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.

Woodlawn Investment Property for Sale in Brooksville, FL

Search for Woodlawn Investment Property for Sale in Brooksville, Florida. Browse all of Mashvisor’s Woodlawn Investment Property listings and other investment property types including Single Family Homes, Multi Family Homes, Condos, Townhouses and Other Homes.

Showing 292 Woodlawn Investment Property listings of over 500,000 total investment properties for sale. Visit Mashvisor.com to all investment properties.

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
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.	$349,900	Airbnb cash on cash: 1.92% Traditional cash on cash: 4.73% Airbnb Rental Income: $1692 Traditional Rental Income: $2145 Airbnb ROI: 1.92% Traditional ROI: 4.73%
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.	$289,000	Airbnb cash on cash: 2.48% Traditional cash on cash: 5.67% Airbnb Rental Income: $1692 Traditional Rental Income: $2088 Airbnb ROI: 2.48% Traditional ROI: 5.67%
653 PETAL MIST LANE Brooksville, FL Move-in ready and located in the highly sought-after Trillium community, this beautiful 3-...	3 beds \| 2 baths \| 2,058 sq.ft.	$354,900	Airbnb cash on cash: 0.99% Traditional cash on cash: 3.95% Airbnb Rental Income: $1692 Traditional Rental Income: $2207 Airbnb ROI: 0.99% Traditional ROI: 3.95%
398 Sea Holly Drive Brooksville, FL Must see this Pool Home with its own backyard oasis! 3-4 bedroom (flex room currently used...	3 beds \| 2 baths \| 1,814 sq.ft.	$399,000	Airbnb cash on cash: 0.7% Traditional cash on cash: 4.03% Airbnb Rental Income: $1692 Traditional Rental Income: $2468 Airbnb ROI: 0.7% Traditional ROI: 4.03%
4367 BURNS ROAD Brooksville, FL Under contract-accepting backup offers. Welcome to Your Private Paradise! Discover the p...	3 beds \| 2 baths \| 1,982 sq.ft.	$447,000	Airbnb cash on cash: 0.96% Traditional cash on cash: 4.46% Airbnb Rental Income: $1692 Traditional Rental Income: $2683 Airbnb ROI: 0.96% Traditional ROI: 4.46%
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.	$349,999	Airbnb cash on cash: 1.3% Traditional cash on cash: 5.01% Airbnb Rental Income: $1692 Traditional Rental Income: $2441 Airbnb ROI: 1.3% Traditional ROI: 5.01%
2279 CROSS TEE COURT Brooksville, FL Welcome to this charming 3-bedroom, 2-bath home built in 2005 with a ample 0.27 lot size ,...	3 beds \| 2 baths \| 1,814 sq.ft.	$299,900	Airbnb cash on cash: 1.46% Traditional cash on cash: 4.66% Airbnb Rental Income: $1692 Traditional Rental Income: $2127 Airbnb ROI: 1.46% Traditional ROI: 4.66%
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.	$207,900	Airbnb cash on cash: -4% Traditional cash on cash: 4.73% Airbnb Rental Income: $896 Traditional Rental Income: $2279 Airbnb ROI: -4% Traditional ROI: 4.73%
7990 Southern Pines Dr 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: -2.94% Traditional cash on cash: 7.11% Airbnb Rental Income: $896 Traditional Rental Income: $2463 Airbnb ROI: -2.94% Traditional ROI: 7.11%
7428 Harlow Street Brooksville, FL Welcome to this beautifully renovated 2-bedroom, 1.5-bath home located in the gated, resor...	2 beds \| 2 baths \| 898 sq.ft.	$151,510	Airbnb cash on cash: 1.31% Traditional cash on cash: 8.47% Airbnb Rental Income: $896 Traditional Rental Income: $1595 Airbnb ROI: 1.31% Traditional ROI: 8.47%
5149 Jennings Trl Brooksville, FL Love a great golf course, a scenic home on a pond and an amazing community? Just reduced. ...	3 beds \| 3 baths \| 2,322 sq.ft.	$474,000	Airbnb cash on cash: -0.87% Traditional cash on cash: 2.68% Airbnb Rental Income: $1692 Traditional Rental Income: $2792 Airbnb ROI: -0.87% Traditional ROI: 2.68%
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: 1.11% Traditional cash on cash: 10.87% Airbnb Rental Income: $896 Traditional Rental Income: $2117 Airbnb ROI: 1.11% Traditional ROI: 10.87%
16154 Ft Myers Street Brooksville, FL Priced to Sell this Beautifully updated 3-bedroom, 2-bath mobile home featuring brand-new ...	3 beds \| 2 baths \| 1,440 sq.ft.	$199,500	Airbnb cash on cash: 3.84% Traditional cash on cash: 8.57% Airbnb Rental Income: $1692 Traditional Rental Income: $2117 Airbnb ROI: 3.84% Traditional ROI: 8.57%
1304 Candlelight Blvd Brooksville, FL This beautifully cared-for 4-bedroom, 2-bath custom Alexander home offers quality, comfort...	4 beds \| 2 baths \| 2,023 sq.ft.	$425,000	Airbnb cash on cash: 7.66% Traditional cash on cash: 3.06% Airbnb Rental Income: $5422 Traditional Rental Income: $2496 Airbnb ROI: 7.66% Traditional ROI: 3.06%
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: 5.29% Traditional cash on cash: 7.99% Airbnb Rental Income: $1692 Traditional Rental Income: $1670 Airbnb ROI: 5.29% Traditional ROI: 7.99%
11031 Nottingham Forest Dr Brooksville, FL Discover the potential in this spacious 3-bedroom, 2-bath home nestled on 1.3 beautiful ac...	3 beds \| 2 baths \| 1,920 sq.ft.	$460,000	Airbnb cash on cash: 0.13% Traditional cash on cash: 3.56% Airbnb Rental Income: $1692 Traditional Rental Income: $2763 Airbnb ROI: 0.13% Traditional ROI: 3.56%
19906 Tattnall Way Brooksville, FL This remarkable residence seamlessly blends modern elegance and convenience, offering gene...	4 beds \| 3 baths \| 3,130 sq.ft.	$514,000	Airbnb cash on cash: 5.96% Traditional cash on cash: 3.44% Airbnb Rental Income: $5422 Traditional Rental Income: $3105 Airbnb ROI: 5.96% Traditional ROI: 3.44%
4024 Culbreath Road Brooksville, FL Bring all offers! Beautiful home on 2 1/2 acres in desirable area. This 3 bedroom/2 bath h...	3 beds \| 2 baths \| 2,700 sq.ft.	$464,900	Airbnb cash on cash: 0.14% Traditional cash on cash: 4.21% Airbnb Rental Income: $1692 Traditional Rental Income: $2992 Airbnb ROI: 0.14% Traditional ROI: 4.21%
14392 Wake Robin Drive Brooksville, FL This light and bright split-plan home features a living room, formal dining room, and a fa...	3 beds \| 2 baths \| 1,814 sq.ft.	$289,000	Airbnb cash on cash: 1.78% Traditional cash on cash: 5.3% Airbnb Rental Income: $1692 Traditional Rental Income: $2178 Airbnb ROI: 1.78% Traditional ROI: 5.3%
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.	$559,999	Airbnb cash on cash: -0.11% Traditional cash on cash: 2.84% Airbnb Rental Income: $1692 Traditional Rental Income: $2764 Airbnb ROI: -0.11% Traditional ROI: 2.84%
16481 Oakview Dr Istachatta, FL Discover the perfect blend of peaceful country living and modern comfort on nearly 5 fence...	4 beds \| 2 baths \| 2,280 sq.ft.	$399,900	Airbnb cash on cash: 8.88% Traditional cash on cash: 4.38% Airbnb Rental Income: $5422 Traditional Rental Income: $2599 Airbnb ROI: 8.88% Traditional ROI: 4.38%
5324 Southern Valley Loop Brooksville, FL *OPEN HOUSE SATURDAY NOV. 29th 12-2PM *PRICE IMPROVEMENT! Welcome to this exquisite 3-...	3 beds \| 4 baths \| 3,189 sq.ft.	$620,000	Airbnb cash on cash: -1.45% Traditional cash on cash: 2.93% Airbnb Rental Income: $1692 Traditional Rental Income: $3760 Airbnb ROI: -1.45% Traditional ROI: 2.93%
996 SCARLET PLUME LANE Brooksville, FL One or more photo(s) has been virtually staged. Take advantage of an assumable mortgage at...	3 beds \| 2 baths \| 1,978 sq.ft.	$339,900	Airbnb cash on cash: 1.32% Traditional cash on cash: 5.32% Airbnb Rental Income: $1692 Traditional Rental Income: $2497 Airbnb ROI: 1.32% Traditional ROI: 5.32%
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: 0.73% Traditional cash on cash: 5.18% Airbnb Rental Income: $896 Traditional Rental Income: $1526 Airbnb ROI: 0.73% 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.	$349,900	Airbnb cash on cash: 1.38% Traditional cash on cash: 4.68% Airbnb Rental Income: $1692 Traditional Rental Income: $2305 Airbnb ROI: 1.38% Traditional ROI: 4.68%
840 LAURELRIDGE COURT Brooksville, FL BEAUTIFUL HOME IN THE CITY OF BROOKSVILLE - our real little Hallmark Town!! Built in 2018 ...	3 beds \| 2 baths \| 1,590 sq.ft.	$325,000	Airbnb cash on cash: 1.59% Traditional cash on cash: 5.03% Airbnb Rental Income: $1692 Traditional Rental Income: $2272 Airbnb ROI: 1.59% Traditional ROI: 5.03%
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.	$344,900	Airbnb cash on cash: 1.04% Traditional cash on cash: 5.1% Airbnb Rental Income: $1692 Traditional Rental Income: $2538 Airbnb ROI: 1.04% Traditional ROI: 5.1%
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: 3.27% Traditional cash on cash: 1.14% Airbnb Rental Income: $5247 Traditional Rental Income: $2408 Airbnb ROI: 3.27% Traditional ROI: 1.14%
11419 OLD CRYSTAL RIVER ROAD Brooksville, FL Rare Find! 14.6 Beautiful Acres in Brooksville with an Updated Home and Equestrian Ameniti...	3 beds \| 2 baths \| 2,257 sq.ft.	$1,125,000	Airbnb cash on cash: -0.39% Traditional cash on cash: 0.95% Airbnb Rental Income: $1692 Traditional Rental Income: $2615 Airbnb ROI: -0.39% Traditional ROI: 0.95%
9202 SOUTHERN CHARM CIRCLE Brooksville, FL Move-in ready villa in the centrally located Spring Ridge community! This updated 3-bedroo...	3 beds \| 2 baths \| 1,500 sq.ft.	$265,000	Airbnb cash on cash: 1.94% Traditional cash on cash: 5.29% Airbnb Rental Income: $1692 Traditional Rental Income: $2061 Airbnb ROI: 1.94% Traditional ROI: 5.29%
27183 THORNCREST AVENUE Brooksville, FL Discover the perfect blend of comfort, convenience, and Florida charm at 27183 Thorncrest ...	3 beds \| 2 baths \| 1,099 sq.ft.	$180,000	Airbnb cash on cash: 4.23% Traditional cash on cash: 6.14% Airbnb Rental Income: $1692 Traditional Rental Income: $1549 Airbnb ROI: 4.23% Traditional ROI: 6.14%
23328 Christian Cir Brooksville, FL One or more photo(s) has been virtually staged. Beautiful Custom Home on Oversized Lot! NE...	3 beds \| 2 baths \| 2,223 sq.ft.	$469,000	Airbnb cash on cash: 0.71% Traditional cash on cash: 3.98% Airbnb Rental Income: $1692 Traditional Rental Income: $2654 Airbnb ROI: 0.71% Traditional ROI: 3.98%
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.	$289,000	Airbnb cash on cash: 1.72% Traditional cash on cash: 4.62% Airbnb Rental Income: $1692 Traditional Rental Income: $2011 Airbnb ROI: 1.72% Traditional ROI: 4.62%
6479 BARCELONA BOULEVARD Brooksville, FL Welcome to this wonderful 2 bedroom, 2 bathroom home offering 1,144 square feet of comfort...	2 beds \| 2 baths \| 1,144 sq.ft.	$239,900	Airbnb cash on cash: 0.04% Traditional cash on cash: 5.51% Airbnb Rental Income: $896 Traditional Rental Income: $1799 Airbnb ROI: 0.04% Traditional ROI: 5.51%
13517 Citrus Way Brooksville, FL Short Sale. Short Sale. Beautiful just under 5-acre, fenced, park like setting surrounds ...	3 beds \| 3 baths \| 2,789 sq.ft.	$475,000	Airbnb cash on cash: 1.27% Traditional cash on cash: 4.66% Airbnb Rental Income: $1692 Traditional Rental Income: $2838 Airbnb ROI: 1.27% Traditional ROI: 4.66%
27178 HICKORY HILL ROAD Brooksville, FL Short Sale. BANKRUPTCY HOME! Opportunity Knocks On This 10Â± Acre AG-Zoned Homesite In Bro...	4 beds \| 3 baths \| 2,500 sq.ft.	$399,999	Airbnb cash on cash: 8.4% Traditional cash on cash: 6.3% Airbnb Rental Income: $5422 Traditional Rental Income: $3542 Airbnb ROI: 8.4% Traditional ROI: 6.3%

Your search for investment property begins and ends here

Woodlawn Investment Property for Sale in Brooksville, FL

4149 Gevalia Drive

Brooksville, FL

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

$349,900

Airbnb cash on cash: 1.92%

Traditional cash on cash: 4.73%

Airbnb Rental Income: $1692

Traditional Rental Income: $2145

Airbnb ROI: 1.92%

Traditional ROI: 4.73%

149 ROOSEVELT AVENUE

Brooksville, FL

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

$289,000

Airbnb cash on cash: 2.48%

Traditional cash on cash: 5.67%

Airbnb Rental Income: $1692

Traditional Rental Income: $2088

Airbnb ROI: 2.48%

Traditional ROI: 5.67%

653 PETAL MIST LANE

Brooksville, FL

3 beds | 2 baths | 2,058 sq.ft.

$354,900

Airbnb cash on cash: 0.99%

Traditional cash on cash: 3.95%

Airbnb Rental Income: $1692

Traditional Rental Income: $2207

Airbnb ROI: 0.99%

Traditional ROI: 3.95%

398 Sea Holly Drive

Brooksville, FL

3 beds | 2 baths | 1,814 sq.ft.

$399,000

Airbnb cash on cash: 0.7%

Traditional cash on cash: 4.03%

Airbnb Rental Income: $1692

Traditional Rental Income: $2468

Airbnb ROI: 0.7%

Traditional ROI: 4.03%

4367 BURNS ROAD

Brooksville, FL

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

$447,000

Airbnb cash on cash: 0.96%

Traditional cash on cash: 4.46%

Airbnb Rental Income: $1692

Traditional Rental Income: $2683

Airbnb ROI: 0.96%

Traditional ROI: 4.46%

2043 TRILLIUM BLVD

Brooksville, FL

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

$349,999

Airbnb cash on cash: 1.3%

Traditional cash on cash: 5.01%

Airbnb Rental Income: $1692

Traditional Rental Income: $2441

Airbnb ROI: 1.3%

Traditional ROI: 5.01%

2279 CROSS TEE COURT

Brooksville, FL

3 beds | 2 baths | 1,814 sq.ft.

$299,900

Airbnb cash on cash: 1.46%

Traditional cash on cash: 4.66%

Airbnb Rental Income: $1692

Traditional Rental Income: $2127

Airbnb ROI: 1.46%

Traditional ROI: 4.66%

8152 SOUTHERN PINES DRIVE

Brooksville, FL

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

$207,900

Airbnb cash on cash: -4%

Traditional cash on cash: 4.73%

Airbnb Rental Income: $896

Traditional Rental Income: $2279

Airbnb ROI: -4%