Real Estate Investment Properties for Sale in Smithtown, NY
Looking for investment property in Smithtown, NY with high ROI ?
Explore a variety of short-term homes & houses in Smithtown, NY. Invest wisely with VRBO & Smithtown, NY Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.
Investment Property for Sale in Smithtown, NY
| PROPERTY | DETAILS | SALE PRICE | INVESTMENT PERFORMANCE |
|---|---|---|---|
9 Dillmont DrSmithtown, NYSprawling Ranch Situated On A Beautiful Half-Acre Property In The Heart Of Smithtown. This... |
4 beds | 3 baths | 1,870 sq.ft. |
$799,803 |
Airbnb cash on cash: 2.93%
|
2 Vistas CirSmithtown, NYSerene Location! To Be Built. Please Note That Rendering/Photo Shown Conveys Craftsmanship... |
4 beds | 3 baths | 2,600 sq.ft. |
$1,499,000 |
Airbnb cash on cash: 0.66%
|
44 Elizabeth AveSmithtown, NYWelcome to this beautiful, totally renovated expanded Cape offering the perfect blend of s... |
3 beds | 2 baths | 1,578 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.76%
|
14 Sandpiper CtSmithtown, NYNestled on a quiet cul-de-sac, this timeless Colonial offers the perfect blend of comfort,... |
4 beds | 2 baths | 2,590 sq.ft. |
$999,999 |
Airbnb cash on cash: 1.87%
|
6 Keystone CtSmithtown, NYLast Home To Be Built In This Cul-de-sac. Rendering/Photo Shown Conveys Craftsmanship of H... |
4 beds | 3 baths | 2,600 sq.ft. |
$1,550,000 |
Airbnb cash on cash: 2.2%
|
57 Juniper AvenueSmithtown, NYThis is a charming, newly updated Colonial home that offers a blend of modernity and comfo... |
3 beds | 2 baths | 1,800 sq.ft. |
$745,000 |
Airbnb cash on cash: 2.5%
|
17 Erita LaneSmithtown, NYWelcome to 17 Erita Lane in Smithtown. This is the home you have been waiting for. This la... |
4 beds | 3 baths | 2,495 sq.ft. |
$1,199,950 |
Airbnb cash on cash: 1.7%
|
10 Smithtown Blvd #6ASmithtown, NYPRICE REDUCTION, BACK ON MARKET! Welcome to 10 Smithtown Boulevard, Unit 6A, a beautifully... |
1 beds | 1 baths | 820 sq.ft. |
$374,999 |
Airbnb cash on cash: -1.39%
|
57 Birchbrook DrSmithtown, NYLISTING ALSO ON ONE KEY MLS...Delivered vacant...Charming Updated 1900 sq. ft. Expanded 3/... |
3 beds | 2 baths | 1,900 sq.ft. |
$729,888 |
Airbnb cash on cash: 2.4%
|
2 Three Pond RdSmithtown, NYWelcome to this stately and impressive Colonial, ideally situated in one of Smithtown's mo... |
5 beds | 2 baths | 2,788 sq.ft. |
$1,250,000 |
Airbnb cash on cash: N/A
|
43 Hallock AveSmithtown, NYLovely Colonial Split, 3/4 Bedroom (4th Bedroom or Office), Spacious Throughout, Updated E... |
4 beds | 2 baths | 2,029 sq.ft. |
$849,000 |
Airbnb cash on cash: 3.12%
|
26 Stone Gate CtSmithtown, NYMove right into this renovated, Townhouse, with 3-bedrooms, 2.5 bathrooms, full basement, ... |
3 beds | 2 baths | 2,265 sq.ft. |
$830,000 |
Airbnb cash on cash: 1.18%
|
4 Clearbrook DrSmithtown, NYHome Opportunity for Someone that is Handy or wants to Design their Own Home. Beautiful Pi... |
3 beds | 1 baths | 1,300 sq.ft. |
$649,000 |
Airbnb cash on cash: 2.62%
|
20 Veronica CtSmithtown, NYWelcome to 20 Veronica Court, Smithtown - a spacious ranch-style home nestled on a quiet c... |
5 beds | 3 baths | 2,196 sq.ft. |
$725,000 |
Airbnb cash on cash: N/A
|
23 Colonial DrSmithtown, NYWelcome to this stunning custom residence in the highly sought-after Smithtown Pines commu... |
5 beds | 4 baths | 3,800 sq.ft. |
$1,099,988 |
Airbnb cash on cash: N/A
|
106 Summit DrSmithtown, NYGreat Hi Ranch with 2 Sep Living Areas plus Garage, Fenced Yard, Oversize Driveway, Smitht... |
5 beds | 2 baths | 2,100 sq.ft. |
$749,000 |
Airbnb cash on cash: N/A
|
39 Burham DriveSmithtown, NYWelcome to this spacious and well-maintained Colonial located in the heart of Smithtown! S... |
5 beds | 4 baths | 2,565 sq.ft. |
$950,000 |
Airbnb cash on cash: N/A
|
15 Scarborough DriveSmithtown, NYWelcome to this elegant and spacious townhouse in the highly sought-after gated community ... |
3 beds | 3 baths | 1,822 sq.ft. |
$774,999 |
Airbnb cash on cash: 1.47%
|
20 Oak Tree DrSmithtown, NYBeautiful spacious ranch in the desirable Village of the branch. Four beds, 3 full baths. ... |
4 beds | 3 baths | 2,400 sq.ft. |
$1,050,000 |
Airbnb cash on cash: 2.14%
|
589 Landing AveSmithtown, NYNestled at the end of a private long drive shared with only 2 other homes and Not directly... |
5 beds | 2 baths | 3,851 sq.ft. |
$1,626,000 |
Airbnb cash on cash: N/A
|
225 Old Willets PathSmithtown, NYWelcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a profess... |
4 beds | 2 baths | 3,211 sq.ft. |
$1,890,000 |
Airbnb cash on cash: 0.59%
|
19 Knoll LnSmithtown, NYWelcome to 19 Knoll Lane, Smithtown - Where Comfort Meets Elegance Nestled in the heart of... |
4 beds | 2 baths | 2,471 sq.ft. |
$950,000 |
Airbnb cash on cash: 2.74%
|
12 Wayside LaneSmithtown, NYWelcome to 12 Wayside Lane. Beautifully maintained 3-bedroom high ranch. Completely remode... |
3 beds | 2 baths | 1,134 sq.ft. |
$708,000 |
Airbnb cash on cash: 2.19%
|
29 Ivy Hill DrSmithtown, NY29 Ivy Hill Dr, Hauppauge, NY 11787 | Single Family Residential |
4 beds | 2 baths | 2,462 sq.ft. |
$860,000 |
Airbnb cash on cash: 3.15%
|
2 Cindy StreetSmithtown, NYBACK ON MARKET BUYERS FAILED TO PRODUCE - Say Hello To Your New Home! This Colonial Is A T... |
4 beds | 2 baths | 1,900 sq.ft. |
$849,999 |
Airbnb cash on cash: 3.09%
|
106 Morewood DriveSmithtown, NYBeautifully renovated with no expense spared, this stunning four-bedroom, three-bath home ... |
4 beds | 3 baths | 2,100 sq.ft. |
$999,000 |
Airbnb cash on cash: 2.04%
|
7 Monitor RoadSmithtown, NYWelcome to Willow Wood Townhouses - Where Luxury Meets Effortless Living. Perfectly positi... |
3 beds | 3 baths | 1,970 sq.ft. |
$775,000 |
Airbnb cash on cash: 1.81%
|
185 Plymouth BoulevardSmithtown, NYPrestine 4-Bedroom Colonial with FULL BASEMENT in the Smithtown School District! Welcome t... |
4 beds | 3 baths | 2,448 sq.ft. |
$999,000 |
Airbnb cash on cash: 2.2%
|
8 Mulberry DriveSmithtown, NYWelcome to this beautifully updated Hi-Ranch in the desirable Morewood section of Smithtow... |
4 beds | 2 baths | 1,703 sq.ft. |
$799,000 |
Airbnb cash on cash: 3.71%
|
56 Waverly AvenueSmithtown, NYThis house has endless possibilities! It features a large living room, formal dining room,... |
3 beds | 2 baths | 1,684 sq.ft. |
$725,000 |
Airbnb cash on cash: 2.29%
|
28 Dartmouth DrSmithtown, NYDisclaimer: Agent Owned Property Note: Some listing photos have been virtually staged 28 D... |
3 beds | 1 baths | 1,628 sq.ft. |
$762,990 |
Airbnb cash on cash: 2.07%
|
11 Coventry LaneSmithtown, NYWelcome to this stunning Hamptons-style Colonial located within the highly sought-after Sm... |
4 beds | 3 baths | 2,500 sq.ft. |
$929,000 |
Airbnb cash on cash: 2.57%
|
18 Ursular CourtSmithtown, NYWelcome to this beautifully maintained home in the desirable North Smithtown neighborhood,... |
3 beds | 2 baths | 1,730 sq.ft. |
$839,000 |
Airbnb cash on cash: 1.38%
|
23 Whitney GateSmithtown, NY.Welcome to this classic Smithtown Colonial set on a beautiful .66-acre property surrounde... |
4 beds | 3 baths | 2,500 sq.ft. |
$800,000 |
Airbnb cash on cash: 2.68%
|
15 7th AvenueSmithtown, NYBright and cozy 3-bedroom, 3-bath ranch perfectly situated mid-block with beautiful curb a... |
3 beds | 3 baths | N/A |
$799,000 |
Airbnb cash on cash: 1.53%
|
5 Hawkins AvenueSmithtown, NYCharming and beautifully restored, this home seamlessly blends the character of its 1918 o... |
3 beds | 2 baths | 2,000 sq.ft. |
$599,000 |
Airbnb cash on cash: 3.27%
|
79 Brooksite DriveSmithtown, NYWelcome to 79 Brooksite Drive in Smithtown, where privacy, space, and natural beauty come ... |
3 beds | 2 baths | 1,045 sq.ft. |
$699,999 |
Airbnb cash on cash: 2.77%
|
9 Chester StreetSmithtown, NYOpportunity knocks in the heart of Smithtown! This well-maintained 4-bedroom, 2.5-bath col... |
4 beds | 3 baths | 2,041 sq.ft. |
$749,999 |
Airbnb cash on cash: 4.01%
|
58 Cherry LaneSmithtown, NYWelcome to 58 Cherry Lane ~ A beautiful house in a beautiful neighborhood waiting to be yo... |
4 beds | 2 baths | 2,100 sq.ft. |
$875,000 |
Airbnb cash on cash: 3.15%
|
39 Tanglewood DriveSmithtown, NYWelcome to this beautifully renovated 3-bedroom, 1.5-bath ranch nestled in Smithtown and l... |
3 beds | 2 baths | 1,313 sq.ft. |
$679,000 |
Airbnb cash on cash: 2.44%
|
Real Estate investment in Smithtown, NY
There are 128 properties for sale in the city of Smithtown . The median list price in Smithtown is $834,501 and the average price per square foot is $396. In September 2026, the average monthly cash on cash return in Smithtown is 3.00%. The average monthly rental income in Smithtown is $4,329.