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
23 Rockwood Ln #23 Upton, MA Exceptional home in highly sought-after Rockwood Meadows blends style, comfort & ease of c...	2 beds \| 4 baths \| 4,139 sq.ft.	$1,049,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $5236 Airbnb ROI: N/A Traditional ROI: 2.79%
26 Fowler St Upton, MA Discover an energy-efficient three-story custom home on 1.55 acres of woodland retreat. Th...	2 beds \| 2 baths \| 1,632 sq.ft.	$575,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.31% Airbnb Rental Income: $null Traditional Rental Income: $3154 Airbnb ROI: N/A Traditional ROI: 3.31%
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: -1.5% Traditional cash on cash: 0.27% Airbnb Rental Income: $991 Traditional Rental Income: $4593 Airbnb ROI: -1.5% Traditional ROI: 0.27%
125 Bay Road Eastham , MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| N/A baths \| 1,662 sq.ft.	$2,195,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 0.17% Airbnb Rental Income: $5959 Traditional Rental Income: $3577 Airbnb ROI: 0.76% 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.	$1,350,000	Airbnb cash on cash: 0.36% Traditional cash on cash: 0.71% Airbnb Rental Income: $4038 Traditional Rental Income: $3609 Airbnb ROI: 0.36% Traditional ROI: 0.71%
496 Shore Road unit: 16 #16 Truro , MA This '' rare'' two bed'' , two full bath, ''YEAR ROUND'', second floor, direct ocean front...	2 beds \| 2 baths \| 607 sq.ft.	$720,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 1.08% Airbnb Rental Income: $2819 Traditional Rental Income: $2420 Airbnb ROI: 0.69% Traditional ROI: 1.08%
195 Ellis Landing Road Brewster , MA Just steps to beautiful Cape Cod Bay, sun and fun in the sand, breathtaking sunsets ... yo...	2 beds \| 1 baths \| 828 sq.ft.	$1,150,000	Airbnb cash on cash: 0.48% Traditional cash on cash: 0.19% Airbnb Rental Income: $3072 Traditional Rental Income: $2064 Airbnb ROI: 0.48% Traditional ROI: 0.19%
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.	$1,570,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 1.04% Airbnb Rental Income: $6412 Traditional Rental Income: $3418 Airbnb ROI: 2.24% Traditional ROI: 1.04%
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: 0.43% Traditional cash on cash: 0.87% Airbnb Rental Income: $4353 Traditional Rental Income: $4180 Airbnb ROI: 0.43% Traditional ROI: 0.87%
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: N/A Traditional cash on cash: 2.59% Airbnb Rental Income: $null Traditional Rental Income: $3102 Airbnb ROI: N/A Traditional ROI: 2.59%
663 Crowells Bog Road Brewster , MA Expanded 4 bedroom Cape-style home ideally located between Sheep Pond and Long Pond in Bre...	4 beds \| 4 baths \| 3,738 sq.ft.	$1,589,000	Airbnb cash on cash: 1.63% Traditional cash on cash: 2.01% Airbnb Rental Income: $6080 Traditional Rental Income: $5430 Airbnb ROI: 1.63% Traditional ROI: 2.01%
5 Glacier Drive Truro , MA Don't miss out on this beautifully renovated Cape Style home! This 3 bedroom home is move-...	3 beds \| N/A baths \| 1,734 sq.ft.	$989,000	Airbnb cash on cash: 1.9% Traditional cash on cash: 1.93% Airbnb Rental Income: $4038 Traditional Rental Income: $3202 Airbnb ROI: 1.9% Traditional ROI: 1.93%
307 W Main Street unit: 7 #7 Hyannis , MA Colonial Court Condominiums-NOW Vacant, bright morning sun and affordable 2 bedroom, 1 bat...	2 beds \| 1 baths \| 824 sq.ft.	$275,000	Airbnb cash on cash: 3.21% Traditional cash on cash: 4.41% Airbnb Rental Income: $2345 Traditional Rental Income: $2075 Airbnb ROI: 3.21% Traditional ROI: 4.41%
266 School Street Cotuit , MA This lovingly maintained cottage offers the perfect blend of Cape Cod charm and modern con...	2 beds \| 1 baths \| 1,000 sq.ft.	$625,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 1.8% Airbnb Rental Income: $2892 Traditional Rental Income: $2346 Airbnb ROI: 1.59% Traditional ROI: 1.8%
8 Cottage Street Wareham , MA Can you picture window boxes filled with seasonal flowers and crushed shells framing the f...	3 beds \| 1 baths \| 964 sq.ft.	$350,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 4.85% Airbnb Rental Income: $2118 Traditional Rental Income: $2265 Airbnb ROI: 2.76% Traditional ROI: 4.85%
118 Driftwood Lane South Yarmouth , MA Cape Cod Luxury Waterfront Living on Follins Pond~Bass River! Imagine waking up to blue sk...	4 beds \| 5 baths \| 3,978 sq.ft.	$3,375,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.71% Airbnb Rental Income: $2497 Traditional Rental Income: $7060 Airbnb ROI: -0.94% Traditional ROI: 0.71%

Real Estate investment in Upton, MA

There are 3 properties for sale in the city of Upton . The median list price in Upton is $1,049,000 and the average price per square foot is $306. In October 2025, the average monthly cash on cash return in Upton is 3.00%. The average monthly rental income in Upton is $4,484.

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

There are 3 investment properties available for sale in Upton.

In 2025, 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

23 Rockwood Ln #23

Upton, MA

2 beds | 4 baths | 4,139 sq.ft.

$1,049,000

Airbnb cash on cash: N/A

Traditional cash on cash: 2.79%

Airbnb Rental Income: $null

Traditional Rental Income: $5236

Airbnb ROI: N/A

Traditional ROI: 2.79%

26 Fowler St

Upton, MA

2 beds | 2 baths | 1,632 sq.ft.

$575,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.31%

Airbnb Rental Income: $null

Traditional Rental Income: $3154

Airbnb ROI: N/A

Traditional ROI: 3.31%

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: -1.5%

Traditional cash on cash: 0.27%

Airbnb Rental Income: $991

Traditional Rental Income: $4593

Airbnb ROI: -1.5%

Traditional ROI: 0.27%

Eastham , MA

3 beds | N/A baths | 1,662 sq.ft.

$2,195,000

Airbnb cash on cash: 0.76%

Traditional cash on cash: 0.17%

Airbnb Rental Income: $5959

Traditional Rental Income: $3577

Airbnb ROI: 0.76%

Traditional ROI: 0.17%

Truro , MA

3 beds | 2 baths | 2,018 sq.ft.

$1,350,000

Airbnb cash on cash: 0.36%

Traditional cash on cash: 0.71%

Airbnb Rental Income: $4038

Traditional Rental Income: $3609

Airbnb ROI: 0.36%

Traditional ROI: 0.71%

Truro , MA

2 beds | 2 baths | 607 sq.ft.

$720,000

Airbnb cash on cash: 0.69%

Traditional cash on cash: 1.08%

Airbnb Rental Income: $2819

Traditional Rental Income: $2420

Airbnb ROI: 0.69%

Traditional ROI: 1.08%

Brewster , MA

2 beds | 1 baths | 828 sq.ft.

$1,150,000

Airbnb cash on cash: 0.48%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $3072

Traditional Rental Income: $2064

Airbnb ROI: 0.48%

Traditional ROI: 0.19%

Harwich , MA

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%

Chatham , MA

3 beds | 2 baths | 2,307 sq.ft.

$1,570,000

Airbnb cash on cash: 2.24%