Insights

The 5 Most Expensive Hamptons Homes Listed in October

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Every month on Heading Out, we take a look at the five most expensive new listings to come on the market. With the rush of peak season officially over, October is a great time to begin hunting for the perfect Hamptons home. An off-season purchase has significant advantages, allowing buyers time to renovate, decorate and landscape before the start of the summer. Ambitious buyers could potentially even be settled in by the holidays.

On this list of the most expensive Hamptons homes listed in October, price tags start at nearly $10 million and go all the way up to $37.5 million. While those figures are significantly higher than the current Hamptons-wide median of $2 million, the homes themselves are nothing short of stunning. Tell us your favorite in the comments.

359 Meadow Ln

At $37.5 million, this enormous estate on prestigious Meadow Lane is the most expensive home to hit Out East this month by more than $20 million. We’re loving its secluded vibes and waterfront access. Since it’s located next to protected land, buyers will never have to worry about noise from the neighbors or new construction blocking the views.

Price
$37,500,000
Area Southampton
Bed
5
Bath
5
Acres
5.53
SQ. FT.
6.19K

At $37.5 million, this enormous estate on prestigious Meadow Lane is the most expensive home to hit Out East this month by more than $20 million. We’re loving its secluded vibes and waterfront access. Since it’s located next to protected land, buyers will never have to worry about noise from the neighbors or new construction blocking the views.

6 Dannielles Way

If “more” is what you’re going for, look no further. As if 21 acres of land weren’t enough, the second-most expensive home on our list boasts more 13,000 square feet of living space, complete with 8 bedrooms and 10 bathrooms. We can already envision the summer parties we’d throw in the expansive outdoor living area. The Hamptons pedigree at this property is real — the grounds are currently being used as a polo field. Buyers can also use the land for agricultural or equestrian structures.

Price
$14,995,000
Area Bridgehampton
Bed
8
Bath
10
Acres
21.16
SQ. FT.
13K

If “more” is what you’re going for, look no further. As if 21 acres of land weren’t enough, the second-most expensive home on our list boasts more 13,000 square feet of living space, complete with 8 bedrooms and 10 bathrooms. We can already envision the summer parties we’d throw in the expansive outdoor living area. The Hamptons pedigree at this property is real — the grounds are currently being used as a polo field. Buyers can also use the land for agricultural or equestrian structures.

422 Dune Rd

The third-most expensive home on our list comes with less living space and a smaller amount of land than the first two homes, but it is surrounded by water, with the Atlantic Ocean on one side and Mecox Bay on the other. The huge windows of this modern home let in breathtaking views. But buyers will want to make sure to invest in window dressings, especially for the master suite. That sun rises early in the summer.

Price
$12,950,000
Area Bridgehampton
Bed
4
Bath
4
Acres
1.8
SQ. FT.
3.5K

The third-most expensive home on our list comes with less living space and a smaller amount of land than the first two homes, but it is surrounded by water, with the Atlantic Ocean on one side and Mecox Bay on the other. The huge windows of this modern home let in breathtaking views. But buyers will want to make sure to invest in window dressings, especially for the master suite. That sun rises early in the summer.

270 Ox Pasture Rd

We are loving the classic exterior of this turn-of-the-century home located in the heart of Southampton Village. At $10.4 million, it’s the fourth-most expensive home listed on Out East this month. It’s full of character, including stained glass inserts in the third-floor walls. But our favorite detail? The hidden wine cellar on the first floor.

Price
$9,950,000
Area Southampton
Bed
8
Bath
4
Acres
2.7
SQ. FT.
4.06K

We are loving the classic exterior of this turn-of-the-century home located in the heart of Southampton Village. At $10.4 million, it’s the fourth-most expensive home listed on Out East this month. It’s full of character, including stained glass inserts in the third-floor walls. But our favorite detail? The hidden wine cellar on the first floor.

87 Oliver's Cove Ln

Rounding out our list this month is a brand-new home located south of the highway in Water Mill for just shy of $10 million. With 6,400 square feet of living space, including 8 bedrooms, the future owner of this home will be more than ready to host the whole family for the upcoming holiday season. Thankfully, there are 9 bathrooms, too. Blueprints for the home show a ton of outdoor space, making this home a fantastic summer getaway as well.

Price
$9,995,000
Area Water Mill
Bed
8
Bath
9
Acres
0.94
SQ. FT.
6.4K

Rounding out our list this month is a brand-new home located south of the highway in Water Mill for just shy of $10 million. With 6,400 square feet of living space, including 8 bedrooms, the future owner of this home will be more than ready to host the whole family for the upcoming holiday season. Thankfully, there are 9 bathrooms, too. Blueprints for the home show a ton of outdoor space, making this home a fantastic summer getaway as well.


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