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 |
|---|---|---|---|
45 Grandview LaneSmithtown, NYLARGE 4 BEDROOM 2.5 BATH COLONIAL ON 1.23 ACRES OF PARKLIKE PROPERTY IN THE PINES SECTION ... |
4 beds | 3 baths | 2,924 sq.ft. |
$999,999 |
Airbnb cash on cash: 2.54%
|
234 Edgewood AvenueSmithtown, NYMassive Expanded Ranch Retreat on 1.3 Acres in Smithtown offers unmatched space, flexibili... |
5 beds | 4 baths | 4,307 sq.ft. |
$949,999 |
Airbnb cash on cash: N/A
|
105 Lone Oak PathSmithtown, NYBeautifully situated in The Pines of Smithtown, this charming 3-bedroom, 2-bath Colonial w... |
3 beds | 2 baths | N/A |
$829,000 |
Airbnb cash on cash: 1.76%
|
61 Redan DriveSmithtown, NYLove Where You Live While Enjoying a Carefree Life Style in this Prestigious Gated Golf Co... |
3 beds | 3 baths | 2,740 sq.ft. |
$1,185,000 |
Airbnb cash on cash: 0.01%
|
2 Vistas CircleSmithtown, NYSerene Location! To Be Built. Please Note That Rendering/Photo Shown Conveys Craftsmanship... |
4 beds | 4 baths | 2,600 sq.ft. |
$1,499,000 |
Airbnb cash on cash: 0.66%
|
15 Format LaneSmithtown, NYSituated at 15 Format Lane in the heart of Smithtown, this home invites you to explore its... |
4 beds | 3 baths | 2,535 sq.ft. |
$850,000 |
Airbnb cash on cash: 3.21%
|
79 Oakside RoadSmithtown, NYWelcome to 79 Oakside Road, a custom-built haven nestled in the heart of Smithtown, NY. Bu... |
4 beds | 3 baths | 2,800 sq.ft. |
$1,249,990 |
Airbnb cash on cash: 1.58%
|
40 Friendly RoadSmithtown, NYWelcome to 40 Friendly Rd. A home that redefines style, comfort, and convenience. This tur... |
5 beds | 4 baths | 2,700 sq.ft. |
$1,675,000 |
Airbnb cash on cash: N/A
|
158 Landing Meadow RoadSmithtown, NYWelcome to 158 Landing Meadow Road! Renovated on 1.2 Acres With Pool and Luxury Finishes! ... |
4 beds | 4 baths | 3,900 sq.ft. |
$1,790,000 |
Airbnb cash on cash: 0.84%
|
339 Forest LaneSmithtown, NYLow taxes and Hauppauge school district! Charming Cape cod on private 1/2 acre of fully f... |
3 beds | 2 baths | 1,080 sq.ft. |
$649,999 |
Airbnb cash on cash: 3.47%
|
44 Elizabeth AvenueSmithtown, NYAdorable Cape with so much potential. 2 Bedrooms up and 2 Bedrooms downstairs. Large Eat I... |
4 beds | 2 baths | N/A |
$520,000 |
Airbnb cash on cash: 6.88%
|
26 LindnerSmithtown, NYWelcome to this updated 4-bedroom, 3-bath ranch nestled on a spacious 1-acre lot in the hi... |
4 beds | 3 baths | 1,785 sq.ft. |
$725,000 |
Airbnb cash on cash: 4.23%
|
16 Wildwood LaneSmithtown, NYHouse For Sale. |
5 beds | 3 baths | 2,204 sq.ft. |
$850,000 |
Airbnb cash on cash: N/A
|
24 Ursular CourtSmithtown, NYDonât miss this opportunity! Back on market buyer lost financing! Welcoming Unique! Sun-... |
3 beds | 2 baths | 2,167 sq.ft. |
$759,999 |
Airbnb cash on cash: 1.61%
|
24 Croft LaneSmithtown, NYExperience the Ultimate Equestrian Lifestyle With This Stunning Expanded Ranch Home and Ho... |
5 beds | 4 baths | 2,600 sq.ft. |
$1,179,000 |
Airbnb cash on cash: N/A
|
147 Juniper AvenueSmithtown, NYWelcome to 147 Juniper Avenue in Smithtown, a beautifully updated ranch-style home that co... |
3 beds | 2 baths | 1,500 sq.ft. |
$739,000 |
Airbnb cash on cash: 2.1%
|
25 Whispering Woods DriveSmithtown, NYThis Gorgeous 4 Bedroom, 2.5 Bath Colonial In The Beautiful Enchanted Woods Section Of Smi... |
4 beds | 3 baths | N/A |
$999,999 |
Airbnb cash on cash: 1.69%
|
62 Laurel DriveSmithtown, NYFabulous ranch!!! Summer is coming and this oasis is waiting for YOU! Gorgeous home decora... |
3 beds | 3 baths | 2,000 sq.ft. |
$1,299,000 |
Airbnb cash on cash: 0.73%
|
6 Keystone CourtSmithtown, NYLast Home To Be Built In This Cul-de-sac. Rendering/Photo Shown Conveys Craftsmanship of ... |
4 beds | 4 baths | 2,600 sq.ft. |
$1,550,000 |
Airbnb cash on cash: 2.2%
|
Lot 21 Hurtin BoulevardSmithtown, NYNEW CONSTRUCTION-To Be Built- 4/5 Bedroom 3 bathrooms, Colonial 2 Car Garage, 4/5 Bedrooms... |
5 beds | 3 baths | 3,100 sq.ft. |
$1,090,000 |
Airbnb cash on cash: N/A
|
29 Bayberry LaneSmithtown, NYConstruction has begun!! Still time to customize!! Great opportunity to be in The Pines!! ... |
4 beds | 3 baths | 2,600 sq.ft. |
$1,195,000 |
Airbnb cash on cash: 1.56%
|
1 Charter LaneSmithtown, NYCome see this charming home now on the market! This home has Fresh Interior Paint. Discove... |
3 beds | 3 baths | 2,144 sq.ft. |
$779,000 |
Airbnb cash on cash: 1.65%
|
3 Ingram CourtSmithtown, NYNestled on a serene dead-end court in the sought-after Village of the Branch, this spaciou... |
4 beds | 4 baths | 2,977 sq.ft. |
$978,888 |
Airbnb cash on cash: 2.46%
|
36 Rose StreetSmithtown, NYWelcome to this delightful 3-bedroom colonial home located in the Kings Park School Distri... |
3 beds | 3 baths | 1,528 sq.ft. |
$599,999 |
Airbnb cash on cash: 2.87%
|
2 Windmill CourtSmithtown, NYNestled in the heart of the Village of the Branch in Smithtown, this beautifully updated C... |
4 beds | 3 baths | 3,000 sq.ft. |
$899,999 |
Airbnb cash on cash: 2.48%
|
9 AnnetteSmithtown, NYWelcome home to this cozy ranch situated on 0.220 acre. Home offers 2 Bedrooms 1 full bath... |
2 beds | 1 baths | 9,583 sq.ft. |
$525,000 |
Airbnb cash on cash: -0.1%
|
9 Cresthill PlaceSmithtown, NYWelcome to this meticulously cared-for 4-bedroom, 3-bath Colonial nestled on an expansive ... |
4 beds | 3 baths | 2,278 sq.ft. |
$889,999 |
Airbnb cash on cash: 2.91%
|
60 Tanglewood DriveSmithtown, NYNestled at 60 Tanglewood Dr in Smithtown, NY, this charming home offers a fantastic locati... |
3 beds | 1 baths | N/A |
$649,999 |
Airbnb cash on cash: 3.13%
|
46 W Pond CourtSmithtown, NYRARE Opportunity ~ Corner Emory Ranch ~ One Story, 2 Bedroom, 2 Bathroom meticulously main... |
2 beds | 2 baths | 1,440 sq.ft. |
$625,000 |
Airbnb cash on cash: -1.63%
|
2 Hayloft CourtSmithtown, NYWelcome to this Breathtaking Home located in the Yellow Top Estates Neighborhood of Smitht... |
5 beds | 4 baths | 3,531 sq.ft. |
$1,699,000 |
Airbnb cash on cash: N/A
|
25 Glacier DriveSmithtown, NYGem of the Neighborhood! Immaculate Colonial-styled Splanch in the National Blue Ribbon Co... |
4 beds | 3 baths | 2,108 sq.ft. |
$899,000 |
Airbnb cash on cash: 3.12%
|
9 Graystone LaneSmithtown, NYWelcome to 9 Graystone Lane - An Entertainers Delight!! This beautiful 4 bed, 2.5 bath col... |
4 beds | 3 baths | 3,264 sq.ft. |
$869,000 |
Airbnb cash on cash: 2.89%
|
206 Brooksite DriveSmithtown, NYLovely Smithtown Living! Enjoy This Beautifully Designed and Maintained Home Which Feature... |
4 beds | 4 baths | 3,000 sq.ft. |
$1,100,000 |
Airbnb cash on cash: 2.2%
|
4 Candlelight CourtSmithtown, NYWelcome to this Custom Contemporized Colonial W/ Two Story Entrance Foyer, Vaulted Ceiling... |
3 beds | 3 baths | 2,922 sq.ft. |
$885,000 |
Airbnb cash on cash: 0.59%
|
36 Woodland LaneSmithtown, NYInviting, Peaceful, Warm And Immaculate, A Few Words To Describe The Home Youâve Been Lo... |
5 beds | 3 baths | 2,850 sq.ft. |
$1,175,000 |
Airbnb cash on cash: N/A
|
44 Croft LaneSmithtown, NYWelcome to 44 Croft Lane located in the Smithtown Pines section of Smithtown! A stunning C... |
3 beds | 4 baths | 3,197 sq.ft. |
$1,175,000 |
Airbnb cash on cash: 0.14%
|
40 Dillmont DriveSmithtown, NYWelcome home to this absolutely spectacular dream home nestled on just shy of an acre of l... |
5 beds | 3 baths | 2,580 sq.ft. |
$849,999 |
Airbnb cash on cash: N/A
|
4 Nadia CourtSmithtown, NYWelcome to 4 Nadia Court, a custom-designed 5 bedroom, 4.5 bath masterpiece nestled in on... |
5 beds | 5 baths | 4,677 sq.ft. |
$2,049,000 |
Airbnb cash on cash: N/A
|
10 Marlan CourtSmithtown, NYOpportunity knocking here for the chance to live in a very desirable location on a cul de ... |
3 beds | 2 baths | 2,402 sq.ft. |
$649,990 |
Airbnb cash on cash: 2.36%
|
22 ChurchillSmithtown, NYWelcome to this exceptional custom-built modern luxury home, located in the highly desirab... |
5 beds | 4 baths | 5,333 sq.ft. |
$1,349,000 |
Airbnb cash on cash: N/A
|
Real Estate investment in Smithtown, NY
There are 68 properties for sale in the city of Smithtown . The median list price in Smithtown is $887,500 and the average price per square foot is $323. In September 2025, the average monthly cash on cash return in Smithtown is 3.00%. The average monthly rental income in Smithtown is $4,800.