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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
650 The Esplanade Southold, NY Southold, 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: 0.11% Traditional cash on cash: 1.72% Airbnb Rental Income: $3173 Traditional Rental Income: $4325 Airbnb ROI: 0.11% Traditional ROI: 1.72%
2015 Kenneys Rd Southold, NY Excellence Unsurpassed! Artisan Crafted Showpiece! No Holds Barred On Int/Ext Construct & ...	4 beds \| 3 baths \| 2,900 sq.ft.	$1,495,000	Airbnb cash on cash: -0.09% Traditional cash on cash: 1.62% Airbnb Rental Income: $3027 Traditional Rental Income: $4713 Airbnb ROI: -0.09% Traditional ROI: 1.62%
1350 Hortons Ln Southold, NY Take Advantage Of A Wonderful Opportunity To Design Your Own Custom Built Escape On 2.24 A...	8 beds \| 7 baths \| 5,600 sq.ft.	$2,799,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 1.73% Airbnb Rental Income: $236 Traditional Rental Income: $7863 Airbnb ROI: -1.3% Traditional ROI: 1.73%
470 Goose Creek Ln Southold, NY Waterfront 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: -0.51% Traditional cash on cash: 0.22% Airbnb Rental Income: $3173 Traditional Rental Income: $4088 Airbnb ROI: -0.51% Traditional ROI: 0.22%
700 Gin Lane Southold, NY Southold 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: -0.31% Traditional cash on cash: 1.24% Airbnb Rental Income: $3027 Traditional Rental Income: $4932 Airbnb ROI: -0.31% Traditional ROI: 1.24%
430 Grove Rd Southold, NY Enter 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: 1.84% Traditional cash on cash: 3.06% Airbnb Rental Income: $3173 Traditional Rental Income: $3253 Airbnb ROI: 1.84% Traditional ROI: 3.06%
600 Highwood Road Southold, NY Unique 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: -0.45% Traditional cash on cash: 0.84% Airbnb Rental Income: $1881 Traditional Rental Income: $2575 Airbnb ROI: -0.45% Traditional ROI: 0.84%
2100 Glenn Rd Southold, NY Waterfront With Dock In The Heart Of Wine Country! Extremely Low Taxes & Gorgeous Views, T...	4 beds \| 2 baths \| 2,850 sq.ft.	$1,849,000	Airbnb cash on cash: -0.14% Traditional cash on cash: 1.3% Airbnb Rental Income: $3027 Traditional Rental Income: $4807 Airbnb ROI: -0.14% Traditional ROI: 1.3%
465 Ripple Water Lane Southold, NY You 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: -1.11% Traditional cash on cash: 0.32% Airbnb Rental Income: $3027 Traditional Rental Income: $7097 Airbnb ROI: -1.11% Traditional ROI: 0.32%
25 Lighthouse Rd Southold, NY Tucked at the end of a long, private drive on one of Southold's historic streets, this cus...	4 beds \| 2 baths \| 3,800 sq.ft.	$1,899,000	Airbnb cash on cash: -0.35% Traditional cash on cash: 1.56% Airbnb Rental Income: $3027 Traditional Rental Income: $5712 Airbnb ROI: -0.35% Traditional ROI: 1.56%
150 Baywater Ave Southold, NY Charming Antique Fixer Upper/Project Home Set on One Acre. Bring Your Contractor. This C...	3 beds \| 4 baths \| 2,100 sq.ft.	$850,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 7.98% Airbnb Rental Income: $3173 Traditional Rental Income: $7857 Airbnb ROI: 1.16% Traditional ROI: 7.98%
535 Bay Home Rd Southold, NY Southold - Canal Front - Unique opportunity to transform this 1970's home into your North ...	3 beds \| 4 baths \| 2,900 sq.ft.	$1,499,000	Airbnb cash on cash: -0.03% Traditional cash on cash: 1.23% Airbnb Rental Income: $3173 Traditional Rental Income: $4223 Airbnb ROI: -0.03% Traditional ROI: 1.23%
150 Deer Run Southold, NY Gorgeous estate-like Nantucket shingle home in the final stage of construction. Designed b...	5 beds \| 4 baths \| 5,285 sq.ft.	$3,675,000	Airbnb cash on cash: -1.86% Traditional cash on cash: 1.25% Airbnb Rental Income: $236 Traditional Rental Income: $10588 Airbnb ROI: -1.86% Traditional ROI: 1.25%
3715 Hortons Ln Southold, NY Designer Modern Farmhouse set on over 3.35 Acres with farm and scenic views, Renovated 202...	4 beds \| 4 baths \| 2,200 sq.ft.	$1,599,999	Airbnb cash on cash: -0.26% Traditional cash on cash: 1.34% Airbnb Rental Income: $3027 Traditional Rental Income: $4712 Airbnb ROI: -0.26% Traditional ROI: 1.34%
1480 Old Wood Path Southold, NY Welcome to your own Peconic Bay beach & tennis paradise on 4 acres in Southold, a charming...	3 beds \| 4 baths \| 3,496 sq.ft.	$4,000,000	Airbnb cash on cash: -1.29% Traditional cash on cash: -0.27% Airbnb Rental Income: $3173 Traditional Rental Income: $6232 Airbnb ROI: -1.29% Traditional ROI: -0.27%
500 Summer Ln Southold, NY Property with vast potential in Prime location, close to Southold beaches, vineyards and s...	4 beds \| 3 baths \| 2,215 sq.ft.	$1,550,000	Airbnb cash on cash: 0.32% Traditional cash on cash: 0.7% Airbnb Rental Income: $3027 Traditional Rental Income: $2875 Airbnb ROI: 0.32% Traditional ROI: 0.7%
1665 Glenn Rd Southold, NY Newly built and beautifully enhanced with approx. $300K in upgrades since purchase, 1665 G...	4 beds \| 4 baths \| 3,248 sq.ft.	$2,250,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 2.76% Airbnb Rental Income: $3027 Traditional Rental Income: $9699 Airbnb ROI: -0.77% Traditional ROI: 2.76%
3475 Oaklawn Ave Southold, NY Circa-1909 Cozy Farmhouse Near the Water & Southold Village Welcome to 3475 Oaklawn Road, ...	3 beds \| 1 baths \| 2,000 sq.ft.	$1,099,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 0.93% Airbnb Rental Income: $3173 Traditional Rental Income: $2875 Airbnb ROI: 0.52% Traditional ROI: 0.93%
1750 Hobart Rd Southold, NY Welcome to a stunning, one-of-a-kind waterfront home in the highly sought-after hamlet of ...	5 beds \| 4 baths \| 4,627 sq.ft.	$6,850,000	Airbnb cash on cash: -1.1% Traditional cash on cash: -0.15% Airbnb Rental Income: $236 Traditional Rental Income: $6047 Airbnb ROI: -1.1% Traditional ROI: -0.15%
600 Glenn Road Southold, NY Modern 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: -0.37% Traditional cash on cash: 2.84% Airbnb Rental Income: $3027 Traditional Rental Income: $8866 Airbnb ROI: -0.37% Traditional ROI: 2.84%
790 N Sea Dr Southold, NY Quintessential North Fork Beach House!! Perched high above with breathtaking views of the ...	5 beds \| 3 baths \| 4,500 sq.ft.	$3,450,000	Airbnb cash on cash: -1.59% Traditional cash on cash: 0.46% Airbnb Rental Income: $236 Traditional Rental Income: $6557 Airbnb ROI: -1.59% Traditional ROI: 0.46%
3470 N Bayview Rd Southold, NY Welcome to luxury on the North Fork. This quality built home is located only 3 properties...	5 beds \| 4 baths \| 3,800 sq.ft.	$2,500,000	Airbnb cash on cash: -1.66% Traditional cash on cash: 1.66% Airbnb Rental Income: $236 Traditional Rental Income: $7704 Airbnb ROI: -1.66% Traditional ROI: 1.66%
80 Deer Run Southold, NY Southold Stunner- New Construction This one's a North Fork knockout. Set at the end of a q...	4 beds \| 5 baths \| 7,341 sq.ft.	$2,995,000	Airbnb cash on cash: -1.34% Traditional cash on cash: 0.93% Airbnb Rental Income: $3027 Traditional Rental Income: $8651 Airbnb ROI: -1.34% Traditional ROI: 0.93%
530 Sunset Way Southold, NY Wake 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% Traditional cash on cash: 0.97% Airbnb Rental Income: $236 Traditional Rental Income: $4053 Airbnb ROI: -1.6% Traditional ROI: 0.97%
1020 Ruch Lane Southold, NY Welcome 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: -0.49% Traditional cash on cash: 0.79% Airbnb Rental Income: $3173 Traditional Rental Income: $4624 Airbnb ROI: -0.49% Traditional ROI: 0.79%
450 Sterling Woods Lane Southold, NY Spacious 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: -0.85% Traditional cash on cash: 0.43% Airbnb Rental Income: $3027 Traditional Rental Income: $5060 Airbnb ROI: -0.85% Traditional ROI: 0.43%
2070 Cedar Drive Southold, NY 2070 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: -0.4% Traditional cash on cash: 0.98% Airbnb Rental Income: $1881 Traditional Rental Income: $2654 Airbnb ROI: -0.4% Traditional ROI: 0.98%
265 Hummel Avenue Southold, NY Welcome 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: 0.34% Traditional cash on cash: 2.53% Airbnb Rental Income: $1881 Traditional Rental Income: $2707 Airbnb ROI: 0.34% Traditional ROI: 2.53%
1815 Laurel Avenue Southold, NY Welcome 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: -0.32% Traditional cash on cash: 1.7% Airbnb Rental Income: $3027 Traditional Rental Income: $7555 Airbnb ROI: -0.32% Traditional ROI: 1.7%
52325 County Road 48 #31 Southold, NY 52325 County Road 48 #31, Southold, NY 11971 \| Condo/Coop	N/A beds \| 1 baths \| 250 sq.ft.	$239,000	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.34% Airbnb Rental Income: $2144 Traditional Rental Income: $1287 Airbnb ROI: 2.72% Traditional ROI: 1.34%
2055 Boisseau Ave Southold, NY 2055 Boisseau Ave, Southold, NY 11971 \| Single Family Residential	3 beds \| 1 baths \| 2,000 sq.ft.	$1,249,000	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.06% Airbnb Rental Income: $3173 Traditional Rental Income: $3175 Airbnb ROI: -0.68% Traditional ROI: -0.06%
105 Waterview Dr Southold, NY 105 Waterview Dr, Southold, NY 11971 \| Single Family Residential	6 beds \| 4 baths \| 4,663 sq.ft.	$3,695,000	Airbnb cash on cash: -2.74% Traditional cash on cash: -1.45% Airbnb Rental Income: $236 Traditional Rental Income: $4436 Airbnb ROI: -2.74% Traditional ROI: -1.45%
55975 Route 25 Southold, NY 55975 Route 25, Southold, NY 11971 \| Other	N/A beds \| N/A baths \| 0 sq.ft.	$1,600,000	Airbnb cash on cash: -1.7% Traditional cash on cash: -1.68% Airbnb Rental Income: $2144 Traditional Rental Income: $1633 Airbnb ROI: -1.7% Traditional ROI: -1.68%
3500 Pine Neck Rd Southold, NY Step into nearly three centuries of preserved history at 3500 Pine Neck Road, Southold-an ...	3 beds \| 2 baths \| 2,000 sq.ft.	$1,750,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 0.82% Airbnb Rental Income: $3173 Traditional Rental Income: $4217 Airbnb ROI: -0.26% Traditional ROI: 0.82%
5845 N Bayview Rd Southold, NY Tucked away in a peaceful enclave of Southold, this classic Cape Cod offers a private esca...	3 beds \| 2 baths \| 1,989 sq.ft.	$950,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 2.44% Airbnb Rental Income: $3173 Traditional Rental Income: $3803 Airbnb ROI: 0.91% Traditional ROI: 2.44%
6625 Hortons Lane Southold, NY A 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: 0.72% Traditional cash on cash: 1.83% Airbnb Rental Income: $3173 Traditional Rental Income: $3429 Airbnb ROI: 0.72% Traditional ROI: 1.83%
240 Lisa Dr Southold, NY Welcome to this spacious 4-bedroom, 2.5-bath two-story home located in the desirable Highp...	4 beds \| 2 baths \| 1,862 sq.ft.	$949,000	Airbnb cash on cash: 0.69% Traditional cash on cash: 3.07% Airbnb Rental Income: $3027 Traditional Rental Income: $4435 Airbnb ROI: 0.69% Traditional ROI: 3.07%
1135 Wildberry Ln Southold, NY North Fork living, refined. Welcome to Wildberry. A newly constructed residence where desi...	5 beds \| 5 baths \| 3,240 sq.ft.	$2,895,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 2.29% Airbnb Rental Income: $236 Traditional Rental Income: $9021 Airbnb ROI: -1.07% Traditional ROI: 2.29%
75 Birch Rd Southold, NY Tucked away on a beautifully landscaped property, this 2022 built 4 bedroom, 3.5 bath resi...	4 beds \| 3 baths \| 2,584 sq.ft.	$1,299,999	Airbnb cash on cash: 0.8% Traditional cash on cash: 3.39% Airbnb Rental Income: $3027 Traditional Rental Income: $5463 Airbnb ROI: 0.8% Traditional ROI: 3.39%
5045 Main Bayview Rd Southold, NY Welcome to this charming residence nestled in the heart of Southold. This gem boasts 4 spa...	4 beds \| 2 baths \| 3,000 sq.ft.	$999,000	Airbnb cash on cash: 0.63% Traditional cash on cash: 3.54% Airbnb Rental Income: $3027 Traditional Rental Income: $5047 Airbnb ROI: 0.63% Traditional ROI: 3.54%

Real Estate investment in Southold, NY

There are 75 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 $344. In September 2026, the average monthly cash on cash return in Southold is 1.00%. The average monthly rental income in Southold is $4,317.

Southold, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 75 investment properties available for sale in Southold.

In 2026, the best neighborhood to buy investment property is Southold.

The ROI for Short-Term is higher than the Long-Term in Southold with average rental income of $3,027.

Your search for investment property begins and ends here

Investment Property for Sale in Southold, NY

650 The Esplanade

Southold, NY

3 beds | 3 baths | 2,300 sq.ft.

$1,249,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 1.72%

Airbnb Rental Income: $3173

Traditional Rental Income: $4325

Airbnb ROI: 0.11%

Traditional ROI: 1.72%

2015 Kenneys Rd

Southold, NY

4 beds | 3 baths | 2,900 sq.ft.

$1,495,000

Airbnb cash on cash: -0.09%

Traditional cash on cash: 1.62%

Airbnb Rental Income: $3027

Traditional Rental Income: $4713

Airbnb ROI: -0.09%

Traditional ROI: 1.62%

1350 Hortons Ln

Southold, NY

8 beds | 7 baths | 5,600 sq.ft.

$2,799,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 1.73%

Airbnb Rental Income: $236

Traditional Rental Income: $7863

Airbnb ROI: -1.3%

Traditional ROI: 1.73%

470 Goose Creek Ln

Southold, NY

3 beds | 2 baths | 2,000 sq.ft.

$2,399,000

Airbnb cash on cash: -0.51%

Traditional cash on cash: 0.22%

Airbnb Rental Income: $3173

Traditional Rental Income: $4088

Airbnb ROI: -0.51%

Traditional ROI: 0.22%

700 Gin Lane

Southold, NY

4 beds | 4 baths | 2,627 sq.ft.

$1,799,995

Airbnb cash on cash: -0.31%

Traditional cash on cash: 1.24%

Airbnb Rental Income: $3027

Traditional Rental Income: $4932

Airbnb ROI: -0.31%

Traditional ROI: 1.24%

430 Grove Rd

Southold, NY

3 beds | 1 baths | N/A

$699,000

Airbnb cash on cash: 1.84%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3173

Traditional Rental Income: $3253

Airbnb ROI: 1.84%

Traditional ROI: 3.06%

600 Highwood Road

Southold, NY

2 beds | 1 baths | 1,954 sq.ft.

$999,999

Airbnb cash on cash: -0.45%

Traditional cash on cash: 0.84%

Airbnb Rental Income: $1881

Traditional Rental Income: $2575

Airbnb ROI: -0.45%

Traditional ROI: 0.84%

2100 Glenn Rd

Southold, NY

4 beds | 2 baths | 2,850 sq.ft.

$1,849,000

Airbnb cash on cash: -0.14%

Traditional cash on cash: 1.3%

Airbnb Rental Income: $3027

Traditional Rental Income: $4807

Airbnb ROI: -0.14%