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Residential Land with Home for Sale in Smithtown, New York

109 Oakside Dr, Smithtown, NY 11787

$1,450,000
2 acres
Active
$50k drop
Est $9,553/mo

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.

2,400
Sq feet
4
Beds
3
Full baths
1
1/2 bath
1960
Built

Location

Street address
109 Oakside Dr
School district
Smithtown
Elevation
142 feet
Coordinates
40.8799, -73.2038

Directions

Landing Avenue to Oakside Drive

Property details

Acreage
2 acres
MLS #
MLSLI 915379
Posted

Property taxes

2025
$29,386

Parcels

  • 0800-035-00-04-00-036-000

Details and features

Listing

Type
Residential
Subtype
Single Family Residence
Franchise
Century 21 Real Estate

Exterior

Structures
Arena

Structure

Style
Ranch
Basement
Finished
Water
Public
Sewer
Cesspool
Heating
Hot Water, Oil
Cooling
Central Air
Materials
Vinyl Siding

Interior

Room Count
7
Rooms
Basement, Bathroom x 4, Bedroom x 4, Dining Room
Appliances
Dishwasher, Dryer, Electric Cooktop, Electric Oven, Microwave, Refrigerator
Features
Eat-In Kitchen, Entrance Foyer, First Floor Bedroom, First Floor Full Bath, Formal Dining, Granite Counters

Nearby schools

NameLevelDistrictDescription
Accompsett Elementary SchoolElementarySmithtown
Accompsett Middle SchoolMiddleSmithtown
Smithtown High School-WestHighSmithtown

Listing history

DateEventPriceChangeSource
Oct 26, 2025Price drop$1,450,000$49,990 -3.3%MLSLI
Sept 21, 2025New listing$1,499,990MLSLI
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This 2-acre property is located at 109 Oakside Dr in Smithtown, NY 11787. The property is available for sale for $1,450,000. It has a 2,400 sq ft 4 bedroom, 3 bath house built in 1960.

Checked 15 mins ago — Updated

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