- 3
- beds
- 1 full · 1 half
- baths
- 1848
- year built
- Status:
- Coming Soon
- MLS #:
- 1070587
- County:
- Suffolk
- Listed By:
- Jessica L. Stanco AHWD PSA - Howard Hanna Coach
- Office Phone:
- (631) 757-4000
- Agent Email:
- jstanco@coachrealtors.com
Sponsoring Broker: Steven Domber, Berkshire Hathaway HomeServices Hudson Valley Properties
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, 202612:00pm - 2:00pm
1st Weekend Open House for this Renovated Farmhouse Style Home! Come check out the River View too!
-
November 15, 202612:30pm - 2:30pm
1st Weekend Open House for this Renovated Farmhouse Style Home! Come check out the River View too!
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
-
Nearby Schools
-
54out of 100
Public School for 143 Oakside Dr, Smithtown, NY 11787
Grades: Elementary
Distance: 2.2 mi
-
52out of 100
-
50out of 100
-
53out of 100
-
54out of 100
-
53out of 100
-
60out of 100
-
50out of 100
-
53out of 100
-
75out of 100
Disclaimer: ez Home Search School Ratings are on a scale of 1-100 and represent our evaluation of school quality based on academic performance, school resources, community feedback, and demographic factors. School attendance boundaries are for reference only. Contact the school directly to verify enrollment eligibility.
-
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Price History
| 11/11/2026 | Coming Soon | $875,000 |
| Source: OneKey MLS #1070587 | ||
Source: MLS Data
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There are currently 101 properties available in Smithtown, with 0 under contract to close soon. Properties in the city have an average sale price of $0 and typically spend 118 days on the market before being sold.
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Source: ez Home Search, MLS Data
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.
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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.
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How do I get pre-approved to buy 143 Oakside Dr?
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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?
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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
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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
