27 Roundabout Rd
Smithtown, NY 11787
The Landing
3 Beds
2 Baths
2,272 sqft (on 0.77 acres)
3 Beds
2 Baths
2,272 sqft
(on 0.77 acres)
Local Information
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Description
Charming Farmranch In Smithtown Sd,Set On Very Private.77 Of An Acre.Beautiful F/Lvgrm W/Fplc & Custom Cherry Builtins,Oversized Fdr,Eik- W/Fplc,Den,Laundry Rm, 3Bdrm, 2 Fbaths,Hardwood Flrs.Thruout, 2 Sep. Patios, Large 2Car Grge With Sep. Basemnt Ent. 5 Zone Heat W/ Buderus Boiler, Cac
This property is off market, which means it's not currently listed for sale or rent on Trulia. This may be different from what's available on other websites or public sources.
Home Highlights
Parking
Garage
Outdoor
No Info
A/C
Heating & Cooling
HOA
None
Price/Sqft
No Info
Listed
Less than a day ago
Home Details for 27 Roundabout Rd
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Heating & Cooling Heating: Other, OtherAir ConditioningCooling System: CentralHeating Fuel: Other |
Levels, Entrance, & Accessibility Stories: 2 |
Interior Details Number of Rooms: 7Types of Rooms: Dining Room, Family Room |
Appliances & Utilities DishwasherDryerRefrigeratorWasher |
Fireplace & Spa Fireplace |
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Exterior Home Features Roof: OtherExterior: Wood |
Parking & Garage GarageParking: Garage Attached |
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Year Built Year Built: 1957 |
Property Type / Style Property Type: Single Family HomeArchitecture: Ranch / Rambler |
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Units in Building: 1 |
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Lot Area: 0.77 acres |
Price History for 27 Roundabout Rd
| Date | Price | Event | Source |
|---|---|---|---|
| 06/25/2014 | $500,000 | Sold | OneKey® MLS as distributed by MLS GRID #L2637686 |
| 02/09/2014 | $509,000 | ListingRemoved | Agent Provided |
| 01/03/2014 | $509,000 | PriceChange | Agent Provided |
| 10/05/2013 | $539,000 | Listed For Sale | Agent Provided |
Market trends in Smithtown
Last updated April 2026
Avg. sale price
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Sale-to-List Price
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Price per sq ft
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Available listings
65 14MoM
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Property Tax and Assessment
| Year | 2025 |
|---|---|
| Tax | |
| Assessment | $998,750 |
Home facts updated by county records
Comparable Sales for 27 Roundabout Rd
Address | Distance | Property Type | Sold Price | Sold Date | Bed | Bath | Sqft |
|---|---|---|---|---|---|---|---|
0.19 | Single-Family Home | $982,000 | 06/18/25 | 3 | 2 | 1,800 | |
0.20 | Single-Family Home | $620,000 | 12/31/25 | 4 | 2.5 | 2,546 | |
0.17 | Single-Family Home | $1,300,000 | 01/08/26 | 4 | 3 | 2,880 | |
0.23 | Single-Family Home | $950,000 | 08/08/25 | 4 | 3 | 2,107 | |
0.24 | Single-Family Home | $658,000 | 12/03/25 | 3 | 2 | 1,300 | |
0.23 | Single-Family Home | $1,200,000 | 10/09/25 | 5 | 3 | 2,800 | |
0.07 | Single-Family Home | $975,000 | 01/23/26 | 5 | 4 | 4,307 | |
0.39 | Single-Family Home | $915,000 | 12/19/25 | 4 | 2.5 | 2,500 | |
0.66 | Single-Family Home | $950,000 | 02/17/26 | 3 | 2 | 1,706 | |
0.80 | Single-Family Home | $755,000 | 08/26/25 | 3 | 2 | 2,127 |
Nearby homes
Get a sense of prices in the area by checking nearby homes.
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Assigned Schools
These are the assigned schools for 27 Roundabout Rd.
- Smithtown High School West
- 9-12
- Public
- 1158 Students
9/10GreatSchools RatingParent Rating AverageThis is literally the worst school, everyday I come here I feel drained and miserable and the staff are a bunch of old miserable people. There’s like 4 teachers I actually like and I know care about there students. When you are a teacher you can’t not like kids and it’s obviously half the staff here DOES NOT like children. 1/10 for this school.Student Review5y ago - Smithtown Elementary School
- K-5
- Public
- 517 Students
6/10GreatSchools RatingParent Rating AverageOur 3 children have gone and still attend Smithtown Elementary. The entire staff has been nothing but the best. Our 3 kids flourished at this school while getting the individual attention they needed. The school is clean, the grounds are beautiful, the playground is brand new. All of the teachers have been excellent, attentive, and communicative.Parent Review1y ago - Accompsett Middle School
- 6-8
- Public
- 522 Students
5/10GreatSchools RatingParent Rating AverageThe teachers are very compassionate about trying to provide the best learning experiences for all children regardless of their capabilities. This is also the ESL magnet school for the district and the students are made to feel welcomed.Parent Review5y ago 
Check out schools near 27 Roundabout Rd.
Neighborhood Overview
Neighborhood stats provided by third party data sources.
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0.66 ACRESListing by: Realty Connect USA L I Inc- OPEN FRI, 5-7PMCOMING SOON 6/110.5 ACRESListing by: Coldwell Banker American Homes
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27 Roundabout Rd, Smithtown, NY 11787 is a 3 bedroom, 2 bathroom, 2,272 sqft single-family home built in 1957. 27 Roundabout Rd is located in The Landing, Smithtown. This property is not currently available for sale. 27 Roundabout Rd was last sold on Jun 25, 2014 for $500,000. The current Trulia Estimate for 27 Roundabout Rd is $971,000.