39 Chestnut Street, Central Islip, NY 11722
OFF MARKET

$765,500

Trulia Estimate
  • 5 Beds
  • 3 Baths
  • 2,112 sqft (on 0.35 acres)

39 Chestnut Street, Central Islip, NY 11722

Est. Refi. Payment $5,239/mo*
Refinance Your Home
Currently Off Market - Sold Oct 29, 2025 for $730,000

Home Value

Trulia Estimate
$766K
Since last month
Increased$4K (+0.5%)
Since last year
Increased$53K (+7.5%)
Since last sale
Increased$36K (+4.9%)
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 +192% in the last 10 years
MonthEstimated value
2026
August 2026$766K
August 2026$766K
July 2026$762K
June 2026$754K
May 2026$763K
April 2026$756K
March 2026$753K
February 2026$751K
January 2026$741K
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
542 Freeman Avenue, Brentwood, NY
0.44
Single-Family Home
$710,000
03/25/26
5
2
2,168
478 Mayflower Avenue, Brentwood, NY
0.25
Single-Family Home
$900,000
07/17/26
6
3
3,000
238 Wiley Street, Brentwood, NY
0.46
Single-Family Home
$650,000
05/29/26
6
4
1,750
1295 Islip Avenue, Central Islip, NY
0.46
Single-Family Home
$760,000
10/14/25
7
3
2,200
1290 Islip Avenue, Brentwood, NY
0.48
Single-Family Home
$525,000
10/28/25
5
2
1,800
63 Ferris Avenue, Brentwood, NY
0.44
Single-Family Home
$670,000
09/04/26
4
2
1,617
5 Zane Court, Brentwood, NY
0.57
Single-Family Home
$700,000
08/28/26
5
2
1,742
1548 Spur Drive S, Islip, NY
0.73
Single-Family Home
$745,000
12/26/25
6
3
2,678
34 Peach Street, Central Islip, NY
0.16
Single-Family Home
$350,000
06/01/26
2
2
1,955

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
28 Chestnut Street, Central Islip, NY 11722
0.09
$888,100
8
4
-
Off Market
61 Chestnut Street, Brentwood, NY 11717
0.09
$656,600
4
2
2,400
Off Market
34 Peach Street, Central Islip, NY 11722
0.16
$549,000
2
2
1,955
For Sale
62 Sycamore Street, Brentwood, NY 11717
0.21
$732,100
6
2
-
Off Market
14 Pear Street, Central Islip, NY 11722
0.21
$730,100
5
2
-
Off Market
892 Islip Avenue, Brentwood, NY 11717
0.16
$729,000
4
2
-
Off Market
23 Peach Street, Central Islip, NY 11722
0.24
$740,100
5
3
1,900
Off Market
10 Peach St, Central Islip, NY 11722
0.26
$730,900
3
2
21,780
Off Market
339 E Locust Street, Central Islip, NY 11722
0.23
$551,500
2
1
-
Off Market
6 Chestnut Street, Central Islip, NY 11722
0.24
$669,000
3
2
-
Off Market
434 Locust Street, Brentwood, NY 11717
0.21
$788,900
6
2
2,400
Off Market

Local Information

  • Map ViewExplore the area around 39 Chestnut Street.
  • Schools1 Preschool School3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Single-Family Home
Built in 1966
0.35 acre lot
2,112 sqft
$362/sqft
Garage

About this House

Welcome to 39 Chestnut St! This luxurious expanded ranch is designed with a Hamptons splash! The striking white and black brick exterior immediately sets this home apart from everything else in the neighborhood. No detail overlooked in this top-to-bottom transformation—featuring a brand new roof, siding, energy-efficient windows, upgraded 200-amp electrical service and plenty more. As you enter, you’re welcomed by a stunning open-concept layout adorned with gleaming hardwood floors, recessed lighting, and a cozy fireplace that adds warmth and charm. The chef’s kitchen is a true showstopper, outfitted with Samsung stainless steel appliances, quartz countertops, soft-close cabinetry, and a custom floating range hood complemented by a sleek breakfast bar—ideal for entertaining. The main level offers three generously sized bedrooms and two spa-inspired bathrooms that look straight out of a magazine. The lower level offers incredible versatility with bonus rooms, vinyl flooring, high ceilings, a full bathroom, and a private outside entrance—perfect for guests, a home office, or extended living. Potential mother/daughter with proper permits. Enjoy the convenience of a one-car garage, a gated driveway for added privacy, and an expansive corner lot with a spacious backyard and side yard—offering more land than your typical property. This is not your average flip—it’s a thoughtfully curated home ready to welcome its next proud owner. Located just minutes from major highways, shopping, and public transportation, this rare opportunity won’t last long. Your dream home awaits!
39 Chestnut Street, Central Islip, NY 11722 is a 5 bedroom, 3 bathroom, 2,112 sqft single-family home built in 1966. It last sold for $730,000 on Oct 29, 2025 (4% above the $699,000 asking price). This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $765,500, with a rent estimate of $4,524/month.
Last check for updates: about 3 hours ago
Listed by Kevin Iglesias, (631) 618-7413
Signature Premier Properties, (631) 642-2300
Sarah Fox, (631) 926-1176
Signature Premier Properties, (631) 642-2300
Bought with: Ivania Flores CBR SFR ABR SRS, (631) 433-1612, HomeSmart Dynamic Realty, (631) 291-6290
Source: OneKey® MLS as distributed by MLS GRID, MLS#892986

Home Details for 39 Chestnut Street

Interior Features

Interior Details
Basement: FullNumber of Rooms: 10
Beds & Baths
Number of Bedrooms: 5Number of Bathrooms: 3Number of Bathrooms (full): 3
Dimensions and Layout
Living Area: 2112 Square Feet
Appliances & Utilities
Utilities: Natural Gas AvailableAppliances: Stainless Steel Appliance(s)
Heating & Cooling
Heating: Has Heating Unspecified TypeNo CoolingAir Conditioning: NoneHas HeatingHeating Fuel: Has Heating Unspecified Type
Fireplace & Spa
Has a Fireplace

Exterior Features

Exterior Home Features
No Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageParking Spaces: 1Parking: Garage
Water & Sewer
Sewer: Other

Days on Market

Cumulative Days on Market: 39

Property Information

Year Built
Year Built: 1966
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Exp Ranch
Building
Not Attached Property
Property Information
Parcel Number: 0500206000200034001

Price & Status

Price
List Price: $699,000
Status Change & Dates
Off Market Date: Wed Sep 17 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: Central Islip
School Information
Elementary School: Andrew T Morrow SchoolJr High / Middle School: CHARLES A MULLIGAN ELEMENTARY SCHOOLHigh School: Central Islip Senior High SchoolHigh School District: Central Islip

Building

Building Area
Building Area: 2112 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 0.35 acres

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

BasementMls Number: 892986Attic: FullAttribution Contact: 631-642-2300Showing Requirements: Appointment Only

Price and Tax history

DateEventPrice
Oct 29, 2025
Source: OneKey® MLS as distributed by MLS GRID #892986
Sold
$730,000
Sep 18, 2025
Source: OneKey® MLS as distributed by MLS GRID #892986
Pending
$699,000
Aug 14, 2025
Source: OneKey® MLS as distributed by MLS GRID #892986
PendingToActive
$699,000
Aug 1, 2025
Source: OneKey® MLS as distributed by MLS GRID #892986
Pending
$699,000
Jul 25, 2025
Source: OneKey® MLS as distributed by MLS GRID #892986
Listed For Sale
$699,000

Market trends in Central Islip

Last updated August 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
59
4MoM

Around this home

What Locals Say about Central Islip

At least 347 Trulia users voted on each feature.

  • 85 % Say car is needed

  • 82 % Say parking is easy

  • 82 % Say yards are well-kept

  • 70 % Say it's dog friendly

  • 67 % Say there's holiday spirit

  • 58 % Say kids play outside

  • 56 % Say it's quiet

  • 56 % Say there are sidewalks

  • 51 % Say it's walkable to grocery stores

  • 48 % Say they plan to stay for at least 5 years

  • 47 % Say streets are well-lit

  • 46 % Say neighbors are friendly

  • 43 % Say it's walkable to restaurants

  • 41 % Say people would walk alone at night

  • 41 % Say there's wildlife

  • 32 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Diesumi1976
    "I work 8 minutes away so is wonderful, on the other hand my wife is 45 minutes away but is not bad at all "
    0
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  • Joel Romero
    "This is a good place to have pets , dogs must love this place , there’s a lot of open space all around."
    0
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  • Naheim S.
    "I've lived here for 13 years and it's been truly a wonderful experience, neighbors are great safety is always paramount along with 24 hour security ensuring all resident are safe. The community is always clean & updated with trees and roads, i was truly lucky to get an opportunity to live here in this luxury town-home community."
    10
    Flag
  • Trulia User
    "LIRR is nearby. Buses are nearby and usually run every hour. However, a lot of patience and walking is required if you are taking public transportation."
    0
    Flag
  • Trulia User
    "Need a car to get around. Stores around but about half mile to a mile away. Can walk but in cold days it can be hard. Close to MTA and bus. Very noisy, with other homes and people around. "
    0
    Flag
  • Trulia User
    "Very nice houses and a dog/family park. The area is very save, train station and busses as well. A very nice school system."
    0
    Flag
  • Trulia User
    "quiet and friendly people. access to many stores and public transportation. close to all major highways. "
    0
    Flag
  • Trulia User
    "ive lived in this neighborhood for 15 years! great neighborhood , neighbors are friendly , all areas are clean! has good parks for children "
    0
    Flag
  • Trulia User
    "Short and a lot of traffic all the time, many accidents and the sirens don't stop, a lot of people walking, riding bikes, picking up bottles and all kind of stuff. "
    0
    Flag
  • Williamsmario20
    "A lot of space to walk your dogs. One thing I don’t like is a lot of dog owners have faulty fences and dogs do escape. "
    2
    Flag
  • Trulia User
    "Everyone looks out for each other. College woods is on little community within itself. People say what they want until you lived here and experienced the people then you can’t comment "
    14
    Flag
  • Emmanuelrosario2122
    "Everyone is friendly and there nice and sometimes dogs get out of there houses and there dangerous breeds "
    14
    Flag
  • Keila G.
    "Typically I don’t shop in this area but I do like that when there is a quick errand I need to do I have options. I always feel safe and it’s normally quiet in the area I live in. "
    3
    Flag
  • Shebuti
    "Although it is not a safe area I haven’t faced any issues during my 5 years stay in this area. It’s not the nicest community but it is cheap. If you are living in a gated community then it is quite safe."
    5
    Flag
  • Jonitoatias
    "Central Islip is a nice, multicultural neighborhood, but you would definitely need a car if you live here..."
    4
    Flag
  • Cew318
    "I do see people walking dogs in the area. I know there are a couple of parks in the area. You can also bring your dog into the pet store. "
    1
    Flag
  • Thatsmecutie
    "School system is terrible. Child was enrolled privately at first then ultimately homeschooled when I lived there. Lots for kids to do in surrounding areas though. Library, trampoline park, etc"
    1
    Flag
  • Thatsmecutie
    "Feel pretty safe here. The peripheral area is a little sketchy still. However, the area is being built up and that will hopefully change the surrounding areas. "
    3
    Flag
  • Emmaaa515
    "I hate this area it’s gross people don’t take care of it the town is run down I can not wait to move "
    0
    Flag
  • Maudlynne A.
    "I am not sure. People own dogs around the neighborhood but i don't often see them walking their dogs. it's a spacious street to walk dogs. "
    0
    Flag
  • Maudlynne A.
    "we mind our own business. if you ask for hp you will get it. it's very very quite and comfortable. we secretly look out for each other but don't want to admit it."
    10
    Flag
  • Maudlynne A.
    "LIRR is my transportation to and from work. it is safe and punctual most of the time. it's very expensive but I work in Jamaica Queens so I have no choice. The Commute itself is smooth and relaxing."
    0
    Flag
  • Martin W.
    "College woods in central Islip is a good area. The neighbors a really nice, always looking to extend a helping hand. And a lot of them have stories for days, which will help any single or couple fit right in. "
    11
    Flag
  • Julgomez2
    "its redidential everything is changing for the good. the school are better than how they were in the past."
    6
    Flag
  • Martin W.
    "College woods is a great location to live in Central Islip. My Neighbors are fantastic and very welcoming. "
    0
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  • Bejeanntte
    "there are many families.a big shopping center many supermarkets ...good schools.railroad near us...court house ....a big stadium"
    0
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  • Ashleyn
    "it's horrible here a lot of gangs, and druggies. it's dangerous here and would not recommend anyone move here."
    9
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  • Mr.jones.jones1989
    "There’s a lot of dog owners around where I live now and all dogs are welcomed here. No dogs Rome freely everyone cleans up behind there dogs"
    3
    Flag
  • Sexydova14043
    "That the area is safe for kids. Also that the school district is good. They should be able to walk around the community being safe"
    0
    Flag
  • Romerofam38
    "Very close to LIRR and major highways, also the federal courthouse. Great for commuting! Lots of new building coming in the next few years"
    1
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  • Lilianajtoro
    "The area is very quiet and neighbors look out for each other. Everybody has a great relationship and very friendly environment. "
    1
    Flag

LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026-09-14 00:43:25 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 39 Chestnut Street

  • What is 39 Chestnut Street estimated to be worth?
    Trulia's estimated value for 39 Chestnut Street in Central Islip, NY is $765,500.
  • What is the price history for 39 Chestnut Street?
    39 Chestnut Street in Central Islip, NY last sold for $730,000 in October 2025.
  • Is Central Islip a buyer's or seller's market?
    Central Islip is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Central Islip?
    Residents describe Central Islip, NY as easy to park in, well-kept, and dog-friendly. Most residents say you need a car. See recently sold homes in Central Islip, NY.
  • How big is the lot at 39 Chestnut Street?
    The lot at 39 Chestnut Street in Central Islip, NY is about 0.35 acres (15,246 sq ft).
  • Does 39 Chestnut Street have a garage?
    Yes, 39 Chestnut Street in Central Islip, NY has a garage.

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Apartments for Rent

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Off Market Homes Near 39 Chestnut Street

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Homes for sale near 39 Chestnut Street

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