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
| 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
|
2555 Youngs #7DSouthold, NY2BR 2Bath condo in Founders Village, Southolds premier 55+ active community. Unit features... |
2 beds | 2 baths | 1,100 sq.ft. |
$529,000 |
Airbnb cash on cash: -0.01%
|
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%
|
2555 Youngs Avenue #11DSouthold, NYWelcome 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: -0.01%
|
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%
|
Real Estate investment in Southold, NY
There are 32 properties for sale in the city of Southold . The median list price in Southold is $1,162,500 and the average price per square foot is $548. In September 2025, the average monthly cash on cash return in Southold is 2.00%. The average monthly rental income in Southold is $4,028.