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: -0.42%
|
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%
|
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: -0.18%
|
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%
|
2555 Youngs Avenue unit: 17D #17DSouthold, NYHere is a great opportunity to be part of the popular Founders Village Condo Assoc. This B... |
2 beds | 2 baths | 1,100 sq.ft. |
$550,000 |
Airbnb cash on cash: 0.75%
|
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%
|
Real Estate investment in Southold, NY
There are 36 properties for sale in the city of Southold . The median list price in Southold is $1,359,000 and the average price per square foot is $529. In December 2025, the average monthly cash on cash return in Southold is 2.00%. The average monthly rental income in Southold is $4,393.