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: 0.08%
|
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: -1.19%
|
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: -0.78%
|
3520 Old North RoadSouthold, NYCape 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: -0.84%
|
600 ParkwaySouthold, NYWelcome to the charming and desirable Southwoods Community, located in the heart of the No... |
3 beds | 1 baths | 1,600 sq.ft. |
$889,000 |
Airbnb cash on cash: -0.41%
|
465 Ripple Water LaneSouthold, NYCOME and see this floor plan before it is gone!!!! Welcome to your bespoke farmhouse retr... |
4 beds | 6 baths | 6,366 sq.ft. |
$3,649,999 |
Airbnb cash on cash: -1.36%
|
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: -0.88%
|
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: -1.19%
|
10947 N Bayview RoadSouthold, NYSet 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: -1.36%
|
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: 1.39%
|
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: -0.38%
|
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: 0.35%
|
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: -0.93%
|
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: 0.35%
|
600 Glenn RoadSouthold, NYModern 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: -0.6%
|
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: 0.23%
|
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: -0.5%
|
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: 0.45%
|
2300 Glenn RoadSouthold, NYLocated 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: -0.96%
|
285 Blue Marlin DriveSouthold, NYBONUS: 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: -0.65%
|
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: -0.68%
|
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: -1.33%
|
625 Glenn RoadSouthold, NYMove 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: -0.36%
|
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: -0.77%
|
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: -0.41%
|
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: -0.57%
|
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. |
$1,995,000 |
Airbnb cash on cash: -0.56%
|
150 Goldin LaneSouthold, NYSummer Cottage in Southold â Just steps from the Long Islands Sound. Experience quintess... |
3 beds | 1 baths | 900 sq.ft. |
$789,000 |
Airbnb cash on cash: -0.04%
|
790 N Sea DriveSouthold, NYQuintessential 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: -1.13%
|
3470 N Bayview RoadSouthold, NYWelcome to luxury on the North Fork. This quality built home is located only 3 properties... |
5 beds | 5 baths | 3,800 sq.ft. |
$2,200,000 |
Airbnb cash on cash: -1.08%
|
205 Grange RoadSouthold, NYLocation, 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: -0.35%
|
2120 Brigantine DriveSouthold, NYEnjoy 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: -0.92%
|
80 Deer RunSouthold, NYSouthold 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: -1.75%
|
550 Pine Neck RoadSouthold, NYPerfect Weekend Escape Or Cozy Year-Round Haven! This Adorable 2 Bedroom, 1 Bath Ranch Sty... |
2 beds | 1 baths | 1,200 sq.ft. |
$599,000 |
Airbnb cash on cash: 0.57%
|
1955 Laurel AvenueSouthold, NYMOVE IN OCTOBER 2025!! Welcome to the Laurel Collection by Marrcon, a showcase of modern ... |
3 beds | 4 baths | 3,210 sq.ft. |
$2,400,000 |
Airbnb cash on cash: -0.55%
|
Real Estate investment in Southold, NY
There are 35 properties for sale in the city of Southold . The median list price in Southold is $1,175,000 and the average price per square foot is $489. In October 2025, the average monthly cash on cash return in Southold is 2.00%. The average monthly rental income in Southold is $4,302.