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 70 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
45 Grandview Lane Smithtown, NY LARGE 4 BEDROOM 2.5 BATH COLONIAL ON 1.23 ACRES OF PARKLIKE PROPERTY IN THE PINES SECTION ...	4 beds \| 3 baths \| 2,924 sq.ft.	$999,999	Airbnb cash on cash: 2.54% Traditional cash on cash: 2.66% Airbnb Rental Income: $5968 Traditional Rental Income: $4896 Airbnb ROI: 2.54% Traditional ROI: 2.66%
105 Lone Oak Path Smithtown, NY Beautifully situated in The Pines of Smithtown, this charming 3-bedroom, 2-bath Colonial w...	3 beds \| 2 baths \| N/A	$829,000	Airbnb cash on cash: 1.76% Traditional cash on cash: 2.19% Airbnb Rental Income: $4264 Traditional Rental Income: $3695 Airbnb ROI: 1.76% Traditional ROI: 2.19%
210 Landing Avenue Smithtown, NY Welcome 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: 2.96% Traditional cash on cash: 2.85% Airbnb Rental Income: $4264 Traditional Rental Income: $3289 Airbnb ROI: 2.96% Traditional ROI: 2.85%
61 Redan Drive Smithtown, NY Love Where You Live While Enjoying a Carefree Life Style in this Prestigious Gated Golf Co...	3 beds \| 3 baths \| 2,740 sq.ft.	$1,185,000	Airbnb cash on cash: 0.01% Traditional cash on cash: 0.93% Airbnb Rental Income: $4264 Traditional Rental Income: $4374 Airbnb ROI: 0.01% Traditional ROI: 0.93%
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%
79 Oakside Road Smithtown, NY Welcome to 79 Oakside Road, a custom-built haven nestled in the heart of Smithtown, NY. Bu...	4 beds \| 3 baths \| 2,800 sq.ft.	$1,150,990	Airbnb cash on cash: 1.8% Traditional cash on cash: 1.46% Airbnb Rental Income: $5968 Traditional Rental Income: $4416 Airbnb ROI: 1.8% Traditional ROI: 1.46%
40 Friendly Road Smithtown, NY Welcome 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 Traditional cash on cash: 0.92% Airbnb Rental Income: $null Traditional Rental Income: $4205 Airbnb ROI: N/A Traditional ROI: 0.92%
158 Landing Meadow Road Smithtown, NY Welcome to 158 Landing Meadow Road! Renovated on 1.2 Acres With Pool and Luxury Finishes! ...	4 beds \| 4 baths \| 3,634 sq.ft.	$1,500,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 1.65% Airbnb Rental Income: $5968 Traditional Rental Income: $5413 Airbnb ROI: 1.19% Traditional ROI: 1.65%
44 Elizabeth Avenue Smithtown, NY Adorable 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% Traditional cash on cash: 5.96% Airbnb Rental Income: $5968 Traditional Rental Income: $4336 Airbnb ROI: 6.88% Traditional ROI: 5.96%
26 Lindner Smithtown, NY Welcome 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% Traditional cash on cash: 3.31% Airbnb Rental Income: $5968 Traditional Rental Income: $4095 Airbnb ROI: 4.41% Traditional ROI: 3.31%
16 Wildwood Lane Smithtown, NY House For Sale.	5 beds \| 3 baths \| 2,204 sq.ft.	$850,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.88% Airbnb Rental Income: $null Traditional Rental Income: $5014 Airbnb ROI: N/A Traditional ROI: 2.88%
24 Croft Lane Smithtown, NY Experience the Ultimate Equestrian Lifestyle With This Stunning Expanded Ranch Home and Ho...	5 beds \| 4 baths \| 2,600 sq.ft.	$1,179,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.68% Airbnb Rental Income: $null Traditional Rental Income: $5864 Airbnb ROI: N/A Traditional ROI: 2.68%
147 Juniper Avenue Smithtown, NY Welcome 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: 2.27% Traditional cash on cash: 2% Airbnb Rental Income: $4264 Traditional Rental Income: $3187 Airbnb ROI: 2.27% Traditional ROI: 2%
25 Whispering Woods Drive Smithtown, NY This 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% Traditional cash on cash: 1.89% Airbnb Rental Income: $5968 Traditional Rental Income: $4835 Airbnb ROI: 1.83% Traditional ROI: 1.89%
6 Keystone Court Smithtown, NY Last Home To Be Built In This Cul-de-sac. Rendering/Photo Shown Conveys Craftsmanship of ...	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%
Lot 21 Hurtin Boulevard Smithtown, NY NEW 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 Traditional cash on cash: 3.05% Airbnb Rental Income: $null Traditional Rental Income: $4851 Airbnb ROI: N/A Traditional ROI: 3.05%
29 Bayberry Lane Smithtown, NY Construction 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% Traditional cash on cash: 1.42% Airbnb Rental Income: $5968 Traditional Rental Income: $4635 Airbnb ROI: 1.56% Traditional ROI: 1.42%
1 Charter Lane Smithtown, NY Come 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: 1.65% Traditional cash on cash: 3.27% Airbnb Rental Income: $4264 Traditional Rental Income: $4538 Airbnb ROI: 1.65% Traditional ROI: 3.27%
3 Ingram Court Smithtown, NY Nestled 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% Traditional cash on cash: 4.16% Airbnb Rental Income: $5968 Traditional Rental Income: $6334 Airbnb ROI: 2.46% Traditional ROI: 4.16%
271 N Country Road Smithtown, NY Introducing 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% Traditional cash on cash: 3.39% Airbnb Rental Income: $5968 Traditional Rental Income: $4951 Airbnb ROI: 3.21% Traditional ROI: 3.39%
9 Graystone Lane Smithtown, NY Welcome to 9 Graystone Lane - An Entertainers Delight!! This beautiful 4 bed, 2.5 bath col...	4 beds \| 3 baths \| 3,264 sq.ft.	$869,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 3.23% Airbnb Rental Income: $5968 Traditional Rental Income: $5056 Airbnb ROI: 2.89% Traditional ROI: 3.23%
206 Brooksite Drive Smithtown, NY Lovely Smithtown Living! Enjoy This Beautifully Designed and Maintained Home Which Feature...	4 beds \| 4 baths \| 3,000 sq.ft.	$1,100,000	Airbnb cash on cash: 2.2% Traditional cash on cash: 3.22% Airbnb Rental Income: $5968 Traditional Rental Income: $5827 Airbnb ROI: 2.2% Traditional ROI: 3.22%
4 Candlelight Court Smithtown, NY Welcome to this Custom Contemporized Colonial W/ Two Story Entrance Foyer, Vaulted Ceiling...	3 beds \| 3 baths \| 2,922 sq.ft.	$885,000	Airbnb cash on cash: 0.59% Traditional cash on cash: 1.94% Airbnb Rental Income: $4264 Traditional Rental Income: $4475 Airbnb ROI: 0.59% Traditional ROI: 1.94%
36 Woodland Lane Smithtown, NY Inviting, 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 Traditional cash on cash: 2.43% Airbnb Rental Income: $null Traditional Rental Income: $5258 Airbnb ROI: N/A Traditional ROI: 2.43%
44 Croft Lane Smithtown, NY Welcome 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: 0.14% Traditional cash on cash: 2.44% Airbnb Rental Income: $4264 Traditional Rental Income: $5877 Airbnb ROI: 0.14% Traditional ROI: 2.44%
40 Dillmont Drive Smithtown, NY Welcome home to this absolutely spectacular dream home nestled on just shy of an acre of l...	5 beds \| 3 baths \| 2,580 sq.ft.	$849,999	Airbnb cash on cash: N/A Traditional cash on cash: 3.46% Airbnb Rental Income: $null Traditional Rental Income: $5133 Airbnb ROI: N/A Traditional ROI: 3.46%
4 Nadia Court Smithtown, NY Welcome to 4 Nadia Court, a custom-designed 5 bedroom, 4.5 bath masterpiece nestled in on...	5 beds \| 5 baths \| 4,677 sq.ft.	$2,049,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.46% Airbnb Rental Income: $null Traditional Rental Income: $7836 Airbnb ROI: N/A Traditional ROI: 1.46%
109 Oakside Drive Smithtown, NY Welcome to 109 Oakside Dr., your dream equestrian retreat, set on 2 scenic acres in the he...	4 beds \| 4 baths \| 2,400 sq.ft.	$1,499,990	Airbnb cash on cash: 0.42% Traditional cash on cash: 1.07% Airbnb Rental Income: $5968 Traditional Rental Income: $5692 Airbnb ROI: 0.42% Traditional ROI: 1.07%
7 Village Way Smithtown, NY Beautiful Home fully renovated in the last few years. Large spacious rooms with beautiful ...	3 beds \| 3 baths \| 2,400 sq.ft.	$749,990	Airbnb cash on cash: 1.32% Traditional cash on cash: 2.94% Airbnb Rental Income: $4264 Traditional Rental Income: $4499 Airbnb ROI: 1.32% Traditional ROI: 2.94%
38 McArthur Lane Smithtown, NY Welcome 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 Traditional cash on cash: 3.96% Airbnb Rental Income: $null Traditional Rental Income: $5004 Airbnb ROI: N/A Traditional ROI: 3.96%
16 Crawford Street Smithtown, NY Welcome to 16 Crawford Street, Smithtown! Nestled in the heart of desirable Smithtown, th...	4 beds \| 3 baths \| 2,890 sq.ft.	$874,000	Airbnb cash on cash: 2.9% Traditional cash on cash: 3.5% Airbnb Rental Income: $5968 Traditional Rental Income: $5268 Airbnb ROI: 2.9% Traditional ROI: 3.5%
11 Dillmont Drive Smithtown, NY Majestic, Expanded Center Hall Colonial, 4 BR, 2.5 Baths on Usable 1/2 Acre Plus Property ...	4 beds \| 3 baths \| 2,900 sq.ft.	$1,050,000	Airbnb cash on cash: 1.96% Traditional cash on cash: 2.39% Airbnb Rental Income: $5968 Traditional Rental Income: $5205 Airbnb ROI: 1.96% Traditional ROI: 2.39%
592 Landing Avenue Smithtown, NY Completely Renovated Historic 3 story Colonial on private 1.3 Acre parcel with circular dr...	5 beds \| 3 baths \| 4,000 sq.ft.	$1,250,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.55% Airbnb Rental Income: $null Traditional Rental Income: $5114 Airbnb ROI: N/A Traditional ROI: 1.55%
32 Merrivale Drive Smithtown, NY Here's your chance to live in the desirable Sunnydale section of Smithtown!! This spacious...	5 beds \| 3 baths \| 2,670 sq.ft.	$975,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.63% Airbnb Rental Income: $null Traditional Rental Income: $5553 Airbnb ROI: N/A Traditional ROI: 3.63%
18 Thrush Drive Smithtown, NY This Gorgeous Ranch is a rare gem nestled in the Forestwood section of Smithtown. This dis...	4 beds \| 2 baths \| 2,000 sq.ft.	$899,990	Airbnb cash on cash: 2.79% Traditional cash on cash: 2.27% Airbnb Rental Income: $5968 Traditional Rental Income: $4351 Airbnb ROI: 2.79% Traditional ROI: 2.27%
74 Laurel Drive Smithtown, NY Welcome to THE PINES, experience exceptional resort-style living in this custom Smithtown ...	5 beds \| 6 baths \| 3,800 sq.ft.	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.86% Airbnb Rental Income: $null Traditional Rental Income: $8702 Airbnb ROI: N/A Traditional ROI: 3.86%
365 Route 111 #C-4 Smithtown, NY Welcome to this beautifully updated co-op featuring an open floor plan that seamlessly com...	1 beds \| 1 baths \| 1,000 sq.ft.	$245,000	Airbnb cash on cash: -3.51% Traditional cash on cash: 0.85% Airbnb Rental Income: $1593 Traditional Rental Income: $2149 Airbnb ROI: -3.51% Traditional ROI: 0.85%
49 Dorchester Road Smithtown, NY Welcome home to 49 Dorchester Rd!! This diamond renovated colonial is the one you've been ...	4 beds \| 3 baths \| 2,200 sq.ft.	$914,999	Airbnb cash on cash: 2.98% Traditional cash on cash: 2.84% Airbnb Rental Income: $5968 Traditional Rental Income: $4663 Airbnb ROI: 2.98% Traditional ROI: 2.84%
58 Rhoda Avenue Smithtown, NY Expanded Colonial with Huge Family Room with Propane Gas Fireplace/Laundry room Convenient...	3 beds \| 3 baths \| 2,462 sq.ft.	$779,999	Airbnb cash on cash: 1.56% Traditional cash on cash: 3.12% Airbnb Rental Income: $4264 Traditional Rental Income: $4497 Airbnb ROI: 1.56% Traditional ROI: 3.12%
75 Parnell Drive Smithtown, NY Welcome to this beautifully updated Raised Ranch, set on a shy half-acre cul-de-sac lot an...	5 beds \| 2 baths \| 1,892 sq.ft.	$820,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.93% Airbnb Rental Income: $null Traditional Rental Income: $4355 Airbnb ROI: N/A Traditional ROI: 2.93%

Your search for investment property begins and ends here

Single Family Homes for Sale in Smithtown, NY

45 Grandview Lane

Smithtown, NY

4 beds | 3 baths | 2,924 sq.ft.

$999,999

Airbnb cash on cash: 2.54%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $5968

Traditional Rental Income: $4896

Airbnb ROI: 2.54%

Traditional ROI: 2.66%

105 Lone Oak Path

Smithtown, NY

3 beds | 2 baths | N/A

$829,000

Airbnb cash on cash: 1.76%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $4264

Traditional Rental Income: $3695

Airbnb ROI: 1.76%

Traditional ROI: 2.19%

210 Landing Avenue

Smithtown, NY

3 beds | 2 baths | 1,300 sq.ft.

$699,000

Airbnb cash on cash: 2.96%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $4264

Traditional Rental Income: $3289

Airbnb ROI: 2.96%

Traditional ROI: 2.85%

61 Redan Drive

Smithtown, NY

3 beds | 3 baths | 2,740 sq.ft.

$1,185,000

Airbnb cash on cash: 0.01%

Traditional cash on cash: 0.93%

Airbnb Rental Income: $4264

Traditional Rental Income: $4374

Airbnb ROI: 0.01%

Traditional ROI: 0.93%

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%

79 Oakside Road

Smithtown, NY

4 beds | 3 baths | 2,800 sq.ft.

$1,150,990

Airbnb cash on cash: 1.8%

Traditional cash on cash: 1.46%

Airbnb Rental Income: $5968

Traditional Rental Income: $4416

Airbnb ROI: 1.8%

Traditional ROI: 1.46%

40 Friendly Road

Smithtown, NY

5 beds | 4 baths | 2,700 sq.ft.

$1,675,000

Airbnb cash on cash: N/A

Traditional cash on cash: 0.92%

Airbnb Rental Income: $null

Traditional Rental Income: $4205

Airbnb ROI: N/A

Traditional ROI: 0.92%

158 Landing Meadow Road

Smithtown, NY

4 beds | 4 baths | 3,634 sq.ft.

$1,500,000

Airbnb cash on cash: 1.19%

Traditional cash on cash: 1.65%

Airbnb Rental Income: $5968

Traditional Rental Income: $5413

Airbnb ROI: 1.19%