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 94 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
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%
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.	$519,900	Airbnb cash on cash: 3.55% Traditional cash on cash: 3.74% Airbnb Rental Income: $3221 Traditional Rental Income: $2588 Airbnb ROI: 3.55% Traditional ROI: 3.74%
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 Under contract-accepting backup offers. Welcome to this beautifully updated 3-bedroom, 2-b...	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%
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%
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%
305 SWEETWATER CLUB CIRCLE Longwood, FL Located behind the gates of the exclusive, guard-gated Sweetwater Club Tennis Community, t...	4 beds \| 6 baths \| 4,975 sq.ft.	$1,400,000	Airbnb cash on cash: 1.35% Traditional cash on cash: 0.98% Airbnb Rental Income: $5377 Traditional Rental Income: $3815 Airbnb ROI: 1.35% Traditional ROI: 0.98%
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%
331 HUNTERS POINT COURT Longwood, FL Under contract-accepting backup offers. Enjoy peace of mind in this fully remodeled home, ...	4 beds \| 3 baths \| 2,097 sq.ft.	$460,000	Airbnb cash on cash: 8.37% Traditional cash on cash: 4.83% Airbnb Rental Income: $5377 Traditional Rental Income: $2770 Airbnb ROI: 8.37% Traditional ROI: 4.83%
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.	$545,000	Airbnb cash on cash: 6.85% Traditional cash on cash: 4.67% Airbnb Rental Income: $5377 Traditional Rental Income: $3177 Airbnb ROI: 6.85% Traditional ROI: 4.67%
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%
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%
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 Pool homes with these kind of amenities, & functionality rarely hit the market, especially...	3 beds \| 2 baths \| 1,525 sq.ft.	$448,875	Airbnb cash on cash: 4.33% Traditional cash on cash: 4.04% Airbnb Rental Income: $3221 Traditional Rental Income: $2374 Airbnb ROI: 4.33% Traditional ROI: 4.04%
290 QUEENSBERRY COURT Longwood, FL SELLER WILL PAY A PORTION OF BUYER'S CLOSING COSTS WITH ACCEPTABLE OFFER! NEW ROOF, NEW FL...	3 beds \| 2 baths \| 2,066 sq.ft.	$499,899	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.	$419,999	Airbnb cash on cash: 9.09% Traditional cash on cash: 4.61% Airbnb Rental Income: $5377 Traditional Rental Income: $2527 Airbnb ROI: 9.09% Traditional ROI: 4.61%
204 ADAIR AVENUE Longwood, FL Under contract-accepting backup offers. REDUCED FOR QUICK SALE! Charming 4 bedroom, 3 bath...	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%
112 BRANDYWINE LANE Longwood, FL Welcome to 112 Brandywine Lane, a beautifully refreshed pool home located in the highly so...	4 beds \| 3 baths \| 2,305 sq.ft.	$835,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 2.24% Airbnb Rental Income: $5377 Traditional Rental Income: $3268 Airbnb ROI: 3.56% Traditional ROI: 2.24%
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%
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%
2208 COVE COURT Longwood, FL Under contract-accepting backup offers. This stunning Lake Brantley estate combines timele...	5 beds \| 5 baths \| 3,404 sq.ft.	$1,500,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.79% Airbnb Rental Income: $null Traditional Rental Income: $6386 Airbnb ROI: N/A Traditional ROI: 2.79%
901 CUTLER ROAD Longwood, FL LOWEST PRICE HOME PER SQUARE FOOT IN A SQUARE MILE. This home is move it ready. Pull over...	3 beds \| 2 baths \| 2,226 sq.ft.	$480,000	Airbnb cash on cash: 3.04% Traditional cash on cash: 3.11% Airbnb Rental Income: $3221 Traditional Rental Income: $2528 Airbnb ROI: 3.04% Traditional ROI: 3.11%
672 MOSSY BRANCH COURT Longwood, FL Completely remodeled and move-in ready, this impressive residence at 672 Mossy Branch Ct, ...	4 beds \| 3 baths \| 3,924 sq.ft.	$799,900	Airbnb cash on cash: 4.03% Traditional cash on cash: 2.63% Airbnb Rental Income: $5377 Traditional Rental Income: $3249 Airbnb ROI: 4.03% Traditional ROI: 2.63%
921 SWEETWATER CLUB BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to an extraordinary estate blending timele...	5 beds \| 7 baths \| 7,970 sq.ft.	$3,650,000	Airbnb cash on cash: N/A Traditional cash on cash: 0.61% Airbnb Rental Income: $null Traditional Rental Income: $7960 Airbnb ROI: N/A Traditional ROI: 0.61%
757 LONGDALE AVENUE Longwood, FL Under contract-accepting backup offers. Welcome to 757 Longdale Ave this fully renovated s...	3 beds \| 2 baths \| 1,238 sq.ft.	$324,900	Airbnb cash on cash: 6.81% Traditional cash on cash: 5.16% Airbnb Rental Income: $3221 Traditional Rental Income: $1993 Airbnb ROI: 6.81% Traditional ROI: 5.16%
1126 BROWNSHIRE COURT Longwood, FL This majestic estate is a true masterpiece of elegance and timeless architecture, graceful...	5 beds \| 7 baths \| 8,100 sq.ft.	$2,598,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.63% Airbnb Rental Income: $null Traditional Rental Income: $7901 Airbnb ROI: N/A Traditional ROI: 1.63%

Your search for investment property begins and ends here

Single Family Homes for Sale in Longwood, FL

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%

153 Duncan Trl

Longwood, FL

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

$519,900

Airbnb cash on cash: 3.55%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $3221

Traditional Rental Income: $2588

Airbnb ROI: 3.55%

Traditional ROI: 3.74%

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%

Traditional ROI: 6.05%

1889 RANCHLAND TRAIL

Longwood, FL

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%

210 BANBURY COURT

Longwood, FL

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%