21 Surfside Dr, Bridgehampton, NY 11932
NOT ACTIVE

21 Surfside Dr
Bridgehampton, NY 11932

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

$34,788,600

Trulia Estimate
as of Jun 25, 2026
Est. Refi. Payment $223,621/mo*
Refinance Your Home

$34,788,600

Trulia Estimate
as of Jun 25, 2026
Est. Refi. Payment $223,621/mo*
Refinance Your Home
5 Beds
8.5 Baths
6,516 sqft
(on 2.44 acres)

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

Description

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
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
This property is off market or not active on Trulia

Home Highlights

Parking
None
Outdoor
Pool
HOA
None
Price/Sqft
No Info
Listed
92 days ago

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

Price History for 21 Surfside Dr

DatePriceEventSource
05/13/2026$640,000ListingRemovedZillow Rentals
03/24/2026$640,000Listed For RentZillow Rentals
06/10/2025$600,000ListingRemovedZillow Rentals
02/08/2025$600,000Listed For RentZillow Rentals
08/04/2024ListingRemovedZillow Rentals
03/27/2024$660,000PriceChange
Zillow Rentals
03/19/2024$400,000Listed For RentZillow Rentals
01/01/2024ListingRemovedZillow Rentals
05/23/2023$740,000PriceChange
Zillow Rentals
04/20/2023$433,333Listed For RentZillow Rentals
01/29/2021ListingRemovedOut East
10/09/2020$400,000Listed For RentAgent Provided
06/06/2008$3,933,820Sold
N/A
03/17/2004$4,500,000Sold
N/A
05/26/1995$1,200,000Sold
N/A

Market trends in Bridgehampton

Last updated May 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
35
5MoM
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Property Tax and Assessment

Year2025
Tax
Assessment$24,563,600
Home facts updated by county records

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
79 Surfside Dr, Bridgehampton, NY
0.12
Single-Family Home
$28,000,000
11/18/25
4
3
2,004
1 Mecox Field Ln, Water Mill, NY
0.69
Single-Family Home
$8,300,000
02/03/26
4
4.5
4,000
946 Ocean Rd, Bridgehampton, NY
0.68
Single-Family Home
$10,300,000
04/24/26
6
4
3,000
104 Quimby Ln, Bridgehampton, NY
0.60
Single-Family Home
$22,150,000
04/28/26
8
11
12,500
1 Mecox Fields Ln, Bridgehampton, NY
0.69
Single-Family Home
$8,300,000
03/05/26
4
3
3,468
72 Mecox Fields Ln, Bridgehampton, NY
0.74
Single-Family Home
$6,100,000
10/01/25
5
4
3,000
400 Jobs Ln, Water Mill, NY
0.55
Single-Family Home
$7,100,000
01/13/26
3
3.5
3,000
735 Ocean Rd, Water Mill, NY
1.02
Single-Family Home
$20,000,000
03/19/26
6
6
6,563
43 Sandune Ct, Sagaponack, NY
1.15
Single-Family Home
$7,750,000
08/18/25
5
4.5
5,000

Nearby homes

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Assigned Schools

These are the assigned schools for 21 Surfside Dr.

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
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  • 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
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Apartments for Rent

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Homes for sale near 21 Surfside Dr

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Off Market Homes Near 21 Surfside Dr

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21 Surfside Dr, Bridgehampton, NY 11932 is a 5 bedroom, 9 bathroom, 6,516 sqft single-family home. This property is not currently available for sale. 21 Surfside Dr was last sold on Jun 6, 2008 for $3,933,820 (515% higher than the asking price of $640,000). The current Trulia Estimate for 21 Surfside Dr is $34,788,600.