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%
|
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%
|
210 Landing AvenueSmithtown, NYWelcome to this very private Cape Cod style home up on a hilltop overlooking Landing Ave l... |
3 beds | 2 baths | 1,300 sq.ft. |
$699,000 |
Airbnb cash on cash: 2.96%
|
203 Pond View LaneSmithtown, NYWelcome to this bright and spacious 2 story Condo in the gated community of Hidden Ponds. ... |
1 beds | 2 baths | 1,044 sq.ft. |
$475,000 |
Airbnb cash on cash: -1.53%
|
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%
|
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. |
$1,150,990 |
Airbnb cash on cash: 1.8%
|
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 | 3,634 sq.ft. |
$1,500,000 |
Airbnb cash on cash: 1.19%
|
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. |
$670,000 |
Airbnb cash on cash: 4.41%
|
16 Wildwood LaneSmithtown, NYHouse For Sale. |
5 beds | 3 baths | 2,204 sq.ft. |
$850,000 |
Airbnb cash on cash: N/A
|
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. |
$699,000 |
Airbnb cash on cash: 2.27%
|
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 |
$950,000 |
Airbnb cash on cash: 1.83%
|
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%
|
271 N Country RoadSmithtown, NYIntroducing one of the most elegant, exquisite, and high-end new construction homes to eve... |
4 beds | 3 baths | N/A |
$999,999 |
Airbnb cash on cash: 3.21%
|
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
|
109 Oakside DriveSmithtown, NYWelcome to 109 Oakside Dr., your dream equestrian retreat, set on 2 scenic acres in the he... |
4 beds | 4 baths | 2,400 sq.ft. |
$1,499,990 |
Airbnb cash on cash: 0.42%
|
239 Pond View LaneSmithtown, NYSmithtown Townhome now showing! Spacious Dartmouth model in preferred Hidden Ponds Condom... |
3 beds | 3 baths | 1,800 sq.ft. |
$679,990 |
Airbnb cash on cash: 1.99%
|
7 Village WaySmithtown, NYBeautiful Home fully renovated in the last few years. Large spacious rooms with beautiful ... |
3 beds | 3 baths | 2,400 sq.ft. |
$749,990 |
Airbnb cash on cash: 1.32%
|
38 McArthur LaneSmithtown, NYWelcome to 38 Mcarthur Lane, a delightful haven nestled in the heart of Smithtown, NY's Gr... |
5 beds | 3 baths | 2,200 sq.ft. |
$849,000 |
Airbnb cash on cash: N/A
|
16 Crawford StreetSmithtown, NYWelcome to 16 Crawford Street, Smithtown! Nestled in the heart of desirable Smithtown, th... |
4 beds | 3 baths | 2,890 sq.ft. |
$874,000 |
Airbnb cash on cash: 2.9%
|
11 Dillmont DriveSmithtown, NYMajestic, Expanded Center Hall Colonial, 4 BR, 2.5 Baths on Usable 1/2 Acre Plus Property ... |
4 beds | 3 baths | 2,900 sq.ft. |
$1,050,000 |
Airbnb cash on cash: 1.96%
|
592 Landing AvenueSmithtown, NYCompletely Renovated Historic 3 story Colonial on private 1.3 Acre parcel with circular dr... |
5 beds | 3 baths | 4,000 sq.ft. |
$1,250,000 |
Airbnb cash on cash: N/A
|
32 Merrivale DriveSmithtown, NYHere's your chance to live in the desirable Sunnydale section of Smithtown!! This spacious... |
5 beds | 3 baths | 2,670 sq.ft. |
$975,000 |
Airbnb cash on cash: N/A
|
18 Thrush DriveSmithtown, NYThis Gorgeous Ranch is a rare gem nestled in the Forestwood section of Smithtown. This dis... |
4 beds | 2 baths | 2,000 sq.ft. |
$899,990 |
Airbnb cash on cash: 2.79%
|
90 Blydenburg AvenueSmithtown, NYLegal Two-Family Home in Prime Smithtown Location! This well-maintained, legal two-family... |
5 beds | 3 baths | 2,200 sq.ft. |
$849,900 |
Airbnb cash on cash: 3.02%
|
74 Laurel DriveSmithtown, NYWelcome to THE PINES, experience exceptional resort-style living in this custom Smithtown ... |
5 beds | 6 baths | 3,800 sq.ft. |
$1,500,000 |
Airbnb cash on cash: N/A
|
365 Route 111 #C-4Smithtown, NYWelcome to this beautifully updated co-op featuring an open floor plan that seamlessly com... |
1 beds | 1 baths | 1,000 sq.ft. |
$245,000 |
Airbnb cash on cash: -3.51%
|
Real Estate investment in Smithtown, NY
There are 74 properties for sale in the city of Smithtown . The median list price in Smithtown is $857,500 and the average price per square foot is $360. In October 2025, the average monthly cash on cash return in Smithtown is 3.00%. The average monthly rental income in Smithtown is $4,497.