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 103 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
12 HORSEMAN COVE Longwood, FL Average monthly electric bill is $35.00 Welcome to this incredible opportunity in the ...	4 beds \| 2 baths \| 2,265 sq.ft.	$524,999	Airbnb cash on cash: 6.87% Traditional cash on cash: 4.24% Airbnb Rental Income: $5377 Traditional Rental Income: $3005 Airbnb ROI: 6.87% Traditional ROI: 4.24%
401 REIDER AVENUE Longwood, FL Lakefront living in the heart of Longwood! This charming 3-bedroom, 2-bath home is situate...	3 beds \| 2 baths \| 1,451 sq.ft.	$429,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 4.4% Airbnb Rental Income: $3221 Traditional Rental Income: $2527 Airbnb ROI: 4.32% Traditional ROI: 4.4%
2086 JUDITH PLACE Longwood, FL Under contract-accepting backup offers. ***Multiple offers have been made. Seller is reque...	4 beds \| 2 baths \| 2,763 sq.ft.	$714,900	Airbnb cash on cash: 4.77% Traditional cash on cash: 3.05% Airbnb Rental Income: $5377 Traditional Rental Income: $3145 Airbnb ROI: 4.77% Traditional ROI: 3.05%
641 E CHURCH AVENUE Longwood, FL Ready to save money on gas, your utility bills and home maintenance ? Welcome home to 641 ...	3 beds \| 2 baths \| 1,537 sq.ft.	$365,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 4.88% Airbnb Rental Income: $3221 Traditional Rental Income: $2253 Airbnb ROI: 5.59% Traditional ROI: 4.88%
205 HICKORY DRIVE Longwood, FL Beautifully Updated Pool Home in Sweetwater Oaks! Welcome to this stunning 4-bedroom, 2-ba...	4 beds \| 2 baths \| 1,867 sq.ft.	$599,900	Airbnb cash on cash: 5.66% Traditional cash on cash: 2.85% Airbnb Rental Income: $5377 Traditional Rental Income: $2718 Airbnb ROI: 5.66% Traditional ROI: 2.85%
2681 AZALEA DRIVE Longwood, FL Enjoy the best of Longwood living in this charming 3-bedroom, 2-bath home on a spacious qu...	3 beds \| 2 baths \| 1,399 sq.ft.	$375,000	Airbnb cash on cash: 4.79% Traditional cash on cash: 3.36% Airbnb Rental Income: $3221 Traditional Rental Income: $1994 Airbnb ROI: 4.79% Traditional ROI: 3.36%
364 HOWARD BOULEVARD Longwood, FL Welcome to this charming 3-bedroom, 2-bath home tucked away at the end of a quiet dead-end...	3 beds \| 2 baths \| 1,400 sq.ft.	$375,000	Airbnb cash on cash: 5.25% Traditional cash on cash: 4.19% Airbnb Rental Income: $3221 Traditional Rental Income: $2122 Airbnb ROI: 5.25% Traditional ROI: 4.19%
182 CITRUS TREE LANE Longwood, FL Welcome to this Charming, Beautifully Maintained 4-Bedroom, 2-Bath POOL Home located in th...	4 beds \| 2 baths \| 1,759 sq.ft.	$488,000	Airbnb cash on cash: 7.01% Traditional cash on cash: 3.65% Airbnb Rental Income: $5377 Traditional Rental Income: $2759 Airbnb ROI: 7.01% Traditional ROI: 3.65%
310 VISTA OAK DRIVE Longwood, FL ~MOTIVATED SELLER~ Welcome to your dream home in the highly sought-after gated community...	4 beds \| 5 baths \| 3,286 sq.ft.	$999,500	Airbnb cash on cash: 2.33% Traditional cash on cash: 3.65% Airbnb Rental Income: $5377 Traditional Rental Income: $5513 Airbnb ROI: 2.33% Traditional ROI: 3.65%
3340 PARK GROVE COURT Longwood, FL Elevated elegance meets exceptional design in this estate located on a premium cul-de-sac ...	4 beds \| 4 baths \| 3,266 sq.ft.	$1,299,000	Airbnb cash on cash: 1.3% Traditional cash on cash: 1.58% Airbnb Rental Income: $5377 Traditional Rental Income: $4635 Airbnb ROI: 1.3% Traditional ROI: 1.58%
2710 ENGLISH IVY CT Longwood, FL Under contract-accepting backup offers. Welcome to this stunning 4-bedroom, 4-bathroom hom...	4 beds \| 4 baths \| 4,219 sq.ft.	$1,100,000	Airbnb cash on cash: 1.89% Traditional cash on cash: 2.25% Airbnb Rental Income: $5377 Traditional Rental Income: $4668 Airbnb ROI: 1.89% Traditional ROI: 2.25%
345 W HORNBEAM DRIVE Longwood, FL Exquisite Modern Renovation in Sabal Point! Welcome to this stunningly remodeled 4-bedroo...	4 beds \| 2 baths \| 2,177 sq.ft.	$634,900	Airbnb cash on cash: 5.42% Traditional cash on cash: 3.44% Airbnb Rental Income: $5377 Traditional Rental Income: $3118 Airbnb ROI: 5.42% Traditional ROI: 3.44%
731 CRESTBROOK LOOP Longwood, FL Welcome to 731 Crestbrook Loop in The Landings- one of Longwoodâs most desirable gated ...	3 beds \| 3 baths \| 2,140 sq.ft.	$425,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 5.72% Airbnb Rental Income: $3221 Traditional Rental Income: $3173 Airbnb ROI: 4.02% Traditional ROI: 5.72%
2040 E TRIANGLE DRIVE Longwood, FL NEW PRICE REDUCTION! Now priced below market value. Charming, Updated 3-Bedroom Home ...	3 beds \| 2 baths \| 1,283 sq.ft.	$350,000	Airbnb cash on cash: 5.33% Traditional cash on cash: 3.56% Airbnb Rental Income: $3221 Traditional Rental Income: $1912 Airbnb ROI: 5.33% Traditional ROI: 3.56%
165 FIG TREE RUN Longwood, FL Welcome to 165 FIG TREE RUN, A Beautifully Updated Pool Home in the Gated Longwood Club Ne...	4 beds \| 2 baths \| 2,121 sq.ft.	$550,000	Airbnb cash on cash: 5.7% Traditional cash on cash: 3.07% Airbnb Rental Income: $5377 Traditional Rental Income: $2936 Airbnb ROI: 5.7% Traditional ROI: 3.07%
966 N RONALD REAGAN BOULEVARD Longwood, FL HIGH AND DRY! Located just 1/2 mile from the Longwood SunRail Station. Donât miss your o...	5 beds \| 3 baths \| 2,490 sq.ft.	$595,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.32% Airbnb Rental Income: $null Traditional Rental Income: $3535 Airbnb ROI: N/A Traditional ROI: 4.32%
4 HUDSON COVE Longwood, FL Fully Renovated 4-Bedroom Pool Home in the Heart of Central Florida. Welcome home! This...	4 beds \| 3 baths \| 2,263 sq.ft.	$579,999	Airbnb cash on cash: 5.77% Traditional cash on cash: 2.79% Airbnb Rental Income: $5377 Traditional Rental Income: $2678 Airbnb ROI: 5.77% Traditional ROI: 2.79%
674 PINE SHADOW COURT Longwood, FL Discover this beautifully maintained 4-bedroom, 3-bath home in the sought-after Sabal Poin...	4 beds \| 3 baths \| 2,754 sq.ft.	$710,000	Airbnb cash on cash: 4.75% Traditional cash on cash: 3.41% Airbnb Rental Income: $5377 Traditional Rental Income: $3403 Airbnb ROI: 4.75% Traditional ROI: 3.41%
342 MAPLE DRIVE Longwood, FL This amazing, meticulously remodeled one-story pool home offers an exceptional location fa...	4 beds \| 3 baths \| 2,799 sq.ft.	$844,000	Airbnb cash on cash: 3.66% Traditional cash on cash: 2.79% Airbnb Rental Income: $5377 Traditional Rental Income: $3609 Airbnb ROI: 3.66% Traditional ROI: 2.79%
300 SPRING RUN CIRCLE Longwood, FL Short Sale. Step into the lifestyle you've always dreamed of in the exclusive, guard gated...	3 beds \| 3 baths \| 2,416 sq.ft.	$524,900	Airbnb cash on cash: 3.05% Traditional cash on cash: 4.34% Airbnb Rental Income: $3221 Traditional Rental Income: $3128 Airbnb ROI: 3.05% Traditional ROI: 4.34%
223 ROYAL OAKS CIRCLE Longwood, FL IMPROVED PRICE! One of the BEST VALUES per square foot in Sweetwater Oaks! Welcome to one...	4 beds \| 2 baths \| 2,842 sq.ft.	$639,900	Airbnb cash on cash: 5.87% Traditional cash on cash: 3.23% Airbnb Rental Income: $5377 Traditional Rental Income: $2711 Airbnb ROI: 5.87% Traditional ROI: 3.23%
1510 PELICAN STREET Longwood, FL 3-bed, 2-bath residence nestled on a serene, tree-lined street in one of Longwoodâs DESI...	3 beds \| 2 baths \| 1,269 sq.ft.	$332,000	Airbnb cash on cash: 5.34% Traditional cash on cash: 3.67% Airbnb Rental Income: $3221 Traditional Rental Income: $1973 Airbnb ROI: 5.34% Traditional ROI: 3.67%
115 MARCY BOULEVARD Longwood, FL Under contract-accepting backup offers. Welcome to 115 Marcy Blvd, a charming residence ne...	5 beds \| 3 baths \| 2,013 sq.ft.	$499,995	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $3195 Airbnb ROI: N/A Traditional ROI: 4.41%
453 E Jessup Avenue Longwood, FL Fully Renovated Longwood Gem - Move-In Ready! Welcome to 453 E Jessup Ave, a beautifully r...	2 beds \| 1 baths \| 864 sq.ft.	$270,000	Airbnb cash on cash: 0.51% Traditional cash on cash: 3.76% Airbnb Rental Income: $1115 Traditional Rental Income: $1567 Airbnb ROI: 0.51% Traditional ROI: 3.76%
722 EAGLE AVENUE Longwood, FL Investor Goldmine in Longwood! Attention flippers, rehabbers, and savvy investors â This...	3 beds \| 2 baths \| 1,548 sq.ft.	$299,000	Airbnb cash on cash: 6.04% Traditional cash on cash: 4.82% Airbnb Rental Income: $3221 Traditional Rental Income: $2153 Airbnb ROI: 6.04% Traditional ROI: 4.82%
3 HORSEMAN COVE Longwood, FL Under contract-accepting backup offers. BACK ON THE MARKET --- NO FAULT OF THE SELLERS!!! ...	4 beds \| 3 baths \| 2,568 sq.ft.	$505,000	Airbnb cash on cash: 7.21% Traditional cash on cash: 5.6% Airbnb Rental Income: $5377 Traditional Rental Income: $3529 Airbnb ROI: 7.21% Traditional ROI: 5.6%
3277 LAKEVIEW OAKS DRIVE Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 4 baths \| 4,190 sq.ft.	$1,290,000	Airbnb cash on cash: 1.5% Traditional cash on cash: -0.41% Airbnb Rental Income: $5377 Traditional Rental Income: $1990 Airbnb ROI: 1.5% Traditional ROI: -0.41%
100 BLUE LAKE COURT Longwood, FL Exceptional lakefront executive estate with panoramic views of natural spring fed Lake Bra...	5 beds \| 7 baths \| 9,181 sq.ft.	$3,500,000	Airbnb cash on cash: N/A Traditional cash on cash: -1.07% Airbnb Rental Income: $null Traditional Rental Income: $1918 Airbnb ROI: N/A Traditional ROI: -1.07%
1833 MISTY MORN PLACE Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Ex...	5 beds \| 4 baths \| 3,506 sq.ft.	$995,000	Airbnb cash on cash: N/A Traditional cash on cash: 2.95% Airbnb Rental Income: $null Traditional Rental Income: $4653 Airbnb ROI: N/A Traditional ROI: 2.95%
203 RED BUD LANE Longwood, FL Under contract-accepting backup offers. Seller Motivated! Newly Remodeled executive home w...	4 beds \| 3 baths \| 3,219 sq.ft.	$549,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 3.66% Airbnb Rental Income: $5377 Traditional Rental Income: $3303 Airbnb ROI: 5.59% Traditional ROI: 3.66%
118 SHOMATE DRIVE Longwood, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	4 beds \| 2 baths \| 1,860 sq.ft.	$375,000	Airbnb cash on cash: 9.88% Traditional cash on cash: 4.71% Airbnb Rental Income: $5377 Traditional Rental Income: $2470 Airbnb ROI: 9.88% Traditional ROI: 4.71%
1821 STANLEY STREET Longwood, FL Seller will consider assisting buyer with closing cost and rate by down or other credits. ...	3 beds \| 2 baths \| 2,567 sq.ft.	$490,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 3.48% Airbnb Rental Income: $3221 Traditional Rental Income: $2427 Airbnb ROI: 3.63% Traditional ROI: 3.48%
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.	$559,000	Airbnb cash on cash: 3.19% Traditional cash on cash: 2.99% Airbnb Rental Income: $3221 Traditional Rental Income: $2395 Airbnb ROI: 3.19% Traditional ROI: 2.99%
1651 KENLYN DRIVE Longwood, FL This beautiful home is ready to be loved by new owners! Featuring 3 bedrooms, 2 bathrooms,...	3 beds \| 2 baths \| 1,687 sq.ft.	$375,000	Airbnb cash on cash: 4.58% Traditional cash on cash: 3.58% Airbnb Rental Income: $3221 Traditional Rental Income: $2142 Airbnb ROI: 4.58% Traditional ROI: 3.58%
215 NOB HILL CIRCLE Longwood, FL Looking for a deal? Fix and FLIP! LOCATION AND LAKEVIEW are ONE OF A KIND! Best deal on th...	4 beds \| 3 baths \| 2,538 sq.ft.	$500,000	Airbnb cash on cash: 7.5% Traditional cash on cash: 5.75% Airbnb Rental Income: $5377 Traditional Rental Income: $3475 Airbnb ROI: 7.5% Traditional ROI: 5.75%
1581 MONICA JOY CIRCLE Longwood, FL Just Appraised! Located in TOP RATED SEMINOLE COUNTY SCHOOL DISTRICT. Single story ranch h...	4 beds \| 2 baths \| 2,073 sq.ft.	$469,900	Airbnb cash on cash: 7.97% Traditional cash on cash: 4.04% Airbnb Rental Income: $5377 Traditional Rental Income: $2564 Airbnb ROI: 7.97% Traditional ROI: 4.04%
975 CROSS CUT WAY Longwood, FL Beautiful 4 bedroom 2.5 bathroom home Freshly Painted with Luxury Vinyl flooring and Stain...	4 beds \| 3 baths \| 2,289 sq.ft.	$475,000	Airbnb cash on cash: 7.08% Traditional cash on cash: 4.14% Airbnb Rental Income: $5377 Traditional Rental Income: $2982 Airbnb ROI: 7.08% Traditional ROI: 4.14%
2090 PRAIRIE SAGE LANE Longwood, FL Price Improvement! Welcome to this beautiful 4-bedroom, 2.5-bath home built in 2021, of...	4 beds \| 3 baths \| 2,471 sq.ft.	$550,000	Airbnb cash on cash: 5.66% Traditional cash on cash: 2.78% Airbnb Rental Income: $5377 Traditional Rental Income: $2813 Airbnb ROI: 5.66% Traditional ROI: 2.78%
218 W MAGNOLIA AVENUE Longwood, FL Under contract-accepting backup offers. 2025 TOTAL RENOVATION - PRICE IMPROVEMENT. Fully I...	3 beds \| 2 baths \| 1,574 sq.ft.	$381,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 3.74% Airbnb Rental Income: $3221 Traditional Rental Income: $2157 Airbnb ROI: 4.69% Traditional ROI: 3.74%
154 SHADOW TRAIL Longwood, FL Welcome to 154 Shadow Trail, a beautifully renovated pool home nestled in the heart of Lon...	3 beds \| 2 baths \| 1,417 sq.ft.	$439,900	Airbnb cash on cash: 3.74% Traditional cash on cash: 3.19% Airbnb Rental Income: $3221 Traditional Rental Income: $2270 Airbnb ROI: 3.74% Traditional ROI: 3.19%

Your search for investment property begins and ends here

Single Family Homes for Sale in Longwood, FL

12 HORSEMAN COVE

Longwood, FL

4 beds | 2 baths | 2,265 sq.ft.

$524,999

Airbnb cash on cash: 6.87%

Traditional cash on cash: 4.24%

Airbnb Rental Income: $5377

Traditional Rental Income: $3005

Airbnb ROI: 6.87%

Traditional ROI: 4.24%

401 REIDER AVENUE

Longwood, FL

3 beds | 2 baths | 1,451 sq.ft.

$429,000

Airbnb cash on cash: 4.32%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $3221

Traditional Rental Income: $2527

Airbnb ROI: 4.32%

Traditional ROI: 4.4%

2086 JUDITH PLACE

Longwood, FL

4 beds | 2 baths | 2,763 sq.ft.

$714,900

Airbnb cash on cash: 4.77%

Traditional cash on cash: 3.05%

Airbnb Rental Income: $5377

Traditional Rental Income: $3145

Airbnb ROI: 4.77%

Traditional ROI: 3.05%

641 E CHURCH AVENUE

Longwood, FL

3 beds | 2 baths | 1,537 sq.ft.

$365,000

Airbnb cash on cash: 5.59%

Traditional cash on cash: 4.88%

Airbnb Rental Income: $3221

Traditional Rental Income: $2253

Airbnb ROI: 5.59%

Traditional ROI: 4.88%

205 HICKORY DRIVE

Longwood, FL

4 beds | 2 baths | 1,867 sq.ft.

$599,900

Airbnb cash on cash: 5.66%

Traditional cash on cash: 2.85%

Airbnb Rental Income: $5377

Traditional Rental Income: $2718

Airbnb ROI: 5.66%

Traditional ROI: 2.85%

2681 AZALEA DRIVE

Longwood, FL

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

$375,000

Airbnb cash on cash: 4.79%

Traditional cash on cash: 3.36%

Airbnb Rental Income: $3221

Traditional Rental Income: $1994

Airbnb ROI: 4.79%

Traditional ROI: 3.36%

364 HOWARD BOULEVARD

Longwood, FL

3 beds | 2 baths | 1,400 sq.ft.

$375,000

Airbnb cash on cash: 5.25%

Traditional cash on cash: 4.19%

Airbnb Rental Income: $3221

Traditional Rental Income: $2122

Airbnb ROI: 5.25%

Traditional ROI: 4.19%

182 CITRUS TREE LANE

Longwood, FL

4 beds | 2 baths | 1,759 sq.ft.

$488,000

Airbnb cash on cash: 7.01%

Traditional cash on cash: 3.65%

Airbnb Rental Income: $5377

Traditional Rental Income: $2759

Airbnb ROI: 7.01%