Real Estate Investment Properties for Sale in Brooksville, FL

Looking for investment property in Brooksville, FL with high ROI ?

Explore a variety of short-term homes & houses in Brooksville, FL. Invest wisely with VRBO & Brooksville, 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 Brooksville, FL

separator

PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
5233 jennings Trail Brooksville, FL Move in ready home in the Cascades at Southern Hills a 55+ Community located in the sought...	2 beds \| 2 baths \| 2,073 sq.ft.	$383,800	Airbnb cash on cash: -0.64% Traditional cash on cash: 3.21% Airbnb Rental Income: $1391 Traditional Rental Income: $2356 Airbnb ROI: -0.64% Traditional ROI: 3.21%
4413 Caliquen Drive Brooksville, FL A brand new roof now tops this beautiful home! This lovely, well maintained 3/2/2 home is ...	3 beds \| 2 baths \| 2,314 sq.ft.	$350,000	Airbnb cash on cash: 3.59% Traditional cash on cash: 4% Airbnb Rental Income: $2561 Traditional Rental Income: $2081 Airbnb ROI: 3.59% Traditional ROI: 4%
10110 Weeks Drive Brooksville, FL HUGE POOL HOME IN HERNANDO COUNTRY CLUB WITH BRAND NEW ROOF!! WELCOME TO YOUR DREAM HOME!!...	5 beds \| 4 baths \| 3,554 sq.ft.	$825,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.09% Airbnb Rental Income: $null Traditional Rental Income: $4601 Airbnb ROI: N/A Traditional ROI: 3.09%
4367 BURNS ROAD Brooksville, FL Welcome to Your Private Paradise! Discover the perfect blend of tranquility and convenie...	3 beds \| 2 baths \| 1,982 sq.ft.	$550,000	Airbnb cash on cash: 2.01% Traditional cash on cash: 3.45% Airbnb Rental Income: $2561 Traditional Rental Income: $2683 Airbnb ROI: 2.01% Traditional ROI: 3.45%
4412 CALIQUEN DRIVE Brooksville, FL Beautiful Quality Built Palmwood Bimini Breeze Courtyard Home Located in Hernando Counties...	3 beds \| 3 baths \| 2,235 sq.ft.	$299,000	Airbnb cash on cash: 3.63% Traditional cash on cash: 5.57% Airbnb Rental Income: $2561 Traditional Rental Income: $2491 Airbnb ROI: 3.63% Traditional ROI: 5.57%
10193 Wallien Drive Brooksville, FL Located in the highly desirable Dogwood Estates golf course community, this stunning 4-bed...	4 beds \| 4 baths \| 3,404 sq.ft.	$649,000	Airbnb cash on cash: 5.26% Traditional cash on cash: 8.14% Airbnb Rental Income: $5422 Traditional Rental Income: $6079 Airbnb ROI: 5.26% Traditional ROI: 8.14%
5149 Jennings Trail Brooksville, FL Immaculate Lakefront Home in The Cascades at Southern Hills - 55+ Community New! Homeowner...	3 beds \| 3 baths \| 2,322 sq.ft.	$476,532	Airbnb cash on cash: 0.76% Traditional cash on cash: 2.66% Airbnb Rental Income: $2561 Traditional Rental Income: $2792 Airbnb ROI: 0.76% Traditional ROI: 2.66%
15407 Singleton Drive Brooksville, FL PRICED BELOW RECENT APPRAISAL! BRAND NEW AC & BRAND NEW ELECTRICAL PANEL! Welcome to your ...	2 beds \| 2 baths \| 1,152 sq.ft.	$167,500	Airbnb cash on cash: 3.69% Traditional cash on cash: 10.87% Airbnb Rental Income: $1391 Traditional Rental Income: $2117 Airbnb ROI: 3.69% Traditional ROI: 10.87%
19555 Phillips Road Brooksville, FL Move-In Ready with Major Upgrades! This beautifully maintained home offers true peace of m...	3 beds \| 2 baths \| 1,997 sq.ft.	$600,000	Airbnb cash on cash: 1.56% Traditional cash on cash: 2.5% Airbnb Rental Income: $2561 Traditional Rental Income: $2473 Airbnb ROI: 1.56% Traditional ROI: 2.5%
9184 Dan Lynn Street Brooksville, FL Gulf Ridge Park is conveniently bordered by W Ft Dade, Ponce de Leon and Manecke Rd. Conve...	3 beds \| 1 baths \| 1,140 sq.ft.	$175,000	Airbnb cash on cash: 9.64% Traditional cash on cash: 7.99% Airbnb Rental Income: $2561 Traditional Rental Income: $1670 Airbnb ROI: 9.64% Traditional ROI: 7.99%
1398 E TRAIL 28 Brooksville, FL PENDING TAKING BACKUP OFFERS. WHAT A BEAUTY! THIS 3 BEDROOM 2 BATH WITH GATED ELECTRIC ENT...	3 beds \| 2 baths \| 1,968 sq.ft.	$721,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 1.5% Airbnb Rental Income: $2561 Traditional Rental Income: $2370 Airbnb ROI: 0.87% Traditional ROI: 1.5%
15205 DURANGO CIR Brooksville, FL Welcome to this charming 3-bedroom, 2-bathroom, 2-car garage pool home located in the high...	3 beds \| 2 baths \| 1,431 sq.ft.	$330,000	Airbnb cash on cash: 3.97% Traditional cash on cash: 4.93% Airbnb Rental Income: $2561 Traditional Rental Income: $2244 Airbnb ROI: 3.97% Traditional ROI: 4.93%
12325 Fairway Avenue Brooksville, FL PRICE REDUCED! Rare find! POOL home with 3 bedrooms in High Point Community. Lots of updat...	3 beds \| 2 baths \| 1,536 sq.ft.	$185,000	Airbnb cash on cash: 8.62% Traditional cash on cash: 10.97% Airbnb Rental Income: $2561 Traditional Rental Income: $2358 Airbnb ROI: 8.62% Traditional ROI: 10.97%
12018 Mississippi Kite Avenue Brooksville, FL Hunny Stop the car! Check out this Beautiful Well-Loved 1 Off Custom home! Built in 2020 L...	3 beds \| 2 baths \| 2,157 sq.ft.	$465,999	Airbnb cash on cash: 2.42% Traditional cash on cash: 4.32% Airbnb Rental Income: $2561 Traditional Rental Income: $2777 Airbnb ROI: 2.42% Traditional ROI: 4.32%
15693 Brookridge Boulevard Brooksville, FL Nice large home in Brookridge community with lots of space with over 1400 sq ft of main li...	2 beds \| 2 baths \| 1,416 sq.ft.	$194,900	Airbnb cash on cash: 2.96% Traditional cash on cash: 8.41% Airbnb Rental Income: $1391 Traditional Rental Income: $1978 Airbnb ROI: 2.96% Traditional ROI: 8.41%
7041 LEXINGTON CIRCLE Brooksville, FL SELLER OPEN TO OFFERS. FinallyâA Move-In Ready Home with a Rare FHA Assumable Loan! Tuck...	3 beds \| 2 baths \| 1,302 sq.ft.	$289,900	Airbnb cash on cash: 5.19% Traditional cash on cash: 5.06% Airbnb Rental Income: $2561 Traditional Rental Income: $1910 Airbnb ROI: 5.19% Traditional ROI: 5.06%
992 NODDING SHADE DRIVE Brooksville, FL Welcome to this EXCEPTIONAL 4-BEDROOM, 2.5-BATH HOME with BONUS DEN/OFFICE that can be use...	4 beds \| 3 baths \| 2,396 sq.ft.	$415,000	Airbnb cash on cash: 9.35% Traditional cash on cash: 4% Airbnb Rental Income: $5861 Traditional Rental Income: $2617 Airbnb ROI: 9.35% Traditional ROI: 4%
717 Whiteway Drive Brooksville, FL Charming & Fully Updated Home on a Spacious Double Lot! Welcome to 717 White Way Drive - a...	2 beds \| 1 baths \| 806 sq.ft.	$230,000	Airbnb cash on cash: 2.62% Traditional cash on cash: 5.18% Airbnb Rental Income: $1391 Traditional Rental Income: $1526 Airbnb ROI: 2.62% Traditional ROI: 5.18%
901 MOONLIGHT Lane Brooksville, FL Welcome to your dream home in the heart of Brooksville! This beautifully updated 3 bedroom...	3 beds \| 2 baths \| 1,521 sq.ft.	$389,000	Airbnb cash on cash: 3.13% Traditional cash on cash: 4.11% Airbnb Rental Income: $2561 Traditional Rental Income: $2305 Airbnb ROI: 3.13% Traditional ROI: 4.11%
27001 WAKEFIELD DRIVE Brooksville, FL One or more photo(s) has been virtually staged. Beautiful 3-Bedroom, 2.5 Bathroom with Lof...	3 beds \| 3 baths \| 1,660 sq.ft.	$320,000	Airbnb cash on cash: 4.21% Traditional cash on cash: 5.55% Airbnb Rental Income: $2561 Traditional Rental Income: $2349 Airbnb ROI: 4.21% Traditional ROI: 5.55%
15287 STONE HOUSE DRIVE Brooksville, FL Why Youâll Love This Home! This stunning 2017 Pulte-built home in Trillium Village is f...	3 beds \| 2 baths \| 1,978 sq.ft.	$345,000	Airbnb cash on cash: 3.27% Traditional cash on cash: 5.1% Airbnb Rental Income: $2561 Traditional Rental Income: $2538 Airbnb ROI: 3.27% Traditional ROI: 5.1%
8150 SOUTHERN PINES DR Brooksville, FL One or more photo(s) has been virtually staged. Spacious & Elegant Condo in Southern Pines...	2 beds \| 2 baths \| 1,674 sq.ft.	$209,900	Airbnb cash on cash: -2.08% Traditional cash on cash: 5.25% Airbnb Rental Income: $1391 Traditional Rental Income: $2430 Airbnb ROI: -2.08% Traditional ROI: 5.25%
8178 Southern Pines Drive Brooksville, FL Welcome to this spacious 2-bedroom, 2-bathroom condo in the desirable Southern Pines commu...	2 beds \| 2 baths \| 1,674 sq.ft.	$219,000	Airbnb cash on cash: 0.07% Traditional cash on cash: 7.28% Airbnb Rental Income: $1391 Traditional Rental Income: $2465 Airbnb ROI: 0.07% Traditional ROI: 7.28%
11730 HAWKS NEST TRAIL Brooksville, FL Tucked away at the end of a peaceful cul-de-sac, this charming country-style cottage (with...	3 beds \| 2 baths \| 1,972 sq.ft.	$685,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 1.4% Airbnb Rental Income: $2561 Traditional Rental Income: $2321 Airbnb ROI: 0.81% Traditional ROI: 1.4%
5198 Legend Hills Lane Brooksville, FL Welcome to this one-of-a-kind custom built luxury home in the desired Golf and Country Clu...	4 beds \| 3 baths \| 3,391 sq.ft.	$840,000	Airbnb cash on cash: 3.56% Traditional cash on cash: 1.29% Airbnb Rental Income: $5247 Traditional Rental Income: $2408 Airbnb ROI: 3.56% Traditional ROI: 1.29%
6423 BOXWOOD STREET Brooksville, FL Welcome to this beautiful 3-bedroom, 2-bathroom, 2 car-garage space single-family home in ...	3 beds \| 2 baths \| 1,395 sq.ft.	$295,000	Airbnb cash on cash: 4.27% Traditional cash on cash: 4.51% Airbnb Rental Income: $2561 Traditional Rental Income: $2011 Airbnb ROI: 4.27% Traditional ROI: 4.51%
1353 Spring Lake Highway Brooksville, FL Rustic Luxury on 16.6 Acres - Private Homestead Retreat in Spring Lake, Brooksville. Nestl...	5 beds \| 5 baths \| 3,900 sq.ft.	$1,200,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.9% Airbnb Rental Income: $null Traditional Rental Income: $6216 Airbnb ROI: N/A Traditional ROI: 3.9%
8442 PINEWOOD AVENUE Brooksville, FL Come see this MOVE-IN READY 2021 block home on nearly a half-acre of land! This home was u...	3 beds \| 2 baths \| 1,449 sq.ft.	$369,000	Airbnb cash on cash: 3.69% Traditional cash on cash: 4.41% Airbnb Rental Income: $2561 Traditional Rental Income: $2195 Airbnb ROI: 3.69% Traditional ROI: 4.41%
435 Painted Leaf Drive Brooksville, FL This stunning 3 bedroom, 2 bathroom, 2 car garage home offers the perfect blend of comfort...	3 beds \| 2 baths \| 1,814 sq.ft.	$329,000	Airbnb cash on cash: 3.37% Traditional cash on cash: 4.2% Airbnb Rental Income: $2561 Traditional Rental Income: $2200 Airbnb ROI: 3.37% Traditional ROI: 4.2%
27315 POPIEL ROAD Brooksville, FL Welcome to your private slice of paradise! Nestled on 2.4 acres of peaceful, fully fenced ...	3 beds \| 2 baths \| 1,356 sq.ft.	$399,000	Airbnb cash on cash: 3.12% Traditional cash on cash: 3.21% Airbnb Rental Income: $2561 Traditional Rental Income: $1978 Airbnb ROI: 3.12% Traditional ROI: 3.21%
6234 NEFF LAKE ROAD Brooksville, FL NO FLOOD INSURANCE REQUIREDNO HISTORY OF FLOODING**OPPORTUNITY KNOCKS - INVESTOR speci...	3 beds \| 2 baths \| 2,001 sq.ft.	$399,000	Airbnb cash on cash: 2.71% Traditional cash on cash: 2.49% Airbnb Rental Income: $2561 Traditional Rental Income: $1863 Airbnb ROI: 2.71% Traditional ROI: 2.49%
221 HIGHLAND STREET Brooksville, FL MULTIPLE OFFERS RECEIVED. PLEASE SUBMIT HIGHEST AND BEST OFFER BY 5PM 8/10/25/. FANTASTIC...	2 beds \| 2 baths \| 1,008 sq.ft.	$139,900	Airbnb cash on cash: 4.04% Traditional cash on cash: 10.04% Airbnb Rental Income: $1391 Traditional Rental Income: $1775 Airbnb ROI: 4.04% Traditional ROI: 10.04%
15585 LILY WOOD LANE Brooksville, FL Nestled in the sought-after Trillium community, this well-appointed home features 3 bedroo...	3 beds \| 2 baths \| 1,814 sq.ft.	$310,000	Airbnb cash on cash: 3.75% Traditional cash on cash: 4.86% Airbnb Rental Income: $2561 Traditional Rental Income: $2271 Airbnb ROI: 3.75% Traditional ROI: 4.86%
19581 LILY POND COURT Brooksville, FL Welcome to this stunning property located within the prestigious gated Southern Hills Plan...	2 beds \| 2 baths \| 1,892 sq.ft.	$445,000	Airbnb cash on cash: -2.03% Traditional cash on cash: 1.04% Airbnb Rental Income: $1391 Traditional Rental Income: $2251 Airbnb ROI: -2.03% Traditional ROI: 1.04%
5388 FEZ COURT Brooksville, FL You are home sweet home! A new roof installed in 2022 adds to the appeal of this beautiful...	3 beds \| 2 baths \| 1,596 sq.ft.	$315,000	Airbnb cash on cash: 3.95% Traditional cash on cash: 4.64% Airbnb Rental Income: $2561 Traditional Rental Income: $2147 Airbnb ROI: 3.95% Traditional ROI: 4.64%
406 ZOLLER STREET Brooksville, FL Discover the perfect blend of classic character and contemporary design in this beautifull...	3 beds \| 2 baths \| 1,332 sq.ft.	$279,000	Airbnb cash on cash: 4.69% Traditional cash on cash: 5.33% Airbnb Rental Income: $2561 Traditional Rental Income: $2114 Airbnb ROI: 4.69% Traditional ROI: 5.33%
4428 GEVALIA DRIVE Brooksville, FL Come visit this stunning 3-Bedroom, 2-Bathroom home in the Premier Gated Golf Course Commu...	3 beds \| 2 baths \| 2,536 sq.ft.	$499,999	Airbnb cash on cash: 1.67% Traditional cash on cash: 3.35% Airbnb Rental Income: $2561 Traditional Rental Income: $2731 Airbnb ROI: 1.67% Traditional ROI: 3.35%
15408 CAMBRIA DRIVE Brooksville, FL Beautifully renovated 3 bedroom, 2 bathroom pool home with 2-car garage on a desirable cor...	3 beds \| 2 baths \| 1,681 sq.ft.	$379,000	Airbnb cash on cash: 2.73% Traditional cash on cash: 4.25% Airbnb Rental Income: $2561 Traditional Rental Income: $2484 Airbnb ROI: 2.73% Traditional ROI: 4.25%
7182 GRIFFIN ROAD Brooksville, FL Peaceful Country Living with Modern Upgrades! Enjoy the best of country living with thi...	3 beds \| 2 baths \| 1,665 sq.ft.	$435,000	Airbnb cash on cash: 2.64% Traditional cash on cash: 2.68% Airbnb Rental Income: $2561 Traditional Rental Income: $1962 Airbnb ROI: 2.64% Traditional ROI: 2.68%
3540 Moondance Circle Brooksville, FL Ready to love where you live? This stunning, move in anytime 2-story home in Deerfield Est...	4 beds \| 3 baths \| 2,724 sq.ft.	$423,500	Airbnb cash on cash: 8.66% Traditional cash on cash: 3.07% Airbnb Rental Income: $5861 Traditional Rental Income: $2478 Airbnb ROI: 8.66% Traditional ROI: 3.07%

Real Estate investment in Brooksville, FL

There are 305 properties for sale in the city of Brooksville . The median list price in Brooksville is $300,000 and the average price per square foot is $169. In September 2025, the average monthly cash on cash return in Brooksville is 5.00%. The average monthly rental income in Brooksville is $2,020.

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

There are 305 investment properties available for sale in Brooksville.

In 2025, the best neighborhood to buy investment property is Brooksville.

The ROI for Long-Term is higher than the Short-Term in Brooksville with average rental income of $2,020.

Your search for investment property begins and ends here

Investment Property for Sale in Brooksville, FL

5233 jennings Trail

Brooksville, FL

2 beds | 2 baths | 2,073 sq.ft.

$383,800

Airbnb cash on cash: -0.64%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $1391

Traditional Rental Income: $2356

Airbnb ROI: -0.64%

Traditional ROI: 3.21%

4413 Caliquen Drive

Brooksville, FL

3 beds | 2 baths | 2,314 sq.ft.

$350,000

Airbnb cash on cash: 3.59%

Traditional cash on cash: 4%

Airbnb Rental Income: $2561

Traditional Rental Income: $2081

Airbnb ROI: 3.59%

Traditional ROI: 4%

10110 Weeks Drive

Brooksville, FL

5 beds | 4 baths | 3,554 sq.ft.

$825,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.09%

Airbnb Rental Income: $null

Traditional Rental Income: $4601

Airbnb ROI: N/A

Traditional ROI: 3.09%

4367 BURNS ROAD

Brooksville, FL

3 beds | 2 baths | 1,982 sq.ft.

$550,000

Airbnb cash on cash: 2.01%

Traditional cash on cash: 3.45%

Airbnb Rental Income: $2561

Traditional Rental Income: $2683

Airbnb ROI: 2.01%

Traditional ROI: 3.45%

4412 CALIQUEN DRIVE

Brooksville, FL

3 beds | 3 baths | 2,235 sq.ft.

$299,000

Airbnb cash on cash: 3.63%

Traditional cash on cash: 5.57%

Airbnb Rental Income: $2561

Traditional Rental Income: $2491

Airbnb ROI: 3.63%

Traditional ROI: 5.57%

10193 Wallien Drive

Brooksville, FL

4 beds | 4 baths | 3,404 sq.ft.

$649,000

Airbnb cash on cash: 5.26%

Traditional cash on cash: 8.14%

Airbnb Rental Income: $5422

Traditional Rental Income: $6079

Airbnb ROI: 5.26%

Traditional ROI: 8.14%

5149 Jennings Trail

Brooksville, FL

3 beds | 3 baths | 2,322 sq.ft.

$476,532

Airbnb cash on cash: 0.76%

Traditional cash on cash: 2.66%

Airbnb Rental Income: $2561

Traditional Rental Income: $2792

Airbnb ROI: 0.76%

Traditional ROI: 2.66%

15407 Singleton Drive

Brooksville, FL

2 beds | 2 baths | 1,152 sq.ft.

$167,500

Airbnb cash on cash: 3.69%

Traditional cash on cash: 10.87%

Airbnb Rental Income: $1391

Traditional Rental Income: $2117

Airbnb ROI: 3.69%