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 30 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
900 Cedar DriveSouthold, NYWelcome 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: 5.34%
|
5805 Main Bayview RoadSouthold, NYStunning 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: 0.57%
|
730 Pine Neck RoadSouthold, 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: 4.5%
|
700 Gin LaneSouthold, NYStep inside and wowâthis home lives much larger than it looks from the outside! With a f... |
4 beds | 4 baths | 2,627 sq.ft. |
$1,995,000 |
Airbnb cash on cash: 1.55%
|
633 Pine Neck RoadSouthold, NYA 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: 1.94%
|
1025 Long Creek DriveSouthold, NYIn 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: 2.46%
|
10947 N Bayview RoadSouthold, NYCompound with House, Barn and 70' Deep Water Dock in Private Marina. Water views from the ... |
4 beds | 3 baths | N/A |
$3,275,000 |
Airbnb cash on cash: 0.28%
|
1500 Hortons LaneSouthold, NYWelcome 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. |
$1,199,000 |
Airbnb cash on cash: 2.04%
|
500 Summer LaneSouthold, NYProperty 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: 0.98%
|
1750 Hobart RoadSouthold, NYWelcome to a stunning, one-of-a-kind waterfront home in the highly sought-after hamlet of ... |
5 beds | 5 baths | 4,627 sq.ft. |
$9,275,000 |
Airbnb cash on cash: N/A
|
65 Lake DriveSouthold, NYThe Perfect Beach Bungalow Getaway! An Idyllic Location, With Kenney's Beach Practically A... |
5 beds | 2 baths | 1,500 sq.ft. |
$999,999 |
Airbnb cash on cash: N/A
|
150 Hobart RoadSouthold, NYExperience the ultimate North Fork retreat in Southold-this stunning, turnkey cottage is a... |
2 beds | 2 baths | 1,300 sq.ft. |
$849,000 |
Airbnb cash on cash: -0.02%
|
9875 Main Bayview RoadSouthold, NYAmazing 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: 4.35%
|
600 Glenn RoadSouthold, NYWelcome to 600 Glenn Rd, Southold, NY, a contemporary masterpiece built in 2025, situated ... |
4 beds | 6 baths | 3,000 sq.ft. |
$2,395,000 |
Airbnb cash on cash: 1.57%
|
570 N North Bayview RoadSouthold, NYPerfect opportunity for 1st time buyers, downsizers, or investors! This original-style 3-b... |
3 beds | 1 baths | 1,200 sq.ft. |
$779,000 |
Airbnb cash on cash: 4.62%
|
515 Corey Creek LaneSouthold, NYWelcome to this beautifully maintained 3-bedroom, 2-bath ranch set on a pristine half-acre... |
3 beds | 2 baths | 1,550 sq.ft. |
$999,000 |
Airbnb cash on cash: 2.93%
|
560 Clark RoadSouthold, NYDiscover this beautifully maintained 2-bedroom, 1-bathroom cottage nestled on a tranquil r... |
2 beds | 1 baths | 796 sq.ft. |
$699,900 |
Airbnb cash on cash: 0.18%
|
2215 Laurel AvenueSouthold, NYWelcome to the Laurel Collection by Marrcon, a showcase of modern luxury in the heart of S... |
3 beds | 4 baths | 3,210 sq.ft. |
$2,295,000 |
Airbnb cash on cash: -0.66%
|
265 Custer AvenueSouthold, NYBeautiful solid built ranch home located on a quiet street with a park like half acre of p... |
3 beds | 2 baths | 1,800 sq.ft. |
$850,000 |
Airbnb cash on cash: 3.67%
|
2300 Glenn RoadSouthold, NYLocated in one of Southoldâs most coveted locations, this waterfront oasis offers peace,... |
3 beds | 3 baths | 2,500 sq.ft. |
$2,180,000 |
Airbnb cash on cash: 0.61%
|
285 Blue Marlin DriveSouthold, NYEntire house completed and beautifully landscaped!!!!With incredible water views and acces... |
4 beds | 5 baths | 2,842 sq.ft. |
$2,649,000 |
Airbnb cash on cash: 1.33%
|
1635 Laurel AvenueSouthold, NYTO 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: 1.36%
|
50 Summit DriveSouthold, NYWelcome to easy living in this charming three-bedroom ranch, perfectly set up for comforta... |
3 beds | 3 baths | 1,651 sq.ft. |
$799,999 |
Airbnb cash on cash: 3.78%
|
1465 Ackerly Pond LaneSouthold, NYNestled 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: 2.44%
|
625 Glenn RoadSouthold, NYSituated in an area rich in the founding history of Southold Town, what likely began as wo... |
3 beds | 2 baths | 1,610 sq.ft. |
$888,000 |
Airbnb cash on cash: 3.48%
|
4710 Old North RoadSouthold, NYWelcome to 4710 Old North Rd, a private Southold retreat. This beautifully maintained 2,40... |
4 beds | 3 baths | 2,400 sq.ft. |
$1,249,999 |
Airbnb cash on cash: 3.31%
|
480 N Bayview Road ExtensionSouthold, NYEmbrace 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: 2.15%
|
720 Mechanic StreetSouthold, NYTucked away in the heart of Southold, this adorable 3-bedroom, 2.5-bath ranch offers a rar... |
3 beds | 3 baths | 1,317 sq.ft. |
$950,000 |
Airbnb cash on cash: 3.19%
|
3700 Minnehaha BoulevardSouthold, NY3700 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: 2.62%
|
265 Arshamomaque AvenueSouthold, NYThis beautiful Newly Constructed Modern Craftsman/Cottage style home, tucked away down a p... |
4 beds | 4 baths | 3,245 sq.ft. |
$2,095,000 |
Airbnb cash on cash: 1.95%
|