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 $6,753/mo*
Refinance Your Home

$1,035,000

Last Sold: Oct 28, 2025
1% below list $1.05M
$398/sqft
Est. Refi. Payment $6,753/mo*
Refinance Your Home
3 Beds
2.5 Baths
2,600 sqft

Local Information

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

Description

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!
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources. This description is from November 04, 2025

Home Highlights

Parking
Garage
Outdoor
Patio
A/C
Heating & Cooling
HOA
$690/Monthly
Price/Sqft
$398/sqft
Listed
180+ days ago

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
Last check for updates: about 23 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

Price History for 27 Captains Drive

DatePriceEventSource
10/28/2025$1,035,000Sold
OneKey® MLS as distributed by MLS GRID #893736
07/31/2025$1,050,000PendingOneKey® MLS as distributed by MLS GRID #893736
07/25/2025$1,050,000Listed For SaleOneKey® MLS as distributed by MLS GRID #893736
03/24/2021ListingRemovedN/A
03/20/2019$590,000Sold
N/A
01/23/2019$599,900PendingN/A
01/12/2019$599,900PriceChange
N/A
10/14/2018$649,900Listed For SaleN/A
07/02/2010$535,000Sold
N/A
05/07/2008$649,000ListingRemovedAgent Provided
04/04/2008$649,000PriceChange
Agent Provided
02/26/2008$729,000PriceChange
Agent Provided
02/01/2008$759,000Listed For SaleAgent Provided
09/22/1998$249,000Sold
N/A
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Property Tax and Assessment

Year2025
Tax
Assessment$59,500
Home facts updated by county records

Comparable Sales for 27 Captains Drive

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
12/24/25
4
2
2,662
136 Cedar Avenue, Islip, NY
0.51
Single-Family Home
$750,000
11/17/25
3
2.5
2,346
277 Ocean Avenue, Islip, NY
0.30
Single-Family Home
$762,000
07/21/25
4
2
2,000
15 Cedar Avenue Extension, Islip, NY
0.32
Single-Family Home
$1,350,000
10/22/25
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
2 Bay Place, Bay Shore, NY
0.45
Single-Family Home
$735,000
05/19/26
4
2
1,870
4 Colonial Court, Bay Shore, NY
0.46
Single-Family Home
$999,999
05/15/26
4
2.5
3,087

Nearby homes

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Assigned Schools

These are the assigned schools for 27 Captains Drive.
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 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

  • 64 % Say neighbors are friendly

  • 64 % Say it's quiet

  • 63 % Say it's walkable to restaurants

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

  • 62 % Say streets are well-lit

  • 60 % Say there are sidewalks

  • 59 % Say there's wildlife

  • 58 % Say it's walkable to grocery stores

  • 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

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Homes for sale near 27 Captains Drive

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Off Market Homes Near 27 Captains Drive

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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

Homes for rent near 27 Captains Drive

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27 Captains Drive, Islip, NY 11751 is a 3 bedroom, 3 bathroom, 2,600 sqft single-family home built in 1978. This property is not currently available for sale. 27 Captains Drive was last sold on Oct 28, 2025 for $1,035,000 (1% lower than the asking price of $1,050,000). The current Trulia Estimate for 27 Captains Drive is $1,080,900.