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
5552 KING JAMES AVENUE Leesburg, FL TRULY A MUST SEE SINGLE-STORY CBS HOME located in the desirable 55+ GATED COMMUNITY of Roy...	3 beds \| 2 baths \| 1,469 sq.ft.	$282,000	Airbnb cash on cash: 6.14% Traditional cash on cash: 4.04% Airbnb Rental Income: $3164 Traditional Rental Income: $1891 Airbnb ROI: 6.14% Traditional ROI: 4.04%
26822 BULL RUN Leesburg, FL Exceptional view from one of the top lots in the entire community. It is open at the rear ...	3 beds \| 2 baths \| 1,602 sq.ft.	$329,000	Airbnb cash on cash: 4.51% Traditional cash on cash: 3.21% Airbnb Rental Income: $3164 Traditional Rental Income: $2047 Airbnb ROI: 4.51% Traditional ROI: 3.21%
24112 ROBINWOOD STREET Leesburg, FL Motivated Sellers. Roof 2025. HVAC 2025. Windows 2022. This meticulously-kept home is move...	2 beds \| 2 baths \| 2,071 sq.ft.	$359,000	Airbnb cash on cash: 1.74% Traditional cash on cash: 3.7% Airbnb Rental Income: $1980 Traditional Rental Income: $2122 Airbnb ROI: 1.74% Traditional ROI: 3.7%
4110 ARLINGTON RIDGE BOULEVARD Leesburg, FL PRICE CHANGE! Charming 3-Bedroom Home plus office on the 17th Hole in Arlington Ridge â ...	3 beds \| 2 baths \| 1,857 sq.ft.	$385,000	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.49% Airbnb Rental Income: $3164 Traditional Rental Income: $2216 Airbnb ROI: 4.13% Traditional ROI: 3.49%
33651 OVERTON DRIVE Leesburg, FL New Price Adjustment, Home is ready to move in! Spacious Leesburg home with Resort-Style ...	3 beds \| 4 baths \| 3,006 sq.ft.	$520,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 2.68% Airbnb Rental Income: $3164 Traditional Rental Income: $2377 Airbnb ROI: 2.83% Traditional ROI: 2.68%
33719 OVERTON DRIVE Leesburg, FL WATERFRONT POOL HOME WITH NO HOA. Imagine stepping into your own slice of paradise in the ...	4 beds \| 3 baths \| 2,340 sq.ft.	$437,500	Airbnb cash on cash: 7.83% Traditional cash on cash: 7.11% Airbnb Rental Income: $5065 Traditional Rental Income: $3737 Airbnb ROI: 7.83% Traditional ROI: 7.11%
3605 MOUNT HOPE LOOP Leesburg, FL Stunning Grand Cypress in Glendale Village â a beautifully maintained lawn-care communit...	2 beds \| 2 baths \| 1,868 sq.ft.	$325,000	Airbnb cash on cash: 2.58% Traditional cash on cash: 4.08% Airbnb Rental Income: $1980 Traditional Rental Income: $1919 Airbnb ROI: 2.58% Traditional ROI: 4.08%
41041 WHILDEN LANE Leesburg, FL Price Improvement! Mini-Ranch / Mini-Farm â 5 Bedroom / 3 Bath Country Home on Nearly 10...	5 beds \| 3 baths \| 2,768 sq.ft.	$480,500	Airbnb cash on cash: N/A Traditional cash on cash: 5.62% Airbnb Rental Income: $null Traditional Rental Income: $3386 Airbnb ROI: N/A Traditional ROI: 5.62%
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.	$289,900	Airbnb cash on cash: 5.28% Traditional cash on cash: 4.17% Airbnb Rental Income: $3164 Traditional Rental Income: $2145 Airbnb ROI: 5.28% Traditional ROI: 4.17%
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.	$1,250,000	Airbnb cash on cash: 0.23% Traditional cash on cash: 3.45% Airbnb Rental Income: $3164 Traditional Rental Income: $6189 Airbnb ROI: 0.23% Traditional ROI: 3.45%
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.	$336,900	Airbnb cash on cash: 5.21% Traditional cash on cash: 6.34% Airbnb Rental Income: $3164 Traditional Rental Income: $2807 Airbnb ROI: 5.21% Traditional ROI: 6.34%
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.	$365,000	Airbnb cash on cash: 3.76% Traditional cash on cash: 2.5% Airbnb Rental Income: $3164 Traditional Rental Income: $2016 Airbnb ROI: 3.76% Traditional ROI: 2.5%
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%
4553 BELLE GROVE Leesburg, FL Under contract-accepting backup offers. A VA assumable mortgage at just 2.8% makes this ho...	2 beds \| 2 baths \| 1,420 sq.ft.	$198,000	Airbnb cash on cash: 4.3% Traditional cash on cash: 6.48% Airbnb Rental Income: $1980 Traditional Rental Income: $1871 Airbnb ROI: 4.3% Traditional ROI: 6.48%
4513 ANTIETAM CREEK TRAIL Leesburg, FL Expect to be impressed! PRICE IMPROVEMENT! Welcome to 4513 Antietam Creek Trail, a 3 bedro...	3 beds \| 3 baths \| 2,138 sq.ft.	$439,777	Airbnb cash on cash: 2.77% Traditional cash on cash: 3.18% Airbnb Rental Income: $3164 Traditional Rental Income: $2615 Airbnb ROI: 2.77% Traditional ROI: 3.18%
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.	$242,400	Airbnb cash on cash: 8.11% Traditional cash on cash: 6.91% Airbnb Rental Income: $3164 Traditional Rental Income: $2174 Airbnb ROI: 8.11% Traditional ROI: 6.91%
10323 JOANIES RUN Leesburg, FL Under contract-accepting backup offers. Welcome to this move-in-ready Silver Lake Area hom...	3 beds \| 2 baths \| 1,630 sq.ft.	$300,000	Airbnb cash on cash: 6.47% Traditional cash on cash: 4.89% Airbnb Rental Income: $3164 Traditional Rental Income: $2003 Airbnb ROI: 6.47% Traditional ROI: 4.89%
1108 LEE STREET Leesburg, FL Discover your ultimate Florida oasis in this stunning 3-bedroom, 2-bathroom POOL home, bri...	3 beds \| 2 baths \| 1,404 sq.ft.	$249,900	Airbnb cash on cash: 7.63% Traditional cash on cash: 7% Airbnb Rental Income: $3164 Traditional Rental Income: $2299 Airbnb ROI: 7.63% Traditional ROI: 7%
35043 SILVER OAK DRIVE Leesburg, FL Quiet street, fenced yard and screened pool area makes for a great home to raise your fami...	3 beds \| 3 baths \| 2,312 sq.ft.	$435,000	Airbnb cash on cash: 3.93% Traditional cash on cash: 5.3% Airbnb Rental Income: $3164 Traditional Rental Income: $3004 Airbnb ROI: 3.93% Traditional ROI: 5.3%
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%
25501 MAUREPAS LANE Leesburg, FL RARE FIND!! EXPECT TO BE IMPRESSED!! PREMIUM LOT!! NO REAR NEIGHBORS & PANORAMIC VIEWS!...	2 beds \| 2 baths \| 2,945 sq.ft.	$569,900	Airbnb cash on cash: 0.36% Traditional cash on cash: 1.86% Airbnb Rental Income: $1980 Traditional Rental Income: $2259 Airbnb ROI: 0.36% Traditional ROI: 1.86%
500 NEWELL HILL ROAD #106D Leesburg, FL New Roof!! Welcome to this cozy and well-maintained 2-bedroom, 2-bath condo located in a ...	2 beds \| 2 baths \| 1,134 sq.ft.	$80,000	Airbnb cash on cash: 2.83% Traditional cash on cash: 4% Airbnb Rental Income: $1980 Traditional Rental Income: $1553 Airbnb ROI: 2.83% Traditional ROI: 4%
1611 INDIAN TRAIL Leesburg, FL Investor opportunity in Leesburg, Florida. This fully rented single-family property offers...	3 beds \| 2 baths \| 1,454 sq.ft.	$450,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.88% Airbnb Rental Income: $null Traditional Rental Income: $2330 Airbnb ROI: N/A Traditional ROI: 3.88%
3722 ARLINGTON RIDGE BOULEVARD Leesburg, FL Welcome to a life that feels like vacation every day. Nestled in one of Central Floridaâ...	3 beds \| 2 baths \| 1,710 sq.ft.	$350,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 4.06% Airbnb Rental Income: $3164 Traditional Rental Income: $2147 Airbnb ROI: 4.97% Traditional ROI: 4.06%
5000 LONG MEADOW DRIVE Leesburg, FL 5000 Long Meadow Drive offers a beautifully maintained residence with numerous high-end up...	3 beds \| 3 baths \| 1,954 sq.ft.	$474,000	Airbnb cash on cash: 3% Traditional cash on cash: 2.99% Airbnb Rental Income: $3164 Traditional Rental Income: $2445 Airbnb ROI: 3% Traditional ROI: 2.99%
5135 AURORA DRIVE Leesburg, FL Stunning Custom Savannah/Scarsborough Model in the Sought-After Legacy of Leesburg Communi...	3 beds \| 2 baths \| 2,055 sq.ft.	$344,900	Airbnb cash on cash: 3.8% Traditional cash on cash: 3.52% Airbnb Rental Income: $3164 Traditional Rental Income: $2357 Airbnb ROI: 3.8% Traditional ROI: 3.52%
1605 SELKIRK DRIVE Leesburg, FL Life feels easier and more peaceful in this 2-bedroom, 2-bath home set within a quiet 55+ ...	2 beds \| 2 baths \| 1,284 sq.ft.	$215,000	Airbnb cash on cash: 3.4% Traditional cash on cash: 5.1% Airbnb Rental Income: $1980 Traditional Rental Income: $1809 Airbnb ROI: 3.4% Traditional ROI: 5.1%
5610 KING JAMES AVENUE Leesburg, FL COMPLETELY REFRESHED - NEW ROOF JUST COMPLETED, Move-In Ready. This 3-bedroom, 2-bath Topa...	3 beds \| 2 baths \| 1,606 sq.ft.	$239,900	Airbnb cash on cash: 7.67% Traditional cash on cash: 6.01% Airbnb Rental Income: $3164 Traditional Rental Income: $2072 Airbnb ROI: 7.67% Traditional ROI: 6.01%
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.	$284,000	Airbnb cash on cash: 6.52% Traditional cash on cash: 5.07% Airbnb Rental Income: $3164 Traditional Rental Income: $2059 Airbnb ROI: 6.52% Traditional ROI: 5.07%
16 EASTER ROSS COURT Leesburg, FL Discover the perfect blend of comfort, convenience, and Florida charm in this beautifully ...	2 beds \| 2 baths \| 1,418 sq.ft.	$215,000	Airbnb cash on cash: 3.35% Traditional cash on cash: 5.53% Airbnb Rental Income: $1980 Traditional Rental Income: $1906 Airbnb ROI: 3.35% Traditional ROI: 5.53%
259 KELOU COURT Leesburg, FL MOTIVATED SELLER! Affordable 55+ Living with Co-Op Share â No Lot Rent & Resort-Style Am...	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 Major Price Reduction and Seller is Motivated and will look at all offers. Don't be afrai...	3 beds \| 3 baths \| 2,961 sq.ft.	$525,000	Airbnb cash on cash: 2.35% Traditional cash on cash: 4.03% Airbnb Rental Income: $3164 Traditional Rental Income: $3269 Airbnb ROI: 2.35% Traditional ROI: 4.03%
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.	$249,900	Airbnb cash on cash: 7.02% Traditional cash on cash: 5.33% Airbnb Rental Income: $3164 Traditional Rental Income: $2049 Airbnb ROI: 7.02% Traditional ROI: 5.33%
24215 BELLE MEDE DRIVE Leesburg, FL Prepare to be awed by this exquisite home. It is a MUST SEE! Right From the curb you will ...	2 beds \| 3 baths \| 2,755 sq.ft.	$429,500	Airbnb cash on cash: 0.75% Traditional cash on cash: 3.06% Airbnb Rental Income: $1980 Traditional Rental Income: $2392 Airbnb ROI: 0.75% Traditional ROI: 3.06%
25008 CYPRESS POND COURT Leesburg, FL PRICE DROP ALERT! $15,000 off this beautifully upgraded Grand Cypress floor plan!!! This ...	3 beds \| 2 baths \| 1,856 sq.ft.	$320,000	Airbnb cash on cash: 5.43% Traditional cash on cash: 4.71% Airbnb Rental Income: $3164 Traditional Rental Income: $2231 Airbnb ROI: 5.43% Traditional ROI: 4.71%
27106 CAMERONS RUN Leesburg, FL NEW ROOF! This beautifully landscaped property offers a 3-bedroom, 2-bath split floor plan...	3 beds \| 2 baths \| 2,436 sq.ft.	$437,500	Airbnb cash on cash: 3.32% Traditional cash on cash: 3.36% Airbnb Rental Income: $3164 Traditional Rental Income: $2466 Airbnb ROI: 3.32% Traditional ROI: 3.36%
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%
21708 ROYAL ST GEORGES LANE Leesburg, FL New Improved Price!!! Royal Highlands a gated 55+ active community is ready for a new own...	3 beds \| 2 baths \| 2,253 sq.ft.	$228,000	Airbnb cash on cash: 7.12% Traditional cash on cash: 5.65% Airbnb Rental Income: $3164 Traditional Rental Income: $2132 Airbnb ROI: 7.12% Traditional ROI: 5.65%
25233 LOST OAK CIRCLE Leesburg, FL Welcome to refined Florida living in the Plantation at Leesburg, a guard-gated community w...	3 beds \| 2 baths \| 1,751 sq.ft.	$325,000	Airbnb cash on cash: 5.23% Traditional cash on cash: 4.37% Airbnb Rental Income: $3164 Traditional Rental Income: $2187 Airbnb ROI: 5.23% Traditional ROI: 4.37%

Real Estate investment in Leesburg, FL

There are 306 properties for sale in the city of Leesburg . The median list price in Leesburg is $299,355 and the average price per square foot is $170. In February 2026, the average monthly cash on cash return in Leesburg is 4.00%. The average monthly rental income in Leesburg is $1,865.

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

There are 306 investment properties available for sale in Leesburg.

In 2026, 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

5552 KING JAMES AVENUE

Leesburg, FL

3 beds | 2 baths | 1,469 sq.ft.

$282,000

Airbnb cash on cash: 6.14%

Traditional cash on cash: 4.04%

Airbnb Rental Income: $3164

Traditional Rental Income: $1891

Airbnb ROI: 6.14%

Traditional ROI: 4.04%

26822 BULL RUN

Leesburg, FL

3 beds | 2 baths | 1,602 sq.ft.

$329,000

Airbnb cash on cash: 4.51%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $3164

Traditional Rental Income: $2047

Airbnb ROI: 4.51%

Traditional ROI: 3.21%

24112 ROBINWOOD STREET

Leesburg, FL

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

$359,000

Airbnb cash on cash: 1.74%

Traditional cash on cash: 3.7%

Airbnb Rental Income: $1980

Traditional Rental Income: $2122

Airbnb ROI: 1.74%

Traditional ROI: 3.7%

4110 ARLINGTON RIDGE BOULEVARD

Leesburg, FL

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

$385,000

Airbnb cash on cash: 4.13%

Traditional cash on cash: 3.49%

Airbnb Rental Income: $3164

Traditional Rental Income: $2216

Airbnb ROI: 4.13%

Traditional ROI: 3.49%

33651 OVERTON DRIVE

Leesburg, FL

3 beds | 4 baths | 3,006 sq.ft.

$520,000

Airbnb cash on cash: 2.83%

Traditional cash on cash: 2.68%

Airbnb Rental Income: $3164

Traditional Rental Income: $2377

Airbnb ROI: 2.83%

Traditional ROI: 2.68%

33719 OVERTON DRIVE

Leesburg, FL

4 beds | 3 baths | 2,340 sq.ft.

$437,500

Airbnb cash on cash: 7.83%

Traditional cash on cash: 7.11%

Airbnb Rental Income: $5065

Traditional Rental Income: $3737

Airbnb ROI: 7.83%

Traditional ROI: 7.11%

3605 MOUNT HOPE LOOP

Leesburg, FL

2 beds | 2 baths | 1,868 sq.ft.

$325,000

Airbnb cash on cash: 2.58%

Traditional cash on cash: 4.08%

Airbnb Rental Income: $1980

Traditional Rental Income: $1919

Airbnb ROI: 2.58%

Traditional ROI: 4.08%

41041 WHILDEN LANE

Leesburg, FL

5 beds | 3 baths | 2,768 sq.ft.

$480,500

Airbnb cash on cash: N/A

Traditional cash on cash: 5.62%

Airbnb Rental Income: $null

Traditional Rental Income: $3386

Airbnb ROI: N/A