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.

Single Family Homes for Sale in Southold, NY

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

Showing 37 Single Family Residential 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
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: -0.23% Traditional cash on cash: 3.04% Airbnb Rental Income: $1536 Traditional Rental Income: $3079 Airbnb ROI: -0.23% 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: $1018 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: $1018 Traditional Rental Income: $3967 Airbnb ROI: -1.2% Traditional ROI: 2.36%
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: -1.11% Traditional cash on cash: 1.81% Airbnb Rental Income: $1536 Traditional Rental Income: $7600 Airbnb ROI: -1.11% Traditional ROI: 1.81%
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% Traditional cash on cash: 1.72% Airbnb Rental Income: $1536 Traditional Rental Income: $4415 Airbnb ROI: -1% Traditional ROI: 1.72%
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: -1.48% Traditional cash on cash: 0.45% Airbnb Rental Income: $1018 Traditional Rental Income: $7097 Airbnb ROI: -1.48% 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: -1.56% Traditional cash on cash: 1.16% Airbnb Rental Income: $1358 Traditional Rental Income: $10588 Airbnb ROI: -1.56% Traditional ROI: 1.16%
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: -1.05% Traditional cash on cash: 0.77% Airbnb Rental Income: $1536 Traditional Rental Income: $3147 Airbnb ROI: -1.05% 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: $1018 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: $1018 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: 0.76% Traditional cash on cash: 4.56% Airbnb Rental Income: $1677 Traditional Rental Income: $2875 Airbnb ROI: 0.76% 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: $1018 Traditional Rental Income: $4302 Airbnb ROI: -1.34% Traditional ROI: 2.58%
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: -0.79% Traditional cash on cash: 3.24% Airbnb Rental Income: $1018 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: -0.66% Traditional cash on cash: 2.58% Airbnb Rental Income: $1536 Traditional Rental Income: $3802 Airbnb ROI: -0.66% Traditional ROI: 2.58%
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: -1.07% Traditional cash on cash: 0.96% Airbnb Rental Income: $1536 Traditional Rental Income: $4798 Airbnb ROI: -1.07% Traditional ROI: 0.96%
1635 Laurel Avenue Southold, NY TO BE COMPLETED FALL 2025. The Laurel Collection by Marrcon. New Luxury Construction locat...	4 beds \| 5 baths \| 3,960 sq.ft.	$2,600,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 2.13% Airbnb Rental Income: $1018 Traditional Rental Income: $7828 Airbnb ROI: -0.84% Traditional ROI: 2.13%
1465 Ackerly Pond Lane Southold, NY Nestled in the heart of Southoldâs coveted North Fork, 1465 Ackerly Pond Lane offers a r...	4 beds \| 3 baths \| 3,226 sq.ft.	$1,399,000	Airbnb cash on cash: -1.63% Traditional cash on cash: 1.52% Airbnb Rental Income: $1018 Traditional Rental Income: $4756 Airbnb ROI: -1.63% Traditional ROI: 1.52%
625 Glenn Road Southold, NY Move right in and start enjoying the North Fork lifestyle! This updated 3-bedroom, 2-bath ...	3 beds \| 2 baths \| 1,610 sq.ft.	$869,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 2.66% Airbnb Rental Income: $1536 Traditional Rental Income: $3725 Airbnb ROI: -0.59% Traditional ROI: 2.66%
480 N Bayview Road Extension Southold, NY Embrace refined living in this charming residence nestled in the heart of Southold. Enjoy ...	3 beds \| 3 baths \| 2,936 sq.ft.	$1,175,000	Airbnb cash on cash: -0.95% Traditional cash on cash: 2.05% Airbnb Rental Income: $1536 Traditional Rental Income: $4365 Airbnb ROI: -0.95% Traditional ROI: 2.05%
3700 Minnehaha Boulevard Southold, NY 3700 Minnehaha Blvd., Southold, a darling waterfront home nestled in Laughing Waters priva...	3 beds \| 2 baths \| 1,144 sq.ft.	$1,150,000	Airbnb cash on cash: -0.75% Traditional cash on cash: 1.29% Airbnb Rental Income: $1536 Traditional Rental Income: $3268 Airbnb ROI: -0.75% Traditional ROI: 1.29%
265 Arshamomaque Avenue Southold, NY This beautiful Newly Constructed Modern Craftsman/Cottage style home, tucked away down a p...	4 beds \| 4 baths \| 3,245 sq.ft.	$1,949,000	Airbnb cash on cash: -0.76% Traditional cash on cash: 2.48% Airbnb Rental Income: $1018 Traditional Rental Income: $6515 Airbnb ROI: -0.76% Traditional ROI: 2.48%
150 Goldin Lane Southold, NY Summer Cottage in Southold - Just steps from the Long Islands Sound. Experience quintessen...	3 beds \| 1 baths \| 900 sq.ft.	$789,000	Airbnb cash on cash: -0.3% Traditional cash on cash: 1.92% Airbnb Rental Income: $1536 Traditional Rental Income: $2726 Airbnb ROI: -0.3% Traditional ROI: 1.92%
790 N Sea Drive Southold, NY Quintessential North Fork Beach House!! Perched high above with breathtaking views of the ...	5 beds \| 4 baths \| 4,500 sq.ft.	$3,950,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 0.28% Airbnb Rental Income: $1358 Traditional Rental Income: $6557 Airbnb ROI: -1.26% Traditional ROI: 0.28%
205 Grange Road Southold, NY Location, Location, Location! Nestled in the heart of Southold, this home is in a beautif...	3 beds \| 1 baths \| 1,300 sq.ft.	$599,000	Airbnb cash on cash: -0.69% Traditional cash on cash: 2.93% Airbnb Rental Income: $1536 Traditional Rental Income: $3116 Airbnb ROI: -0.69% Traditional ROI: 2.93%
2120 Brigantine Drive Southold, NY Enjoy a beautifully updated home in the desirable Harbor Lights beach community. This home...	4 beds \| 4 baths \| 2,000 sq.ft.	$1,250,000	Airbnb cash on cash: -1.27% Traditional cash on cash: 2.65% Airbnb Rental Income: $1018 Traditional Rental Income: $5223 Airbnb ROI: -1.27% Traditional ROI: 2.65%
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: -1.86% Traditional cash on cash: 0.76% Airbnb Rental Income: $1018 Traditional Rental Income: $8651 Airbnb ROI: -1.86% Traditional ROI: 0.76%
1955 Laurel Avenue Southold, NY CONSTRUCTION COMPLETE! MOVE IN TODAY! Welcome to the Laurel Collection by Marrcon, a showc...	3 beds \| 4 baths \| 3,210 sq.ft.	$2,400,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 1.62% Airbnb Rental Income: $1536 Traditional Rental Income: $6095 Airbnb ROI: -0.63% Traditional ROI: 1.62%
440 Jernick Lane Southold, NY Delightful 3-bedroom, 2-bath ranch style home with attached 2 car garage offers the perfec...	3 beds \| 2 baths \| 1,600 sq.ft.	$869,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.51% Airbnb Rental Income: $1536 Traditional Rental Income: $3650 Airbnb ROI: -0.65% Traditional ROI: 2.51%
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.	$1,485,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 2% Airbnb Rental Income: $1536 Traditional Rental Income: $5124 Airbnb ROI: -0.92% Traditional ROI: 2%
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: -1.01% Traditional cash on cash: 0.97% Airbnb Rental Income: $1358 Traditional Rental Income: $4053 Airbnb ROI: -1.01% Traditional ROI: 0.97%
1020 Ruch Lane Southold, NY Welcome to Sunset Cottage! Perfectly situated on one of Southoldâs most desirable stree...	3 beds \| 3 baths \| 2,000 sq.ft.	$1,950,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 0.7% Airbnb Rental Income: $1536 Traditional Rental Income: $4624 Airbnb ROI: -1.25% Traditional ROI: 0.7%
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: -0.73% Traditional cash on cash: 2.43% Airbnb Rental Income: $1018 Traditional Rental Income: $6382 Airbnb ROI: -0.73% Traditional ROI: 2.43%
2070 Cedar Drive Southold, NY Spanning over an acre in desirable Goose Bay Estates, this exceptional property offers exp...	2 beds \| 1 baths \| N/A	$989,000	Airbnb cash on cash: -0.59% Traditional cash on cash: 1.71% Airbnb Rental Income: $1677 Traditional Rental Income: $3325 Airbnb ROI: -0.59% Traditional ROI: 1.71%
280 Clearview Avenue Southold, NY A charming four-bedroom, two-bath, one-level home with a touch of nostalgic appeal. This h...	4 beds \| 2 baths \| 1,600 sq.ft.	$839,000	Airbnb cash on cash: -1% Traditional cash on cash: 3.17% Airbnb Rental Income: $1018 Traditional Rental Income: $3922 Airbnb ROI: -1% Traditional ROI: 3.17%
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: -1.49% Traditional cash on cash: 0.47% Airbnb Rental Income: $1536 Traditional Rental Income: $4546 Airbnb ROI: -1.49% Traditional ROI: 0.47%
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.	$749,000	Airbnb cash on cash: -0.08% Traditional cash on cash: 2.95% Airbnb Rental Income: $1677 Traditional Rental Income: $3325 Airbnb ROI: -0.08% Traditional ROI: 2.95%
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: -0.96% Traditional cash on cash: 1.7% Airbnb Rental Income: $1018 Traditional Rental Income: $7555 Airbnb ROI: -0.96% Traditional ROI: 1.7%

Your search for investment property begins and ends here

Single Family Homes for Sale in Southold, NY

900 Cedar Drive

Southold, NY

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

$649,999

Airbnb cash on cash: -0.23%

Traditional cash on cash: 3.04%

Airbnb Rental Income: $1536

Traditional Rental Income: $3079

Airbnb ROI: -0.23%

Traditional ROI: 3.04%

5805 Main Bayview Road

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: $1018

Traditional Rental Income: $5375

Airbnb ROI: -1.33%

Traditional ROI: 0.36%

730 Pine Neck Road

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: $1018

Traditional Rental Income: $3967

Airbnb ROI: -1.2%

Traditional ROI: 2.36%

470 Goose Creek Lane

Southold, NY

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

$2,399,000

Airbnb cash on cash: -1.11%

Traditional cash on cash: 1.81%

Airbnb Rental Income: $1536

Traditional Rental Income: $7600

Airbnb ROI: -1.11%

Traditional ROI: 1.81%

3520 Old North Road

Southold, NY

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

$1,319,000

Airbnb cash on cash: -1%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $1536

Traditional Rental Income: $4415

Airbnb ROI: -1%

Traditional ROI: 1.72%

465 Ripple Water Lane

Southold, NY

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

$3,598,999

Airbnb cash on cash: -1.48%

Traditional cash on cash: 0.45%

Airbnb Rental Income: $1018

Traditional Rental Income: $7097

Airbnb ROI: -1.48%

Traditional ROI: 0.45%

150 Deer Run

Southold, NY

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

$3,825,000

Airbnb cash on cash: -1.56%

Traditional cash on cash: 1.16%

Airbnb Rental Income: $1358

Traditional Rental Income: $10588

Airbnb ROI: -1.56%

Traditional ROI: 1.16%

633 Pine Neck Road

Southold, NY

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

$1,215,000

Airbnb cash on cash: -1.05%

Traditional cash on cash: 0.77%

Airbnb Rental Income: $1536

Traditional Rental Income: $3147

Airbnb ROI: -1.05%