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

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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%
9 Mulberry Drive Smithtown, NY Beautiful 4-Bedroom, 2-Bath Home with Exceptional Amenities. Owner is motivated to sell, a...	4 beds \| 2 baths \| 1,834 sq.ft.	$895,000	Airbnb cash on cash: 3.1% Traditional cash on cash: 2.46% Airbnb Rental Income: $5968 Traditional Rental Income: $4250 Airbnb ROI: 3.1% Traditional ROI: 2.46%
203 Pond View Lane Smithtown, NY Welcome to this bright and spacious 2 story Condo in the gated community of Hidden Ponds. ...	1 beds \| 2 baths \| 1,044 sq.ft.	$475,000	Airbnb cash on cash: -1.25% Traditional cash on cash: 2.05% Airbnb Rental Income: $1739 Traditional Rental Income: $2727 Airbnb ROI: -1.25% Traditional ROI: 2.05%
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%
131 Oakside Drive Smithtown, NY Perched atop a scenic hill in one of Smithtown's most prestigious enclaves, this architect...	4 beds \| 3 baths \| 3,300 sq.ft.	$1,375,000	Airbnb cash on cash: 1.16% Traditional cash on cash: 1.48% Airbnb Rental Income: $5968 Traditional Rental Income: $5192 Airbnb ROI: 1.16% Traditional ROI: 1.48%
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%
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: -1.57% Traditional cash on cash: 2% Airbnb Rental Income: $1259 Traditional Rental Income: $3187 Airbnb ROI: -1.57% 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%
62 Laurel Drive Smithtown, NY Fabulous ranch!!! Summer is coming and this oasis is waiting for YOU! Gorgeous home decora...	3 beds \| 3 baths \| 2,000 sq.ft.	$1,299,000	Airbnb cash on cash: 0.73% Traditional cash on cash: 2.01% Airbnb Rental Income: $4264 Traditional Rental Income: $4915 Airbnb ROI: 0.73% Traditional ROI: 2.01%
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%
23 Ridge Court Smithtown, NY NO ACCESS, DRIVE BY ONLY TENANTS INSIDE. WILL BE DELIVERD VACANT. Beautiful house in perfe...	5 beds \| 3 baths \| 2,400 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.54% Airbnb Rental Income: $null Traditional Rental Income: $4536 Airbnb ROI: N/A Traditional ROI: 3.54%
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%
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%
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.	$1,450,000	Airbnb cash on cash: 0.46% Traditional cash on cash: 1.14% Airbnb Rental Income: $5968 Traditional Rental Income: $5692 Airbnb ROI: 0.46% Traditional ROI: 1.14%
239 Pond View Lane Smithtown, NY Smithtown Townhome now showing! Spacious Dartmouth model in preferred Hidden Ponds Condom...	3 beds \| 3 baths \| 1,800 sq.ft.	$679,990	Airbnb cash on cash: 1.99% Traditional cash on cash: 2.99% Airbnb Rental Income: $4264 Traditional Rental Income: $3999 Airbnb ROI: 1.99% Traditional ROI: 2.99%
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%
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.	$1,195,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.66% Airbnb Rental Income: $null Traditional Rental Income: $5114 Airbnb ROI: N/A Traditional ROI: 1.66%
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: -3.25% Traditional cash on cash: 0.85% Airbnb Rental Income: $1665 Traditional Rental Income: $2149 Airbnb ROI: -3.25% 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%
10 Quincy Lane Smithtown, NY Immaculate 4-bedroom, 2.5-bath Center Hall Colonial. The entry foyer leads to a large livi...	4 beds \| 3 baths \| 2,700 sq.ft.	$749,803	Airbnb cash on cash: 3.59% Traditional cash on cash: 3.19% Airbnb Rental Income: $5968 Traditional Rental Income: $4510 Airbnb ROI: 3.59% Traditional ROI: 3.19%
34 MOREWOOD DRIVE Smithtown, NY MAGNIFICENT 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% Traditional cash on cash: 2.31% Airbnb Rental Income: $5968 Traditional Rental Income: $4025 Airbnb ROI: 3.27% Traditional ROI: 2.31%
365 Route 111 #A4 Smithtown, NY Beautifully updated unit with laminate hardwood floors throughout The living room is spaci...	1 beds \| 1 baths \| 800 sq.ft.	$249,990	Airbnb cash on cash: 1.99% Traditional cash on cash: 6.03% Airbnb Rental Income: $1665 Traditional Rental Income: $2154 Airbnb ROI: 1.99% Traditional ROI: 6.03%
27 Enchanted Forest Road Smithtown, NY Welcome to your dream home! This beautifully updated colonial exudes warmth and charm, off...	5 beds \| 4 baths \| 2,850 sq.ft.	$1,295,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.9% Airbnb Rental Income: $null Traditional Rental Income: $5542 Airbnb ROI: N/A Traditional ROI: 1.9%
108 Hidden Ponds Circle Smithtown, NY Welcome to Hidden Ponds, a beautiful gated community in Smithtown! This two-story townhous...	3 beds \| 3 baths \| 1,800 sq.ft.	$729,000	Airbnb cash on cash: 1.69% Traditional cash on cash: 2.66% Airbnb Rental Income: $4264 Traditional Rental Income: $4022 Airbnb ROI: 1.69% Traditional ROI: 2.66%
4 Burham Court Smithtown, NY Welcome to 4 Burham Court located on a private Cul-De-Sac in the heart of North Smithtown....	3 beds \| 2 baths \| 1,918 sq.ft.	$935,000	Airbnb cash on cash: 1.04% Traditional cash on cash: 1.49% Airbnb Rental Income: $4264 Traditional Rental Income: $3758 Airbnb ROI: 1.04% Traditional ROI: 1.49%
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: 2.72% Traditional cash on cash: 4.27% Airbnb Rental Income: $5968 Traditional Rental Income: $5983 Airbnb ROI: 2.72% Traditional ROI: 4.27%

Real Estate investment in Smithtown, NY

There are 81 properties for sale in the city of Smithtown . The median list price in Smithtown is $799,000 and the average price per square foot is $362. In December 2025, the average monthly cash on cash return in Smithtown is 3.00%. The average monthly rental income in Smithtown is $4,378.

Smithtown, NY Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 81 investment properties available for sale in Smithtown.

In 2025, the best neighborhood to buy investment property is Smithtown.

The ROI for Long-Term is higher than the Short-Term in Smithtown with average rental income of $4,378.

Your search for investment property begins and ends here

Investment Property for Sale in Smithtown, NY

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%

9 Mulberry Drive

Smithtown, NY

4 beds | 2 baths | 1,834 sq.ft.

$895,000

Airbnb cash on cash: 3.1%

Traditional cash on cash: 2.46%

Airbnb Rental Income: $5968

Traditional Rental Income: $4250

Airbnb ROI: 3.1%

Traditional ROI: 2.46%

203 Pond View Lane

Smithtown, NY

1 beds | 2 baths | 1,044 sq.ft.

$475,000

Airbnb cash on cash: -1.25%

Traditional cash on cash: 2.05%

Airbnb Rental Income: $1739

Traditional Rental Income: $2727

Airbnb ROI: -1.25%

Traditional ROI: 2.05%

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%

131 Oakside Drive

Smithtown, NY

4 beds | 3 baths | 3,300 sq.ft.

$1,375,000

Airbnb cash on cash: 1.16%

Traditional cash on cash: 1.48%

Airbnb Rental Income: $5968

Traditional Rental Income: $5192

Airbnb ROI: 1.16%

Traditional ROI: 1.48%

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%

Traditional ROI: 1.65%

44 Elizabeth Avenue

Smithtown, NY

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%