$1,499,990
$299K PRICE DROP

109 Oakside Dr Smithtown, NY 11787

Estimated payment $10,439/month

Total Views 15,880
4 Beds
4 Baths
2,283 Sq Ft
$657 Price per Sq Ft

Highlights

  • Barn
  • Horses Allowed On Property
  • Deck
  • Smithtown Elementary School Rated A-
  • 2 Acre Lot
  • Ranch Style House

About This Home

Luxury Living & Exceptional Horse Property in the Heart of Smithtown
Set on 2 picturesque acres in a highly desirable Smithtown location, this 4-bedroom, 4-bath home offers the perfect blend of refined residential comfort and premium equestrian amenities - a rare and remarkable find.
Inside the home features an open floor plan that flows effortlessly for modern living. An updated eat-in kitchen with granite countertops and stainless steel appliances opens to a spacious family room centered around a striking stone fireplace, ideal for relaxing or entertaining. Refinished hardwood floors, recessed lighting, and custom moldings elevate the space, while the freshly painted interior and updated baths offer a move-in-ready experience.
The large main bedroom includes direct access to the backyard and deck - your own private retreat . A fully finished basement adds even more versatility to meet your lifestyle needs.
Step outside to an expansive Azek deck with an outdoor stone fireplace and tranquil waterfall, creating a peaceful backdrop for gatherings or quiet evening.
This is more than a property - it's a special, one-of-a-kind equestrian haven.
The meticulously maintained 4-stall barn is equipped with heat lamps on timers, a heated tack room with slop sink, and a hayloft for streamlined storage. PVC- fenced paddock is fully outfitted with lighting and irrigation, offering exceptional care and convenience for your horses.
A rare opportunity to own a turnkey home and horse property in a prime Smithtown setting - where luxury, lifestyle, and land come together beautifully.

Listing Agent

William Zezelic

Signature Premier Properties Brokerage Phone: 631-751-2111 License #30ZE0842843 Listed on: 06/16/2025

Signature Premier Properties

Home Details

Home Type

  • Single Family

Est. Annual Taxes

  • $29,360

Year Built

  • Built in 1960

Parking

  • 2 Car Garage
  • Driveway

Home Design

  • Ranch Style House
  • Frame Construction
  • Vinyl Siding

Interior Spaces

  • 2,283 Sq Ft Home
  • Crown Molding
  • Recessed Lighting
  • Living Room with Fireplace
  • Formal Dining Room
  • Finished Basement
  • Basement Fills Entire Space Under The House

Kitchen

  • Eat-In Kitchen
  • Oven
  • Microwave
  • Dishwasher
  • Stainless Steel Appliances
  • Granite Countertops

Flooring

  • Wood
  • Ceramic Tile

Bedrooms and Bathrooms

  • 4 Bedrooms
  • En-Suite Primary Bedroom
  • 4 Full Bathrooms

Laundry

  • Laundry Room
  • Dryer

Schools

  • Accompsett Elementary School
  • Accompsett Middle School
  • Smithtown High School-West

Utilities

  • Central Air
  • Heating System Uses Oil
  • Cesspool

Additional Features

  • Deck
  • 2 Acre Lot
  • Barn
  • Horses Allowed On Property

Listing and Financial Details

  • Assessor Parcel Number 0800-035-00-04-00-036-000

Home Details

Home Type

Single Family

Est. Annual Taxes

$29,360

Year Built

Built in 1960

Lot Details

0

Parking

2

Listing Details

  • Property Type: Residential
  • Architectural Style: Ranch
  • Property SubType: Single Family Residence
  • Levels: One
  • Year Built: 1960
  • Attribution Contact: 631-751-2111
  • Carport Y N: No
  • Special Features: VirtualTour
  • Property Sub Type: Detached

Interior Features

  • Appliances: Dishwasher, Dryer, Microwave, Oven, Refrigerator, Stainless Steel Appliance(s)
  • Interior Amenities: First Floor Bedroom, First Floor Full Bath, Crown Molding, Eat-in Kitchen, Formal Dining, Granite Counters, Primary Bathroom, Recessed Lighting
  • Fireplaces: 1
  • Flooring: Ceramic Tile, Hardwood
  • Fireplace Features: Living Room
  • Full Bathrooms: 4
  • Basement: Finished, Full
  • Total Bedrooms: 4
  • Fireplace: Yes
  • Living Area: 2283
  • Basement YN: Yes

Exterior Features

  • Other Structures: Barn(s)
  • Construction Materials: Frame, Other, Vinyl Siding
  • Pool Private: No
  • Road Frontage Type: Municipal
  • Patio and Porch Features: Deck
  • Waterfront: No
  • Foundation Details: Other

Garage/Parking

  • Garage Spaces: 2
  • Garage: Yes
  • Parking Description: Driveway, Garage

Utilities

  • Cooling: Central Air
  • Heating: Oil
  • Laundry Features: Laundry Room
  • Sewer: Cesspool
  • Utilities: See Remarks
  • Water Source: Public

Condo/Co-op/Association

  • Senior Community: No
  • Association: No

Schools

  • Middle School: Accompsett Middle School

Lot Info

  • Horses: Yes
  • Lot Size Acres: 2
  • Lot Size Sq Ft: 87120
  • Parcel Number: 0800-035-00-04-00-036-000
  • Property Attached: No

Rental Info

  • Lease Considered: No

Tax Info

  • Tax Annual Amount: 29359.64
  • Tax Year: 2025

MLS Schools

  • Elementary School: Accompsett Elementary School
  • High School: Smithtown High School-West
  • Middle School District: Smithtown

Map

Range of Values:

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Home Values in the Area

Source: Public Records

Average Home Value in this Area





Source: Public Records

Tax History

Year Tax Paid Tax Assessment Tax Assessment Total Assessment is a certain percentage of the fair market value that is determined by local assessors to be the total taxable value of land and additions on the property. Land Improvement
2024 $28,619 $11,252 $790 $10,462
2023 $28,619 $11,252 $790 $10,462
2022 $27,179 $11,252 $790 $10,462
2021 $27,179 $11,252 $790 $10,462
2020 $27,357 $11,252 $790 $10,462
2019 $27,357 $0 $0 $0
2018 -- $11,252 $790 $10,462
2017 $25,672 $11,252 $790 $10,462
2016 $26,681 $11,850 $790 $11,060
2015 -- $11,850 $790 $11,060
2014 -- $11,850 $790 $11,060
Source: Public Records

Property History

Date Event Price Change Sq Ft Price
07/21/2025 07/21/25 Price Changed $1,499,990 -16.6% $657 / Sq Ft
06/16/2025 06/16/25 For Sale $1,799,000 -- $788 / Sq Ft
Source: OneKey® MLS

Purchase History

Date Type Sale Price Title Company
Bargain Sale Deed $585,000 --
Bargain Sale Deed $585,000 --
Special Warranty Deed $400,000 --
Special Warranty Deed $400,000 --
Foreclosure Deed $510,000 --
Foreclosure Deed $510,000 --
Deed $255,000 First American Title Ins Co
Deed $255,000 First American Title Ins Co
Source: Public Records

Mortgage History

Date Status Loan Amount Loan Type
Open $540,350 FHA
Closed $540,350 FHA
Previous Owner $25,000 Unknown
Previous Owner $25,000 Unknown
Previous Owner $273,000 Unknown
Source: Public Records

Source: OneKey® MLS

MLS Number: 877074

OneKey® MLS

APN: 0800-035-00-04-00-036-000