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.

Hackberry Investment Property for Sale in Longwood, FL

Search for Hackberry Investment Property for Sale in Longwood, Florida. Browse all of Mashvisor’s Hackberry Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 121 Hackberry Investment Property 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

Hackberry Investment Property 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%