Real Estate Investment Properties for Sale in Southampton, NY

Looking for investment property in Southampton, NY with high ROI ?

Explore a variety of short-term homes & houses in Southampton, NY. Invest wisely with VRBO & Southampton, 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 Southampton, NY

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
73 Charla Drive Southampton, NY SOUTHAMPTON WITH ALL THE BELLS AND WHISTLES Introducing a pristine turn key, updated spraw...	3 beds \| 3 baths \| 1,476 sq.ft.	$1,665,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 1.07% Airbnb Rental Income: $1469 Traditional Rental Income: $3973 Airbnb ROI: -0.83% Traditional ROI: 1.07%
4 White Oak Lane Southampton, NY Set on 1.69 beautifully landscaped acres in a peaceful setting, this renovated traditional...	4 beds \| 6 baths \| 4,700 sq.ft.	$3,495,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 1.23% Airbnb Rental Income: $898 Traditional Rental Income: $8783 Airbnb ROI: -1.3% Traditional ROI: 1.23%
30 Blackwatch Court Southampton, NY 30 Blackwatch Court, Southampton: A revitalized retreat where cedar-shingle tradition meet...	4 beds \| 4 baths \| 3,300 sq.ft.	$3,345,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 0.04% Airbnb Rental Income: $898 Traditional Rental Income: $4716 Airbnb ROI: -1.3% Traditional ROI: 0.04%
28 Apple Road Southampton, NY This 0.34-acre property features a 1.5-story clean 3-bedroom house and a pool. This nearly...	3 beds \| 1 baths \| 1,450 sq.ft.	$1,137,698	Airbnb cash on cash: -0.28% Traditional cash on cash: 1.76% Airbnb Rental Income: $1469 Traditional Rental Income: $3194 Airbnb ROI: -0.28% Traditional ROI: 1.76%
40 Knollwood Drive Southampton, NY Recently completed and fully staged, this impeccably priced five-bedroom residence sits on...	5 beds \| 4 baths \| 2,800 sq.ft.	$2,995,000	Airbnb cash on cash: -1.21% Traditional cash on cash: 3.48% Airbnb Rental Income: $974 Traditional Rental Income: $13629 Airbnb ROI: -1.21% Traditional ROI: 3.48%
40 Highlands Drive Southampton, NY Tucked away on a peaceful cul-de-sac in Glenview Hills, North Sea, this New York/Palm Beac...	3 beds \| 2 baths \| 1,241 sq.ft.	$1,775,000	Airbnb cash on cash: -0.6% Traditional cash on cash: 0.78% Airbnb Rental Income: $1469 Traditional Rental Income: $3325 Airbnb ROI: -0.6% Traditional ROI: 0.78%
14 Landing Lane Southampton, NY Conveniently located on the fringe of Southampton Village, this beautifully renovated 2-be...	2 beds \| 2 baths \| 1,500 sq.ft.	$1,449,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.74% Airbnb Rental Income: $1546 Traditional Rental Income: $3055 Airbnb ROI: -0.71% Traditional ROI: 0.74%
138 Longview Road Southampton, NY Beautifully renovated one-story home with a fully finished basement offering generous livi...	3 beds \| 3 baths \| 1,813 sq.ft.	$1,795,000	Airbnb cash on cash: -0.81% Traditional cash on cash: 5.16% Airbnb Rental Income: $1469 Traditional Rental Income: $10985 Airbnb ROI: -0.81% Traditional ROI: 5.16%
845 County Road 39 Southampton, NY Experience the pinnacle of Hamptons living in this exclusive, first-time-offered home in t...	4 beds \| 3 baths \| 1,534 sq.ft.	$1,600,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 4% Airbnb Rental Income: $898 Traditional Rental Income: $7960 Airbnb ROI: -0.98% Traditional ROI: 4%
39 Halsey Avenue Southampton, NY Heart of Southampton Village! You can renovate this property and move in. Or you could bui...	6 beds \| 5 baths \| N/A	$2,300,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 1.88% Airbnb Rental Income: $974 Traditional Rental Income: $7100 Airbnb ROI: -1.16% Traditional ROI: 1.88%
195 Little Fresh Pond Road Southampton, NY Located in just down the road from Little Fresh Pond Road you will find this meticulously ...	3 beds \| 4 baths \| 1,800 sq.ft.	$1,995,000	Airbnb cash on cash: -0.63% Traditional cash on cash: 3.37% Airbnb Rental Income: $1469 Traditional Rental Income: $8436 Airbnb ROI: -0.63% Traditional ROI: 3.37%
32 Cooper Street Southampton, NY Southampton Village Classic with Legal Guest House An exceptional opportunity to own a cla...	5 beds \| 3 baths \| 2,537 sq.ft.	$3,250,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 0.43% Airbnb Rental Income: $974 Traditional Rental Income: $4830 Airbnb ROI: -0.97% Traditional ROI: 0.43%
8 Landsend Lane Southampton, NY Set along the shoreline of the coveted Cold Spring Point Beach Community, this newly reima...	4 beds \| 3 baths \| 2,270 sq.ft.	$2,995,000	Airbnb cash on cash: -1.24% Traditional cash on cash: 0.08% Airbnb Rental Income: $898 Traditional Rental Income: $4240 Airbnb ROI: -1.24% Traditional ROI: 0.08%
601 Majors Path Southampton, NY This recently renovated luxury escape just outside Southampton Village is turnkey and read...	3 beds \| 3 baths \| 2,940 sq.ft.	$2,195,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 0.48% Airbnb Rental Income: $1469 Traditional Rental Income: $3467 Airbnb ROI: -0.71% Traditional ROI: 0.48%
311 Noyac Road Southampton, NY Owners Encouraging All Offers Now Avail for Sale, a 2.61 acre lot with pre-existing 3 ...	3 beds \| 2 baths \| N/A	$4,495,000	Airbnb cash on cash: -2.49% Traditional cash on cash: -1.92% Airbnb Rental Income: $1469 Traditional Rental Income: $3394 Airbnb ROI: -2.49% Traditional ROI: -1.92%
210 Towd Point Road Southampton, NY Discover a world of coastal serenity in the heart of Southampton's historic Towd Point art...	3 beds \| 4 baths \| 2,122 sq.ft.	$3,825,000	Airbnb cash on cash: -0.92% Traditional cash on cash: 0.03% Airbnb Rental Income: $1469 Traditional Rental Income: $4396 Airbnb ROI: -0.92% Traditional ROI: 0.03%
142 Towd Point Road Southampton, NY The best of coastal contemporary living in the Hamptons awaits in this stunning new constr...	4 beds \| 5 baths \| 2,800 sq.ft.	$4,995,000	Airbnb cash on cash: -1.2% Traditional cash on cash: -0.06% Airbnb Rental Income: $898 Traditional Rental Income: $5860 Airbnb ROI: -1.2% Traditional ROI: -0.06%
44 Ocean View Parkway Southampton, NY Just imagine pulling into your gated, stunning, traditional home in Southampton. Spread ac...	5 beds \| 6 baths \| 5,260 sq.ft.	$4,495,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0.46% Airbnb Rental Income: $974 Traditional Rental Income: $6764 Airbnb ROI: -1.02% Traditional ROI: 0.46%
29 Kenwood Road Southampton, NY Discover a hidden gem with breathtaking water views in the exclusive Sandringham Beach com...	4 beds \| 4 baths \| 3,500 sq.ft.	$2,865,000	Airbnb cash on cash: -1.23% Traditional cash on cash: 0.42% Airbnb Rental Income: $898 Traditional Rental Income: $4936 Airbnb ROI: -1.23% Traditional ROI: 0.42%
67 Straight Path Southampton, NY Ideally situated in Southampton surrounded by multi-million dollar homes and just 4 minute...	3 beds \| 4 baths \| 2,902 sq.ft.	$1,750,000	Airbnb cash on cash: -0.71% Traditional cash on cash: 1.23% Airbnb Rental Income: $1469 Traditional Rental Income: $4191 Airbnb ROI: -0.71% Traditional ROI: 1.23%
15 McGregor Drive Southampton, NY Discover your forever home in the Hamptons in an enviable Southampton location with waterv...	4 beds \| 3 baths \| 2,350 sq.ft.	$2,495,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.64% Airbnb Rental Income: $898 Traditional Rental Income: $4650 Airbnb ROI: -1.13% Traditional ROI: 0.64%
292 Little Fresh Pond Road Southampton, NY LIGHT FILLED CONTEMPORARY CLOSE TO LITTLE FRESH POND & VILLAGE OF SOUTHAMPTON! This charmi...	3 beds \| 3 baths \| 1,812 sq.ft.	$1,345,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 1.99% Airbnb Rental Income: $1469 Traditional Rental Income: $4104 Airbnb ROI: -0.47% Traditional ROI: 1.99%
19 Inlet View Drive Southampton, NY Sophisticated coastal living meets modern design in this new construction home in Shinneco...	4 beds \| 4 baths \| 2,800 sq.ft.	$2,195,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 1.6% Airbnb Rental Income: $898 Traditional Rental Income: $5579 Airbnb ROI: -0.86% Traditional ROI: 1.6%
520 Hampton Road unit: 5 Southampton, NY Location Location Location in Southampton Village. This residence is located within the 30...	3 beds \| 3 baths \| 2,364 sq.ft.	$1,850,000	Airbnb cash on cash: -1.57% Traditional cash on cash: 0.42% Airbnb Rental Income: $1469 Traditional Rental Income: $4447 Airbnb ROI: -1.57% Traditional ROI: 0.42%
113 Sebonac Road Southampton, NY Discover this charming traditional home situated on a spacious .74-acre lot in prime South...	5 beds \| 6 baths \| 4,085 sq.ft.	$3,995,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 0.94% Airbnb Rental Income: $974 Traditional Rental Income: $8747 Airbnb ROI: -1.25% Traditional ROI: 0.94%
40 Scrimshaw Drive Southampton, NY Nestled in a highly sought-after beach community on the Peconic Bay, this lovely, bright, ...	3 beds \| 3 baths \| 1,642 sq.ft.	$1,875,000	Airbnb cash on cash: -0.68% Traditional cash on cash: 1.1% Airbnb Rental Income: $1469 Traditional Rental Income: $4132 Airbnb ROI: -0.68% Traditional ROI: 1.1%
251 Sebonac Road Southampton, NY Seller is installing a brand new septic system	4 beds \| 6 baths \| 1,904 sq.ft.	$2,495,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 0.78% Airbnb Rental Income: $898 Traditional Rental Income: $5238 Airbnb ROI: -1.25% Traditional ROI: 0.78%
1323 Meadow Lane Southampton, NY Now available, this extraordinary South of the Highway bayfront double-lot estate on South...	5 beds \| 6 baths \| 5,300 sq.ft.	$16,900,000	Airbnb cash on cash: -1.3% Traditional cash on cash: -0.73% Airbnb Rental Income: $974 Traditional Rental Income: $9433 Airbnb ROI: -1.3% Traditional ROI: -0.73%
115 Highland Road Southampton, NY Southampton Sanctuary with Space to Spare Set on an expansive 1.68 acre parcel in a peacef...	5 beds \| 5 baths \| 6,211 sq.ft.	$2,475,000	Airbnb cash on cash: -1.3% Traditional cash on cash: 1.88% Airbnb Rental Income: $974 Traditional Rental Income: $7933 Airbnb ROI: -1.3% Traditional ROI: 1.88%
91 Dale Street Southampton, NY Nestled in the Village of Southampton is this charming 3 to 4 bedrooms, 3 bath home. There...	4 beds \| 3 baths \| 2,044 sq.ft.	$2,650,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 0.72% Airbnb Rental Income: $898 Traditional Rental Income: $4691 Airbnb ROI: -0.96% Traditional ROI: 0.72%
76 Blackwatch Court Southampton, NY Designed for the ultimate in indoor-outdoor living, this 4-bedroom, 3.5-baths contemporary...	4 beds \| 4 baths \| 2,950 sq.ft.	$1,995,000	Airbnb cash on cash: -1.14% Traditional cash on cash: 0.88% Airbnb Rental Income: $898 Traditional Rental Income: $4300 Airbnb ROI: -1.14% Traditional ROI: 0.88%
63 Halsey Street Southampton, NY Tucked away on a quiet private cul-de-sac in the heart of Southampton Village, 63 Halsey S...	4 beds \| 3 baths \| 2,288 sq.ft.	$3,995,000	Airbnb cash on cash: -1.11% Traditional cash on cash: 0.05% Airbnb Rental Income: $898 Traditional Rental Income: $4874 Airbnb ROI: -1.11% Traditional ROI: 0.05%
38 East Beach Drive Southampton, NY Rarely does a waterfront property come on the market in this desirable Southampton Shores ...	4 beds \| 2 baths \| 1,645 sq.ft.	$3,395,000	Airbnb cash on cash: -1.02% Traditional cash on cash: 0% Airbnb Rental Income: $898 Traditional Rental Income: $3798 Airbnb ROI: -1.02% Traditional ROI: 0%
30 Fords Lane Southampton, NY Come see this 3br, 2bth Ranch home which facilitates a Master bedroom located in a quiet n...	3 beds \| 2 baths \| 1,200 sq.ft.	$900,000	Airbnb cash on cash: -0.33% Traditional cash on cash: 2.45% Airbnb Rental Income: $1469 Traditional Rental Income: $3362 Airbnb ROI: -0.33% Traditional ROI: 2.45%
71 Sebonac Inlet Road Southampton, NY Classic Hamptons Living on Sebonac Inlet. Discover timeless Hamptons living at this tradit...	4 beds \| 3 baths \| 2,914 sq.ft.	$1,950,000	Airbnb cash on cash: -1.26% Traditional cash on cash: 0.91% Airbnb Rental Income: $898 Traditional Rental Income: $4483 Airbnb ROI: -1.26% Traditional ROI: 0.91%
59/61 Whalebone Landing Road Southampton, NY At its new price, the property stands out as one of the most compelling beach-proximate of...	4 beds \| 2 baths \| 2,200 sq.ft.	$1,750,000	Airbnb cash on cash: -0.98% Traditional cash on cash: 1.11% Airbnb Rental Income: $898 Traditional Rental Income: $3955 Airbnb ROI: -0.98% Traditional ROI: 1.11%
22 Fern Road Southampton, NY This is what you've been waiting for - a picture-perfect Hamptons home with 3 bedrooms and...	3 beds \| 3 baths \| 2,100 sq.ft.	$1,795,000	Airbnb cash on cash: -0.61% Traditional cash on cash: 1.3% Airbnb Rental Income: $1469 Traditional Rental Income: $4216 Airbnb ROI: -0.61% Traditional ROI: 1.3%
6 Shore Road Southampton, NY NEW IN NORTH SEA 3BR 2BA $999,000 + 3 WATER ACCESSES Low Taxes NEW to Market in North Sea ...	3 beds \| 2 baths \| 1,200 sq.ft.	$999,000	Airbnb cash on cash: -0.26% Traditional cash on cash: 2.3% Airbnb Rental Income: $1469 Traditional Rental Income: $3415 Airbnb ROI: -0.26% Traditional ROI: 2.3%
201 Herrick Road Southampton, NY Located in the heart of the Estate Section, 201 Herrick Road offers a rare combination of ...	5 beds \| 3 baths \| 2,669 sq.ft.	$3,995,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 0.08% Airbnb Rental Income: $974 Traditional Rental Income: $4857 Airbnb ROI: -1.07% Traditional ROI: 0.08%
94 Post Lane Southampton, NY SOUTHAMPTON VILLAGE CHARMER Historic Southampton Village Treasure with Pool, Barn & Lush G...	4 beds \| 4 baths \| 3,000 sq.ft.	$6,795,000	Airbnb cash on cash: -1.14% Traditional cash on cash: -0.26% Airbnb Rental Income: $898 Traditional Rental Income: $6130 Airbnb ROI: -1.14% Traditional ROI: -0.26%

Real Estate investment in Southampton, NY

There are 59 properties for sale in the city of Southampton . The median list price in Southampton is $2,197,500 and the average price per square foot is $729. In April 2026, the average monthly cash on cash return in Southampton is 1.00%. The average monthly rental income in Southampton is $5,087.

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

There are 59 investment properties available for sale in Southampton.

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

The ROI for Long-Term is higher than the Short-Term in Southampton with average rental income of $5,087.

Your search for investment property begins and ends here

Investment Property for Sale in Southampton, NY

73 Charla Drive

Southampton, NY

3 beds | 3 baths | 1,476 sq.ft.

$1,665,000

Airbnb cash on cash: -0.83%

Traditional cash on cash: 1.07%

Airbnb Rental Income: $1469

Traditional Rental Income: $3973

Airbnb ROI: -0.83%

Traditional ROI: 1.07%

4 White Oak Lane

Southampton, NY

4 beds | 6 baths | 4,700 sq.ft.

$3,495,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 1.23%

Airbnb Rental Income: $898

Traditional Rental Income: $8783

Airbnb ROI: -1.3%

Traditional ROI: 1.23%

30 Blackwatch Court

Southampton, NY

4 beds | 4 baths | 3,300 sq.ft.

$3,345,000

Airbnb cash on cash: -1.3%

Traditional cash on cash: 0.04%

Airbnb Rental Income: $898

Traditional Rental Income: $4716

Airbnb ROI: -1.3%

Traditional ROI: 0.04%

28 Apple Road

Southampton, NY

3 beds | 1 baths | 1,450 sq.ft.

$1,137,698

Airbnb cash on cash: -0.28%

Traditional cash on cash: 1.76%

Airbnb Rental Income: $1469

Traditional Rental Income: $3194

Airbnb ROI: -0.28%

Traditional ROI: 1.76%

40 Knollwood Drive

Southampton, NY

5 beds | 4 baths | 2,800 sq.ft.

$2,995,000

Airbnb cash on cash: -1.21%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $974

Traditional Rental Income: $13629

Airbnb ROI: -1.21%

Traditional ROI: 3.48%

40 Highlands Drive

Southampton, NY

3 beds | 2 baths | 1,241 sq.ft.

$1,775,000

Airbnb cash on cash: -0.6%

Traditional cash on cash: 0.78%

Airbnb Rental Income: $1469

Traditional Rental Income: $3325

Airbnb ROI: -0.6%

Traditional ROI: 0.78%

14 Landing Lane

Southampton, NY

2 beds | 2 baths | 1,500 sq.ft.

$1,449,000

Airbnb cash on cash: -0.71%

Traditional cash on cash: 0.74%

Airbnb Rental Income: $1546

Traditional Rental Income: $3055

Airbnb ROI: -0.71%

Traditional ROI: 0.74%

138 Longview Road

Southampton, NY

3 beds | 3 baths | 1,813 sq.ft.

$1,795,000

Airbnb cash on cash: -0.81%

Traditional cash on cash: 5.16%

Airbnb Rental Income: $1469

Traditional Rental Income: $10985

Airbnb ROI: -0.81%