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$1,299,000 -$26,000 (-1.96%) Price Reduced

  • For Sale
  • Active
  • Single Family
  • 4 Beds
  • 3 Full Baths
  • 1 Partial Bath
  • 3,000 Sq. Ft.
  • 2 Car Garage
  • Updated 5 days ago
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North Smithtown, Nisseaquogue Overlook Private Sanctuary Where Luxury Meets the Countryside Set against a backdrop of natural beauty, this unique residence offers a rare convergence of 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. The Residence: Step inside to a dramatic, light-filled interior defined by soaring, handcrafted vaulted wood ceilings and refined natural stone detailing that anchors the home in organic elegance. Huge covered brick patio Extensively positioned windows frame sweeping, views of the surrounding woodlands at every turn, combining sophisticated indoor living and the serene outdoors. A private, self-contained 3 room maid or guest suite complete with its own bath for visitors or multi-generational living. 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.

Full Property Details for 135 Oakside Dr

General

  • Price: $1,299,000
  • Taxes: $21,726
  • Status: Active
  • Type: Single Family
  • Source: Long_Island
  • MLS ID: 1041795
  • Updated: 9/25/2026
  • Added to Site: 41 day(s) ago

Interior

  • Number of Rooms: 10
  • Interior Features: First Floor Full Bath, Breakfast Bar, Double Vanity, Eat-in Kitchen, Entrance Foyer, Formal Dining, Granite Counters, High Ceilings, In-Law Floorplan, Open Kitchen, Pantry, Recessed Lighting, Soaking Tub, Walk-In Closet(s), Washer/Dryer Hookup
  • Fireplace: Yes
  • Number of Fireplaces: 1
  • Fireplace(s): Masonry, Wood Burning
  • Appliances: Convection Oven, Dishwasher, Dryer, Electric Cooktop, Electric Oven, Electric Range, Microwave, Refrigerator, Washer, Oil Water Heater
  • Flooring: Carpet, Ceramic Tile, Laminate, Tile

Rooms

Bathrooms

  • Total Bathrooms: 4
  • Full Bathrooms: 3
  • Half Bathrooms: 1

Bedrooms

  • Total Bedrooms: 4

Additional Information

  • Pool: Yes
  • Private Pool: Yes
  • Pool Description: Fenced, Outdoor Pool, Pool Cover, Pool/Spa Combo, Solar Cover
  • Security/Safety: Security System

Exterior

  • Porch/Patio/Deck: Covered, Deck, Patio, Terrace

Parking

  • Garage: Yes
  • Garage Spaces: 2
  • Total Spaces: 6
  • Parking Features: Driveway, Garage, Garage Door Opener, Heated Garage, Off Street, Private

Location

  • County: Suffolk County
  • Subdivision: NISSEAQUOGUE OVERLOOK
  • Neighborhood: Smithtown
  • Cross Streets: Riverview Terrace

School Information

  • High School District: Smithtown
  • Elementary School: Dogwood Elementary School
  • Middle School: Accompsett Middle School
  • High School: Smithtown High School-West

Heating & Cooling

  • Central air: Yes
  • Cooling Type: Central Air, Ductwork
  • Heating Type: Hot Air, Oil

Utilities

  • Sewer: Cesspool
  • Water: Public
  • Utility Description: Cable Available, Electricity Connected, Phone Available, Propane, Water Connected

Structural Information

  • Architectural Style: Chalet
  • Detached/Attached: Detached
  • Construction: Block, Frame, Stone, Wood Siding
  • Basement: Yes
  • Basement Desc.: Walk-Out Access
  • Building Size: 3000
  • Square Feet: 3,000
  • Sq. Ft. Source: Measured
  • Year Built: 1968

Additional Structures

  • Other Structures: Barn(s)

Lot Features

  • Lot Size (Acres): 1.62
  • Lot Size (Sq. Ft.): 70,567
  • Fence: Yes
  • Fencing (Description): Wood

Financial Considerations

  • Tax Amount: $21,726.66

Disclosures and Reports

  • Special Conditions: None
  • Property ID: 0800-035-00-04-00-025-000

Listed by Century 21 Parisi Realty

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Listing agent

— 135 Oakside Dr —

  • Century 21 Parisi Realty

631-669-3900

Get Pre-Approved Today

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Be ready to buy your new home!

with our affiliated lender
NMLS#: 1598647

Get Pre-Approved

Schools serving 135 Oakside Dr

School District:Smithtown Central School District
NameGradesDistance
Smithtown Elementary School
51 Lawrence Avenue, Smithtown, NY 11787
K-52.1 mi
Accompsett Middle School
660 Meadow Road, Smithtown, NY 11787
6-82.6 mi
Smithtown High School West
100 Central Road, Smithtown, NY 11787
9-122.7 mi
Disclaimer: School attendance boundaries provided by ATTOM Data Solutions and are for reference only. Contact the school directly to verify enrollment eligibility.

Price & Sales History for 135 Oakside Dr Get Price Alerts and Save Property

Date
Details
Price
Change
Source
9/25/2026
Price Reduced
$1,299,000
-1.96%
MLS
9/21/2026
Price Reduced
$1,325,000
-1.85%
MLS
9/12/2026
Price Reduced
$1,350,000
-3.5%
MLS
9/08/2026
Price Reduced
$1,399,000
-6.67%
MLS
8/28/2026
Price Reduced
$1,499,000
-14.34%
MLS
8/21/2026
Listed
$1,750,000
—
MLS
Get Price Alerts and Save Property
Disclaimer: Historical sales information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Tax History for 135 Oakside Dr

Year
Property Taxes
Change
Tax Assessment
Change
2024
$20,342
100%
$7,935
—
2020
100%
$7,935
—
2022
-100%
$7,935
-4%
2016
$17,263
-14%
$8,250
—
2020
$20,174
3%
$8,250
—
2018
$19,622
4%
$8,250
—
2017
$18,916
1%
$8,250
—
2016
$18,682
—
$8,250
—
2015
$18,625
9%
$8,250
—
2015
$17,165
2%
$8,250
—
2014
$16,785
-3%
$8,250
—
2013
$17,252
—
$8,250
—
View All
Disclaimer: Historical tax information is derived from public records provided by the county offices. Information is not guaranteed and should be independently verified.

Estimate the Cost for 135 Oakside Dr

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Down Payment
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*These costs are estimates, and the interest rates assume exceptional credit standing.

Listed by Century 21 Parisi Realty

135 Oakside Drive, Smithtown, NY 11787 (MLS# 1041795) is a Single Family property with 4 bedrooms, 3 full bathrooms and 1 partial bathroom. 135 Oakside Drive is currently listed for $1,299,000 and was received on August 21, 2026. Want to learn more about 135 Oakside Drive? Do you have questions about finding other Single Family real estate for sale in Smithtown? You can browse all Smithtown real estate or contact a Coldwell Banker agent to request more information.

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