21 Surfside Dr, Bridgehampton, NY 11932
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NOT ACTIVE

21 Surfside Dr
Bridgehampton, NY 11932

  • 5 Beds
  • 8.5 Baths
  • 6,516 sqft (on 2.44 acres)

$34,862,300

Trulia Estimate
as of Aug 21, 2026

$34,862,300

Trulia Estimate
as of Aug 21, 2026
  • 5 Beds
  • 8.5 Baths
  • 6,516 sqft (on 2.44 acres)

Home Highlights

Property Type
Single-Family Home
Lot Size
2.44 acres
Living Area
6,516 sqft
Price/Sqft
$5,350
Parking
None

Local Information

  • Map ViewExplore the area around 21 Surfside Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

About this House

Rental Registration #: RP230704 Welcome to your own private oceanfront oasis in the heart of Bridgehampton on coveted Surfside Drive. This stunning property set on 2.4+/- acres boasts three structures - a main house, secondary structure and pool house - all ideal for entertaining with multiple spaces to enjoy every amenity. First floor living spaces with ground floor ocean views make this property unique of its kind. Enjoy breathtaking 180 degree ocean views and water vistas throughout while maintaining ultimate serenity and privacy. The bright living room, oversized kitchen with breakfast area, and formal dining room are perfect for hosting guests. Step out onto the large mahogany wood deck with a private walkway leading to the beach for the perfect summer getaway. Upstairs, the primary suite with private terrace overlooks these same famous Hamptons beaches. There are four additional en-suite guest bedrooms. Outside, venture to the pavilion with negative edge saltwater heated gunite pool. The adjoining pool house is complete with a lounge, kitchenette, and full bath. Bluestone patio surrounds the pool, ideal for sunbathing, relaxing, and enjoying the ocean breeze. The separate secondary structure inhabits a gym, living room with kitchenette and 2 office suites, providing ample space for work and play. Don't miss out on this opportunity to make your summer memories in this breathtaking oceanfront home. Pricing: $320k/two weeks, July 1 to August 31 - $1,280,000, July 11 to Sept 10 - $1,280,000. Inquire for additional dates and pricing. Rental Registry #RP230704
21 Surfside Dr, Bridgehampton, NY 11932 is a 5 bedroom, 9 bathroom, 6,516 sqft single-family home. It last sold for $3,933,820 on Jun 6, 2008 (515% above the $640,000 asking price). More recently, it was listed as a rental in March 2026 with an asking price of $640,000 per month. That rental listing was removed on May 13, 2026. It is currently off market. The Trulia Estimate is $34,862,300, with a rent estimate of $6,749/month.

Home Details for 21 Surfside Dr

Property Information

Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Exterior Features

Pool
Pool
Parking & Garage
Parking: None

Lot Information

Lot Area: 0.00 Acres

Comparable Sales for 21 Surfside Dr

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
474 Jobs Ln, Bridgehampton, NY
0.64
Single-Family Home
$18,000,000
11/05/25
6
7
6,000 sqft
79 Surfside Dr, Bridgehampton, NY
0.12
Single-Family Home
$28,000,000
11/18/25
4
3
2,004 sqft
1 Mecox Field Ln, Water Mill, NY
0.69
Single-Family Home
$8,300,000
02/03/26
4
4.5
4,000 sqft
946 Ocean Rd, Bridgehampton, NY
0.68
Single-Family Home
$10,300,000
04/24/26
6
4
3,000 sqft
104 Quimby Ln, Bridgehampton, NY
0.60
Single-Family Home
$22,400,000
05/21/26
8
11
12,500 sqft
1 Mecox Fields Ln, Bridgehampton, NY
0.69
Single-Family Home
$8,300,000
03/05/26
4
3
3,468 sqft
72 Mecox Fields Ln, Bridgehampton, NY
0.74
Single-Family Home
$6,100,000
10/01/25
5
4
3,000 sqft
400 Jobs Ln, Water Mill, NY
0.55
Single-Family Home
$7,100,000
01/13/26
3
3.5
3,000 sqft
735 Ocean Rd, Water Mill, NY
1.02
Single-Family Home
$20,000,000
03/19/26
6
6
6,563 sqft
73 Summerfield Ln, Water Mill, NY
1.06
Single-Family Home
$6,150,000
12/09/25
4
3.5
3,000 sqft

Nearby homes

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Around this home

What Locals Say about Bridgehampton

At least 17 Trulia users voted on each feature.

  • 91 % Say yards are well-kept

  • 89 % Say car is needed

  • 88 % Say they plan to stay for at least 5 years

  • 84 % Say people would walk alone at night

  • 80 % Say parking is easy

  • 73 % Say it's dog friendly

  • 73 % Say there's wildlife

  • 71 % Say there's holiday spirit

  • 65 % Say it's walkable to restaurants

  • 64 % Say there are community events

  • 64 % Say it's quiet

  • 60 % Say it's walkable to grocery stores

  • 57 % Say neighbors are friendly

  • 42 % Say there are sidewalks

  • 38 % Say kids play outside

  • 35 % Say streets are well-lit

Sourced by Trulia users. Learn more about our methodology.
  • Randel M.
    "Ingerir here for three years and never had a problem. Everything is in close proximity from supermarkets to hardware you name it"
    0
    Flag
  • Dorettakgoldberg
    "combination of farms, beaches, private homes and upscale restaurants and shopping creates a unique and comfortable atmosphere"
    0
    Flag
  • Molly
    "Very quiet neighborhood. Walk to beach’s, kayaking 3 minutes away, grocery store 2 minutes away. Southampton school district. Walk to farm stand for your fresh organic vegetables and fruits."
    0
    Flag
  • mcaridi
    "live in the neighborhood , delightful "
    2
    Flag
  • Kathy J.
    "I bought a house here a couple of years ago and I find the area to be lovely and convenient. We wanted something within walking distance to town, yet country like in setting and this is it. It is near a pond and a very short distance by car to the Atlantic Ocean beach of Sagaponac."
    0
    Flag

LGBTQ Local Legal Protections

Price and Tax history

DateEventPrice
May 13, 2026
Source: Zillow Rentals
ListingRemoved
$640,000
Mar 24, 2026
Source: Zillow Rentals
Listed For Rent
$640,000
Jun 10, 2025
Source: Zillow Rentals
ListingRemoved
$600,000
Feb 8, 2025
Source: Zillow Rentals
Listed For Rent
$600,000
Aug 4, 2024
Source: Zillow Rentals
ListingRemoved
This property is off market or not active on Trulia

Frequently asked questions about 21 Surfside Dr

  • What is 21 Surfside Dr estimated to be worth?
    Trulia's estimated value for 21 Surfside Dr in Bridgehampton, NY is $34,862,300.
  • What is the price history for 21 Surfside Dr?
    21 Surfside Dr in Bridgehampton, NY last sold for $3,933,820 in June 2008.
  • Is Bridgehampton a buyer's or seller's market?
    Bridgehampton is currently a buyer's market, based on recent for-sale activity.
  • What do residents say about Bridgehampton?
    Residents describe Bridgehampton, NY as well-kept, established, and easy to park in. Most residents say you need a car. See recently sold homes in Bridgehampton, NY.
  • Does 21 Surfside Dr have a pool?
    Yes, 21 Surfside Dr in Bridgehampton, NY has a pool.
  • How big is the lot at 21 Surfside Dr?
    The lot at 21 Surfside Dr in Bridgehampton, NY is about 2.4 acres.

Homes for rent near 21 Surfside Dr

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.
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