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 |
|---|---|---|---|
27 Enchanted Forest RoadSmithtown, NYWelcome to your dream home! This beautifully updated colonial exudes warmth and charm, off... |
5 beds | 4 baths | 2,850 sq.ft. |
$1,295,000 |
Airbnb cash on cash: N/A
|
9 Mulberry DriveSmithtown, NYBeautiful 4-Bedroom, 2-Bath Home with Exceptional Amenities. Owner is motivated to sell, a... |
4 beds | 2 baths | 1,834 sq.ft. |
$895,000 |
Airbnb cash on cash: 3.1%
|
1 Crystal CourtSmithtown, NYAn incredible opportunity to own a magnificent newer-built Colonial tucked away on a quiet... |
4 beds | 4 baths | 2,757 sq.ft. |
$1,095,000 |
Airbnb cash on cash: 1.72%
|
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%
|
175 Evergreen AvenueSmithtown, NYBeautifully renovated split-level home set on manicured, park-like grounds-truly move-in r... |
3 beds | 2 baths | 1,617 sq.ft. |
$779,000 |
Airbnb cash on cash: -0.99%
|
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
|
16 Wildwood LaneSmithtown, NYCharming 5-Bedroom Smithtown Home with In-Ground Pool Welcome to 16 Wildwood Lane, a spaci... |
5 beds | 3 baths | 2,204 sq.ft. |
$850,000 |
Airbnb cash on cash: N/A
|
6 Keystone CourtSmithtown, NYLast Home To Be Built In This Cul-de-sac. Rendering/Photo Shown Conveys Craftsmanship of H... |
4 beds | 4 baths | 2,600 sq.ft. |
$1,550,000 |
Airbnb cash on cash: 2.2%
|
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. |
$1,450,000 |
Airbnb cash on cash: 0.46%
|
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. |
$1,195,000 |
Airbnb cash on cash: N/A
|
4 E Hill DriveSmithtown, NYThis expanded cape home featuring a unique floorplan with two separate living spaces, offe... |
4 beds | 5 baths | 2,225 sq.ft. |
$829,900 |
Airbnb cash on cash: 2.62%
|
769 Meadow RoadSmithtown, NYGreat Opportunity with OVER 2 Acres in Prime Smithtown Location. Possible Sub Division, Ho... |
4 beds | 2 baths | 2,300 sq.ft. |
$999,999 |
Airbnb cash on cash: 2.66%
|
7 Riverview TerraceSmithtown, NYWelcome to 7 Riverview Terrace, an exceptional waterfront residence. Every inch of this ho... |
4 beds | 5 baths | 7,000 sq.ft. |
$2,988,888 |
Airbnb cash on cash: 0.01%
|
291 Terry RoadSmithtown, NYWelcome home to this beautiful 3 bed 1.5 bath expanded cape home. First floor has charming... |
3 beds | 2 baths | 1,426 sq.ft. |
$645,626 |
Airbnb cash on cash: -1.13%
|
17 Thide CourtSmithtown, NYWelcome Home To 17 Thide Court In Smithtown. This Luxurious 3495 Sqft Colonial Is Set On A... |
5 beds | 3 baths | 3,495 sq.ft. |
$1,300,000 |
Airbnb cash on cash: N/A
|
16 Pantzer StreetSmithtown, NYWelcome to 16 Pantzer Street, a beautifully maintained 4-bedroom, 2.5-bath Laurel Colonial... |
4 beds | 3 baths | 2,369 sq.ft. |
$799,000 |
Airbnb cash on cash: 3.45%
|
30 Glacier DriveSmithtown, NYOpportunity Knocks ! Great Bones on this Colonial/Splanch with 4 Bedrooms, 1.55 Baths, 2 C... |
4 beds | 3 baths | 2,138 sq.ft. |
$729,000 |
Airbnb cash on cash: 3.92%
|
355 Route 111 unit: 6 #6Smithtown, NYLovely second floor one bedroom co-op located in Smithtown. Located centrally near shoppin... |
1 beds | 1 baths | 750 sq.ft. |
$249,000 |
Airbnb cash on cash: 2.27%
|
4 Chelsea DriveSmithtown, NYWelcome to 4 Chelsea Drive, Smithtown! Set within the desirable Windcrest Community sits t... |
2 beds | 3 baths | 1,358 sq.ft. |
$635,000 |
Airbnb cash on cash: -1.16%
|
12 Summerset DriveSmithtown, NYCome see this expanded ranch located in the highly sought-after Smithtown School District.... |
4 beds | 2 baths | 1,600 sq.ft. |
$714,900 |
Airbnb cash on cash: 4.25%
|
365 Route 111 unit: A2 #A2Smithtown, NYWelcome to This Beautiful Ground Floor One Bedroom Unit in the Tanglewood Development. Thi... |
1 beds | 1 baths | N/A |
$267,500 |
Airbnb cash on cash: 1.93%
|
6 Stone Gate Court unit: 6 #6Smithtown, NYBeautiful End-Unit Townhouse with Private Entrance & Finished Basement Stunning end-unit t... |
3 beds | 3 baths | 2,481 sq.ft. |
$769,000 |
Airbnb cash on cash: -1.36%
|
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: -0.88%
|
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: -1.25%
|
32 Scarborough DriveSmithtown, NYWelcome to Windcrest at Smithtown, a desirable pet friendly gated community offering maint... |
2 beds | 3 baths | 1,358 sq.ft. |
$599,000 |
Airbnb cash on cash: -1.98%
|
220 Larch LaneSmithtown, NYGreat opportunity to own in Smithtown! Charming 2 Bedroom Ranch set back on private half a... |
2 beds | 1 baths | 1,060 sq.ft. |
$510,000 |
Airbnb cash on cash: 0.05%
|
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%
|
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: -1.57%
|
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%
|
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: -1.35%
|
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: -1.8%
|
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%
|
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: -2.16%
|
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: -1.95%
|
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
|
Real Estate investment in Smithtown, NY
There are 83 properties for sale in the city of Smithtown . The median list price in Smithtown is $779,000 and the average price per square foot is $362. In January 2026, the average monthly cash on cash return in Smithtown is 3.00%. The average monthly rental income in Smithtown is $4,270.