Real Estate Investment Properties for Sale in Tolland, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
32 Woodchuck Hollow Tolland, MA Kim Bergland [email protected] 413-250-6149 RED HORSE REAL ESTATE, LLC	3 beds \| 2 baths \| 1,659 sq.ft.	$429,000	Airbnb cash on cash: 6.45% Traditional cash on cash: 7.1% Airbnb Rental Income: $4226 Traditional Rental Income: $3593 Airbnb ROI: 6.45% Traditional ROI: 7.1%
1259 East Otis Rd Tolland, MA Adam J Dingman [email protected] 413-464-1381 BERKSHIRE HATHAWAY HOMESERVICES BARNB...	3 beds \| 2 baths \| 1,400 sq.ft.	$344,999	Airbnb cash on cash: 8.53% Traditional cash on cash: 7.67% Airbnb Rental Income: $4226 Traditional Rental Income: $3055 Airbnb ROI: 8.53% Traditional ROI: 7.67%
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%
20 Hardings Beach Road Chatham , MA In a coveted Harding's Beach location, this fully renovated Chatham home offers sweeping v...	4 beds \| 4 baths \| 2,770 sq.ft.	$1,995,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 1.38% Airbnb Rental Income: $5632 Traditional Rental Income: $4925 Airbnb ROI: 1.15% Traditional ROI: 1.38%
125 Bay Road Eastham , MA Impeccably renovated and maintained, this is waterfront perfection with a private beach an...	3 beds \| 3 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%
73 Joshua Jethro Road Chatham , MA Located in Chatham's highly sought after Riverbay Estates community, this 3-bedroom, 2-bat...	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.	$1,850,000	Airbnb cash on cash: 0.39% Traditional cash on cash: 0.82% Airbnb Rental Income: $4353 Traditional Rental Income: $4180 Airbnb ROI: 0.39% Traditional ROI: 0.82%
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%
53 Chilton Lane Brewster , MA Enjoy the scenic pond view from the living room and main bedroom of this condo! In fact, i...	2 beds \| 2 baths \| 935 sq.ft.	$389,500	Airbnb cash on cash: 3.03% Traditional cash on cash: 3.64% Airbnb Rental Income: $3072 Traditional Rental Income: $2594 Airbnb ROI: 3.03% Traditional ROI: 3.64%
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 \| 3 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: 3.16% Traditional cash on cash: 4.41% Airbnb Rental Income: $2328 Traditional Rental Income: $2075 Airbnb ROI: 3.16% 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%
996 Main Street Cotuit , MA Relaxed coastal living meets glorious views at this harbor front retreat in the heart of C...	4 beds \| 2 baths \| 4,303 sq.ft.	$5,500,000	Airbnb cash on cash: -0.66% Traditional cash on cash: -0.68% Airbnb Rental Income: $5178 Traditional Rental Income: $4048 Airbnb ROI: -0.66% Traditional ROI: -0.68%

Real Estate investment in Tolland, MA

There are 2 properties for sale in the city of Tolland . The median list price in Tolland is $387,000 and the average price per square foot is $253. In September 2025, the average monthly cash on cash return in Tolland is 7.00%. The average monthly rental income in Tolland is $3,324.

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

There are 2 investment properties available for sale in Tolland.

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

The ROI for Short-Term is higher than the Long-Term in Tolland with average rental income of $4,226.

Your search for investment property begins and ends here

Investment Property for Sale in Tolland, MA

32 Woodchuck Hollow

Tolland, MA

3 beds | 2 baths | 1,659 sq.ft.

$429,000

Airbnb cash on cash: 6.45%

Traditional cash on cash: 7.1%

Airbnb Rental Income: $4226

Traditional Rental Income: $3593

Airbnb ROI: 6.45%

Traditional ROI: 7.1%

1259 East Otis Rd

Tolland, MA

3 beds | 2 baths | 1,400 sq.ft.

$344,999

Airbnb cash on cash: 8.53%

Traditional cash on cash: 7.67%

Airbnb Rental Income: $4226

Traditional Rental Income: $3055

Airbnb ROI: 8.53%

Traditional ROI: 7.67%

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%

Chatham , MA

4 beds | 4 baths | 2,770 sq.ft.

$1,995,000

Airbnb cash on cash: 1.15%

Traditional cash on cash: 1.38%

Airbnb Rental Income: $5632

Traditional Rental Income: $4925

Airbnb ROI: 1.15%

Traditional ROI: 1.38%

Eastham , MA

3 beds | 3 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%

Chatham , MA

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

$1,570,000

Airbnb cash on cash: 2.24%