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
18 Lehigh Drive Smithtown, NY "ALL BINDERS ARE OFF" Location, Location, Location! Welcome to your dream home! This beau...	4 beds \| 2 baths \| 1,629 sq.ft.	$750,000	Airbnb cash on cash: 3.73% Traditional cash on cash: 2.49% Airbnb Rental Income: $5968 Traditional Rental Income: $3917 Airbnb ROI: 3.73% Traditional ROI: 2.49%
47 Bellemeade Avenue Smithtown, NY Step into this enchanting Craftsman-style Cape, where exquisite carpentry and charming des...	3 beds \| 2 baths \| N/A	$650,000	Airbnb cash on cash: 2.79% Traditional cash on cash: 3.45% Airbnb Rental Income: $4264 Traditional Rental Income: $3763 Airbnb ROI: 2.79% Traditional ROI: 3.45%
17 Sheppard Lane Smithtown, NY Welcome Home to This Stunning High Ranch, Perfect for Entertaining! Fully renovated in 201...	4 beds \| 2 baths \| 1,700 sq.ft.	$699,999	Airbnb cash on cash: 4.38% Traditional cash on cash: 2.95% Airbnb Rental Income: $5968 Traditional Rental Income: $3857 Airbnb ROI: 4.38% Traditional ROI: 2.95%
8 Glacier Drive Smithtown, NY Special Features. Large Paved patio Huge walk-in closet stainless steel appliances crown...	3 beds \| 4 baths \| N/A	$899,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 3.14% Airbnb Rental Income: $4264 Traditional Rental Income: $4881 Airbnb ROI: 1.32% Traditional ROI: 3.14%
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	$750,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 3.5% Airbnb Rental Income: $5968 Traditional Rental Income: $4272 Airbnb ROI: 4.23% Traditional ROI: 3.5%
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%
33 Princeton Avenue Smithtown, NY Adorable Ranch,bright and airy. Newish roof ,updated bath. Flat Usable Yard w/ Inground sa...	2 beds \| 2 baths \| N/A	$499,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 3.61% Airbnb Rental Income: $2346 Traditional Rental Income: $2857 Airbnb ROI: 1.27% Traditional ROI: 3.61%
126 N Country Road Smithtown, NY Surrounded by towering trees and abundant greenery, this beautifully updated 3-bedroom, 2-...	3 beds \| 2 baths \| 1,188 sq.ft.	$674,999	Airbnb cash on cash: 2.55% Traditional cash on cash: 2.71% Airbnb Rental Income: $4264 Traditional Rental Income: $3469 Airbnb ROI: 2.55% Traditional ROI: 2.71%
82 Terry Road Smithtown, NY Welcome to this lovely home. Renovated in 2021, this 3 bedroom Split offers a new kitchen,...	3 beds \| 1 baths \| N/A	$585,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 4.22% Airbnb Rental Income: $4516 Traditional Rental Income: $3895 Airbnb ROI: 3.63% Traditional ROI: 4.22%
5 Stone Gate #5 Smithtown, NY Hidden Gem on a Secluded cul-de-sac in the Heart of Smithtown Discover this well maintaine...	2 beds \| 4 baths \| N/A	$624,999	Airbnb cash on cash: -0.86% Traditional cash on cash: 4.21% Airbnb Rental Income: $2346 Traditional Rental Income: $4726 Airbnb ROI: -0.86% Traditional ROI: 4.21%
31 Chelsea Drive #31 Smithtown, NY Introducing a Beautiful Windcrest 3 Bedroom, 2.5 Bath Condo Located in Smithtown, NY. This...	3 beds \| 3 baths \| 2,180 sq.ft.	$789,000	Airbnb cash on cash: 0.76% Traditional cash on cash: 2.26% Airbnb Rental Income: $4264 Traditional Rental Income: $4467 Airbnb ROI: 0.76% Traditional ROI: 2.26%
36 Tanglewood Drive Smithtown, NY Welcome to this beautifully situated Hi-Ranch home in Smithtown, hauppauge school district...	4 beds \| 2 baths \| 1,840 sq.ft.	$699,999	Airbnb cash on cash: 4.98% Traditional cash on cash: 3.81% Airbnb Rental Income: $5968 Traditional Rental Income: $4020 Airbnb ROI: 4.98% Traditional ROI: 3.81%
16 Monitor Road #16 Smithtown, NY Step into luxury with this beautifully updated townhouse, the largest in the Willow Wood c...	3 beds \| 3 baths \| 1,926 sq.ft.	$699,000	Airbnb cash on cash: 1.33% Traditional cash on cash: 2.36% Airbnb Rental Income: $4264 Traditional Rental Income: $4037 Airbnb ROI: 1.33% Traditional ROI: 2.36%
20 Winston Drive Smithtown, NY Welcome to this brand-new construction Dutch Colonial in the heart of the charming Hamlet ...	5 beds \| 4 baths \| 3,400 sq.ft.	$1,649,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.63% Airbnb Rental Income: $null Traditional Rental Income: $3145 Airbnb ROI: N/A Traditional ROI: 0.63%
158 Landing Meadow Road Smithtown, NY New Construction on 1.2 Acres with Pool and Luxury Finishes! Discover Luxury Living With T...	4 beds \| 4 baths \| 3,900 sq.ft.	$1,999,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 1.06% Airbnb Rental Income: $5968 Traditional Rental Income: $5413 Airbnb ROI: 0.72% Traditional ROI: 1.06%
135 Plymouth Boulevard Smithtown, NY Spacious Colonial Splanch, LR and FR w/vaulted Ceilings, Hardwood Floors-LR/Upper Level, P...	4 beds \| 2 baths \| N/A	$711,000	Airbnb cash on cash: 4.12% Traditional cash on cash: 3.37% Airbnb Rental Income: $5968 Traditional Rental Income: $4288 Airbnb ROI: 4.12% Traditional ROI: 3.37%
Lot 19 St Nicholas Avenue Smithtown, NY To Be Built 4 Bedroom 3 Bath Colonial 2 Car Carage,4/5 Bedrooms, 3 Full Baths, Oak Floors ...	5 beds \| 3 baths \| 3,100 sq.ft.	$899,900	Airbnb cash on cash: N/A Traditional cash on cash: 3.25% Airbnb Rental Income: $null Traditional Rental Income: $5089 Airbnb ROI: N/A Traditional ROI: 3.25%
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%
789 Meadow Road Smithtown, NY Charming Cape located in the heart of Smithtown. 4 bedrooms, 2 full baths, fully renovated...	4 beds \| 2 baths \| N/A	$719,999	Airbnb cash on cash: 4.15% Traditional cash on cash: 3.12% Airbnb Rental Income: $5968 Traditional Rental Income: $4097 Airbnb ROI: 4.15% Traditional ROI: 3.12%
51 Dillmont Drive Smithtown, NY This beautiful expanded ranch sits on a generous flat 1/2 acre lot offering a perfect blen...	4 beds \| 3 baths \| 2,490 sq.ft.	$849,000	Airbnb cash on cash: 2.95% Traditional cash on cash: 2.64% Airbnb Rental Income: $5968 Traditional Rental Income: $4537 Airbnb ROI: 2.95% Traditional ROI: 2.64%
3 Maylin Court Smithtown, NY Wonderful Expanded Ranch on Cul de sac, Almost 3/4 Acre Beautiful Treed Property, Charm an...	3 beds \| 2 baths \| N/A	$649,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 3.53% Airbnb Rental Income: $4264 Traditional Rental Income: $4145 Airbnb ROI: 2.24% Traditional ROI: 3.53%
63 Woodland Lane Smithtown, NY Feast your eyes on an amazing opportunity to make this house your forever dream home with ...	5 beds \| 3 baths \| N/A	$695,000	Airbnb cash on cash: N/A Traditional cash on cash: 1% Airbnb Rental Income: $null Traditional Rental Income: $2321 Airbnb ROI: N/A Traditional ROI: 1%
16 Wyandanch Boulevard Smithtown, NY Welcome to Your Dream Home at 16 Wyandanch Blvd Nestled in the heart of picturesque Smitht...	5 beds \| 5 baths \| 2,700 sq.ft.	$824,999	Airbnb cash on cash: N/A Traditional cash on cash: 6.03% Airbnb Rental Income: $null Traditional Rental Income: $6898 Airbnb ROI: N/A Traditional ROI: 6.03%
23 Tiffany Lane Smithtown, NY Hi-Ranch, Hardwood Floors, Architectural Roof, Andersen Thermopane Windows, Gas Hot Water ...	4 beds \| 2 baths \| N/A	$659,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 3.49% Airbnb Rental Income: $5968 Traditional Rental Income: $4375 Airbnb ROI: 4.16% Traditional ROI: 3.49%
7 Platt Avenue Smithtown, NY Welcome to this BEAUTIFUL and SPACIOUS NEW renovated home situated on a quiet street in th...	5 beds \| 3 baths \| 2,500 sq.ft.	$779,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.29% Airbnb Rental Income: $null Traditional Rental Income: $4469 Airbnb ROI: N/A Traditional ROI: 3.29%
328 Edgewood Avenue Smithtown, NY Welcome to this 5 bedroom 3 bath Contemporary home set back from the road on one flat acre...	5 beds \| 3 baths \| N/A	$989,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.71% Airbnb Rental Income: $null Traditional Rental Income: $4718 Airbnb ROI: N/A Traditional ROI: 1.71%
14 Summerset Drive Smithtown, NY Location, Location, Location! This home boasts a notable 2,742 square feet of living spac...	5 beds \| 2 baths \| 2,742 sq.ft.	$849,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.34% Airbnb Rental Income: $null Traditional Rental Income: $4449 Airbnb ROI: N/A Traditional ROI: 2.34%
57 Brooksite Drive Smithtown, NY COMPLETE RENNOVATION OCTOBER 2024 Welcome to this beautifully updated 4-bedroom, 3-full-b...	4 beds \| 3 baths \| N/A	$799,990	Airbnb cash on cash: 3.39% Traditional cash on cash: 3.8% Airbnb Rental Income: $5968 Traditional Rental Income: $5087 Airbnb ROI: 3.39% Traditional ROI: 3.8%
7 Pine Ridge Drive Smithtown, NY Elegant Masterpiece in the Heart of Smithtown Pines Welcome to this exquisite, custom-...	4 beds \| 4 baths \| 4,500 sq.ft.	$1,599,000	Airbnb cash on cash: 0.92% Traditional cash on cash: 1.18% Airbnb Rental Income: $5968 Traditional Rental Income: $5180 Airbnb ROI: 0.92% Traditional ROI: 1.18%
45 Paddington Circle #45 Smithtown, NY *END UNIT TOWNHOUSE* In the Exclusive gated community of Windcrest in Smithtown. Count...	3 beds \| 3 baths \| 1,760 sq.ft.	$689,000	Airbnb cash on cash: 1.32% Traditional cash on cash: 2.37% Airbnb Rental Income: $4264 Traditional Rental Income: $4038 Airbnb ROI: 1.32% Traditional ROI: 2.37%
765 Meadow Road Smithtown, NY 2 Bedrooms, Living Room, EIK, Full unfinished basement, Full Bath. House needs TLC Please...	2 beds \| 1 baths \| 503 sq.ft.	$449,000	Airbnb cash on cash: 1.86% Traditional cash on cash: 3.53% Airbnb Rental Income: $2346 Traditional Rental Income: $2466 Airbnb ROI: 1.86% Traditional ROI: 3.53%
45 Croft Lane Smithtown, NY Finally Your Very Own Turn Key Farm In The Heart Of Horse Country! 50' From The Entrance O...	4 beds \| 3 baths \| N/A	$1,110,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 2.49% Airbnb Rental Income: $5968 Traditional Rental Income: $4821 Airbnb ROI: 2.45% Traditional ROI: 2.49%
31 Croft Lane Smithtown, NY This stunning four bedroom home in the Smithtown School District offers a perfect blend of...	4 beds \| 3 baths \| N/A	$1,100,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 0.92% Airbnb Rental Income: $5968 Traditional Rental Income: $4762 Airbnb ROI: 0.94% Traditional ROI: 0.92%
20 Mulberry Drive Smithtown, NY Beautiful Home Pride of Ownership Shows Throughout! Updates Include Roof, Eat In Kitchen, ...	4 beds \| 2 baths \| N/A	$699,990	Airbnb cash on cash: 4.07% Traditional cash on cash: 3.31% Airbnb Rental Income: $5968 Traditional Rental Income: $4284 Airbnb ROI: 4.07% Traditional ROI: 3.31%
16 Links Road Smithtown, NY Beautiful Sprawling well maintained Ranch located in much desired Pines community, half bl...	4 beds \| 4 baths \| N/A	$999,900	Airbnb cash on cash: 3.08% Traditional cash on cash: 2.16% Airbnb Rental Income: $5968 Traditional Rental Income: $3931 Airbnb ROI: 3.08% Traditional ROI: 2.16%
23 Dartmouth Drive Smithtown, NY Come see this stunning immaculate,move in ready ranch located in the heart of the desireab...	3 beds \| 2 baths \| N/A	$659,999	Airbnb cash on cash: 2.66% Traditional cash on cash: 4.27% Airbnb Rental Income: $4264 Traditional Rental Income: $4358 Airbnb ROI: 2.66% Traditional ROI: 4.27%
10 South Avenue Smithtown, NY Great Opportunity with Smithtown Schools/Cute Ranch on Large flat 1/2 Acre lot/Detached 1....	3 beds \| 2 baths \| N/A	$624,999	Airbnb cash on cash: 3.29% Traditional cash on cash: 3.97% Airbnb Rental Income: $4264 Traditional Rental Income: $3762 Airbnb ROI: 3.29% Traditional ROI: 3.97%
23 Dunedin Street Smithtown, NY Gorgeous Colonial/Splanch featuring beautiful Entrance hall, Formal Dining Room, Eat in Ki...	5 beds \| 3 baths \| 2,865 sq.ft.	$785,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.72% Airbnb Rental Income: $null Traditional Rental Income: $4949 Airbnb ROI: N/A Traditional ROI: 3.72%
14 Sandpiper Court Smithtown, NY Nestled on a serene cul-de-sac, this stunning colonial home offers 4 spacious bedrooms and...	4 beds \| 3 baths \| N/A	$999,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 2.17% Airbnb Rental Income: $5968 Traditional Rental Income: $4938 Airbnb ROI: 2.01% Traditional ROI: 2.17%
34 Averly Place Smithtown, NY If you're looking for drama, this house is it!!! Architecturally unique with impressive e...	5 beds \| 4 baths \| N/A	$1,100,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.46% Airbnb Rental Income: $null Traditional Rental Income: $4047 Airbnb ROI: N/A Traditional ROI: 1.46%

Real Estate investment in Smithtown, NY

There are 86 properties for sale in the city of Smithtown . The median list price in Smithtown is $787,000 and the average price per square foot is $317. In December 2024, the average monthly cash on cash return in Smithtown is 3.00%. The average monthly rental income in Smithtown is $4,407.

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

There are 86 investment properties available for sale in Smithtown.

In 2024, the best neighborhood to buy investment property is Smithtown.

The ROI for Short-Term is higher than the Long-Term in Smithtown with average rental income of $5,968.

Your search for investment property begins and ends here

Investment Property for Sale in Smithtown, NY

18 Lehigh Drive

Smithtown, NY

4 beds | 2 baths | 1,629 sq.ft.

$750,000

Airbnb cash on cash: 3.73%

Traditional cash on cash: 2.49%

Airbnb Rental Income: $5968

Traditional Rental Income: $3917

Airbnb ROI: 3.73%

Traditional ROI: 2.49%

47 Bellemeade Avenue

Smithtown, NY

3 beds | 2 baths | N/A

$650,000

Airbnb cash on cash: 2.79%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $4264

Traditional Rental Income: $3763

Airbnb ROI: 2.79%

Traditional ROI: 3.45%

17 Sheppard Lane

Smithtown, NY

4 beds | 2 baths | 1,700 sq.ft.

$699,999

Airbnb cash on cash: 4.38%

Traditional cash on cash: 2.95%

Airbnb Rental Income: $5968

Traditional Rental Income: $3857

Airbnb ROI: 4.38%

Traditional ROI: 2.95%

8 Glacier Drive

Smithtown, NY

3 beds | 4 baths | N/A

$899,000

Airbnb cash on cash: 1.32%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $4264

Traditional Rental Income: $4881

Airbnb ROI: 1.32%

Traditional ROI: 3.14%

12 Darling Avenue

Smithtown, NY

4 beds | 2 baths | N/A

$750,000

Airbnb cash on cash: 4.23%

Traditional cash on cash: 3.5%

Airbnb Rental Income: $5968

Traditional Rental Income: $4272

Airbnb ROI: 4.23%

Traditional ROI: 3.5%

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%

33 Princeton Avenue

Smithtown, NY

2 beds | 2 baths | N/A

$499,000

Airbnb cash on cash: 1.27%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $2346

Traditional Rental Income: $2857

Airbnb ROI: 1.27%

Traditional ROI: 3.61%

126 N Country Road

Smithtown, NY

3 beds | 2 baths | 1,188 sq.ft.

$674,999

Airbnb cash on cash: 2.55%

Traditional cash on cash: 2.71%

Airbnb Rental Income: $4264

Traditional Rental Income: $3469

Airbnb ROI: 2.55%