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 41 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
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.	$798,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 2.96% Airbnb Rental Income: $4264 Traditional Rental Income: $4275 Airbnb ROI: 1.73% Traditional ROI: 2.96%
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 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.	$789,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 2.73% Airbnb Rental Income: $5968 Traditional Rental Income: $3905 Airbnb ROI: 3.93% Traditional ROI: 2.73%
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%
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.	$689,999	Airbnb cash on cash: 4.74% Traditional cash on cash: 4.05% Airbnb Rental Income: $5968 Traditional Rental Income: $4336 Airbnb ROI: 4.74% Traditional ROI: 4.05%
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%
7 Quincy Lane Smithtown, NY Step inside this Beautiful & Spacious 4 Bedroom, 3 Full bath California Hi Ranch! This hom...	4 beds \| 3 baths \| 2,183 sq.ft.	$849,999	Airbnb cash on cash: 3.08% Traditional cash on cash: 3.21% Airbnb Rental Income: $5968 Traditional Rental Income: $4888 Airbnb ROI: 3.08% Traditional ROI: 3.21%
17 Erita Lane Smithtown, NY BUYERS 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% Traditional cash on cash: 1.91% Airbnb Rental Income: $5968 Traditional Rental Income: $4769 Airbnb ROI: 1.93% Traditional ROI: 1.91%
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.	$1,499,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.64% Airbnb Rental Income: $null Traditional Rental Income: $5671 Airbnb ROI: N/A Traditional ROI: 1.64%
99 Shirley Court Smithtown, NY Nestled 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 Traditional cash on cash: 4.5% Airbnb Rental Income: $null Traditional Rental Income: $7640 Airbnb ROI: N/A Traditional ROI: 4.5%
32 Derby Place Smithtown, NY Charming 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% Traditional cash on cash: 2.31% Airbnb Rental Income: $4264 Traditional Rental Income: $3828 Airbnb ROI: 1.67% Traditional ROI: 2.31%
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.	$899,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 2.76% Airbnb Rental Income: $5968 Traditional Rental Income: $4677 Airbnb ROI: 2.89% Traditional ROI: 2.76%
69 Amsterdam Road Smithtown, NY Welcome 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% Traditional cash on cash: 2.72% Airbnb Rental Income: $5968 Traditional Rental Income: $4362 Airbnb ROI: 3.29% Traditional ROI: 2.72%
41 Landing Meadow Road Smithtown, NY Welcome 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% Traditional cash on cash: 3.33% Airbnb Rental Income: $5968 Traditional Rental Income: $6986 Airbnb ROI: 1.42% Traditional ROI: 3.33%
30 Redan Drive Smithtown, NY Love 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% Traditional cash on cash: 1.3% Airbnb Rental Income: $4264 Traditional Rental Income: $4287 Airbnb ROI: 0.47% Traditional ROI: 1.3%
14 Ursular Court Smithtown, NY Welcome to 14 Ursular Court located in the heart of North Smithtown!!! This Charming updat...	3 beds \| 1 baths \| 1,162 sq.ft.	$769,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 2.96% Airbnb Rental Income: $4264 Traditional Rental Income: $3800 Airbnb ROI: 2.35% Traditional ROI: 2.96%
20 Pineacre Drive Smithtown, NY Welcome Home to this spacious and multifunctional Colonial!!Large eat-in kitchen, formal d...	5 beds \| 4 baths \| 2,710 sq.ft.	$999,999	Airbnb cash on cash: N/A Traditional cash on cash: 2.97% Airbnb Rental Income: $null Traditional Rental Income: $5270 Airbnb ROI: N/A Traditional ROI: 2.97%
34 Hunter Place Smithtown, NY Welcome to this beautifully updated 3-bedroom, 2-bath split-level home, perfectly situated...	3 beds \| 2 baths \| 1,085 sq.ft.	$799,999	Airbnb cash on cash: 2.09% Traditional cash on cash: 2.67% Airbnb Rental Income: $4264 Traditional Rental Income: $3800 Airbnb ROI: 2.09% Traditional ROI: 2.67%
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: 2.99% Traditional cash on cash: 3.71% Airbnb Rental Income: $4264 Traditional Rental Income: $3800 Airbnb ROI: 2.99% Traditional ROI: 3.71%
2 Cindy Street Smithtown, NY Say 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% Traditional cash on cash: 2.57% Airbnb Rental Income: $5968 Traditional Rental Income: $4131 Airbnb ROI: 3.48% Traditional ROI: 2.57%
1 Park Court Smithtown, NY Looks 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% Traditional cash on cash: 3.71% Airbnb Rental Income: $5968 Traditional Rental Income: $4646 Airbnb ROI: 3.91% Traditional ROI: 3.71%
12 Darling Avenue Smithtown, NY Welcome 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% Traditional cash on cash: 2.89% Airbnb Rental Income: $5968 Traditional Rental Income: $4272 Airbnb ROI: 3.54% Traditional ROI: 2.89%
69 Churchill Lane Smithtown, NY Welcome 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% Traditional cash on cash: 2.78% Airbnb Rental Income: $5968 Traditional Rental Income: $4750 Airbnb ROI: 2.82% Traditional ROI: 2.78%
5 Poplar Drive Smithtown, NY Welcome 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% Traditional cash on cash: 1.68% Airbnb Rental Income: $5968 Traditional Rental Income: $3889 Airbnb ROI: 2.42% Traditional ROI: 1.68%
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%
4 E Hill Drive Smithtown, NY This 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% Traditional cash on cash: 4.17% Airbnb Rental Income: $5968 Traditional Rental Income: $5983 Airbnb ROI: 2.62% Traditional ROI: 4.17%
30 Glacier Drive Smithtown, NY Opportunity 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% Traditional cash on cash: 3.37% Airbnb Rental Income: $5968 Traditional Rental Income: $4414 Airbnb ROI: 3.92% Traditional ROI: 3.37%
49 Lexington Avenue Smithtown, NY Welcome to 49 Lexington Avenue!!! This beautifully updated Ranch features an entry foyer w...	3 beds \| 3 baths \| 2,195 sq.ft.	$719,000	Airbnb cash on cash: 1.98% Traditional cash on cash: 3.21% Airbnb Rental Income: $4264 Traditional Rental Income: $4191 Airbnb ROI: 1.98% Traditional ROI: 3.21%
27 Dillmont Drive Smithtown, NY Welcome to Smithtowns jewel in the rough. This home needs love but offers so much value fo...	4 beds \| 2 baths \| 1,518 sq.ft.	$599,888	Airbnb cash on cash: 4.97% Traditional cash on cash: 3.08% Airbnb Rental Income: $5968 Traditional Rental Income: $3726 Airbnb ROI: 4.97% Traditional ROI: 3.08%
66 Darling Avenue Smithtown, NY Welcome to 66 Darling Avenue. This charming and spacious Colonial features four generously...	4 beds \| 3 baths \| 2,154 sq.ft.	$775,000	Airbnb cash on cash: 4.05% Traditional cash on cash: 3.5% Airbnb Rental Income: $5968 Traditional Rental Income: $4387 Airbnb ROI: 4.05% Traditional ROI: 3.5%
18 Annetta Avenue Smithtown, NY Wonderful opportunity to own a lovely home located on a quiet street with Smithtown school...	3 beds \| 1 baths \| 1,400 sq.ft.	$599,990	Airbnb cash on cash: 2.92% Traditional cash on cash: 2.55% Airbnb Rental Income: $4264 Traditional Rental Income: $3157 Airbnb ROI: 2.92% Traditional ROI: 2.55%
96 Brooksite Drive Smithtown, NY Opportunity Knocks! Welcome to this beautiful 3-bedroom, 2-bath mint-plus ranch set on a f...	3 beds \| 2 baths \| 1,544 sq.ft.	$799,000	Airbnb cash on cash: 2.14% Traditional cash on cash: 2.49% Airbnb Rental Income: $4264 Traditional Rental Income: $3621 Airbnb ROI: 2.14% Traditional ROI: 2.49%
8 Noel Place Smithtown, NY This expanded Cape offers all the charm of New England, complete with a covered front porc...	4 beds \| 3 baths \| 2,595 sq.ft.	$775,000	Airbnb cash on cash: 3.5% Traditional cash on cash: 3.53% Airbnb Rental Income: $5968 Traditional Rental Income: $4804 Airbnb ROI: 3.5% Traditional ROI: 3.53%
173 Fifty Acre Road S Smithtown, NY Welcome to 173 Fifty Acre Road ...This home features a welcoming entry foyer area, a spaci...	4 beds \| 2 baths \| 2,426 sq.ft.	$699,999	Airbnb cash on cash: 4% Traditional cash on cash: 2.79% Airbnb Rental Income: $5968 Traditional Rental Income: $3993 Airbnb ROI: 4% Traditional ROI: 2.79%
61 Hurtin Boulevard Smithtown, NY Welcome to 61 Hurtin Boulevard....This Spacious Brookfield Colonial features the following...	4 beds \| 3 baths \| 2,477 sq.ft.	$749,000	Airbnb cash on cash: 3.67% Traditional cash on cash: 3.57% Airbnb Rental Income: $5968 Traditional Rental Income: $4718 Airbnb ROI: 3.67% Traditional ROI: 3.57%
32 Branch Drive Smithtown, NY LOCATION LOCATION! Looking for a perfect tranquil spot to call home? This is it! Situated ...	4 beds \| 3 baths \| 2,352 sq.ft.	$1,100,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 1.65% Airbnb Rental Income: $5968 Traditional Rental Income: $4703 Airbnb ROI: 1.73% Traditional ROI: 1.65%
25 Sheryl Crescent Smithtown, NY Welcome to 25 Sheryl Crescent!! This beautifully maintained 5 Bedroom, 3.5 Bath home with ...	5 beds \| 4 baths \| 2,521 sq.ft.	$799,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.94% Airbnb Rental Income: $null Traditional Rental Income: $5360 Airbnb ROI: N/A Traditional ROI: 3.94%
64 Marquette Drive Smithtown, NY Welcome to this well-maintained 4-bedroom, 1.5-bath high ranch located in the heart of Smi...	4 beds \| 2 baths \| 2,200 sq.ft.	$849,000	Airbnb cash on cash: 3.14% Traditional cash on cash: 2.54% Airbnb Rental Income: $5968 Traditional Rental Income: $4307 Airbnb ROI: 3.14% Traditional ROI: 2.54%

Your search for investment property begins and ends here

Single Family Homes for Sale in Smithtown, NY

7 Monitor Road

Smithtown, NY

3 beds | 3 baths | 1,970 sq.ft.

$798,000

Airbnb cash on cash: 1.73%

Traditional cash on cash: 2.96%

Airbnb Rental Income: $4264

Traditional Rental Income: $4275

Airbnb ROI: 1.73%

Traditional ROI: 2.96%

8 Mulberry Drive

Smithtown, NY

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

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 Drive

Smithtown, NY

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

$789,000

Airbnb cash on cash: 3.93%

Traditional cash on cash: 2.73%

Airbnb Rental Income: $5968

Traditional Rental Income: $3905

Airbnb ROI: 3.93%

Traditional ROI: 2.73%

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%

44 Elizabeth Avenue

Smithtown, NY

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

$689,999

Airbnb cash on cash: 4.74%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $5968

Traditional Rental Income: $4336

Airbnb ROI: 4.74%

Traditional ROI: 4.05%

6 Keystone Court

Smithtown, NY

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%

7 Quincy Lane

Smithtown, NY

4 beds | 3 baths | 2,183 sq.ft.

$849,999

Airbnb cash on cash: 3.08%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $5968

Traditional Rental Income: $4888

Airbnb ROI: 3.08%