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

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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%
4149 Gevalia Drive Brooksville, FL Why build when you can scoop up this beauty?! Pride of ownership shines through with this ...	3 beds \| 2 baths \| 2,032 sq.ft.	$354,800	Airbnb cash on cash: 4.06% Traditional cash on cash: 4.66% Airbnb Rental Income: $2561 Traditional Rental Income: $2145 Airbnb ROI: 4.06% Traditional ROI: 4.66%
10110 Weeks Drive Brooksville, FL PRICE IMPROVEMENT!! SELLER MOTIVATED!! HUGE POOL HOME IN HERNANDO COUNTRY CLUB WITH BRAND ...	5 beds \| N/A baths \| 3,554 sq.ft.	$725,000	Airbnb cash on cash: N/A Traditional cash on cash: 3.65% Airbnb Rental Income: $null Traditional Rental Income: $4601 Airbnb ROI: N/A Traditional ROI: 3.65%
149 ROOSEVELT AVENUE Brooksville, FL Presenting a charming residence featuring three bedrooms, two bathrooms, and a six-car gar...	3 beds \| 2 baths \| 1,296 sq.ft.	$299,000	Airbnb cash on cash: 4.94% Traditional cash on cash: 5.45% Airbnb Rental Income: $2561 Traditional Rental Income: $2088 Airbnb ROI: 4.94% Traditional ROI: 5.45%
27151 HIAWATHA BOULEVARD Brooksville, FL Under contract-accepting backup offers. Charming Country Retreat on 4.80 Acres â Nature,...	3 beds \| 2 baths \| 1,634 sq.ft.	$655,000	Airbnb cash on cash: 1.58% Traditional cash on cash: 2.03% Airbnb Rental Income: $2561 Traditional Rental Income: $2221 Airbnb ROI: 1.58% Traditional ROI: 2.03%
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.	$529,995	Airbnb cash on cash: 2.12% Traditional cash on cash: 3.61% Airbnb Rental Income: $2561 Traditional Rental Income: $2683 Airbnb ROI: 2.12% Traditional ROI: 3.61%
8152 SOUTHERN PINES DRIVE Brooksville, FL Bright 3-bedroom 2 bath condo at Southern Pines conveniently located off US Highway 50 in ...	3 beds \| 2 baths \| 1,640 sq.ft.	$207,900	Airbnb cash on cash: 3.32% Traditional cash on cash: 5.01% Airbnb Rental Income: $2561 Traditional Rental Income: $2279 Airbnb ROI: 3.32% Traditional ROI: 5.01%
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 ove-in ready and upgraded, this well-maintained 3-bedroom, 2-bath home sits on 8.3 fully f...	3 beds \| 2 baths \| 1,997 sq.ft.	$575,000	Airbnb cash on cash: 1.67% Traditional cash on cash: 2.65% Airbnb Rental Income: $2561 Traditional Rental Income: $2473 Airbnb ROI: 1.67% Traditional ROI: 2.65%
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 Under contract-accepting backup offers. Welcome to this charming 3-bedroom, 2-bathroom, 2-...	3 beds \| 2 baths \| 1,431 sq.ft.	$315,000	Airbnb cash on cash: 4.2% Traditional cash on cash: 5.21% Airbnb Rental Income: $2561 Traditional Rental Income: $2244 Airbnb ROI: 4.2% Traditional ROI: 5.21%
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%
19906 TATTNALL WAY Brooksville, FL Donât miss this amazing home, priced far below similar size homes in the community and o...	4 beds \| 3 baths \| 3,130 sq.ft.	$568,500	Airbnb cash on cash: 5.34% Traditional cash on cash: 3.03% Airbnb Rental Income: $5422 Traditional Rental Income: $3105 Airbnb ROI: 5.34% Traditional ROI: 3.03%
7502 MORELLI AVENUE Brooksville, FL Welcome to your Florida paradise in the desirable 55+ gated golf community of Brookridge! ...	2 beds \| 2 baths \| 1,248 sq.ft.	$165,000	Airbnb cash on cash: 3.68% Traditional cash on cash: 8.81% Airbnb Rental Income: $1391 Traditional Rental Income: $1777 Airbnb ROI: 3.68% Traditional ROI: 8.81%
3519 Goldsmith Road Brooksville, FL Come make your Dreams come true at Dream Catcher Ranch! Nestled on a peaceful 5 acres, ver...	3 beds \| 3 baths \| 1,860 sq.ft.	$748,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 1.96% Airbnb Rental Income: $2561 Traditional Rental Income: $2599 Airbnb ROI: 1.02% Traditional ROI: 1.96%
16481 OAKVIEW DRIVE Brooksville, FL Discover the perfect blend of peaceful country living and modern comfort on nearly 5 fence...	4 beds \| 2 baths \| 2,280 sq.ft.	$429,900	Airbnb cash on cash: 8.43% Traditional cash on cash: 4.13% Airbnb Rental Income: $5422 Traditional Rental Income: $2599 Airbnb ROI: 8.43% Traditional ROI: 4.13%
9377 PRESTON ROAD Brooksville, FL PRICE IMPROVED !!! BRING THE HORSES !!! NO HOA !!! NO CDD !! BRAND NEW ROOF !!! The Main...	4 beds \| 3 baths \| 2,490 sq.ft.	$559,000	Airbnb cash on cash: 6.44% Traditional cash on cash: 3.56% Airbnb Rental Income: $5422 Traditional Rental Income: $2827 Airbnb ROI: 6.44% Traditional ROI: 3.56%
5324 Southern Valley Loop Brooksville, FL Welcome to this exquisite 3-bedroom, 4-bathroom residence that seamlessly blends luxury wi...	3 beds \| 4 baths \| 3,189 sq.ft.	$725,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 2.37% Airbnb Rental Income: $2561 Traditional Rental Income: $3760 Airbnb ROI: -0.32% Traditional ROI: 2.37%
996 SCARLET PLUME LANE Brooksville, FL One or more photo(s) has been virtually staged. PRICE REDUCED!!! Welcome to this beautiful...	3 beds \| 2 baths \| 1,978 sq.ft.	$345,000	Airbnb cash on cash: 3.52% Traditional cash on cash: 5.22% Airbnb Rental Income: $2561 Traditional Rental Income: $2497 Airbnb ROI: 3.52% Traditional ROI: 5.22%
30919 WATER LILY DRIVE Brooksville, FL Welcome to this stunning 3-bedroom, 2-bath home located in the desirable Sherman Hills gol...	3 beds \| 2 baths \| 1,546 sq.ft.	$284,900	Airbnb cash on cash: 4.08% Traditional cash on cash: 4.92% Airbnb Rental Income: $2561 Traditional Rental Income: $2173 Airbnb ROI: 4.08% Traditional ROI: 4.92%
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.	$369,900	Airbnb cash on cash: 3.34% Traditional cash on cash: 4.37% Airbnb Rental Income: $2561 Traditional Rental Income: $2305 Airbnb ROI: 3.34% Traditional ROI: 4.37%
14861 WAKE ROBIN DRIVE Brooksville, FL Easy Suncoast Living in the Trillium Community that offers a Beautiful Community Pool & Lo...	3 beds \| 2 baths \| 1,260 sq.ft.	$269,000	Airbnb cash on cash: 4.63% Traditional cash on cash: 4.71% Airbnb Rental Income: $2561 Traditional Rental Income: $1967 Airbnb ROI: 4.63% Traditional ROI: 4.71%
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.	$199,990	Airbnb cash on cash: -2.13% Traditional cash on cash: 5.56% Airbnb Rental Income: $1391 Traditional Rental Income: $2430 Airbnb ROI: -2.13% Traditional ROI: 5.56%
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%
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: 3.6% Traditional cash on cash: 1.33% Airbnb Rental Income: $5247 Traditional Rental Income: $2408 Airbnb ROI: 3.6% Traditional ROI: 1.33%
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%
4455 GEVALIA DRIVE Brooksville, FL Move in ready and beautifully updated, this four bedroom three bath home with a three car ...	4 beds \| 3 baths \| 2,212 sq.ft.	$459,999	Airbnb cash on cash: 8.7% Traditional cash on cash: 3.03% Airbnb Rental Income: $5861 Traditional Rental Income: $2257 Airbnb ROI: 8.7% Traditional ROI: 3.03%
8442 PINEWOOD AVENUE Brooksville, FL SELLER MOTIVATED!! Seller is willing to contribute towards Buyer's pre-paids and closing c...	3 beds \| 2 baths \| 1,449 sq.ft.	$360,000	Airbnb cash on cash: 3.81% Traditional cash on cash: 4.55% Airbnb Rental Income: $2561 Traditional Rental Income: $2195 Airbnb ROI: 3.81% Traditional ROI: 4.55%
201 S MAIN STREET Brooksville, FL Welcome to 201 South Main Street, one of Brooksvilleâs most admired historic homes and a...	4 beds \| 5 baths \| 1,872 sq.ft.	$450,000	Airbnb cash on cash: 8.52% Traditional cash on cash: 5.37% Airbnb Rental Income: $5422 Traditional Rental Income: $3002 Airbnb ROI: 8.52% Traditional ROI: 5.37%
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%
16084 STUR STREET Brooksville, FL CRAFTSMAN HOME ON HALF AN ACRE \| Brand New HVAC system JUST INSTALLED and a new termite bo...	3 beds \| 2 baths \| 1,995 sq.ft.	$425,000	Airbnb cash on cash: 3.45% Traditional cash on cash: 5.14% Airbnb Rental Income: $2561 Traditional Rental Income: $2618 Airbnb ROI: 3.45% Traditional ROI: 5.14%
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%
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%

Real Estate investment in Brooksville, FL

There are 315 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 October 2025, the average monthly cash on cash return in Brooksville is 5.00%. The average monthly rental income in Brooksville is $2,052.

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

There are 315 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 $2,052.

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%

4149 Gevalia Drive

Brooksville, FL

3 beds | 2 baths | 2,032 sq.ft.

$354,800

Airbnb cash on cash: 4.06%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $2561

Traditional Rental Income: $2145

Airbnb ROI: 4.06%

Traditional ROI: 4.66%

10110 Weeks Drive

Brooksville, FL

5 beds | N/A baths | 3,554 sq.ft.

$725,000

Airbnb cash on cash: N/A

Traditional cash on cash: 3.65%

Airbnb Rental Income: $null

Traditional Rental Income: $4601

Airbnb ROI: N/A

Traditional ROI: 3.65%

149 ROOSEVELT AVENUE

Brooksville, FL

3 beds | 2 baths | 1,296 sq.ft.

$299,000

Airbnb cash on cash: 4.94%

Traditional cash on cash: 5.45%

Airbnb Rental Income: $2561

Traditional Rental Income: $2088

Airbnb ROI: 4.94%

Traditional ROI: 5.45%

27151 HIAWATHA BOULEVARD

Brooksville, FL

3 beds | 2 baths | 1,634 sq.ft.

$655,000

Airbnb cash on cash: 1.58%

Traditional cash on cash: 2.03%

Airbnb Rental Income: $2561

Traditional Rental Income: $2221

Airbnb ROI: 1.58%

Traditional ROI: 2.03%

4367 BURNS ROAD

Brooksville, FL

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

$529,995

Airbnb cash on cash: 2.12%

Traditional cash on cash: 3.61%

Airbnb Rental Income: $2561

Traditional Rental Income: $2683

Airbnb ROI: 2.12%

Traditional ROI: 3.61%

8152 SOUTHERN PINES DRIVE

Brooksville, FL

3 beds | 2 baths | 1,640 sq.ft.

$207,900

Airbnb cash on cash: 3.32%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $2561

Traditional Rental Income: $2279

Airbnb ROI: 3.32%