Real Estate Investment Properties for Sale in Leesburg, FL

Looking for investment property in Leesburg, FL with high ROI ?

Explore a variety of short-term homes & houses in Leesburg, FL. Invest wisely with VRBO & Leesburg, FL Airbnb properties available for purchase. Find your ideal investment property among our curated listings for a rewarding real estate venture.

Investment Property for Sale in Leesburg, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
6750 SUNNYSIDE DRIVE Leesburg, FL Under contract-accepting backup offers. ACCEPTING BACK-UP OFFERS**Discover this quiet home...	3 beds \| 2 baths \| 2,082 sq.ft.	$399,900	Airbnb cash on cash: 4.32% Traditional cash on cash: 4.21% Airbnb Rental Income: $3164 Traditional Rental Income: $2408 Airbnb ROI: 4.32% Traditional ROI: 4.21%
25523 MAUREPAS LANE Leesburg, FL Expect to Be Charmed! Welcome to the classic Pandorea Floor Plan located on desirable Maur...	3 beds \| 3 baths \| 2,675 sq.ft.	$419,800	Airbnb cash on cash: 3.61% Traditional cash on cash: 4.48% Airbnb Rental Income: $3164 Traditional Rental Income: $2788 Airbnb ROI: 3.61% Traditional ROI: 4.48%
26822 BULL RUN Leesburg, FL LOCATION, LOCATION! Just steps away from the clubhouse and pool, this exquisite 3-bedroom,...	3 beds \| 2 baths \| 1,599 sq.ft.	$339,000	Airbnb cash on cash: 4.4% Traditional cash on cash: 3.14% Airbnb Rental Income: $3164 Traditional Rental Income: $2047 Airbnb ROI: 4.4% Traditional ROI: 3.14%
24112 ROBINWOOD STREET Leesburg, FL Upon Entering, you'll appreciate how open, bright, and functional this meticulously-kept 2...	2 beds \| 2 baths \| 2,071 sq.ft.	$375,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 3.68% Airbnb Rental Income: $1980 Traditional Rental Income: $2122 Airbnb ROI: 1.8% Traditional ROI: 3.68%
18 WESTON ROAD Leesburg, FL WATERFRONT RETREAT MEETS ENERGY EFFICIENCY! Welcome to 18 Weston Rd, where modern comfo...	3 beds \| 2 baths \| 2,016 sq.ft.	$489,990	Airbnb cash on cash: 3.31% Traditional cash on cash: 4.1% Airbnb Rental Income: $3164 Traditional Rental Income: $2809 Airbnb ROI: 3.31% Traditional ROI: 4.1%
4110 ARLINGTON RIDGE BOULEVARD Leesburg, FL PRICE CHANGE! Charming 4-Bedroom Home on the 17th Hole in Arlington Ridge â Privacy, Upg...	4 beds \| 2 baths \| 1,857 sq.ft.	$389,900	Airbnb cash on cash: 7.88% Traditional cash on cash: 3.43% Airbnb Rental Income: $4837 Traditional Rental Income: $2216 Airbnb ROI: 7.88% Traditional ROI: 3.43%
11114 LAKE EUSTIS DRIVE Leesburg, FL Welcome to your waterfront retreat! This charming three-bedroom, one-bath canal front home...	3 beds \| 1 baths \| 1,122 sq.ft.	$335,000	Airbnb cash on cash: 5.51% Traditional cash on cash: 3.06% Airbnb Rental Income: $3164 Traditional Rental Income: $1679 Airbnb ROI: 5.51% Traditional ROI: 3.06%
25545 LAUREL VALLEY RD Leesburg, FL Step into the lifestyle youâve been dreaming of in the vibrant 55+ community of Plantati...	2 beds \| 2 baths \| 2,399 sq.ft.	$349,900	Airbnb cash on cash: 1.61% Traditional cash on cash: 3.82% Airbnb Rental Income: $1980 Traditional Rental Income: $2187 Airbnb ROI: 1.61% Traditional ROI: 3.82%
416 HANCOCK ROAD Leesburg, FL 9-acre LAKEFRONT DREAM HOME ON LAKE GRIFFIN with NEW CUSTOM SCREENED IN $250K BOATHOUSE wi...	3 beds \| 4 baths \| 3,207 sq.ft.	$1,350,000	Airbnb cash on cash: 0.14% Traditional cash on cash: 3.12% Airbnb Rental Income: $3164 Traditional Rental Income: $6189 Airbnb ROI: 0.14% Traditional ROI: 3.12%
27327 ROANOKE DRIVE Leesburg, FL Welcome to this stunning 3-bedroom, 2-bath residence nestled in a vibrant active 55+ commu...	3 beds \| 2 baths \| 1,712 sq.ft.	$395,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 2.24% Airbnb Rental Income: $3164 Traditional Rental Income: $2016 Airbnb ROI: 3.4% Traditional ROI: 2.24%
26951 WHITE PLAINS WAY Leesburg, FL Affordable Modern 2 bedroom, 2 bath, Maintenance-free exterior & yardwork Villa built in 2...	2 beds \| 2 baths \| 1,418 sq.ft.	$255,000	Airbnb cash on cash: 2.52% Traditional cash on cash: 4.96% Airbnb Rental Income: $1980 Traditional Rental Income: $2049 Airbnb ROI: 2.52% Traditional ROI: 4.96%
5318 FANTASY WAY Leesburg, FL One or more photo(s) has been virtually staged. Enjoy peace of mind and modern comfort wit...	3 beds \| 2 baths \| 2,182 sq.ft.	$374,000	Airbnb cash on cash: 4.04% Traditional cash on cash: 3.46% Airbnb Rental Income: $3164 Traditional Rental Income: $2244 Airbnb ROI: 4.04% Traditional ROI: 3.46%
4553 BELLE GROVE Leesburg, FL A VA assumable mortgage at just 2.8% makes this home an even more appealing opportunity. W...	2 beds \| 2 baths \| 1,420 sq.ft.	$240,000	Airbnb cash on cash: 3.39% Traditional cash on cash: 5.2% Airbnb Rental Income: $1980 Traditional Rental Income: $1871 Airbnb ROI: 3.39% Traditional ROI: 5.2%
3706 BELLE ROSE DRIVE Leesburg, FL One or more photo(s) has been virtually staged. Seller may consider buyer concessions if m...	3 beds \| 2 baths \| 1,935 sq.ft.	$325,000	Airbnb cash on cash: 4.8% Traditional cash on cash: 3.52% Airbnb Rental Income: $3164 Traditional Rental Income: $2057 Airbnb ROI: 4.8% Traditional ROI: 3.52%
506 PERKINS STREET Leesburg, FL LOCATION, LOCATION, LOCATION! SOOO many possibilities. 3bedrooms plus a possible 4th bed...	3 beds \| 2 baths \| 1,972 sq.ft.	$297,900	Airbnb cash on cash: 6.48% Traditional cash on cash: 10.52% Airbnb Rental Income: $3164 Traditional Rental Income: $3580 Airbnb ROI: 6.48% Traditional ROI: 10.52%
10323 JOANIES RUN Leesburg, FL * Buyer's incentives improved, $8,000 flex money towards buyer's closing costs * Welco...	3 beds \| 2 baths \| 1,630 sq.ft.	$323,000	Airbnb cash on cash: 5.95% Traditional cash on cash: 4.48% Airbnb Rental Income: $3164 Traditional Rental Income: $2003 Airbnb ROI: 5.95% Traditional ROI: 4.48%
1906 ANGEL FISH LOOP Leesburg, FL ???? Modern Comfort with a Splash of Luxury Built in 2020, this spacious block/stucco hom...	3 beds \| 2 baths \| 2,035 sq.ft.	$359,900	Airbnb cash on cash: 5.22% Traditional cash on cash: 5.78% Airbnb Rental Income: $3164 Traditional Rental Income: $2635 Airbnb ROI: 5.22% Traditional ROI: 5.78%
5062 EL DESTINO DRIVE Leesburg, FL Outstanding one-story home with a screened porch and a beautiful and tranquil backyard wit...	3 beds \| 2 baths \| 1,021 sq.ft.	$264,000	Airbnb cash on cash: 6.87% Traditional cash on cash: 3.53% Airbnb Rental Income: $3164 Traditional Rental Income: $1616 Airbnb ROI: 6.87% Traditional ROI: 3.53%
25304 FOREST OAK COURT Leesburg, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. **...	3 beds \| 2 baths \| 2,460 sq.ft.	$372,500	Airbnb cash on cash: 4.12% Traditional cash on cash: 3.82% Airbnb Rental Income: $3164 Traditional Rental Income: $2345 Airbnb ROI: 4.12% Traditional ROI: 3.82%
33211 PENNBROOKE PARKWAY Leesburg, FL Stunning 2-bedroom, 2-bath home with a den, spacious 2-car garage, and a separate golf car...	2 beds \| 2 baths \| 1,707 sq.ft.	$316,000	Airbnb cash on cash: 1.83% Traditional cash on cash: 4.04% Airbnb Rental Income: $1980 Traditional Rental Income: $2118 Airbnb ROI: 1.83% Traditional ROI: 4.04%
33441 IRONGATE DRIVE Leesburg, FL 3 bedroom, 2 bath home nestled in a peaceful cul-de-sac in the esteemed Stonegate at Silve...	3 beds \| 2 baths \| 1,364 sq.ft.	$294,000	Airbnb cash on cash: 5.98% Traditional cash on cash: 4.03% Airbnb Rental Income: $3164 Traditional Rental Income: $1907 Airbnb ROI: 5.98% Traditional ROI: 4.03%
35219 HAINES CREEK ROAD Leesburg, FL Welcome to Riverside Community. Your 3-bedroom, 2-bath home with a 2-car garage offering p...	3 beds \| 2 baths \| 1,694 sq.ft.	$339,900	Airbnb cash on cash: 5.33% Traditional cash on cash: 4.78% Airbnb Rental Income: $3164 Traditional Rental Income: $2272 Airbnb ROI: 5.33% Traditional ROI: 4.78%
10330 PLEASANT VIEW DR Leesburg, FL HIGHLY DESIRED OAKMONT AT SILVER LAKE!!! LOCATION!!! Open Floor Plan, Beautifully Upgraded...	3 beds \| 2 baths \| 1,781 sq.ft.	$365,000	Airbnb cash on cash: 5.16% Traditional cash on cash: 4.28% Airbnb Rental Income: $3164 Traditional Rental Income: $2149 Airbnb ROI: 5.16% Traditional ROI: 4.28%
5610 KING JAMES AVENUE Leesburg, FL One or more photo(s) has been virtually staged. Gated Community Charming home, Customized ...	3 beds \| 2 baths \| 1,606 sq.ft.	$249,900	Airbnb cash on cash: 7.42% Traditional cash on cash: 5.83% Airbnb Rental Income: $3164 Traditional Rental Income: $2072 Airbnb ROI: 7.42% Traditional ROI: 5.83%
34016 VALENCIA DRIVE Leesburg, FL Spacious 3-Bedroom Home on Oversized Lot â Prime Central Location! Welcome to this be...	3 beds \| 2 baths \| 1,689 sq.ft.	$315,000	Airbnb cash on cash: 5.8% Traditional cash on cash: 4.48% Airbnb Rental Income: $3164 Traditional Rental Income: $2059 Airbnb ROI: 5.8% Traditional ROI: 4.48%
3601 MOUNT HOPE LOOP Leesburg, FL Stunning and Upgraded Maple Floor Plan in Glendale Village. Welcome to this beautifully up...	2 beds \| 2 baths \| 1,723 sq.ft.	$289,900	Airbnb cash on cash: 2.1% Traditional cash on cash: 4.13% Airbnb Rental Income: $1980 Traditional Rental Income: $2015 Airbnb ROI: 2.1% Traditional ROI: 4.13%
33413 FAIRWAY ROAD Leesburg, FL Short Sale. Because of job transfer, sellers absolutely must move! Don't miss this lovely ...	4 beds \| 3 baths \| 2,760 sq.ft.	$416,000	Airbnb cash on cash: 7.83% Traditional cash on cash: 4.93% Airbnb Rental Income: $5065 Traditional Rental Income: $2902 Airbnb ROI: 7.83% Traditional ROI: 4.93%
25800 BELLE HELENE Leesburg, FL This home sits on a Large Corner Lot in The Plantation a stunning 55 and over golf communi...	3 beds \| 2 baths \| 1,653 sq.ft.	$252,000	Airbnb cash on cash: 6.96% Traditional cash on cash: 5.28% Airbnb Rental Income: $3164 Traditional Rental Income: $2049 Airbnb ROI: 6.96% Traditional ROI: 5.28%
7838 SLOEWOOD DRIVE Leesburg, FL Take a look at this stunning home in the Seasons At Park Hill area of Leesburg! This 2022 ...	3 beds \| 2 baths \| 1,904 sq.ft.	$465,900	Airbnb cash on cash: 3.17% Traditional cash on cash: 2.57% Airbnb Rental Income: $3164 Traditional Rental Income: $2188 Airbnb ROI: 3.17% Traditional ROI: 2.57%
24954 NAVEL AVENUE Leesburg, FL Under contract-accepting backup offers. A must see, this beautifully maintained 3-bedroom,...	3 beds \| 2 baths \| 1,718 sq.ft.	$300,000	Airbnb cash on cash: 5.57% Traditional cash on cash: 4.41% Airbnb Rental Income: $3164 Traditional Rental Income: $2120 Airbnb ROI: 5.57% Traditional ROI: 4.41%
723 PERKINS STREET #104 Leesburg, FL One or more photo(s) has been virtually staged. This updated 2-bedroom, 2-bath FIRST FLOOR...	2 beds \| 2 baths \| 1,062 sq.ft.	$114,000	Airbnb cash on cash: 6.9% Traditional cash on cash: 6.83% Airbnb Rental Income: $1980 Traditional Rental Income: $1453 Airbnb ROI: 6.9% Traditional ROI: 6.83%
10308 PEBBLESTONE COURT Leesburg, FL Just the right size, nearly 1500 SF and move-in ready with many updates to enjoy. New tile...	3 beds \| 2 baths \| 1,456 sq.ft.	$318,000	Airbnb cash on cash: 5.29% Traditional cash on cash: 3.31% Airbnb Rental Income: $3164 Traditional Rental Income: $1857 Airbnb ROI: 5.29% Traditional ROI: 3.31%
415 S 9TH STREET Leesburg, FL Step into this stunning, century-old home that has been thoughtfully renovated, blending v...	3 beds \| 3 baths \| 1,757 sq.ft.	$421,500	Airbnb cash on cash: 4.25% Traditional cash on cash: 3.77% Airbnb Rental Income: $3164 Traditional Rental Income: $2258 Airbnb ROI: 4.25% Traditional ROI: 3.77%
1017 DUNDEE CIRCLE Leesburg, FL Welcome to 1017 Dundee Circle, a beautifully maintained 3-bedroom, 2-bathroom home in the ...	3 beds \| 2 baths \| 2,061 sq.ft.	$280,000	Airbnb cash on cash: 6.1% Traditional cash on cash: 6.45% Airbnb Rental Income: $3164 Traditional Rental Income: $2540 Airbnb ROI: 6.1% Traditional ROI: 6.45%
3681 ARLINGTON RIDGE BOULEVARD Leesburg, FL PRICED TO SELL! Golf-Front, Modern, Affordable Low-Maintenance Stucco Home built in 2018 L...	3 beds \| 2 baths \| 2,236 sq.ft.	$475,000	Airbnb cash on cash: 2.61% Traditional cash on cash: 2.46% Airbnb Rental Income: $3164 Traditional Rental Income: $2378 Airbnb ROI: 2.61% Traditional ROI: 2.46%
21708 ROYAL ST GEORGES LANE Leesburg, FL Auction Property. Royal Highlands a gated 55+ active community is ready for a new owner. ...	3 beds \| 2 baths \| 2,253 sq.ft.	$262,000	Airbnb cash on cash: 6.08% Traditional cash on cash: 4.81% Airbnb Rental Income: $3164 Traditional Rental Income: $2132 Airbnb ROI: 6.08% Traditional ROI: 4.81%
2202 OLD TAVARES ROAD Leesburg, FL Experience the perfect blend of space, privacy, and comfort in this custom-built estate ho...	4 beds \| 5 baths \| 3,337 sq.ft.	$635,000	Airbnb cash on cash: 4.32% Traditional cash on cash: 8.81% Airbnb Rental Income: $4837 Traditional Rental Income: $6506 Airbnb ROI: 4.32% Traditional ROI: 8.81%
3923 MANOR OAKS COURT Leesburg, FL Check out this stunning Trinidad Model located in Plantation at Leesburg, that offers 2 Be...	2 beds \| 2 baths \| 2,025 sq.ft.	$345,000	Airbnb cash on cash: 1.66% Traditional cash on cash: 2.87% Airbnb Rental Income: $1980 Traditional Rental Income: $1854 Airbnb ROI: 1.66% Traditional ROI: 2.87%
32525 OAK PARK DRIVE Leesburg, FL HONEY STOP THE CAR!!! It's so gorgeous!! We're pleased to present the opportunity to acqui...	2 beds \| 3 baths \| 1,643 sq.ft.	$285,000	Airbnb cash on cash: 2.18% Traditional cash on cash: 5.14% Airbnb Rental Income: $1980 Traditional Rental Income: $2257 Airbnb ROI: 2.18% Traditional ROI: 5.14%
4671 SPRING GROVE LANE Leesburg, FL Your Beautiful Home in the 55+ community at Arlington Ridge of Leesburg is Waiting! 2 Bedr...	2 beds \| 2 baths \| 1,558 sq.ft.	$319,900	Airbnb cash on cash: 1.27% Traditional cash on cash: 2.83% Airbnb Rental Income: $1980 Traditional Rental Income: $1932 Airbnb ROI: 1.27% Traditional ROI: 2.83%

Real Estate investment in Leesburg, FL

There are 310 properties for sale in the city of Leesburg . The median list price in Leesburg is $309,900 and the average price per square foot is $173. In September 2025, the average monthly cash on cash return in Leesburg is 4.00%. The average monthly rental income in Leesburg is $1,904.

Leesburg, FL Real Estate Investing: FAQs for Buyers, Sellers and Investors

There are 310 investment properties available for sale in Leesburg.

In 2025, the best neighborhood to buy investment property is Leesburg.

The ROI for Short-Term is higher than the Long-Term in Leesburg with average rental income of $3,164.

Your search for investment property begins and ends here

Investment Property for Sale in Leesburg, FL

6750 SUNNYSIDE DRIVE

Leesburg, FL

3 beds | 2 baths | 2,082 sq.ft.

$399,900

Airbnb cash on cash: 4.32%

Traditional cash on cash: 4.21%

Airbnb Rental Income: $3164

Traditional Rental Income: $2408

Airbnb ROI: 4.32%

Traditional ROI: 4.21%

25523 MAUREPAS LANE

Leesburg, FL

3 beds | 3 baths | 2,675 sq.ft.

$419,800

Airbnb cash on cash: 3.61%

Traditional cash on cash: 4.48%

Airbnb Rental Income: $3164

Traditional Rental Income: $2788

Airbnb ROI: 3.61%

Traditional ROI: 4.48%

26822 BULL RUN

Leesburg, FL

3 beds | 2 baths | 1,599 sq.ft.

$339,000

Airbnb cash on cash: 4.4%

Traditional cash on cash: 3.14%

Airbnb Rental Income: $3164

Traditional Rental Income: $2047

Airbnb ROI: 4.4%

Traditional ROI: 3.14%

24112 ROBINWOOD STREET

Leesburg, FL

2 beds | 2 baths | 2,071 sq.ft.

$375,000

Airbnb cash on cash: 1.8%

Traditional cash on cash: 3.68%

Airbnb Rental Income: $1980

Traditional Rental Income: $2122

Airbnb ROI: 1.8%

Traditional ROI: 3.68%

18 WESTON ROAD

Leesburg, FL

3 beds | 2 baths | 2,016 sq.ft.

$489,990

Airbnb cash on cash: 3.31%

Traditional cash on cash: 4.1%

Airbnb Rental Income: $3164

Traditional Rental Income: $2809

Airbnb ROI: 3.31%

Traditional ROI: 4.1%

4110 ARLINGTON RIDGE BOULEVARD

Leesburg, FL

4 beds | 2 baths | 1,857 sq.ft.

$389,900

Airbnb cash on cash: 7.88%

Traditional cash on cash: 3.43%

Airbnb Rental Income: $4837

Traditional Rental Income: $2216

Airbnb ROI: 7.88%

Traditional ROI: 3.43%

11114 LAKE EUSTIS DRIVE

Leesburg, FL

3 beds | 1 baths | 1,122 sq.ft.

$335,000

Airbnb cash on cash: 5.51%

Traditional cash on cash: 3.06%

Airbnb Rental Income: $3164

Traditional Rental Income: $1679

Airbnb ROI: 5.51%

Traditional ROI: 3.06%

25545 LAUREL VALLEY RD

Leesburg, FL

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

$349,900

Airbnb cash on cash: 1.61%

Traditional cash on cash: 3.82%

Airbnb Rental Income: $1980

Traditional Rental Income: $2187

Airbnb ROI: 1.61%