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
28 Dundee Lane Southampton, NY Only two miles to the center of Southampton Village - this fully renovated traditional hom...	4 beds \| 3 baths \| 2,200 sq.ft.	$3,395,000	Airbnb cash on cash: -1.2% Traditional cash on cash: 0.19% Airbnb Rental Income: $443 Traditional Rental Income: $4543 Airbnb ROI: -1.2% Traditional ROI: 0.19%
56 Middle Pond Road Southampton, NY Set on 0.63 acres with waterside pool and 110Ft of bulkhead, this prime waterfront is loca...	4 beds \| 4 baths \| 3,772 sq.ft.	$5,500,000	Airbnb cash on cash: -1.29% Traditional cash on cash: 0.66% Airbnb Rental Income: $443 Traditional Rental Income: $10090 Airbnb ROI: -1.29% Traditional ROI: 0.66%
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.	$3,320,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 0.05% Airbnb Rental Income: $443 Traditional Rental Income: $4716 Airbnb ROI: -1.43% Traditional ROI: 0.05%
411 North Main Street Southampton, NY Discover your ideal residence in this charming and impeccably maintained 3-bedroom, 2-bath...	3 beds \| 2 baths \| 1,692 sq.ft.	$1,995,000	Airbnb cash on cash: -0.77% Traditional cash on cash: 0.76% Airbnb Rental Income: $1178 Traditional Rental Income: $3639 Airbnb ROI: -0.77% Traditional ROI: 0.76%
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: -0.51% Traditional cash on cash: 1.76% Airbnb Rental Income: $1178 Traditional Rental Income: $3194 Airbnb ROI: -0.51% Traditional ROI: 1.76%
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.	$1,695,000	Airbnb cash on cash: -0.74% Traditional cash on cash: 0.87% Airbnb Rental Income: $1178 Traditional Rental Income: $3325 Airbnb ROI: -0.74% Traditional ROI: 0.87%
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: -0.16% Traditional cash on cash: 0.74% Airbnb Rental Income: $2430 Traditional Rental Income: $3055 Airbnb ROI: -0.16% Traditional ROI: 0.74%
39 Cedar Drive Southampton, NY Southampton investment property offering a rare multi-structure compound on approximately ...	3 beds \| 4 baths \| N/A	$2,100,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 4.88% Airbnb Rental Income: $1178 Traditional Rental Income: $12789 Airbnb ROI: -1.28% Traditional ROI: 4.88%
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: -1.23% Traditional cash on cash: 4% Airbnb Rental Income: $443 Traditional Rental Income: $7960 Airbnb ROI: -1.23% 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: -1.26% Traditional cash on cash: 1.88% Airbnb Rental Income: $711 Traditional Rental Income: $7100 Airbnb ROI: -1.26% Traditional ROI: 1.88%
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.	$2,095,000	Airbnb cash on cash: -0.83% Traditional cash on cash: 0.55% Airbnb Rental Income: $1178 Traditional Rental Income: $3467 Airbnb ROI: -0.83% Traditional ROI: 0.55%
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: -0.99% Traditional cash on cash: 0.03% Airbnb Rental Income: $1178 Traditional Rental Income: $4396 Airbnb ROI: -0.99% Traditional ROI: 0.03%
115 Heady Creek Lane Southampton, NY Treasured by the same family for decades and now available for resale for the first time e...	5 beds \| 4 baths \| 3,800 sq.ft.	$8,495,000	Airbnb cash on cash: -2.67% Traditional cash on cash: -2.11% Airbnb Rental Income: $711 Traditional Rental Income: $4834 Airbnb ROI: -2.67% Traditional ROI: -2.11%
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: -1.07% Traditional cash on cash: 0.46% Airbnb Rental Income: $711 Traditional Rental Income: $6764 Airbnb ROI: -1.07% 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: -1.37% Traditional cash on cash: 0.42% Airbnb Rental Income: $443 Traditional Rental Income: $4936 Airbnb ROI: -1.37% Traditional ROI: 0.42%
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: -1.29% Traditional cash on cash: 0.64% Airbnb Rental Income: $443 Traditional Rental Income: $4650 Airbnb ROI: -1.29% Traditional ROI: 0.64%
44 Straight Path Southampton, NY Tucked away in the sought-after North Sea section of Southampton, this beautifully curated...	3 beds \| 2 baths \| 1,258 sq.ft.	$2,495,000	Airbnb cash on cash: -0.84% Traditional cash on cash: 0.78% Airbnb Rental Income: $1178 Traditional Rental Income: $4535 Airbnb ROI: -0.84% Traditional ROI: 0.78%
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.	$1,295,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 2.1% Airbnb Rental Income: $1178 Traditional Rental Income: $4104 Airbnb ROI: -0.65% Traditional ROI: 2.1%
19 Inlet View Drive Southampton, NY Sophisticated coastal living meets modern design in this new construction home in Southamp...	4 beds \| 4 baths \| 2,800 sq.ft.	$1,995,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 1.77% Airbnb Rental Income: $443 Traditional Rental Income: $5579 Airbnb ROI: -1.15% Traditional ROI: 1.77%
25 WHITE OAK LN Southampton, NY Set on a quiet stretch of White Oak Lane, this beautifully reimagined Southampton residenc...	4 beds \| 5 baths \| N/A	$3,495,000	Airbnb cash on cash: -1.28% Traditional cash on cash: 0.58% Airbnb Rental Income: $443 Traditional Rental Income: $6182 Airbnb ROI: -1.28% Traditional ROI: 0.58%
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.	$3,895,000	Airbnb cash on cash: -1.32% Traditional cash on cash: 0.99% Airbnb Rental Income: $711 Traditional Rental Income: $8747 Airbnb ROI: -1.32% Traditional ROI: 0.99%
251 Sebonac Road Southampton, NY Seller is installing a brand new septic system	4 beds \| 6 baths \| 1,904 sq.ft.	$2,395,000	Airbnb cash on cash: -1.43% Traditional cash on cash: 0.85% Airbnb Rental Income: $443 Traditional Rental Income: $5238 Airbnb ROI: -1.43% Traditional ROI: 0.85%
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: -1.31% Traditional cash on cash: -0.73% Airbnb Rental Income: $711 Traditional Rental Income: $9433 Airbnb ROI: -1.31% Traditional ROI: -0.73%
163 Halsey Street Southampton, NY This Southampton Village Cape cod cottage encapsulates the timeless allure and relaxed sop...	3 beds \| 2 baths \| 1,785 sq.ft.	$3,475,000	Airbnb cash on cash: -0.96% Traditional cash on cash: 0.02% Airbnb Rental Income: $1178 Traditional Rental Income: $3968 Airbnb ROI: -0.96% Traditional ROI: 0.02%
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.	$1,795,000	Airbnb cash on cash: -1.39% Traditional cash on cash: 1.08% Airbnb Rental Income: $443 Traditional Rental Income: $4300 Airbnb ROI: -1.39% Traditional ROI: 1.08%
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.	$3,195,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 0.07% Airbnb Rental Income: $443 Traditional Rental Income: $3798 Airbnb ROI: -1.15% Traditional ROI: 0.07%
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: -1.47% Traditional cash on cash: 0.91% Airbnb Rental Income: $443 Traditional Rental Income: $4483 Airbnb ROI: -1.47% Traditional ROI: 0.91%
509 N Main Street Southampton, NY Completely Renovated Southampton Gem! Set on a beautifully landscaped 0.7-acre corner lot ...	4 beds \| 6 baths \| 3,000 sq.ft.	$3,495,000	Airbnb cash on cash: -1.15% Traditional cash on cash: 1.3% Airbnb Rental Income: $443 Traditional Rental Income: $8116 Airbnb ROI: -1.15% 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.	$969,000	Airbnb cash on cash: -0.5% Traditional cash on cash: 2.4% Airbnb Rental Income: $1178 Traditional Rental Income: $3415 Airbnb ROI: -0.5% Traditional ROI: 2.4%
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.	$3,795,000	Airbnb cash on cash: -1.13% Traditional cash on cash: 0.13% Airbnb Rental Income: $711 Traditional Rental Income: $4857 Airbnb ROI: -1.13% Traditional ROI: 0.13%
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.	$6,495,000	Airbnb cash on cash: -1.21% Traditional cash on cash: -0.22% Airbnb Rental Income: $443 Traditional Rental Income: $6130 Airbnb ROI: -1.21% Traditional ROI: -0.22%
10 Bay View Road N Southampton, NY Beautifully designed with a sleek, minimalist style this home and shows like nearly new. O...	4 beds \| 5 baths \| 3,600 sq.ft.	$2,999,000	Airbnb cash on cash: -1.1% Traditional cash on cash: 1.55% Airbnb Rental Income: $443 Traditional Rental Income: $7550 Airbnb ROI: -1.1% Traditional ROI: 1.55%
40 Waters Edge Road Southampton, NY Experience an inspired blend of Southern elegance and modern Hamptons living in this stunn...	5 beds \| 6 baths \| 3,000 sq.ft.	$3,395,000	Airbnb cash on cash: -1.19% Traditional cash on cash: 1.35% Airbnb Rental Income: $711 Traditional Rental Income: $8411 Airbnb ROI: -1.19% Traditional ROI: 1.35%
27 Atterbury Road Southampton, NY South of the Highway Gem - Two Houses from Shinnecock Bay Perfectly situated South of the ...	4 beds \| 4 baths \| 2,600 sq.ft.	$2,199,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 1.12% Airbnb Rental Income: $443 Traditional Rental Income: $5513 Airbnb ROI: -1.49% Traditional ROI: 1.12%
360 Hill Street Southampton, NY A rare opportunity has arrived in the heart of Southampton Village. A 1925 classic cottage...	2 beds \| 1 baths \| 1,216 sq.ft.	$3,495,000	Airbnb cash on cash: -0.68% Traditional cash on cash: -0.3% Airbnb Rental Income: $2218 Traditional Rental Income: $2893 Airbnb ROI: -0.68% Traditional ROI: -0.3%
45 Wooley Street Southampton, NY Set on a quiet Southampton Village street, this classic village home offers the timeless H...	3 beds \| 4 baths \| 2,366 sq.ft.	$3,675,000	Airbnb cash on cash: -1.01% Traditional cash on cash: 0.3% Airbnb Rental Income: $1178 Traditional Rental Income: $5253 Airbnb ROI: -1.01% Traditional ROI: 0.3%
64 East Shore Road Southampton, NY This wonderful beach house with views of Little Peconic Bay, is sited in a private beachfr...	2 beds \| 2 baths \| 1,697 sq.ft.	$1,495,000	Airbnb cash on cash: -0.07% Traditional cash on cash: 1.15% Airbnb Rental Income: $2218 Traditional Rental Income: $3363 Airbnb ROI: -0.07% Traditional ROI: 1.15%
2 BRIDIES PATH Southampton, NY Move right into this beautifully expanded and renovated Southampton home set on .5 acre. O...	4 beds \| 4 baths \| 2,336 sq.ft.	$1,695,000	Airbnb cash on cash: -2.66% Traditional cash on cash: 0.57% Airbnb Rental Income: $443 Traditional Rental Income: $5254 Airbnb ROI: -2.66% Traditional ROI: 0.57%
5 Knoll Road Southampton, NY Beautifully constructed and thoughtfully designed, this stunning home offers the perfect b...	5 beds \| 5 baths \| 3,210 sq.ft.	$3,995,000	Airbnb cash on cash: -1.12% Traditional cash on cash: 0.82% Airbnb Rental Income: $711 Traditional Rental Income: $7586 Airbnb ROI: -1.12% Traditional ROI: 0.82%
10 Phillips Lane Southampton, NY A luxurious yet comfortably beachy waterside retreat, this Southampton waterfront home on ...	3 beds \| 3 baths \| 1,765 sq.ft.	$2,495,000	Airbnb cash on cash: -1.16% Traditional cash on cash: 0.37% Airbnb Rental Income: $1178 Traditional Rental Income: $4340 Airbnb ROI: -1.16% Traditional ROI: 0.37%

Real Estate investment in Southampton, NY

There are 68 properties for sale in the city of Southampton . The median list price in Southampton is $2,398,565 and the average price per square foot is $877. In July 2026, the average monthly cash on cash return in Southampton is 1.00%. The average monthly rental income in Southampton is $4,846.

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

There are 68 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 $4,846.

Your search for investment property begins and ends here

Investment Property for Sale in Southampton, NY

28 Dundee Lane

Southampton, NY

4 beds | 3 baths | 2,200 sq.ft.

$3,395,000

Airbnb cash on cash: -1.2%

Traditional cash on cash: 0.19%

Airbnb Rental Income: $443

Traditional Rental Income: $4543

Airbnb ROI: -1.2%

Traditional ROI: 0.19%

56 Middle Pond Road

Southampton, NY

4 beds | 4 baths | 3,772 sq.ft.

$5,500,000

Airbnb cash on cash: -1.29%

Traditional cash on cash: 0.66%

Airbnb Rental Income: $443

Traditional Rental Income: $10090

Airbnb ROI: -1.29%

Traditional ROI: 0.66%

30 Blackwatch Court

Southampton, NY

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

$3,320,000

Airbnb cash on cash: -1.43%

Traditional cash on cash: 0.05%

Airbnb Rental Income: $443

Traditional Rental Income: $4716

Airbnb ROI: -1.43%

Traditional ROI: 0.05%

411 North Main Street

Southampton, NY

3 beds | 2 baths | 1,692 sq.ft.

$1,995,000

Airbnb cash on cash: -0.77%

Traditional cash on cash: 0.76%

Airbnb Rental Income: $1178

Traditional Rental Income: $3639

Airbnb ROI: -0.77%

Traditional ROI: 0.76%

28 Apple Road

Southampton, NY

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

$1,137,698

Airbnb cash on cash: -0.51%

Traditional cash on cash: 1.76%

Airbnb Rental Income: $1178

Traditional Rental Income: $3194

Airbnb ROI: -0.51%

Traditional ROI: 1.76%

40 Highlands Drive

Southampton, NY

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

$1,695,000

Airbnb cash on cash: -0.74%

Traditional cash on cash: 0.87%

Airbnb Rental Income: $1178

Traditional Rental Income: $3325

Airbnb ROI: -0.74%

Traditional ROI: 0.87%

14 Landing Lane

Southampton, NY

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

$1,449,000

Airbnb cash on cash: -0.16%

Traditional cash on cash: 0.74%

Airbnb Rental Income: $2430

Traditional Rental Income: $3055

Airbnb ROI: -0.16%

Traditional ROI: 0.74%

39 Cedar Drive

Southampton, NY

3 beds | 4 baths | N/A

$2,100,000

Airbnb cash on cash: -1.28%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $1178

Traditional Rental Income: $12789

Airbnb ROI: -1.28%