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 92 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: 5.82% Airbnb Rental Income: $3221 Traditional Rental Income: $2129 Airbnb ROI: 7.12% Traditional ROI: 5.82%
1870 CROWLEY CIRCLE E Longwood, FL Short Sale. Welcome to your peacefull oasis located on a full acre. Spacious floor plan wi...	4 beds \| 4 baths \| 3,258 sq.ft.	$625,000	Airbnb cash on cash: 4.76% Traditional cash on cash: 5.32% Airbnb Rental Income: $5377 Traditional Rental Income: $4618 Airbnb ROI: 4.76% Traditional ROI: 5.32%
2522 THICKET RIDGE COURT Longwood, FL Under contract-accepting backup offers. One or more photo(s) was virtually staged. Low-m...	3 beds \| 2 baths \| 1,842 sq.ft.	$399,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 3.88% Airbnb Rental Income: $3221 Traditional Rental Income: $2276 Airbnb ROI: 4.46% Traditional ROI: 3.88%
413 WILLOWBROOK LANE Longwood, FL Welcome home to this spacious 4-bedroom, 2-bath pool residence with dedicated office, nest...	4 beds \| 2 baths \| 2,740 sq.ft.	$582,999	Airbnb cash on cash: 5.91% Traditional cash on cash: 3.66% Airbnb Rental Income: $5377 Traditional Rental Income: $3066 Airbnb ROI: 5.91% Traditional ROI: 3.66%
308 SMOKERISE BOULEVARD Longwood, FL Welcome to 308 Smokerise Blvd., tucked away on a quiet corner lot within a cul-de-sac in t...	4 beds \| 2 baths \| 2,352 sq.ft.	$650,000	Airbnb cash on cash: 4.87% Traditional cash on cash: 2.68% Airbnb Rental Income: $5377 Traditional Rental Income: $2959 Airbnb ROI: 4.87% Traditional ROI: 2.68%
255 E HORNBEAM DRIVE Longwood, FL Under contract-accepting backup offers. Welcome to this exquisitely remodeled residence in...	4 beds \| 3 baths \| 2,309 sq.ft.	$632,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 3.19% Airbnb Rental Income: $5377 Traditional Rental Income: $3253 Airbnb ROI: 4.95% Traditional ROI: 3.19%
385 BRASSIE DRIVE Longwood, FL Under contract-accepting backup offers. Once in a life time opportunity to own this amazin...	4 beds \| 4 baths \| 3,412 sq.ft.	$660,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 4.84% Airbnb Rental Income: $5377 Traditional Rental Income: $4320 Airbnb ROI: 4.79% Traditional ROI: 4.84%
860 Charlotte St. Longwood, FL 4-Bed / 3.5-Bath Home Built in 2006. -needs updating, new ac.	4 beds \| 4 baths \| N/A	$449,000	Airbnb cash on cash: 7.55% Traditional cash on cash: 5.25% Airbnb Rental Income: $5377 Traditional Rental Income: $3324 Airbnb ROI: 7.55% Traditional ROI: 5.25%
1025 BUCKSAW PLACE Longwood, FL Short Sale. Short Sale â Opportunity awaits! This home has been winterized and is ready ...	3 beds \| 3 baths \| 2,289 sq.ft.	$419,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 2.23% Airbnb Rental Income: $3221 Traditional Rental Income: $2039 Airbnb ROI: 3.4% Traditional ROI: 2.23%
105 KILKENNY COURT Longwood, FL Welcome to 105 Kilkenny Ct and this beautifully updated Wekiva home nestled on a quiet cul...	3 beds \| 2 baths \| 1,562 sq.ft.	$435,000	Airbnb cash on cash: 3.91% Traditional cash on cash: 3.49% Airbnb Rental Income: $3221 Traditional Rental Income: $2325 Airbnb ROI: 3.91% Traditional ROI: 3.49%
1386 S RIDGE LAKE CIRCLE Longwood, FL RARE FIND in the sought out Longwood community of Northridge. This show stopping POOL HOME...	4 beds \| 2 baths \| 2,263 sq.ft.	$535,000	Airbnb cash on cash: 6.23% Traditional cash on cash: 4.36% Airbnb Rental Income: $5377 Traditional Rental Income: $3354 Airbnb ROI: 6.23% Traditional ROI: 4.36%
126 SANDALWOOD WAY Longwood, FL **This house comes with a REDUCED RATE through the seller's preferred lender. This is a le...	3 beds \| 2 baths \| 1,354 sq.ft.	$404,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 2.61% Airbnb Rental Income: $3221 Traditional Rental Income: $1945 Airbnb ROI: 4.06% Traditional ROI: 2.61%
150 ESSEX DRIVE Longwood, FL Under contract-accepting backup offers. Step into the warmth and charm of this rare cabin-...	3 beds \| 2 baths \| 1,449 sq.ft.	$432,000	Airbnb cash on cash: 3.89% Traditional cash on cash: 4.43% Airbnb Rental Income: $3221 Traditional Rental Income: $2714 Airbnb ROI: 3.89% Traditional ROI: 4.43%
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: 4.08% Airbnb Rental Income: $5377 Traditional Rental Income: $7838 Airbnb ROI: 1.35% Traditional ROI: 4.08%
2010 E TRIANGLE DRIVE Longwood, FL Under contract-accepting backup offers. IMPORTANT NOTE: Current Flood insurance policy and...	3 beds \| 2 baths \| 1,684 sq.ft.	$339,800	Airbnb cash on cash: 5.54% Traditional cash on cash: 5.6% Airbnb Rental Income: $3221 Traditional Rental Income: $2513 Airbnb ROI: 5.54% Traditional ROI: 5.6%
990 BURLWOOD COURT Longwood, FL Under contract-accepting backup offers. ***Buyer home sale contingency fell through. Prope...	5 beds \| 4 baths \| 3,184 sq.ft.	$749,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.23% Airbnb Rental Income: $null Traditional Rental Income: $4258 Airbnb ROI: N/A Traditional ROI: 4.23%
410 GEORGIA AVENUE Longwood, FL Under contract-accepting backup offers. This fully renovated home blends style and functio...	3 beds \| 2 baths \| 1,588 sq.ft.	$435,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 3.06% Airbnb Rental Income: $3221 Traditional Rental Income: $2160 Airbnb ROI: 3.88% Traditional ROI: 3.06%
450 LONGMEADOW LANE Longwood, FL Excellent opportunity in Sabal Point. POOL house with two NEW HVACs. 4 bedrooms, 3.5 bathr...	4 beds \| 4 baths \| 2,623 sq.ft.	$559,000	Airbnb cash on cash: 6.27% Traditional cash on cash: 5.75% Airbnb Rental Income: $5377 Traditional Rental Income: $4020 Airbnb ROI: 6.27% Traditional ROI: 5.75%
1310 RIDGE ROAD Longwood, FL Welcome to your own private oasis in the highly desirable Longwood area! This beautifully ...	3 beds \| 2 baths \| 1,520 sq.ft.	$485,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 2.96% Airbnb Rental Income: $3221 Traditional Rental Income: $2309 Airbnb ROI: 3.37% Traditional ROI: 2.96%
803 SWEETWATER CLUB BOULEVARD Longwood, FL One or more photo(s) has been virtually staged. In the heart of the coveted, gated Sweetwa...	4 beds \| 6 baths \| 5,344 sq.ft.	$1,575,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.07% Airbnb Rental Income: $5377 Traditional Rental Income: $7733 Airbnb ROI: 0.72% Traditional ROI: 3.07%
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.	$499,900	Airbnb cash on cash: 3.68% Traditional cash on cash: 4.06% Airbnb Rental Income: $3221 Traditional Rental Income: $2674 Airbnb ROI: 3.68% Traditional ROI: 4.06%
112 DES PINAR LANE Longwood, FL Under contract-accepting backup offers. Fully Remodeled Luxury Pool Home \| No HOA \| Priced...	4 beds \| 2 baths \| 1,604 sq.ft.	$419,000	Airbnb cash on cash: 8.65% Traditional cash on cash: 4.25% Airbnb Rental Income: $5377 Traditional Rental Income: $2566 Airbnb ROI: 8.65% Traditional ROI: 4.25%
307 COBLE DRIVE Longwood, FL Welcome to 307 Coble Drive, a thoughtfully updated 4-bedroom, 2-bath residence in the desi...	4 beds \| 2 baths \| 1,987 sq.ft.	$475,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 3.62% Airbnb Rental Income: $5377 Traditional Rental Income: $2706 Airbnb ROI: 7.19% Traditional ROI: 3.62%
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: -0.64% Airbnb Rental Income: $5377 Traditional Rental Income: $3475 Airbnb ROI: -0.49% Traditional ROI: -0.64%
290 QUEENSBERRY COURT Longwood, FL Under contract-accepting backup offers. SELLER WILL PAY A PORTION OF BUYER'S CLOSING COSTS...	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 Under contract-accepting backup offers. Welcome to your dream home! This stunning 4-bedroo...	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%
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.	$792,000	Airbnb cash on cash: 3.8% Traditional cash on cash: 2.89% Airbnb Rental Income: $5377 Traditional Rental Income: $3619 Airbnb ROI: 3.8% Traditional ROI: 2.89%
140 W YORK COURT Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 3 baths \| 2,047 sq.ft.	$454,000	Airbnb cash on cash: 8.41% Traditional cash on cash: 5.98% Airbnb Rental Income: $5377 Traditional Rental Income: $3259 Airbnb ROI: 8.41% Traditional ROI: 5.98%
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%
700 LAKESIDE PLACE Longwood, FL Beautifully renovated home in the heart of Longwood, just steps to Reiter Park. This move-...	3 beds \| 2 baths \| 1,279 sq.ft.	$375,000	Airbnb cash on cash: 4.22% Traditional cash on cash: 2.82% Airbnb Rental Income: $3221 Traditional Rental Income: $2002 Airbnb ROI: 4.22% Traditional ROI: 2.82%
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: 3.04% Airbnb Rental Income: $5377 Traditional Rental Income: $3559 Airbnb ROI: 4.03% Traditional ROI: 3.04%
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: 2.54% Airbnb Rental Income: $null Traditional Rental Income: $10080 Airbnb ROI: N/A Traditional ROI: 2.54%
100 E WYNDHAM COURT Longwood, FL Welcome to this spacious 4-bedroom, 2-bath home located just three streets from Top-Rated ...	4 beds \| 2 baths \| 1,695 sq.ft.	$395,000	Airbnb cash on cash: 9.09% Traditional cash on cash: 3.86% Airbnb Rental Income: $5377 Traditional Rental Income: $2357 Airbnb ROI: 9.09% Traditional ROI: 3.86%
1841 NORTH STREET Longwood, FL Super cute 3/2 single family home, 2 minutes to the Altamonte Mall, across the street from...	3 beds \| 2 baths \| 1,025 sq.ft.	$295,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 5.2% Airbnb Rental Income: $3221 Traditional Rental Income: $2060 Airbnb ROI: 6.76% Traditional ROI: 5.2%
478 WILD OAK CIRCLE Longwood, FL Under contract-accepting backup offers. Welcome to 478 Wild Oak Circle, where life extends...	4 beds \| 2 baths \| 2,574 sq.ft.	$779,000	Airbnb cash on cash: 4.08% Traditional cash on cash: 2.85% Airbnb Rental Income: $5377 Traditional Rental Income: $3393 Airbnb ROI: 4.08% Traditional ROI: 2.85%
224 SPRINGSIDE ROAD Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Th...	3 beds \| 2 baths \| 1,653 sq.ft.	$459,000	Airbnb cash on cash: 3.02% Traditional cash on cash: 3.4% Airbnb Rental Income: $3221 Traditional Rental Income: $2661 Airbnb ROI: 3.02% Traditional ROI: 3.4%
668 GEORGIA AVENUE Longwood, FL One or more photo(s) has been virtually staged. Beautifully Updated Longwood Home with No ...	3 beds \| 2 baths \| 1,700 sq.ft.	$349,900	Airbnb cash on cash: 5.68% Traditional cash on cash: 5.93% Airbnb Rental Income: $3221 Traditional Rental Income: $2576 Airbnb ROI: 5.68% Traditional ROI: 5.93%
341 FERDINAND DRIVE Longwood, FL Welcome to Columbus Harbour and this charming 3-bedroom, 2-bathroom home offering 1,667 sf...	3 beds \| 2 baths \| 1,667 sq.ft.	$419,900	Airbnb cash on cash: 3.96% Traditional cash on cash: 4% Airbnb Rental Income: $3221 Traditional Rental Income: $2510 Airbnb ROI: 3.96% Traditional ROI: 4%
204 BLUE LAKE DRIVE Longwood, FL One or more photo(s) has been virtually staged. This 4 bedroom, 3.5 bathroom pool home is ...	4 beds \| 4 baths \| 2,914 sq.ft.	$729,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 5.59% Airbnb Rental Income: $5377 Traditional Rental Income: $4931 Airbnb ROI: 4.65% Traditional ROI: 5.59%

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: 5.82%

Airbnb Rental Income: $3221

Traditional Rental Income: $2129

Airbnb ROI: 7.12%

Traditional ROI: 5.82%

1870 CROWLEY CIRCLE E

Longwood, FL

4 beds | 4 baths | 3,258 sq.ft.

$625,000

Airbnb cash on cash: 4.76%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $5377

Traditional Rental Income: $4618

Airbnb ROI: 4.76%

Traditional ROI: 5.32%

2522 THICKET RIDGE COURT

Longwood, FL

3 beds | 2 baths | 1,842 sq.ft.

$399,000

Airbnb cash on cash: 4.46%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $3221

Traditional Rental Income: $2276

Airbnb ROI: 4.46%

Traditional ROI: 3.88%

413 WILLOWBROOK LANE

Longwood, FL

4 beds | 2 baths | 2,740 sq.ft.

$582,999

Airbnb cash on cash: 5.91%

Traditional cash on cash: 3.66%

Airbnb Rental Income: $5377

Traditional Rental Income: $3066

Airbnb ROI: 5.91%

Traditional ROI: 3.66%

308 SMOKERISE BOULEVARD

Longwood, FL

4 beds | 2 baths | 2,352 sq.ft.

$650,000

Airbnb cash on cash: 4.87%

Traditional cash on cash: 2.68%

Airbnb Rental Income: $5377

Traditional Rental Income: $2959

Airbnb ROI: 4.87%

Traditional ROI: 2.68%

255 E HORNBEAM DRIVE

Longwood, FL

4 beds | 3 baths | 2,309 sq.ft.

$632,000

Airbnb cash on cash: 4.95%

Traditional cash on cash: 3.19%

Airbnb Rental Income: $5377

Traditional Rental Income: $3253

Airbnb ROI: 4.95%

Traditional ROI: 3.19%

385 BRASSIE DRIVE

Longwood, FL

4 beds | 4 baths | 3,412 sq.ft.

$660,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 4.84%

Airbnb Rental Income: $5377

Traditional Rental Income: $4320

Airbnb ROI: 4.79%

Traditional ROI: 4.84%

860 Charlotte St.

Longwood, FL

4 beds | 4 baths | N/A

$449,000

Airbnb cash on cash: 7.55%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $5377

Traditional Rental Income: $3324

Airbnb ROI: 7.55%