher than the Long-Term in Winchester with average rental income of $4,660.

Your search for investment property begins and ends here

Investment Property 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%

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: 1.2%

Traditional cash on cash: 1.01%

Airbnb Rental Income: $8205

Traditional Rental Income: $6236

Airbnb ROI: 1.2%

Traditional ROI: 1.01%

Eastham , MA

4 beds | 5 baths | 3,250 sq.ft.

$1,995,000

Airbnb cash on cash: 1.01%

Traditional cash on cash: 1.37%

Airbnb Rental Income: $5976

Traditional Rental Income: $5465

Airbnb ROI: 1.01%

Traditional ROI: 1.37%

Harwich , MA

4 beds | 3 baths | 2,290 sq.ft.

$850,000

Airbnb cash on cash: 4.47%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $6174

Traditional Rental Income: $3748

Airbnb ROI: 4.47%

Traditional ROI: 2.95%

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%

Truro , MA

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

$979,000

Airbnb cash on cash: 3%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $5178

Traditional Rental Income: $3202

Airbnb ROI: 3%

Traditional ROI: 1.98%

Hyannis , MA

3 beds | 2 baths | 2,512 sq.ft.

$725,000

Airbnb cash on cash: 3.49%

Traditional cash on cash: 3.22%

Airbnb Rental Income: $4423

Traditional Rental Income: $3313

Airbnb ROI: 3.49%

Traditional ROI: 3.22%

Osterville , MA

3 beds | 3 baths | 2,923 sq.ft.

$1,395,000

Airbnb cash on cash: 0.89%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $4027

Traditional Rental Income: $3743

Airbnb ROI: 0.89%

Traditional ROI: 1.34%

Natick , MA

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

$550,000

Airbnb cash on cash: 7.04%

Traditional cash on cash: 3.4%