Amy Kernaghan
REALTY DIRECT NY INC
(516) 518-8097
134 Total Sales
2 in Smithtown
$550K - $795K Price Range
109 Oakside Dr Smithtown, NY 11787
Smithtown AreaEstimated Value: $1,329,000
4
Beds
3.5
Baths
2,400
Sq Ft
$554/Sq Ft
Est. Value
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
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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
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
Name
Owned For
Owner Type
Purchase Details
Listed on
Sep 20, 2025
Closed on
Mar 26, 2026
Sold by
Vivolo Vincent and Vivolo Veronica
Bought by
Seller's Agent
George McKnight
George Mcknight REALTORS Inc
Buyer's Agent
Betty Anne Smith
Howard Hanna Coach
List Price
$1,499,990
Sold Price
$1,300,000
Premium/Discount to List
-$199,990
-13.33%
Views
608
Current Estimated Value
Home Financials for this Owner
Home Financials are based on the most recent Mortgage that was taken out on this home.
Estimated Appreciation
$29,000
Avg. Annual Appreciation
4.91%
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
Interest Rate
4.37%
Mortgage Type
FHA
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
Purchase Money Mortgage
Purchase Details
Closed on
May 27, 2010
Sold by
Denicola Andrea
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
Home Values in the Area
Average Home Value in this Area
Agents Specializing in Smithtown, NY
-
Amy Kernaghan
-
Nordeen Accardi
Nordeen Accardi
Coldwell Banker American Homes
(631) 776-4738
283 Total Sales
14 in Smithtown
$505K - $2.2M Price Range
-
Rossy Ceron
Rossy Ceron
Century Homes Realty Group LLC
(646) 362-9126
13 Total Sales
1 in Smithtown
$1,200,000 Price
-
Laura Cochran
Laura Cochran
BERKSHIRE HATHAWAY
(631) 250-8292
205 Total Sales
5 in Smithtown
$630K - $885K Price Range
-
Jagmeet Bedi
Jagmeet Bedi
Compass
(855) 934-0730
111 Total Sales
2 in Smithtown
$575K - $700K Price Range
-
Selwyn Prince
Selwyn Prince
Majestic Homes & Estates LLC
(844) 933-1249
8 Total Sales
1 in Smithtown
$625,000 Price
Purchase History
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 | -- | ||
| Leach Robert R | $255,000 | First American Title Ins Co |
Source: Public Records
Mortgage History
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 | Leach Robert R | $273,000 |
Source: Public Records
Property History
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 |
Source: OneKey® MLS
Tax History
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 |
Source: Public Records
Agents Affiliated with this Home
-
George McKnight
Seller's Agent in 2026
George McKnight
George Mcknight REALTORS Inc
(631) 269-6666
59 Total Sales
-
Betty Anne Smith
Buyer's Agent in 2026
Betty Anne Smith
Howard Hanna Coach
(631) 757-4000
35 Total Sales
Map
Source: OneKey® MLS
MLS Number: 915379
APN: 0800-035-00-04-00-036-000
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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
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