Ronni Tranes
Douglas Elliman Real Estate
(631) 791-6476
129 Total Sales
19 in Smithtown
$540K - $1.2M Price Range
Estimated Value: $1,349,667
Welcome 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
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
Ronni Tranes
Douglas Elliman Real Estate
(631) 791-6476
129 Total Sales
19 in Smithtown
$540K - $1.2M Price Range
Anthony Autera
Signature Premier Properties
(631) 791-6327
100 Total Sales
1 in Smithtown
$860,000 Price
James Szollosi
Signature Premier Properties
(631) 646-2134
43 Total Sales
1 in Smithtown
$510,000 Price
Deborah Munro
BERKSHIRE HATHAWAY
(516) 219-8595
20 Total Sales
1 in Smithtown
$645,000 Price
Kerri McDonald
Cornerstone Properties of LI
(631) 646-1648
34 Total Sales
4 in Smithtown
$525K - $750K Price Range
Amy Satchell
Howard Hanna Coach
(631) 769-2956
46 Total Sales
1 in Smithtown
$625,000 Price
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Buyer | Sale Price | Title Company |
|---|---|---|---|
| $510,000 | -- | ||
| $255,000 | First American Title Ins Co |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| Date | Status | Borrower | Loan Amount |
|---|---|---|---|
| Open | $25,000 | ||
| Previous Owner | $273,000 |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| 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 |
We collect this data history from publicly available records. To have your information removed, we recommend requesting removal directly through your county’s website.
| 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 |
|---|---|---|---|---|
| 2025 | $28,619 | $11,252 | $790 | $10,462 |
| 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 |
Seller's Agent in 2026
George McKnight
George Mcknight REALTORS Inc
(631) 269-6666
57 Total Sales
Buyer's Agent in 2026
Betty Anne Smith
Howard Hanna Coach
(631) 757-4000
34 Total Sales
Source: OneKey® MLS
MLS Number: 915379
APN: 0800-035-00-04-00-036-000
Ask me questions while you tour the home.