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 2 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
2555 Youngs Avenue #11D Southold, NY Welcome to Founders Village in Southold. This quiet and quaint 55+ community is located in...	2 beds \| 2 baths \| 1,100 sq.ft.	$527,500	Airbnb cash on cash: -0.18% Traditional cash on cash: 3.06% Airbnb Rental Income: $1695 Traditional Rental Income: $2819 Airbnb ROI: -0.18% Traditional ROI: 3.06%
2555 Youngs Avenue unit: 17D #17D Southold, NY Here is a great opportunity to be part of the popular Founders Village Condo Assoc. This B...	2 beds \| 2 baths \| 1,100 sq.ft.	$550,000	Airbnb cash on cash: 0.75% Traditional cash on cash: 4.56% Airbnb Rental Income: $1695 Traditional Rental Income: $3182 Airbnb ROI: 0.75% Traditional ROI: 4.56%
Other Investment Properties for Sale in Southold
900 Cedar Drive Southold , NY Welcome to the North Fork. This pristine Ranch home features 3 Bedrooms 1 bath Updated Kit...	3 beds \| 1 baths \| 1,100 sq.ft.	$649,999	Airbnb cash on cash: -0.42% Traditional cash on cash: 3.04% Airbnb Rental Income: $1402 Traditional Rental Income: $3079 Airbnb ROI: -0.42% Traditional ROI: 3.04%
5805 Main Bayview Road Southold , NY Stunning Waterfront Retreat w/ Modern Luxury on 4+ Private Acres. Experience serene luxur...	4 beds \| 3 baths \| 3,253 sq.ft.	$2,998,000	Airbnb cash on cash: -1.33% Traditional cash on cash: 0.36% Airbnb Rental Income: $1019 Traditional Rental Income: $5375 Airbnb ROI: -1.33% Traditional ROI: 0.36%
730 Pine Neck Road Southold , NY **Open House cancelled*Completely renovated raised ranch just moments away from the qu...	4 beds \| 2 baths \| 2,200 sq.ft.	$998,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 2.36% Airbnb Rental Income: $1019 Traditional Rental Income: $3967 Airbnb ROI: -1.2% Traditional ROI: 2.36%
3520 Old North Road Southold , NY Cape Cod Style Retreat in the Heart of Southold This Southold gem delivers the perfect bl...	3 beds \| 3 baths \| 3,000 sq.ft.	$1,319,000	Airbnb cash on cash: -1.09% Traditional cash on cash: 1.72% Airbnb Rental Income: $1402 Traditional Rental Income: $4415 Airbnb ROI: -1.09% Traditional ROI: 1.72%
465 Ripple Water Lane Southold , NY COME and see this floor plan before it is gone!!!! Welcome to your bespoke farmhouse retre...	4 beds \| 6 baths \| 6,366 sq.ft.	$3,649,999	Airbnb cash on cash: -1.48% Traditional cash on cash: 0.43% Airbnb Rental Income: $1019 Traditional Rental Income: $7097 Airbnb ROI: -1.48% Traditional ROI: 0.43%
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.	$1,215,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 0.77% Airbnb Rental Income: $1402 Traditional Rental Income: $3147 Airbnb ROI: -1.14% Traditional ROI: 0.77%
1025 Long Creek Drive Southold , NY In the last month there have been lots of updates made to this exquisite waterfront home w...	4 beds \| 3 baths \| 2,700 sq.ft.	$1,450,000	Airbnb cash on cash: -1.47% Traditional cash on cash: 1.28% Airbnb Rental Income: $1019 Traditional Rental Income: $4371 Airbnb ROI: -1.47% Traditional ROI: 1.28%
10947 N Bayview Road Southold , NY Set on over two secluded acres within the coveted Shellfisher Preserve association near Pa...	4 beds \| 3 baths \| 2,600 sq.ft.	$2,995,000	Airbnb cash on cash: -1.49% Traditional cash on cash: -0.18% Airbnb Rental Income: $1019 Traditional Rental Income: $4323 Airbnb ROI: -1.49% Traditional ROI: -0.18%
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: 0.8% Traditional cash on cash: 4.56% Airbnb Rental Income: $1695 Traditional Rental Income: $2875 Airbnb ROI: 0.8% Traditional ROI: 4.56%
9875 Main Bayview Road Southold , NY Amazing opportunity to own a charming 1830s home with a detached accessory apartment built...	4 beds \| 3 baths \| 2,000 sq.ft.	$999,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 2.58% Airbnb Rental Income: $1019 Traditional Rental Income: $4302 Airbnb ROI: -1.34% Traditional ROI: 2.58%
600 Glenn Road Southold , NY Modern Luxury Waterfront Tree House - Nature Loversâ Paradise on West Creek! Discover th...	4 beds \| 6 baths \| 3,000 sq.ft.	$2,195,000	Airbnb cash on cash: -0.79% Traditional cash on cash: 3.24% Airbnb Rental Income: $1019 Traditional Rental Income: $8866 Airbnb ROI: -0.79% Traditional ROI: 3.24%
515 Corey Creek Lane Southold , NY Welcome to this beautifully maintained 3-bedroom, 2-bath ranch set on a pristine half-acre...	3 beds \| 2 baths \| 1,550 sq.ft.	$899,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 2.57% Airbnb Rental Income: $1402 Traditional Rental Income: $3802 Airbnb ROI: -0.81% Traditional ROI: 2.57%
2300 Glenn Road Southold , NY Located in one of Southoldâs most coveted locations, this waterfront oasis offers peace,...	3 beds \| 3 baths \| 2,500 sq.ft.	$1,975,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.96% Airbnb Rental Income: $1402 Traditional Rental Income: $4798 Airbnb ROI: -1.13% Traditional ROI: 0.96%
285 Blue Marlin Drive Southold , NY BONUS: Upon request builder will include a custom built 12x12 pool shed with the same mate...	4 beds \| 5 baths \| 2,842 sq.ft.	$2,499,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 1.79% Airbnb Rental Income: $1019 Traditional Rental Income: $6698 Airbnb ROI: -0.82% Traditional ROI: 1.79%

Your search for investment property begins and ends here

Condos for Sale in Southold, NY

2555 Youngs Avenue #11D

Southold, NY

2 beds | 2 baths | 1,100 sq.ft.

$527,500

Airbnb cash on cash: -0.18%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $1695

Traditional Rental Income: $2819

Airbnb ROI: -0.18%

Traditional ROI: 3.06%

2555 Youngs Avenue unit: 17D #17D

Southold, NY

2 beds | 2 baths | 1,100 sq.ft.

$550,000

Airbnb cash on cash: 0.75%

Traditional cash on cash: 4.56%

Airbnb Rental Income: $1695

Traditional Rental Income: $3182

Airbnb ROI: 0.75%

Traditional ROI: 4.56%

Other Investment Properties for Sale in Southold

Southold , NY

3 beds | 1 baths | 1,100 sq.ft.

$649,999

Airbnb cash on cash: -0.42%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $1402

Traditional Rental Income: $3079

Airbnb ROI: -0.42%

Traditional ROI: 3.04%

Southold , NY

4 beds | 3 baths | 3,253 sq.ft.

$2,998,000

Airbnb cash on cash: -1.33%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $1019

Traditional Rental Income: $5375

Airbnb ROI: -1.33%

Traditional ROI: 0.36%

Southold , NY

4 beds | 2 baths | 2,200 sq.ft.

$998,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 2.36%

Airbnb Rental Income: $1019

Traditional Rental Income: $3967

Airbnb ROI: -1.2%

Traditional ROI: 2.36%

Southold , NY

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

$1,319,000

Airbnb cash on cash: -1.09%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $1402

Traditional Rental Income: $4415

Airbnb ROI: -1.09%

Traditional ROI: 1.72%

Southold , NY

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

$3,649,999

Airbnb cash on cash: -1.48%

Traditional cash on cash: 0.43%

Airbnb Rental Income: $1019

Traditional Rental Income: $7097

Airbnb ROI: -1.48%

Traditional ROI: 0.43%

Southold , NY

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

$1,215,000

Airbnb cash on cash: -1.14%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $1402

Traditional Rental Income: $3147

Airbnb ROI: -1.14%

Traditional ROI: 0.77%

Southold , NY

4 beds | 3 baths | 2,700 sq.ft.

$1,450,000

Airbnb cash on cash: -1.47%