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 Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Longwood, FL

Search for Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Longwood, Florida. Browse all of Mashvisor’s Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 120 Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory 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
3996 RADLEY COURT #3996 Longwood, FL One or more photo(s) has been virtually staged. Do not miss this excellent opportunity to ...	2 beds \| 2 baths \| 1,427 sq.ft.	$250,000	Airbnb cash on cash: -1.68% Traditional cash on cash: 4.62% Airbnb Rental Income: $1115 Traditional Rental Income: $2228 Airbnb ROI: -1.68% Traditional ROI: 4.62%
4102 CLUBSIDE DRIVE #4102 Longwood, FL Spacious 2-Bedroom Corner Unit in Clubside at Sabal Point â Private, Updated & Move-In R...	2 beds \| 3 baths \| 1,380 sq.ft.	$222,000	Airbnb cash on cash: -1.38% Traditional cash on cash: 4.12% Airbnb Rental Income: $1115 Traditional Rental Income: $1897 Airbnb ROI: -1.38% Traditional ROI: 4.12%
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%
568 TALL OAKS TERRACE Longwood, FL Under contract-accepting backup offers. 3 bedroom + office/playroom/flex space home with a...	3 beds \| 2 baths \| 1,513 sq.ft.	$400,000	Airbnb cash on cash: 4.65% Traditional cash on cash: 3.78% Airbnb Rental Income: $3221 Traditional Rental Income: $2166 Airbnb ROI: 4.65% Traditional ROI: 3.78%
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%
561 SHINING ARMOR LANE Longwood, FL Invest with success and buy through Auction.com. This bank-owned investment property is a ...	N/A beds \| N/A baths \| N/A	$358,000	Airbnb cash on cash: 2.29% Traditional cash on cash: 2.64% Airbnb Rental Income: $2039 Traditional Rental Income: $1628 Airbnb ROI: 2.29% Traditional ROI: 2.64%
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%
202 CROWN OAKS WAY #201 Longwood, FL Discover this spacious 2-bedroom, 2-bathroom second-floor condo located in the highly desi...	2 beds \| 2 baths \| 1,119 sq.ft.	$139,900	Airbnb cash on cash: 2.63% Traditional cash on cash: 9.45% Airbnb Rental Income: $1115 Traditional Rental Income: $1656 Airbnb ROI: 2.63% Traditional ROI: 9.45%
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.	$585,000	Airbnb cash on cash: 5.88% Traditional cash on cash: 3.64% Airbnb Rental Income: $5377 Traditional Rental Income: $3066 Airbnb ROI: 5.88% Traditional ROI: 3.64%
114 JUNIPER LANE Longwood, FL One or more photo(s) has been virtually staged. Quality that speaks for itself. Pride of o...	2 beds \| 2 baths \| 2,049 sq.ft.	$460,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 3.67% Airbnb Rental Income: $1115 Traditional Rental Income: $2486 Airbnb ROI: -0.39% Traditional ROI: 3.67%
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.	$689,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 2.47% Airbnb Rental Income: $5377 Traditional Rental Income: $2959 Airbnb ROI: 4.54% Traditional ROI: 2.47%
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: 2.72% Airbnb Rental Income: $5377 Traditional Rental Income: $2976 Airbnb ROI: 4.95% Traditional ROI: 2.72%
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%
107 CEDAR POINT LANE Longwood, FL This house comes with a REDUCED RATE through the seller's preferred lender. Welcom...	3 beds \| 3 baths \| 2,360 sq.ft.	$494,900	Airbnb cash on cash: 2.77% Traditional cash on cash: 4.02% Airbnb Rental Income: $3221 Traditional Rental Income: $3074 Airbnb ROI: 2.77% Traditional ROI: 4.02%
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%
572 LAKE WILDMERE COVE Longwood, FL Here is your opportunity to own a true Turn Key Investment property.This almost new townho...	4 beds \| 5 baths \| 2,294 sq.ft.	$455,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 3.97% Airbnb Rental Income: $5377 Traditional Rental Income: $3196 Airbnb ROI: 6.54% Traditional ROI: 3.97%
486 N PIN OAK PLACE #112 Longwood, FL One or more photo(s) has been virtually staged. **Seller may consider buyer concessions if...	2 beds \| 1 baths \| 959 sq.ft.	$189,900	Airbnb cash on cash: 1.41% Traditional cash on cash: 5.1% Airbnb Rental Income: $1115 Traditional Rental Income: $1406 Airbnb ROI: 1.41% Traditional ROI: 5.1%
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.	$575,000	Airbnb cash on cash: 6.07% Traditional cash on cash: 5.57% Airbnb Rental Income: $5377 Traditional Rental Income: $4020 Airbnb ROI: 6.07% Traditional ROI: 5.57%
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 \| 5,144 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.	$525,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 3.82% Airbnb Rental Income: $3221 Traditional Rental Income: $2674 Airbnb ROI: 3.45% Traditional ROI: 3.82%
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%
116 WILD HOLLY LANE Longwood, FL Short Sale. This townhome offers incredible potential, featuring a versatile separate offi...	2 beds \| 2 baths \| 1,722 sq.ft.	$245,000	Airbnb cash on cash: 0.65% Traditional cash on cash: 7.51% Airbnb Rental Income: $1115 Traditional Rental Income: $2329 Airbnb ROI: 0.65% Traditional ROI: 7.51%
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%
420 SUMMIT RIDGE PLACE #200 Longwood, FL **This property qualifies for a closing cost credit up to $3,700 through the Sellerâs pr...	3 beds \| 2 baths \| 1,586 sq.ft.	$229,000	Airbnb cash on cash: 5.88% Traditional cash on cash: 5.02% Airbnb Rental Income: $3221 Traditional Rental Income: $2308 Airbnb ROI: 5.88% Traditional ROI: 5.02%
190 W SABAL PALM PLACE #190 Longwood, FL One or more photo(s) has been virtually staged. Lovely end-unit home is situated in the Sa...	2 beds \| 2 baths \| 1,191 sq.ft.	$214,900	Airbnb cash on cash: -1.85% Traditional cash on cash: 2.98% Airbnb Rental Income: $1115 Traditional Rental Income: $1724 Airbnb ROI: -1.85% Traditional ROI: 2.98%
2745 Night Hawk Ct. Longwood, FL Don't miss out on this opportunity to own a 3 bedroom, 2 bath townhouse in Shadowbay Club....	3 beds \| 2 baths \| 1,396 sq.ft.	$340,000	Airbnb cash on cash: 5.34% Traditional cash on cash: 4.91% Airbnb Rental Income: $3221 Traditional Rental Income: $2359 Airbnb ROI: 5.34% Traditional ROI: 4.91%
895 Pasadena Ave. Longwood, FL Unique Large Duplex, 1 unit faces Highland St and 1 unit faces Pasadena Ave,Large Corner L...	6 beds \| 4 baths \| 2,632 sq.ft.	$510,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.32% Airbnb Rental Income: $null Traditional Rental Income: $3466 Airbnb ROI: N/A Traditional ROI: 5.32%
1816 COVENT GARDEN LANE Longwood, FL Under contract-accepting backup offers. Gated Community! Outstanding 2 Bedroom/2.5 Baths. ...	2 beds \| 3 baths \| 1,284 sq.ft.	$287,000	Airbnb cash on cash: 0.15% Traditional cash on cash: 4.79% Airbnb Rental Income: $1115 Traditional Rental Income: $1995 Airbnb ROI: 0.15% Traditional ROI: 4.79%
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%

Your search for investment property begins and ends here

Single Family Residential For Salhttf L For Salhttf L For Salhttf L For Salhttf L Fory Residential for Sale in Longwood, FL

3996 RADLEY COURT #3996

Longwood, FL

2 beds | 2 baths | 1,427 sq.ft.

$250,000

Airbnb cash on cash: -1.68%

Traditional cash on cash: 4.62%

Airbnb Rental Income: $1115

Traditional Rental Income: $2228

Airbnb ROI: -1.68%

Traditional ROI: 4.62%

4102 CLUBSIDE DRIVE #4102

Longwood, FL

2 beds | 3 baths | 1,380 sq.ft.

$222,000

Airbnb cash on cash: -1.38%

Traditional cash on cash: 4.12%

Airbnb Rental Income: $1115

Traditional Rental Income: $1897

Airbnb ROI: -1.38%

Traditional ROI: 4.12%

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%

568 TALL OAKS TERRACE

Longwood, FL

3 beds | 2 baths | 1,513 sq.ft.

$400,000

Airbnb cash on cash: 4.65%

Traditional cash on cash: 3.78%

Airbnb Rental Income: $3221

Traditional Rental Income: $2166

Airbnb ROI: 4.65%

Traditional ROI: 3.78%

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%

561 SHINING ARMOR LANE

Longwood, FL

N/A beds | N/A baths | N/A

$358,000

Airbnb cash on cash: 2.29%

Traditional cash on cash: 2.64%

Airbnb Rental Income: $2039

Traditional Rental Income: $1628

Airbnb ROI: 2.29%

Traditional ROI: 2.64%

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%

202 CROWN OAKS WAY #201

Longwood, FL

2 beds | 2 baths | 1,119 sq.ft.

$139,900

Airbnb cash on cash: 2.63%

Traditional cash on cash: 9.45%

Airbnb Rental Income: $1115

Traditional Rental Income: $1656

Airbnb ROI: 2.63%