20 Skipper Dr, West Islip, NY 11795
Property image
Property image
OFF MARKET

$1,485,600

Trulia Estimate
  • 6 Beds
  • 4 Baths
  • 3,702 sqft (on 0.25 acres)

20 Skipper Dr, West Islip, NY 11795

Est. Refi. Payment $9,869/mo*
Refinance Your Home
Currently Off Market - Sold Jul 26, 2017 for $792,500

Home Value

Trulia Estimate
$1.49M
Since last month
Decreased$29K (-1.9%)
Since last year
Increased$82K (+5.8%)
Since last sale
Increased$690K (+87.1%)
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 +86% in the last 10 years
MonthEstimated value
2026
August 2026$1.48M
August 2026$1.48M
July 2026$1.51M
June 2026$1.49M
May 2026$1.43M
April 2026$1.38M
March 2026$1.39M
February 2026$1.38M
January 2026$1.34M
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
22 Viking Drive, West Islip, NY
0.11
Single-Family Home
$1,400,000
04/03/26
6
2.5
3,560
11 Dolphin Lane, West Islip, NY
0.19
Single-Family Home
$1,725,000
07/20/26
4
3
3,061
10 Gate Lane, West Islip, NY
0.45
Single-Family Home
$850,000
12/18/25
7
3
3,055
128 Pace Drive S, West Islip, NY
0.25
Single-Family Home
$1,599,000
08/31/26
4
3.5
2,987
10 Mariners Circle, West Islip, NY
0.38
Single-Family Home
$875,000
05/06/26
4
2.5
2,533
133 Pace Drive S, West Islip, NY
0.28
Single-Family Home
$1,500,000
09/30/25
4
2.5
2,930
159 Driftwood Drive, West Islip, NY
0.43
Single-Family Home
$1,200,000
08/06/26
4
2.5
2,620
537 Bay 5th Street, West Islip, NY
0.65
Single-Family Home
$780,000
09/18/25
5
3
2,534
10 Carolee Court, West Islip, NY
0.38
Single-Family Home
$1,250,000
08/06/26
5
2.5
2,593
811 W Bay Drive, West Islip, NY
0.55
Single-Family Home
$850,000
10/15/25
5
2.5
1,725

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
16 Skipper Drive, West Islip, NY 11795
0.02
$1,166,200
4
2.5
-
Off Market
14 Piper Court, West Islip, NY 11795
0.05
$1,794,400
4
2.5
-
Off Market
35 Skipper Drive, West Islip, NY 11795
0.07
$1,234,500
4
3.5
2,441
Off Market
18 Piper Court, West Islip, NY 11795
0.07
$1,498,000
4
3
-
Off Market
23 Viking Drive, West Islip, NY 11795
0.08
$1,399,700
4
2.5
-
Off Market
120 Anchorage Drive, West Islip, NY 11795
0.09
$1,331,800
5
3
-
Off Market
4 Cutter Court, West Islip, NY 11795
0.10
$1,083,200
4
2.5
-
Off Market
22 Viking Drive, West Islip, NY 11795
0.11
$1,400,000
6
2.5
3,560
Recently Sold
135 Anchorage Drive, West Islip, NY 11795
0.12
$1,026,500
4
2.5
-
Off Market
115 Anchorage Drive, West Islip, NY 11795
0.13
$1,068,100
5
3
2,400
Off Market
94 Anchorage Drive, West Islip, NY 11795
0.13
$1,667,000
4
2.5
-
Off Market
35 Piper Ct, West Islip, NY 11795
0.13
$3,532,700
5
3.5
6,200
Off Market

Local Information

  • Map ViewExplore the area around 20 Skipper Dr.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1966
0.25 acre lot
3,702 sqft
$401/sqft

About this House

Welcome to this spacious and versatile 6-bedroom waterfront home nestled in one of West Islip’s most sought-after neighborhoods. Enjoy true waterfront living with a 40-foot bulkhead offering canal access just moments from the Great South Bay. Soak in panoramic bay views and unforgettable sunsets from the comfort of your own backyard oasis. Entertain in style with a large in-ground pool, surrounded by elegant pavers, and ample patio space perfect for gatherings or quiet relaxation. Perfectly designed for multi-generational living or extended family, with private entrances and flexible living spaces it is ideal for in-laws or guests. The basement adds additional storage, recreation space, or the potential for a home office or gym. This home combines functionality with luxury, all set in a prime location close to parks, beaches, and top-rated schools. A rare opportunity to own a waterfront property that offers both lifestyle and flexibility. Don't miss this one!!!
20 Skipper Dr, West Islip, NY 11795 is a 6 bedroom, 5 bathroom, 3,702 sqft single-family home built in 1966. It last sold for $792,500 on Jul 26, 2017 (43% below the $1,399,999 asking price). More recently, it was listed as a rental in April 2015 with an asking price of $2,400 per month. That rental listing was removed on May 12, 2015. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $1,485,600, with a rent estimate of $6,041/month.
Contact this Building
Property Website

Home Details for 20 Skipper Dr

Interior Features

Heating & Cooling
Heating: Natural GasAir ConditioningCooling System: Central AirHeating Fuel: Natural Gas

Property Information

Year Built
Year Built: 1966
Property Type / Style
Property Type: Single Family Home

Media

See Virtual Tour: http://.exitrealty.com/listing-tour/nyonekey:864822

Lot Information

Lot Area: 10890 sqft

Price and Tax history

DateEventPrice
Jun 16, 2025
Source: Exit Realty #864822
ListingRemoved
$1,399,999
May 20, 2025
Source: OneKey® MLS as distributed by MLS GRID #864822
Listed For Sale
$1,399,999
Apr 12, 2025
Source: Exit Realty #826612
ListingRemoved
$1,325,000
Apr 2, 2025
Source: OneKey® MLS as distributed by MLS GRID #826612
PriceChange
$1,499,990
Price increased by 13%
Mar 20, 2025
Source: Exit Realty #826612
PriceChange
$1,325,000
Price decreased by 17%

Market trends in West Islip

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
51
8MoM

Around this home

What Locals Say about West Islip

At least 219 Trulia users voted on each feature.

  • 94 % Say parking is easy

  • 92 % Say car is needed

  • 92 % Say yards are well-kept

  • 90 % Say it's dog friendly

  • 84 % Say there's holiday spirit

  • 83 % Say people would walk alone at night

  • 68 % Say kids play outside

  • 67 % Say they plan to stay for at least 5 years

  • 65 % Say it's quiet

  • 64 % Say streets are well-lit

  • 63 % Say neighbors are friendly

  • 54 % Say there are sidewalks

  • 50 % Say it's walkable to grocery stores

  • 49 % Say it's walkable to restaurants

  • 47 % Say there are community events

  • 42 % Say there's wildlife

Sourced by Trulia users. Learn more about our methodology.
  • Helene Mendez
    "It’s a great place to raise a family. "
    0
    Flag
  • Amanda Bertolini
    "Lived here for three years. Lots of young families. Neighborhood is kept very clean and has great schools. "
    0
    Flag
  • Kelley S.
    "We love our community! My kids are involved with different sports and have more friends then I ever did growing up! "
    0
    Flag
  • Trulia User
    "There aren’t many dog dedicated spaces, like dog parks, agility areas and many apartment complexes have long lists of breed restrictions. "
    1
    Flag
  • Trulia User
    "The nearby Good Samaritan hospital medical center is close but not as good as other hospitals on the island"
    0
    Flag
  • Trulia User
    "You see some dogs being walked daily, and there are schools near by with plenty of fields for the dogs to run. There is also a dog park one town over. "
    1
    Flag
  • Trulia User
    "I see people walking their dogs all the time around the neighborhood. A lot of them are all really friendly and love to have you stop and pet them! "
    0
    Flag
  • Erica B.
    "Great neighborhood very safe. Great schools! You can’t go wrong living in any part of west islip. Super clean and lots to do. Just a short walk to babylon village which has many restaurants and shops. Love this area and have loved here for 15 years and will live here the rest of my life. "
    10
    Flag
  • Cesimmons014
    "I’ve grown up in this neighborhood my entire life, I am now raising my own family here. It’s a great, safe town "
    4
    Flag
  • Colcolwalsh
    "I live in this neighborhood for 23 years. It has a great school district. Great sports programs! Close to the beach, and marina. Perfect for families. "
    7
    Flag
  • 6shomeimprovements
    "nice area great place for children and a nice safe neighborhood close too many major highways and South Shore Beach"
    3
    Flag
  • Kevin H.
    "Easy to get here. Not too much traffic. Plenty of places to eat and shop. Friendly and quiet neighborhood "
    2
    Flag
  • Brendon P.
    "Lives here when I was younger and moved back about 4 years ago. Might wind up staying around. I like the stores and places to eat and neighbors are friendly"
    6
    Flag
  • Daniel L.
    "Wonderful and safe neighborhood and- great schools and between 2 of Long Islands most popular downtown areas "
    2
    Flag
  • Colcolwalsh
    "I’ve lived here for 22 years and everyone is very friendly and neighborly. Great schools and great sports programs for the kids. "
    4
    Flag
  • Kelsey McCarthy
    "It a pretty good area to walk your dog in good weather but it’s near a highway and there are quite a few feral cats around."
    0
    Flag
  • Wayne Smith
    "quiet streets. boating & fishing neighborhood. walk sidewalks any time day or night, safely and friendly"
    6
    Flag
  • Colcolwalsh
    "Close to local beaches and only 2 miles from the ocean. Great neighborhood with parks. Dog park near by as well. Family friendly "
    0
    Flag
  • Erica B.
    "Easy commute to anywhere you need to go. Sunrise highway and southern state super close by. Babylon train station about a mile away"
    0
    Flag
  • Barbara D.
    "This is a family neighborhood in every sense. Really safe and community oriented. Good schools. The epitome of suburbia. "
    0
    Flag
  • Colcolwalsh
    "Good friendly neighborhood with lots of kids, decent schools. Very low crime. Great community. Restaurants and some shopping near by. "
    0
    Flag
  • Colcolwalsh
    "It is a great town with lots of great people. School district is good. Restaurants in town and near by. Near Babylon train station. "
    0
    Flag
  • Teresa
    "I see a lot of people walking all different kinds of dogs. But There are Not really a lot of places you can take your dog off leash."
    0
    Flag

LGBTQ Local Legal Protections

Frequently asked questions about 20 Skipper Dr

  • What is 20 Skipper Dr estimated to be worth?
    Trulia's estimated value for 20 Skipper Dr in West Islip, NY is $1,485,600.
  • What is the price history for 20 Skipper Dr?
    20 Skipper Dr in West Islip, NY last sold for $792,500 in July 2017.
  • Is West Islip a buyer's or seller's market?
    West Islip is currently a seller's market, based on recent for-sale activity.
  • What do residents say about West Islip?
    Residents describe West Islip, NY as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in West Islip, NY.
  • Does 20 Skipper Dr have air conditioning?
    Yes, 20 Skipper Dr in West Islip, NY has air conditioning.
  • How big is the lot at 20 Skipper Dr?
    The lot at 20 Skipper Dr in West Islip, NY is about 0.25 acres (10,890 sq ft).

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