Real Estate Investment Properties for Sale in Westborough, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
12 Appleseed Dr Westborough, MA A colonial with great potential. Nestled in one of Westborough's most desirable neighborho...	4 beds \| 4 baths \| 3,451 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.46% Airbnb Rental Income: $null Traditional Rental Income: $5535 Airbnb ROI: N/A Traditional ROI: 3.46%
43 Church St Westborough, MA An Italianate gem, meticulously restored over a 4 yr renovation, this home is a testament ...	4 beds \| 4 baths \| 4,850 sq.ft.	$1,800,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.72% Airbnb Rental Income: $null Traditional Rental Income: $6528 Airbnb ROI: N/A Traditional ROI: 1.72%
21 South St unit: 31 #31 Westborough, MA Welcome to 21 South St, Unit 31, Westborough! Seller will pay $5,000 towards buyers closin...	1 beds \| 1 baths \| 602 sq.ft.	$249,900	Airbnb cash on cash: -0.86% Traditional cash on cash: 3.27% Airbnb Rental Income: $1473 Traditional Rental Income: $2014 Airbnb ROI: -0.86% Traditional ROI: 3.27%
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%
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%
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%
27 Quaker Lane Harwich , MA This Harwich home is set in the perfect location! Ideally situated near popular restaurant...	2 beds \| 1 baths \| 1,019 sq.ft.	$569,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 2.74% Airbnb Rental Income: $2729 Traditional Rental Income: $2298 Airbnb ROI: 2.34% Traditional ROI: 2.74%
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%
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: -1.2% Traditional cash on cash: 1.8% Airbnb Rental Income: $942 Traditional Rental Income: $2346 Airbnb ROI: -1.2% Traditional ROI: 1.8%
14 Colonial Road Webster , MA 14 Colonial Drive in Webster is a must see! Located in a sought-after Webster Lake neighbo...	3 beds \| 2 baths \| 1,248 sq.ft.	$399,900	Airbnb cash on cash: 3.39% Traditional cash on cash: 5.76% Airbnb Rental Income: $2687 Traditional Rental Income: $2938 Airbnb ROI: 3.39% Traditional ROI: 5.76%
1203 Bennington St Winthrop , MA 1203 Bennington St, Winthrop, MA 02128 \| Single Family Residential	5 beds \| 3 baths \| 1,568 sq.ft.	$793,721	Airbnb cash on cash: 1.21% Traditional cash on cash: 3.28% Airbnb Rental Income: $3388 Traditional Rental Income: $4159 Airbnb ROI: 1.21% Traditional ROI: 3.28%
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 \| N/A baths \| 3,978 sq.ft.	$3,375,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.71% Airbnb Rental Income: $2197 Traditional Rental Income: $7060 Airbnb ROI: -1.02% Traditional ROI: 0.71%
200 Cove Way unit: 614 #614 Quincy , MA Are you an outdoors type that enjoys sailing, swimming, tennis or do you like dining out, ...	2 beds \| 2 baths \| 1,051 sq.ft.	$415,000	Airbnb cash on cash: -1.41% Traditional cash on cash: 2.25% Airbnb Rental Income: $1458 Traditional Rental Income: $2449 Airbnb ROI: -1.41% Traditional ROI: 2.25%
35 Bayshore Drive Mashpee , MA Set along the marshfront with views of Hamblin Pond, this beautiful home offers a peaceful...	4 beds \| 4 baths \| 3,236 sq.ft.	$1,395,500	Airbnb cash on cash: 2.05% Traditional cash on cash: 2.63% Airbnb Rental Income: $5855 Traditional Rental Income: $5443 Airbnb ROI: 2.05% Traditional ROI: 2.63%
93 Chapman Place unit: 93 #93 LEOMINSTER , MA Welcome home to this beautifully maintained townhouse in the desirable Chapman Place commu...	2 beds \| 2 baths \| 1,384 sq.ft.	$389,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.01% Airbnb Rental Income: $null Traditional Rental Income: $3017 Airbnb ROI: N/A Traditional ROI: 5.01%
173 Hillsdale Rd Egremont , MA Nestled in a secluded, serene setting and surrounded by lush gardens, fruit trees, wildlif...	5 beds \| 5 baths \| 4,842 sq.ft.	$2,150,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 2.08% Airbnb Rental Income: $5815 Traditional Rental Income: $7316 Airbnb ROI: 0.75% Traditional ROI: 2.08%

Real Estate investment in Westborough, MA

There are 3 properties for sale in the city of Westborough . The median list price in Westborough is $899,900 and the average price per square foot is $303. In December 2025, the average monthly cash on cash return in Westborough is 3.00%. The average monthly rental income in Westborough is $5,535.

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

There are 3 investment properties available for sale in Westborough.

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

The ROI for Long-Term is higher than the Short-Term in Westborough with average rental income of $5,535.

Your search for investment property begins and ends here

Investment Property for Sale in Westborough, MA

12 Appleseed Dr

Westborough, MA

4 beds | 4 baths | 3,451 sq.ft.

$899,900

Airbnb cash on cash: N/A

Traditional cash on cash: 3.46%

Airbnb Rental Income: $null

Traditional Rental Income: $5535

Airbnb ROI: N/A

Traditional ROI: 3.46%

43 Church St

Westborough, MA

4 beds | 4 baths | 4,850 sq.ft.

$1,800,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.72%

Airbnb Rental Income: $null

Traditional Rental Income: $6528

Airbnb ROI: N/A

Traditional ROI: 1.72%

21 South St unit: 31 #31

Westborough, MA

1 beds | 1 baths | 602 sq.ft.

$249,900

Airbnb cash on cash: -0.86%

Traditional cash on cash: 3.27%

Airbnb Rental Income: $1473

Traditional Rental Income: $2014

Airbnb ROI: -0.86%

Traditional ROI: 3.27%

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%

Eastham , MA

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%

Truro , MA

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%

Chatham , MA

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%

Harwich , MA

2 beds | 1 baths | 1,019 sq.ft.

$569,000

Airbnb cash on cash: 2.34%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $2729

Traditional Rental Income: $2298

Airbnb ROI: 2.34%

Traditional ROI: 2.74%

Harwich , MA

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

$799,000