Real Estate Investment Properties for Sale in Weston, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
135 Orchard Ave Weston, MA Welcome to 135 Orchard Avenue, a rare and exceptional property in Weston. Set on over 2.5 ...	5 beds \| 5 baths \| 4,340 sq.ft.	$5,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.36% Airbnb Rental Income: $null Traditional Rental Income: $6588 Airbnb ROI: N/A Traditional ROI: 0.36%
60 Possum Rd Weston, MA Location, Location,Location! Tucked away on a private roadâone of nine encircling the We...	4 beds \| 4 baths \| 3,953 sq.ft.	$2,500,000	Airbnb cash on cash: -0.8% Traditional cash on cash: 0.23% Airbnb Rental Income: $4316 Traditional Rental Income: $5786 Airbnb ROI: -0.8% Traditional ROI: 0.23%
60 Rolling Ln Weston, MA Rare opportunity to own a stunning contemporary home with a spectacular pool, nestled in o...	5 beds \| 4 baths \| 4,300 sq.ft.	$2,595,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.37% Airbnb Rental Income: $null Traditional Rental Income: $5816 Airbnb ROI: N/A Traditional ROI: 1.37%
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: N/A Traditional cash on cash: 0.27% Airbnb Rental Income: $null Traditional Rental Income: $4593 Airbnb ROI: N/A Traditional ROI: 0.27%
121 Portland St #505 Boston , MA 121 Portland St #505, Boston, MA 02114 \| Condo/Coop	1 beds \| 1 baths \| 481 sq.ft.	$575,000	Airbnb cash on cash: 3.25% Traditional cash on cash: 0.77% Airbnb Rental Income: $4476 Traditional Rental Income: $2212 Airbnb ROI: 3.25% Traditional ROI: 0.77%
112 Roslindale Ave #2 Boston , MA 112 Roslindale Ave #2, Boston, MA 02131 \| Condo/Coop	3 beds \| 2 baths \| 1,183 sq.ft.	$599,900	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.76% Airbnb Rental Income: $3257 Traditional Rental Income: $3187 Airbnb ROI: 1.58% Traditional ROI: 2.76%
32 Lime St Boston , MA	4 beds \| 5 baths \| 5,194 sq.ft.	$9,450,000	Airbnb cash on cash: -1.66% Traditional cash on cash: -1.48% Airbnb Rental Income: $6280 Traditional Rental Income: $6608 Airbnb ROI: -1.66% Traditional ROI: -1.48%
78 Hutchings St #1 Boston , MA 78 Hutchings St #1, Boston, MA 02121 \| Condo/Coop	3 beds \| 2 baths \| 1,837 sq.ft.	$599,000	Airbnb cash on cash: 1.7% Traditional cash on cash: 3.2% Airbnb Rental Income: $3221 Traditional Rental Income: $3338 Airbnb ROI: 1.7% Traditional ROI: 3.2%
280 Beacon St #1 Boston , MA 280 Beacon St #1, Boston, MA 02116 \| Condo/Coop	1 beds \| 1 baths \| 685 sq.ft.	$699,000	Airbnb cash on cash: -1.25% Traditional cash on cash: -0.33% Airbnb Rental Income: $1893 Traditional Rental Income: $1986 Airbnb ROI: -1.25% Traditional ROI: -0.33%
2 Larose Pl #13 Boston , MA 2 Larose Pl #13, Boston, MA 02135 \| Condo/Coop	2 beds \| 1 baths \| 735 sq.ft.	$529,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.91% Airbnb Rental Income: $1502 Traditional Rental Income: $2121 Airbnb ROI: -1.23% Traditional ROI: 0.91%
75 Burbank St #501 Boston , MA 75 Burbank St #501, Boston, MA 02115 \| Condo/Coop	1 beds \| 1 baths \| 425 sq.ft.	$496,000	Airbnb cash on cash: 0.29% Traditional cash on cash: 0.75% Airbnb Rental Income: $2175 Traditional Rental Income: $1833 Airbnb ROI: 0.29% Traditional ROI: 0.75%
28-32 Atlantic Ave #424 Boston , MA 28-32 Atlantic Ave #424, Boston, MA 02110 \| Condo/Coop	2 beds \| 1 baths \| 1,023 sq.ft.	$1,370,000	Airbnb cash on cash: -1.8% Traditional cash on cash: -1.87% Airbnb Rental Income: $3073 Traditional Rental Income: $2284 Airbnb ROI: -1.8% Traditional ROI: -1.87%
125 Bay Road Eastham , MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| 2 baths \| 1,662 sq.ft.	$2,195,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 0.17% Airbnb Rental Income: $2826 Traditional Rental Income: $3577 Airbnb ROI: -0.52% 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.	$1,299,000	Airbnb cash on cash: -0.4% Traditional cash on cash: 0.78% Airbnb Rental Income: $2850 Traditional Rental Income: $3609 Airbnb ROI: -0.4% Traditional ROI: 0.78%
15 Shannon Road Harwich , MA Step into this beautifully renovated 3 bed 2 bath home featuring a brand-new kitchen and b...	3 beds \| 2 baths \| 1,124 sq.ft.	$629,900	Airbnb cash on cash: 2.47% Traditional cash on cash: 3.49% Airbnb Rental Income: $3107 Traditional Rental Income: $3001 Airbnb ROI: 2.47% Traditional ROI: 3.49%
73 Joshua Jethro Road Chatham , MA PERFECT HOUSE FOR A POOL! Located in Chatham's highly sought after Riverbay Estates commun...	3 beds \| 2 baths \| 2,307 sq.ft.	$1,520,000	Airbnb cash on cash: -0.23% Traditional cash on cash: 1.11% Airbnb Rental Income: $2063 Traditional Rental Income: $3418 Airbnb ROI: -0.23% Traditional ROI: 1.11%
1 Franklin St Ph 4E Boston , MA 1 Franklin St Ph 4E, Boston, MA 02110 \| Condo/Coop	3 beds \| 4 baths \| 3,435 sq.ft.	$7,495,000	Airbnb cash on cash: -2.98% Traditional cash on cash: -2.56% Airbnb Rental Income: $3038 Traditional Rental Income: $5277 Airbnb ROI: -2.98% Traditional ROI: -2.56%
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.	$1,799,000	Airbnb cash on cash: -0.93% Traditional cash on cash: 0.87% Airbnb Rental Income: $1633 Traditional Rental Income: $4180 Airbnb ROI: -0.93% Traditional ROI: 0.87%

Real Estate investment in Weston, MA

There are 3 properties for sale in the city of Weston . The median list price in Weston is $2,595,000 and the average price per square foot is $618. In December 2025, the average monthly cash on cash return in Weston is N/A%. The average monthly rental income in Weston is $5,816.

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

There are 3 investment properties available for sale in Weston.

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

The ROI for Long-Term is higher than the Short-Term in Weston with average rental income of $5,816.

Your search for investment property begins and ends here

Investment Property for Sale in Weston, MA

135 Orchard Ave

Weston, MA

5 beds | 5 baths | 4,340 sq.ft.

$5,150,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.36%

Airbnb Rental Income: $null

Traditional Rental Income: $6588

Airbnb ROI: N/A

Traditional ROI: 0.36%

60 Possum Rd

Weston, MA

4 beds | 4 baths | 3,953 sq.ft.

$2,500,000

Airbnb cash on cash: -0.8%

Traditional cash on cash: 0.23%

Airbnb Rental Income: $4316

Traditional Rental Income: $5786

Airbnb ROI: -0.8%

Traditional ROI: 0.23%

60 Rolling Ln

Weston, MA

5 beds | 4 baths | 4,300 sq.ft.

$2,595,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.37%

Airbnb Rental Income: $null

Traditional Rental Income: $5816

Airbnb ROI: N/A

Traditional ROI: 1.37%

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: N/A

Traditional cash on cash: 0.27%

Airbnb Rental Income: $null

Traditional Rental Income: $4593

Airbnb ROI: N/A

Traditional ROI: 0.27%

Boston , MA

1 beds | 1 baths | 481 sq.ft.

$575,000

Airbnb cash on cash: 3.25%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $4476

Traditional Rental Income: $2212

Airbnb ROI: 3.25%

Traditional ROI: 0.77%

Boston , MA

3 beds | 2 baths | 1,183 sq.ft.

$599,900

Airbnb cash on cash: 1.58%

Traditional cash on cash: 2.76%

Airbnb Rental Income: $3257

Traditional Rental Income: $3187

Airbnb ROI: 1.58%

Traditional ROI: 2.76%

Boston , MA

4 beds | 5 baths | 5,194 sq.ft.

$9,450,000

Airbnb cash on cash: -1.66%

Traditional cash on cash: -1.48%

Airbnb Rental Income: $6280

Traditional Rental Income: $6608

Airbnb ROI: -1.66%

Traditional ROI: -1.48%

Boston , MA

3 beds | 2 baths | 1,837 sq.ft.

$599,000

Airbnb cash on cash: 1.7%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $3221

Traditional Rental Income: $3338

Airbnb ROI: 1.7%

Traditional ROI: 3.2%

Boston , MA

1 beds | 1 baths | 685 sq.ft.

$699,000