Real Estate Investment Properties for Sale in Wayland, MA

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

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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
46 Juniper St Wayland, MA Turn-Key Income Machine ready for Tenants or perfect for owner occupant. Gutted down to th...	4 beds \| 2 baths \| 1,923 sq.ft.	$489,900	Airbnb cash on cash: 3.59% Traditional cash on cash: 5.94% Airbnb Rental Income: $3208 Traditional Rental Income: $3560 Airbnb ROI: 3.59% Traditional ROI: 5.94%
163 Front St Wayland, MA	4 beds \| 4 baths \| 5,044 sq.ft.	$589,000	Airbnb cash on cash: 2.92% Traditional cash on cash: 7.44% Airbnb Rental Income: $3208 Traditional Rental Income: $4970 Airbnb ROI: 2.92% Traditional ROI: 7.44%
239 Sawyer St Wayland, MA Fully rented, Cash-flowing 8-unit in the sought after city of New Bedford, located in a No...	17 beds \| 9 baths \| 9,149 sq.ft.	$1,150,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.17% Airbnb Rental Income: $null Traditional Rental Income: $6424 Airbnb ROI: N/A Traditional ROI: 4.17%
227 Egremont Plain Rd Wayland, MA	3 beds \| 4 baths \| 4,892 sq.ft.	$649,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 5.28% Airbnb Rental Income: $2489 Traditional Rental Income: $4267 Airbnb ROI: 1.35% Traditional ROI: 5.28%
166 Berkshire School Rd Wayland, MA Suzann Laverack Ward [email protected] 413-329-3031 HOUSATONIC REAL ESTATE	3 beds \| 2 baths \| 1,670 sq.ft.	$439,500	Airbnb cash on cash: 2.48% Traditional cash on cash: 4.74% Airbnb Rental Income: $2489 Traditional Rental Income: $2815 Airbnb ROI: 2.48% Traditional ROI: 4.74%
8 Turk Hollow Rd Wayland, MA OPEN HOUSE SUN 11/9 from 1PM-2PM Contemporary Log home, 1st time available for sale fr...	3 beds \| 2 baths \| 2,174 sq.ft.	$649,900	Airbnb cash on cash: 1.13% Traditional cash on cash: 3.72% Airbnb Rental Income: $2489 Traditional Rental Income: $3458 Airbnb ROI: 1.13% Traditional ROI: 3.72%
49 Northern Blvd Wayland, MA Your BEAUTIFUL Dream Beach House Awaits! This spectacular turnkey home on Plum Island offe...	5 beds \| 2 baths \| 2,246 sq.ft.	$1,780,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.84% Airbnb Rental Income: $null Traditional Rental Income: $3702 Airbnb ROI: N/A Traditional ROI: 0.84%
131 Division St Wayland, MA Located in Harwich at the Dennis Port town line, this solidly built home offers a great bl...	3 beds \| 1 baths \| 1,543 sq.ft.	$624,900	Airbnb cash on cash: 1.52% Traditional cash on cash: 2.36% Airbnb Rental Income: $2489 Traditional Rental Income: $2376 Airbnb ROI: 1.52% Traditional ROI: 2.36%
82 Stockbridge Ter Wayland, MA Prepare to be wowed when you visit this fully furnished luxury condo at Stockbridge Terrac...	4 beds \| 5 baths \| 3,395 sq.ft.	$1,250,000	Airbnb cash on cash: 0.16% Traditional cash on cash: 2.76% Airbnb Rental Income: $3208 Traditional Rental Income: $5510 Airbnb ROI: 0.16% Traditional ROI: 2.76%
153 Sesuit Neck Road Wayland, MA SESUIT NECK - NEW CONSTRUCTION...This recently developed 14.7 acre (12 acres are conservat...	5 beds \| N/A baths \| 4,100 sq.ft.	$4,995,000	Airbnb cash on cash: N/A Traditional cash on cash: -0.76% Airbnb Rental Income: $null Traditional Rental Income: $6852 Airbnb ROI: N/A Traditional ROI: -0.76%
248 East Rd Wayland, MA A luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pasto...	5 beds \| 5 baths \| 6,000 sq.ft.	$1,790,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.96% Airbnb Rental Income: $null Traditional Rental Income: $5585 Airbnb ROI: N/A Traditional ROI: 1.96%
14 Azalea Lane Wayland, MA Just completed! Ockway Village's final home! This spectacular property is unlike any other...	5 beds \| 6 baths \| 4,805 sq.ft.	$2,742,957	Airbnb cash on cash: N/A Traditional cash on cash: 1.07% Airbnb Rental Income: $null Traditional Rental Income: $6696 Airbnb ROI: N/A Traditional ROI: 1.07%
38 Buttonwood Lane Wayland, MA Discover the Remarkable Community of Turner Hill. Experience the perfect blend of eleganc...	3 beds \| 4 baths \| 3,114 sq.ft.	$2,550,000	Airbnb cash on cash: -0.62% Traditional cash on cash: 0.23% Airbnb Rental Income: $2489 Traditional Rental Income: $3894 Airbnb ROI: -0.62% Traditional ROI: 0.23%
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: 0.01% Traditional cash on cash: 0.66% Airbnb Rental Income: $3208 Traditional Rental Income: $3598 Airbnb ROI: 0.01% 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.	$585,000	Airbnb cash on cash: 3.96% Traditional cash on cash: 4.92% Airbnb Rental Income: $4022 Traditional Rental Income: $3688 Airbnb ROI: 3.96% Traditional ROI: 4.92%
4 Country Meadow Rd unit: 4 #4 Wayland, MA Welcome to 4 Country Meadow Road in Haverhill! This bright, spacious three level townhouse...	2 beds \| 2 baths \| 1,616 sq.ft.	$389,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 4.59% Airbnb Rental Income: $4022 Traditional Rental Income: $3002 Airbnb ROI: 5.04% Traditional ROI: 4.59%
2151 Route 2 Wayland, MA An exceptional 58.9-acre property along scenic Mohawk Trail in Charlemont! This unique pro...	5 beds \| 2 baths \| 3,553 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.36% Airbnb Rental Income: $null Traditional Rental Income: $4317 Airbnb ROI: N/A Traditional ROI: 5.36%
340 Vale St Wayland, MA Brand new single level home! Two bedroom 1,000 sqft home! 340 Vale St features modern ener...	2 beds \| 1 baths \| 1,012 sq.ft.	$369,980	Airbnb cash on cash: 6.87% Traditional cash on cash: 4.45% Airbnb Rental Income: $4022 Traditional Rental Income: $2322 Airbnb ROI: 6.87% Traditional ROI: 4.45%
1 Cole Road Wayland, MA NEW CONSTRUCTION modern farmhouse offering the space, craftsmanship, and lifestyle discern...	4 beds \| 3 baths \| 4,819 sq.ft.	$2,175,000	Airbnb cash on cash: -1.04% Traditional cash on cash: -0.19% Airbnb Rental Income: $3208 Traditional Rental Income: $4206 Airbnb ROI: -1.04% Traditional ROI: -0.19%
1605 Wisteria Way 1605 Wayland, MA Welcome to The Meadows, one of Waylandâs most desirable communities, nestled in a serene...	2 beds \| 3 baths \| 2,648 sq.ft.	$1,095,000	Airbnb cash on cash: 0.79% Traditional cash on cash: 1.31% Airbnb Rental Income: $4022 Traditional Rental Income: $3687 Airbnb ROI: 0.79% Traditional ROI: 1.31%
8 Fox Hollow unit: 8 #8 Wayland, MA BEST DEAL IN WAYLAND! Lovely 2 bed 2.5 bath townhouse w/attached garage on tranquil wooded...	2 beds \| 2 baths \| 1,718 sq.ft.	$624,900	Airbnb cash on cash: 1.1% Traditional cash on cash: 1.37% Airbnb Rental Income: $4022 Traditional Rental Income: $3321 Airbnb ROI: 1.1% Traditional ROI: 1.37%
10 Hayward Rd Wayland, MA Nicely maintained Colonial featuring 4 bedrooms, 4 full baths, and a 2-car garage, set in ...	4 beds \| 4 baths \| 1,988 sq.ft.	$999,000	Airbnb cash on cash: -0.06% Traditional cash on cash: 2.29% Airbnb Rental Income: $3208 Traditional Rental Income: $4667 Airbnb ROI: -0.06% Traditional ROI: 2.29%

Real Estate investment in Wayland, MA

There are 22 properties for sale in the city of Wayland . The median list price in Wayland is $824,450 and the average price per square foot is $256. In January 2026, the average monthly cash on cash return in Wayland is 3.00%. The average monthly rental income in Wayland is $3,798.

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

There are 22 investment properties available for sale in Wayland.

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

The ROI for Long-Term is higher than the Short-Term in Wayland with average rental income of $3,798.

Your search for investment property begins and ends here

Investment Property for Sale in Wayland, MA

46 Juniper St

Wayland, MA

4 beds | 2 baths | 1,923 sq.ft.

$489,900

Airbnb cash on cash: 3.59%

Traditional cash on cash: 5.94%

Airbnb Rental Income: $3208

Traditional Rental Income: $3560

Airbnb ROI: 3.59%

Traditional ROI: 5.94%

163 Front St

Wayland, MA

4 beds | 4 baths | 5,044 sq.ft.

$589,000

Airbnb cash on cash: 2.92%

Traditional cash on cash: 7.44%

Airbnb Rental Income: $3208

Traditional Rental Income: $4970

Airbnb ROI: 2.92%

Traditional ROI: 7.44%

239 Sawyer St

Wayland, MA

17 beds | 9 baths | 9,149 sq.ft.

$1,150,000

Airbnb cash on cash: N/A

Traditional cash on cash: 4.17%

Airbnb Rental Income: $null

Traditional Rental Income: $6424

Airbnb ROI: N/A

Traditional ROI: 4.17%

227 Egremont Plain Rd

Wayland, MA

3 beds | 4 baths | 4,892 sq.ft.

$649,000

Airbnb cash on cash: 1.35%

Traditional cash on cash: 5.28%

Airbnb Rental Income: $2489

Traditional Rental Income: $4267

Airbnb ROI: 1.35%

Traditional ROI: 5.28%

166 Berkshire School Rd

Wayland, MA

3 beds | 2 baths | 1,670 sq.ft.

$439,500

Airbnb cash on cash: 2.48%

Traditional cash on cash: 4.74%

Airbnb Rental Income: $2489

Traditional Rental Income: $2815

Airbnb ROI: 2.48%

Traditional ROI: 4.74%

8 Turk Hollow Rd

Wayland, MA

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

$649,900

Airbnb cash on cash: 1.13%

Traditional cash on cash: 3.72%

Airbnb Rental Income: $2489

Traditional Rental Income: $3458

Airbnb ROI: 1.13%

Traditional ROI: 3.72%

49 Northern Blvd

Wayland, MA

5 beds | 2 baths | 2,246 sq.ft.

$1,780,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.84%

Airbnb Rental Income: $null

Traditional Rental Income: $3702

Airbnb ROI: N/A

Traditional ROI: 0.84%

131 Division St

Wayland, MA

3 beds | 1 baths | 1,543 sq.ft.

$624,900

Airbnb cash on cash: 1.52%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $2489

Traditional Rental Income: $2376

Airbnb ROI: 1.52%