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 81 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: 2.8% Traditional cash on cash: 3.8% Airbnb Rental Income: $2759 Traditional Rental Income: $2503 Airbnb ROI: 2.8% Traditional ROI: 3.8%
421 MEADOWRIDGE COVE Longwood, FL Welcome to this beautiful 4 bedroom 2 Â½ bath 2 STORY home in the exclusive gated communit...	4 beds \| 3 baths \| 3,048 sq.ft.	$650,000	Airbnb cash on cash: 0.11% Traditional cash on cash: 1.88% Airbnb Rental Income: $2332 Traditional Rental Income: $2828 Airbnb ROI: 0.11% Traditional ROI: 1.88%
102 N SILVER CLUSTER COURT Longwood, FL Under contract-accepting backup offers. Welcome to 102 Silver Cluster Ct N in Longwood, a ...	3 beds \| 2 baths \| 1,166 sq.ft.	$383,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 3.2% Airbnb Rental Income: $2759 Traditional Rental Income: $1980 Airbnb ROI: 3.56% Traditional ROI: 3.2%
1870 CROWLEY CIRCLE E Longwood, FL Under contract-accepting backup offers. Short Sale. Approved Short Sale. Welcome to your p...	4 beds \| 4 baths \| 3,258 sq.ft.	$625,000	Airbnb cash on cash: 0.41% Traditional cash on cash: 5.32% Airbnb Rental Income: $2332 Traditional Rental Income: $4618 Airbnb ROI: 0.41% Traditional ROI: 5.32%
884 CUTLER ROAD Longwood, FL One or more photo(s) has been virtually staged. - Price Improvement - Welcome to this beau...	5 beds \| 3 baths \| 2,601 sq.ft.	$599,000	Airbnb cash on cash: 5.17% Traditional cash on cash: 1.98% Airbnb Rental Income: $5048 Traditional Rental Income: $2235 Airbnb ROI: 5.17% Traditional ROI: 1.98%
478 SABAL TRAIL CIRCLE Longwood, FL NEW PRICE: As Of 6/15 : Welcome to the desirable Sabal Point community! Located at 478 S...	4 beds \| 3 baths \| 2,529 sq.ft.	$599,500	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.83% Airbnb Rental Income: $2332 Traditional Rental Income: $3502 Airbnb ROI: 0.71% Traditional ROI: 3.83%
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: 1.52% Traditional cash on cash: 5.25% Airbnb Rental Income: $2332 Traditional Rental Income: $3324 Airbnb ROI: 1.52% 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: 2.42% Traditional cash on cash: 6.1% Airbnb Rental Income: $2759 Traditional Rental Income: $3557 Airbnb ROI: 2.42% 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: 4.21% Traditional cash on cash: 3.59% Airbnb Rental Income: $2759 Traditional Rental Income: $1912 Airbnb ROI: 4.21% Traditional ROI: 3.59%
450 E WARREN AVENUE Longwood, FL Under contract-accepting backup offers. Situated on an oversized double lot in the heart o...	2 beds \| 1 baths \| 888 sq.ft.	$265,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 3.51% Airbnb Rental Income: $1600 Traditional Rental Income: $1587 Airbnb ROI: 1.74% Traditional ROI: 3.51%
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: 0.19% Traditional cash on cash: 2.18% Airbnb Rental Income: $2332 Traditional Rental Income: $3601 Airbnb ROI: 0.19% Traditional ROI: 2.18%
207 LONESOME PINE DRIVE Longwood, FL Under contract-accepting backup offers. FANTASTIC OPPORTUNITY IN SWEETWATER OAKS! Nestled ...	4 beds \| 2 baths \| 1,908 sq.ft.	$559,900	Airbnb cash on cash: 1.07% Traditional cash on cash: 2.08% Airbnb Rental Income: $2332 Traditional Rental Income: $2281 Airbnb ROI: 1.07% Traditional ROI: 2.08%
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: 1% Traditional cash on cash: 3.36% Airbnb Rental Income: $2332 Traditional Rental Income: $2919 Airbnb ROI: 1% Traditional ROI: 3.36%
101 CHERRY HILL CIRCLE Longwood, FL This 4 bedrooms/3 bathrooms home is ideal for families and those who enjoy entertaining. R...	4 beds \| 3 baths \| 2,359 sq.ft.	$699,000	Airbnb cash on cash: 0.62% Traditional cash on cash: 2.49% Airbnb Rental Income: $2332 Traditional Rental Income: $2973 Airbnb ROI: 0.62% Traditional ROI: 2.49%
470 FREEMAN STREET Longwood, FL Under contract-accepting backup offers. Set on an oversized lot with Water VIEWS in the de...	4 beds \| 2 baths \| 2,261 sq.ft.	$475,000	Airbnb cash on cash: 1.73% Traditional cash on cash: 4.75% Airbnb Rental Income: $2332 Traditional Rental Income: $3094 Airbnb ROI: 1.73% 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: 0.15% Traditional cash on cash: 1.67% Airbnb Rental Income: $2332 Traditional Rental Income: $2884 Airbnb ROI: 0.15% 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.	$509,900	Airbnb cash on cash: 1.64% Traditional cash on cash: 6.09% Airbnb Rental Income: $2332 Traditional Rental Income: $3873 Airbnb ROI: 1.64% Traditional ROI: 6.09%
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.	$475,000	Airbnb cash on cash: 2.6% Traditional cash on cash: 4.33% Airbnb Rental Income: $2759 Traditional Rental Income: $2881 Airbnb ROI: 2.6% Traditional ROI: 4.33%
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.	$499,000	Airbnb cash on cash: 2.28% Traditional cash on cash: 3.17% Airbnb Rental Income: $2759 Traditional Rental Income: $2523 Airbnb ROI: 2.28% Traditional ROI: 3.17%
495 HOWARD AVENUE Longwood, FL Under contract-accepting backup offers. Back on market! Welcome home! This stunning 4-bedr...	4 beds \| 2 baths \| 1,855 sq.ft.	$409,999	Airbnb cash on cash: 2.73% Traditional cash on cash: 4.74% Airbnb Rental Income: $2332 Traditional Rental Income: $2527 Airbnb ROI: 2.73% 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: 1.09% Traditional cash on cash: 2.79% Airbnb Rental Income: $5048 Traditional Rental Income: $6386 Airbnb ROI: 1.09% Traditional ROI: 2.79%
901 CUTLER ROAD Longwood, FL Pull over HONEY! This home is move it ready. Roof. 2023. AC 1 2020, AC 2 2022. Look at the...	3 beds \| 2 baths \| 2,226 sq.ft.	$525,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 3.23% Airbnb Rental Income: $2759 Traditional Rental Income: $2767 Airbnb ROI: 1.89% Traditional ROI: 3.23%
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.	$775,000	Airbnb cash on cash: 0.67% Traditional cash on cash: 3.24% Airbnb Rental Income: $2332 Traditional Rental Income: $3606 Airbnb ROI: 0.67% Traditional ROI: 3.24%
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: 0.02% Traditional cash on cash: 2.77% Airbnb Rental Income: $5048 Traditional Rental Income: $10650 Airbnb ROI: 0.02% Traditional ROI: 2.77%
204 BLUE LAKE DRIVE Longwood, FL Virtually Staged. This 4 bedroom, 3.5 bathroom pool home is the kind of home that makes ou...	4 beds \| 4 baths \| 2,914 sq.ft.	$719,000	Airbnb cash on cash: 0.94% Traditional cash on cash: 5.64% Airbnb Rental Income: $2332 Traditional Rental Income: $4902 Airbnb ROI: 0.94% Traditional ROI: 5.64%
1861 CROWLEY CIRCLE E Longwood, FL MOVE IN READY!! Welcome to your dream home! This spacious & updated 3-bedroom, 2-bathroom...	3 beds \| 2 baths \| 1,986 sq.ft.	$555,900	Airbnb cash on cash: 2.48% Traditional cash on cash: 3.89% Airbnb Rental Income: $2759 Traditional Rental Income: $2842 Airbnb ROI: 2.48% Traditional ROI: 3.89%
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.	$775,000	Airbnb cash on cash: 0.72% Traditional cash on cash: 3.17% Airbnb Rental Income: $2332 Traditional Rental Income: $3522 Airbnb ROI: 0.72% Traditional ROI: 3.17%
1833 CROWLEY CIRCLE Longwood, FL Virtually Staged. Welcome to 1833 Crowley Circle, a beautifully maintained POOL home offer...	5 beds \| 3 baths \| 2,742 sq.ft.	$550,000	Airbnb cash on cash: 5.65% Traditional cash on cash: 6.03% Airbnb Rental Income: $5048 Traditional Rental Income: $4214 Airbnb ROI: 5.65% Traditional ROI: 6.03%
110 DEVON COURT Longwood, FL Welcome to 110 Devon Court in Wekiva Hunt Club, where a quiet cul-de-sac setting, flexible...	3 beds \| 2 baths \| 1,770 sq.ft.	$449,900	Airbnb cash on cash: 3.21% Traditional cash on cash: 4.3% Airbnb Rental Income: $2759 Traditional Rental Income: $2573 Airbnb ROI: 3.21% Traditional ROI: 4.3%
1000 CROOKED OAK COURT Longwood, FL Virtually Staged. Updated Sweetwater Oaks! 4-bedroom, 3-bath retreat, 2,808 sq ft **open t...	4 beds \| 3 baths \| 2,808 sq.ft.	$599,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 4.82% Airbnb Rental Income: $2332 Traditional Rental Income: $4023 Airbnb ROI: 0.77% Traditional ROI: 4.82%
300 E SWEETWATER CREEK DRIVE Longwood, FL Gorgeous home in Sweetwater Oaks! 4 Bed \| 3 Bath \| 1.25 ACRES \| PRICED TO SELL ... Move-...	4 beds \| 3 baths \| 2,074 sq.ft.	$529,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 4.53% Airbnb Rental Income: $2332 Traditional Rental Income: $3134 Airbnb ROI: 1.74% Traditional ROI: 4.53%
320 FERDINAND DRIVE Longwood, FL Under contract-accepting backup offers. Virtually Staged. Welcome to this charming 3-bedro...	3 beds \| 2 baths \| 1,852 sq.ft.	$445,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 5.17% Airbnb Rental Income: $2759 Traditional Rental Income: $3060 Airbnb ROI: 2.89% Traditional ROI: 5.17%
1805 MEADOWBEND DRIVE Longwood, FL Priced below appraisal. Welcome to 1805 Meadowbend Dr, a small gated enclave of 6 estate ...	5 beds \| 4 baths \| 4,000 sq.ft.	$1,400,000	Airbnb cash on cash: 1.45% Traditional cash on cash: 2.3% Airbnb Rental Income: $5048 Traditional Rental Income: $5124 Airbnb ROI: 1.45% Traditional ROI: 2.3%
1856 ALAQUA DRIVE Longwood, FL PRICE REDUCED! Welcome to Alaqua Drive, Luxurious Upgraded Executive Home Reflects Timeles...	5 beds \| 5 baths \| 4,007 sq.ft.	$1,399,000	Airbnb cash on cash: 1.13% Traditional cash on cash: 3.87% Airbnb Rental Income: $5048 Traditional Rental Income: $7578 Airbnb ROI: 1.13% Traditional ROI: 3.87%
216 THISTLEWOOD CIRCLE Longwood, FL Under contract-accepting backup offers. Nestled within the coveted community of Sweetwater...	4 beds \| 3 baths \| 2,272 sq.ft.	$619,900	Airbnb cash on cash: 0.74% Traditional cash on cash: 4.14% Airbnb Rental Income: $2332 Traditional Rental Income: $3722 Airbnb ROI: 0.74% Traditional ROI: 4.14%
1950 ELKHORN COURT Longwood, FL A rare opportunity to own in Hidden Cove, an intimate gated community of just 37 homes whe...	5 beds \| 4 baths \| 3,422 sq.ft.	$824,850	Airbnb cash on cash: 3.29% Traditional cash on cash: 4.17% Airbnb Rental Income: $5048 Traditional Rental Income: $4695 Airbnb ROI: 3.29% Traditional ROI: 4.17%
739 RIVERBEND BOULEVARD Longwood, FL Welcome to 739 Riverbend Blvd, a rare Sweetwater Oaks offering where space, setting, and l...	4 beds \| 2 baths \| 2,382 sq.ft.	$625,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 3.8% Airbnb Rental Income: $2332 Traditional Rental Income: $3241 Airbnb ROI: 1.25% Traditional ROI: 3.8%
1707 GRANGE CIRCLE Longwood, FL Welcome to this beautifully maintained 4-bedroom, 2-bath pool home Located in a desirable ...	4 beds \| 2 baths \| 1,981 sq.ft.	$468,000	Airbnb cash on cash: 2.31% Traditional cash on cash: 5.86% Airbnb Rental Income: $2332 Traditional Rental Income: $3311 Airbnb ROI: 2.31% Traditional ROI: 5.86%
1949 DEERVIEW PLACE Longwood, FL Donât miss this stunning Mediterranean estate home in the highly sought-after gated comm...	4 beds \| 5 baths \| 3,498 sq.ft.	$798,000	Airbnb cash on cash: 0.44% Traditional cash on cash: 5.57% Airbnb Rental Income: $2332 Traditional Rental Income: $5569 Airbnb ROI: 0.44% Traditional ROI: 5.57%
936 CITRUS WOOD COURT Longwood, FL Under contract-accepting backup offers. Virtually Staged. Welcome to this beautifully upda...	4 beds \| 2 baths \| 1,833 sq.ft.	$474,900	Airbnb cash on cash: 1.64% Traditional cash on cash: 4.84% Airbnb Rental Income: $2332 Traditional Rental Income: $3177 Airbnb ROI: 1.64% Traditional ROI: 4.84%

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: 2.8%

Traditional cash on cash: 3.8%

Airbnb Rental Income: $2759

Traditional Rental Income: $2503

Airbnb ROI: 2.8%

Traditional ROI: 3.8%

421 MEADOWRIDGE COVE

Longwood, FL

4 beds | 3 baths | 3,048 sq.ft.

$650,000

Airbnb cash on cash: 0.11%

Traditional cash on cash: 1.88%

Airbnb Rental Income: $2332

Traditional Rental Income: $2828

Airbnb ROI: 0.11%

Traditional ROI: 1.88%

102 N SILVER CLUSTER COURT

Longwood, FL

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

$383,000

Airbnb cash on cash: 3.56%

Traditional cash on cash: 3.2%

Airbnb Rental Income: $2759

Traditional Rental Income: $1980

Airbnb ROI: 3.56%

Traditional ROI: 3.2%

1870 CROWLEY CIRCLE E

Longwood, FL

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

$625,000

Airbnb cash on cash: 0.41%

Traditional cash on cash: 5.32%

Airbnb Rental Income: $2332

Traditional Rental Income: $4618

Airbnb ROI: 0.41%

Traditional ROI: 5.32%

884 CUTLER ROAD

Longwood, FL

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

$599,000

Airbnb cash on cash: 5.17%

Traditional cash on cash: 1.98%

Airbnb Rental Income: $5048

Traditional Rental Income: $2235

Airbnb ROI: 5.17%

Traditional ROI: 1.98%

478 SABAL TRAIL CIRCLE

Longwood, FL

4 beds | 3 baths | 2,529 sq.ft.

$599,500

Airbnb cash on cash: 0.71%

Traditional cash on cash: 3.83%

Airbnb Rental Income: $2332

Traditional Rental Income: $3502

Airbnb ROI: 0.71%

Traditional ROI: 3.83%

860 Charlotte St.

Longwood, FL

4 beds | 4 baths | N/A

$449,000

Airbnb cash on cash: 1.52%

Traditional cash on cash: 5.25%

Airbnb Rental Income: $2332

Traditional Rental Income: $3324

Airbnb ROI: 1.52%

Traditional ROI: 5.25%

1025 BUCKSAW PLACE

Longwood, FL

3 beds | 3 baths | 2,289 sq.ft.

$419,000

Airbnb cash on cash: 2.42%

Traditional cash on cash: 6.1%

Airbnb Rental Income: $2759

Traditional Rental Income: $3557

Airbnb ROI: 2.42%