39 Fallen Leaf Road, Holbrook, NY 11741
FOR SALE

39 Fallen Leaf Road
Holbrook, NY 11741

  • 4 Beds
  • 2.5 Baths
  • 1,781 sqft

$785,000

Est. Mortgage $5,042/mo*
Get Pre-Qualified

$785,000

Est. Mortgage $5,042/mo*
Get Pre-Qualified
4 Beds
2.5 Baths
1,781 sqft
We estimate this home will sell faster than 81% nearby.

Local Information

Map showing home location
© Google
-- mins to
Commute Destination

Description

Welcome Home to this beautiful, meticulously maintained Colonial in Holbrook’s most desirable neighborhood. This freshly painted 4-bedroom, 2.5-bath home blends classic charm with updates: a one-year-old roof, new front windows (1 yr), and efficient ductless heating/cooling units throughout. Bright, spacious living areas flow easily from the formal living room to a welcoming dining room and a well-appointed kitchen warmed by natural light. The attached 2 car garage provides direct entry and extra storage.

Upstairs you’ll find four generous bedrooms offering comfort and privacy for guests. Outside, enjoy a private backyard oasis featuring an in-ground pool with a 2-year-old liner, a durable Trex deck for outdoor dining and entertaining.

Conveniently located in Holbrook’s sought-after area, this home is ready and ideal for buyers seeking quality, energy-efficient systems, and a true backyard retreat!
We estimate this home will sell faster than 81% nearby.

Home Highlights

Parking
Garage
Outdoor
Pool
A/C
Heating & Cooling
HOA
None
Price/Sqft
$441
Listed
7 days ago
Last check for updates: about 6 hours ago
Listing by: Serhant East End LLC, (646) 480-7665
Jennifer Lipman, (516) 242-4482
Source: OneKey® MLS as distributed by MLS GRID, MLS#988672
Also Listed on OneKey® MLS as distributed by MLS GRID.

Home Details for 39 Fallen Leaf Road

Interior Features

Interior Details
Number of Rooms: 10
Beds & Baths
Number of Bedrooms: 4Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 1781 Square Feet
Appliances & Utilities
Utilities: Electricity Connected, Sewer Connected, Water ConnectedAppliances: Stainless Steel Appliance(s)
Heating & Cooling
Heating: Ducts,ElectricHas CoolingAir Conditioning: DuctlessHas HeatingHeating Fuel: Ducts
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Flooring: Carpet, Hardwood
Levels, Entrance, & Accessibility
Floors: Carpet, Hardwood

Exterior Features

Exterior Home Features
Has a Private Pool
Parking & Garage
Number of Garage Spaces: 2Number of Covered Spaces: 2No CarportHas a GarageHas Open ParkingParking Spaces: 2Parking: Driveway,Garage
Pool
Pool: In GroundPool
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 3Days on Market: 7

Property Information

Year Built
Year Built: 1976
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Colonial
Building
Construction Materials: Shingle SidingNot Attached Property
Property Information
Parcel Number: 0500109000500105000

Price & Status

Price
List Price: $785,000Price Per Sqft: $441

Active Status

MLS Status: Active

Location

Direction & Address
City: Holbrook
School Information
Elementary School: Tamarac Elementary SchoolJr High / Middle School: Seneca Middle SchoolHigh School: Sachem High School EastHigh School District: Sachem

Agent Information

Listing Agent
Listing ID: 988672

Building

Building Area
Building Area: 2731 Square Feet

Community

Not Senior Community

HOA

No HOA

Lot Information

Lot Area: 10019 sqft

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

Mls Number: 988672Attic: FullShowing Advance Notice: 24Showing Requirements: 24 Hour Notice, Appointment Only, Call Listing Agent, Showing Service

Price History for 39 Fallen Leaf Road

DatePriceEventSource
04/29/2026$785,000Listed For SaleOneKey® MLS as distributed by MLS GRID #988672

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Property Tax and Assessment

Year2024
Tax
Assessment$41,500
Home facts updated by county records

Comparable Sales for 39 Fallen Leaf Road

Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
43 Fallen Leaf Road, Holbrook, NY
0.01
Single-Family Home
$690,000
05/04/26
4
2.5
2,155
326 Singingwood Drive, Holbrook, NY
0.10
Single-Family Home
$878,000
10/03/25
4
2.5
2,022
31 Fallen Leaf Road, Holbrook, NY
0.03
Single-Family Home
$760,211
01/20/26
3
1.5
1,603
98 Gainsborough Road, Holbrook, NY
0.10
Single-Family Home
$950,000
10/17/25
4
2.5
2,400
36 Flintridge Drive, Holbrook, NY
0.23
Single-Family Home
$875,000
02/09/26
4
2.5
2,418
376 Singingwood Drive, Holbrook, NY
0.27
Single-Family Home
$665,000
06/20/25
4
2.5
2,173
89 Live Oak Drive, Holbrook, NY
0.26
Single-Family Home
$680,000
11/20/25
3
2
1,700
32 San Rafael Avenue, Holbrook, NY
0.22
Single-Family Home
$690,000
02/19/26
3
2
1,483
270 Singingwood Drive, Holbrook, NY
0.25
Single-Family Home
$675,000
02/17/26
3
1.5
1,656
80 Burleigh Drive, Holbrook, NY
0.46
Single-Family Home
$675,000
02/18/26
4
3
1,900

Assigned Schools

These are the assigned schools for 39 Fallen Leaf Road.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

What Locals Say about Holbrook

At least 200 Trulia users voted on each feature.

  • 90 % Say car is needed

  • 89 % Say parking is easy

  • 88 % Say it's dog friendly

  • 84 % Say yards are well-kept

  • 80 % Say there's holiday spirit

  • 72 % Say people would walk alone at night

  • 67 % Say it's quiet

  • 66 % Say kids play outside

  • 59 % Say they plan to stay for at least 5 years

  • 58 % Say neighbors are friendly

  • 58 % Say there are sidewalks

  • 55 % Say streets are well-lit

  • 53 % Say it's walkable to grocery stores

  • 45 % Say it's walkable to restaurants

  • 43 % Say there's wildlife

  • 33 % Say there are community events

Learn more about our methodology.
  • Slimjim1230
    "Everything is easily accessible. I love being centrally located. Easy to get to Long Island Expressway, Veterans Memorial Highway, or Sunrise Highway. "
    0
    Flag
  • Grace Allen
    "All good. Family and pet friendly Neighbors are welcoming and courteous to our fur friends. Great town to live in and raise a family "
    0
    Flag
  • Trulia User
    "Park by target and many friendly people ……sometimes people don’t leash dogs but most are good about it"
    0
    Flag
  • Dpenzi41215
    "It’s a quiet nice neighborhood to walk the pets. It’s peaceful lots of friendly People and dogs "
    1
    Flag
  • Gretta G.
    "Nice, week maintained great for kids low crime. The people in my community are doing the best at keeping our neighbors safe"
    0
    Flag
  • Kristina B.
    "Block parties, and caring for each other and helping out in times of need!! They keep the streets safe and there are already people exercising!"
    1
    Flag
  • Anthea.biedermann
    "People shoot fireworks for nearly every holiday. Most streets east of Broadway have sidewalks, west of Broadway less."
    0
    Flag
  • Janet.kelly723
    "Need a car. No public transportation in walking distance. Ronkonkoma train station services north shore. Sayville train station is Montauk line and services South Shore. "
    1
    Flag
  • Michelle A.
    "Easy to navigate. Roads are clear, little to no pot holes. Everything is nearby, such as restaurants, grocery stores, retail shopping, parks, ect. "
    0
    Flag
  • Michael L.
    "It’s relatively low-trafficked, but still don’t let your kids play in the streets. Maybe when they’re teenagers, and you live on a dead end, but that’s the limit."
    0
    Flag
  • Lpeters806
    "Great neighborhood. Safe for walks and friendly neighbors. Close to everything! Great school district "
    0
    Flag
  • Michael L.
    "I’m unemployed, but when I had a job it was only 10 minutes. That was on purpose; I applied for, and got, a job close to home."
    0
    Flag
  • Mary M
    "There is a nice little park here for kids to play. It has a playground with swings, a track for you to walk around the playground, and a baseball field."
    2
    Flag
  • Ancomp76
    "My commute is straight forward. Many different routes running along Holbrook. Traffic can be heavy At times. All in all- Safe town. "
    1
    Flag
  • Stingrey1967
    "Quiet, peaceful, most people in the area are descent hard working middle class Americans. The community comes together in times of need."
    0
    Flag
  • Maria R.
    "There are many families around here and everyone is super friendly. The area is always kept neat and clean. "
    0
    Flag
  • Amy M
    "Upside is great location. Close to Patchogue and Ronkonkoma train, close to LIE, Nicolls and Sunrise Hwy, and a short drive to the either shore. Downside, it’s suburbia. "
    3
    Flag
  • Ancomp76
    "People should pick up after their dogs. I like to exercise daily in and around the neighborhood and it’s unfortunate that dog owners do not clean up. People are very friendly in Holbrook. "
    2
    Flag
  • Dcdolphin
    "Bumper to bumper traffic during rush hour. Parking lot city. Unless you are lucky enough to reverse commute"
    1
    Flag
  • Mskristin
    "Amazing place to live. close to all transportation. Great schools, friendly neighborhood, kids ride bikes all over town. Holbrook has its own chamber of commerce. We have parades, clean up days. Holbrook is clean. There is everything you would need with in a mile of your home. I'm so happy I picked Holbrook. Been here ten years now."
    7
    Flag
  • Trulia User
    "Still nice in HOLBROOK. Sachem school district is over priced. Brookhaven town is also over priced. PSEG is way over priced."
    0
    Flag
  • Slettieri325
    "This neighborhood is a wonderful place to live. Close to the train, and restaurants. Good neighbors and great family activities. "
    6
    Flag
  • Mark
    "I live in this neighborhood for 23 years and loving it. Main st is a few blocks from where I live and I enjoy the restaurants, the services around there. "
    6
    Flag
  • Mperez724
    "Might not like the fact there are no sidewalks. Also no neighborhood parks for dogs or kids nearby. "
    0
    Flag
  • Philomena L.
    "It’s a great place to bring up kids and a great community. Highly recommend to anyone. It’s a great town."
    0
    Flag
  • Philomena L.
    "Holbrook is a great family community. The school district Sachem is one of the largest in New York State. Great restaurants and shops, a real small town feel."
    0
    Flag
  • Philomena L.
    "Holbrook is a great family town. Great schools, friendly people and safe. Raised our kids here and we are Sachem Proud!"
    0
    Flag
  • Djenannej
    "This neighborhood is nice and i always feel safe walking at night. It’s clean and quiet and people are friendly"
    0
    Flag
  • Roberto P.
    "Is quiet and everything is close. school are excellent and with a wonderful library. Street are clean and taxes are Fair. "
    0
    Flag

LGBTQ Local Legal Protections

Jennifer Lipman, Serhant East End LLC, (646) 480-7665
Agent Phone: (516) 242-4482
Based on information submitted to the MLS GRID as of 2026-02-06 15:18:24 PST. 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
39 Fallen Leaf Road, Holbrook, NY 11741 is a 4 bedroom, 3 bathroom, 1,781 sqft single-family home built in 1976. This property is currently available for sale and was listed by OneKey® MLS as distributed by MLS GRID on Apr 29, 2026. The MLS # for this home is MLS# 988672.