Dream Homes

The 5 Most Expensive Hamptons Homes Listed in May

Summer is finally here, which means weekends will be spent lying by the pool or on the fabulous East End beaches. It also means there will be lots of open houses to attend. To be precise, 203 homes were added to the Hamptons real estate market in May. We decided to look into the five most expensive homes listed, which start at $13.75 million and go up to $29.5 million.

And while we are focusing on the priciest listings in May, there are plenty of Hamptons properties along all price points and well under eight figures on Out East. 

Puffin Hall at 365 & 385 South Main Street

Two homes in one? It makes sense why this was the most expensive property added this month. The two residences are completely separate, but come together seamlessly with lovely gardens and a pool centered between them. And the $30 million price tag could be well worth it for someone looking for an entirely separate space from their in-laws.

Price
$29,500,000
Area Southampton
Bed
10
Bath
9
Acres
4
SQ. FT.
9.22K

Two homes in one? It makes sense why this was the most expensive property added this month. The two residences are completely separate, but come together seamlessly with lovely gardens and a pool centered between them. And the $30 million price tag could be well worth it for someone looking for an entirely separate space from their in-laws.

412 Beachcomber Ln

This beautifully designed home was featured in Architectural Digest and other high-end glossy magazines and is asking $18 million. The property has incredible outdoor space, complete with a heated gunite pool, plenty of lounge space, a sunken tennis court and a rooftop deck.

Price
$17,999,000
Area Southampton
Bed
6
Bath
7
Acres
1.8
SQ. FT.
11K

This beautifully designed home was featured in Architectural Digest and other high-end glossy magazines and is asking $18 million. The property has incredible outdoor space, complete with a heated gunite pool, plenty of lounge space, a sunken tennis court and a rooftop deck.

12 Pudding Hill Ln

This expansive 6-bedroom home sprawls across 2.5 acres and has room to accommodate yet another principal dwelling. Currently, the property offers a brand-new pool house in addition to the recently renovated main house.

Price
$13,995,000
Area East Hampton
Bed
6
Bath
6
Acres
2.5
SQ. FT.

This expansive 6-bedroom home sprawls across 2.5 acres and has room to accommodate yet another principal dwelling. Currently, the property offers a brand-new pool house in addition to the recently renovated main house.

65 Sandpiper Ln

Be the first to live in this ultra-modern beauty in Bridgehampton located just two streets up from the beach. While the home is still under construction, we can tell from the floor plan that this will truly be a modern paradise, complete with a gym, roof deck, an elevator and a dedicated wine closet. Talk about house goals!

Price
$13,900,000
Area Bridgehampton
Bed
8
Bath
9
Acres
0.9
SQ. FT.
7.63K

Be the first to live in this ultra-modern beauty in Bridgehampton located just two streets up from the beach. While the home is still under construction, we can tell from the floor plan that this will truly be a modern paradise, complete with a gym, roof deck, an elevator and a dedicated wine closet. Talk about house goals!

6 Calf Creek Ct

Rounding out our top five is this Hamptons classic in Water Mill. The high ceilings and bright, airy design give this home an elegant, modern touch without losing its warm and cozy vibe. The property sits adjacent to a 9.9-acre agricultural reserve, which ensures privacy.

Price
$13,750,000
Area Water Mill
Bed
7
Bath
8
Acres
1.2
SQ. FT.
10.6K

Rounding out our top five is this Hamptons classic in Water Mill. The high ceilings and bright, airy design give this home an elegant, modern touch without losing its warm and cozy vibe. The property sits adjacent to a 9.9-acre agricultural reserve, which ensures privacy.


Inspired to find your next home on the East End? Search Out East for rental and sale properties in the Hamptons and North Fork.

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