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 93 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
276 W BAY AVENUE Longwood, FL Step into the timeless elegance of this beautifully crafted Victorian Home, newer construc...	3 beds \| 3 baths \| 1,814 sq.ft.	$419,000	Airbnb cash on cash: 3.78% Traditional cash on cash: 3.8% Airbnb Rental Income: $3221 Traditional Rental Income: $2503 Airbnb ROI: 3.78% Traditional ROI: 3.8%
1665 GRANGE CIRCLE Longwood, FL Under contract-accepting backup offers. Expect to be impressed with this beautiful 3-bedro...	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%
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.	$383,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 3.2% Airbnb Rental Income: $3221 Traditional Rental Income: $1980 Airbnb ROI: 4.63% Traditional ROI: 3.2%
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%
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.	$615,000	Airbnb cash on cash: N/A Traditional cash on cash: 1.91% Airbnb Rental Income: $null Traditional Rental Income: $2235 Airbnb ROI: N/A Traditional ROI: 1.91%
413 WILLOWBROOK LANE Longwood, FL One or more photo(s) has been virtually staged. Located in the highly sought-after Sabal P...	4 beds \| 2 baths \| 2,211 sq.ft.	$564,999	Airbnb cash on cash: 6.13% Traditional cash on cash: 4.96% Airbnb Rental Income: $5377 Traditional Rental Income: $3678 Airbnb ROI: 6.13% Traditional ROI: 4.96%
478 SABAL TRAIL CIRCLE Longwood, FL PRICE ADJUSTMENT : Welcome to the desirable Sabal Point community! Located at 478 Sabal Tr...	4 beds \| 3 baths \| 2,529 sq.ft.	$629,900	Airbnb cash on cash: 4.94% Traditional cash on cash: 3.6% Airbnb Rental Income: $5377 Traditional Rental Income: $3502 Airbnb ROI: 4.94% Traditional ROI: 3.6%
308 SMOKERISE BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to 308 Smokerise Blvd., tucked away on a q...	4 beds \| 2 baths \| 2,352 sq.ft.	$635,000	Airbnb cash on cash: 5.01% Traditional cash on cash: 3.46% Airbnb Rental Income: $5377 Traditional Rental Income: $3370 Airbnb ROI: 5.01% Traditional ROI: 3.46%
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: 6.1% Airbnb Rental Income: $3221 Traditional Rental Income: $3557 Airbnb ROI: 3.4% Traditional ROI: 6.1%
2040 E TRIANGLE DRIVE Longwood, FL Beautiful opportunity in the highly desirable Longwood area, perfectly located just minute...	3 beds \| 2 baths \| 1,283 sq.ft.	$340,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 3.59% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.42% Traditional ROI: 3.59%
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%
965 BUCKSAW PLACE Longwood, FL Under contract-accepting backup offers. Welcome to this spacious 4-bedroom, 3-bath home in...	4 beds \| 3 baths \| 2,361 sq.ft.	$530,000	Airbnb cash on cash: 6.13% Traditional cash on cash: 3.36% Airbnb Rental Income: $5377 Traditional Rental Income: $2919 Airbnb ROI: 6.13% Traditional ROI: 3.36%
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%
470 FREEMAN STREET Longwood, FL Set on an oversized lot with Water VIEWS in the desirable Longwood Plantation community, 4...	4 beds \| 2 baths \| 2,261 sq.ft.	$475,000	Airbnb cash on cash: 7.44% Traditional cash on cash: 4.75% Airbnb Rental Income: $5377 Traditional Rental Income: $3094 Airbnb ROI: 7.44% Traditional ROI: 4.75%
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%
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.	$539,000	Airbnb cash on cash: 6.54% Traditional cash on cash: 5.71% Airbnb Rental Income: $5377 Traditional Rental Income: $3873 Airbnb ROI: 6.54% Traditional ROI: 5.71%
351 W HORNBEAM DRIVE Longwood, FL Under Construction. Welcome to one of the most exciting new builds to hit Longwood's covet...	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%
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: 4.22% Airbnb Rental Income: $3221 Traditional Rental Income: $2881 Airbnb ROI: 3.37% Traditional ROI: 4.22%
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: 3.68% Airbnb Rental Income: $5377 Traditional Rental Income: $8614 Airbnb ROI: 0.72% Traditional ROI: 3.68%
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 Some homes just feel right the moment you walk inâ¦ and 307 Coble Drive is one of them. ...	4 beds \| 2 baths \| 1,987 sq.ft.	$475,000	Airbnb cash on cash: 7.19% Traditional cash on cash: 4.8% Airbnb Rental Income: $5377 Traditional Rental Income: $3230 Airbnb ROI: 7.19% Traditional ROI: 4.8%
605 WATER OAK LANE Longwood, FL Florida Dream Home on Over Half an Acre in One of Longwoodâs Most Desirable Neighborhood...	3 beds \| 2 baths \| 1,831 sq.ft.	$509,900	Airbnb cash on cash: 3.02% Traditional cash on cash: 3.08% Airbnb Rental Income: $3221 Traditional Rental Income: $2523 Airbnb ROI: 3.02% Traditional ROI: 3.08%
495 HOWARD AVENUE Longwood, FL Back on market! Welcome home! This stunning 4-bedroom, 2-bathroom residence has been compl...	4 beds \| 2 baths \| 1,855 sq.ft.	$409,999	Airbnb cash on cash: 9.34% Traditional cash on cash: 4.74% Airbnb Rental Income: $5377 Traditional Rental Income: $2527 Airbnb ROI: 9.34% Traditional ROI: 4.74%
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%
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: 3.11% Airbnb Rental Income: $5377 Traditional Rental Income: $3606 Airbnb ROI: 4.03% Traditional ROI: 3.11%
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.	$719,000	Airbnb cash on cash: 4.73% Traditional cash on cash: 5.64% Airbnb Rental Income: $5377 Traditional Rental Income: $4902 Airbnb ROI: 4.73% Traditional ROI: 5.64%
1861 CROWLEY CIRCLE E Longwood, FL Exceptional Opportunity to own a home off the celebrated Markham Woods Road, the area once...	3 beds \| 2 baths \| 1,986 sq.ft.	$565,900	Airbnb cash on cash: 3.15% Traditional cash on cash: 3.8% Airbnb Rental Income: $3221 Traditional Rental Income: $2842 Airbnb ROI: 3.15% Traditional ROI: 3.8%
1209 ROXBORO ROAD Longwood, FL Fully Renovated Knollwood Estate \| Over $315K in Upgrades \| 0.70 Acre Lot Welcome to Ro...	4 beds \| 3 baths \| 3,332 sq.ft.	$799,999	Airbnb cash on cash: 4.07% Traditional cash on cash: 3.04% Airbnb Rental Income: $5377 Traditional Rental Income: $3522 Airbnb ROI: 4.07% Traditional ROI: 3.04%
1833 CROWLEY CIRCLE Longwood, FL One or more photo(s) has been virtually staged. Welcome to 1833 Crowley Circle, a beautifu...	5 beds \| 3 baths \| 2,742 sq.ft.	$574,900	Airbnb cash on cash: N/A Traditional cash on cash: 5.73% Airbnb Rental Income: $null Traditional Rental Income: $4214 Airbnb ROI: N/A Traditional ROI: 5.73%
1401 WINDSOR AVENUE Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. El...	4 beds \| 4 baths \| 3,576 sq.ft.	$759,900	Airbnb cash on cash: 4.37% Traditional cash on cash: 6.46% Airbnb Rental Income: $5377 Traditional Rental Income: $5770 Airbnb ROI: 4.37% Traditional ROI: 6.46%
110 DEVON COURT Longwood, FL NEW PRICE! You are going to fall in love with this beautiful residence in desirable Longwo...	3 beds \| 2 baths \| 1,690 sq.ft.	$450,000	Airbnb cash on cash: 4.07% Traditional cash on cash: 4.25% Airbnb Rental Income: $3221 Traditional Rental Income: $2573 Airbnb ROI: 4.07% Traditional ROI: 4.25%
248 Cambridge Drive Longwood, FL Price Improvement - Now $505,000! Low HOA Move-in ready pool home in an established Longwo...	3 beds \| 3 baths \| 2,001 sq.ft.	$505,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 5.13% Airbnb Rental Income: $3221 Traditional Rental Income: $3404 Airbnb ROI: 3.2% Traditional ROI: 5.13%
1000 CROOKED OAK COURT Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Up...	4 beds \| 3 baths \| 2,808 sq.ft.	$599,900	Airbnb cash on cash: 5.3% Traditional cash on cash: 4.82% Airbnb Rental Income: $5377 Traditional Rental Income: $4023 Airbnb ROI: 5.3% Traditional ROI: 4.82%
506 FREEMAN STREET Longwood, FL Under contract-accepting backup offers. This impressive and spacious 5â6 bedroom, 4-bath...	5 beds \| 4 baths \| 3,459 sq.ft.	$588,500	Airbnb cash on cash: N/A Traditional cash on cash: 6.39% Airbnb Rental Income: $null Traditional Rental Income: $4639 Airbnb ROI: N/A Traditional ROI: 6.39%
2471 JENNIFER HOPE BOULEVARD Longwood, FL This luxury lakefront estate on Lake Brantley delivers the ultimate Central Florida waterf...	4 beds \| 4 baths \| 3,788 sq.ft.	$2,250,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 0.94% Airbnb Rental Income: $5377 Traditional Rental Income: $5545 Airbnb ROI: 0.34% Traditional ROI: 0.94%

Your search for investment property begins and ends here

Single Family Homes for Sale in Longwood, FL

276 W BAY AVENUE

Longwood, FL

3 beds | 3 baths | 1,814 sq.ft.

$419,000

Airbnb cash on cash: 3.78%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $3221

Traditional Rental Income: $2503

Airbnb ROI: 3.78%

Traditional ROI: 3.8%

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%

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.

$383,000

Airbnb cash on cash: 4.63%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $3221

Traditional Rental Income: $1980

Airbnb ROI: 4.63%

Traditional ROI: 3.2%

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%

884 CUTLER ROAD

Longwood, FL

5 beds | 3 baths | 2,601 sq.ft.

$615,000

Airbnb cash on cash: N/A

Traditional cash on cash: 1.91%

Airbnb Rental Income: $null

Traditional Rental Income: $2235

Airbnb ROI: N/A

Traditional ROI: 1.91%

413 WILLOWBROOK LANE

Longwood, FL

4 beds | 2 baths | 2,211 sq.ft.

$564,999

Airbnb cash on cash: 6.13%

Traditional cash on cash: 4.96%

Airbnb Rental Income: $5377

Traditional Rental Income: $3678

Airbnb ROI: 6.13%