Searching ...

Historic charm meets modern farmhouse living in a tranquil setting with a view of the Nissequogue River. Perched on a full acre, this special property offers a peaceful connection to nature, with deer, wild turkeys, and other wildlife making frequent appearances. Built in the late 19th century as a servants’ cottage for the Kenyon Estate, the home blends its distinctive past with extensive updates completed within the last two years. A fabulous farmhouse kitchen offers abundant counter space and opens to the dining area, while two beautifully renovated bathrooms carry the modern farmhouse style throughout. A unique third bedroom, also ideal as a separate home office, awaits finishing, with materials included in the sale. Extensive improvements include all-new plumbing, two-zone heating and central air, new 200-amp electric service, roof, and Andersen windows. A renovated inground pool adds to the outdoor enjoyment. This special location affords homeowners a peaceful retreat with everyday conveniences close by. Enjoy beach rights to multiple Town of Smithtown beaches, boat ramp access, and nearby hiking trails, parks, nature preserves, and golf courses. Main Street’s restaurants and shops are just moments away, with convenient access to the LIRR and parkways. A rare opportunity to own a piece of history in a setting that feels like a retreat.

Open House

  • November 14, 2026
    12:00pm - 2:00pm
  • November 15, 2026
    12:30pm - 2:30pm

This open house information was last updated on 11/11/2026 07:33PM

  • Bedrooms
    3
  • Bathrooms
    1 full · 1 half
  • Year Built
    1848
  • Architectural Style
    Colonial
  • Construction Materials
    Frame, Clapboard
  • Parking Features
    Driveway
  • Interior Features
    Eat-in Kitchen, Walk-In Closet(s), Recessed Lighting
  • Appliances
    Dryer, Dishwasher, Electric Range, Electric Water Heater, Refrigerator, Washer, Stainless Steel Appliance(s)
  • Flooring
    Laminate
  • Patio And Porch
    Patio, Porch
  • Pool Features
    Fenced, In Ground, Pool Cover, Private
  • Security Features
    Smoke Detector(s), Security System
  • Cooling
    Central Air
  • Heating
    Forced Air, Oil
  • Basement
    Unfinished, Storage Space

  • Acres
    1.0
  • Lot Features
    Sprinklers In Front, Back Yard, Front Yard
  • View
    River
  • Utilities
    Cable Available, Electricity Connected, Water Connected, Phone Available
  • Water
    Public

  • County
    Suffolk
  • City
    Smithtown
  • Zip Code
    11787
  • High School
    Smithtown High School-West
  • Middle School
    Accompsett Middle School
  • Elementary School
    Smithtown Elementary School

Ask a Question

What's your home worth?

Calculate your current home value within seconds.

Frequently Asked Questions

How do I schedule a tour of 143 Oakside Dr?

We can make that happen quickly. Click Tour This Home and we'll connect you directly with our vetted local partner to schedule your visit to 143 Oakside Dr.

They know residentials in the area well and can give you the guidance you need to buy with confidence.

How do I get more information about 143 Oakside Dr?

Click Ask a Question to talk with our team. You already know it is a 3 bed, 1 bath, listed for $875,000. We can talk through recent upgrades, potential seller motivation, how this single family residence compares to others in Smithtown, and can even get you in to see the property quickly.

Are there any upcoming open houses for this property?

Yes—an open house is scheduled for . Let us connect you with our local expert before you go so they can help you prepare questions, highlight key features, and arrange a private tour if that time doesn't work.

How much is the monthly mortgage payment for 143 Oakside Dr?

With a 20% down payment and a 30-year fixed loan at an illustrative 7.25% rate, the ez Mortgage Calculator estimates the monthly payment for 143 Oakside Dr at around $6,157. This includes estimated property taxes and insurance.

Want to see how this changes with different down payments or interest rates? Jump to the calculator to run the numbers and fine-tune your plan.

How do I get pre-approved to buy 143 Oakside Dr?

Stand out in a competitive market by getting pre-approved today. Our quick and private pre-approval process helps you understand your true buying power—no credit pull required to explore all of your options.

Or, let us connect you with our preferred local lender in Suffolk County. They will give you all of your available financing options, based on your specific situation and what is available to you.

Can I negotiate the asking price for 143 Oakside Dr?

In most cases, yes. Whether 143 Oakside Dr is priced competitively or not, your best offer depends on your personal situation, the seller's timeline, and recent activity in Smithtown's market. Our preferred local partner will help you craft a strategy—factoring in comparable properties that have sold, timing, and deal structure—to make a smart, strong offer. Click here to ask about negotiation opportunities.

How do I make an offer on 143 Oakside Dr?

We can handle that for you. Our preferred local agent specializes in residentials in Smithtown and can guide you through every step of the offer process.

You need an expert who is looking out for your best interests. From market valuation to contingencies and timing, they'll help you present a compelling offer that fits your goals. Click Ask a Question to get started today.

How long has this property been on the market?

143 Oakside Dr was listed on November 11, 2026, which means it's been on the market for 0 days.

Want to keep tabs on it? Click the ♥ to favorite this home and get notified of price drops or changes.

When was this house built?

This home was built in 1848, making it approximately 178 years old.

What is the lot size of this property?

143 Oakside Dr sits on a 1.0-acre lot, which is 43,560 square feet.

What schools are assigned to this property?

Based on MLS info, this home is zoned for:

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

Want to see how these schools compare? Check out our Suffolk County School Guide to see ratings, reviews, and more for the schools in the area.

What are the property taxes for 143 Oakside Dr?

The most recent public record shows annual property taxes for 143 Oakside Dr were approximately $14,136. This may change with reassessment or exemptions. Our local partner can verify current tax amounts and help you estimate future costs based on your situation.

Is 143 Oakside Dr still available for sale?

Source: ez Home Search, MLS Data

Popular Home Searches in Smithtown, NY


Search Nearby Cities


Search Nearby Postal Codes

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: November 11, 2026 at 08:26PM | Source: OneKey MLS | MLS#: 1070587