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
1305 WREN AVENUE Leesburg, FL Welcome to 1305 Wren Ave, nestled in the desirable Kingson Park area of Leesburg. This 3 b...	3 beds \| 2 baths \| 2,034 sq.ft.	$345,900	Airbnb cash on cash: 5.72% Traditional cash on cash: 6.94% Airbnb Rental Income: $3164 Traditional Rental Income: $2844 Airbnb ROI: 5.72% Traditional ROI: 6.94%
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%
18 WESTON ROAD Leesburg, FL WATERFRONT RETREAT MEETS MODERN ELEGANCE â MOVE-IN READY & EXTREMELY RARE FIND! Welco...	3 beds \| 2 baths \| 2,016 sq.ft.	$469,500	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%
33651 OVERTON DRIVE Leesburg, FL Spacious Leesburg home with Resort-Style Pool and Dual Master Suites, with no HOA! Discov...	3 beds \| 4 baths \| 3,006 sq.ft.	$530,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 2.62% Airbnb Rental Income: $3164 Traditional Rental Income: $2377 Airbnb ROI: 2.76% Traditional ROI: 2.62%
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.	$305,000	Airbnb cash on cash: 4.97% Traditional cash on cash: 3.92% Airbnb Rental Income: $3164 Traditional Rental Income: $2145 Airbnb ROI: 4.97% Traditional ROI: 3.92%
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 Under contract-accepting backup offers. We are taking Back Up Contracts. Popular Bird of P...	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.	$385,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 2.32% Airbnb Rental Income: $3164 Traditional Rental Income: $2016 Airbnb ROI: 3.52% Traditional ROI: 2.32%
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.	$320,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 4.2% Airbnb Rental Income: $3164 Traditional Rental Income: $2244 Airbnb ROI: 4.88% Traditional ROI: 4.2%
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.	$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%
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.	$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.	$259,000	Airbnb cash on cash: 7.33% Traditional cash on cash: 6.72% Airbnb Rental Income: $3164 Traditional Rental Income: $2299 Airbnb ROI: 7.33% Traditional ROI: 6.72%
26126 NEWCOMBE CIRCLE Leesburg, FL Welcome Home to Relaxed, Resort-Style Living in Lake Highlands 55+ Community Experience c...	3 beds \| 2 baths \| 1,890 sq.ft.	$274,900	Airbnb cash on cash: 6.08% Traditional cash on cash: 5.71% Airbnb Rental Income: $3164 Traditional Rental Income: $2353 Airbnb ROI: 6.08% Traditional ROI: 5.71%
1906 ANGEL FISH LOOP Leesburg, FL Under contract-accepting backup offers. Attention investors. Here is your next project and...	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%
7500 SLOEWOOD DRIVE Leesburg, FL Welcome home to this immaculate 3-bedroom, 2-bath residence located on a quiet cul-de-sac ...	3 beds \| 2 baths \| 1,584 sq.ft.	$349,900	Airbnb cash on cash: 5.94% Traditional cash on cash: 4.64% Airbnb Rental Income: $3164 Traditional Rental Income: $2020 Airbnb ROI: 5.94% Traditional ROI: 4.64%
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.	$399,999	Airbnb cash on cash: 3.01% Traditional cash on cash: 2.76% Airbnb Rental Income: $3164 Traditional Rental Income: $2354 Airbnb ROI: 3.01% Traditional ROI: 2.76%
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 Stunning Custom Savannah/Scarsborough Model in the Sought-After Legacy of Leesburg Communi...	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%
5610 KING JAMES AVENUE Leesburg, FL COMPLETELY REFRESHED - NEW ROOF BEING INSTALLED, Move-In Ready. This 3-bedroom, 2-bath Top...	3 beds \| 2 baths \| 1,606 sq.ft.	$259,900	Airbnb cash on cash: 7.01% Traditional cash on cash: 5.48% Airbnb Rental Income: $3164 Traditional Rental Income: $2072 Airbnb ROI: 7.01% Traditional ROI: 5.48%
34016 VALENCIA DRIVE Leesburg, FL Under contract-accepting backup offers. Spacious 3-Bedroom Home on Oversized Lot â Prime...	3 beds \| 2 baths \| 1,689 sq.ft.	$295,000	Airbnb cash on cash: 6.25% Traditional cash on cash: 4.85% Airbnb Rental Income: $3164 Traditional Rental Income: $2059 Airbnb ROI: 6.25% Traditional ROI: 4.85%
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 Price Negotiable and Seller is Motivated and will look at all offers. Don't be afraid to ...	3 beds \| 3 baths \| 2,961 sq.ft.	$579,000	Airbnb cash on cash: 2.04% Traditional cash on cash: 3.56% Airbnb Rental Income: $3164 Traditional Rental Income: $3269 Airbnb ROI: 2.04% Traditional ROI: 3.56%
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.	$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%
25008 CYPRESS POND COURT Leesburg, FL Welcome to the popular Grand Cypress floor plan, featuring incredible upgrades throughout!...	3 beds \| 2 baths \| 1,856 sq.ft.	$344,900	Airbnb cash on cash: 4.97% Traditional cash on cash: 4.3% Airbnb Rental Income: $3164 Traditional Rental Income: $2231 Airbnb ROI: 4.97% Traditional ROI: 4.3%
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.	$442,500	Airbnb cash on cash: 3.27% Traditional cash on cash: 3.32% Airbnb Rental Income: $3164 Traditional Rental Income: $2466 Airbnb ROI: 3.27% Traditional ROI: 3.32%
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%
25233 LOST OAK CIRCLE Leesburg, FL Welcome to Plantation at Leesburg, a premier active-adult, gated golf community where comf...	3 beds \| 2 baths \| 1,751 sq.ft.	$325,000	Airbnb cash on cash: 5.24% Traditional cash on cash: 4.38% Airbnb Rental Income: $3164 Traditional Rental Income: $2187 Airbnb ROI: 5.24% Traditional ROI: 4.38%

Real Estate investment in Leesburg, FL

There are 310 properties for sale in the city of Leesburg . The median list price in Leesburg is $295,000 and the average price per square foot is $170. In December 2025, the average monthly cash on cash return in Leesburg is 4.00%. The average monthly rental income in Leesburg is $1,881.

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 $1,980.

Your search for investment property begins and ends here

Investment Property for Sale in Leesburg, FL

1305 WREN AVENUE

Leesburg, FL

3 beds | 2 baths | 2,034 sq.ft.

$345,900

Airbnb cash on cash: 5.72%

Traditional cash on cash: 6.94%

Airbnb Rental Income: $3164

Traditional Rental Income: $2844

Airbnb ROI: 5.72%

Traditional ROI: 6.94%

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%

18 WESTON ROAD

Leesburg, FL

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

$469,500

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%

33651 OVERTON DRIVE

Leesburg, FL

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

$530,000

Airbnb cash on cash: 2.76%

Traditional cash on cash: 2.62%

Airbnb Rental Income: $3164

Traditional Rental Income: $2377

Airbnb ROI: 2.76%

Traditional ROI: 2.62%

5133 LINKS LANE

Leesburg, FL

3 beds | 2 baths | 1,701 sq.ft.

$305,000

Airbnb cash on cash: 4.97%

Traditional cash on cash: 3.92%

Airbnb Rental Income: $3164

Traditional Rental Income: $2145

Airbnb ROI: 4.97%

Traditional ROI: 3.92%

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%