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
8027 EASTERN CIRCLE DRIVE Brooksville, FL High Point Community 2 Bedroom 1.5 Baths- And A Carport- Enter The Home To The Kitchen Wit...	2 beds \| 2 baths \| 1,056 sq.ft.	$130,000	Airbnb cash on cash: 1.19% Traditional cash on cash: 9.95% Airbnb Rental Income: $791 Traditional Rental Income: $1566 Airbnb ROI: 1.19% Traditional ROI: 9.95%
4684 SOUTHERN VALLEY LOOP Brooksville, FL Enjoy resort-style living year-round in this meticulously maintained home located within t...	3 beds \| 2 baths \| 2,297 sq.ft.	$459,000	Airbnb cash on cash: -1.79% Traditional cash on cash: 2.19% Airbnb Rental Income: $1097 Traditional Rental Income: $2436 Airbnb ROI: -1.79% Traditional ROI: 2.19%
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.	$344,900	Airbnb cash on cash: 0.43% Traditional cash on cash: 6.13% Airbnb Rental Income: $1097 Traditional Rental Income: $2570 Airbnb ROI: 0.43% Traditional ROI: 6.13%
7186 LEXINGTON CIRCLE Brooksville, FL OVERSIZED LOT!!! Beautifully updated 2-bedroom, 2-bath. This home features a bright, open ...	2 beds \| 2 baths \| 1,102 sq.ft.	$285,000	Airbnb cash on cash: -0.47% Traditional cash on cash: 3.63% Airbnb Rental Income: $791 Traditional Rental Income: $1572 Airbnb ROI: -0.47% Traditional ROI: 3.63%
7020 ASHMONT AVENUE Brooksville, FL Beautifully updated SOLAR 4-bedroom, 2-bath Block home located in a quiet, family-friendly...	4 beds \| 2 baths \| 1,738 sq.ft.	$299,900	Airbnb cash on cash: 4.21% Traditional cash on cash: 5.43% Airbnb Rental Income: $2242 Traditional Rental Income: $2026 Airbnb ROI: 4.21% Traditional ROI: 5.43%
15489 Sonora Drive Brooksville, FL Discover this stunning MOVE-IN READY POOL home nestled in Deerfield Estates, featuring NO ...	3 beds \| 2 baths \| 1,651 sq.ft.	$335,000	Airbnb cash on cash: 0.17% Traditional cash on cash: 5.75% Airbnb Rental Income: $1097 Traditional Rental Income: $2484 Airbnb ROI: 0.17% Traditional ROI: 5.75%
240 Olive Street Brooksville, FL Recently updated with new double-pane, Energy Star-rated tinted windows and a fully resurf...	4 beds \| 3 baths \| 2,645 sq.ft.	$555,000	Airbnb cash on cash: 0.87% Traditional cash on cash: 4.93% Airbnb Rental Income: $2242 Traditional Rental Income: $3783 Airbnb ROI: 0.87% Traditional ROI: 4.93%
2043 TRILLIUM BLVD Brooksville, FL Welcome home to this stunning and meticulously well-maintained residence, where modern com...	3 beds \| 2 baths \| 2,144 sq.ft.	$334,999	Airbnb cash on cash: -0.17% Traditional cash on cash: 6% Airbnb Rental Income: $1097 Traditional Rental Income: $2669 Airbnb ROI: -0.17% Traditional ROI: 6%
8152 SOUTHERN PINES DRIVE Brooksville, FL Bright 2 Bedroom 2 Bath condo with a den at Southern Pines. Conveniently located off U.S H...	2 beds \| 2 baths \| 1,640 sq.ft.	$198,000	Airbnb cash on cash: -4.62% Traditional cash on cash: 6.51% Airbnb Rental Income: $791 Traditional Rental Income: $2562 Airbnb ROI: -4.62% Traditional ROI: 6.51%
7990 Southern Pines Drive Brooksville, FL Look no further! This well-maintained 2-bedroom, 2-bathroom third floor condo is located i...	2 beds \| 2 baths \| 1,674 sq.ft.	$199,900	Airbnb cash on cash: -3.4% Traditional cash on cash: 7.06% Airbnb Rental Income: $791 Traditional Rental Income: $2454 Airbnb ROI: -3.4% Traditional ROI: 7.06%
8341 HIGHPOINT BOULEVARD Brooksville, FL Fully Remodeled Highpoint Gem! Move right into this completely modernized, true 3-bedroom...	3 beds \| 2 baths \| 1,344 sq.ft.	$207,000	Airbnb cash on cash: 0.91% Traditional cash on cash: 7.28% Airbnb Rental Income: $1097 Traditional Rental Income: $1976 Airbnb ROI: 0.91% Traditional ROI: 7.28%
12124 Squeeze Avenue Brooksville, FL Working Farm! Experience the perfect blend of comfort, functionality, and true Nature Coas...	4 beds \| 3 baths \| 2,978 sq.ft.	$998,000	Airbnb cash on cash: -0.27% Traditional cash on cash: 1.4% Airbnb Rental Income: $2242 Traditional Rental Income: $3234 Airbnb ROI: -0.27% Traditional ROI: 1.4%
11031 NOTTINGHAM FOREST DRIVE Brooksville, FL Under contract-accepting backup offers. NO HOANO FLOODZONED AGRICULTURAL Discover...	3 beds \| 2 baths \| 1,920 sq.ft.	$415,000	Airbnb cash on cash: -0.97% Traditional cash on cash: 5.05% Airbnb Rental Income: $1097 Traditional Rental Income: $3066 Airbnb ROI: -0.97% Traditional ROI: 5.05%
12020 Pine Warbler Avenue Brooksville, FL 4Bed 3Bath Home on paved 1/2acre lot (mol) in the fast growing Royal Highland. This Home m...	4 beds \| 3 baths \| 1,831 sq.ft.	$339,900	Airbnb cash on cash: 3.2% Traditional cash on cash: 5.91% Airbnb Rental Income: $2242 Traditional Rental Income: $2545 Airbnb ROI: 3.2% Traditional ROI: 5.91%
5201 NEFF LAKE RD Brooksville, FL Secluded Pool Home on 5 Private Acres in Brooksville! Escape to your own peaceful oasis! N...	3 beds \| 2 baths \| 2,014 sq.ft.	$525,000	Airbnb cash on cash: -1.07% Traditional cash on cash: 3.6% Airbnb Rental Income: $1097 Traditional Rental Income: $3017 Airbnb ROI: -1.07% Traditional ROI: 3.6%
8578 PINETOP RIDGE LANE Brooksville, FL Under contract-accepting backup offers. Short Sale. THIS HOME IS NOW OFFERED AS A "SHORT S...	3 beds \| 2 baths \| 1,735 sq.ft.	$250,000	Airbnb cash on cash: 0.53% Traditional cash on cash: 7.39% Airbnb Rental Income: $1097 Traditional Rental Income: $2344 Airbnb ROI: 0.53% Traditional ROI: 7.39%
15663 DURANGO CIRCLE Brooksville, FL Move-in ready and thoughtfully upgraded throughout! This impressive 4-bedroom, 2.5-bath ho...	4 beds \| 3 baths \| 2,039 sq.ft.	$350,000	Airbnb cash on cash: 2.34% Traditional cash on cash: 5.11% Airbnb Rental Income: $2242 Traditional Rental Income: $2588 Airbnb ROI: 2.34% Traditional ROI: 5.11%
23125 Jacobson Road Brooksville, FL Welcome to your own private slice of country paradise! Situated on 4.7 acres MOL of beauti...	3 beds \| 2 baths \| 1,888 sq.ft.	$599,900	Airbnb cash on cash: -0.72% Traditional cash on cash: 2.61% Airbnb Rental Income: $1097 Traditional Rental Income: $2589 Airbnb ROI: -0.72% Traditional ROI: 2.61%
951 Nodding Shade Drive Brooksville, FL Your Dream Home with Space, Style & Serenity -- Welcome to 951 Nodding Shade Dr in Trilliu...	4 beds \| 3 baths \| 2,663 sq.ft.	$305,000	Airbnb cash on cash: 2.49% Traditional cash on cash: 8.2% Airbnb Rental Income: $2242 Traditional Rental Income: $3318 Airbnb ROI: 2.49% Traditional ROI: 8.2%
7228 CRESTED ORCHID DRIVE Brooksville, FL Welcome Home To This Beautifully Maintained Property Located In The Desirable Sherman Hill...	3 beds \| 2 baths \| 1,925 sq.ft.	$300,000	Airbnb cash on cash: 1.02% Traditional cash on cash: 6.42% Airbnb Rental Income: $1097 Traditional Rental Income: $2252 Airbnb ROI: 1.02% Traditional ROI: 6.42%
27016 ANTHONY AVENUE Brooksville, FL Under contract-accepting backup offers. Price Improvement **VA Assumable Loan Availab...	3 beds \| 3 baths \| 1,606 sq.ft.	$276,000	Airbnb cash on cash: 0.34% Traditional cash on cash: 6.52% Airbnb Rental Income: $1097 Traditional Rental Income: $2335 Airbnb ROI: 0.34% Traditional ROI: 6.52%
15114 Durango Circle Brooksville, FL Lovely 3 bedroom, 2 bathroom, 2 car attached garage home located in the gated community of...	3 beds \| 2 baths \| 1,861 sq.ft.	$225,900	Airbnb cash on cash: -0.56% Traditional cash on cash: 6.76% Airbnb Rental Income: $1097 Traditional Rental Income: $2290 Airbnb ROI: -0.56% Traditional ROI: 6.76%
5198 Legend Hills Lane Brooksville, FL Experience Timeless Luxury and Masterful Craftsmanship Welcome to this extraordinary custo...	4 beds \| 3 baths \| 3,391 sq.ft.	$895,000	Airbnb cash on cash: 0.27% Traditional cash on cash: 3.05% Airbnb Rental Income: $2242 Traditional Rental Income: $4003 Airbnb ROI: 0.27% Traditional ROI: 3.05%
11419 OLD CRYSTAL RIVER ROAD Brooksville, FL $25,000 Price Improvement! 14.6 Beautiful Acres in Brooksville, Florida â Updated Home w...	3 beds \| 2 baths \| 2,257 sq.ft.	$1,100,000	Airbnb cash on cash: -0.86% Traditional cash on cash: 1.09% Airbnb Rental Income: $1097 Traditional Rental Income: $2716 Airbnb ROI: -0.86% Traditional ROI: 1.09%
14111 Race Avenue Brooksville, FL Welcome home to this beautifully maintained 2021-built, 4-bedroom, 2-bathroom property. Of...	4 beds \| 2 baths \| 1,754 sq.ft.	$340,000	Airbnb cash on cash: 3.83% Traditional cash on cash: 5.64% Airbnb Rental Income: $2242 Traditional Rental Income: $2258 Airbnb ROI: 3.83% Traditional ROI: 5.64%
12054 ROYAL DRIVE Brooksville, FL Under contract-accepting backup offers. A rare opportunity to own a home in the exclusive ...	4 beds \| 3 baths \| 2,864 sq.ft.	$624,900	Airbnb cash on cash: 0.83% Traditional cash on cash: 3.78% Airbnb Rental Income: $2242 Traditional Rental Income: $3402 Airbnb ROI: 0.83% Traditional ROI: 3.78%
5127 SECRETARIAT RUN Brooksville, FL Step into this meticulously upgraded 3-bedroom, 2-bathroom gem located in the prestigious ...	3 beds \| 2 baths \| 2,031 sq.ft.	$390,000	Airbnb cash on cash: -0.65% Traditional cash on cash: 4.54% Airbnb Rental Income: $1097 Traditional Rental Income: $2623 Airbnb ROI: -0.65% Traditional ROI: 4.54%
19443 Fort Dade Avenue Brooksville, FL Welcome Home to this cozy and charming 4-bedroom, 2-bath ranch-style retreat nestled on a ...	4 beds \| 2 baths \| 1,400 sq.ft.	$215,000	Airbnb cash on cash: 5.82% Traditional cash on cash: 6.74% Airbnb Rental Income: $2242 Traditional Rental Income: $1868 Airbnb ROI: 5.82% Traditional ROI: 6.74%
27183 THORNCREST AVENUE Brooksville, FL $35,000 PRICE REDUCTION! Discover the perfect blend of comfort, convenience, and Florid...	3 beds \| 2 baths \| 1,099 sq.ft.	$144,900	Airbnb cash on cash: 1.88% Traditional cash on cash: 11.08% Airbnb Rental Income: $1097 Traditional Rental Income: $2002 Airbnb ROI: 1.88% Traditional ROI: 11.08%
8279 SUNSHINE GROVE RD Brooksville, FL 21-acre multi-use property with existing residences and extensive frontage on Sunshine Gro...	2 beds \| 2 baths \| 1,326 sq.ft.	$4,250,000	Airbnb cash on cash: -1% Traditional cash on cash: -0.47% Airbnb Rental Income: $791 Traditional Rental Income: $2539 Airbnb ROI: -1% Traditional ROI: -0.47%
14210 WAKE ROBIN DRIVE Brooksville, FL Under contract-accepting backup offers. Short Sale. SHORT SALE APPROVED AT LIST PRICE!!!!W...	4 beds \| 3 baths \| 2,396 sq.ft.	$265,900	Airbnb cash on cash: 2.95% Traditional cash on cash: 7.28% Airbnb Rental Income: $2242 Traditional Rental Income: $2767 Airbnb ROI: 2.95% Traditional ROI: 7.28%
13517 CITRUS WAY Brooksville, FL Short Sale. Short Sale, BANK APPROVED. Beautiful just under 5-acre, fenced, park like set...	3 beds \| 3 baths \| 2,789 sq.ft.	$488,500	Airbnb cash on cash: 0.29% Traditional cash on cash: 4.91% Airbnb Rental Income: $1097 Traditional Rental Income: $2838 Airbnb ROI: 0.29% Traditional ROI: 4.91%
27178 HICKORY HILL ROAD Brooksville, FL Under contract-accepting backup offers. Short Sale. BANKRUPTCY HOME! Opportunity Knocks On...	4 beds \| 3 baths \| 2,500 sq.ft.	$399,999	Airbnb cash on cash: 1.33% Traditional cash on cash: 7.01% Airbnb Rental Income: $2242 Traditional Rental Income: $3809 Airbnb ROI: 1.33% Traditional ROI: 7.01%
1707 Trillium Boulevard Brooksville, FL Perfectly positioned, this beautifully maintained 2016 residence offers a comfortable blen...	3 beds \| 2 baths \| 1,978 sq.ft.	$319,500	Airbnb cash on cash: 0.07% Traditional cash on cash: 6.07% Airbnb Rental Income: $1097 Traditional Rental Income: $2528 Airbnb ROI: 0.07% Traditional ROI: 6.07%
7220 SHERMAN HILLS BOULEVARD Brooksville, FL Short Sale. Exceptional opportunity to own a 3 bedroom, 2 bath, & 2-car garage home locate...	4 beds \| 2 baths \| 1,846 sq.ft.	$295,000	Airbnb cash on cash: 3.44% Traditional cash on cash: 5.78% Airbnb Rental Income: $2242 Traditional Rental Income: $2329 Airbnb ROI: 3.44% Traditional ROI: 5.78%
4522 LISETTE CIRCLE Brooksville, FL A must see, Beautiful 4-bedroom, 3-bathroom home located in the Hernando Oaks Community. ...	4 beds \| 3 baths \| 1,780 sq.ft.	$399,900	Airbnb cash on cash: 2.03% Traditional cash on cash: 3.95% Airbnb Rental Income: $2242 Traditional Rental Income: $2399 Airbnb ROI: 2.03% Traditional ROI: 3.95%
4698 HICKORY OAK DRIVE Brooksville, FL One of the best priced homes currently on the market in Southern Hills! This 4 year old on...	4 beds \| 3 baths \| 2,667 sq.ft.	$569,950	Airbnb cash on cash: 0.16% Traditional cash on cash: 2.72% Airbnb Rental Income: $2242 Traditional Rental Income: $3041 Airbnb ROI: 0.16% Traditional ROI: 2.72%
31008 SATINLEAF RUN Brooksville, FL Imagine 31008 Satinleaf Run, a residence with recent updates including fresh interior pain...	3 beds \| 2 baths \| 1,546 sq.ft.	$249,000	Airbnb cash on cash: -0.32% Traditional cash on cash: 5.71% Airbnb Rental Income: $1097 Traditional Rental Income: $2142 Airbnb ROI: -0.32% Traditional ROI: 5.71%
30067 FEDORA CIRCLE Brooksville, FL Welcome to this beautifully maintained newer construction home in the desirable Trilby Cro...	3 beds \| 2 baths \| 1,459 sq.ft.	$289,900	Airbnb cash on cash: -0.24% Traditional cash on cash: 4.05% Airbnb Rental Income: $1097 Traditional Rental Income: $1896 Airbnb ROI: -0.24% Traditional ROI: 4.05%
19333 FORT KING RUN Brooksville, FL Welcome to Luxury! This move-in ready home is located in the desirable 55+ Gated Community...	2 beds \| 2 baths \| 1,320 sq.ft.	$327,000	Airbnb cash on cash: -3.11% Traditional cash on cash: 0.95% Airbnb Rental Income: $791 Traditional Rental Income: $1720 Airbnb ROI: -3.11% Traditional ROI: 0.95%

Real Estate investment in Brooksville, FL

There are 252 properties for sale in the city of Brooksville . The median list price in Brooksville is $407,916 and the average price per square foot is $237. In July 2026, the average monthly cash on cash return in Brooksville is 5.00%. The average monthly rental income in Brooksville is $1,844.

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

There are 252 investment properties available for sale in Brooksville.

In 2026, the best neighborhood to buy investment property is Brooksville.

The ROI for Short-Term is higher than the Long-Term in Brooksville with average rental income of $886.

Your search for investment property begins and ends here

Investment Property for Sale in Brooksville, FL

8027 EASTERN CIRCLE DRIVE

Brooksville, FL

2 beds | 2 baths | 1,056 sq.ft.

$130,000

Airbnb cash on cash: 1.19%

Traditional cash on cash: 9.95%

Airbnb Rental Income: $791

Traditional Rental Income: $1566

Airbnb ROI: 1.19%

Traditional ROI: 9.95%

4684 SOUTHERN VALLEY LOOP

Brooksville, FL

3 beds | 2 baths | 2,297 sq.ft.

$459,000

Airbnb cash on cash: -1.79%

Traditional cash on cash: 2.19%

Airbnb Rental Income: $1097

Traditional Rental Income: $2436

Airbnb ROI: -1.79%

Traditional ROI: 2.19%

4149 Gevalia Drive

Brooksville, FL

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

$344,900

Airbnb cash on cash: 0.43%

Traditional cash on cash: 6.13%

Airbnb Rental Income: $1097

Traditional Rental Income: $2570

Airbnb ROI: 0.43%

Traditional ROI: 6.13%

7186 LEXINGTON CIRCLE

Brooksville, FL

2 beds | 2 baths | 1,102 sq.ft.

$285,000

Airbnb cash on cash: -0.47%

Traditional cash on cash: 3.63%

Airbnb Rental Income: $791

Traditional Rental Income: $1572

Airbnb ROI: -0.47%

Traditional ROI: 3.63%

7020 ASHMONT AVENUE

Brooksville, FL

4 beds | 2 baths | 1,738 sq.ft.

$299,900

Airbnb cash on cash: 4.21%

Traditional cash on cash: 5.43%

Airbnb Rental Income: $2242

Traditional Rental Income: $2026

Airbnb ROI: 4.21%

Traditional ROI: 5.43%

15489 Sonora Drive

Brooksville, FL

3 beds | 2 baths | 1,651 sq.ft.

$335,000

Airbnb cash on cash: 0.17%

Traditional cash on cash: 5.75%

Airbnb Rental Income: $1097

Traditional Rental Income: $2484

Airbnb ROI: 0.17%

Traditional ROI: 5.75%

240 Olive Street

Brooksville, FL

4 beds | 3 baths | 2,645 sq.ft.

$555,000

Airbnb cash on cash: 0.87%

Traditional cash on cash: 4.93%

Airbnb Rental Income: $2242

Traditional Rental Income: $3783

Airbnb ROI: 0.87%

Traditional ROI: 4.93%

2043 TRILLIUM BLVD

Brooksville, FL

3 beds | 2 baths | 2,144 sq.ft.

$334,999

Airbnb cash on cash: -0.17%

Traditional cash on cash: 6%

Airbnb Rental Income: $1097

Traditional Rental Income: $2669

Airbnb ROI: -0.17%