27 Captains Drive, Islip, NY 11751
SOLD
OCT 28, 2025

27 Captains Drive
Islip, NY 11751

  • 3 Beds
  • 2.5 Baths
  • 2,600 sqft

$1,035,000

Last Sold: Oct 28, 2025
1% below list $1.05M
$398/sqft
Est. Refi. Payment $6,921/mo*
Refinance Your Home

$1,035,000

Last Sold: Oct 28, 2025
1% below list $1.05M
$398/sqft
Est. Refi. Payment $6,921/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,600 sqft

Home Value

Trulia Estimate
$1.08M
Since last month
$400 (0%)
Since last year
Increased$7K (+0.7%)
Since last sale
Increased$46K (+4.4%)
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 +96% in the last 10 years
MonthEstimated value
2026
August 2026$1.08M
July 2026$1.08M
June 2026$1.07M
May 2026$1.08M
April 2026$1.07M
March 2026$1.07M
February 2026$1.06M
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
375 Ocean Avenue, Islip, NY
0.16
Single-Family Home
$1,110,000
05/08/26
4
2.5
2,925
140 Ocean Avenue, Islip, NY
0.40
Single-Family Home
$835,000
01/27/26
4
2.5
2,676
287 Cedar Avenue, Islip, NY
0.27
Single-Family Home
$950,000
03/25/26
4
2
2,662
136 Cedar Avenue, Islip, NY
0.51
Single-Family Home
$750,000
11/17/25
3
2.5
2,346
15 Cedar Avenue Extension, Islip, NY
0.32
Single-Family Home
$1,350,000
02/10/26
4
2.5
2,598
32 Cedar Avenue Extension, Islip, NY
0.30
Single-Family Home
$1,150,000
10/30/25
4
3
2,875
8 Adelphi Street, Islip, NY
0.27
Single-Family Home
$1,205,000
07/15/26
5
3.5
2,448
151 Church Avenue, Islip, NY
0.57
Single-Family Home
$950,000
07/13/26
4
2
2,450

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
375 Ocean Avenue, Islip, NY 11751
0.16
$1,110,000
4
2.5
2,925
Recently Sold
15 Post Lane, Bay Shore, NY 11706
0.25
$1,955,000
4
3.5
4,144
Off Market
276 Ocean Avenue, Islip, NY 11751
0.25
$2,231,400
6
6.5
6,619
Off Market
274 Ocean Avenue, Islip, NY 11751
0.28
-
-
-
-
Off Market
8 Adelphi Street, Islip, NY 11751
0.27
$1,205,000
5
3.5
2,448
Recently Sold
9 Post Lane, Bay Shore, NY 11706
0.31
$1,452,100
4
3
-
Off Market
7 Adelphi Street, Islip, NY 11751
0.28
$856,000
5
2
1,696
Off Market
277 Ocean Avenue, Islip, NY 11751
0.30
$805,000
4
2
2,000
Off Market
272 Ocean Avenue, Islip, NY 11751
0.31
$1,525,000
6
5.5
3,438
Recently Sold
287 Cedar Avenue, Islip, NY 11751
0.27
$950,000
4
2
2,662
Recently Sold
15 Chanticleer Drive, Islip, NY 11751
0.32
$1,445,600
3
2
3,100
Off Market

Local Information

  • Map ViewExplore the area around 27 Captains Drive.
  • Schools3 Elementary Schools1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1978
Living Area
2,600 sqft
Price/Sqft
$398/sqft
Parking
Garage
HOA
$690/Monthly

About this House

Welcome to the Club at Bayberry Harbor, one of Long Island's most exclusive waterfront communities offering breathtaking views of the Great South Bay and a lifestyle designed for relaxation and sophistication. Enjoy your deeded boat slip with electric and water access in the marina. Within this private waterfront community, the "arboretum" refers to manicured, tree lined gardens and green corridors designed for serene walks and natural beauty. This offers residents a peaceful setting along with a private clubhouse, gym and outdoor pool with firepit. Enjoy playing tennis and pickleball with your community members. At the Club you will enjoy amazing sunsets. This development is approximately 22.214 acres!

This Lovely two-story townhome offers the perfect blend of comfort and natural beauty. Relax outside on your bluestone patio, where you enjoy quiet ,serene views of the lush arboretum and pond. This townhome features many updates, There is a full expansion which includes an extra bedroom, all California Closets, and 2 additional skylights. Additional features include wood flooring, wood burning fireplace, new windows, two sets of new 8' sliders. Exterior features new siding, second story expanded deck and new roof.
This property is located in X Flood Zone! Pets are welcome!
27 Captains Drive, Islip, NY 11751 is a 3 bedroom, 3 bathroom, 2,600 sqft single-family home built in 1978. It last sold for $1,035,000 on Oct 28, 2025 (1% below the $1,050,000 asking price). It is currently off market. The Trulia Estimate is $1,079,000, with a rent estimate of $4,733/month.
Last check for updates: about 18 hours ago
Listed by Michelle A. Furno CBR
Signature Premier Properties, (631) 647-4880
Bought with: Michelle A. Furno CBR, Signature Premier Properties, (631) 647-4880
Source: OneKey® MLS as distributed by MLS GRID, MLS#893736

Home Details for 27 Captains Drive

Interior Features

Interior Details
Number of Rooms: 7
Beds & Baths
Number of Bedrooms: 3Number of Bathrooms: 3Number of Bathrooms (full): 2Number of Bathrooms (half): 1
Dimensions and Layout
Living Area: 2600 Square Feet
Appliances & Utilities
Utilities: Cable Available, Electricity Connected, Natural Gas Available, Phone Available, Sewer Connected, Trash Collection Private, Underground Utilities, Water ConnectedAppliances: Cooktop, Dishwasher, Dryer, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s), WasherDishwasherDryerLaundry: Inside,Laundry RoomMicrowaveRefrigeratorWasher
Heating & Cooling
Heating: Electric,Forced AirHas CoolingAir Conditioning: Central AirHas HeatingHeating Fuel: Electric
Fireplace & Spa
Number of Fireplaces: 1Fireplace: Wood BurningHas a FireplaceNo Spa
Gas & Electric
Has Electric on Property
Windows, Doors, Floors & Walls
Window: BlindsFlooring: Carpet, Hardwood, Tile
Levels, Entrance, & Accessibility
Levels: TwoFloors: Carpet, Hardwood, Tile
View
Has a ViewView: Open

Exterior Features

Exterior Home Features
Patio / Porch: PatioNo Private Pool
Parking & Garage
Number of Garage Spaces: 1Number of Covered Spaces: 1No CarportHas a GarageParking Spaces: 2Parking: Garage
Frontage
Waterfront: Beach Access, Bulkhead, Canal Access, Water Access
Water & Sewer
Sewer: Public Sewer

Days on Market

Cumulative Days on Market: 6

Property Information

Year Built
Year Built: 1978
Property Type / Style
Property Type: ResidentialProperty Subtype: Single Family Residence, ResidentialArchitecture: Other
Building
Construction Materials: Vinyl SidingAttached To Another Structure
Property Information
Parcel Number: 0500443000200010000

Price & Status

Price
List Price: $1,050,000Price Per Sqft: $398/sqft
Status Change & Dates
Off Market Date: Thu Jul 31 2025

Active Status

MLS Status: Sold

Location

Direction & Address
City: IslipCommunity: The Club At Bayberry Harbor
School Information
Elementary School: Maud S Sherwood Elementary SchoolJr High / Middle School: Islip Middle SchoolHigh School: Islip High SchoolHigh School District: Islip

Building

Building Area
Building Area: 2676 Square Feet
Community rooms
Fitness Center

Community

Community Features: Clubhouse, Fitness Center, Pool, Tennis Court(s)Not Senior Community

HOA

HOA Fee Includes: Maintenance Grounds, Pool Service, Snow Removal, TrashHas an HOAHOA Fee: $690/Monthly

Lot Information

Lot Area: 2614 sqft

Listing Info

Special Conditions: None

Offer

Listing Agreement Type: Exclusive Right To Sell

Miscellaneous

Mls Number: 893736Attic: PartialAttribution Contact: 631-647-4880Showing Requirements: Appointment Only, Call Listing Agent

Additional Information

HOA Amenities: Clubhouse,Fitness Center,Pool,Snow Removal,Tennis Court(s),Trash

Price and Tax history

DateEventPrice
Oct 28, 2025
Source: OneKey® MLS as distributed by MLS GRID #893736
Sold
$1,035,000
Jul 31, 2025
Source: OneKey® MLS as distributed by MLS GRID #893736
Pending
$1,050,000
Jul 25, 2025
Source: OneKey® MLS as distributed by MLS GRID #893736
Listed For Sale
$1,050,000
Mar 24, 2021
Source: N/A
ListingRemoved
Mar 20, 2019
Source: N/A
Sold
$590,000

Market trends in Islip

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
—
Sale-to-List Price
—
Price per sq ft
—
Available listings
36
6MoM

Around this home

What Locals Say about Islip

At least 118 Trulia users voted on each feature.

  • 90 % Say parking is easy

  • 90 % Say it's dog friendly

  • 88 % Say car is needed

  • 86 % Say there's holiday spirit

  • 85 % Say yards are well-kept

  • 75 % Say people would walk alone at night

  • 73 % Say kids play outside

  • 65 % Say neighbors are friendly

  • 64 % Say it's quiet

  • 63 % Say it's walkable to restaurants

  • 62 % Say streets are well-lit

  • 62 % Say they plan to stay for at least 5 years

  • 59 % Say there are sidewalks

  • 59 % Say it's walkable to grocery stores

  • 59 % Say there's wildlife

  • 49 % Say there are community events

Sourced by Trulia users. Learn more about our methodology.
  • Michellereid2323
    "Family-oriented neighborhood. Main Street is charming, walkable, and dotted with boutiques, cafes, and diners."
    0
    Flag
  • Matt Classie
    "Street fairs, events at Brookwood Hall during holidays. Theres lots to do in the town of Islip. Bats & Brews is a great event."
    0
    Flag
  • Yen160107
    "I have kids that play in the front yard and they step on the dog feces that they left behind. Also I have signs that say “kids at play” but they do not care"
    0
    Flag
  • Trulia User
    "The drive is horrible and the traffic which is 300 feet from your front door is deafening! A ten lane super hwy and that’s what you wake up to at 4:30 am every day ! Or you can take the train a mile away which you can also here every morning blasting it’s way to islip train station . "
    0
    Flag
  • Trulia User
    "Well celebrate almost all the events soccer games good school very friendly neighborhoods good shopping center "
    1
    Flag
  • Jamal G.
    "this neighborhood is a great place to live there are restaurants in the mall nearby good schools and they are also close"
    14
    Flag
  • Stephen B.
    "The taxes are very high here for the school. Bay Shore schools are just as good or better and the taxes are much lower. "
    9
    Flag
  • Michael .
    "Good! I work in the city and take the LIRR. The islip station has free parking and plenty of spaces."
    1
    Flag
  • Monmona
    "you need to have a car to commute around. around. if you live close enough to the Long Island Railroad, then you can walk to the station and take the train from there."
    1
    Flag
  • Fldsetter
    "I grew up here and actually bought my childhood home back after living in another part of the country . Beaches are close , most folks keep there homes well maintained . There are lot of children here and the schools are second to none . I wish the town would replace the roads here , and take better care of there pubic areas ! But let the young folks moving in fight that fight ! "
    1
    Flag
  • Djhafner132
    "5 min to train station.the neighbors are friendly.i am an avid fisherman and two fishing piers are less than a mile away.the streets are well treed and maintained "
    0
    Flag
  • Djhafner132
    "I lived here since 1973.The homes are well kept and neighbors are friendly.the town dock is an easy walk with great fishing the streets are well maintained.All in all a great place to live"
    0
    Flag
  • Djhafner132
    "Parades block parties great fishing close by.great south of montauk location.Great place to raise a family "
    0
    Flag
  • Ricktssf
    "I work locally, so I can walk to work. the train station to NYC is only 4 blocks away. easy commute on the train. "
    2
    Flag
  • G.Greco
    "I've made Islip my home since 1980. Yards are well kept, the streets are maintained, paved and cleaned regularly. The school district is good. It's a good place to live and raise a family. This area south of Montauk is very desirable"
    16
    Flag
  • Tannuramees
    "parades, fairs, shops close by, farmers market, good schools, nice neighborhood, school events, town events"
    1
    Flag
  • Catherine M.
    "I have lived here for 18 years and for the most part it’s a good area. I am not a huge fan of the school district but it’s not horrible either ."
    11
    Flag
  • Stefbartoli
    "Dog friendly neighborhood! People walk their dogs around regularly. Neighbors look out for each other’s pets as well. "
    1
    Flag
  • Tyase930
    "Quiet respectful neighbors. Walking distance to stores. Lots of new businesses and new development s."
    0
    Flag
  • Tony H.
    "I live in this neighborhood for 2 years so far people are very friendly, there's always parking, people walk their dogs at night and exercise regularly. It's pretty cool !!!"
    0
    Flag
  • Fldsetter
    "Crappy roads / rats / compact floresant lights instead of LED ( someone got paid off ) no trees left due to disease , and the town is not planting any ! Highway noise 10 lanes now on Sunrise HWY - RT27 . No plans for a sound wall ??? I guess we are lower class here in Islip . Airplane and helicopters all day and night fly over head ,, isn’t there a bay or ocean they can fly over then go straight up Lakeland Blvd to the airport ???? I will eave as soon as I find a house elsewhere and not in NY "
    0
    Flag
  • Ricktssf
    "I'm 17 years living in Islip. a little great Hamlet along the great South Bay. Town of Islip is much larger, but this is a Suburban area. "
    0
    Flag

LGBTQ Local Legal Protections

Based on information submitted to the MLS GRID as of 2026-08-22 04:58:09 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 27 Captains Drive

  • What is 27 Captains Drive estimated to be worth?
    Trulia's estimated value for 27 Captains Drive in Islip, NY is $1,079,000.
  • What is the price history for 27 Captains Drive?
    27 Captains Drive in Islip, NY last sold for $1,035,000 in October 2025.
  • Is Islip a buyer's or seller's market?
    Islip is currently a seller's market, based on recent for-sale activity.
  • What do residents say about Islip?
    Residents describe Islip, NY as easy to park in, dog-friendly, and well-kept. Most residents say you need a car. See recently sold homes in Islip, NY.
  • Does 27 Captains Drive have air conditioning?
    Yes, 27 Captains Drive in Islip, NY has air conditioning.
  • Does 27 Captains Drive have a pool?
    Yes, 27 Captains Drive in Islip, NY has a pool.

Explore by feature - Air Conditioning

8 rentals with air conditioning in Islip, NY

Explore by feature - Washer/dryer

6 rentals with a washer/dryer in Islip, NY

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Off Market Homes Near 27 Captains Drive

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