558 Pleasure Drive, Riverhead, NY 11901
OFF MARKET

$1,155,600

Trulia Estimate
  • 4 Beds
  • 3 Baths
  • 2,893 sqft (on 1.75 acres)

558 Pleasure Drive, Riverhead, NY 11901

Est. Refi. Payment $7,694/mo*
Refinance Your Home
Currently Off Market - Sold Sep 10, 2024 for $975,000

Home Value

Trulia Estimate
$1.16M
Since last month
Decreased$10K (-0.8%)
Since last year
Increased$119K (+11.5%)
Since last sale
Increased$179K (+18.3%)
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 +90% in the last 10 years
MonthEstimated value
2026
August 2026$1.15M
August 2026$1.15M
July 2026$1.16M
June 2026$1.17M
May 2026$1.13M
April 2026$1.13M
March 2026$1.09M
February 2026$1.07M
January 2026$1.05M
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
518 Maple Avenue S, Flanders, NY
0.61
Single-Family Home
$765,000
12/11/25
3
2
1,232
707 Pleasure Drive, Flanders, NY
0.37
Single-Family Home
$1,325,000
12/22/25
2
2
1,500
799 Pleasure Drive, Flanders, NY
0.57
Single-Family Home
$659,900
10/21/25
3
2
1,290
5 Arthur Street, Flanders, NY
0.76
Single-Family Home
$850,000
08/12/26
4
2.5
1,534
484 Brookhaven Avenue, Riverhead, NY
0.81
Single-Family Home
$799,000
04/23/26
5
3
2,266
38 Pleasure Drive, Flanders, NY
1.11
Single-Family Home
$800,000
08/28/26
3
3
1,600
28 & 34 Townsend Avenue, Riverhead, NY
1.10
Single-Family Home
$825,000
06/22/26
3
2
1,919
343 Oak Avenue, Flanders, NY
1.05
Single-Family Home
$750,000
06/29/26
4
2.5
1,700

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
575 Pleasure Drive, Flanders, NY 11901
0.18
-
-
-
-
Off Market
707 Pleasure Drive, Flanders, NY 11901
0.37
$1,325,000
2
2
1,500
Recently Sold
799 Pleasure Drive, Flanders, NY 11901
0.57
$692,700
3
2
1,290
Off Market
518 Maple Avenue S, Flanders, NY 11901
0.61
$765,000
3
2
1,232
Recently Sold
510 Maple Avenue, Flanders, NY 11901
0.63
$960,900
4
2.5
1,700
Off Market
491 Maple Avenue, Flanders, NY 11901
0.64
$840,300
4
2.5
-
Off Market
220 Pleasure Dr, Flanders, NY 11901
0.68
$1,497,000
3
3
2,860
For Sale
72-72 Risa Ct, Riverhead, NY 11901
0.75
$888,200
3
3
2,198
Off Market
442 Maple Avenue, Flanders, NY 11901
0.72
$860,600
4
2.5
-
Off Market
72 Risa Ct, Riverhead, NY 11901
0.78
$911,800
3
3
2,198
Off Market
917 N Pleasure Drive, Riverhead, NY 11901
0.78
$799,600
3
1.5
-
Off Market

Local Information

  • Map ViewExplore the area around 558 Pleasure Drive.
  • Schools1 Preschool School2 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1987
1.75 acre lot
2,893 sqft
$399/sqft

About this House

Gorgeous home located on renowned Pleasure Drive. Down a long driveway enter into this magical property with complete privacy. Lovely almost two acres with additional, separate parking lot is practically hidden by luscious growth of trees, and shrubs. If you want peace and quiet, you will find it here. There is an in deck pool with a screened in porch area for outdoor entertaining. This four bedroom, three bath home has relaxed living conditions with many entertaining spaces. Luxury is abounded with the gourmet chef's kitchen, large living room with fireplace, expansive sunroom created for relaxation and enjoying the beautiful outdoor views. There is an ensuite bedroom plus two additional guest bedrooms and a bath on main floor as well. The upper level is dedicated to the oversized primary suite with sitting area and private bath. This is a property you don't want to miss!!, Additional information: Appearance:mint,Separate Hotwater Heater:y
558 Pleasure Drive, Riverhead, NY 11901 is a 4 bedroom, 3 bathroom, 2,893 sqft single-family home built in 1987. It last sold for $975,000 on Sep 10, 2024 (2% below the $999,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,155,600, with a rent estimate of $6,498/month.
Last check for updates: about 5 hours ago
Listed by Anne Marie Francavilla
Douglas Elliman Real Estate, (631) 723-2721
Constance Porto, (917) 731-4317
Douglas Elliman Real Estate, (631) 723-2721
Bought with: Doris F. Lucero, (631) 488-5393, New Vision Group Realty Inc, (917) 913-7116
Source: OneKey® MLS as distributed by MLS GRID, MLS#L3504843

Home Details for 558 Pleasure Drive

Interior Features

Interior Details
Basement: UnfinishedNumber of Rooms: 9
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2893 Square Feet
Appliances & Utilities
Utilities: Trash Collection PrivateAppliances: Dishwasher, Dryer, ENERGY STAR Qualified Appliances, Microwave, Oven, Refrigerator, Washer, Oil Water HeaterDishwasherDryerMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Forced Air,OilHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Forced Air
Fireplace & Spa
Number of Fireplaces: 1No Spa
Gas & Electric
Electric: Generator
Windows, Doors, Floors & Walls
Window: Double Pane Windows, Skylight(s)Flooring: Carpet, Hardwood
Levels, Entrance, & Accessibility
Levels: TwoFloors: Carpet, Hardwood
Security
Security: Security Gate, Security System

Exterior Features

Exterior Home Features
Patio / Porch: Deck, PorchExterior: Private EntranceHas a Private Pool
Parking & Garage
No CarportParking: Attached,Private
Pool
Pool: In GroundPool
Frontage
Responsible for Road Maintenance: Public Maintained Road
Water & Sewer
Sewer: Septic Tank

Property Information

Year Built
Year Built: 1987Year Renovated: 1996
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Post Modern
Building
Construction Materials: Vinyl SidingNot Attached Property
Property Information
Condition: ActualParcel Number: 0900201000100012000

Price & Status

Price
List Price: $999,000
Status Change & Dates
Off Market Date: Fri Mar 08 2024

Active Status

MLS Status: Sold

Location

Direction & Address
City: Flanders
School Information
Elementary School: Phillips Avenue SchoolJr High / Middle School: Riverhead Middle SchoolHigh School: Riverhead Senior High SchoolHigh School District: Riverhead

Building

Building Area
Building Area: 2893 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 1.7452 Acres

Offer

Listing Agreement Type: Exclusive Right To Lease

Miscellaneous

BasementMls Number: L3504843Attic: ScuttleShowing Requirements: Call Listing Office

Price and Tax history

DateEventPrice
Sep 10, 2024
Source: N/A
Sold
$975,000
Jun 12, 2024
Source: OneKey® MLS as distributed by MLS GRID #L3504843
Sold
$975,000
Mar 8, 2024
Source: OneKey® MLS as distributed by MLS GRID #3504843
Pending
$999,000
Oct 26, 2023
Source: OneKey® MLS as distributed by MLS GRID #3504843
PriceChange
$999,000
Price decreased by 17%
Sep 17, 2023
Source: OneKey® MLS as distributed by MLS GRID #3504843
Listed For Sale
$1,199,000

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

Based on information submitted to the MLS GRID as of 2026-09-07 15:13:03 PDT All data is obtained from various sources and may not have been verified by broker or MLS GRID. Supplied Open House Information is subject to change without notice. All information should be independently reviewed and verified for accuracy. Properties may or may not be listed by the office/agent presenting the information. Some IDX listings have been excluded from this website. Click here for more information

Frequently asked questions about 558 Pleasure Drive

  • What is 558 Pleasure Drive estimated to be worth?
    Trulia's estimated value for 558 Pleasure Drive in Riverhead, NY is $1,155,600.
  • What is the price history for 558 Pleasure Drive?
    558 Pleasure Drive in Riverhead, NY last sold for $975,000 in September 2024.
  • 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 558 Pleasure Drive have air conditioning?
    Yes, 558 Pleasure Drive in Riverhead, NY has air conditioning.
  • Does 558 Pleasure Drive have a pool?
    Yes, 558 Pleasure Drive in Riverhead, NY has a pool.

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