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
25723 BELLE ALLIANCE Leesburg, FL Under contract-accepting backup offers. Affordable POOL HOME ON the GOLF COURSEâdonât ...	2 beds \| 2 baths \| 1,667 sq.ft.	$240,000	Airbnb cash on cash: 3.18% Traditional cash on cash: 6.52% Airbnb Rental Income: $1980 Traditional Rental Income: $2219 Airbnb ROI: 3.18% Traditional ROI: 6.52%
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.	$279,000	Airbnb cash on cash: 6.21% Traditional cash on cash: 5.54% Airbnb Rental Income: $3164 Traditional Rental Income: $2270 Airbnb ROI: 6.21% Traditional ROI: 5.54%
2309 Angel Fish Loop Leesburg, FL 3/2/2 CBS Home where Rustic Elegance Meets Modern Comfort. Experience the perfect blend of...	3 beds \| 2 baths \| 1,337 sq.ft.	$329,000	Airbnb cash on cash: 5.46% Traditional cash on cash: 4.38% Airbnb Rental Income: $3164 Traditional Rental Income: $2115 Airbnb ROI: 5.46% Traditional ROI: 4.38%
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.	$324,000	Airbnb cash on cash: 4.59% Traditional cash on cash: 4.37% Airbnb Rental Income: $3164 Traditional Rental Income: $2380 Airbnb ROI: 4.59% Traditional ROI: 4.37%
12114 EAGLE POINT COURT Leesburg, FL Where golden sunsets melt into shimmering water and every day feels like a private escape,...	4 beds \| 3 baths \| 2,570 sq.ft.	$1,199,000	Airbnb cash on cash: 1.8% Traditional cash on cash: 1.49% Airbnb Rental Income: $5065 Traditional Rental Income: $3689 Airbnb ROI: 1.8% Traditional ROI: 1.49%
18 Weston Road Leesburg, FL WATERFRONT, MOVE-IN READY & RARE! 3BR/2BA canal-front home with direct access to Lake Grif...	3 beds \| 2 baths \| 2,016 sq.ft.	$444,900	Airbnb cash on cash: 3.73% Traditional cash on cash: 4.6% Airbnb Rental Income: $3164 Traditional Rental Income: $2809 Airbnb ROI: 3.73% Traditional ROI: 4.6%
7247 TREASURE ISLAND ROAD Leesburg, FL Act fast â opportunities like this don't last! Seller offering approximately $15,000 tow...	3 beds \| 2 baths \| 2,156 sq.ft.	$415,000	Airbnb cash on cash: 4.06% Traditional cash on cash: 5.38% Airbnb Rental Income: $3164 Traditional Rental Income: $2959 Airbnb ROI: 4.06% Traditional ROI: 5.38%
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.	$235,000	Airbnb cash on cash: 2.89% Traditional cash on cash: 3.85% Airbnb Rental Income: $1980 Traditional Rental Income: $1674 Airbnb ROI: 2.89% Traditional ROI: 3.85%
26868 WHITE PLAINS WAY Leesburg, FL 4 bedroom 2 bath with Spectacular Golf View from the Tee Boxes to the Green and pond from ...	4 beds \| 2 baths \| 1,877 sq.ft.	$355,000	Airbnb cash on cash: 9% Traditional cash on cash: 4.13% Airbnb Rental Income: $4837 Traditional Rental Income: $2219 Airbnb ROI: 9% Traditional ROI: 4.13%
33651 OVERTON DRIVE Leesburg, FL Welcome to Leesburg, the âCity of Lakes,â where space, privacy, and convenience come t...	3 beds \| 4 baths \| 2,678 sq.ft.	$485,000	Airbnb cash on cash: 3.08% Traditional cash on cash: 9.77% Airbnb Rental Income: $3164 Traditional Rental Income: $5482 Airbnb ROI: 3.08% Traditional ROI: 9.77%
1120 WEBSTER STREET Leesburg, FL Located Just a few blocks from Downtown Leesburg (Beacon College, Restaurants, shopping), ...	6 beds \| N/A baths \| 3,382 sq.ft.	$425,000	Airbnb cash on cash: N/A Traditional cash on cash: 4.41% Airbnb Rental Income: $null Traditional Rental Income: $2811 Airbnb ROI: N/A Traditional ROI: 4.41%
3605 MOUNT HOPE LOOP Leesburg, FL âThis home can be purchased with NO INCOME VERIFICATIONâ Stunning Grand Cypress in Gle...	2 beds \| 2 baths \| 1,868 sq.ft.	$309,000	Airbnb cash on cash: 2.76% Traditional cash on cash: 5.69% Airbnb Rental Income: $1980 Traditional Rental Income: $2311 Airbnb ROI: 2.76% Traditional ROI: 5.69%
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: 5.74% Traditional cash on cash: 5.42% Airbnb Rental Income: $3164 Traditional Rental Income: $2367 Airbnb ROI: 5.74% 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: 4.82% Traditional cash on cash: 5.01% Airbnb Rental Income: $3164 Traditional Rental Income: $2508 Airbnb ROI: 4.82% Traditional ROI: 5.01%
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: 4.56% Airbnb Rental Income: $3164 Traditional Rental Income: $7481 Airbnb ROI: 0.23% Traditional ROI: 4.56%
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.	$309,999	Airbnb cash on cash: 5.68% Traditional cash on cash: 6.71% Airbnb Rental Income: $3164 Traditional Rental Income: $2748 Airbnb ROI: 5.68% Traditional ROI: 6.71%
109 N OAKLAND STREET Leesburg, FL Under contract-accepting backup offers. This charming property at 109 N Oakland Street off...	3 beds \| 2 baths \| 1,512 sq.ft.	$242,400	Airbnb cash on cash: 8.11% Traditional cash on cash: 7.96% Airbnb Rental Income: $3164 Traditional Rental Income: $2414 Airbnb ROI: 8.11% Traditional ROI: 7.96%
31631 BROADWATER AVENUE Leesburg, FL Welcome to your next chapter in one of Leesburg's most desirable residential pockets, wher...	4 beds \| 2 baths \| 2,140 sq.ft.	$339,999	Airbnb cash on cash: 9.58% Traditional cash on cash: 5.85% Airbnb Rental Income: $4837 Traditional Rental Income: $2651 Airbnb ROI: 9.58% Traditional ROI: 5.85%
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.	$308,000	Airbnb cash on cash: 0.55% Traditional cash on cash: 4.57% Airbnb Rental Income: $1980 Traditional Rental Income: $2627 Airbnb ROI: 0.55% Traditional ROI: 4.57%
11637 LAKE DRIVE Leesburg, FL Welcome to your next chapter in the heart of Leesburgâwhere comfort, style, and space co...	3 beds \| 2 baths \| 1,898 sq.ft.	$349,900	Airbnb cash on cash: 5.16% Traditional cash on cash: 5.24% Airbnb Rental Income: $3164 Traditional Rental Income: $2473 Airbnb ROI: 5.16% Traditional ROI: 5.24%
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: 6.61% Traditional cash on cash: 9.94% Airbnb Rental Income: $1980 Traditional Rental Income: $1874 Airbnb ROI: 6.61% Traditional ROI: 9.94%
5338 TIGERS TAIL Leesburg, FL Assumable 2.5% loan! This delightful home in Plantation at Leesburg is one of the most sou...	2 beds \| 2 baths \| 1,050 sq.ft.	$230,000	Airbnb cash on cash: 3.55% Traditional cash on cash: 4.8% Airbnb Rental Income: $1980 Traditional Rental Income: $1733 Airbnb ROI: 3.55% Traditional ROI: 4.8%
25501 MAUREPAS LANE Leesburg, FL *One or more photos are virtually staged* PREMIUM LOT! NO REAR NEIGHBORS & PANORAMIC ...	2 beds \| 2 baths \| 2,945 sq.ft.	$499,000	Airbnb cash on cash: 0.56% Traditional cash on cash: 2.82% Airbnb Rental Income: $1980 Traditional Rental Income: $2519 Airbnb ROI: 0.56% Traditional ROI: 2.82%
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.	$829,900	Airbnb cash on cash: 3.11% Traditional cash on cash: 3.45% Airbnb Rental Income: $4837 Traditional Rental Income: $4110 Airbnb ROI: 3.11% Traditional ROI: 3.45%
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.	$55,000	Airbnb cash on cash: 4.43% Traditional cash on cash: 9.31% Airbnb Rental Income: $1980 Traditional Rental Income: $1732 Airbnb ROI: 4.43% Traditional ROI: 9.31%
5204 SCOTLAND COURT Leesburg, FL Welcome to this beautifully maintained 3-bedroom, 2.5-bath home with a versatile flex room...	3 beds \| 3 baths \| 2,426 sq.ft.	$418,000	Airbnb cash on cash: 3.43% Traditional cash on cash: 3.98% Airbnb Rental Income: $3164 Traditional Rental Income: $2664 Airbnb ROI: 3.43% Traditional ROI: 3.98%
1611 INDIAN TRAIL Leesburg, FL Investor opportunity in Leesburg, Florida. This fully rented single-family property offers...	6 beds \| N/A 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%
7320 MARLO ROAD Leesburg, FL Classic Florida charm meets peaceful privacy in this spacious 3-bedroom, 3-bath home offer...	3 beds \| 3 baths \| 2,584 sq.ft.	$325,000	Airbnb cash on cash: 6.05% Traditional cash on cash: 9.36% Airbnb Rental Income: $3164 Traditional Rental Income: $3457 Airbnb ROI: 6.05% Traditional ROI: 9.36%
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.	$324,500	Airbnb cash on cash: 4.09% Traditional cash on cash: 4.41% Airbnb Rental Income: $3164 Traditional Rental Income: $2544 Airbnb ROI: 4.09% Traditional ROI: 4.41%
5610 KING JAMES AVENUE Leesburg, FL ~BRING ALL OFFERS!~ COMPLETELY REFRESHED - NEW ROOF 2025, Move-In Ready. This 3-bedroom, 2...	3 beds \| 2 baths \| 1,606 sq.ft.	$219,900	Airbnb cash on cash: 8.44% Traditional cash on cash: 8.32% Airbnb Rental Income: $3164 Traditional Rental Income: $2423 Airbnb ROI: 8.44% Traditional ROI: 8.32%
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.	$99,900	Airbnb cash on cash: 9.62% Traditional cash on cash: 11.02% Airbnb Rental Income: $1980 Traditional Rental Income: $1597 Airbnb ROI: 9.62% Traditional ROI: 11.02%
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: 2.3% Traditional cash on cash: 4.21% Airbnb Rental Income: $3164 Traditional Rental Income: $3384 Airbnb ROI: 2.3% Traditional ROI: 4.21%
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.	$235,000	Airbnb cash on cash: 7.52% Traditional cash on cash: 7.28% Airbnb Rental Income: $3164 Traditional Rental Income: $2395 Airbnb ROI: 7.52% Traditional ROI: 7.28%
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.	$424,900	Airbnb cash on cash: 0.77% Traditional cash on cash: 4.39% Airbnb Rental Income: $1980 Traditional Rental Income: $2905 Airbnb ROI: 0.77% Traditional ROI: 4.39%
33817 SECRET HILL DRIVE Leesburg, FL Under contract-accepting backup offers. NO HOA with room to park your boat/RV! Welcome to ...	3 beds \| 2 baths \| 1,610 sq.ft.	$315,000	Airbnb cash on cash: 6.7% Traditional cash on cash: 6.19% Airbnb Rental Income: $3164 Traditional Rental Income: $2299 Airbnb ROI: 6.7% Traditional ROI: 6.19%
4940 HERON RUN CIRCLE Leesburg, FL Under contract-accepting backup offers. Attention nature lovers and sunset seekers! This c...	2 beds \| 2 baths \| 1,289 sq.ft.	$245,000	Airbnb cash on cash: 2.84% Traditional cash on cash: 4.19% Airbnb Rental Income: $1980 Traditional Rental Income: $1773 Airbnb ROI: 2.84% Traditional ROI: 4.19%
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: 3.5% Traditional cash on cash: 4.03% Airbnb Rental Income: $3164 Traditional Rental Income: $2656 Airbnb ROI: 3.5% Traditional ROI: 4.03%
26617 OTTER CREEK LANE Leesburg, FL Sellerâs are Motivated! Beautifully maintained 4/3 with an office, brand new roof (1/202...	4 beds \| 3 baths \| 2,580 sq.ft.	$525,000	Airbnb cash on cash: 4.95% Traditional cash on cash: 3.29% Airbnb Rental Income: $4837 Traditional Rental Income: $3025 Airbnb ROI: 4.95% Traditional ROI: 3.29%
215 FERNWOOD STREET Leesburg, FL Fully remodeled 3BR/2BA half duplex on a quiet street in Leesburg. Renovated in 2022 with ...	3 beds \| 2 baths \| 1,369 sq.ft.	$219,900	Airbnb cash on cash: 9.3% Traditional cash on cash: 8.22% Airbnb Rental Income: $3164 Traditional Rental Income: $2222 Airbnb ROI: 9.3% Traditional ROI: 8.22%
33710 LINDA LANE Leesburg, FL One or more photo(s) has been virtually staged. Beautiful Pool Home on Linda Lane! This sp...	3 beds \| 3 baths \| 2,395 sq.ft.	$375,000	Airbnb cash on cash: 4.38% Traditional cash on cash: 7.36% Airbnb Rental Income: $3164 Traditional Rental Income: $3496 Airbnb ROI: 4.38% Traditional ROI: 7.36%

Real Estate investment in Leesburg, FL

There are 276 properties for sale in the city of Leesburg . The median list price in Leesburg is $305,000 and the average price per square foot is $170. In May 2026, the average monthly cash on cash return in Leesburg is 5.00%. The average monthly rental income in Leesburg is $1,931.

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

There are 276 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 $1,931.

Your search for investment property begins and ends here

Investment Property for Sale in Leesburg, FL

25723 BELLE ALLIANCE

Leesburg, FL

2 beds | 2 baths | 1,667 sq.ft.

$240,000

Airbnb cash on cash: 3.18%

Traditional cash on cash: 6.52%

Airbnb Rental Income: $1980

Traditional Rental Income: $2219

Airbnb ROI: 3.18%

Traditional ROI: 6.52%

5552 KING JAMES AVENUE

Leesburg, FL

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

$279,000

Airbnb cash on cash: 6.21%

Traditional cash on cash: 5.54%

Airbnb Rental Income: $3164

Traditional Rental Income: $2270

Airbnb ROI: 6.21%

Traditional ROI: 5.54%

2309 Angel Fish Loop

Leesburg, FL

3 beds | 2 baths | 1,337 sq.ft.

$329,000

Airbnb cash on cash: 5.46%

Traditional cash on cash: 4.38%

Airbnb Rental Income: $3164

Traditional Rental Income: $2115

Airbnb ROI: 5.46%

Traditional ROI: 4.38%

26822 BULL RUN

Leesburg, FL

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

$324,000

Airbnb cash on cash: 4.59%

Traditional cash on cash: 4.37%

Airbnb Rental Income: $3164

Traditional Rental Income: $2380

Airbnb ROI: 4.59%

Traditional ROI: 4.37%

12114 EAGLE POINT COURT

Leesburg, FL

4 beds | 3 baths | 2,570 sq.ft.

$1,199,000

Airbnb cash on cash: 1.8%

Traditional cash on cash: 1.49%

Airbnb Rental Income: $5065

Traditional Rental Income: $3689

Airbnb ROI: 1.8%

Traditional ROI: 1.49%

18 Weston Road

Leesburg, FL

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

$444,900

Airbnb cash on cash: 3.73%

Traditional cash on cash: 4.6%

Airbnb Rental Income: $3164

Traditional Rental Income: $2809

Airbnb ROI: 3.73%

Traditional ROI: 4.6%

7247 TREASURE ISLAND ROAD

Leesburg, FL

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

$415,000

Airbnb cash on cash: 4.06%

Traditional cash on cash: 5.38%

Airbnb Rental Income: $3164

Traditional Rental Income: $2959

Airbnb ROI: 4.06%

Traditional ROI: 5.38%

4967 HERON RUN CIRCLE

Leesburg, FL

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

$235,000

Airbnb cash on cash: 2.89%

Traditional cash on cash: 3.85%

Airbnb Rental Income: $1980

Traditional Rental Income: $1674

Airbnb ROI: 2.89%