Real Estate Investment Properties for Sale in Southold, NY

Looking for investment property in Southold, NY with high ROI ?

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

Condos for Sale in Southold, NY

Search for Condo for Sale in Southold, New York. Browse all of Mashvisor’s Condo listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 1 Condo listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
52325 County Road 48 #31 Southold, NY 52325 County Road 48 #31, Southold, NY 11971 \| Condo/Coop	N/A beds \| 1 baths \| 250 sq.ft.	$239,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.34% Airbnb Rental Income: $2144 Traditional Rental Income: $1287 Airbnb ROI: 2.72% Traditional ROI: 1.34%
Other Investment Properties for Sale in Southold
650 The Esplanade Southold , NY Southold, North Fork - Private Bayfront Community Living Discover effortless, upscale livi...	3 beds \| 3 baths \| 2,300 sq.ft.	$1,249,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.72% Airbnb Rental Income: $3173 Traditional Rental Income: $4325 Airbnb ROI: 0.11% Traditional ROI: 1.72%
2015 Kenneys Rd Southold , NY Excellence Unsurpassed! Artisan Crafted Showpiece! No Holds Barred On Int/Ext Construct & ...	4 beds \| 3 baths \| 2,900 sq.ft.	$1,495,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 1.62% Airbnb Rental Income: $3027 Traditional Rental Income: $4713 Airbnb ROI: -0.09% Traditional ROI: 1.62%
1350 Hortons Ln Southold , NY Take Advantage Of A Wonderful Opportunity To Design Your Own Custom Built Escape On 2.24 A...	8 beds \| 7 baths \| 5,600 sq.ft.	$2,799,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 1.73% Airbnb Rental Income: $236 Traditional Rental Income: $7863 Airbnb ROI: -1.3% Traditional ROI: 1.73%
470 Goose Creek Ln Southold , NY Waterfront living designed for effortless coastal comfort. Ideally located just moments fr...	3 beds \| 2 baths \| 2,000 sq.ft.	$2,399,000	Airbnb cash on cash: -0.51% Traditional cash on cash: 0.22% Airbnb Rental Income: $3173 Traditional Rental Income: $4088 Airbnb ROI: -0.51% Traditional ROI: 0.22%
700 Gin Lane Southold , NY Southold Summer Vibes. Turnkey on the North Fork If you've been waiting for the right Nort...	4 beds \| 4 baths \| 2,627 sq.ft.	$1,799,995	Airbnb cash on cash: -0.31% Traditional cash on cash: 1.24% Airbnb Rental Income: $3027 Traditional Rental Income: $4932 Airbnb ROI: -0.31% Traditional ROI: 1.24%
430 Grove Rd Southold , NY Enter the Season and enjoy North Fork Serenity with the creek across the street to launch ...	3 beds \| 1 baths \| N/A	$699,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 3.06% Airbnb Rental Income: $3173 Traditional Rental Income: $3253 Airbnb ROI: 1.84% Traditional ROI: 3.06%
600 Highwood Road Southold , NY Unique opportunity in Southold to create your dream home on the North Fork. This A-frame-s...	2 beds \| 1 baths \| 1,954 sq.ft.	$999,999	Airbnb cash on cash: -0.45% Traditional cash on cash: 0.84% Airbnb Rental Income: $1881 Traditional Rental Income: $2575 Airbnb ROI: -0.45% Traditional ROI: 0.84%
2100 Glenn Rd Southold , NY Waterfront With Dock In The Heart Of Wine Country! Extremely Low Taxes & Gorgeous Views, T...	4 beds \| 2 baths \| 2,850 sq.ft.	$1,849,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.3% Airbnb Rental Income: $3027 Traditional Rental Income: $4807 Airbnb ROI: -0.14% Traditional ROI: 1.3%
465 Ripple Water Lane Southold , NY You know we have been looking at new homes for a while. This one is the first that felt li...	4 beds \| 6 baths \| 6,366 sq.ft.	$3,598,999	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.32% Airbnb Rental Income: $3027 Traditional Rental Income: $7097 Airbnb ROI: -1.11% Traditional ROI: 0.32%
25 Lighthouse Rd Southold , NY Tucked at the end of a long, private drive on one of Southold's historic streets, this cus...	4 beds \| 2 baths \| 3,800 sq.ft.	$1,899,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.56% Airbnb Rental Income: $3027 Traditional Rental Income: $5712 Airbnb ROI: -0.35% Traditional ROI: 1.56%
150 Baywater Ave Southold , NY Charming Antique Fixer Upper/Project Home Set on One Acre. Bring Your Contractor. This C...	3 beds \| 4 baths \| 2,100 sq.ft.	$850,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 7.98% Airbnb Rental Income: $3173 Traditional Rental Income: $7857 Airbnb ROI: 1.16% Traditional ROI: 7.98%
535 Bay Home Rd Southold , NY Southold - Canal Front - Unique opportunity to transform this 1970's home into your North ...	3 beds \| 4 baths \| 2,900 sq.ft.	$1,499,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.23% Airbnb Rental Income: $3173 Traditional Rental Income: $4223 Airbnb ROI: -0.03% Traditional ROI: 1.23%
150 Deer Run Southold , NY Gorgeous estate-like Nantucket shingle home in the final stage of construction. Designed b...	5 beds \| 4 baths \| 5,285 sq.ft.	$3,675,000	Airbnb cash on cash: -1.86% Traditional cash on cash: 1.25% Airbnb Rental Income: $236 Traditional Rental Income: $10588 Airbnb ROI: -1.86% Traditional ROI: 1.25%
3715 Hortons Ln Southold , NY Designer Modern Farmhouse set on over 3.35 Acres with farm and scenic views, Renovated 202...	4 beds \| 4 baths \| 2,200 sq.ft.	$1,599,999	Airbnb cash on cash: -0.26% Traditional cash on cash: 1.34% Airbnb Rental Income: $3027 Traditional Rental Income: $4712 Airbnb ROI: -0.26% Traditional ROI: 1.34%
1480 Old Wood Path Southold , NY Welcome to your own Peconic Bay beach & tennis paradise on 4 acres in Southold, a charming...	3 beds \| 4 baths \| 3,496 sq.ft.	$4,000,000	Airbnb cash on cash: -1.29% Traditional cash on cash: -0.27% Airbnb Rental Income: $3173 Traditional Rental Income: $6232 Airbnb ROI: -1.29% Traditional ROI: -0.27%

Your search for investment property begins and ends here

Condos for Sale in Southold, NY

52325 County Road 48 #31

Southold, NY

N/A beds | 1 baths | 250 sq.ft.

$239,000

Airbnb cash on cash: 2.72%

Traditional cash on cash: 1.34%

Airbnb Rental Income: $2144

Traditional Rental Income: $1287

Airbnb ROI: 2.72%

Traditional ROI: 1.34%

Other Investment Properties for Sale in Southold

Southold , NY

3 beds | 3 baths | 2,300 sq.ft.

$1,249,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $3173

Traditional Rental Income: $4325

Airbnb ROI: 0.11%

Traditional ROI: 1.72%

Southold , NY

4 beds | 3 baths | 2,900 sq.ft.

$1,495,000

Airbnb cash on cash: -0.09%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $3027

Traditional Rental Income: $4713

Airbnb ROI: -0.09%

Traditional ROI: 1.62%

Southold , NY

8 beds | 7 baths | 5,600 sq.ft.

$2,799,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $236

Traditional Rental Income: $7863

Airbnb ROI: -1.3%

Traditional ROI: 1.73%

Southold , NY

3 beds | 2 baths | 2,000 sq.ft.

$2,399,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $3173

Traditional Rental Income: $4088

Airbnb ROI: -0.51%

Traditional ROI: 0.22%

Southold , NY

4 beds | 4 baths | 2,627 sq.ft.

$1,799,995

Airbnb cash on cash: -0.31%

Traditional cash on cash: 1.24%

Airbnb Rental Income: $3027

Traditional Rental Income: $4932

Airbnb ROI: -0.31%

Traditional ROI: 1.24%

Southold , NY

3 beds | 1 baths | N/A

$699,000

Airbnb cash on cash: 1.84%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3173

Traditional Rental Income: $3253

Airbnb ROI: 1.84%

Traditional ROI: 3.06%

Southold , NY

2 beds | 1 baths | 1,954 sq.ft.

$999,999

Airbnb cash on cash: -0.45%

Traditional cash on cash: 0.84%

Airbnb Rental Income: $1881

Traditional Rental Income: $2575

Airbnb ROI: -0.45%

Traditional ROI: 0.84%

Southold , NY

4 beds | 2 baths | 2,850 sq.ft.

$1,849,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 1.3%