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
25523 MAUREPAS LANE Leesburg, FL Under contract-accepting backup offers. Expect to Be Charmed! Welcome to the classic Pando...	3 beds \| 3 baths \| 2,675 sq.ft.	$399,800	Airbnb cash on cash: 3.84% Traditional cash on cash: 4.75% Airbnb Rental Income: $3164 Traditional Rental Income: $2788 Airbnb ROI: 3.84% Traditional ROI: 4.75%
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 MOTIVATED SELLERS. ROOF 2025. HVAC 2024. WINDOWS 2024. The two-car Garage with a TANDEM AD...	2 beds \| 2 baths \| 2,071 sq.ft.	$359,000	Airbnb cash on cash: 1.92% Traditional cash on cash: 3.88% Airbnb Rental Income: $1980 Traditional Rental Income: $2122 Airbnb ROI: 1.92% Traditional ROI: 3.88%
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.	$469,990	Airbnb cash on cash: 3.5% Traditional cash on cash: 4.32% Airbnb Rental Income: $3164 Traditional Rental Income: $2809 Airbnb ROI: 3.5% Traditional ROI: 4.32%
4110 ARLINGTON RIDGE BOULEVARD Leesburg, FL Charming 4-Bedroom Home on the 17th Hole in Arlington Ridge â Privacy, Upgrades & Resort...	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%
543 COTTAGE PARK LANE Leesburg, FL Own this beautifully maintained cottage style home perfect for snowbirds or full-time resi...	2 beds \| 1 baths \| 788 sq.ft.	$170,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 5.09% Airbnb Rental Income: $1980 Traditional Rental Income: $1480 Airbnb ROI: 4.97% Traditional ROI: 5.09%
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%
3533 HUNTSVILLE LANE Leesburg, FL Popular Bird of Paradise Model in Prime Cul-de-Sac Location! Nestled in a quiet cul-de-sa...	2 beds \| 2 baths \| 2,426 sq.ft.	$344,000	Airbnb cash on cash: 1.2% Traditional cash on cash: 3.49% Airbnb Rental Income: $1980 Traditional Rental Income: $2200 Airbnb ROI: 1.2% Traditional ROI: 3.49%
4949 SAWGRASS LAKE CIRCLE Leesburg, FL Spacious and updated home offering 2,158 sq. ft. of comfortable living in the highly desir...	3 beds \| 3 baths \| 2,133 sq.ft.	$349,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 6.07% Airbnb Rental Income: $3164 Traditional Rental Income: $2807 Airbnb ROI: 4.98% Traditional ROI: 6.07%
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 Complete central heat and air replaced Sept. 2025, Affordable Modern 2 bedroom, 2 bath, Ma...	2 beds \| 2 baths \| 1,418 sq.ft.	$260,000	Airbnb cash on cash: 2.45% Traditional cash on cash: 4.85% Airbnb Rental Income: $1980 Traditional Rental Income: $2049 Airbnb ROI: 2.45% Traditional ROI: 4.85%
5318 FANTASY WAY Leesburg, FL Looking for a home thatâs been truly cared for and thoughtfully updated? This charming 3...	3 beds \| 2 baths \| 2,182 sq.ft.	$340,000	Airbnb cash on cash: 4.54% Traditional cash on cash: 3.9% Airbnb Rental Income: $3164 Traditional Rental Income: $2244 Airbnb ROI: 4.54% Traditional ROI: 3.9%
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.	$230,000	Airbnb cash on cash: 3.58% Traditional cash on cash: 5.46% Airbnb Rental Income: $1980 Traditional Rental Income: $1871 Airbnb ROI: 3.58% Traditional ROI: 5.46%
4513 ANTIETAM CREEK TRAIL Leesburg, FL Expect to be impressed! Welcome to 4513 Antietam Creek Trail, a 3 bedroom-3 bath home with...	3 beds \| 3 baths \| 2,138 sq.ft.	$444,900	Airbnb cash on cash: 2.73% Traditional cash on cash: 3.13% Airbnb Rental Income: $3164 Traditional Rental Income: $2615 Airbnb ROI: 2.73% Traditional ROI: 3.13%
109 N OAKLAND STREET Leesburg, FL This charming property at 109 N Oakland Street offers a prime location just steps from his...	3 beds \| 2 baths \| 1,512 sq.ft.	$249,900	Airbnb cash on cash: 7.84% Traditional cash on cash: 6.68% Airbnb Rental Income: $3164 Traditional Rental Income: $2174 Airbnb ROI: 7.84% Traditional ROI: 6.68%
506 PERKINS STREET Leesburg, FL Under contract-accepting backup offers. LOCATION, LOCATION, LOCATION! SOOO many possibili...	3 beds \| 2 baths \| 1,972 sq.ft.	$287,000	Airbnb cash on cash: 6.76% Traditional cash on cash: 10.95% Airbnb Rental Income: $3164 Traditional Rental Income: $3580 Airbnb ROI: 6.76% Traditional ROI: 10.95%
10323 JOANIES RUN Leesburg, FL Welcome to this move-in-ready Silver Lake Area home on a beautiful treed lot with a huge f...	3 beds \| 2 baths \| 1,630 sq.ft.	$309,000	Airbnb cash on cash: 6.26% Traditional cash on cash: 4.73% Airbnb Rental Income: $3164 Traditional Rental Income: $2003 Airbnb ROI: 6.26% Traditional ROI: 4.73%
26126 NEWCOMBE CIRCLE Leesburg, FL Extremely Well Maintained Lake Highlands 55+ Community 3 bedroom, 2 bath home - don't miss...	3 beds \| 2 baths \| 1,890 sq.ft.	$299,900	Airbnb cash on cash: 5.5% Traditional cash on cash: 5.16% Airbnb Rental Income: $3164 Traditional Rental Income: $2353 Airbnb ROI: 5.5% Traditional ROI: 5.16%
1906 ANGEL FISH LOOP Leesburg, FL Attention investors. Here is your next project and just reduced. Modern Comfort with a Spl...	3 beds \| 2 baths \| 2,035 sq.ft.	$324,000	Airbnb cash on cash: 5.9% Traditional cash on cash: 6.51% Airbnb Rental Income: $3164 Traditional Rental Income: $2635 Airbnb ROI: 5.9% Traditional ROI: 6.51%
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%
26939 WHITE PLAINS WAY Leesburg, FL Enjoy maintenance-free living in this spacious 2-bedroom, 2-bath villa located in the high...	2 beds \| 2 baths \| 1,631 sq.ft.	$315,000	Airbnb cash on cash: 0.52% Traditional cash on cash: 2.98% Airbnb Rental Income: $1980 Traditional Rental Income: $2192 Airbnb ROI: 0.52% Traditional ROI: 2.98%
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%
4002 RICHMOND CROSSING Leesburg, FL Welcome to 4002 Richmond Crossing, a beautifully maintained 3-bedroom, 2-bathroom home nes...	3 beds \| 2 baths \| 2,188 sq.ft.	$423,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 2.56% Airbnb Rental Income: $3164 Traditional Rental Income: $2354 Airbnb ROI: 2.8% Traditional ROI: 2.56%
11802 OCKLAWAHA DRIVE Leesburg, FL Under contract-accepting backup offers. One or more photo(s) has been virtually staged. We...	3 beds \| 2 baths \| 1,176 sq.ft.	$240,000	Airbnb cash on cash: 8.25% Traditional cash on cash: 5.05% Airbnb Rental Income: $3164 Traditional Rental Income: $1722 Airbnb ROI: 8.25% Traditional ROI: 5.05%
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.	$329,900	Airbnb cash on cash: 5.52% Traditional cash on cash: 4.95% Airbnb Rental Income: $3164 Traditional Rental Income: $2272 Airbnb ROI: 5.52% Traditional ROI: 4.95%
5135 AURORA DRIVE Leesburg, FL Amazingly nice custom Savannah/Scarsborough model in desirable Legacy of Leesburg. This im...	3 beds \| 2 baths \| 2,055 sq.ft.	$349,900	Airbnb cash on cash: 3.73% Traditional cash on cash: 3.45% Airbnb Rental Income: $3164 Traditional Rental Income: $2357 Airbnb ROI: 3.73% Traditional ROI: 3.45%
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.	$350,000	Airbnb cash on cash: 5.42% Traditional cash on cash: 4.51% Airbnb Rental Income: $3164 Traditional Rental Income: $2149 Airbnb ROI: 5.42% Traditional ROI: 4.51%
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.	$305,000	Airbnb cash on cash: 6.01% Traditional cash on cash: 4.66% Airbnb Rental Income: $3164 Traditional Rental Income: $2059 Airbnb ROI: 6.01% Traditional ROI: 4.66%
259 KELOU COURT Leesburg, FL Charming 2-Bedroom Home with Co-op Share in Active 55+ Community! Welcome to your slice of...	2 beds \| 2 baths \| 1,056 sq.ft.	$113,000	Airbnb cash on cash: 8.44% Traditional cash on cash: 9.06% Airbnb Rental Income: $1980 Traditional Rental Income: $1528 Airbnb ROI: 8.44% Traditional ROI: 9.06%
5712 SUMMERBROOKE COURT Leesburg, FL Assumable VA Loan with an interest Rate of 2.75%. This charming home offers a stunning wat...	3 beds \| 3 baths \| 2,961 sq.ft.	$599,900	Airbnb cash on cash: 1.94% Traditional cash on cash: 3.41% Airbnb Rental Income: $3164 Traditional Rental Income: $3269 Airbnb ROI: 1.94% Traditional ROI: 3.41%
5126 CHANTICLEER DRIVE Leesburg, FL Under contract-accepting backup offers. Welcome to your private retreat in the heart of th...	2 beds \| 2 baths \| 2,124 sq.ft.	$439,000	Airbnb cash on cash: 1.06% Traditional cash on cash: 3.56% Airbnb Rental Income: $1980 Traditional Rental Income: $2486 Airbnb ROI: 1.06% Traditional ROI: 3.56%
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 They don't build them like this anymore!! Come Take a look at this stunning home with an e...	3 beds \| 2 baths \| 1,904 sq.ft.	$465,850	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%
27106 CAMERONS RUN Leesburg, FL Priced reduced! Seller offering $7,500 in concessions towards closing costs! Home has a NE...	3 beds \| 2 baths \| 2,436 sq.ft.	$449,900	Airbnb cash on cash: 3.2% Traditional cash on cash: 3.25% Airbnb Rental Income: $3164 Traditional Rental Income: $2466 Airbnb ROI: 3.2% Traditional ROI: 3.25%
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.	$315,900	Airbnb cash on cash: 5.33% Traditional cash on cash: 3.34% Airbnb Rental Income: $3164 Traditional Rental Income: $1857 Airbnb ROI: 5.33% Traditional ROI: 3.34%
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%
918 DUNDEE CIRCLE Leesburg, FL Welcome to 918 Dundee Circle â a charming and well-maintained home in the sought-after S...	2 beds \| 2 baths \| 1,380 sq.ft.	$245,000	Airbnb cash on cash: 2.74% Traditional cash on cash: 4.74% Airbnb Rental Income: $1980 Traditional Rental Income: $1923 Airbnb ROI: 2.74% Traditional ROI: 4.74%
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.	$600,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 9.38% Airbnb Rental Income: $4837 Traditional Rental Income: $6506 Airbnb ROI: 4.63% Traditional ROI: 9.38%

Real Estate investment in Leesburg, FL

There are 320 properties for sale in the city of Leesburg . The median list price in Leesburg is $299,900 and the average price per square foot is $170. In October 2025, the average monthly cash on cash return in Leesburg is 4.00%. The average monthly rental income in Leesburg is $1,911.

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

There are 320 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 $1,980.

Your search for investment property begins and ends here

Investment Property for Sale in Leesburg, FL

25523 MAUREPAS LANE

Leesburg, FL

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

$399,800

Airbnb cash on cash: 3.84%

Traditional cash on cash: 4.75%

Airbnb Rental Income: $3164

Traditional Rental Income: $2788

Airbnb ROI: 3.84%

Traditional ROI: 4.75%

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.

$359,000

Airbnb cash on cash: 1.92%

Traditional cash on cash: 3.88%

Airbnb Rental Income: $1980

Traditional Rental Income: $2122

Airbnb ROI: 1.92%

Traditional ROI: 3.88%

18 WESTON ROAD

Leesburg, FL

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

$469,990

Airbnb cash on cash: 3.5%

Traditional cash on cash: 4.32%

Airbnb Rental Income: $3164

Traditional Rental Income: $2809

Airbnb ROI: 3.5%

Traditional ROI: 4.32%

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%

543 COTTAGE PARK LANE

Leesburg, FL

2 beds | 1 baths | 788 sq.ft.

$170,000

Airbnb cash on cash: 4.97%

Traditional cash on cash: 5.09%

Airbnb Rental Income: $1980

Traditional Rental Income: $1480

Airbnb ROI: 4.97%

Traditional ROI: 5.09%

416 HANCOCK ROAD

Leesburg, FL

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%

3533 HUNTSVILLE LANE

Leesburg, FL

2 beds | 2 baths | 2,426 sq.ft.

$344,000

Airbnb cash on cash: 1.2%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $1980

Traditional Rental Income: $2200

Airbnb ROI: 1.2%