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.

Investment Property for Sale in Southold, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
470 Goose Creek Lane 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: -1.17% Traditional cash on cash: 0.22% Airbnb Rental Income: $1415 Traditional Rental Income: $4088 Airbnb ROI: -1.17% Traditional ROI: 0.22%
700 Gin Lane Southold, NY Okay, I have to call you right now because I just walked into a house and I'm kind of... e...	4 beds \| 4 baths \| 2,627 sq.ft.	$1,850,000	Airbnb cash on cash: -1.44% Traditional cash on cash: 1.14% Airbnb Rental Income: $818 Traditional Rental Income: $4932 Airbnb ROI: -1.44% Traditional ROI: 1.14%
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: -1.53% Traditional cash on cash: 0.45% Airbnb Rental Income: $818 Traditional Rental Income: $7097 Airbnb ROI: -1.53% Traditional ROI: 0.45%
150 Deer Run Southold, NY Gorgeous estate-like Nantucket shingle home in the final stage of construction. Designed b...	5 beds \| 6 baths \| 5,285 sq.ft.	$3,825,000	Airbnb cash on cash: -1.83% Traditional cash on cash: 1.16% Airbnb Rental Income: $224 Traditional Rental Income: $10588 Airbnb ROI: -1.83% Traditional ROI: 1.16%
350 Brigantine Drive Southold, NY Welcome to 350 Brigantine Drive, a charming Southold retreat set in the peaceful waterfron...	3 beds \| 2 baths \| 975 sq.ft.	$624,900	Airbnb cash on cash: -0.87% Traditional cash on cash: 2.2% Airbnb Rental Income: $1418 Traditional Rental Income: $2781 Airbnb ROI: -0.87% Traditional ROI: 2.2%
3475 Oaklawn Avenue Southold, NY Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, ...	3 beds \| 2 baths \| 2,000 sq.ft.	$1,200,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.77% Airbnb Rental Income: $1415 Traditional Rental Income: $2875 Airbnb ROI: -0.92% Traditional ROI: 0.77%
600 Glenn Road Southold, NY Modern Luxury Waterfront Tree House - Nature Lovers' Paradise on West Creek! Discover this...	4 beds \| 6 baths \| 3,000 sq.ft.	$2,195,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 3.24% Airbnb Rental Income: $818 Traditional Rental Income: $8866 Airbnb ROI: -0.87% Traditional ROI: 3.24%
265 Arshamomaque Avenue Southold, NY This beautiful Newly Constructed Modern Craftsman/Cottage style home, tucked away down a c...	4 beds \| 4 baths \| 3,245 sq.ft.	$1,795,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 2.77% Airbnb Rental Income: $818 Traditional Rental Income: $6515 Airbnb ROI: -0.84% Traditional ROI: 2.77%
80 Deer Run Southold, NY Southold Stunner- New Construction This one's a North Fork knockout. Set at the end of a q...	4 beds \| 6 baths \| 7,341 sq.ft.	$3,295,000	Airbnb cash on cash: -1.91% Traditional cash on cash: 0.76% Airbnb Rental Income: $818 Traditional Rental Income: $8651 Airbnb ROI: -1.91% Traditional ROI: 0.76%
12250 Soundview Avenue Southold, NY North Fork Coastal Living With Sunset & Water Views Enjoy breathtaking sunsets and water v...	3 beds \| 4 baths \| 2,400 sq.ft.	$1,298,500	Airbnb cash on cash: -1% Traditional cash on cash: 2.43% Airbnb Rental Income: $1415 Traditional Rental Income: $5124 Airbnb ROI: -1% Traditional ROI: 2.43%
530 Sunset Way Southold, NY Wake up to breathtaking panoramic views of Peconic Bay from your own private waterfront re...	5 beds \| 2 baths \| 1,688 sq.ft.	$1,699,000	Airbnb cash on cash: -1.6% Traditional cash on cash: 0.97% Airbnb Rental Income: $224 Traditional Rental Income: $4053 Airbnb ROI: -1.6% Traditional ROI: 0.97%
450 Sterling Woods Lane Southold, NY Spacious Open Plan Home with So Much to Offer near Several Great Beaches. Open Livingroom,...	4 beds \| 3 baths \| 3,769 sq.ft.	$2,295,000	Airbnb cash on cash: -1.71% Traditional cash on cash: 0.43% Airbnb Rental Income: $818 Traditional Rental Income: $5060 Airbnb ROI: -1.71% Traditional ROI: 0.43%
295 Grange Road Southold, NY Southold Sanctuary There's a certain ease to life on the North Fork and knowing you are ne...	4 beds \| 4 baths \| 4,173 sq.ft.	$1,950,000	Airbnb cash on cash: -0.82% Traditional cash on cash: 2.43% Airbnb Rental Income: $818 Traditional Rental Income: $6382 Airbnb ROI: -0.82% Traditional ROI: 2.43%
2070 Cedar Drive Southold, NY 2070 Cedar Drive offers the kind of North Fork lifestyle buyers search for but rarely find...	2 beds \| 1 baths \| N/A	$989,000	Airbnb cash on cash: -0.94% Traditional cash on cash: 0.98% Airbnb Rental Income: $1285 Traditional Rental Income: $2654 Airbnb ROI: -0.94% Traditional ROI: 0.98%
630 Tarpon Drive Southold, NY Waterfront dream! This 3-bed, 2.5-bath home boasts safe deep-water docking on 50' wide can...	3 beds \| 3 baths \| 2,100 sq.ft.	$1,899,000	Airbnb cash on cash: -1.56% Traditional cash on cash: 0.46% Airbnb Rental Income: $1415 Traditional Rental Income: $4546 Airbnb ROI: -1.56% Traditional ROI: 0.46%
265 Hummel Avenue Southold, NY Welcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embod...	2 beds \| 1 baths \| 1,114 sq.ft.	$699,000	Airbnb cash on cash: -0.52% Traditional cash on cash: 3.23% Airbnb Rental Income: $1285 Traditional Rental Income: $3325 Airbnb ROI: -0.52% Traditional ROI: 3.23%
1815 Laurel Avenue Southold, NY Welcome to the Laurel Collection by Marrcon. New Luxury Construction located in the heart ...	4 beds \| 5 baths \| 4,327 sq.ft.	$2,795,000	Airbnb cash on cash: -1.03% Traditional cash on cash: 1.7% Airbnb Rental Income: $818 Traditional Rental Income: $7555 Airbnb ROI: -1.03% Traditional ROI: 1.7%
3500 Pine Neck Road Southold, NY Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold-an ...	3 beds \| 3 baths \| 2,000 sq.ft.	$1,999,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 2.42% Airbnb Rental Income: $1415 Traditional Rental Income: $7600 Airbnb ROI: -1.14% Traditional ROI: 2.42%
1000 Gin Lane Southold, NY Picture this: you've been walking through homes that are either way too much house... or f...	2 beds \| 1 baths \| 1,189 sq.ft.	$699,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 2.43% Airbnb Rental Income: $1285 Traditional Rental Income: $2933 Airbnb ROI: -0.71% Traditional ROI: 2.43%
5845 N Bayview Road Southold, NY Tucked away in a peaceful enclave of Southold, this classic Cape Cod offers a private esca...	3 beds \| 2 baths \| 1,989 sq.ft.	$1,050,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 6% Airbnb Rental Income: $1415 Traditional Rental Income: $7600 Airbnb ROI: -0.77% Traditional ROI: 6%
6625 Hortons Lane Southold, NY A beautiful and lovingly-maintained ranch with a front porch, set on a corner lot, offers ...	3 beds \| 2 baths \| 1,500 sq.ft.	$1,089,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 5.56% Airbnb Rental Income: $1415 Traditional Rental Income: $7600 Airbnb ROI: -0.96% Traditional ROI: 5.56%

Real Estate investment in Southold, NY

There are 21 properties for sale in the city of Southold . The median list price in Southold is $1,747,000 and the average price per square foot is $673. In April 2026, the average monthly cash on cash return in Southold is 2.00%. The average monthly rental income in Southold is $5,060.

Southold, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 21 investment properties available for sale in Southold.

In 2026, the best neighborhood to buy investment property is Southold.

The ROI for Long-Term is higher than the Short-Term in Southold with average rental income of $5,060.

Your search for investment property begins and ends here

Investment Property for Sale in Southold, NY

470 Goose Creek Lane

Southold, NY

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

$2,399,000

Airbnb cash on cash: -1.17%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $1415

Traditional Rental Income: $4088

Airbnb ROI: -1.17%

Traditional ROI: 0.22%

700 Gin Lane

Southold, NY

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

$1,850,000

Airbnb cash on cash: -1.44%

Traditional cash on cash: 1.14%

Airbnb Rental Income: $818

Traditional Rental Income: $4932

Airbnb ROI: -1.44%

Traditional ROI: 1.14%

465 Ripple Water Lane

Southold, NY

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

$3,598,999

Airbnb cash on cash: -1.53%

Traditional cash on cash: 0.45%

Airbnb Rental Income: $818

Traditional Rental Income: $7097

Airbnb ROI: -1.53%

Traditional ROI: 0.45%

150 Deer Run

Southold, NY

5 beds | 6 baths | 5,285 sq.ft.

$3,825,000

Airbnb cash on cash: -1.83%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $224

Traditional Rental Income: $10588

Airbnb ROI: -1.83%

Traditional ROI: 1.16%

350 Brigantine Drive

Southold, NY

3 beds | 2 baths | 975 sq.ft.

$624,900

Airbnb cash on cash: -0.87%

Traditional cash on cash: 2.2%

Airbnb Rental Income: $1418

Traditional Rental Income: $2781

Airbnb ROI: -0.87%

Traditional ROI: 2.2%

3475 Oaklawn Avenue

Southold, NY

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

$1,200,000

Airbnb cash on cash: -0.92%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $1415

Traditional Rental Income: $2875

Airbnb ROI: -0.92%

Traditional ROI: 0.77%

600 Glenn Road

Southold, NY

4 beds | 6 baths | 3,000 sq.ft.

$2,195,000

Airbnb cash on cash: -0.87%

Traditional cash on cash: 3.24%

Airbnb Rental Income: $818

Traditional Rental Income: $8866

Airbnb ROI: -0.87%

Traditional ROI: 3.24%

265 Arshamomaque Avenue

Southold, NY

4 beds | 4 baths | 3,245 sq.ft.

$1,795,000

Airbnb cash on cash: -0.84%

Traditional cash on cash: 2.77%

Airbnb Rental Income: $818

Traditional Rental Income: $6515

Airbnb ROI: -0.84%