Seller's Agent in 2026
George McKnight
George Mcknight REALTORS Inc
(631) 269-6666
8 in this area
57 Total Sales
109 Oakside Dr Smithtown, NY 11787
4
Beds
3.5
Baths
2,400
Sq Ft
2
Acres Lot
Highlights
- Barn
- Stables
- Ranch Style House
- Smithtown Elementary School Rated A-
- 2 Acre Lot
- Granite Countertops
About This Home
As of March 2026Welcome to 109 Oakside Dr., your dream equestrian retreat, set on 2 scenic acres in the heart of Smithtown. This updated 4-bed, 3.5-bath ranch blends easy single-level living with true equestrian amenities. An eat-in kitchen with granite counters and stainless appliances opens to a spacious family room anchored by a stone fireplace. Throughout the home you’ll find hardwood floors, custom millwork, and recessed lighting. The private main bedroom offers direct access to a low-maintenance Azek deck overlooking a serene backyard with outdoor fireplace, waterfall, and koi pond. A finished basement adds flexible recreation/storage space. For horse enthusiasts: a meticulously maintained barn with 4 heated stalls, tack room, washroom, and hayloft; plus a PVC-fenced paddock with lighting and irrigation for year-round care. Move-in ready and thoughtfully appointed—an exceptional property where comfort, convenience, and equestrian living come together.
Last Agent to Sell the Property
George Mcknight REALTORS Inc Brokerage Phone: 631-269-6666 License #31MC0977633 Listed on: 09/20/2025
Home Details
Home Type
- Single Family
Est. Annual Taxes
- $29,386
Year Built
- Built in 1960
Lot Details
- 2 Acre Lot
- Vinyl Fence
- Back Yard Fenced
Parking
- 2 Car Garage
Home Design
- Ranch Style House
- Vinyl Siding
Interior Spaces
- 2,400 Sq Ft Home
- Recessed Lighting
- Fireplace
- Entrance Foyer
- Formal Dining Room
- Dryer
- Finished Basement
Kitchen
- Eat-In Kitchen
- Electric Oven
- Electric Cooktop
- Microwave
- Dishwasher
- Granite Countertops
Bedrooms and Bathrooms
- 4 Bedrooms
- Bathroom on Main Level
Schools
- Accompsett Elementary School
- Accompsett Middle School
- Smithtown High School-West
Horse Facilities and Amenities
- Horses Allowed On Property
- Corral
- Stables
- Arena
Utilities
- Central Air
- Hot Water Heating System
- Heating System Uses Oil
- Cesspool
- Cable TV Available
Additional Features
- Shed
- Barn
Listing and Financial Details
- Assessor Parcel Number 0800-035-00-04-00-036-000
Ownership History
Date
Name
Owned For
Owner Type
Purchase Details
Closed on
Aug 22, 2011
Sold by
Fc Ny Property T3 Llc
Bought by
Vivolo Vincent and Vivolo Veronica
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$540,350
Outstanding Balance
$363,784
Interest Rate
4.52%
Mortgage Type
FHA
Estimated Equity
$1,051,577
Purchase Details
Closed on
Sep 2, 2010
Sold by
Deutsche Bank National Trust Company and Soundview Home Loan Trust 2006 Opt2
Bought by
Fcny Property T3 Llc
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Original Mortgage
$25,000
Interest Rate
4.37%
Mortgage Type
Unknown
Purchase Details
Closed on
May 27, 2010
Sold by
Denicola Andrea and Leach Robert R
Bought by
Deutsche Bank National Trust Company and Soundview Home Loan Trust 2006 Opt2
Purchase Details
Closed on
Jun 18, 1997
Sold by
Cunningham Catherine
Bought by
Leach Robert R
Create a Home Valuation Report for This Property
The Home Valuation Report is an in-depth analysis detailing your home's value as well as a comparison with similar homes in the area
Home Values in the Area
Average Home Value in this Area
Purchase History
| Date | Type | Sale Price | Title Company |
|---|---|---|---|
| Bargain Sale Deed | $585,000 | -- | |
| Bargain Sale Deed | $585,000 | -- | |
| Bargain Sale Deed | $585,000 | -- | |
| Special Warranty Deed | $400,000 | -- | |
| 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 |
Source: Public Records
Property History
| Date | Event | Price | List to Sale | Price per Sq Ft |
|---|---|---|---|---|
| 03/31/2026 03/31/26 | Sold | $1,300,000 | -10.3% | $542 / Sq Ft |
| 02/09/2026 02/09/26 | Pending | -- | -- | -- |
| 10/26/2025 10/26/25 | Price Changed | $1,450,000 | -3.3% | $604 / Sq Ft |
| 09/20/2025 09/20/25 | For Sale | $1,499,990 | -- | $625 / Sq Ft |
Source: OneKey® MLS
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
Agents Affiliated with this Home
-
George McKnight
-
Betty Anne Smith
Buyer's Agent in 2026
Betty Anne Smith
Howard Hanna Coach
(631) 757-4000
4 in this area
32 Total Sales
Map
Source: OneKey® MLS
MLS Number: 915379
APN: 0800-035-00-04-00-036-000
Disclaimer: Certain information contained herein is derived from information provided by parties other than Homes.com. All information provided is deemed reliable, but is not guaranteed to be accurate and should be independently verified.
The data relating to real estate for sale or lease on this web site comes in part from OneKey® MLS. Real estate listings held by brokerage firms other than Ten-X are marked with the OneKey® MLS logo or an abbreviated logo and detailed information about them includes the name of the listing broker.
Based on information submitted to the MLS GRID. 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. IDX information is provided exclusively for personal, non-commercial use, and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing.
Information is deemed reliable but not guaranteed.
Copyright 2026 OneKey® MLS. All rights reserved.
Based on information submitted to the MLS GRID
Listings courtesy of OneKey® MLS as distributed by MLS GRID
Nearby Homes
- 144 Landing Meadow Rd
- 1 Valley Ave
- 81 Oakside Rd
- 2 Riverview Terrace
- 41 Landing Meadow Rd
- 326 Nissequogue River Rd
- 326A River Rd
- 0 Laurel Hill Path
- 277 River Rd
- 11 Dehan St
- 18 Ursular Ct
- 16 Ursular Ct
- 14 Ursular Ct
- 7 Ursular Ct
- 48 River Heights Dr
- 749 E Main St
- 1117 Saint Johnland Rd
- 20 Veronica Ct
- 111 Aspen Rd
- 2 Vistas Cir
Your Personal Tour Guide
Ask me questions while you tour the home.