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 34 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: -0.42%
|
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: -1.33%
|
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: -1.2%
|
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: -1.09%
|
465 Ripple Water LaneSouthold, NYCOME and see this floor plan before it is gone!!!! Welcome to your bespoke farmhouse retre... |
4 beds | 6 baths | 6,366 sq.ft. |
$3,649,999 |
Airbnb cash on cash: -1.48%
|
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: -1.14%
|
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: -1.47%
|
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: -1.49%
|
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: 0.8%
|
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: -1.34%
|
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: -0.79%
|
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. |
$899,000 |
Airbnb cash on cash: -0.81%
|
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: -1.13%
|
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: -0.82%
|
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: -0.84%
|
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: -1.63%
|
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: -0.73%
|
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: -1.05%
|
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: -0.85%
|
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. |
$1,949,000 |
Airbnb cash on cash: -0.76%
|
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: -0.45%
|
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: -1.24%
|
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: -0.89%
|
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: -1.25%
|
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: -1.87%
|
1955 Laurel AvenueSouthold, NYCONSTRUCTION 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: -0.68%
|
440 Jernick LaneSouthold, NYDelightful 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: -0.79%
|
12250 Soundview AvenueSouthold, NYNorth 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: -1%
|
530 Sunset WaySouthold, NYWake 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: -0.99%
|
1020 Ruch LaneSouthold, NYWelcome 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: -1.31%
|
450 Sterling Woods LaneSouthold, NYSpacious 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: -1.61%
|
295 Grange RoadSouthold, NYSouthold 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%
|
2070 Cedar DriveSouthold, NYSpanning 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: -0.57%
|
280 Clearview AvenueSouthold, NYA 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: -0.79%
|