Real Estate Investment Properties for Sale in Longwood, FL

Looking for investment property in Longwood, FL with high ROI ?

Explore a variety of short-term homes & houses in Longwood, FL. Invest wisely with VRBO & Longwood, FL 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 Longwood, FL

Search for Single Family Residential for Sale in Longwood, Florida. 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 88 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
3235 WINDING PINE TRAIL Longwood, FL Life unfolds beautifully in this golf front estate in the desirable guard gated community ...	4 beds \| 6 baths \| 4,262 sq.ft.	$1,350,000	Airbnb cash on cash: 1.18% Traditional cash on cash: 3.96% Airbnb Rental Income: $5377 Traditional Rental Income: $7787 Airbnb ROI: 1.18% Traditional ROI: 3.96%
899 LORMANN CIRCLE Longwood, FL Welcome to your Longwood retreat. Enjoy the peace of mind that comes with no HOA! This me...	3 beds \| 2 baths \| 969 sq.ft.	$299,490	Airbnb cash on cash: 7.12% Traditional cash on cash: 4.66% Airbnb Rental Income: $3221 Traditional Rental Income: $1803 Airbnb ROI: 7.12% Traditional ROI: 4.66%
364 HOWARD BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to this charming 3-bedroom, 2-bath home tu...	3 beds \| 2 baths \| 1,428 sq.ft.	$370,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 4.26% Airbnb Rental Income: $3221 Traditional Rental Income: $2122 Airbnb ROI: 5.33% Traditional ROI: 4.26%
153 Duncan Trl Longwood, FL Property Highlights: (2024) NEW Architectural roof + gutters/guards. (2024) Full-Home PEX ...	3 beds \| 2 baths \| 2,596 sq.ft.	$539,900	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.57% Airbnb Rental Income: $3221 Traditional Rental Income: $2588 Airbnb ROI: 3.38% Traditional ROI: 3.57%
449 SPRINGWOOD COURT Longwood, FL Under contract-accepting backup offers. This beautifully updated three-bedroom, two-bath h...	3 beds \| 2 baths \| 1,075 sq.ft.	$317,500	Airbnb cash on cash: 5.99% Traditional cash on cash: 3.78% Airbnb Rental Income: $3221 Traditional Rental Income: $1834 Airbnb ROI: 5.99% Traditional ROI: 3.78%
162 DUNCAN TRAIL Longwood, FL Under contract-accepting backup offers. Step into this updated 4-bed, 2-bath home that sit...	4 beds \| 2 baths \| 1,907 sq.ft.	$450,000	Airbnb cash on cash: 8.09% Traditional cash on cash: 3.76% Airbnb Rental Income: $5377 Traditional Rental Income: $2468 Airbnb ROI: 8.09% Traditional ROI: 3.76%
230 HOWARD BOULEVARD Longwood, FL Welcome to this beautifully updated 3-bedroom, 2-bath single-family home located in the he...	3 beds \| 2 baths \| 1,173 sq.ft.	$262,000	Airbnb cash on cash: 7.54% Traditional cash on cash: 5.43% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 7.54% Traditional ROI: 5.43%
731 CRESTBROOK LOOP Longwood, FL Welcome to 731 Crestbrook Loop in The Landings- one of Longwoodâs most desirable gated ...	3 beds \| 3 baths \| 2,140 sq.ft.	$405,000	Airbnb cash on cash: 4.26% Traditional cash on cash: 6.05% Airbnb Rental Income: $3221 Traditional Rental Income: $3173 Airbnb ROI: 4.26% Traditional ROI: 6.05%
1889 RANCHLAND TRAIL Longwood, FL Exquisite 4-Bedroom Estate with Pool on 2+ Acres in the Coveted LongwoodâLake Mary Area,...	4 beds \| 3 baths \| 2,333 sq.ft.	$989,000	Airbnb cash on cash: 2.96% Traditional cash on cash: 1.83% Airbnb Rental Income: $5377 Traditional Rental Income: $3252 Airbnb ROI: 2.96% Traditional ROI: 1.83%
4 WOODEN SHOE LANE Longwood, FL Under contract-accepting backup offers. Short Sale. Must See 4 bed, 2 bath home in the est...	4 beds \| 2 baths \| 2,682 sq.ft.	$350,000	Airbnb cash on cash: 9.51% Traditional cash on cash: 5.03% Airbnb Rental Income: $5377 Traditional Rental Income: $2819 Airbnb ROI: 9.51% Traditional ROI: 5.03%
210 BANBURY COURT Longwood, FL New Improved Price!! Your new pool home in the desirable Wekiva Hills community is waiting...	4 beds \| 2 baths \| 2,720 sq.ft.	$430,000	Airbnb cash on cash: 9.27% Traditional cash on cash: 6.61% Airbnb Rental Income: $5377 Traditional Rental Income: $3220 Airbnb ROI: 9.27% Traditional ROI: 6.61%
150 ESSEX DRIVE Longwood, FL Step into the warmth and charm of this rare cabin-style retreat nestled in the heart of Lo...	3 beds \| 2 baths \| 1,449 sq.ft.	$432,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 3.16% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.89% Traditional ROI: 3.16%
501 RIVERBEND BOULEVARD Longwood, FL Under contract-accepting backup offers. Are you ready to finally add the most important ke...	4 beds \| 2 baths \| 2,559 sq.ft.	$583,000	Airbnb cash on cash: 5.41% Traditional cash on cash: 2.71% Airbnb Rental Income: $5377 Traditional Rental Income: $2824 Airbnb ROI: 5.41% Traditional ROI: 2.71%
448 VILLAGE VIEW LANE Longwood, FL Under contract-accepting backup offers. Step inside this beautifully upgraded Sabal Point ...	5 beds \| 3 baths \| 2,634 sq.ft.	$715,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.16% Airbnb Rental Income: $null Traditional Rental Income: $2938 Airbnb ROI: N/A Traditional ROI: 2.16%
674 PINE SHADOW COURT Longwood, FL Under contract-accepting backup offers. Discover this beautifully maintained 4-bedroom, 3-...	4 beds \| 3 baths \| 2,754 sq.ft.	$710,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.41% Airbnb Rental Income: $5377 Traditional Rental Income: $3403 Airbnb ROI: 4.75% Traditional ROI: 3.41%
2010 E Triangle Drive Longwood, FL Step Inside Your Future Home! This beautiful 3-bedroom, 2-bath, 1,684 sq ft home has been ...	3 beds \| 2 baths \| 1,684 sq.ft.	$344,900	Airbnb cash on cash: 5.45% Traditional cash on cash: 4.98% Airbnb Rental Income: $3221 Traditional Rental Income: $2342 Airbnb ROI: 5.45% Traditional ROI: 4.98%
990 BURLWOOD COURT Longwood, FL Welcome to refined elegance in the gated Longwood Club community with the GRAND entrance y...	5 beds \| 4 baths \| 3,184 sq.ft.	$749,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.29% Airbnb Rental Income: $null Traditional Rental Income: $4300 Airbnb ROI: N/A Traditional ROI: 4.29%
851 N WAYMAN STREET Longwood, FL Under contract-accepting backup offers. Welcome to this beautifully updated Longwood pool ...	3 beds \| 2 baths \| 1,353 sq.ft.	$360,000	Airbnb cash on cash: 5.88% Traditional cash on cash: 4.89% Airbnb Rental Income: $3221 Traditional Rental Income: $2160 Airbnb ROI: 5.88% Traditional ROI: 4.89%
430 BRASSIE DRIVE Longwood, FL This 4-bed 3 bathroom home in Longwood offers multi-generational flexibility, over 2,500 s...	4 beds \| 3 baths \| 2,537 sq.ft.	$550,000	Airbnb cash on cash: 6.78% Traditional cash on cash: 4.61% Airbnb Rental Income: $5377 Traditional Rental Income: $3177 Airbnb ROI: 6.78% Traditional ROI: 4.61%
1510 PELICAN STREET Longwood, FL Under contract-accepting backup offers. 3-bed, 2-bath residence nestled on a serene, tree-...	3 beds \| 2 baths \| 1,269 sq.ft.	$268,900	Airbnb cash on cash: 6.8% Traditional cash on cash: 4.74% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 6.8% Traditional ROI: 4.74%
1821 STANLEY STREET Longwood, FL Under contract-accepting backup offers. Welcome to this charming and spacious home tucked ...	3 beds \| 2 baths \| 2,567 sq.ft.	$485,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 3.53% Airbnb Rental Income: $3221 Traditional Rental Income: $2427 Airbnb ROI: 3.68% Traditional ROI: 3.53%
322 N SHADOWBAY BOULEVARD Longwood, FL Welcome to Lake Vista at Shadowbay - No HOA and No Restrictions! This beautiful and well-m...	3 beds \| 2 baths \| 1,599 sq.ft.	$525,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.25% Airbnb Rental Income: $3221 Traditional Rental Income: $2395 Airbnb ROI: 3.45% Traditional ROI: 3.25%
1581 MONICA JOY CIRCLE Longwood, FL Located in TOP RATED SEMINOLE COUNTY SCHOOL DISTRICT. Single story ranch home on a cul de ...	4 beds \| 2 baths \| 2,073 sq.ft.	$469,900	Airbnb cash on cash: 7.97% Traditional cash on cash: 4.04% Airbnb Rental Income: $5377 Traditional Rental Income: $2564 Airbnb ROI: 7.97% Traditional ROI: 4.04%
975 CROSS CUT WAY Longwood, FL Beautiful 4 bedroom 2.5 bathroom home Freshly Painted with Luxury Vinyl flooring and Stain...	4 beds \| 3 baths \| 2,289 sq.ft.	$470,000	Airbnb cash on cash: 7.17% Traditional cash on cash: 4.19% Airbnb Rental Income: $5377 Traditional Rental Income: $2982 Airbnb ROI: 7.17% Traditional ROI: 4.19%
2330 PLEASANT DRIVE Longwood, FL One or more photo(s) has been virtually staged. Completely renovated and move-in ready, th...	3 beds \| 2 baths \| 1,311 sq.ft.	$395,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 5.03% Airbnb Rental Income: $3221 Traditional Rental Income: $2491 Airbnb ROI: 5.04% Traditional ROI: 5.03%
721 ROCK CREEK LOOP Longwood, FL One or more photo(s) has been virtually staged. 100-Day Home Warranty coverage available a...	3 beds \| 3 baths \| 1,998 sq.ft.	$390,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 4.79% Airbnb Rental Income: $3221 Traditional Rental Income: $2704 Airbnb ROI: 4.22% Traditional ROI: 4.79%
183 PARSONS ROAD Longwood, FL Escape into peace, nature and privacy on 12.3 acres of delightful Old Florida property. Wa...	4 beds \| 3 baths \| 3,731 sq.ft.	$5,800,000	Airbnb cash on cash: -0.49% Traditional cash on cash: -0.68% Airbnb Rental Income: $5377 Traditional Rental Income: $3288 Airbnb ROI: -0.49% Traditional ROI: -0.68%
3429 REGAL CREST DRIVE Longwood, FL Under contract-accepting backup offers. Timeless Elegance Meets Modern Luxury in the area'...	3 beds \| 3 baths \| 3,107 sq.ft.	$995,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 1.03% Airbnb Rental Income: $3221 Traditional Rental Income: $2979 Airbnb ROI: 0.51% Traditional ROI: 1.03%
170 CLYDE AVENUE Longwood, FL This beautifully renovated 3-bedroom, 2-bath home features fresh interior and exterior pai...	3 beds \| 2 baths \| 1,658 sq.ft.	$404,900	Airbnb cash on cash: 5.12% Traditional cash on cash: 5.04% Airbnb Rental Income: $3221 Traditional Rental Income: $2465 Airbnb ROI: 5.12% Traditional ROI: 5.04%
635 CAMBRIDGE COURT Longwood, FL Under contract-accepting backup offers. Your Dream Home Awaits! Owner Financing Opportunit...	4 beds \| 2 baths \| 1,938 sq.ft.	$479,000	Airbnb cash on cash: 6.98% Traditional cash on cash: 3.78% Airbnb Rental Income: $5377 Traditional Rental Income: $2856 Airbnb ROI: 6.98% Traditional ROI: 3.78%
105 SMOKERISE BOULEVARD Longwood, FL Under contract-accepting backup offers. Discover one of Sweetwater Oaks most impressive re...	5 beds \| 4 baths \| 4,618 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.79% Airbnb Rental Income: $null Traditional Rental Income: $4788 Airbnb ROI: N/A Traditional ROI: 3.79%
1221 ARDEN STREET Longwood, FL Under contract-accepting backup offers. WOWSA! Pool homes with this kind of layout, amenit...	3 beds \| 2 baths \| 1,525 sq.ft.	$448,875	Airbnb cash on cash: 4.31% Traditional cash on cash: 4.03% Airbnb Rental Income: $3221 Traditional Rental Income: $2374 Airbnb ROI: 4.31% Traditional ROI: 4.03%
492 TIMBER RIDGE DRIVE Longwood, FL Under contract-accepting backup offers. Welcome to this stunning pool home in the highly s...	4 beds \| 4 baths \| 3,176 sq.ft.	$810,000	Airbnb cash on cash: 3.86% Traditional cash on cash: 4.03% Airbnb Rental Income: $5377 Traditional Rental Income: $4422 Airbnb ROI: 3.86% Traditional ROI: 4.03%
290 QUEENSBERRY COURT Longwood, FL NEW ROOF (see new ext pictures). Beautifully remodeled 3-bedroom, 2-bath home perfectly si...	3 beds \| 2 baths \| 2,066 sq.ft.	$499,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.72% Airbnb Rental Income: $3221 Traditional Rental Income: $2486 Airbnb ROI: 3.74% Traditional ROI: 3.72%
495 HOWARD AVENUE Longwood, FL Welcome to your dream home! This stunning 4-bedroom, 2-bathroom residence has been complet...	4 beds \| 2 baths \| 1,855 sq.ft.	$424,999	Airbnb cash on cash: 8.98% Traditional cash on cash: 4.54% Airbnb Rental Income: $5377 Traditional Rental Income: $2527 Airbnb ROI: 8.98% Traditional ROI: 4.54%
204 ADAIR AVENUE Longwood, FL REDUCED FOR QUICK SALE! Charming 4 bedroom, 3 bathroom remodeled POOL home with a screened...	4 beds \| 3 baths \| 2,606 sq.ft.	$624,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 5.06% Airbnb Rental Income: $5377 Traditional Rental Income: $3666 Airbnb ROI: 6.13% Traditional ROI: 5.06%
3220 OAKMONT TERRACE Longwood, FL Under contract-accepting backup offers. Welcome to this beautifully maintained home in the...	4 beds \| 4 baths \| 3,121 sq.ft.	$998,000	Airbnb cash on cash: 2.42% Traditional cash on cash: 2.44% Airbnb Rental Income: $5377 Traditional Rental Income: $4313 Airbnb ROI: 2.42% Traditional ROI: 2.44%
140 W YORK COURT Longwood, FL One or more photo(s) has been virtually staged. Welcome to a home that feels like it was w...	4 beds \| 3 baths \| 2,047 sq.ft.	$469,000	Airbnb cash on cash: 8.12% Traditional cash on cash: 5.48% Airbnb Rental Income: $5377 Traditional Rental Income: $3135 Airbnb ROI: 8.12% Traditional ROI: 5.48%
1823 NORTH STREET Longwood, FL Under contract-accepting backup offers. Your search ends here with this exceptional, one-o...	3 beds \| 2 baths \| 1,650 sq.ft.	$399,900	Airbnb cash on cash: 4.97% Traditional cash on cash: 4.33% Airbnb Rental Income: $3221 Traditional Rental Income: $2255 Airbnb ROI: 4.97% Traditional ROI: 4.33%
665 E CHURCH AVENUE Longwood, FL Excellent for first time home buyers. Cozy renovated 3 Bedroom 1 Bath Home in Longwood nea...	3 beds \| 1 baths \| 836 sq.ft.	$244,000	Airbnb cash on cash: 8.73% Traditional cash on cash: 4.7% Airbnb Rental Income: $3221 Traditional Rental Income: $1565 Airbnb ROI: 8.73% Traditional ROI: 4.7%

Your search for investment property begins and ends here

Single Family Homes for Sale in Longwood, FL

3235 WINDING PINE TRAIL

Longwood, FL

4 beds | 6 baths | 4,262 sq.ft.

$1,350,000

Airbnb cash on cash: 1.18%

Traditional cash on cash: 3.96%

Airbnb Rental Income: $5377

Traditional Rental Income: $7787

Airbnb ROI: 1.18%

Traditional ROI: 3.96%

899 LORMANN CIRCLE

Longwood, FL

3 beds | 2 baths | 969 sq.ft.

$299,490

Airbnb cash on cash: 7.12%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $3221

Traditional Rental Income: $1803

Airbnb ROI: 7.12%

Traditional ROI: 4.66%

364 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,428 sq.ft.

$370,000

Airbnb cash on cash: 5.33%

Traditional cash on cash: 4.26%

Airbnb Rental Income: $3221

Traditional Rental Income: $2122

Airbnb ROI: 5.33%

Traditional ROI: 4.26%

153 Duncan Trl

Longwood, FL

3 beds | 2 baths | 2,596 sq.ft.

$539,900

Airbnb cash on cash: 3.38%

Traditional cash on cash: 3.57%

Airbnb Rental Income: $3221

Traditional Rental Income: $2588

Airbnb ROI: 3.38%

Traditional ROI: 3.57%

449 SPRINGWOOD COURT

Longwood, FL

3 beds | 2 baths | 1,075 sq.ft.

$317,500

Airbnb cash on cash: 5.99%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $3221

Traditional Rental Income: $1834

Airbnb ROI: 5.99%

Traditional ROI: 3.78%

162 DUNCAN TRAIL

Longwood, FL

4 beds | 2 baths | 1,907 sq.ft.

$450,000

Airbnb cash on cash: 8.09%

Traditional cash on cash: 3.76%

Airbnb Rental Income: $5377

Traditional Rental Income: $2468

Airbnb ROI: 8.09%

Traditional ROI: 3.76%

230 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,173 sq.ft.

$262,000

Airbnb cash on cash: 7.54%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $3221

Traditional Rental Income: $1973

Airbnb ROI: 7.54%

Traditional ROI: 5.43%

731 CRESTBROOK LOOP

Longwood, FL

3 beds | 3 baths | 2,140 sq.ft.

$405,000

Airbnb cash on cash: 4.26%

Traditional cash on cash: 6.05%

Airbnb Rental Income: $3221

Traditional Rental Income: $3173

Airbnb ROI: 4.26%