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 |
|---|---|---|---|
650 The EsplanadeSouthold, NYSouthold, North Fork - Private Bayfront Community Living Discover effortless, upscale livi... |
3 beds | 3 baths | 2,300 sq.ft. |
$1,249,000 |
Airbnb cash on cash: -0.39%
|
470 Goose Creek LaneSouthold, NYWaterfront living designed for effortless coastal comfort. Ideally located just moments fr... |
3 beds | 2 baths | 2,000 sq.ft. |
$2,399,000 |
Airbnb cash on cash: -0.78%
|
700 Gin LaneSouthold, NYSouthold Summer Vibes. Turnkey on the North Fork If you've been waiting for the right Nort... |
4 beds | 4 baths | 2,627 sq.ft. |
$1,799,995 |
Airbnb cash on cash: -0.37%
|
430 Grove RoadSouthold, NYEnter the Season and enjoy North Fork Serenity with the creek across the street to launch ... |
3 beds | 1 baths | N/A |
$699,000 |
Airbnb cash on cash: 0.94%
|
600 Highwood RoadSouthold, NYUnique opportunity in Southold to create your dream home on the North Fork. This A-frame-s... |
2 beds | 1 baths | 1,954 sq.ft. |
$999,999 |
Airbnb cash on cash: -0.78%
|
465 Ripple Water LaneSouthold, NYYou know we have been looking at new homes for a while. This one is the first that felt li... |
4 beds | 6 baths | 6,366 sq.ft. |
$3,598,999 |
Airbnb cash on cash: -1.14%
|
25 Lighthouse RoadSouthold, NYTucked at the end of a long, private drive on one of Southold's historic streets, this cus... |
4 beds | 3 baths | 3,800 sq.ft. |
$1,899,000 |
Airbnb cash on cash: -0.41%
|
150 Deer RunSouthold, NYGorgeous estate-like Nantucket shingle home in the final stage of construction. Designed b... |
5 beds | 6 baths | 5,285 sq.ft. |
$3,695,000 |
Airbnb cash on cash: -1.85%
|
1665 Glenn RoadSouthold, NYNewly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 G... |
4 beds | 5 baths | 3,248 sq.ft. |
$2,350,000 |
Airbnb cash on cash: -0.82%
|
3475 Oaklawn AvenueSouthold, NYCirca-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, ... |
3 beds | 2 baths | 2,000 sq.ft. |
$1,200,000 |
Airbnb cash on cash: -0.13%
|
600 Glenn RoadSouthold, NYModern Luxury Waterfront Tree House - Nature Lovers' Paradise on West Creek! Discover this... |
4 beds | 6 baths | 3,000 sq.ft. |
$2,195,000 |
Airbnb cash on cash: -0.42%
|
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. |
$3,450,000 |
Airbnb cash on cash: -1.59%
|
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: -1.34%
|
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: -1.6%
|
1020 Ruch LaneSouthold, NYWelcome to Sunset Cottage! Perfectly situated on one of Southold's most desirable streets,... |
3 beds | 3 baths | 1,800 sq.ft. |
$1,835,000 |
Airbnb cash on cash: -0.83%
|
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: -0.89%
|
2070 Cedar DriveSouthold, NY2070 Cedar Drive offers the kind of North Fork lifestyle buyers search for but rarely find... |
2 beds | 1 baths | N/A |
$989,000 |
Airbnb cash on cash: -0.74%
|
265 Hummel AvenueSouthold, NYWelcome to 265 Hummel Ave in Southold, a charming two-bedroom, one-bathroom gem that embod... |
2 beds | 1 baths | 1,114 sq.ft. |
$649,000 |
Airbnb cash on cash: -0.18%
|
1815 Laurel AvenueSouthold, NYWelcome to the Laurel Collection by Marrcon. New Luxury Construction located in the heart ... |
4 beds | 5 baths | 4,327 sq.ft. |
$2,795,000 |
Airbnb cash on cash: -0.35%
|
3500 Pine Neck RoadSouthold, NYStep into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold-an ... |
3 beds | 3 baths | 2,000 sq.ft. |
$1,999,000 |
Airbnb cash on cash: -0.67%
|
5845 N Bayview RoadSouthold, NYTucked away in a peaceful enclave of Southold, this classic Cape Cod offers a private esca... |
3 beds | 2 baths | 1,989 sq.ft. |
$970,000 |
Airbnb cash on cash: 0.23%
|
6625 Hortons LaneSouthold, NYA beautiful and lovingly-maintained ranch with a front porch, set on a corner lot, offers ... |
3 beds | 2 baths | 1,500 sq.ft. |
$939,000 |
Airbnb cash on cash: 0.05%
|
240 Lisa DriveSouthold, NYWelcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highp... |
4 beds | 3 baths | 1,862 sq.ft. |
$949,000 |
Airbnb cash on cash: 0.58%
|
1135 Wildberry LaneSouthold, NYNorth Fork living, refined. Welcome to Wildberry. A newly constructed residence where desi... |
5 beds | 6 baths | 3,240 sq.ft. |
$2,895,000 |
Airbnb cash on cash: -1.07%
|
75 Birch RoadSouthold, NYTucked away on a beautifully landscaped property, this 2022 built 4 bedroom, 3.5 bath resi... |
4 beds | 4 baths | 2,584 sq.ft. |
$1,299,999 |
Airbnb cash on cash: 0.73%
|
5045 Main Bayview RoadSouthold, NYWelcome to this charming residence nestled in the heart of Southold. This gem boasts 4 spa... |
4 beds | 3 baths | 3,000 sq.ft. |
$1,099,000 |
Airbnb cash on cash: 0.38%
|
52755 Soundview AvenueSouthold, NYWelcome to this One-of-a-Kind 4-Bedroom, Custom Built Colonial, Beachfront Property, ideal... |
4 beds | 2 baths | 1,576 sq.ft. |
$1,299,999 |
Airbnb cash on cash: 0.13%
|
800 Corey Creek LaneSouthold, NYStunning new-construction coastal retreat with modern luxury and unmatched entertaining sp... |
4 beds | 5 baths | 3,025 sq.ft. |
$1,950,000 |
Airbnb cash on cash: -0.3%
|
380 Clark RoadSouthold, NYWelcome to 380 Clark Road, a sun-filled North Fork escape perfectly located near the beaut... |
2 beds | 1 baths | 1,500 sq.ft. |
$1,150,000 |
Airbnb cash on cash: -0.71%
|
250 Paradise Point RoadSouthold, NYWelcome to 250 Paradise Point Rd, Southold NY, a beautiful ranch-style home complete with ... |
4 beds | 3 baths | 2,200 sq.ft. |
$1,299,000 |
Airbnb cash on cash: 0.01%
|
1220 Youngs AvenueSouthold, NYWonderful Hamlet Business (HB) zoned property, in the heart of the Hamlet of Southold! Cur... |
2 beds | 1 baths | N/A |
$1,295,000 |
Airbnb cash on cash: -0.84%
|
1475 Laurel AvenueSouthold, NYWelcome to the Laurel Collection by Marrcon. New Luxury Construction located in the heart ... |
4 beds | 5 baths | 4,327 sq.ft. |
$2,795,000 |
Airbnb cash on cash: -0.3%
|
2555 Youngs Avenue #1DSouthold, NYGorgeous, light, bright, and airy, this immaculate 2-bedroom, 2-bath condominium is locate... |
2 beds | 2 baths | 1,100 sq.ft. |
$560,000 |
Airbnb cash on cash: 0.39%
|
4630 Youngs AvenueSouthold, NYCalling all artists or collectors of any kind! This is what you have been waiting for. Wel... |
2 beds | 2 baths | 3,603 sq.ft. |
$1,950,000 |
Airbnb cash on cash: -1.34%
|
Real Estate investment in Southold, NY
There are 34 properties for sale in the city of Southold . The median list price in Southold is $893,965 and the average price per square foot is $331. In July 2026, the average monthly cash on cash return in Southold is 2.00%. The average monthly rental income in Southold is $4,624.