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 90 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.	$1,400,000	Airbnb cash on cash: 1.1% Traditional cash on cash: 3.79% Airbnb Rental Income: $5377 Traditional Rental Income: $7787 Airbnb ROI: 1.1% Traditional ROI: 3.79%
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.	$289,990	Airbnb cash on cash: 7.38% Traditional cash on cash: 4.84% Airbnb Rental Income: $3221 Traditional Rental Income: $1803 Airbnb ROI: 7.38% Traditional ROI: 4.84%
199 E MARVIN AVENUE Longwood, FL Under contract-accepting backup offers. Come see this spacious, updated First time Homebuy...	3 beds \| 1 baths \| 967 sq.ft.	$265,000	Airbnb cash on cash: 7.76% Traditional cash on cash: 4.53% Airbnb Rental Income: $3221 Traditional Rental Income: $1686 Airbnb ROI: 7.76% Traditional ROI: 4.53%
2681 AZALEA DRIVE Longwood, FL A Home to Be Thankful For â $10,000 in Buyer Savings! As the season turns and the air...	3 beds \| 2 baths \| 1,399 sq.ft.	$365,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 3.48% Airbnb Rental Income: $3221 Traditional Rental Income: $1994 Airbnb ROI: 4.94% Traditional ROI: 3.48%
364 HOWARD BOULEVARD Longwood, FL Welcome to this charming 3-bedroom, 2-bath home tucked away at the end of a quiet dead-end...	3 beds \| 2 baths \| 1,400 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%
310 VISTA OAK DRIVE Longwood, FL ~MOTIVATED SELLER~ Welcome to your dream home in the highly sought-after gated community...	4 beds \| 5 baths \| 3,286 sq.ft.	$999,500	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.64% Airbnb Rental Income: $5377 Traditional Rental Income: $5513 Airbnb ROI: 2.33% Traditional ROI: 3.64%
1530 ARDEN STREET Longwood, FL Under contract-accepting backup offers. Fall in love with this beautifully updated 4-bedro...	4 beds \| 2 baths \| 1,840 sq.ft.	$399,000	Airbnb cash on cash: 9.45% Traditional cash on cash: 4.79% Airbnb Rental Income: $5377 Traditional Rental Income: $2551 Airbnb ROI: 9.45% Traditional ROI: 4.79%
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 This beautifully updated three-bedroom, two-bath home in Longwood offers 1,075 square feet...	3 beds \| 2 baths \| 1,075 sq.ft.	$325,000	Airbnb cash on cash: 5.83% Traditional cash on cash: 3.67% Airbnb Rental Income: $3221 Traditional Rental Income: $1834 Airbnb ROI: 5.83% Traditional ROI: 3.67%
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%
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%
104 N SILVER CLUSTER COURT Longwood, FL Under contract-accepting backup offers. Seller may consider buyer concessions if made in a...	3 beds \| 2 baths \| 1,386 sq.ft.	$395,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.41% Airbnb Rental Income: $3221 Traditional Rental Income: $2089 Airbnb ROI: 4.51% Traditional ROI: 3.41%
2040 E TRIANGLE DRIVE Longwood, FL NEW PRICE REDUCTION! Now priced below market value. Charming, Updated 3-Bedroom Home ...	3 beds \| 2 baths \| 1,283 sq.ft.	$345,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 3.62% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.42% Traditional ROI: 3.62%
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 Your new pool home in the desirable Wekiva Hills community is waiting for you. This 4 bedr...	4 beds \| 2 baths \| 2,720 sq.ft.	$470,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 5.97% Airbnb Rental Income: $5377 Traditional Rental Income: $3220 Airbnb ROI: 8.41% Traditional ROI: 5.97%
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.	$440,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 3.08% Airbnb Rental Income: $3221 Traditional Rental Income: $2199 Airbnb ROI: 3.8% Traditional ROI: 3.08%
501 RIVERBEND BOULEVARD Longwood, FL Are you ready to finally add the most important key to your keychain? After scrolling for...	4 beds \| 2 baths \| 2,559 sq.ft.	$599,900	Airbnb cash on cash: 5.23% Traditional cash on cash: 2.61% Airbnb Rental Income: $5377 Traditional Rental Income: $2824 Airbnb ROI: 5.23% Traditional ROI: 2.61%
448 VILLAGE VIEW LANE Longwood, FL Step inside this beautifully upgraded Sabal Point home, where classic character meets mode...	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%
966 N RONALD REAGAN BOULEVARD Longwood, FL HIGH AND DRY! Located just 1/2 mile from the Longwood SunRail Station. Donât miss your o...	5 beds \| 3 baths \| 2,490 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3535 Airbnb ROI: N/A Traditional ROI: 4.32%
674 PINE SHADOW COURT Longwood, FL Discover this beautifully maintained 4-bedroom, 3-bath home in the sought-after Sabal Poin...	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%
917 BRANTLEY DRIVE Longwood, FL Under contract-accepting backup offers. Beautifully updated 4-bedroom, 2.5-bath home in on...	4 beds \| 3 baths \| 2,413 sq.ft.	$500,000	Airbnb cash on cash: 7.07% Traditional cash on cash: 4.26% Airbnb Rental Income: $5377 Traditional Rental Income: $2976 Airbnb ROI: 7.07% Traditional ROI: 4.26%
851 N WAYMAN STREET Longwood, FL Welcome to this beautifully updated Longwood pool home full of charm, warmth, and timeless...	3 beds \| 2 baths \| 1,353 sq.ft.	$362,500	Airbnb cash on cash: 5.83% Traditional cash on cash: 4.85% Airbnb Rental Income: $3221 Traditional Rental Income: $2160 Airbnb ROI: 5.83% Traditional ROI: 4.85%
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%
115 FOREST POINT LANE Longwood, FL Under contract-accepting backup offers. Welcome to 115 Forest Point Lane â a beautifully...	4 beds \| 3 baths \| 2,689 sq.ft.	$875,000	Airbnb cash on cash: 3.65% Traditional cash on cash: 2.61% Airbnb Rental Income: $5377 Traditional Rental Income: $3443 Airbnb ROI: 3.65% Traditional ROI: 2.61%
328 ISLAND SOUND COURT Longwood, FL Welcome to this stunning 5-bedroom, 4-bathroom energy-efficient Pulte home located in a de...	5 beds \| 4 baths \| 3,715 sq.ft.	$1,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.15% Airbnb Rental Income: $null Traditional Rental Income: $4310 Airbnb ROI: N/A Traditional ROI: 2.15%
1510 PELICAN STREET Longwood, FL 3-bed, 2-bath residence nestled on a serene, tree-lined street in one of Longwoodâs DESI...	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 Welcome to this charming and spacious home tucked away in the sought-after Sanlando Spring...	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.	$410,000	Airbnb cash on cash: 4.82% Traditional cash on cash: 4.81% Airbnb Rental Income: $3221 Traditional Rental Income: $2491 Airbnb ROI: 4.82% Traditional ROI: 4.81%
821 SUTTER LOOP Longwood, FL Under contract-accepting backup offers. NEW PRICE IMPROVEMENT SEPT 19!, NEW ROOF April 202...	4 beds \| 2 baths \| 2,074 sq.ft.	$430,000	Airbnb cash on cash: 8.82% Traditional cash on cash: 4.75% Airbnb Rental Income: $5377 Traditional Rental Income: $2655 Airbnb ROI: 8.82% Traditional ROI: 4.75%
554 ESTATES PLACE Longwood, FL Welcome to the Estates at Springs Landings! If you are looking for the perfect blend of lu...	5 beds \| 3 baths \| 3,308 sq.ft.	$1,050,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.87% Airbnb Rental Income: $null Traditional Rental Income: $3745 Airbnb ROI: N/A Traditional ROI: 1.87%
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.	$399,000	Airbnb cash on cash: 4.1% Traditional cash on cash: 4.66% Airbnb Rental Income: $3221 Traditional Rental Income: $2704 Airbnb ROI: 4.1% Traditional ROI: 4.66%
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%
287 HILLTOP DRIVE Longwood, FL Under contract-accepting backup offers. Convenience, Land, Nature, Energy Efficiency. Keep...	4 beds \| 3 baths \| 2,522 sq.ft.	$575,000	Airbnb cash on cash: 6.32% Traditional cash on cash: 3.5% Airbnb Rental Income: $5377 Traditional Rental Income: $2780 Airbnb ROI: 6.32% Traditional ROI: 3.5%
3429 REGAL CREST DRIVE Longwood, FL Timeless Elegance Meets Modern Luxury in the area's premier golf course community of Alaqu...	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%
1351 N CLASSIC COURT Longwood, FL A rare opportunity to own one of the most distinguished lakefront estates on Lake Brantley...	4 beds \| 6 baths \| 4,956 sq.ft.	$2,945,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 1.69% Airbnb Rental Income: $5377 Traditional Rental Income: $8732 Airbnb ROI: 0.07% Traditional ROI: 1.69%
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.	$409,900	Airbnb cash on cash: 5.05% Traditional cash on cash: 4.97% Airbnb Rental Income: $3221 Traditional Rental Income: $2465 Airbnb ROI: 5.05% Traditional ROI: 4.97%

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.

$1,400,000

Airbnb cash on cash: 1.1%

Traditional cash on cash: 3.79%

Airbnb Rental Income: $5377

Traditional Rental Income: $7787

Airbnb ROI: 1.1%

Traditional ROI: 3.79%

899 LORMANN CIRCLE

Longwood, FL

3 beds | 2 baths | 969 sq.ft.

$289,990

Airbnb cash on cash: 7.38%

Traditional cash on cash: 4.84%

Airbnb Rental Income: $3221

Traditional Rental Income: $1803

Airbnb ROI: 7.38%

Traditional ROI: 4.84%

199 E MARVIN AVENUE

Longwood, FL

3 beds | 1 baths | 967 sq.ft.

$265,000

Airbnb cash on cash: 7.76%

Traditional cash on cash: 4.53%

Airbnb Rental Income: $3221

Traditional Rental Income: $1686

Airbnb ROI: 7.76%

Traditional ROI: 4.53%

2681 AZALEA DRIVE

Longwood, FL

3 beds | 2 baths | 1,399 sq.ft.

$365,000

Airbnb cash on cash: 4.94%

Traditional cash on cash: 3.48%

Airbnb Rental Income: $3221

Traditional Rental Income: $1994

Airbnb ROI: 4.94%

Traditional ROI: 3.48%

364 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,400 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%

310 VISTA OAK DRIVE

Longwood, FL

4 beds | 5 baths | 3,286 sq.ft.

$999,500

Airbnb cash on cash: 2.33%

Traditional cash on cash: 3.64%

Airbnb Rental Income: $5377

Traditional Rental Income: $5513

Airbnb ROI: 2.33%

Traditional ROI: 3.64%

1530 ARDEN STREET

Longwood, FL

4 beds | 2 baths | 1,840 sq.ft.

$399,000

Airbnb cash on cash: 9.45%

Traditional cash on cash: 4.79%

Airbnb Rental Income: $5377

Traditional Rental Income: $2551

Airbnb ROI: 9.45%

Traditional ROI: 4.79%

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%