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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
9 Dillmont Dr Smithtown, NY Sprawling Ranch Situated On A Beautiful Half-Acre Property In The Heart Of Smithtown. This...	4 beds \| 3 baths \| 1,870 sq.ft.	$799,803	Airbnb cash on cash: 2.93% Traditional cash on cash: 2.94% Airbnb Rental Income: $5968 Traditional Rental Income: $4787 Airbnb ROI: 2.93% Traditional ROI: 2.94%
2 Vistas Cir Smithtown, NY Serene Location! To Be Built. Please Note That Rendering/Photo Shown Conveys Craftsmanship...	4 beds \| 3 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%
44 Elizabeth Ave Smithtown, NY Welcome to this beautiful, totally renovated expanded Cape offering the perfect blend of s...	3 beds \| 2 baths \| 1,578 sq.ft.	$649,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 4.36% Airbnb Rental Income: $4264 Traditional Rental Income: $4336 Airbnb ROI: 2.76% Traditional ROI: 4.36%
14 Sandpiper Ct Smithtown, NY Nestled on a quiet cul-de-sac, this timeless Colonial offers the perfect blend of comfort,...	4 beds \| 2 baths \| 2,590 sq.ft.	$999,999	Airbnb cash on cash: 1.87% Traditional cash on cash: 2.03% Airbnb Rental Income: $5968 Traditional Rental Income: $4938 Airbnb ROI: 1.87% Traditional ROI: 2.03%
6 Keystone Ct Smithtown, NY Last Home To Be Built In This Cul-de-sac. Rendering/Photo Shown Conveys Craftsmanship of H...	4 beds \| 3 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%
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%
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 Rd Smithtown, NY Welcome to this stately and impressive Colonial, ideally situated in one of Smithtown's mo...	5 beds \| 2 baths \| 2,788 sq.ft.	$1,250,000	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 Ave Smithtown, NY Lovely Colonial Split, 3/4 Bedroom (4th Bedroom or Office), Spacious Throughout, Updated E...	4 beds \| 2 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 Dr 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 Ct 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.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $4658 Airbnb ROI: N/A Traditional ROI: 3.29%
23 Colonial Dr Smithtown, NY Welcome to this stunning custom residence in the highly sought-after Smithtown Pines commu...	5 beds \| 4 baths \| 3,800 sq.ft.	$1,099,988	Airbnb cash on cash: N/A Traditional cash on cash: 3.76% Airbnb Rental Income: $null Traditional Rental Income: $6402 Airbnb ROI: N/A Traditional ROI: 3.76%
106 Summit Dr 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.	$749,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.76% Airbnb Rental Income: $null Traditional Rental Income: $4150 Airbnb ROI: N/A Traditional ROI: 2.76%
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%
20 Oak Tree Dr 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.	$1,050,000	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%
589 Landing Ave Smithtown, NY Nestled at the end of a private long drive shared with only 2 other homes and Not directly...	5 beds \| 2 baths \| 3,851 sq.ft.	$1,626,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.89% Airbnb Rental Income: $null Traditional Rental Income: $5226 Airbnb ROI: N/A Traditional ROI: 0.89%
225 Old Willets Path Smithtown, NY Welcome to this one-of-a-kind custom estate-quality residence rebuilt in 2018 by a profess...	4 beds \| 2 baths \| 3,211 sq.ft.	$1,890,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 0.75% Airbnb Rental Income: $5968 Traditional Rental Income: $5069 Airbnb ROI: 0.59% Traditional ROI: 0.75%
19 Knoll Ln Smithtown, NY Welcome to 19 Knoll Lane, Smithtown - Where Comfort Meets Elegance Nestled in the heart of...	4 beds \| 2 baths \| 2,471 sq.ft.	$950,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 2.25% Airbnb Rental Income: $5968 Traditional Rental Income: $4352 Airbnb ROI: 2.74% Traditional ROI: 2.25%
12 Wayside Lane Smithtown, NY Welcome to 12 Wayside Lane. Beautifully maintained 3-bedroom high ranch. Completely remode...	3 beds \| 2 baths \| 1,134 sq.ft.	$708,000	Airbnb cash on cash: 2.19% Traditional cash on cash: 2.4% Airbnb Rental Income: $4264 Traditional Rental Income: $3501 Airbnb ROI: 2.19% Traditional ROI: 2.4%
29 Ivy Hill Dr Smithtown, NY 29 Ivy Hill Dr, Hauppauge, NY 11787 \| Single Family Residential	4 beds \| 2 baths \| 2,462 sq.ft.	$860,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.1% Airbnb Rental Income: $5968 Traditional Rental Income: $4750 Airbnb ROI: 3.15% Traditional ROI: 3.1%
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%
106 Morewood Drive Smithtown, NY Beautifully renovated with no expense spared, this stunning four-bedroom, three-bath home ...	4 beds \| 3 baths \| 2,100 sq.ft.	$999,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 2.26% Airbnb Rental Income: $5968 Traditional Rental Income: $4987 Airbnb ROI: 2.04% Traditional ROI: 2.26%
7 Monitor Road Smithtown, NY Welcome to Willow Wood Townhouses - Where Luxury Meets Effortless Living. Perfectly positi...	3 beds \| 3 baths \| 1,970 sq.ft.	$775,000	Airbnb cash on cash: 1.81% Traditional cash on cash: 3.07% Airbnb Rental Income: $4264 Traditional Rental Income: $4275 Airbnb ROI: 1.81% Traditional ROI: 3.07%
185 Plymouth Boulevard Smithtown, NY Prestine 4-Bedroom Colonial with FULL BASEMENT in the Smithtown School District! Welcome t...	4 beds \| 3 baths \| 2,448 sq.ft.	$999,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 2.2% Airbnb Rental Income: $5968 Traditional Rental Income: $4783 Airbnb ROI: 2.2% Traditional ROI: 2.2%
8 Mulberry Drive Smithtown, NY Welcome 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% Traditional cash on cash: 2.26% Airbnb Rental Income: $5968 Traditional Rental Income: $3705 Airbnb ROI: 3.71% Traditional ROI: 2.26%
56 Waverly Avenue Smithtown, NY This 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% Traditional cash on cash: 2.72% Airbnb Rental Income: $4264 Traditional Rental Income: $3655 Airbnb ROI: 2.29% Traditional ROI: 2.72%
28 Dartmouth Dr Smithtown, NY Disclaimer: Agent Owned Property Note: Some listing photos have been virtually staged 28 D...	3 beds \| 1 baths \| 1,628 sq.ft.	$762,990	Airbnb cash on cash: 2.07% Traditional cash on cash: 2.82% Airbnb Rental Income: $4264 Traditional Rental Income: $3905 Airbnb ROI: 2.07% Traditional ROI: 2.82%
11 Coventry Lane Smithtown, NY Welcome to this stunning Hamptons-style Colonial located within the highly sought-after Sm...	4 beds \| 3 baths \| 2,500 sq.ft.	$929,000	Airbnb cash on cash: 2.57% Traditional cash on cash: 1.92% Airbnb Rental Income: $5968 Traditional Rental Income: $4227 Airbnb ROI: 2.57% Traditional ROI: 1.92%
18 Ursular Court Smithtown, NY Welcome to this beautifully maintained home in the desirable North Smithtown neighborhood,...	3 beds \| 2 baths \| 1,730 sq.ft.	$839,000	Airbnb cash on cash: 1.38% Traditional cash on cash: 1.82% Airbnb Rental Income: $4264 Traditional Rental Income: $3706 Airbnb ROI: 1.38% Traditional ROI: 1.82%
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.	$599,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 4.12% Airbnb Rental Income: $4264 Traditional Rental Income: $3840 Airbnb ROI: 3.27% Traditional ROI: 4.12%
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%
9 Chester Street Smithtown, NY Opportunity knocks in the heart of Smithtown! This well-maintained 4-bedroom, 2.5-bath col...	4 beds \| 3 baths \| 2,041 sq.ft.	$749,999	Airbnb cash on cash: 4.01% Traditional cash on cash: 3.11% Airbnb Rental Income: $5968 Traditional Rental Income: $4154 Airbnb ROI: 4.01% Traditional ROI: 3.11%
58 Cherry Lane Smithtown, NY Welcome to 58 Cherry Lane ~ A beautiful house in a beautiful neighborhood waiting to be yo...	4 beds \| 2 baths \| 2,100 sq.ft.	$875,000	Airbnb cash on cash: 3.15% Traditional cash on cash: 2.33% Airbnb Rental Income: $5968 Traditional Rental Income: $4114 Airbnb ROI: 3.15% Traditional ROI: 2.33%
39 Tanglewood Drive Smithtown, NY Welcome to this beautifully renovated 3-bedroom, 1.5-bath ranch nestled in Smithtown and l...	3 beds \| 2 baths \| 1,313 sq.ft.	$679,000	Airbnb cash on cash: 2.44% Traditional cash on cash: 2.97% Airbnb Rental Income: $4264 Traditional Rental Income: $3702 Airbnb ROI: 2.44% Traditional ROI: 2.97%
12 Sandalwood Drive Smithtown, NY Welcome to this beautifully renovated ranch that offers the perfect blend of comfort, styl...	3 beds \| 2 baths \| 1,332 sq.ft.	$749,999	Airbnb cash on cash: -0.1% Traditional cash on cash: 2.54% Airbnb Rental Income: $2362 Traditional Rental Income: $3625 Airbnb ROI: -0.1% Traditional ROI: 2.54%
1 Valley Avenue Smithtown, NY Completely 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% Traditional cash on cash: 1.16% Airbnb Rental Income: $4264 Traditional Rental Income: $4671 Airbnb ROI: -0.07% Traditional ROI: 1.16%
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%

Your search for investment property begins and ends here

Single Family Homes for Sale in Smithtown, NY

9 Dillmont Dr

Smithtown, NY

4 beds | 3 baths | 1,870 sq.ft.

$799,803

Airbnb cash on cash: 2.93%

Traditional cash on cash: 2.94%

Airbnb Rental Income: $5968

Traditional Rental Income: $4787

Airbnb ROI: 2.93%

Traditional ROI: 2.94%

2 Vistas Cir

Smithtown, NY

4 beds | 3 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%

44 Elizabeth Ave

Smithtown, NY

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

$649,000

Airbnb cash on cash: 2.76%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $4264

Traditional Rental Income: $4336

Airbnb ROI: 2.76%

Traditional ROI: 4.36%

14 Sandpiper Ct

Smithtown, NY

4 beds | 2 baths | 2,590 sq.ft.

$999,999

Airbnb cash on cash: 1.87%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $5968

Traditional Rental Income: $4938

Airbnb ROI: 1.87%

Traditional ROI: 2.03%

6 Keystone Ct

Smithtown, NY

4 beds | 3 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%

57 Juniper Avenue

Smithtown, NY

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%

17 Erita Lane

Smithtown, NY

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

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%