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$1,298,000

135 Oakside Dr

Smithtown, NY
Active
4
Bedrooms
3.5
Bathrooms
3,300
Square Feet
1.62
Lot Size (acres)
1968
Year Built
58
Days On Market

North Smithtown, Nisseaquogue Overlook Private Sanctuary Where Luxury Meets the Countryside Set against a backdrop of natural beauty, this unique residence offers architectural character, privacy, and equestrian capability. .As you approach via the impressive circular driveway—complemented by three generous additional driveways for effortless guest parking and trailer access—the estate-like scale of the property immediately unfolds. Step inside to a dramatic, light-filled interior defined by soaring, handcrafted vaulted wood ceilings and refined natural stone. The windows frame sweeping, views of the surrounding woodlands at every turn, combining sophisticated indoor living and the serene outdoors A private, self-contained guest suite complete with its own bath for multi-generational living.(With Mother daughter permit from the town) The Horse Facilities: The property features a dedicated equestrian setup including an intimate functional small barn and an adjacent tack room with views of the Nissequogue River landscape. This is more than a home; it is an exceptional legacy property offering, seclusion, natural splendor, and timeless craftsmanship. Arrange a showing today.

Listing Information

Listing Updated
2 days ago
Listed By
Richard Parisi C2EX · Century 21 Parisi Realty, 6316693900
MLS#
1041795
Source
OneKey MLS
Status
Active

Facts & Features

Location

Community Information

Address
135 Oakside Dr, Smithtown, NY 11787
City
Smithtown
County
Suffolk
Neighborhood
NISSEAQUOGUE OVERLOOK
Zip Code
11787

Architecture

Bedrooms
4
Bathrooms
3.5
Year Built
1968
Style
Chalet
Construction Materials
Wood Siding, Frame, Stone, Block
Building Area
3,300 sq. ft.
Garage
Yes
Garage Spaces
2
Parking Features
Driveway, Private, Garage Door Opener, Garage, Off Street, Heated Garage

Features & Amenities

Interior Features
Eat-in Kitchen, Walk-In Closet(s), Pantry, In-Law Floorplan, Granite Counters, Breakfast Bar, Double Vanity, Recessed Lighting, High Ceilings, Entrance Foyer, Soaking Tub
Appliances
Dryer, Dishwasher, Electric Range, Microwave, Refrigerator, Washer, Convection Oven, Electric Oven, Electric Cooktop
Flooring
Laminate, Tile, Carpet, Ceramic Tile
Patio and Porch
Covered, Patio, Deck, Terrace
Cooling
Central Air
Heating
Oil

Property Features

Lot Size
1.62 Acres
Water
Public
Sewer
Cesspool
Utilities
Cable Available, Electricity Connected, Water Connected, Phone Available, Propane

Square Footage

Total
3,300 sq. ft.

Tax & Financial Information

List Price
$1,298,000
Annual Taxes
$21,726

Schools

61/100
Dogwood Elementary School
Elementary · Grades KG–05 · 2 mi
Assigned school for this home
City
Smithtown
Students
350
Student–teacher
12.5
Student body
80% White · 13% Hispanic / Latino · 3% Asian
Free/reduced lunch
13%
Phone
(631) 382-4255
52/100
Accompsett Middle School
Middle · Grades 06–08 · 2.6 mi
Assigned school for this home
City
Smithtown
Students
577
Student body
79% White · 11% Hispanic / Latino · 5% Asian
Free/reduced lunch
10%
Phone
(631) 382-2305
75/100
Smithtown High School-West
High · Grades 09–12 · 2.7 mi
Assigned school for this home
City
Smithtown
Students
1,573
Parent reviews
5.0★ avg · 2 reviews
Student body
83% White · 9% Hispanic / Latino · 6% Asian
Free/reduced lunch
10%
Phone
(631) 382-2905
100/100
Mills Pond Elementary School
Elementary · Grades KG–05 · 3 mi
City
Saint James
Students
445
Student body
82% White · 8% Asian · 7% Hispanic / Latino
Free/reduced lunch
8%
Phone
(631) 382-4305
75/100
Accompsett Elementary School
Elementary · Grades KG–05 · 2.5 mi
City
Smithtown
Students
570
Parent reviews
5.0★ avg · 2 reviews
Student body
84% White · 10% Hispanic / Latino · 2% Two or More Races
Free/reduced lunch
8%
Phone
(631) 382-4155
56/100
Smithtown Elementary School
Elementary · Grades KG–05 · 2.1 mi
City
Smithtown
Students
493
Student body
70% White · 21% Hispanic / Latino · 6% Asian
Free/reduced lunch
17%
Phone
(631) 382-4505
53/100
Saint James Elementary School
Elementary · Grades KG–05 · 2 mi
City
Saint James
Students
464
Student body
77% White · 15% Hispanic / Latino · 4% Two or More Races
Free/reduced lunch
16%
Phone
(631) 382-4455
52/100
Smithtown High School East
High · Grades 09–12 · 1.8 mi
City
Saint James
Students
1,428
Student body
79% White · 11% Hispanic / Latino · 8% Asian
Free/reduced lunch
12%
Phone
(631) 382-2705

School ratings are provided for informational purposes only and are subject to change. Attendance boundaries are for reference only — contact the school or district directly to verify enrollment eligibility.

Historical Data

Price History

DateEventPrice
10/15/2026Price change$1,298,000
08/21/2026Listed for sale$1,750,000

Listed by Richard Parisi C2EX · Century 21 Parisi Realty · 6316693900

Listing information provided exclusively for consumers' 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 deemed reliable but not guaranteed by the MLS. The listing broker’s offer of compensation is made only to participants of the MLS where the listing is filed. Copyright 2026, OneKey MLS. All rights reserved.

Last Updated: October 15, 2026 at 1:44 PM | Source: OneKey MLS | MLS#: 1041795

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