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 |
|---|---|---|---|
7 Monitor RoadSmithtown, NYWelcome to Willow Wood Townhouses - Where Luxury Meets Effortless Living. Perfectly positi... |
3 beds | 3 baths | 1,970 sq.ft. |
$798,000 |
Airbnb cash on cash: 1.73%
|
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 DriveSmithtown, NYDisclaimer: Agent Owned Property Warm and inviting ranch in the heart of Smithtown within ... |
4 beds | 2 baths | 1,625 sq.ft. |
$789,000 |
Airbnb cash on cash: 3.93%
|
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%
|
17 Stone Gate CourtSmithtown, NYTucked away on a quiet cul-de-sac in the heart of Smithtown, this hidden gem offers privac... |
3 beds | 4 baths | 1,810 sq.ft. |
$749,000 |
Airbnb cash on cash: 1.66%
|
44 Elizabeth AvenueSmithtown, NYBeautiful newly renovated expanded Cape featuring 4 bedrooms and 2 full baths. This spacio... |
4 beds | 2 baths | 1,578 sq.ft. |
$699,999 |
Airbnb cash on cash: 4.66%
|
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%
|
166 Grassy Pond Drive SSmithtown, NYCustom build in 2002 this beautiful sprawling Ranch offers significantly sized rooms. Open... |
3 beds | 2 baths | 2,059 sq.ft. |
$890,000 |
Airbnb cash on cash: 1.21%
|
17 Erita LaneSmithtown, NYBUYERS LOOK NO FURTHER! ALL NEW! ALL HIGH END! PRIME LOCATION! Pride of ownership and meti... |
4 beds | 3 baths | 2,495 sq.ft. |
$1,199,888 |
Airbnb cash on cash: 1.93%
|
10 Smithtown Boulevard unit: 6ASmithtown, NYWelcome to 10 Smithtown Boulevard, Unit 6A, a beautifully redesigned main-level residence ... |
1 beds | 1 baths | 820 sq.ft. |
$399,999 |
Airbnb cash on cash: -0.9%
|
5 Hancock StreetSmithtown, NYextremely well maintained ranch with walkout basement mostly finished. home has gleaming h... |
3 beds | 2 baths | 1,100 sq.ft. |
$749,990 |
Airbnb cash on cash: 2.28%
|
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%
|
240 Pond View LaneSmithtown, NYBeautifully upgraded and meticulously maintained 2-bedroom, 2.5-bath duplex in the gated c... |
2 beds | 3 baths | 1,495 sq.ft. |
$699,888 |
Airbnb cash on cash: -1.51%
|
157 Hidden Ponds CircleSmithtown, NYWelcome to this beautifully maintained 2-bedroom, 2.5-bath condominium located in a desira... |
2 beds | 3 baths | 1,576 sq.ft. |
$699,999 |
Airbnb cash on cash: -1.44%
|
2 Three Pond RoadSmithtown, NYWelcome to this stately and impressive Colonial, ideally situated in one of Smithtown's mo... |
5 beds | 4 baths | 2,788 sq.ft. |
$1,499,000 |
Airbnb cash on cash: N/A
|
99 Shirley CourtSmithtown, NYNestled in the highly desirable Smithtown Pines, this one-of-a-kind home offers a unique l... |
5 beds | 5 baths | 3,634 sq.ft. |
$1,200,000 |
Airbnb cash on cash: N/A
|
32 Derby PlaceSmithtown, NYCharming ranch-style home featuring 3 bedrooms and 2.5 baths, including a partially finish... |
3 beds | 3 baths | 1,609 sq.ft. |
$775,000 |
Airbnb cash on cash: 1.67%
|
28 Willow Ridge DriveSmithtown, NYWelcome to the highly sought-after Willow Ridge community in North Smithtown, where lifest... |
2 beds | 3 baths | 1,863 sq.ft. |
$699,999 |
Airbnb cash on cash: -1.7%
|
43 Hallock AvenueSmithtown, NYLovely Colonial Split, 3/4 Bedroom (4th Bedroom or Office), Spacious Throughout, Updated E... |
4 beds | 3 baths | 2,029 sq.ft. |
$899,000 |
Airbnb cash on cash: 2.89%
|
69 Amsterdam RoadSmithtown, NYWelcome to 69 Amsterdam Road, a spacious home located in the highly sought-after Royal Oak... |
4 beds | 2 baths | 2,445 sq.ft. |
$799,000 |
Airbnb cash on cash: 3.29%
|
41 Landing Meadow RoadSmithtown, NYWelcome to this exceptional home located in the highly desirable area of North Smithtown, ... |
4 beds | 5 baths | 3,149 sq.ft. |
$1,240,000 |
Airbnb cash on cash: 1.42%
|
16 Ursular CourtSmithtown, NYStep inside this Beautiful & Spacious 4 Bedroom, 3 Full Bath Farm Ranch! This home feature... |
4 beds | 3 baths | 2,074 sq.ft. |
$899,000 |
Airbnb cash on cash: 2.95%
|
30 Redan DriveSmithtown, NYLove Where You Live! Enjoy a Country Club Life Style while Living in a Gated Golf Course C... |
3 beds | 3 baths | 2,400 sq.ft. |
$1,200,000 |
Airbnb cash on cash: 0.47%
|
2 Cindy StreetSmithtown, NYSay Hello To Your New Home! This Colonial Is A True Stunner Featuring Hardwood Floors And ... |
4 beds | 2 baths | 1,900 sq.ft. |
$775,000 |
Airbnb cash on cash: 3.48%
|
1 Park CourtSmithtown, NYLooks can be deceiving...Welcome home to this beautifully updated, sprawling expanded ranc... |
4 beds | 3 baths | 1,900 sq.ft. |
$729,888 |
Airbnb cash on cash: 3.91%
|
12 Darling AvenueSmithtown, NYWelcome to 12 Darling Ave. located in the heart of Smithtown. Situated on a .32, level acr... |
4 beds | 2 baths | N/A |
$849,000 |
Airbnb cash on cash: 3.54%
|
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%
|
69 Churchill LaneSmithtown, NYWelcome to 69 Churchill Lane, a custom-designed expanded ranch nestled in the heart of the... |
4 beds | 4 baths | 2,128 sq.ft. |
$949,000 |
Airbnb cash on cash: 2.82%
|
365 Route 111 unit: 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: -5.11%
|
5 Poplar DriveSmithtown, NYWelcome to this completely renovated and expanded split ranch located in the highly sought... |
4 beds | 3 baths | 3,662 sq.ft. |
$1,288,888 |
Airbnb cash on cash: 2.42%
|
1 Valley AvenueSmithtown, NYCompletely renovated luxury home in beautiful Smithtown. The exceptionally bright and airy... |
3 beds | 3 baths | 2,600 sq.ft. |
$1,150,000 |
Airbnb cash on cash: -0.07%
|
34 MOREWOOD DRIVESmithtown, NYMAGNIFICENT BUILDERS MODEL 4 BEDROOM 2 FULL BATH COLONIAL, LOCATED IN THE MOREWOOD ESTATES... |
4 beds | 2 baths | 2,267 sq.ft. |
$849,999 |
Airbnb cash on cash: 3.27%
|
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%
|
56 Rose StreetSmithtown, NYBeautiful wide line Ranch on half acre in walking distance to Golf course and town pool. 4... |
4 beds | 3 baths | 2,300 sq.ft. |
$639,000 |
Airbnb cash on cash: 4.66%
|
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. |
$1,199,000 |
Airbnb cash on cash: N/A
|
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: 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: 0.17%
|
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: -2.42%
|
16 Blackman StreetSmithtown, NYWelcome to 16 Blackman Street, a charming 1960 cape home that has been lovingly maintained... |
4 beds | 2 baths | 1,323 sq.ft. |
$625,000 |
Airbnb cash on cash: 5.26%
|
Real Estate investment in Smithtown, NY
There are 61 properties for sale in the city of Smithtown . The median list price in Smithtown is $775,000 and the average price per square foot is $381. In April 2026, the average monthly cash on cash return in Smithtown is 3.00%. The average monthly rental income in Smithtown is $4,195.