277 Surfside Dr, Riverhead, NY 11901
OFF MARKET

$29,030,200

Trulia Estimate
  • 9 Beds
  • 10,958 sqft (on 1.39 acres)

277 Surfside Dr, Riverhead, NY 11901

Est. Refi. Payment $193,767/mo*
Refinance Your Home
Currently Off Market - Sold Feb 13, 2008 for $10,000,000

Home Value

Trulia Estimate
$29M
Since last month
$14K (0%)
Since last year
Decreased$7M (-18.2%)
Since last sale
Increased$19M (+193.3%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +206% in the last 10 years
MonthEstimated value
2026
August 2026$29.33M
August 2026$29.03M
July 2026$29.35M
June 2026$28.69M
May 2026$27.72M
April 2026$27.14M
March 2026$32.28M
February 2026$30.1M
January 2026$32.06M
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
90 Sunrise Avenue, Riverhead, NY
0.05
Single-Family Home
$425,000
11/05/25
4
2
1,688
30 Fairway Ave, Riverhead, NY
0.14
Single-Family Home
$685,000
04/29/26
4
2
-
18 Tyte Drive, Riverhead, NY
0.21
Single-Family Home
$590,000
04/16/26
3
1.5
1,600
108 Maple Wood Lane, Riverhead, NY
0.50
Single-Family Home
$805,000
07/20/26
4
2.5
2,453
65 Fox Run Lane, Riverhead, NY
0.44
Single-Family Home
$737,500
03/06/26
4
2
1,671
133 Trout Brook Lane, Riverhead, NY
0.56
Single-Family Home
$780,000
04/15/26
4
2
2,301
117 Trout Brook Lane, Riverhead, NY
0.56
Single-Family Home
$757,350
04/27/26
3
2
2,156
923 E Main Street, Riverhead, NY
0.42
Single-Family Home
$575,000
06/12/26
4
2
1,248
242 Trout Brook Lane, Riverhead, NY
0.69
Single-Family Home
$835,000
06/25/26
4
2.5
2,157
202 Trout Brook Lane, Riverhead, NY
0.65
Single-Family Home
$750,000
11/21/25
3
2
1,958

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
228 Surfside Dr, Bridgehampton, NY 11932
0.00
$17,376,200
9
11.5
11,176
Off Market
3903 Amen Corners #3903, Riverhead, NY 11901
0.00
$573,200
2
2.5
1,350
Off Market
39 Blueberry C, Riverhead, NY 11901
0.00
$547,100
2
2.5
-
Off Market
36 Blueberry C #36, Riverhead, NY 11901
0.00
$517,200
2
2
1,116
Off Market
3902 Amen Corners, Riverhead, NY 11901
0.00
$597,400
2
2
1,587
Off Market
3902 Amen Corners #3902, Riverhead, NY 11901
0.00
$446,800
2
2
1,597
Off Market
P 1661 Old Country Rd #364, Riverhead, NY 11901
0.00
$495,100
2
2
1,248
Off Market
1661 Old C Pondwood Rd #364, Riverhead, NY 11901
0.00
$495,100
2
2
1,248
Off Market
1661-364 Old Country Road Pondwood #364 Road, Riverhead, NY 11901
0.00
$241,500
2
2
1,248
Recently Sold
1661-364 O'Pondwood Rd, Riverhead, NY 11901
0.00
$495,100
2
2
1,248
Off Market
A9 Ash St, Riverhead, NY 11901
0.00
$110,000
1
1
600
Foreclosure
1661 Old Country Road #84, Riverhead, NY 11901
0.00
$249,999
2
2
951
For Sale

Local Information

  • Map ViewExplore the area around 277 Surfside Dr.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
2019
Lot Size
1.39 acres
Living Area
10,958 sqft
Price/Sqft
$2,649

About this House

This single-family home is located at 277 Surfside Dr, Riverhead, NY. 277 Surfside Dr is in Riverhead, NY and in ZIP code 11901. This property has 9 bedrooms and approximately 10,958 sqft of floor space. This property has a lot size of 1.39 acres and was built in 2019.
277 Surfside Dr, Riverhead, NY 11901 is a 9 bedroom, 10,958 sqft single-family home built in 2019. It last sold for $10,000,000 on Feb 13, 2008. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $29,030,200, with a rent estimate of $3,456/month.

Home Details for 277 Surfside Dr

Property Information

Year Built
Year Built: 2019
Property Type / Style
Property Type: Single Family Home

Exterior Features

Pool
Pool

Lot Information

Lot Area: 1.39 acres

Price and Tax history

DateEventPrice
Feb 13, 2008
Source: N/A
Sold
$10,000,000

Market trends in Riverhead

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
86
5MoM

Around this home

What Locals Say about Riverhead

At least 199 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 77 % Say there's holiday spirit

  • 76 % Say yards are well-kept

  • 69 % Say it's dog friendly

  • 69 % Say parking is easy

  • 60 % Say kids play outside

  • 59 % Say it's quiet

  • 56 % Say they plan to stay for at least 5 years

  • 55 % Say there's wildlife

  • 53 % Say people would walk alone at night

  • 50 % Say streets are well-lit

  • 47 % Say neighbors are friendly

  • 45 % Say there are community events

  • 43 % Say it's walkable to restaurants

  • 39 % Say there are sidewalks

  • 39 % Say it's walkable to grocery stores

Sourced by Trulia users. Learn more about our methodology.
  • Candylure
    "The usual holiday parades, alive on 25 during the summer months. A party in the streets of downtown Riverhead. "
    0
    Flag
  • Marthos P.
    "Riverhead is an up and coming neighborhood. This town has made a lot of upgrades and is cleaned up quite a bit from the Riverhead I remember as a kid."
    6
    Flag
  • Christine K.
    "Polar opposite experiences from when you enter downtown Riverhead, which is not to be considered as safe as communities closer to the other side of town ... where many neighborhoods and developments are located up and down Sound Avenue ... and just blocks from a handful of public and private beaches overlooking the beautiful Long Island Sound. "
    15
    Flag
  • Fredyacampos22
    "It’s kinda lonely but safe people it’s nice but the bus service it’s not that easy sings and bus stops not well located but there’s nice lakes nearby "
    4
    Flag
  • Kollshay24
    "My commute is very short, I don’t ave a hard time getting to and from work and shops. Pretty convenient for me"
    3
    Flag
  • Fauxfoe
    "There aren’t many sidewalks in a lot of areas. There are also tons of deer, and lots of hunters. Ticks are also an issue."
    0
    Flag
  • Donnacooke23
    "I work in the town of Riverhead. Shopping, schools, and easy access to major roads to travel such as Sunrise and the expressway"
    3
    Flag
  • Tabithabrunskill123
    "I’ve lived here all my life and it’s pretty much close knit and friendly and everyone takes care of each other"
    3
    Flag
  • Kattibattaglia
    "There are lots of dog friendly public spaces and outdoor restaurants. Safe streets for walking your pup"
    2
    Flag
  • BayViewPinesResident
    "Bay View Pines is a hidden gem in the Town of Southampton. It is a quiet, peaceful community-minded neighborhood with its own bay beach, good neighbors and easy access to both the North & the South Forks. It is located in Flanders which is the proud home of the Big Duck!"
    7
    Flag
  • Christine K.
    "The area is going through a transition for the better — downtown Riverhead is becoming more popular for both young kids, teens .... and adult age groups. Main street is now lined with popular restaurants and bars all along the Riverwalk, which is a great place to go for a walk / people watch / stroll around with Ralphs! "
    0
    Flag
  • Michelle878 a.
    "The school is district is great and the neighbors are friendly. There are many restaurants, malls, grocery stores and fun places for kids to learn and grow."
    1
    Flag
  • Mike C.
    "Flanders does not include garbage pickup. Be prepared to pay for private company or cart garbage back to the city. "
    1
    Flag
  • jimmyb11957
    "Live in an over 55 community. Very nice close to entertainment, restaurants shopping wineries and beaches. "
    0
    Flag
  • Coachcasas
    "only lived here temporarily for a year but neighbors are friendly. They walk their dogs & jog around safely. Shopping, wineries & restaurants are nearby."
    0
    Flag
  • 2 D. W. L.
    "Riverhead has several golf courses, numerous vineyards and restaurants. The family will enjoy Atlantis aquarium and Splish Splash. There is plenty of shopping at downtown riverhead and Tanger Mall. There are several equestrian centers as well."
    0
    Flag
  • ally4
    "There is a lot of crime in this neighborhood ,loud music and in the summer all of it gets worst. It's not an easy place to walk around at night and the cops are always around"
    0
    Flag
  • Bob P.
    "Live here and work this area and a 20 mile radius as an real estate broker"
    3
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 277 Surfside Dr

  • What is 277 Surfside Dr estimated to be worth?
    Trulia's estimated value for 277 Surfside Dr in Riverhead, NY is $29,030,200.
  • What is the price history for 277 Surfside Dr?
    277 Surfside Dr in Riverhead, NY last sold for $10,000,000 in February 2008.
  • Is Riverhead a buyer's or seller's market?
    Riverhead is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Riverhead?
    Residents describe Riverhead, NY as well-kept, dog-friendly, and easy to park in. Most residents say you need a car. See recently sold homes in Riverhead, NY.
  • Does 277 Surfside Dr have a pool?
    Yes, 277 Surfside Dr in Riverhead, NY has a pool.
  • How big is the lot at 277 Surfside Dr?
    The lot at 277 Surfside Dr in Riverhead, NY is about 1.4 acres.

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