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
1117 BEN HOPE Drive Leesburg, FL Welcome to the largest home in the desirable 55+ community Scottish Highlands! Stepping th...	2 beds \| 3 baths \| 2,280 sq.ft.	$325,000	Airbnb cash on cash: -0.66% Traditional cash on cash: 5.48% Airbnb Rental Income: $1121 Traditional Rental Income: $2623 Airbnb ROI: -0.66% Traditional ROI: 5.48%
18 WESTON Road Leesburg, FL REDUCED OVER $89,000 -- NOW $399,990! Offered at a dramatically reduced price, this waterf...	3 beds \| 2 baths \| 2,016 sq.ft.	$399,990	Airbnb cash on cash: 3.05% Traditional cash on cash: 5.27% Airbnb Rental Income: $2597 Traditional Rental Income: $2809 Airbnb ROI: 3.05% Traditional ROI: 5.27%
7247 TREASURE ISLAND Road Leesburg, FL PRICE IMPROVEMENT! MOTIVATED SELLER! Waterfront living on the Harris Chain of Lakes! Welco...	3 beds \| 2 baths \| 2,156 sq.ft.	$380,000	Airbnb cash on cash: 3.2% Traditional cash on cash: 5.96% Airbnb Rental Income: $2597 Traditional Rental Income: $2959 Airbnb ROI: 3.2% Traditional ROI: 5.96%
4967 HERON RUN Circle Leesburg, FL This two bedroom,2 two bath, 1.5 car garage home with an enclosed lanai has a FULLY FENCED...	2 beds \| 2 baths \| 1,119 sq.ft.	$229,900	Airbnb cash on cash: -0.32% Traditional cash on cash: 3.95% Airbnb Rental Income: $1121 Traditional Rental Income: $1674 Airbnb ROI: -0.32% Traditional ROI: 3.95%
4110 ARLINGTON RIDGE Boulevard Leesburg, FL Wake up each morning to the peaceful sounds of birds singing as you sip your coffee on the...	3 beds \| 2 baths \| 1,857 sq.ft.	$369,000	Airbnb cash on cash: 2.24% Traditional cash on cash: 3.69% Airbnb Rental Income: $2597 Traditional Rental Income: $2478 Airbnb ROI: 2.24% Traditional ROI: 3.69%
26868 WHITE PLAINS Way Leesburg, FL Spectacular Golf View from the Tee Boxes to the Green and pond from 400 square ft tiled, c...	4 beds \| 2 baths \| 1,877 sq.ft.	$337,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 4.4% Airbnb Rental Income: $3292 Traditional Rental Income: $2219 Airbnb ROI: 5.46% Traditional ROI: 4.4%
33450 IRONGATE Drive Leesburg, FL Virtually Staged. 33450 Irongate Dr is a single-story Leesburg home with three bedrooms an...	3 beds \| 2 baths \| 1,364 sq.ft.	$257,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 5% Airbnb Rental Income: $2597 Traditional Rental Income: $1863 Airbnb ROI: 5.46% Traditional ROI: 5%
20512 QUEEN ALEXANDRA Drive Leesburg, FL Beautifully updated Edinburgh model in the sought-after 55+ community of Royal Highlands, ...	3 beds \| 2 baths \| 2,008 sq.ft.	$345,000	Airbnb cash on cash: 3.34% Traditional cash on cash: 4.05% Airbnb Rental Income: $2597 Traditional Rental Income: $2206 Airbnb ROI: 3.34% Traditional ROI: 4.05%
5133 LINKS Lane Leesburg, FL Welcome home to this lovely 3 Bed 2 Bath home in your Gated, Golf Community of Royal Highl...	3 beds \| 2 baths \| 1,701 sq.ft.	$269,900	Airbnb cash on cash: 3.88% Traditional cash on cash: 5.42% Airbnb Rental Income: $2597 Traditional Rental Income: $2367 Airbnb ROI: 3.88% Traditional ROI: 5.42%
21811 KING HENRY Avenue Leesburg, FL Step into easy Florida living with this well-maintained Squire floor plan, where thoughtfu...	3 beds \| 2 baths \| 1,918 sq.ft.	$334,900	Airbnb cash on cash: 3.32% Traditional cash on cash: 5.01% Airbnb Rental Income: $2597 Traditional Rental Income: $2508 Airbnb ROI: 3.32% Traditional ROI: 5.01%
416 HANCOCK Road Leesburg, FL LAKEFRONT DREAM HOME ON LAKE GRIFFIN with NEW CUSTOM SCREENED IN $250K BOATHOUSE with high...	3 beds \| 4 baths \| 3,207 sq.ft.	$990,000	Airbnb cash on cash: 0.04% Traditional cash on cash: 6.02% Airbnb Rental Income: $2597 Traditional Rental Income: $7481 Airbnb ROI: 0.04% Traditional ROI: 6.02%
9916 JACKSON Road Leesburg, FL POOL HOME ON NEARLY HALF AN ACRE WITH NO HOA! Welcome to this spacious 3-bedroom, 2.5-bath...	3 beds \| 3 baths \| 2,496 sq.ft.	$383,000	Airbnb cash on cash: 2.93% Traditional cash on cash: 6.8% Airbnb Rental Income: $2597 Traditional Rental Income: $3366 Airbnb ROI: 2.93% Traditional ROI: 6.8%
26951 WHITE PLAINS Way Leesburg, FL Welcome to this inviting 2-bedroom, 2-bath villa in the desirable gated community of Arlin...	2 beds \| 2 baths \| 1,418 sq.ft.	$259,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 5.61% Airbnb Rental Income: $1121 Traditional Rental Income: $2230 Airbnb ROI: -0.47% Traditional ROI: 5.61%
100 E OAK TERRACE Drive #A2 Leesburg, FL *Seller is willing to provide up to $10,000 in concessions* The open-concept living ar...	2 beds \| 2 baths \| 1,518 sq.ft.	$145,000	Airbnb cash on cash: -1.6% Traditional cash on cash: 4.89% Airbnb Rental Income: $1121 Traditional Rental Income: $1647 Airbnb ROI: -1.6% Traditional ROI: 4.89%
1361 PETERS Drive Leesburg, FL Virtually Staged. WELCOME HOME! This beautifully maintained 3-bedroom, 1.5-bath home offer...	3 beds \| 2 baths \| 1,301 sq.ft.	$284,990	Airbnb cash on cash: 4.67% Traditional cash on cash: 5.38% Airbnb Rental Income: $2597 Traditional Rental Income: $2167 Airbnb ROI: 4.67% Traditional ROI: 5.38%
35045 SWEET LEAF Lane Leesburg, FL Beautiful former model home located in the desirable Bentwood Subdivision in Lake County, ...	4 beds \| 2 baths \| 1,846 sq.ft.	$335,000	Airbnb cash on cash: 5.97% Traditional cash on cash: 5.75% Airbnb Rental Income: $3292 Traditional Rental Income: $2485 Airbnb ROI: 5.97% Traditional ROI: 5.75%
11637 LAKE Drive Leesburg, FL PRICE IMPROVEMENT on this beautifully remodeled Leesburg home sitting on a rare, fully fen...	3 beds \| 2 baths \| 1,898 sq.ft.	$339,900	Airbnb cash on cash: 3.86% Traditional cash on cash: 5.42% Airbnb Rental Income: $2597 Traditional Rental Income: $2473 Airbnb ROI: 3.86% Traditional ROI: 5.42%
25034 BETTON Hill Leesburg, FL Attention investors! Discover the potential in this well-located home nestled within a sou...	2 beds \| 2 baths \| 1,456 sq.ft.	$129,000	Airbnb cash on cash: 1.71% Traditional cash on cash: 9.94% Airbnb Rental Income: $1250 Traditional Rental Income: $1874 Airbnb ROI: 1.71% Traditional ROI: 9.94%
33137 IRONGATE Drive Leesburg, FL Virtually Staged. 33137 Irongate Dr is a one-story Leesburg home built in 2018 with an ope...	3 beds \| 2 baths \| 1,504 sq.ft.	$269,000	Airbnb cash on cash: 5.03% Traditional cash on cash: 5.25% Airbnb Rental Income: $2597 Traditional Rental Income: $2032 Airbnb ROI: 5.03% Traditional ROI: 5.25%
25501 MAUREPAS Lane Leesburg, FL MAJOR PRICE IMPROVEMENT! Come check out this ONE OF A KIND HOME for you in the sought afte...	3 beds \| 2 baths \| 2,945 sq.ft.	$465,000	Airbnb cash on cash: 1.85% Traditional cash on cash: 3.1% Airbnb Rental Income: $2597 Traditional Rental Income: $2519 Airbnb ROI: 1.85% Traditional ROI: 3.1%
30437 ORANGE Drive Leesburg, FL Welcome to this beautifully renovated 3-bedroom, 2-bathroom lakefront home with a detached...	4 beds \| 3 baths \| 2,665 sq.ft.	$800,000	Airbnb cash on cash: 1.53% Traditional cash on cash: 3.62% Airbnb Rental Income: $3292 Traditional Rental Income: $4110 Airbnb ROI: 1.53% Traditional ROI: 3.62%
5350 ASTOR Street Leesburg, FL Welcome to 5350 Astor Street, a charming 2-bedroom, 2-bath home nestled on a desirable cor...	2 beds \| 2 baths \| 1,665 sq.ft.	$264,900	Airbnb cash on cash: 0.19% Traditional cash on cash: 6.02% Airbnb Rental Income: $1121 Traditional Rental Income: $2202 Airbnb ROI: 0.19% Traditional ROI: 6.02%
1611 INDIAN Trail Leesburg, FL Investor opportunity in Leesburg, Florida. This fully rented single-family property offers...	6 beds \| 3 baths \| 1,454 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 5.09% Airbnb Rental Income: $null Traditional Rental Income: $2699 Airbnb ROI: N/A Traditional ROI: 5.09%
1712 W MAIN Street Leesburg, FL Virtually Staged. Virtually Staged. Check out this 2-Bedroom, 1.5 Bath home. This home is ...	2 beds \| 2 baths \| 884 sq.ft.	$215,000	Airbnb cash on cash: 1.22% Traditional cash on cash: 6.23% Airbnb Rental Income: $1121 Traditional Rental Income: $1764 Airbnb ROI: 1.22% Traditional ROI: 6.23%
1337 LEE Court Leesburg, FL Welcome to this fully remodeled 3-bedroom, 2-bath single-family home offering 1,392 square...	3 beds \| 2 baths \| 1,392 sq.ft.	$299,900	Airbnb cash on cash: 4.61% Traditional cash on cash: 5.9% Airbnb Rental Income: $2597 Traditional Rental Income: $2341 Airbnb ROI: 4.61% Traditional ROI: 5.9%
5712 SUMMERBROOKE Court Leesburg, FL Welcome to waterfront living at its finest in the highly sought-after, gated community of ...	3 beds \| 3 baths \| 2,961 sq.ft.	$525,000	Airbnb cash on cash: 1.34% Traditional cash on cash: 4.21% Airbnb Rental Income: $2597 Traditional Rental Income: $3384 Airbnb ROI: 1.34% Traditional ROI: 4.21%
25800 BELLE HELENE Leesburg, FL NEW 2026 ROOF SCHEDULED BEFORE CLOSING This home sits on a Large Corner Lot in The Plant...	3 beds \| 2 baths \| 1,653 sq.ft.	$228,000	Airbnb cash on cash: 5.59% Traditional cash on cash: 7.53% Airbnb Rental Income: $2597 Traditional Rental Income: $2395 Airbnb ROI: 5.59% Traditional ROI: 7.53%
12020 VIRGINIA Drive Leesburg, FL Escape the hustle without sacrificing convenience! This adorable and newer one-story home ...	3 beds \| 2 baths \| 1,191 sq.ft.	$295,000	Airbnb cash on cash: 4.46% Traditional cash on cash: 3.82% Airbnb Rental Income: $2597 Traditional Rental Income: $1796 Airbnb ROI: 4.46% Traditional ROI: 3.82%
21725 KING RICHARDS Way Leesburg, FL Conservation lot! Beautifully updated and truly move-in ready, this exceptional 3-bedroom,...	3 beds \| 2 baths \| 1,630 sq.ft.	$295,000	Airbnb cash on cash: 4.02% Traditional cash on cash: 4.24% Airbnb Rental Income: $2597 Traditional Rental Income: $2035 Airbnb ROI: 4.02% Traditional ROI: 4.24%
27106 CAMERONS Run Leesburg, FL Price Reduced! NEW ROOF! This beautifully landscaped property offers a 3-bedroom, 2-bath s...	3 beds \| 2 baths \| 2,436 sq.ft.	$419,900	Airbnb cash on cash: 2.3% Traditional cash on cash: 4.03% Airbnb Rental Income: $2597 Traditional Rental Income: $2656 Airbnb ROI: 2.3% Traditional ROI: 4.03%
26617 OTTER CREEK Lane Leesburg, FL NEW PRICE!! Price reduced and sellers are motivated! Welcome to this beautifully maintaine...	4 beds \| 3 baths \| 2,580 sq.ft.	$499,900	Airbnb cash on cash: 2.43% Traditional cash on cash: 3.44% Airbnb Rental Income: $3292 Traditional Rental Income: $3025 Airbnb ROI: 2.43% Traditional ROI: 3.44%
32730 BLOSSOM Lane Leesburg, FL JUST REDUCED $10K!!! Move-In Ready 4 Bedroom 2 Bathroom Home on a Nice Lot Located in the ...	4 beds \| 2 baths \| 1,248 sq.ft.	$214,900	Airbnb cash on cash: 9.58% Traditional cash on cash: 5.89% Airbnb Rental Income: $3292 Traditional Rental Income: $1802 Airbnb ROI: 9.58% Traditional ROI: 5.89%

Real Estate investment in Leesburg, FL

There are 343 properties for sale in the city of Leesburg . The median list price in Leesburg is $307,541 and the average price per square foot is $188. In October 2026, the average monthly cash on cash return in Leesburg is 5.00%. The average monthly rental income in Leesburg is $1,822.

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

There are 343 investment properties available for sale in Leesburg.

In 2026, the best neighborhood to buy investment property is Leesburg.

The ROI for Long-Term is higher than the Short-Term in Leesburg with average rental income of $1,822.

Your search for investment property begins and ends here

Investment Property for Sale in Leesburg, FL

1117 BEN HOPE Drive

Leesburg, FL

2 beds | 3 baths | 2,280 sq.ft.

$325,000

Airbnb cash on cash: -0.66%

Traditional cash on cash: 5.48%

Airbnb Rental Income: $1121

Traditional Rental Income: $2623

Airbnb ROI: -0.66%

Traditional ROI: 5.48%

18 WESTON Road

Leesburg, FL

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

$399,990

Airbnb cash on cash: 3.05%

Traditional cash on cash: 5.27%

Airbnb Rental Income: $2597

Traditional Rental Income: $2809

Airbnb ROI: 3.05%

Traditional ROI: 5.27%

7247 TREASURE ISLAND Road

Leesburg, FL

3 beds | 2 baths | 2,156 sq.ft.

$380,000

Airbnb cash on cash: 3.2%

Traditional cash on cash: 5.96%

Airbnb Rental Income: $2597

Traditional Rental Income: $2959

Airbnb ROI: 3.2%

Traditional ROI: 5.96%

4967 HERON RUN Circle

Leesburg, FL

2 beds | 2 baths | 1,119 sq.ft.

$229,900

Airbnb cash on cash: -0.32%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1121

Traditional Rental Income: $1674

Airbnb ROI: -0.32%

Traditional ROI: 3.95%

4110 ARLINGTON RIDGE Boulevard

Leesburg, FL

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

$369,000

Airbnb cash on cash: 2.24%

Traditional cash on cash: 3.69%

Airbnb Rental Income: $2597

Traditional Rental Income: $2478

Airbnb ROI: 2.24%

Traditional ROI: 3.69%

26868 WHITE PLAINS Way

Leesburg, FL

4 beds | 2 baths | 1,877 sq.ft.

$337,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 4.4%

Airbnb Rental Income: $3292

Traditional Rental Income: $2219

Airbnb ROI: 5.46%

Traditional ROI: 4.4%

33450 IRONGATE Drive

Leesburg, FL

3 beds | 2 baths | 1,364 sq.ft.

$257,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 5%

Airbnb Rental Income: $2597

Traditional Rental Income: $1863

Airbnb ROI: 5.46%

Traditional ROI: 5%

20512 QUEEN ALEXANDRA Drive

Leesburg, FL

3 beds | 2 baths | 2,008 sq.ft.

$345,000

Airbnb cash on cash: 3.34%

Traditional cash on cash: 4.05%

Airbnb Rental Income: $2597

Traditional Rental Income: $2206

Airbnb ROI: 3.34%