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.

Investment Property for Sale in Oak Bluffs, MA

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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%

Real Estate investment in Oak-bluffs, MA

There are 36 properties for sale in the city of Oak Bluffs . The median list price in Oak Bluffs is $1,422,500 and the average price per square foot is $835. In September 2025, the average monthly cash on cash return in Oak Bluffs is 1.00%. The average monthly rental income in Oak Bluffs is $2,932.

Oak-bluffs, MA Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 36 investment properties available for sale in Oak-bluffs.

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

The ROI for Short-Term is higher than the Long-Term in Oak-bluffs with average rental income of $3,515.

Your search for investment property begins and ends here

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%