Real Estate Investment Properties for Sale in Upton, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
13 Knowlton Cir #13 Upton, MA 13 Knowlton Circle offers comfortable and low-maintenance townhouse living in a desirable ...	3 beds \| 4 baths \| 1,731 sq.ft.	$532,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.38% Airbnb Rental Income: $null Traditional Rental Income: $3900 Airbnb ROI: N/A Traditional ROI: 5.38%
87 Shannon Way #86 Upton, MA Enjoy low-maintenance living at Upton Ridge, a desirable 55+ community just a short stroll...	2 beds \| 3 baths \| 1,930 sq.ft.	$729,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.66% Airbnb Rental Income: $null Traditional Rental Income: $3978 Airbnb ROI: N/A Traditional ROI: 3.66%
46 Rockwood Lane #46 Upton, MA Absolutely Stunning Home in Rockwood Meadows Neighborhood - Detached 55+ Condo Loaded With...	2 beds \| 4 baths \| 3,925 sq.ft.	$1,075,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $5204 Airbnb ROI: N/A Traditional ROI: 3.05%
24 Fowler Street Upton, MA COMFORT MEETS COUNTRY SERENITY! Tucked away on a peaceful country road with 2+ acres of wo...	3 beds \| 3 baths \| 2,627 sq.ft.	$749,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.8% Airbnb Rental Income: $null Traditional Rental Income: $4255 Airbnb ROI: N/A Traditional ROI: 3.8%
Investment Properties for Sale in Other Cities of Massachusetts
12 Hereford St #2 Boston , MA 12 Hereford St #2, Boston, MA 02115 \| Condo/Coop	1 beds \| 2 baths \| 1,195 sq.ft.	$1,440,000	Airbnb cash on cash: -2% Traditional cash on cash: -0.6% Airbnb Rental Income: $1251 Traditional Rental Income: $2738 Airbnb ROI: -2% Traditional ROI: -0.6%
40 Traveler St #507 Boston , MA Welcome to Siena Condominium, where modern city living meets elevated comfort. This south-...	1 beds \| 1 baths \| 741 sq.ft.	$760,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 0.21% Airbnb Rental Income: $2039 Traditional Rental Income: $2633 Airbnb ROI: -1.38% Traditional ROI: 0.21%
699 Hyde Park Ave #6 Boston , MA Sunny and well-maintained 2-bedroom condo in a convenient Roslindale location near Forest ...	2 beds \| 1 baths \| 746 sq.ft.	$414,000	Airbnb cash on cash: 0.82% Traditional cash on cash: 2.16% Airbnb Rental Income: $2148 Traditional Rental Income: $2121 Airbnb ROI: 0.82% Traditional ROI: 2.16%
12 Stoneholm St #418 Boston , MA	1 beds \| 1 baths \| 400 sq.ft.	$469,000	Airbnb cash on cash: 0.05% Traditional cash on cash: 0.7% Airbnb Rental Income: $2157 Traditional Rental Income: $1892 Airbnb ROI: 0.05% Traditional ROI: 0.7%
180 Commonwealth Ave #7 Boston , MA 180 Commonwealth Ave #7, Boston, MA 02116 \| Condo/Coop	3 beds \| 2 baths \| 1,070 sq.ft.	$1,400,000	Airbnb cash on cash: 0.15% Traditional cash on cash: -0.65% Airbnb Rental Income: $5016 Traditional Rental Income: $2954 Airbnb ROI: 0.15% Traditional ROI: -0.65%
35 Fay St #202 Boston , MA 35 Fay St #202, Boston, MA 02118 \| Condo/Coop	1 beds \| 1 baths \| 1,004 sq.ft.	$775,000	Airbnb cash on cash: -1.38% Traditional cash on cash: -0.5% Airbnb Rental Income: $2142 Traditional Rental Income: $2228 Airbnb ROI: -1.38% Traditional ROI: -0.5%
32 Lime St Boston , MA	4 beds \| 5 baths \| 5,194 sq.ft.	$8,450,000	Airbnb cash on cash: -2.06% Traditional cash on cash: -1.39% Airbnb Rental Income: $1903 Traditional Rental Income: $6608 Airbnb ROI: -2.06% Traditional ROI: -1.39%
319 Forest Hills St #2 Boston , MA 319 Forest Hills St #2, Boston, MA 02130 \| Condo/Coop	2 beds \| 2 baths \| 1,070 sq.ft.	$769,500	Airbnb cash on cash: 0.52% Traditional cash on cash: 1.89% Airbnb Rental Income: $3068 Traditional Rental Income: $3352 Airbnb ROI: 0.52% Traditional ROI: 1.89%
198 Byron St Boston , MA 198 Byron St, Boston, MA 02128 \| Single Family Residential	3 beds \| 1 baths \| 2,385 sq.ft.	$1,150,000	Airbnb cash on cash: -0.11% Traditional cash on cash: 0.22% Airbnb Rental Income: $3055 Traditional Rental Income: $2708 Airbnb ROI: -0.11% Traditional ROI: 0.22%
580 Washington St #1414 Boston , MA	1 beds \| 1 baths \| 799 sq.ft.	$895,000	Airbnb cash on cash: -1.68% Traditional cash on cash: -0.94% Airbnb Rental Income: $2171 Traditional Rental Income: $2242 Airbnb ROI: -1.68% Traditional ROI: -0.94%
13 Wellington St Boston , MA Beautiful townhouse on quiet, tree-lined street minutes from T, Prudential Center, Symphon...	4 beds \| 3 baths \| 3,110 sq.ft.	$3,590,000	Airbnb cash on cash: -1.01% Traditional cash on cash: -0.38% Airbnb Rental Income: $2904 Traditional Rental Income: $4312 Airbnb ROI: -1.01% Traditional ROI: -0.38%
15 Spinney Street #1 Boston , MA Beautiful two-bedroom condo in a thoughtfully restored brick two-family home in desirable ...	2 beds \| 2 baths \| 1,059 sq.ft.	$665,000	Airbnb cash on cash: 2.22% Traditional cash on cash: 2.48% Airbnb Rental Income: $3056 Traditional Rental Income: $2522 Airbnb ROI: 2.22% Traditional ROI: 2.48%
1 Franklin St #1205 Boston , MA Move in and see why Millennium Tower Boston is the evolution of luxury residential living!...	2 beds \| 2 baths \| 1,161 sq.ft.	$1,675,000	Airbnb cash on cash: -1.83% Traditional cash on cash: 0.19% Airbnb Rental Income: $3119 Traditional Rental Income: $5552 Airbnb ROI: -1.83% Traditional ROI: 0.19%
588 S Orleans Road Orleans , MA Lush lawns and hydrangeas flanking a winding seashell driveway create a storybook entrance...	3 beds \| 3 baths \| 2,841 sq.ft.	$1,595,000	Airbnb cash on cash: -0.72% Traditional cash on cash: 1.04% Airbnb Rental Income: $1838 Traditional Rental Income: $3944 Airbnb ROI: -0.72% Traditional ROI: 1.04%
43 S Highland Road Truro , MA Unique, architecturally designed contemporary cape home set on 1.54 private wooded acres a...	2 beds \| 1 baths \| 1,317 sq.ft.	$925,000	Airbnb cash on cash: -0.43% Traditional cash on cash: 1.13% Airbnb Rental Income: $1539 Traditional Rental Income: $2441 Airbnb ROI: -0.43% Traditional ROI: 1.13%

Real Estate investment in Upton, MA

There are 4 properties for sale in the city of Upton . The median list price in Upton is $647,166 and the average price per square foot is $253. In June 2026, the average monthly cash on cash return in Upton is 4.00%. The average monthly rental income in Upton is $4,117.

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

There are 4 investment properties available for sale in Upton.

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

The ROI for Short-Term is higher than the Long-Term in Upton with average rental income of $N/A.

Your search for investment property begins and ends here

Investment Property for Sale in Upton, MA

13 Knowlton Cir #13

Upton, MA

3 beds | 4 baths | 1,731 sq.ft.

$532,000

Airbnb cash on cash: N/A

Traditional cash on cash: 5.38%

Airbnb Rental Income: $null

Traditional Rental Income: $3900

Airbnb ROI: N/A

Traditional ROI: 5.38%

87 Shannon Way #86

Upton, MA

2 beds | 3 baths | 1,930 sq.ft.

$729,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.66%

Airbnb Rental Income: $null

Traditional Rental Income: $3978

Airbnb ROI: N/A

Traditional ROI: 3.66%

46 Rockwood Lane #46

Upton, MA

2 beds | 4 baths | 3,925 sq.ft.

$1,075,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.05%

Airbnb Rental Income: $null

Traditional Rental Income: $5204

Airbnb ROI: N/A

Traditional ROI: 3.05%

24 Fowler Street

Upton, MA

3 beds | 3 baths | 2,627 sq.ft.

$749,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.8%

Airbnb Rental Income: $null

Traditional Rental Income: $4255

Airbnb ROI: N/A

Traditional ROI: 3.8%

Investment Properties for Sale in Other Cities of Massachusetts

Boston , MA

1 beds | 2 baths | 1,195 sq.ft.

$1,440,000

Airbnb cash on cash: -2%

Traditional cash on cash: -0.6%

Airbnb Rental Income: $1251

Traditional Rental Income: $2738

Airbnb ROI: -2%

Traditional ROI: -0.6%

Boston , MA

1 beds | 1 baths | 741 sq.ft.

$760,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: 0.21%

Airbnb Rental Income: $2039

Traditional Rental Income: $2633

Airbnb ROI: -1.38%

Traditional ROI: 0.21%

Boston , MA

2 beds | 1 baths | 746 sq.ft.

$414,000

Airbnb cash on cash: 0.82%

Traditional cash on cash: 2.16%

Airbnb Rental Income: $2148

Traditional Rental Income: $2121

Airbnb ROI: 0.82%

Traditional ROI: 2.16%

Boston , MA

1 beds | 1 baths | 400 sq.ft.

$469,000

Airbnb cash on cash: 0.05%

Traditional cash on cash: 0.7%

Airbnb Rental Income: $2157

Traditional Rental Income: $1892

Airbnb ROI: 0.05%

Traditional ROI: 0.7%

Boston , MA

3 beds | 2 baths | 1,070 sq.ft.