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.

Single Family Homes for Sale in Smithtown, NY

Search for Single Family Residential for Sale in Smithtown, New York. Browse all of Mashvisor’s Single Family Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 80 Single Family Residential listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
2 Cindy Street Smithtown, NY BACK 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% Traditional cash on cash: 2.26% Airbnb Rental Income: $5968 Traditional Rental Income: $4131 Airbnb ROI: 3.09% Traditional ROI: 2.26%
28 Dartmouth Drive Smithtown, NY Disclaimer: Agent Owned Property Warm and inviting ranch in the heart of Smithtown within ...	4 beds \| 2 baths \| 1,625 sq.ft.	$787,000	Airbnb cash on cash: 3.94% Traditional cash on cash: 2.74% Airbnb Rental Income: $5968 Traditional Rental Income: $3905 Airbnb ROI: 3.94% Traditional ROI: 2.74%
2 Vistas Circle Smithtown, NY Serene 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% Traditional cash on cash: 0.36% Airbnb Rental Income: $5968 Traditional Rental Income: $4378 Airbnb ROI: 0.66% Traditional ROI: 0.36%
23 Whitney Gate Smithtown, 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% Traditional cash on cash: 2.62% Airbnb Rental Income: $5968 Traditional Rental Income: $4744 Airbnb ROI: 2.68% Traditional ROI: 2.62%
15 7th Avenue Smithtown, NY Bright 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% Traditional cash on cash: 3.12% Airbnb Rental Income: $4264 Traditional Rental Income: $4549 Airbnb ROI: 1.53% Traditional ROI: 3.12%
5 Hawkins Avenue Smithtown, NY Charming and beautifully restored, this home seamlessly blends the character of its 1918 o...	3 beds \| 2 baths \| 2,000 sq.ft.	$650,000	Airbnb cash on cash: 2.94% Traditional cash on cash: 3.65% Airbnb Rental Income: $4264 Traditional Rental Income: $3800 Airbnb ROI: 2.94% Traditional ROI: 3.65%
79 Brooksite Drive Smithtown, NY Welcome 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% Traditional cash on cash: 3.29% Airbnb Rental Income: $4264 Traditional Rental Income: $3705 Airbnb ROI: 2.77% Traditional ROI: 3.29%
44 Elizabeth Avenue Smithtown, NY Beautiful newly renovated expanded Cape featuring 4 bedrooms and 2 full baths. This spacio...	4 beds \| 2 baths \| 1,578 sq.ft.	$649,999	Airbnb cash on cash: 5.09% Traditional cash on cash: 4.35% Airbnb Rental Income: $5968 Traditional Rental Income: $4336 Airbnb ROI: 5.09% Traditional ROI: 4.35%
6 Keystone Court Smithtown, NY Last 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% Traditional cash on cash: 2.59% Airbnb Rental Income: $5968 Traditional Rental Income: $5351 Airbnb ROI: 2.2% Traditional ROI: 2.59%
3 Baylor Drive Smithtown, NY Move right into this diamond 3BR, 2 BA ranch located in the highly desired college section...	3 beds \| 2 baths \| 1,300 sq.ft.	$799,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 1.98% Airbnb Rental Income: $4264 Traditional Rental Income: $3500 Airbnb ROI: 1.8% Traditional ROI: 1.98%
57 Juniper Avenue Smithtown, NY This 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% Traditional cash on cash: 2.04% Airbnb Rental Income: $4264 Traditional Rental Income: $3048 Airbnb ROI: 2.5% Traditional ROI: 2.04%
48 River Heights Drive Smithtown, NY Welcome to 48 River Heights Drive where a tree lined street meets a true custom masterpiec...	5 beds \| 4 baths \| 4,800 sq.ft.	$1,499,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.05% Airbnb Rental Income: $null Traditional Rental Income: $6386 Airbnb ROI: N/A Traditional ROI: 2.05%
17 Erita Lane Smithtown, NY Welcome 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% Traditional cash on cash: 1.68% Airbnb Rental Income: $5968 Traditional Rental Income: $4769 Airbnb ROI: 1.7% Traditional ROI: 1.68%
57 Birchbrook Dr Smithtown, NY LISTING 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% Traditional cash on cash: 2.76% Airbnb Rental Income: $4264 Traditional Rental Income: $3614 Airbnb ROI: 2.4% Traditional ROI: 2.76%
2 Three Pond Road Smithtown, NY Welcome to this stately and impressive Colonial, ideally situated in one of Smithtown's mo...	5 beds \| 4 baths \| 2,788 sq.ft.	$1,399,999	Airbnb cash on cash: N/A Traditional cash on cash: 1.83% Airbnb Rental Income: $null Traditional Rental Income: $5671 Airbnb ROI: N/A Traditional ROI: 1.83%
43 Hallock Avenue Smithtown, NY Lovely Colonial Split, 3/4 Bedroom (4th Bedroom or Office), Spacious Throughout, Updated E...	4 beds \| 3 baths \| 2,029 sq.ft.	$849,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 2.98% Airbnb Rental Income: $5968 Traditional Rental Income: $4677 Airbnb ROI: 3.12% Traditional ROI: 2.98%
4 Clearbrook Drive Smithtown, NY Home 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% Traditional cash on cash: 2.33% Airbnb Rental Income: $4264 Traditional Rental Income: $3189 Airbnb ROI: 2.62% Traditional ROI: 2.33%
20 Veronica Court Smithtown, NY Welcome to 20 Veronica Court, Smithtown - a spacious ranch-style home nestled on a quiet c...	5 beds \| 3 baths \| 2,196 sq.ft.	$749,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.15% Airbnb Rental Income: $null Traditional Rental Income: $4658 Airbnb ROI: N/A Traditional ROI: 3.15%
288 Bow Drive Smithtown, NY Turn Key Home in Beautiful Neighborhood with Lots of Trees, Sidewalks, Parks Nearby, Smith...	4 beds \| 3 baths \| 2,531 sq.ft.	$999,000	Airbnb cash on cash: 2.43% Traditional cash on cash: 2.77% Airbnb Rental Income: $5968 Traditional Rental Income: $5102 Airbnb ROI: 2.43% Traditional ROI: 2.77%
214 Landing Avenue Smithtown, NY PRICE RESET AND TAX GRIEVANCE FILED(Letter in photos) If you've been looking for a spa...	3 beds \| 3 baths \| 2,112 sq.ft.	$649,000	Airbnb cash on cash: 1.11% Traditional cash on cash: 2.7% Airbnb Rental Income: $4264 Traditional Rental Income: $4329 Airbnb ROI: 1.11% Traditional ROI: 2.7%
5 Supreme Court Smithtown, NY Welcome to 5 Supreme Court, Smithtown - Located in the Highly Sought-After Hauppauge Schoo...	4 beds \| 4 baths \| 3,646 sq.ft.	$999,999	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.83% Airbnb Rental Income: $5968 Traditional Rental Income: $6159 Airbnb ROI: 2.36% Traditional ROI: 3.83%
23 Colonial Drive Smithtown, NY Welcome to this stunning custom residence in the highly sought-after Smithtown Pines commu...	5 beds \| 4 baths \| 3,800 sq.ft.	$1,199,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.64% Airbnb Rental Income: $null Traditional Rental Income: $6402 Airbnb ROI: N/A Traditional ROI: 3.64%
106 Summit Drive Smithtown, NY Great Hi Ranch with 2 Sep Living Areas plus Garage, Fenced Yard, Oversize Driveway, Smitht...	5 beds \| 2 baths \| 2,100 sq.ft.	$799,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.39% Airbnb Rental Income: $null Traditional Rental Income: $4795 Airbnb ROI: N/A Traditional ROI: 3.39%
2 Crystal Court Smithtown, NY Welcome to 2 Crystal Court nestled on a private cul-de-sac in the heart of Smithtown! Step...	4 beds \| 3 baths \| 2,700 sq.ft.	$1,099,000	Airbnb cash on cash: 1.84% Traditional cash on cash: 1.67% Airbnb Rental Income: $5968 Traditional Rental Income: $4610 Airbnb ROI: 1.84% Traditional ROI: 1.67%
34 Paddington Circle Smithtown, NY Welcome to 34 Paddington Circle! This desirable end-unit townhouse is located in the heart...	3 beds \| 3 baths \| 1,484 sq.ft.	$695,000	Airbnb cash on cash: 2.15% Traditional cash on cash: 2.87% Airbnb Rental Income: $4264 Traditional Rental Income: $3829 Airbnb ROI: 2.15% Traditional ROI: 2.87%
115 Morewood Drive Smithtown, NY Welcome to this beautifully maintained home featuring an open-concept layout with hardwood...	4 beds \| 2 baths \| 1,940 sq.ft.	$799,992	Airbnb cash on cash: 3.63% Traditional cash on cash: 2.53% Airbnb Rental Income: $5968 Traditional Rental Income: $3965 Airbnb ROI: 3.63% Traditional ROI: 2.53%
39 Burham Drive Smithtown, NY Welcome 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 Traditional cash on cash: 3.31% Airbnb Rental Income: $null Traditional Rental Income: $5571 Airbnb ROI: N/A Traditional ROI: 3.31%
4 Concord Lane Smithtown, NY Welcome to this beautifully maintained Hi-Ranch in the heart of Smithtown featuring a spac...	4 beds \| 2 baths \| 1,264 sq.ft.	$849,000	Airbnb cash on cash: 3.26% Traditional cash on cash: 2.12% Airbnb Rental Income: $5968 Traditional Rental Income: $3890 Airbnb ROI: 3.26% Traditional ROI: 2.12%
322 Rose Lane Smithtown, NY Looking for that "wow" factor? Welcome to this beautiful, totally custom 4bed/3.5bath home...	4 beds \| 4 baths \| 4,248 sq.ft.	$1,329,000	Airbnb cash on cash: 1.47% Traditional cash on cash: 2.88% Airbnb Rental Income: $5968 Traditional Rental Income: $6527 Airbnb ROI: 1.47% Traditional ROI: 2.88%
3 Bradley Court Smithtown, NY Welcome to 3 Bradley Court, a charming 4-bedroom, 2-bathroom Hi-Ranch residence nestled pe...	4 beds \| 2 baths \| 1,844 sq.ft.	$749,990	Airbnb cash on cash: 4.06% Traditional cash on cash: 2.78% Airbnb Rental Income: $5968 Traditional Rental Income: $3886 Airbnb ROI: 4.06% Traditional ROI: 2.78%
12 Westbrook Lane Smithtown, NY GOING....GOING.... GONE......!!Don't blink or you will miss this one. Completely renovated...	4 beds \| 3 baths \| 1,788 sq.ft.	$849,990	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.43% Airbnb Rental Income: $5968 Traditional Rental Income: $4538 Airbnb ROI: 3.74% Traditional ROI: 3.43%
37 Winston Drive Smithtown, NY Two Adjacent Lots in Sought-After Smithtown Pines on Over 2 Scenic Acres! Each lot is over...	3 beds \| 1 baths \| N/A	$1,200,000	Airbnb cash on cash: 1.15% Traditional cash on cash: 1.09% Airbnb Rental Income: $4264 Traditional Rental Income: $3292 Airbnb ROI: 1.15% Traditional ROI: 1.09%
27 Lindner Place Smithtown, NY Welcome to 27 Lindner Place, Smithtown! This completely move-in ready and fully updated 3-...	3 beds \| 1 baths \| 1,229 sq.ft.	$599,999	Airbnb cash on cash: 3.66% Traditional cash on cash: 2.83% Airbnb Rental Income: $4264 Traditional Rental Income: $2899 Airbnb ROI: 3.66% Traditional ROI: 2.83%
74A Hilltop Drive #A Smithtown, NY Welcome to 74A Hilltop, a beautifully maintained home offering the perfect blend of space,...	5 beds \| 2 baths \| 2,044 sq.ft.	$849,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.63% Airbnb Rental Income: $null Traditional Rental Income: $4333 Airbnb ROI: N/A Traditional ROI: 2.63%
20 Oak Tree Drive Smithtown, NY Beautiful spacious ranch in the desirable Village of the branch. Four beds, 3 full baths. ...	4 beds \| 3 baths \| 2,400 sq.ft.	$1,075,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 2.03% Airbnb Rental Income: $5968 Traditional Rental Income: $4668 Airbnb ROI: 2.14% Traditional ROI: 2.03%
73 Redan Drive Smithtown, NY Welcome to this beautifully Updated Custom-built Colonial w/ 3,500 sq ft of elegant living...	4 beds \| 4 baths \| 3,500 sq.ft.	$1,269,000	Airbnb cash on cash: 1.55% Traditional cash on cash: 2.74% Airbnb Rental Income: $5968 Traditional Rental Income: $6188 Airbnb ROI: 1.55% Traditional ROI: 2.74%
17 Leslie Lane Smithtown, NY Welcome to 17 Leslie Lane...a Beautifully updated Colonial Splanch nestled in a tree-lined...	4 beds \| 3 baths \| 2,613 sq.ft.	$899,000	Airbnb cash on cash: 2.78% Traditional cash on cash: 3.11% Airbnb Rental Income: $5968 Traditional Rental Income: $5060 Airbnb ROI: 2.78% Traditional ROI: 3.11%
75 Summit Drive Smithtown, NY Welcome to this beautifully maintained expanded ranch nestled on a manicured 1/3 acre in S...	3 beds \| 3 baths \| 1,485 sq.ft.	$679,000	Airbnb cash on cash: 2.36% Traditional cash on cash: 3.3% Airbnb Rental Income: $4264 Traditional Rental Income: $3960 Airbnb ROI: 2.36% Traditional ROI: 3.3%
61 Hofstra Drive Smithtown, NY Welcome to this beautifully expanded Colonial nestled in the highly sought after College S...	4 beds \| 3 baths \| 1,900 sq.ft.	$789,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 3.6% Airbnb Rental Income: $5968 Traditional Rental Income: $4526 Airbnb ROI: 3.95% Traditional ROI: 3.6%
45 Lone Oak Path Smithtown, NY Large Center Hall Colonial in Hauppague SD! Three Bedrooms, One and one-half baths, Make t...	3 beds \| 2 baths \| 3,572 sq.ft.	$779,990	Airbnb cash on cash: 3.08% Traditional cash on cash: 3.57% Airbnb Rental Income: $4264 Traditional Rental Income: $3720 Airbnb ROI: 3.08% Traditional ROI: 3.57%

Your search for investment property begins and ends here

Single Family Homes for Sale in Smithtown, NY

2 Cindy Street

Smithtown, NY

4 beds | 2 baths | 1,900 sq.ft.

$849,999

Airbnb cash on cash: 3.09%

Traditional cash on cash: 2.26%

Airbnb Rental Income: $5968

Traditional Rental Income: $4131

Airbnb ROI: 3.09%

Traditional ROI: 2.26%

28 Dartmouth Drive

Smithtown, NY

4 beds | 2 baths | 1,625 sq.ft.

$787,000

Airbnb cash on cash: 3.94%

Traditional cash on cash: 2.74%

Airbnb Rental Income: $5968

Traditional Rental Income: $3905

Airbnb ROI: 3.94%

Traditional ROI: 2.74%

2 Vistas Circle

Smithtown, NY

4 beds | 4 baths | 2,600 sq.ft.

$1,499,000

Airbnb cash on cash: 0.66%

Traditional cash on cash: 0.36%

Airbnb Rental Income: $5968

Traditional Rental Income: $4378

Airbnb ROI: 0.66%

Traditional ROI: 0.36%

23 Whitney Gate

Smithtown, NY

4 beds | 3 baths | 2,500 sq.ft.

$800,000

Airbnb cash on cash: 2.68%

Traditional cash on cash: 2.62%

Airbnb Rental Income: $5968

Traditional Rental Income: $4744

Airbnb ROI: 2.68%

Traditional ROI: 2.62%

15 7th Avenue

Smithtown, NY

3 beds | 3 baths | N/A

$799,000

Airbnb cash on cash: 1.53%

Traditional cash on cash: 3.12%

Airbnb Rental Income: $4264

Traditional Rental Income: $4549

Airbnb ROI: 1.53%

Traditional ROI: 3.12%

5 Hawkins Avenue

Smithtown, NY

3 beds | 2 baths | 2,000 sq.ft.

$650,000

Airbnb cash on cash: 2.94%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $4264

Traditional Rental Income: $3800

Airbnb ROI: 2.94%

Traditional ROI: 3.65%

79 Brooksite Drive

Smithtown, NY

3 beds | 2 baths | 1,045 sq.ft.

$699,999

Airbnb cash on cash: 2.77%

Traditional cash on cash: 3.29%

Airbnb Rental Income: $4264

Traditional Rental Income: $3705

Airbnb ROI: 2.77%

Traditional ROI: 3.29%

44 Elizabeth Avenue

Smithtown, NY

4 beds | 2 baths | 1,578 sq.ft.

$649,999

Airbnb cash on cash: 5.09%

Traditional cash on cash: 4.35%

Airbnb Rental Income: $5968

Traditional Rental Income: $4336

Airbnb ROI: 5.09%