14 Roundabout Rd, Smithtown, NY 11787
Property image
Property image
OFF MARKET

$829,800

Trulia Estimate
  • 4 Beds
  • 2 Baths
  • 2,236 sqft (on 0.81 acres)

14 Roundabout Rd, Smithtown, NY 11787

The Landing
Est. Refi. Payment $5,633/mo*
Refinance Your Home
Currently Off Market - Sold Nov 25, 1996 for $238,000

Home Value

Trulia Estimate
$830K
Since last month
$300 (0%)
Since last year
Increased$41K (+5.1%)
Since last sale
Increased$591K (+248.4%)
Learn more about this home's value by checking out its Trulia Estimate, the value of nearby homes, and how much similar homes have sold for.

Trulia Estimate

The of this home's value increased by +66% in the last 10 years
MonthEstimated value
2026
August 2026$829K
August 2026$829K
July 2026$829K
June 2026$821K
May 2026$827K
April 2026$801K
March 2026$795K
February 2026$781K
January 2026$773K
2025
2024
2023
2022
2021
2020
2019
2018
2017
2016

Comparable sales

These are recently sold homes that have a similar location or other similar features to this home, like bedrooms, bathrooms, and square footage. Get a sense of the expected prices in the area by viewing these homes.
Address
Distance
Property Type
Sold Price
Sold Date
Bed
Bath
Sqft
45 Woodland Dr, Smithtown, NY
0.08
Single-Family Home
$960,000
07/31/26
5
3
2,537
8 Roundabout Road, Smithtown, NY
0.03
Single-Family Home
$900,000
08/24/26
3
3
1,730
334 Edgewood Avenue, Smithtown, NY
0.37
Single-Family Home
$965,000
06/25/26
4
2
2,119
214 Landing Avenue, Smithtown, NY
0.31
Single-Family Home
$649,000
07/27/26
3
2.5
2,112
330 Edgewood Avenue, Smithtown, NY
0.32
Single-Family Home
$1,003,000
06/26/26
4
2.5
2,546
12 Teapot Lane, Smithtown, NY
0.30
Single-Family Home
$1,300,000
01/08/26
4
3
2,880
58 Cherry Lane, Smithtown, NY
0.60
Single-Family Home
$990,000
08/14/26
4
2
2,100
23 Whitney Gate, Smithtown, NY
0.55
Single-Family Home
$725,500
07/27/26
4
2.5
2,500
21 Kent Place, Smithtown, NY
0.38
Single-Family Home
$915,000
12/19/25
4
2.5
2,500
2 The Spout, Smithtown, NY
0.37
Single-Family Home
$1,200,000
10/09/25
5
3
2,800

Nearby home prices

Get a sense of expected prices in the area by checking the value of nearby homes.
Address
Distance
Price
Bed
Bath
Sqft
Status
8 Roundabout Road, Smithtown, NY 11787
0.03
$900,000
3
3
1,730
Recently Sold
7 Bridle Path Rd, Smithtown, NY 11787
0.07
$1,044,200
3
3.5
-
Off Market
45 Woodland Dr, Smithtown, NY 11787
0.08
$960,000
5
3
2,537
Recently Sold
8 Bridle Path Road, Smithtown, NY 11787
0.10
$1,006,200
4
3
2,107
Off Market
18 Bridle Path Road, Smithtown, NY 11787
0.18
$845,000
4
2
-
Off Market
12 Blydenburg Avenue, Smithtown, NY 11787
0.16
$1,022,400
4
3
-
Off Market
234 Edgewood Avenue, Smithtown, NY 11787
0.16
$975,000
5
4
4,307
Recently Sold
20 Bridle Path Road, Smithtown, NY 11787
0.21
$774,600
3
2
2,396
Off Market
90 Blydenburg Avenue, Smithtown, NY 11787
0.23
$820,000
5
3
2,200
Recently Sold
14 Gazebo Lane #14, Smithtown, NY 11787
0.22
$408,300
2
2
1,102
Off Market
53 Bellemeade Avenue, Smithtown, NY 11787
0.25
$701,400
4
2
-
Off Market
39 Roundabout Road, Smithtown, NY 11787
0.26
$1,047,000
3
2
1,800
Off Market

Local Information

  • Map ViewExplore the area around 14 Roundabout Rd.
  • Schools1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Home Highlights

Property Type
Single-Family Home
Year Built
1954
Lot Size
0.81 acres
Living Area
2,236 sqft
Price/Sqft
$371
Parking
Garage

About this House

Desirable N. Smithtown'home Sweet Home'warm & Welcoming Farm Ranch Home On Gorgeous Private Parklike .81 Acre. 4 Bdrms, 2 Updated Baths,New Paint,Roof, Siding, Windows, Hardwd Floors,Custom Molding Thru Out,Hi Hats,Livingrm W/ Marble F/P,Den Off Kitchen, Sunroom And Enclosed Screened Porch.Updated Burner &Hw Heater,Finished Bsmt,Extended Belgium Blk Drvway.Ready To Move In
14 Roundabout Rd, Smithtown, NY 11787 is a 4 bedroom, 2 bathroom, 2,236 sqft single-family home in The Landing, built in 1954. It last sold for $238,000 on Nov 25, 1996. This property is not currently displayed as for sale or rent on Trulia. The Trulia Estimate is $829,800, with a rent estimate of $4,143/month.

Home Details for 14 Roundabout Rd

Interior Features

Levels, Entrance, & Accessibility
Stories: 1.5

Property Information

Year Built
Year Built: 1954
Property Type / Style
Property Type: Single Family HomeArchitecture: Cape Cod

Exterior Features

Exterior Home Features
Exterior: Composition
Parking & Garage
GarageParking: Garage Attached

Community

Units in Building: 1

Lot Information

Lot Area: 0.81 acres

Price and Tax history

DateEventPrice
Nov 21, 2008
Source: Agent Provided
ListingRemoved
$539,990
Sep 29, 2008
Source: Agent Provided
Listed For Sale
$539,990
Nov 25, 1996
Source: N/A
Sold
$238,000

Market trends in Smithtown

Last updated July 2026
Buyer'sMarketSeller'sMarket
Avg. sale price
$808K
$4.33KMoM
Sale-to-List Price
—
Price per sq ft
—
Available listings
102
20MoM

Around this home

Neighborhood Overview

The Landing
See Local Highlights
Neighborhood stats provided by third party data sources.

LGBTQ Local Legal Protections

Frequently asked questions about 14 Roundabout Rd

  • What is 14 Roundabout Rd estimated to be worth?
    Trulia's estimated value for 14 Roundabout Rd in Smithtown, NY is $829,800.
  • What is the price history for 14 Roundabout Rd?
    14 Roundabout Rd in Smithtown, NY last sold for $238,000 in November 1996.
  • Is Smithtown a buyer's or seller's market?
    Smithtown is currently a seller's market, based on recent for-sale activity.
  • What's the median sale price in Smithtown?
    The median sale price in Smithtown is $808K. That is up $4.33K from the prior month.
  • How big is the lot at 14 Roundabout Rd?
    The lot at 14 Roundabout Rd in Smithtown, NY is about 0.81 acres (35,283 sq ft).
  • Does 14 Roundabout Rd have a garage?
    Yes, 14 Roundabout Rd in Smithtown, NY has a garage.

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