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.

Golden Highlands Investment Property for Sale in Longwood, FL

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

Showing 144 Golden Highlands Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

separator

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.	$245,000	Airbnb cash on cash: -1.7% Traditional cash on cash: 4.98% Airbnb Rental Income: $1115 Traditional Rental Income: $2287 Airbnb ROI: -1.7% Traditional ROI: 4.98%
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: 4.46% Airbnb Rental Income: $1115 Traditional Rental Income: $1969 Airbnb ROI: -1.38% Traditional ROI: 4.46%
417 SUMMIT RIDGE PLACE #213 Longwood, FL Welcome to this beautifully updated condo located in the desirable community, Residences a...	2 beds \| 2 baths \| 1,274 sq.ft.	$239,000	Airbnb cash on cash: -1.49% Traditional cash on cash: 3.52% Airbnb Rental Income: $1115 Traditional Rental Income: $1871 Airbnb ROI: -1.49% Traditional ROI: 3.52%
1665 GRANGE CIRCLE Longwood, FL Expect to be impressed with this beautiful 3-bedroom, 2-bathroom home featuring stunning u...	3 beds \| 2 baths \| 2,189 sq.ft.	$399,000	Airbnb cash on cash: 4.28% Traditional cash on cash: 6.3% Airbnb Rental Income: $3221 Traditional Rental Income: $3251 Airbnb ROI: 4.28% Traditional ROI: 6.3%
214 SHERIDAN AVENUE Longwood, FL MULTIPLE OFFERS BEST AND FINAL DUE ON 4/25 BY 5:00PM Welcome to your next homeâw...	3 beds \| 2 baths \| 1,707 sq.ft.	$425,000	Airbnb cash on cash: 3.88% Traditional cash on cash: 3.41% Airbnb Rental Income: $3221 Traditional Rental Income: $2306 Airbnb ROI: 3.88% Traditional ROI: 3.41%
2681 AZALEA DRIVE Longwood, FL Under contract-accepting backup offers. Welcome to your springtime retreat in the desirabl...	3 beds \| 2 baths \| 1,399 sq.ft.	$345,000	Airbnb cash on cash: 5.28% Traditional cash on cash: 3.74% Airbnb Rental Income: $3221 Traditional Rental Income: $1994 Airbnb ROI: 5.28% Traditional ROI: 3.74%
420 W WEKIVA TRAIL Longwood, FL Under contract-accepting backup offers. A RARE opportunity in Wekiva awaits! Every major u...	3 beds \| 2 baths \| 1,787 sq.ft.	$448,000	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.16% Airbnb Rental Income: $3221 Traditional Rental Income: $2251 Airbnb ROI: 3.74% Traditional ROI: 3.16%
102 N SILVER CLUSTER COURT Longwood, FL Welcome to 102 Silver Cluster Ct N in Longwood, a beautifully maintained pool home under $...	3 beds \| 2 baths \| 1,166 sq.ft.	$395,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 3.07% Airbnb Rental Income: $3221 Traditional Rental Income: $1980 Airbnb ROI: 4.46% Traditional ROI: 3.07%
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: 2.75% Airbnb Rental Income: $2039 Traditional Rental Income: $1664 Airbnb ROI: 2.29% Traditional ROI: 2.75%
884 CUTLER ROAD Longwood, FL One or more photo(s) has been virtually staged. Welcome to this beautifully updated 5-bedr...	5 beds \| 3 baths \| 2,601 sq.ft.	$625,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.86% Airbnb Rental Income: $null Traditional Rental Income: $2235 Airbnb ROI: N/A Traditional ROI: 1.86%
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: 11.58% Airbnb Rental Income: $1115 Traditional Rental Income: $1941 Airbnb ROI: 2.63% Traditional ROI: 11.58%
105 DURHAM PLACE #105 Longwood, FL Discover 105 Durham Place, a 2-bedroom, 2-bathroom condo in the sought-after Wekiva commun...	2 beds \| 2 baths \| 1,427 sq.ft.	$250,000	Airbnb cash on cash: -1.69% Traditional cash on cash: 3.28% Airbnb Rental Income: $1115 Traditional Rental Income: $1914 Airbnb ROI: -1.69% Traditional ROI: 3.28%
106 HIDDEN OAK DRIVE Longwood, FL Tucked beneath a canopy of towering oaks on a quiet, tucked-away street, this 3-bedroom, 2...	3 beds \| 2 baths \| 2,127 sq.ft.	$460,000	Airbnb cash on cash: 3.42% Traditional cash on cash: 3.49% Airbnb Rental Income: $3221 Traditional Rental Income: $2525 Airbnb ROI: 3.42% Traditional ROI: 3.49%
478 SABAL TRAIL CIRCLE Longwood, FL Welcome to the desirable Sabal Point community! Located at 478 Sabal Trail Circle in Longw...	4 beds \| 3 baths \| 2,529 sq.ft.	$645,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 3.49% Airbnb Rental Income: $5377 Traditional Rental Income: $3502 Airbnb ROI: 4.8% Traditional ROI: 3.49%
105 FAIRWAY DRIVE Longwood, FL THE SPRINGS LIFESTYLE AT AN UNBEATABLE VALUE Imagine waking up in the heart of one of Lon...	2 beds \| 1 baths \| 1,140 sq.ft.	$175,000	Airbnb cash on cash: -1.67% Traditional cash on cash: 3.49% Airbnb Rental Income: $1115 Traditional Rental Income: $1600 Airbnb ROI: -1.67% Traditional ROI: 3.49%
114 JUNIPER LANE Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Qu...	2 beds \| 2 baths \| 2,049 sq.ft.	$460,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 3.63% Airbnb Rental Income: $1115 Traditional Rental Income: $2469 Airbnb ROI: -0.39% Traditional ROI: 3.63%
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.	$649,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 3.36% Airbnb Rental Income: $5377 Traditional Rental Income: $3370 Airbnb ROI: 4.88% Traditional ROI: 3.36%
255 E HORNBEAM DRIVE Longwood, FL Welcome to this exquisitely remodeled residence in the highly desirable community of Sabal...	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%
257 GARY BOULEVARD Longwood, FL Under contract-accepting backup offers. Three bedrooms, two baths, a pool, and no HOA in o...	3 beds \| 2 baths \| 1,267 sq.ft.	$375,000	Airbnb cash on cash: 5.04% Traditional cash on cash: 4.06% Airbnb Rental Income: $3221 Traditional Rental Income: $2151 Airbnb ROI: 5.04% Traditional ROI: 4.06%
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%
451 STANTON PLACE Longwood, FL Welcome to Governorâs Point, a highly sought-after community in Wekiva, located in Longw...	3 beds \| 3 baths \| 1,682 sq.ft.	$334,900	Airbnb cash on cash: 3.82% Traditional cash on cash: 2.74% Airbnb Rental Income: $3221 Traditional Rental Income: $2154 Airbnb ROI: 3.82% Traditional ROI: 2.74%
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: 6.1% Airbnb Rental Income: $3221 Traditional Rental Income: $3557 Airbnb ROI: 3.4% Traditional ROI: 6.1%
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: 2.89% Airbnb Rental Income: $3221 Traditional Rental Income: $2079 Airbnb ROI: 3.91% Traditional ROI: 2.89%
1889 RANCHLAND TRAIL Longwood, FL Welcome to this beautifully renovated 4-bedroom, 3-bathroom pool home, perfectly situated ...	4 beds \| 3 baths \| 2,333 sq.ft.	$998,900	Airbnb cash on cash: 2.92% Traditional cash on cash: 2.18% Airbnb Rental Income: $5377 Traditional Rental Income: $3601 Airbnb ROI: 2.92% Traditional ROI: 2.18%
1386 S RIDGE LAKE CIRCLE Longwood, FL Under contract-accepting backup offers. .	4 beds \| 2 baths \| 2,263 sq.ft.	$535,000	Airbnb cash on cash: 6.23% Traditional cash on cash: 4.56% Airbnb Rental Income: $5377 Traditional Rental Income: $3456 Airbnb ROI: 6.23% Traditional ROI: 4.56%
126 SANDALWOOD WAY Longwood, FL Under contract-accepting backup offers. **This house comes with a REDUCED RATE through the...	3 beds \| 2 baths \| 1,354 sq.ft.	$404,900	Airbnb cash on cash: 4.06% Traditional cash on cash: 4.73% Airbnb Rental Income: $3221 Traditional Rental Income: $2751 Airbnb ROI: 4.06% Traditional ROI: 4.73%
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%
1742 FIFESHIRE COURT Longwood, FL Welcome home to your own immaculate sparkling screened in pool home nestled in a cul-de-sa...	5 beds \| 7 baths \| 4,053 sq.ft.	$1,275,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.82% Airbnb Rental Income: $null Traditional Rental Income: $4440 Airbnb ROI: N/A Traditional ROI: 1.82%
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: 4.21% Airbnb Rental Income: $5377 Traditional Rental Income: $8006 Airbnb ROI: 1.35% Traditional ROI: 4.21%
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%
470 FREEMAN STREET Longwood, FL Set on an oversized lot in the desirable Longwood Plantation community, 470 Freeman Street...	4 beds \| 2 baths \| 2,261 sq.ft.	$490,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 4.57% Airbnb Rental Income: $5377 Traditional Rental Income: $3094 Airbnb ROI: 7.19% Traditional ROI: 4.57%
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: 3.79% Airbnb Rental Income: $5377 Traditional Rental Income: $3121 Airbnb ROI: 6.54% Traditional ROI: 3.79%
284 ISLAND SOUND COURT Longwood, FL Step into refined elegance and effortless sophistication in this nearly new Dockside maste...	4 beds \| 3 baths \| 2,692 sq.ft.	$799,999	Airbnb cash on cash: 3.56% Traditional cash on cash: 1.67% Airbnb Rental Income: $5377 Traditional Rental Income: $2884 Airbnb ROI: 3.56% Traditional ROI: 1.67%
486 N PIN OAK PLACE #112 Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **...	2 beds \| 1 baths \| 959 sq.ft.	$187,900	Airbnb cash on cash: 1.44% Traditional cash on cash: 7.19% Airbnb Rental Income: $1115 Traditional Rental Income: $1767 Airbnb ROI: 1.44% Traditional ROI: 7.19%
1510 PELICAN STREET Longwood, FL Under contract-accepting backup offers. Completely Remodeled Home in Prime Location -NO HO...	3 beds \| 2 baths \| 1,269 sq.ft.	$349,999	Airbnb cash on cash: 5.02% Traditional cash on cash: 3.43% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 5.02% Traditional ROI: 3.43%
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: 5.47% Airbnb Rental Income: $5377 Traditional Rental Income: $3873 Airbnb ROI: 6.27% Traditional ROI: 5.47%
351 W HORNBEAM DRIVE Longwood, FL Under contract-accepting backup offers. Under Construction. Welcome to one of the most exc...	4 beds \| 3 baths \| 2,778 sq.ft.	$750,000	Airbnb cash on cash: 4.59% Traditional cash on cash: -0.34% Airbnb Rental Income: $5377 Traditional Rental Income: $850 Airbnb ROI: 4.59% Traditional ROI: -0.34%

Your search for investment property begins and ends here

Golden Highlands Investment Property for Sale in Longwood, FL

3996 RADLEY COURT #3996

Longwood, FL

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

$245,000

Airbnb cash on cash: -1.7%

Traditional cash on cash: 4.98%

Airbnb Rental Income: $1115

Traditional Rental Income: $2287

Airbnb ROI: -1.7%

Traditional ROI: 4.98%

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: 4.46%

Airbnb Rental Income: $1115

Traditional Rental Income: $1969

Airbnb ROI: -1.38%

Traditional ROI: 4.46%

417 SUMMIT RIDGE PLACE #213

Longwood, FL

2 beds | 2 baths | 1,274 sq.ft.

$239,000

Airbnb cash on cash: -1.49%

Traditional cash on cash: 3.52%

Airbnb Rental Income: $1115

Traditional Rental Income: $1871

Airbnb ROI: -1.49%

Traditional ROI: 3.52%

1665 GRANGE CIRCLE

Longwood, FL

3 beds | 2 baths | 2,189 sq.ft.

$399,000

Airbnb cash on cash: 4.28%

Traditional cash on cash: 6.3%

Airbnb Rental Income: $3221

Traditional Rental Income: $3251

Airbnb ROI: 4.28%

Traditional ROI: 6.3%

214 SHERIDAN AVENUE

Longwood, FL

3 beds | 2 baths | 1,707 sq.ft.

$425,000

Airbnb cash on cash: 3.88%

Traditional cash on cash: 3.41%

Airbnb Rental Income: $3221

Traditional Rental Income: $2306

Airbnb ROI: 3.88%

Traditional ROI: 3.41%

2681 AZALEA DRIVE

Longwood, FL

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

$345,000

Airbnb cash on cash: 5.28%

Traditional cash on cash: 3.74%

Airbnb Rental Income: $3221

Traditional Rental Income: $1994

Airbnb ROI: 5.28%

Traditional ROI: 3.74%

420 W WEKIVA TRAIL

Longwood, FL

3 beds | 2 baths | 1,787 sq.ft.

$448,000

Airbnb cash on cash: 3.74%

Traditional cash on cash: 3.16%

Airbnb Rental Income: $3221

Traditional Rental Income: $2251

Airbnb ROI: 3.74%

Traditional ROI: 3.16%

102 N SILVER CLUSTER COURT

Longwood, FL

3 beds | 2 baths | 1,166 sq.ft.

$395,000

Airbnb cash on cash: 4.46%

Traditional cash on cash: 3.07%

Airbnb Rental Income: $3221

Traditional Rental Income: $1980

Airbnb ROI: 4.46%