Airbnb Properties for Sale in Wayland, MA

Looking for a vacation rental investment in Wayland, MA with high ROI ?

Explore a range of newly added short-term rental homes in Wayland, MA. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Wayland, MA

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
115 Bridge St Wayland, MA	4 beds \| 2 baths \| 2,112 sq.ft.	$499,000	Airbnb cash on cash: 5.95% Traditional cash on cash: 4.33% Airbnb Rental Income: $4803 Traditional Rental Income: $3056 Airbnb ROI: 5.95% Traditional ROI: 4.33%
47 East Chop Drive #3 Wayland, MA East Chop Water Front Luxury Condominiums -- This 2-bedroom, waterfront condominium, the "...	2 beds \| 1 baths \| N/A	$1,995,000	Airbnb cash on cash: 0.13% Traditional cash on cash: -0.93% Airbnb Rental Income: $5349 Traditional Rental Income: $2302 Airbnb ROI: 0.13% Traditional ROI: -0.93%
47 East Chop Drive #4 Wayland, MA East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condom...	2 beds \| 1 baths \| N/A	$1,995,000	Airbnb cash on cash: 0.13% Traditional cash on cash: -0.93% Airbnb Rental Income: $5349 Traditional Rental Income: $2302 Airbnb ROI: 0.13% Traditional ROI: -0.93%
11 John Wesley Avenue Wayland, MA East Chop Living in this 4 Bedroom Victorian home perched near the shoreline in Oak Bluffs...	4 beds \| 2 baths \| 1,304 sq.ft.	$1,550,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.85% Airbnb Rental Income: $4803 Traditional Rental Income: $3277 Airbnb ROI: 1.22% Traditional ROI: 0.85%
8 Turk Hollow Rd Wayland, MA Contemporary Log home, 1st time available for sale from its original owners. 1.52 acre pri...	3 beds \| 2 baths \| 2,174 sq.ft.	$679,900	Airbnb cash on cash: 3.94% Traditional cash on cash: 3.52% Airbnb Rental Income: $4701 Traditional Rental Income: $3458 Airbnb ROI: 3.94% Traditional ROI: 3.52%
127 Old Joe Rd Wayland, MA Antonio M Segalla [email protected] 413-329-4075 LANCE VERMEULEN RE, INC	4 beds \| 2 baths \| 1,560 sq.ft.	$475,000	Airbnb cash on cash: 6.6% Traditional cash on cash: 5.06% Airbnb Rental Income: $4803 Traditional Rental Income: $3127 Airbnb ROI: 6.6% Traditional ROI: 5.06%
367 North Plain Rd Wayland, MA 1880 4 Bedroom Colonial in a beautiful Pastoral setting. Open Living and Kitchen plan.Perm...	4 beds \| 3 baths \| 2,422 sq.ft.	$749,000	Airbnb cash on cash: 3.23% Traditional cash on cash: 2.65% Airbnb Rental Income: $4803 Traditional Rental Income: $3408 Airbnb ROI: 3.23% Traditional ROI: 2.65%
163 Main St Wayland, MA Antique Farmhouse in the Village Center District. Built in 1802 this delightful 3-BR home ...	3 beds \| 2 baths \| 2,152 sq.ft.	$499,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 5.15% Airbnb Rental Income: $4701 Traditional Rental Income: $3599 Airbnb ROI: 5.43% Traditional ROI: 5.15%
26 Winthrop Avenue Wayland, MA Hidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece ...	1 beds \| 1 baths \| N/A	$899,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 0.86% Airbnb Rental Income: $4015 Traditional Rental Income: $1988 Airbnb ROI: 2.26% Traditional ROI: 0.86%
81 Bedford St Wayland, MA Located right across the street from Hornstra Farm Dairy (the old Peaceful meadows) Great ...	4 beds \| 2 baths \| 1,486 sq.ft.	$639,000	Airbnb cash on cash: 4.24% Traditional cash on cash: 3.72% Airbnb Rental Income: $4803 Traditional Rental Income: $3507 Airbnb ROI: 4.24% Traditional ROI: 3.72%
3 Van Schaack Rd Wayland, MA Cortney K Dupont [email protected] COHEN & WHITE ASSOCIATES	3 beds \| 1 baths \| 1,200 sq.ft.	$425,000	Airbnb cash on cash: 7.37% Traditional cash on cash: 4.43% Airbnb Rental Income: $4701 Traditional Rental Income: $2556 Airbnb ROI: 7.37% Traditional ROI: 4.43%
47 Gale Ave Wayland, MA Brandon White [email protected] 413-637-1086 COHEN & WHITE ASSOCIATES	3 beds \| 2 baths \| 1,456 sq.ft.	$455,000	Airbnb cash on cash: 6.59% Traditional cash on cash: 5.46% Airbnb Rental Income: $4701 Traditional Rental Income: $3246 Airbnb ROI: 6.59% Traditional ROI: 5.46%
314 Main St Wayland, MA Attention investors and contractors this could be your next project. A prime opportunity i...	4 beds \| 2 baths \| 1,965 sq.ft.	$350,000	Airbnb cash on cash: 8.78% Traditional cash on cash: 7.86% Airbnb Rental Income: $4803 Traditional Rental Income: $3511 Airbnb ROI: 8.78% Traditional ROI: 7.86%
179 South Main St Wayland, MA Antonio M Segalla [email protected] 413-329-4075 LANCE VERMEULEN RE, INC	3 beds \| 3 baths \| 1,536 sq.ft.	$345,000	Airbnb cash on cash: 9.26% Traditional cash on cash: 8.38% Airbnb Rental Income: $4701 Traditional Rental Income: $3444 Airbnb ROI: 9.26% Traditional ROI: 8.38%
12 & 14 Maple Avenue Wayland, MA Two Historic Oak Bluffs Cottages - Prime Location - Deeded Separately Perched atop a gentl...	4 beds \| 4 baths \| 1,600 sq.ft.	$1,830,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 0.66% Airbnb Rental Income: $4803 Traditional Rental Income: $3598 Airbnb ROI: 0.79% Traditional ROI: 0.66%
19 Hawthorne Rd Wayland, MA Cortney K Dupont [email protected] COHEN & WHITE ASSOCIATES	2 beds \| 3 baths \| 1,935 sq.ft.	$679,000	Airbnb cash on cash: 5.02% Traditional cash on cash: 4.11% Airbnb Rental Income: $5349 Traditional Rental Income: $3688 Airbnb ROI: 5.02% Traditional ROI: 4.11%
Lot 83 Rice Rd. Wayland, MA New Custom Split Entry Ranch to be built appx 1 mi to the Sturbridge town line and with an...	3 beds \| 2 baths \| 1,709 sq.ft.	$549,900	Airbnb cash on cash: 5.97% Traditional cash on cash: 5.56% Airbnb Rental Income: $4701 Traditional Rental Income: $3520 Airbnb ROI: 5.97% Traditional ROI: 5.56%
Lot 4 Old County Rd. Wayland, MA New Custom Ranch with a walk out lower level w finished room to be built on a tree-lined s...	3 beds \| 1 baths \| 1,464 sq.ft.	$499,000	Airbnb cash on cash: 6.71% Traditional cash on cash: 5.19% Airbnb Rental Income: $4701 Traditional Rental Income: $3017 Airbnb ROI: 6.71% Traditional ROI: 5.19%
1068 Main St Wayland, MA Very unique duplex in the heart of Housatonic! This very cool house combines antique charm...	4 beds \| 2 baths \| 1,634 sq.ft.	$499,000	Airbnb cash on cash: 5.93% Traditional cash on cash: 4.79% Airbnb Rental Income: $4803 Traditional Rental Income: $3281 Airbnb ROI: 5.93% Traditional ROI: 4.79%
519 Kirchner Rd Wayland, MA Nestled on a generous lot surrounded by lush New England greenery, this charming home offe...	3 beds \| 2 baths \| 2,595 sq.ft.	$334,900	Airbnb cash on cash: 7.85% Traditional cash on cash: 7.38% Airbnb Rental Income: $4701 Traditional Rental Income: $3580 Airbnb ROI: 7.85% Traditional ROI: 7.38%
2375 Williams St Wayland, MA UPDATE: OFFERS DUE MONDAY JULY 21st AT 2 p.m. PENDING PROBATE APPROVAL. Attention handy...	3 beds \| 1 baths \| 1,680 sq.ft.	$399,900	Airbnb cash on cash: 7.34% Traditional cash on cash: 4.89% Airbnb Rental Income: $4701 Traditional Rental Income: $2810 Airbnb ROI: 7.34% Traditional ROI: 4.89%
7 Assinippi Ave #207 Wayland, MA	2 beds \| 2 baths \| 1,054 sq.ft.	$419,900	Airbnb cash on cash: 6.59% Traditional cash on cash: 2.67% Airbnb Rental Income: $5349 Traditional Rental Income: $2726 Airbnb ROI: 6.59% Traditional ROI: 2.67%
10 Simonne Ln Wayland, MA BACK ON MARKET DUE TO BUYERS FINANCING - Welcome to your dream home in desired Pepperell n...	3 beds \| 1 baths \| 1,300 sq.ft.	$499,900	Airbnb cash on cash: 5.71% Traditional cash on cash: 3.13% Airbnb Rental Income: $4701 Traditional Rental Income: $2526 Airbnb ROI: 5.71% Traditional ROI: 3.13%

Vacation Rentals in Wayland

There are 24 vacation rental properties available for sale in the city of Wayland . The median list price of Airbnb properties available for sale in Wayland is $849,900 and the average price per square foot is $277. The cash on cash return on vacation rentals in Wayland is 4.00%. The average monthly short term rental income in Wayland is $4,803.

Wayland, MA Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 24 Airbnb properties available for sale in Wayland.

In 2025, the best neighborhood to buy short term rental property is Wayland.

In September 2025, the average Airbnb occupancy rate in Wayland is 49%.

Airbnb data on vacation rentals in Wayland, MA is available at Mashvisor. You can access data such as listings, real-time pricing trends, Wayland, MA market insights, guest information and booking details, seasonality trends and historical Wayland, MA Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Wayland, MA

115 Bridge St

Wayland, MA

4 beds | 2 baths | 2,112 sq.ft.

$499,000

Airbnb cash on cash: 5.95%

Traditional cash on cash: 4.33%

Airbnb Rental Income: $4803

Traditional Rental Income: $3056

Airbnb ROI: 5.95%

Traditional ROI: 4.33%

47 East Chop Drive #3

Wayland, MA

2 beds | 1 baths | N/A

$1,995,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: -0.93%

Airbnb Rental Income: $5349

Traditional Rental Income: $2302

Airbnb ROI: 0.13%

Traditional ROI: -0.93%

47 East Chop Drive #4

Wayland, MA

2 beds | 1 baths | N/A

$1,995,000

Airbnb cash on cash: 0.13%

Traditional cash on cash: -0.93%

Airbnb Rental Income: $5349

Traditional Rental Income: $2302

Airbnb ROI: 0.13%

Traditional ROI: -0.93%

11 John Wesley Avenue

Wayland, MA

4 beds | 2 baths | 1,304 sq.ft.

$1,550,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 0.85%

Airbnb Rental Income: $4803

Traditional Rental Income: $3277

Airbnb ROI: 1.22%

Traditional ROI: 0.85%

8 Turk Hollow Rd

Wayland, MA

3 beds | 2 baths | 2,174 sq.ft.

$679,900

Airbnb cash on cash: 3.94%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $4701

Traditional Rental Income: $3458

Airbnb ROI: 3.94%

Traditional ROI: 3.52%

127 Old Joe Rd

Wayland, MA

4 beds | 2 baths | 1,560 sq.ft.

$475,000

Airbnb cash on cash: 6.6%

Traditional cash on cash: 5.06%

Airbnb Rental Income: $4803

Traditional Rental Income: $3127

Airbnb ROI: 6.6%

Traditional ROI: 5.06%

367 North Plain Rd

Wayland, MA

4 beds | 3 baths | 2,422 sq.ft.

$749,000

Airbnb cash on cash: 3.23%

Traditional cash on cash: 2.65%

Airbnb Rental Income: $4803

Traditional Rental Income: $3408

Airbnb ROI: 3.23%

Traditional ROI: 2.65%

163 Main St

Wayland, MA

3 beds | 2 baths | 2,152 sq.ft.

$499,000

Airbnb cash on cash: 5.43%

Traditional cash on cash: 5.15%

Airbnb Rental Income: $4701

Traditional Rental Income: $3599

Airbnb ROI: 5.43%