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
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
115 Bridge StWayland, MA
|
4 beds | 2 baths | 2,112 sq.ft. |
$499,000 |
Airbnb cash on cash: 5.95%
|
163 Front StWayland, MA
|
4 beds | 4 baths | 5,044 sq.ft. |
$589,000 |
Airbnb cash on cash: 5.34%
|
239 Sawyer StWayland, MAFully 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
|
227 Egremont Plain RdWayland, MA
|
3 beds | 4 baths | 4,892 sq.ft. |
$649,000 |
Airbnb cash on cash: 4.39%
|
Lot 5 Northside RdWayland, MAAre you looking for a 20+/- acre lot to build a beautiful custom home? This is it! Lot cle... |
4 beds | 3 baths | 2,550 sq.ft. |
$779,900 |
Airbnb cash on cash: 2.9%
|
11 Bow North --Wayland, MAWaterfront at Sherwood Greens! Welcome to lakefront living on Long Bow Lake. Just in ti... |
4 beds | 3 baths | 1,839 sq.ft. |
$529,900 |
Airbnb cash on cash: 5.71%
|
47 East Chop Drive #1Wayland, MAEast Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condomin... |
1 beds | 1 baths | N/A |
$1,495,000 |
Airbnb cash on cash: -0.17%
|
47 East Chop Drive #5Wayland, MAEast Chop/Oak Bluffs waterfront -- The ultimate in waterfront living experiences, this 1-b... |
1 beds | 1 baths | N/A |
$1,495,000 |
Airbnb cash on cash: -0.17%
|
47 East Chop Drive #3Wayland, MAEast 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%
|
47 East Chop Drive #2Wayland, MAEast Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, "Cotta... |
1 beds | 1 baths | N/A |
$1,495,000 |
Airbnb cash on cash: -0.17%
|
47 East Chop Drive #4Wayland, MAEast 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%
|
166 Berkshire School RdWayland, MASuzann Laverack Ward [email protected] 413-329-3031 HOUSATONIC REAL ESTATE |
3 beds | 2 baths | 1,670 sq.ft. |
$475,000 |
Airbnb cash on cash: 6.37%
|
567 South Main StWayland, MA
|
9 beds | 7 baths | 5,267 sq.ft. |
$895,000 |
Airbnb cash on cash: N/A
|
11 John Wesley AvenueWayland, MAEast 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%
|
8 Turk Hollow RdWayland, MAContemporary Log home, 1st time available for sale from its original owners. 1.52 acre pri... |
3 beds | 2 baths | 2,174 sq.ft. |
$669,900 |
Airbnb cash on cash: 3.94%
|
127 Old Joe RdWayland, MAAntonio 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%
|
1 Terra Ferma DrWayland, MAAntonio M Segalla [email protected] 413-329-4075 LANCE VERMEULEN RE, INC |
3 beds | 2 baths | 1,750 sq.ft. |
$349,000 |
Airbnb cash on cash: 9.91%
|
25 Brayton Point RoadWayland, MAWESTPORT HARBOR - TWO HOME COMPOUND Located in one of Westport's most sought-after areas... |
5 beds | 7 baths | 6,656 sq.ft. |
$3,300,000 |
Airbnb cash on cash: N/A
|
367 North Plain RdWayland, MA1880 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%
|
26 Winthrop AvenueWayland, MAHidden behind a wall of vegetation on Winthrop Avenue this is a little 'oasis' of a piece ... |
1 beds | 1 baths | N/A |
$849,000 |
Airbnb cash on cash: 2.45%
|
82 Stockbridge TerWayland, MAPrepare to be wowed when you visit this fully furnished luxury condo at Stockbridge Terrac... |
4 beds | 5 baths | 3,395 sq.ft. |
$1,350,000 |
Airbnb cash on cash: 1.15%
|
81 Bedford StWayland, MALocated right across the street from Hornstra Farm Dairy (the old Peaceful meadows) Great ... |
4 beds | 2 baths | 1,486 sq.ft. |
$619,000 |
Airbnb cash on cash: 4.4%
|
978 Clayton Mill River RdWayland, MAThe Ephraim Chapin House was built in Chicopee c. 1725. In 1979 this handsome home & taver... |
4 beds | 5 baths | 4,492 sq.ft. |
$1,750,000 |
Airbnb cash on cash: 0.6%
|
2 Monomoy LaneWayland, MAModern Luxury Meets Coastal Charm in Orleans, Cape Cod Welcome to an exclusive enclave of ... |
4 beds | 4 baths | 5,035 sq.ft. |
$2,795,000 |
Airbnb cash on cash: -0.79%
|
3 Van Schaack RdWayland, MACortney K Dupont [email protected] COHEN & WHITE ASSOCIATES |
3 beds | 1 baths | 1,200 sq.ft. |
$425,000 |
Airbnb cash on cash: 7.37%
|
1196 Bancroft RdWayland, MALocated on the east side of Becket is this beautiful home with a spring fed swimming pond ... |
3 beds | 2 baths | 2,496 sq.ft. |
$569,000 |
Airbnb cash on cash: 5.12%
|
248 East RdWayland, MAA luxurious home on one of the most scenic roads in The Berkshires, surrounded by 15 pasto... |
5 beds | 5 baths | 6,000 sq.ft. |
$1,890,000 |
Airbnb cash on cash: N/A
|
47 Gale AveWayland, MABrandon 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%
|
14 Azalea LaneWayland, MAJust 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
|
87 Alford RdWayland, MAAntonio M Segalla [email protected] 413-329-4075 LANCE VERMEULEN RE, INC |
3 beds | 2 baths | 2,990 sq.ft. |
$1,995,000 |
Airbnb cash on cash: 0.27%
|
314 Main StWayland, MAAttention 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%
|
29 Main StWayland, MA
|
12 beds | 7 baths | 8,881 sq.ft. |
$1,675,000 |
Airbnb cash on cash: N/A
|
116 Brush Hill RdWayland, MACustom Built Craftsman Contemporary Home nestled in a beautifully landscaped property with... |
4 beds | 5 baths | 5,300 sq.ft. |
$3,750,000 |
Airbnb cash on cash: -1.14%
|
12 Center Street unit: 1 #1Wayland, MAMeticulously restored 1870s Second Empire home thoroughly re-engineered for luxurious 2025... |
4 beds | 5 baths | 1,904 sq.ft. |
$2,750,000 |
Airbnb cash on cash: -0.15%
|
179 South Main StWayland, MAAntonio 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%
|
188 Hillsdale RdWayland, MAHelen Mullany [email protected] 413-429-7733 HELEN MULLANY REAL ESTATE, LLC |
3 beds | 3 baths | 2,072 sq.ft. |
$995,000 |
Airbnb cash on cash: 2.25%
|
232 Harrington RdWayland, MAKim Bergland [email protected] 413-250-6149 RED HORSE REAL ESTATE, LLC |
4 beds | 4 baths | 3,084 sq.ft. |
$639,000 |
Airbnb cash on cash: 4.62%
|
12 & 14 Maple AvenueWayland, MATwo 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%
|
240 Smith StreetWayland, MAEscape to your own private country estate on 24 picturesque acres. Perfect for the discern... |
3 beds | 3 baths | 3,156 sq.ft. |
$2,499,000 |
Airbnb cash on cash: -0.33%
|
82 Central TpkeWayland, MADiscover this stunning Contemporary Ranch in Sutton, featuring 10 rooms, 4 bedrooms, 2 1/2... |
4 beds | 3 baths | 2,584 sq.ft. |
$849,900 |
Airbnb cash on cash: 2.89%
|
Real Estate investment in Wayland, MA
There are 57 properties for sale in the city of Wayland . The median list price in Wayland is $885,000 and the average price per square foot is $278. In September 2025, the average monthly cash on cash return in Wayland is 3.00%. The average monthly rental income in Wayland is $3,805.