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.
Sold for $1,300,000
$1,300,000
109 Oakside Drive, Smithtown, NY 11787
4beds
2,400sqft
Single Family Residence, Residential
Built in 1960
200 Acres Lot
$1,320,500 Zestimate®
$542/sqft
$5,194 Estimated rent
Home value
$1,320,500
$1.19M - $1.47M
$5,194/mo
Zestimate® history
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List your homeWhat's special
Scenic acresSerene backyardOutdoor fireplaceKoi pondFinished basementPrivate main bedroomRecessed lighting
Zillow last checked:
Listing updated:
Listed by:
George C. McKnight,
George Mcknight REALTORS Inc 631-269-6666
Bought with:
Betty Anne Smith, 10401357250
Howard Hanna Coach
Source: OneKey® MLS as distributed by MLS GRID,MLS#: 915379
Facts & features
Interior
Bedrooms & bathrooms
- Bedrooms: 4
- Bathrooms: 4
- Full bathrooms: 3
- 1/2 bathrooms: 1
Heating
- Hot Water, Oil
Cooling
- Central Air
Appliances
- Included: Dishwasher, Dryer, Electric Cooktop, Electric Oven, Microwave, Refrigerator
Features
- First Floor Bedroom, First Floor Full Bath, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters
- Basement: Finished
- Attic: Full,Unfinished
Interior area
- Total structure area: 2,400
- Total interior livable area: 2,400 sqft
Property
Parking
- Total spaces: 2
- Parking features: Garage
- Garage spaces: 2
Features
- Fencing: Back Yard,Vinyl
Lot
- Size: 200 Acres
Details
- Additional structures: Arena, Barn(s), Corral(s), Stable(s)
- Parcel number: 0800035000400036000
- Special conditions: None
- Horses can be raised: Yes
Construction
Type & style
- Home type: SingleFamily
- Architectural style: Ranch
- Property subtype: Single Family Residence, Residential
Materials
- Vinyl Siding
Condition
- Year built: 1960
Utilities & green energy
- Sewer: Cesspool
- Water: Public
- Utilities for property: Cable Available, Electricity Connected, Trash Collection Public, Water Connected
Community & HOA
HOA
- Has HOA: No
Location
- Region: Smithtown
Financial & listing details
- Price per square foot: $542/sqft
- Tax assessed value: $1,406,500
- Annual tax amount: $29,386
- Date on market: 9/20/2025
- Cumulative days on market: 238 days
- Listing agreement: Exclusive Right To Sell
- Electric utility on property: Yes
Price history
| Date | Event | Price |
|---|---|---|
| 3/31/2026 | Sold | $1,300,000-10.3%$542/sqft |
Source:  OneKey® MLS as distributed by MLS GRID #915379 Report a problem | ||
| 2/9/2026 | Pending sale | $1,450,000$604/sqft |
Source: OneKey® MLS as distributed by MLS GRID #915379 Report a problem | ||
| 10/26/2025 | Price change | $1,450,000-3.3%$604/sqft |
Source: OneKey® MLS as distributed by MLS GRID #915379 Report a problem | ||
| 9/20/2025 | Listed for sale | $1,499,990$625/sqft |
Source: OneKey® MLS as distributed by MLS GRID #915379 Report a problem | ||
| 9/20/2025 | Listing removed | $1,499,990$625/sqft |
Source: OneKey® MLS as distributed by MLS GRID #877074 Report a problem | ||
| 7/21/2025 | Price change | $1,499,990-16.6%$625/sqft |
Source: OneKey® MLS as distributed by MLS GRID #877074 Report a problem | ||
| 6/16/2025 | Listed for sale | $1,799,000+207.5%$750/sqft |
Source: OneKey® MLS as distributed by MLS GRID #877074 Report a problem | ||
| 9/6/2011 | Sold | $585,000-3.9%$244/sqft |
Source: Public Record Report a problem | ||
| 5/8/2011 | Listing removed | $609,000$254/sqft |
Source: Homelink Homes LLC #2344305 Report a problem | ||
| 4/2/2011 | Price change | $609,000-4.7%$254/sqft |
Source: Homelink Homes LLC #2344305 Report a problem | ||
| 1/16/2011 | Price change | $639,000-3%$266/sqft |
Source: Homelink Homes LLC #2344305 Report a problem | ||
| 11/13/2010 | Listed for sale | $659,000+64.8%$275/sqft |
Source: Homelink Homes LLC #2344305 Report a problem | ||
| 10/14/2010 | Sold | $400,000-11.1%$167/sqft |
Source: Public Record Report a problem | ||
| 7/31/2010 | Listed for sale | $450,000-11.8%$188/sqft |
Source: RE/MAX Best #2314838 Report a problem | ||
| 6/23/2010 | Sold | $510,000+100%$213/sqft |
Source: Public Record Report a problem | ||
| 6/30/1997 | Sold | $255,000$106/sqft |
Source: Public Record Report a problem | ||
Public tax history
| Year | Property taxes | Tax assessment |
|---|---|---|
| 2025 | -- | $11,252 |
| 2024 | -- | $11,252 |
| 2023 | -- | $11,252 |
| 2022 | -- | $11,252 |
| 2021 | -- | $11,252 |
| 2020 | -- | $11,252 |
| 2019 | -- | $11,252 |
| 2018 | -- | $11,252 |
| 2017 | $24,796 | $11,252 -5% |
| 2016 | -- | $11,850 |
| 2015 | -- | $11,850 |
| 2014 | -- | $11,850 |
| 2013 | -- | $11,850 +22.1% |
| 2012 | -- | $9,705 +7.3% |
| 2011 | -- | $9,045 |
| 2010 | -- | $9,045 |
| 2009 | -- | $9,045 |
| 2008 | -- | $9,045 |
| 2007 | $15,790 +20% | $9,045 |
| 2005 | $13,159 +7.1% | $9,045 |
| 2004 | $12,288 +1.3% | $9,045 |
| 2003 | $12,129 +8.1% | $9,045 |
| 2002 | $11,222 | $9,045 |
| 2001 | -- | $9,045 |
| 2000 | $10,361 | $9,045 |
Find assessor info on the county website
Neighborhood: 11787
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Nearby schools
GreatSchools rating
- 7/10Smithtown Elementary SchoolGrades: K-5Distance: 1.9 mi
- 7/10Accompsett Middle SchoolGrades: 6-8Distance: 2.2 mi
- 10/10Smithtown High School WestGrades: 9-12Distance: 2.3 mi
Schools provided by the listing agent
- Elementary: Accompsett Elementary School
- Middle: Accompsett Middle School
- High: Smithtown High School-West
Source: OneKey® MLS as distributed by MLS GRID. This data may not be complete. We recommend contacting the local school district to confirm school assignments for this home.
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Estimated market value
$1,320,500
Get a cash offer in 3 minutes
Find out how much your home could sell for in as little as 3 minutes with a no-obligation cash offer.
Estimated market value
$1,320,500
- New York
- Suffolk County
- Smithtown
- 11787
- 109 Oakside Drive
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