Real Estate Investment Properties for Sale in Oak Bluffs, MA

Looking for investment property in Oak Bluffs, MA with high ROI ?

Explore a variety of short-term homes & houses in Oak Bluffs, MA. Invest wisely with VRBO & Oak Bluffs, MA Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Boro Investment Property for Sale in Oak Bluffs, MA

Search for Boro Investment Property for Sale in Oak Bluffs, Massachusetts. Browse all of Mashvisor’s Boro Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 36 Boro Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
1 Cottage Park Oak Bluffs, MA The Star Spangled Manor, a beautifully restored gem nestled in the heart of Oak Bluffs wit...	3 beds \| 3 baths \| 987 sq.ft.	$925,000	Airbnb cash on cash: 1.46% Traditional cash on cash: 1.58% Airbnb Rental Income: $3278 Traditional Rental Income: $2647 Airbnb ROI: 1.46% Traditional ROI: 1.58%
8 School House Village Oak Bluffs, MA Located in a desirable Oak Bluffs neighborhood, surrounded by mature plantings and attract...	4 beds \| 4 baths \| 2,336 sq.ft.	$1,575,000	Airbnb cash on cash: 0.42% Traditional cash on cash: 1.56% Airbnb Rental Income: $3515 Traditional Rental Income: $4409 Airbnb ROI: 0.42% Traditional ROI: 1.56%
47 Winemack Street Oak Bluffs, MA Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent th...	2 beds \| 1 baths \| 742 sq.ft.	$1,250,000	Airbnb cash on cash: 1.41% Traditional cash on cash: 0.9% Airbnb Rental Income: $4315 Traditional Rental Income: $2817 Airbnb ROI: 1.41% Traditional ROI: 0.9%
4 High Meadow Lane Oak Bluffs, MA Classic Post & Beam set in Meadow View Farms This bright and charming four-bedroom home si...	4 beds \| 4 baths \| 2,810 sq.ft.	$2,445,000	Airbnb cash on cash: -0.24% Traditional cash on cash: 0.39% Airbnb Rental Income: $3515 Traditional Rental Income: $4171 Airbnb ROI: -0.24% Traditional ROI: 0.39%
267 Barnes Road Oak Bluffs, MA Enjoy waterfront living at its best with 163' of Lagoon frontage, including a private sand...	3 beds \| 6 baths \| 4,046 sq.ft.	$4,500,000	Airbnb cash on cash: -0.87% Traditional cash on cash: -0.17% Airbnb Rental Income: $3278 Traditional Rental Income: $5453 Airbnb ROI: -0.87% Traditional ROI: -0.17%
37 Circuit Avenue #5 Oak Bluffs, MA Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shop...	1 beds \| 1 baths \| N/A	$935,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 0.2% Airbnb Rental Income: $3498 Traditional Rental Income: $1840 Airbnb ROI: 1.22% Traditional ROI: 0.2%
37 Circuit Avenue #4 Oak Bluffs, MA Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a s...	2 beds \| 1 baths \| N/A	$985,000	Airbnb cash on cash: 1.82% Traditional cash on cash: 0.39% Airbnb Rental Income: $4315 Traditional Rental Income: $2103 Airbnb ROI: 1.82% Traditional ROI: 0.39%
30 Franklin Avenue Oak Bluffs, MA Welcome to your dream home! This stunning new construction boasts a coastal feel throughou...	2 beds \| 3 baths \| 2,137 sq.ft.	$2,150,000	Airbnb cash on cash: 0.38% Traditional cash on cash: 0.41% Airbnb Rental Income: $4315 Traditional Rental Income: $3458 Airbnb ROI: 0.38% Traditional ROI: 0.41%
70 Carol Lane Oak Bluffs, MA Oak Bluffs location that is central to everything down Island. Situated on a 1/3 acre lot ...	2 beds \| 3 baths \| 1,500 sq.ft.	$1,200,000	Airbnb cash on cash: 1.54% Traditional cash on cash: 1.06% Airbnb Rental Income: $4315 Traditional Rental Income: $2872 Airbnb ROI: 1.54% Traditional ROI: 1.06%
30 Sengekontacket Road Oak Bluffs, MA Secluded island retreat nestled above the trees! Located in the desirable Sengekontacket A...	4 beds \| 3 baths \| 2,262 sq.ft.	$2,195,000	Airbnb cash on cash: -0.18% Traditional cash on cash: 0.4% Airbnb Rental Income: $3515 Traditional Rental Income: $3918 Airbnb ROI: -0.18% Traditional ROI: 0.4%
63 Bayes Hill Rd Oak Bluffs, MA Picture yourself in this beautifully designed custom home offering the ultimate in privacy...	4 beds \| 5 baths \| 5,165 sq.ft.	$3,150,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 0.81% Airbnb Rental Income: $3515 Traditional Rental Income: $6584 Airbnb ROI: -0.5% Traditional ROI: 0.81%
4 Dempster Park Oak Bluffs, MA East Chop -- This handsome, meticulously maintained 4-bedroom gambrel roof house, nestled ...	4 beds \| 3 baths \| 1,825 sq.ft.	$2,195,000	Airbnb cash on cash: 0.06% Traditional cash on cash: 0.49% Airbnb Rental Income: $3515 Traditional Rental Income: $3618 Airbnb ROI: 0.06% Traditional ROI: 0.49%
47 E Chop Drive unit: #5 #5 Oak Bluffs, MA East Chop Waterfront Luxury Cond -- This 1-BR, 1st floor, waterfront condominium, the ''Ca...	1 beds \| 1 baths \| 650 sq.ft.	$1,495,000	Airbnb cash on cash: 0.52% Traditional cash on cash: -0.06% Airbnb Rental Income: $3498 Traditional Rental Income: $1921 Airbnb ROI: 0.52% Traditional ROI: -0.06%
16 Atlantic Avenue Oak Bluffs, MA East Chop - Tucked away on a quiet lane just moments from the iconic East Chop Lighthouse ...	5 beds \| 3 baths \| 2,577 sq.ft.	$2,495,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.09% Airbnb Rental Income: $2334 Traditional Rental Income: $3605 Airbnb ROI: -0.71% Traditional ROI: 0.09%
37 Circuit Avenue unit: 4 #4 Oak Bluffs, MA Downtown Oak Bluffs Located right in the heart of town. Unit #4 A penthouse condo with a s...	2 beds \| 1 baths \| 990 sq.ft.	$985,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1.15% Airbnb Rental Income: $4315 Traditional Rental Income: $2319 Airbnb ROI: 2.33% Traditional ROI: 1.15%
37 Circuit Avenue unit: 5 #5 Oak Bluffs, MA Downtown Oak Bluffs centrally located in the heart of Oak Bluffs. Steps from ferries, shop...	1 beds \| 1 baths \| 797 sq.ft.	$935,000	Airbnb cash on cash: 1.75% Traditional cash on cash: 0.92% Airbnb Rental Income: $3498 Traditional Rental Income: $2008 Airbnb ROI: 1.75% Traditional ROI: 0.92%
47 E Chop Drive unit: #1 #1 Oak Bluffs, MA East Chop Water Front Luxury Condominium -- This 1-bedroom, 1st floor, waterfront condomin...	1 beds \| 1 baths \| 731 sq.ft.	$1,495,000	Airbnb cash on cash: 0.52% Traditional cash on cash: -0.03% Airbnb Rental Income: $3498 Traditional Rental Income: $1963 Airbnb ROI: 0.52% Traditional ROI: -0.03%
47 E Chop Drive unit: #2 #2 Oak Bluffs, MA East Chop Water Front Luxury Condominium -- This 1-bedroom, waterfront condominium, ''Cott...	1 beds \| 1 baths \| 736 sq.ft.	$1,495,000	Airbnb cash on cash: 0.52% Traditional cash on cash: -0.03% Airbnb Rental Income: $3498 Traditional Rental Income: $1963 Airbnb ROI: 0.52% Traditional ROI: -0.03%
47 E Chop Drive unit: #3 #3 Oak Bluffs, MA East Chop Water Front Luxury Condominiums -- This 2BR, waterfront condominium, the ''Highl...	2 beds \| 1 baths \| 802 sq.ft.	$1,995,000	Airbnb cash on cash: 0.42% Traditional cash on cash: -0.26% Airbnb Rental Income: $4315 Traditional Rental Income: $2155 Airbnb ROI: 0.42% Traditional ROI: -0.26%
47 E Chop Drive unit: #4 #4 Oak Bluffs, MA East Chop Harbor Front Luxury Condominiums -- This 2-bedroom, 2nd floor, waterfront condom...	2 beds \| 1 baths \| 879 sq.ft.	$1,995,000	Airbnb cash on cash: 0.42% Traditional cash on cash: -0.26% Airbnb Rental Income: $4315 Traditional Rental Income: $2155 Airbnb ROI: 0.42% Traditional ROI: -0.26%
4 Quail Run #7 Oak Bluffs, MA Amazing Turnkey End Unit with Kayak & EV Charger! Not to be missed! Island living made eas...	2 beds \| 2 baths \| 1,323 sq.ft.	$941,000	Airbnb cash on cash: 2.33% Traditional cash on cash: 1% Airbnb Rental Income: $4315 Traditional Rental Income: $2239 Airbnb ROI: 2.33% Traditional ROI: 1%
1 Onondaga Avenue Oak Bluffs, MA Charming Single Story Cottage on a Beautiful Oak Bluffs Lot - Perfect for Your Vineyard Re...	1 beds \| 1 baths \| 960 sq.ft.	$899,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 1.14% Airbnb Rental Income: $3498 Traditional Rental Income: $2261 Airbnb ROI: 1.69% Traditional ROI: 1.14%
32 Beach Road Oak Bluffs, MA Tucked along a main road in Oak Bluffs, this small yet cozy year-round cottage offers a ch...	3 beds \| 2 baths \| 836 sq.ft.	$1,050,000	Airbnb cash on cash: 1.05% Traditional cash on cash: 1.16% Airbnb Rental Income: $3278 Traditional Rental Income: $2649 Airbnb ROI: 1.05% Traditional ROI: 1.16%
35 Tower Ridge Road Oak Bluffs, MA Thoughtfully designed post-and-beam home that blends character with modern comfort and fle...	3 beds \| 4 baths \| 2,558 sq.ft.	$1,895,000	Airbnb cash on cash: 0.03% Traditional cash on cash: 1.11% Airbnb Rental Income: $3278 Traditional Rental Income: $4440 Airbnb ROI: 0.03% Traditional ROI: 1.11%
4 Canonicus Avenue Oak Bluffs, MA With a striking presence overlooking Nantucket Sound and just moments from the vibrant pul...	6 beds \| 4 baths \| 2,890 sq.ft.	$5,325,000	Airbnb cash on cash: -1.89% Traditional cash on cash: -1.28% Airbnb Rental Income: $2334 Traditional Rental Income: $4757 Airbnb ROI: -1.89% Traditional ROI: -1.28%
21 Norris Avenue Oak Bluffs, MA An Exciting Opportunity for First-Time Buyers or Island Investors. This long-time family h...	2 beds \| 1 baths \| 1,086 sq.ft.	$800,000	Airbnb cash on cash: 2.98% Traditional cash on cash: 1.44% Airbnb Rental Income: $4315 Traditional Rental Income: $2263 Airbnb ROI: 2.98% Traditional ROI: 1.44%
44 Iron Hill Road Oak Bluffs, MA Drive past bucolic horse pastures and Duartes Pond to a sweet neighborhood near the Alpaca...	3 beds \| 2 baths \| 1,496 sq.ft.	$1,350,000	Airbnb cash on cash: 0.64% Traditional cash on cash: 1% Airbnb Rental Income: $3278 Traditional Rental Income: $2992 Airbnb ROI: 0.64% Traditional ROI: 1%
11 Onondaga Avenue Oak Bluffs, MA Comfortable Island Home on a Quiet Dead-End Road in Oak Bluffs: Welcome to 11 Onondaga Ave...	3 beds \| 3 baths \| 1,624 sq.ft.	$1,250,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 1.51% Airbnb Rental Income: $3278 Traditional Rental Income: $3473 Airbnb ROI: 0.71% Traditional ROI: 1.51%
47 Winemack Avenue Oak Bluffs, MA Oak Bluffs -East Chop-Close to the ocean. Two cottages on one lot. Stay in one and rent th...	3 beds \| 2 baths \| N/A	$1,250,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 1.3% Airbnb Rental Income: $3278 Traditional Rental Income: $3277 Airbnb ROI: 0.67% Traditional ROI: 1.3%
46 Kennebec Avenue Oak Bluffs, MA Enjoy the convenience of being just steps away from the Public Beach, Steamship Authority,...	4 beds \| 2 baths \| 1,305 sq.ft.	$1,495,000	Airbnb cash on cash: 0.47% Traditional cash on cash: 0.8% Airbnb Rental Income: $3515 Traditional Rental Income: $3190 Airbnb ROI: 0.47% Traditional ROI: 0.8%
8 Paddock Road Oak Bluffs, MA Refined Vineyard Living in The Preserve - Set gracefully on a knoll with sweeping views of...	4 beds \| 6 baths \| 3,300 sq.ft.	$5,450,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.33% Airbnb Rental Income: $3515 Traditional Rental Income: $8269 Airbnb ROI: -0.77% Traditional ROI: 0.33%
5 Johns Way Oak Bluffs, MA Property is being offered via Real Estate Auction on Wednesday, September 17 at 12pm on-si...	3 beds \| 2 baths \| 1,365 sq.ft.	$950,600	Airbnb cash on cash: 1.74% Traditional cash on cash: 2.36% Airbnb Rental Income: $3278 Traditional Rental Income: $3091 Airbnb ROI: 1.74% Traditional ROI: 2.36%
16 Cottage Oak Bluffs, MA Just steps from the iconic Tabernacle and Trinity Park, this charming cottage is nestled i...	2 beds \| 1 baths \| 954 sq.ft.	$839,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 1.08% Airbnb Rental Income: $4315 Traditional Rental Income: $2089 Airbnb ROI: 2.76% Traditional ROI: 1.08%
6 Brewster Avenue Oak Bluffs, MA Enjoy sweeping ocean views from this beautifully updated East Chop Victorian, complete wit...	4 beds \| 3 baths \| 1,728 sq.ft.	$3,450,000	Airbnb cash on cash: -0.61% Traditional cash on cash: -0.31% Airbnb Rental Income: $3515 Traditional Rental Income: $3705 Airbnb ROI: -0.61% Traditional ROI: -0.31%
41 Trinity Park Oak Bluffs, MA Step back in time with this quintessential Martha's Vineyard Campground Cottage, nestled i...	4 beds \| 1 baths \| 1,154 sq.ft.	$795,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 2.06% Airbnb Rental Income: $3515 Traditional Rental Income: $2759 Airbnb ROI: 2.04% Traditional ROI: 2.06%
9 Grovedale Road Oak Bluffs, MA Welcome to a home full of character and charm in the heart of Oak Bluffs. This 3-bedroom, ...	3 beds \| 2 baths \| 1,637 sq.ft.	$1,150,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 1.42% Airbnb Rental Income: $3278 Traditional Rental Income: $3198 Airbnb ROI: 0.81% Traditional ROI: 1.42%

Your search for investment property begins and ends here

Boro Investment Property for Sale in Oak Bluffs, MA

1 Cottage Park

Oak Bluffs, MA

3 beds | 3 baths | 987 sq.ft.

$925,000

Airbnb cash on cash: 1.46%

Traditional cash on cash: 1.58%

Airbnb Rental Income: $3278

Traditional Rental Income: $2647

Airbnb ROI: 1.46%

Traditional ROI: 1.58%

8 School House Village

Oak Bluffs, MA

4 beds | 4 baths | 2,336 sq.ft.

$1,575,000

Airbnb cash on cash: 0.42%

Traditional cash on cash: 1.56%

Airbnb Rental Income: $3515

Traditional Rental Income: $4409

Airbnb ROI: 0.42%

Traditional ROI: 1.56%

47 Winemack Street

Oak Bluffs, MA

2 beds | 1 baths | 742 sq.ft.

$1,250,000

Airbnb cash on cash: 1.41%

Traditional cash on cash: 0.9%

Airbnb Rental Income: $4315

Traditional Rental Income: $2817

Airbnb ROI: 1.41%

Traditional ROI: 0.9%

4 High Meadow Lane

Oak Bluffs, MA

4 beds | 4 baths | 2,810 sq.ft.

$2,445,000

Airbnb cash on cash: -0.24%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $3515

Traditional Rental Income: $4171

Airbnb ROI: -0.24%

Traditional ROI: 0.39%

267 Barnes Road

Oak Bluffs, MA

3 beds | 6 baths | 4,046 sq.ft.

$4,500,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: -0.17%

Airbnb Rental Income: $3278

Traditional Rental Income: $5453

Airbnb ROI: -0.87%

Traditional ROI: -0.17%

37 Circuit Avenue #5

Oak Bluffs, MA

1 beds | 1 baths | N/A

$935,000

Airbnb cash on cash: 1.22%

Traditional cash on cash: 0.2%

Airbnb Rental Income: $3498

Traditional Rental Income: $1840

Airbnb ROI: 1.22%

Traditional ROI: 0.2%

37 Circuit Avenue #4

Oak Bluffs, MA

2 beds | 1 baths | N/A

$985,000

Airbnb cash on cash: 1.82%

Traditional cash on cash: 0.39%

Airbnb Rental Income: $4315

Traditional Rental Income: $2103

Airbnb ROI: 1.82%

Traditional ROI: 0.39%

30 Franklin Avenue

Oak Bluffs, MA

2 beds | 3 baths | 2,137 sq.ft.

$2,150,000

Airbnb cash on cash: 0.38%

Traditional cash on cash: 0.41%

Airbnb Rental Income: $4315

Traditional Rental Income: $3458

Airbnb ROI: 0.38%