Airbnb Properties for Sale in Southold, NY

Looking for a vacation rental investment in Southold, NY with high ROI ?

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

Airbnb For Sale in Southold, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
700 Gin Lane Southold, NY Welcome to your dream beach home nestled in a serene beach community on the North Fork! Th...	4 beds \| 4 baths \| N/A	$2,474,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 0.64% Airbnb Rental Income: $12703 Traditional Rental Income: $4932 Airbnb ROI: 3.02% Traditional ROI: 0.64%
465 Tarpon Drive Southold, NY Introducing 465 Tarpon Drive, a stunning property in the coveted Southold Shores Bayfront ...	3 beds \| 3 baths \| 1,572 sq.ft.	$899,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 2.25% Airbnb Rental Income: $5215 Traditional Rental Income: $3589 Airbnb ROI: 2.93% Traditional ROI: 2.25%
465 Ripple Water Lane Southold, NY Welcome to your bespoke farmhouse retreat nestled in the serene beauty of the North Fork o...	4 beds \| 6 baths \| 6,366 sq.ft.	$3,799,999	Airbnb cash on cash: 1.31% Traditional cash on cash: 0.37% Airbnb Rental Income: $12703 Traditional Rental Income: $7097 Airbnb ROI: 1.31% Traditional ROI: 0.37%
1475 Oaklawn Avenue Southold, NY Welcome to this beautiful, fully renovated home, where classic charm meets modern luxury. ...	4 beds \| 3 baths \| N/A	$999,000	Airbnb cash on cash: 9.32% Traditional cash on cash: 2.96% Airbnb Rental Income: $12703 Traditional Rental Income: $4483 Airbnb ROI: 9.32% Traditional ROI: 2.96%
630 Calves Neck Road Southold, NY Welcome to 630 Calves Neck Road! This new construction North Fork diamond boasts 4,400 squ...	4 beds \| 6 baths \| 4,400 sq.ft.	$3,149,000	Airbnb cash on cash: 2.26% Traditional cash on cash: 1.57% Airbnb Rental Income: $12703 Traditional Rental Income: $8373 Airbnb ROI: 2.26% Traditional ROI: 1.57%
633 Pine Neck Road Southold, NY A must see secluded water front Compound. Rarely do you find two houses on a one acre lot....	3 beds \| 2 baths \| 1,068 sq.ft.	$1,349,000	Airbnb cash on cash: 1.4% Traditional cash on cash: 0.6% Airbnb Rental Income: $5215 Traditional Rental Income: $3147 Airbnb ROI: 1.4% Traditional ROI: 0.6%
6900 Main Bayview Road Southold, NY	2 beds \| 1 baths \| N/A	$629,000	Airbnb cash on cash: 5.15% Traditional cash on cash: 2.21% Airbnb Rental Income: $5189 Traditional Rental Income: $2408 Airbnb ROI: 5.15% Traditional ROI: 2.21%
700 Bayview Avenue Southold, NY Welcome to 700 Bayview Ave, in Southold. This charming retreat is across the street from H...	3 beds \| 2 baths \| 1,600 sq.ft.	$685,000	Airbnb cash on cash: 4.5% Traditional cash on cash: 3.07% Airbnb Rental Income: $5215 Traditional Rental Income: $3242 Airbnb ROI: 4.5% Traditional ROI: 3.07%
1500 Hortons Lane Southold, NY Welcome Home to this sunny 3-bedroom, 2.5-bath Equestrian home built in 2001set on a spraw...	3 beds \| 3 baths \| 1,900 sq.ft.	$1,250,000	Airbnb cash on cash: 1.64% Traditional cash on cash: 1.28% Airbnb Rental Income: $5215 Traditional Rental Income: $3735 Airbnb ROI: 1.64% Traditional ROI: 1.28%
500 Summer Lane Southold, NY Property with vast potential in Prime location, close to Southold beaches, vineyards and s...	2 beds \| 2 baths \| 880 sq.ft.	$469,000	Airbnb cash on cash: 7.43% Traditional cash on cash: 4.56% Airbnb Rental Income: $5189 Traditional Rental Income: $2875 Airbnb ROI: 7.43% Traditional ROI: 4.56%
155 Seawood Drive Southold, NY Don't miss this newly listed beach cottage in the neighborhood of Seawood Acres ready for ...	2 beds \| 1 baths \| N/A	$659,000	Airbnb cash on cash: 4.77% Traditional cash on cash: 2.7% Airbnb Rental Income: $5189 Traditional Rental Income: $2866 Airbnb ROI: 4.77% Traditional ROI: 2.7%
2505 Wells Avenue Southold, NY Charming, Sleek, and Sexy waterfront cape-style home with exceptional water views located ...	3 beds \| 2 baths \| 2,000 sq.ft.	$1,645,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 0.84% Airbnb Rental Income: $5215 Traditional Rental Income: $3758 Airbnb ROI: 1.1% Traditional ROI: 0.84%
5535 Old North Road Southold, NY A classic North Fork farmhouse nestled in the heart of wine country, a winery adjacent to ...	3 beds \| 1 baths \| 1,760 sq.ft.	$835,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 1.58% Airbnb Rental Income: $5215 Traditional Rental Income: $2765 Airbnb ROI: 3.37% Traditional ROI: 1.58%
155 Glover Street Southold, NY Thie beautiful, updated ranch home is set upon a park-like setting with vineyard views. V...	2 beds \| 2 baths \| 1,300 sq.ft.	$675,000	Airbnb cash on cash: 4.47% Traditional cash on cash: 2.09% Airbnb Rental Income: $5189 Traditional Rental Income: $2636 Airbnb ROI: 4.47% Traditional ROI: 2.09%
6005 Hortons Lane Southold, NY This prime Southold property offers a fantastic opportunity for subdivision and developmen...	4 beds \| 2 baths \| N/A	$2,200,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 0.27% Airbnb Rental Income: $12703 Traditional Rental Income: $3690 Airbnb ROI: 3.55% Traditional ROI: 0.27%
500 Arshamomaque Avenue Southold, NY This stunning new construction modern farmhouses is located in the quiet community of Bei...	4 beds \| 5 baths \| 2,334 sq.ft.	$1,650,000	Airbnb cash on cash: 5.09% Traditional cash on cash: 1.82% Airbnb Rental Income: $12703 Traditional Rental Income: $5395 Airbnb ROI: 5.09% Traditional ROI: 1.82%
200 Critten Southold, NY This beautifully maintained ranch features 3 spacious bedrooms, 2 fully renovated bathroom...	3 beds \| 2 baths \| 1,560 sq.ft.	$849,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 2.83% Airbnb Rental Income: $5215 Traditional Rental Income: $3713 Airbnb ROI: 3.39% Traditional ROI: 2.83%
65 Lake Drive Southold, NY Adorable Beach Bungalow Getaway!!! Kenney's Beach practically at your doorstep. There's r...	5 beds \| 2 baths \| 1,500 sq.ft.	$1,200,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 1.62% Airbnb Rental Income: $5409 Traditional Rental Income: $3698 Airbnb ROI: 2.18% Traditional ROI: 1.62%
2555 Youngs #5E Southold, NY 2BR 2Bath corner unit in Founders Village, Southold's premier 55+ active community. Featur...	2 beds \| 2 baths \| 1,200 sq.ft.	$590,000	Airbnb cash on cash: 5.06% Traditional cash on cash: 2.88% Airbnb Rental Income: $5189 Traditional Rental Income: $2932 Airbnb ROI: 5.06% Traditional ROI: 2.88%
2555 Youngs #7D Southold, NY 2BR 2Bath condo in Founders Village, Southolds premier 55+ active community. Unit features...	2 beds \| 2 baths \| 1,100 sq.ft.	$575,000	Airbnb cash on cash: 5.18% Traditional cash on cash: 2.77% Airbnb Rental Income: $5189 Traditional Rental Income: $2844 Airbnb ROI: 5.18% Traditional ROI: 2.77%

Vacation Rentals in Southold

There are 20 vacation rental properties available for sale in the city of Southold . The median list price of Airbnb properties available for sale in Southold is $999,000 and the average price per square foot is $441. The cash on cash return on vacation rentals in Southold is 3.00%. The average monthly short term rental income in Southold is $5,215.

Southold, NY Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 20 Airbnb properties available for sale in Southold.

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

In January 2025, the average Airbnb occupancy rate in Southold is 42%.

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

Your search for investment property begins and ends here

Airbnb For Sale in Southold, NY

700 Gin Lane

Southold, NY

4 beds | 4 baths | N/A

$2,474,000

Airbnb cash on cash: 3.02%

Traditional cash on cash: 0.64%

Airbnb Rental Income: $12703

Traditional Rental Income: $4932

Airbnb ROI: 3.02%

Traditional ROI: 0.64%

465 Tarpon Drive

Southold, NY

3 beds | 3 baths | 1,572 sq.ft.

$899,000

Airbnb cash on cash: 2.93%

Traditional cash on cash: 2.25%

Airbnb Rental Income: $5215

Traditional Rental Income: $3589

Airbnb ROI: 2.93%

Traditional ROI: 2.25%

465 Ripple Water Lane

Southold, NY

4 beds | 6 baths | 6,366 sq.ft.

$3,799,999

Airbnb cash on cash: 1.31%

Traditional cash on cash: 0.37%

Airbnb Rental Income: $12703

Traditional Rental Income: $7097

Airbnb ROI: 1.31%

Traditional ROI: 0.37%

1475 Oaklawn Avenue

Southold, NY

4 beds | 3 baths | N/A

$999,000

Airbnb cash on cash: 9.32%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $12703

Traditional Rental Income: $4483

Airbnb ROI: 9.32%

Traditional ROI: 2.96%

630 Calves Neck Road

Southold, NY

4 beds | 6 baths | 4,400 sq.ft.

$3,149,000

Airbnb cash on cash: 2.26%

Traditional cash on cash: 1.57%

Airbnb Rental Income: $12703

Traditional Rental Income: $8373

Airbnb ROI: 2.26%

Traditional ROI: 1.57%

633 Pine Neck Road

Southold, NY

3 beds | 2 baths | 1,068 sq.ft.

$1,349,000

Airbnb cash on cash: 1.4%

Traditional cash on cash: 0.6%

Airbnb Rental Income: $5215

Traditional Rental Income: $3147

Airbnb ROI: 1.4%

Traditional ROI: 0.6%

6900 Main Bayview Road

Southold, NY

2 beds | 1 baths | N/A

$629,000

Airbnb cash on cash: 5.15%

Traditional cash on cash: 2.21%

Airbnb Rental Income: $5189

Traditional Rental Income: $2408

Airbnb ROI: 5.15%

Traditional ROI: 2.21%

700 Bayview Avenue

Southold, NY

3 beds | 2 baths | 1,600 sq.ft.

$685,000

Airbnb cash on cash: 4.5%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $5215

Traditional Rental Income: $3242

Airbnb ROI: 4.5%