Brooksville Real Estate Search

Brooksville 6+ Bedroom Properties for Sale

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Newest Brooksville 6+ Bedrooms Properties for Sale

10484 Gypsy Avenue, Brooksville
$2,900,000
8 Beds ⋅ 5 Baths ⋅ W7890040 MLS
Virtually Staged. HORSES & HORSEPOWER | 5 ACRES | 8 BEDROOMS | 9-STALL HORSE BARN | 40x80 GARAGE > Why choose between your love of horses and horsepower when you can have both? Tucked behind a private gated entrance on 5 BEAUTIFUL ACRES, this custom estate brings together luxury living, incredible equestrian facilities, and garage space that's hard to find anywhere else. The impressive two-story home offers 8 BEDROOMS, 4.5 BATHROOMS, TWO HOME OFFICES, a dedicated HOME THEATER + A SEPARATE BAR/GAME ROOM AREA, private POOL AND SPA, and beautifully designed spaces throughout. Outside, you'll find a 9-STALL CENTER-AISLE BARN, multiple FENCED PASTURES, a massive 40x80 AIR-CONDITIONED GARAGE WITH LIFT, 2 additional garages, and plenty of room to enjoy the property. NO HOA From the inviting covered front porch to the dramatic two-story foyer, this custom home is filled with beautiful architectural details, soaring ceilings, and spacious living areas. The family room features gorgeous wood-beamed ceilings and a striking stone GAS FIREPLACE, while the kitchen offers custom wood cabinetry, granite countertops, a large center island with prep sink, copper sink, walk-in pantry, and ALL NEW KITCHEN APPLIANCES IN 2026, including a FORNO range and French-door wall oven. Upstairs, the expansive primary suite includes an oversized walk-in closet, and a beautifully appointed bathroom with jetted soaking tub, large walk-in shower, and dual vanities. With EIGHT BEDROOMS throughout the home, there's room for a variety of living arrangements and uses. The dedicated HOME THEATER includes all furnishings and equipment, which convey with the property, while the separate BAR/GAME ROOM features a newly added ITALIAN-BUILT BAR that also stays. The outdoor living spaces are just as impressive! A beautiful HEATED POOL & SPA take center stage, surrounded by a spacious covered lanai, matching poolside pavilion, and a BRAND-NEW OUTDOOR KITCHEN. For the equestrian enthusiast, the 36x96 CENTER-AISLE HORSE BARN is thoughtfully equipped with 9 spacious 12x12 stalls, each featuring an AUTOMATIC FEEDER, along with feed and tack rooms, wash station, covered trailer parking, and RV hookup. The property includes FOUR SEPARATE PASTURES, including a riding pasture, with cross-fencing, no-climb fencing, and three covered lean-tos for shelter. And for the horsepower? The MASSIVE 40x80 DETACHED GARAGE is a standout feature all on its own! Designed with car collectors and hobbyists in mind, this impressive building features a VEHICLE LIFT, pull-through bay doors, heavy-duty concrete floors, and TWO 3-TON AC MINI-SPLITS. With approximately 3,200 square feet of garage space, there's room for an extensive vehicle collection, workshop, recreational equipment, or all of the above. Need even more space? You'll also find an additional 3-CAR DETACHED GARAGE, a large pole barn, and an attached 2-car garage with a 16x23 AIR-CONDITIONED GYM/FLEX SPACE. Additional features include a NEW ROOF IN 2019, FIVE AC UNITS with TWO REPLACED IN 2026, a paved driveway, private gated entrance, and beautifully maintained grounds. Located in Weeki Wachee, you'll enjoy the privacy and freedom of acreage living while remaining convenient to shopping, dining, schools, and the Suncoast Parkway for easy access to Tampa. Spend your weekends kayaking the crystal-clear Weeki Wachee River or boating along the Nature Coast. HORSES & HORSEPOWER... Why settle for one when you can have both?

10484 Gypsy Avenue, Brooksville

Listing courtesy of MERIDIAN REAL ESTATE. Contact: 352-585-6317

27255 Hickory Hill Rd, Brooksville
$3,499,900
6 Beds ⋅ 6 Baths ⋅ 2261085 MLS
A rare opportunity to own a truly exceptional 24-acre Brooksville estate offering an unmatched combination of luxury residential living, equestrian potential, industrial capability, and future development flexibility. Designed for both grand-scale entertaining and everyday comfort, the custom 6,700 sq ft main residence features 5 bedrooms, including 3 suite-style bedrooms, 5.5 bathrooms, large executive office, and expansive living spaces including a living, sitting and great room complete with a full bar. The home is enhanced by 3 fireplaces and an impressive 2,500 sq ft two-story wraparound deck spanning three sides of the residence, along with a pool deck and hot tub designed for outdoor relaxation and entertaining. The home captures panoramic natural surroundings, privacy, and exceptional airflow. For the automotive enthusiast or serious collector, the estate offers extraordinary, fully scalable vehicle capacity exceeding 100 cars in total across multiple structures. The eight-car garage with integrated paint booth provides space for approx. 9 vehicles while also including dedicated storage and a professional-grade paint stall. The 4,800 sq ft high-bay building with 20-foot ceilings and oversized doors can accommodate approximately 18-22 vehicles, RVs, or heavy equipment. The crown jewel is the 24,500 sq ft commercial-grade building, which can house approximately 65-80 vehicles, offering exceptional clear-span interior space ideal for collectors, storage operations, or automotive business use. Additional structures include a 4,800 sq ft high-bay building and a 24,500 sq ft wind-rated commercial-grade facility constructed approximately 12 years ago, featuring 16-foot eaves, a 140 MPH wind rating, and flexible interior layout suitable for industrial, logistics, storage, or event use--making it one of the largest privately owned structures of its kind in the region. Equestrian amenities include a small horse stable and ample acreage suitable for paddocks, riding areas, or expansion. Extensive environmental due diligence has been completed, including a Wetlands Jurisdictional Delineation, Protected Wildlife Species Survey, and full property survey, significantly reducing development risk and streamlining future permitting or subdivision opportunities. The property also features a highly flexible subdivision plan allowing for up to five total parcels, including a primary estate parcel with the main residence and supporting structures, a dedicated commercial/industrial parcel featuring the 24,500 sq ft building, and three additional residential lots ideal for custom homes, guest estates, or resale potential. Offering nearly 36,000 sq ft of enclosed structures across the estate and unmatched vehicle storage capacity exceeding 100 cars, this property is ideally suited for private estate ownership, multi-generational compound living, agricultural or equestrian operations, or a high-value investment and redevelopment strategy. A truly one-of-a-kind!

27255 Hickory Hill Rd, Brooksville

Listing courtesy of Paid Reciprocal Office. Contact:

26307 Mountain Lake Road, Brooksville
$2,250,000
6 Beds ⋅ 6 Baths ⋅ TB8548729 MLS
21 ACRES, A SPACIOUS ESTATE HOME, TWO SPRING-FED PONDS, AND A PRIVATE POOL — ALL IN BROOKSVILLE! Discover the possibilities at 26307 Mountain Lake Road! Offered at $2,250,000, this property combines 21 acres with a multi-level residence featuring 6 bedrooms, 5 full bathrooms, 1 half bathroom, and approximately 7,200 heated square feet (owner-provided measurement; buyer to verify). Inside, you’ll find two primary bedrooms with generous walk-in closets, an office/bedroom, a recreation room above the three-car garage, and a third-floor studio with a half bathroom. Laundry rooms on all three floors add convenience. The owner reports a 2019 roof, a new septic system, and updated appliances. Existing appliances, washers, and dryers are included. Step outside and enjoy an in-ground swimming pool, two spring-fed fishing ponds, and expansive acreage. Whether you envision a private retreat, outdoor recreation, or simply having room to spread out, this property offers space and possibilities. Enjoy the privacy of acreage living while remaining within driving distance of Brooksville-area shopping, dining, schools, and everyday conveniences. Buyers are encouraged to verify school assignments directly with the school district. TWO PURCHASE OPTIONS! Purchase the residence with 21 acres for $2,250,000, OR the seller will consider selling the residence with approximately 5 acres for $1,500,000. The 5-acre option is subject to seller approval, subdivision feasibility, survey, legal description, and applicable governmental, title, and closing requirements. The 5-acre portion is not currently a separately established parcel. A spacious residence, substantial acreage, and flexible purchase possibilities make this Brooksville property worth exploring. Private showings by appointment only.

26307 Mountain Lake Road, Brooksville

Listing courtesy of LPT REALTY, LLC. Contact: 877-366-2213

11200 Woodland Waters Boulevard, Brooksville
$899,000
6 Beds ⋅ 4 Baths ⋅ W7888704 MLS
6 BEDROOMS · 3.5 BATHROOMS · 3-CAR GARAGE · 4,409 SF · OVER 4 ACRES · SCREENED POOL · HOT TUB · NEW ROOF · WOODLAND WATERS -- ESTATE LIVING AT ITS FINEST! Have you been searching for a home that actually has room for everyone and everything? This is it. This 2002 custom Alexander-built estate sits on over 4 ACRES in Woodland Waters -- A COMMUNITY KNOWN FOR ITS ESTATE STYLE HOMES ON LARGE LOTS and a LOW ANNUAL HOA. You arrive via a LONG WINDING DRIVEWAY that sets the tone before you ever walk through the door. Step through the DOUBLE FRONT DOORS WITH LEADED GLASS into a grand ENTRANCE FOYER that opens to a FORMAL LIVING AND/OR DINING ROOM with TRAY CEILING and CROWN MOLDING. HIGH FLAT AND VAULTED CEILINGS throughout give this home a presence that is immediately felt. The GOURMET KITCHEN is the heart of the home. CENTER ISLAND WITH BAR SINK. DUAL WALL OVENS. BREAKFAST BAR. And a BREAKFAST NOOK encased in BAY WINDOWS looking out over the wooded acreage. Can you picture your morning coffee here? Because it is exactly as good as it sounds. The PRIMARY SUITE is massive. BAY WINDOW. HIS AND HERS CLOSETS. PRIVATE LANAI WITH 4 PERSON HOT TUB. A huge bathroom with DOUBLE SINKS, SOAKING TUB, and WALK-IN SHOWER. And direct access to a HUGE SECOND BEDROOM that works perfectly as a second primary suite or a private home office. Every other bedroom is genuinely spacious -- this floor plan works for real life. The THIRD CAR GARAGE IS AIR CONDITIONED -- perfect for a home gym, workshop, or private office. TWO AC UNITS. TWO WATER HEATERS. NEW ROOF TO BE INSTALLED PRIOR TO CLOSING. The big stuff is handled. Outside you have a HUGE SCREEN ENCLOSED POOL AND LANAI, a 4-PERSON HOT TUB on the screened back porch, a FENCED DOG RUN, IRRIGATION WELL,a LARGE SHED, and a completely private backyard surrounded by over 4 acres of wooded land. Total privacy. Total peace. The home is on HERNANDO COUNTY WATER with an IRRIGATION WELL for the sprinkler system. Now the location -- and this one delivers. Less than 10 minutes to the WEEKI WACHEE RIVER for kayaking, paddleboarding, and swimming with manatees. 15 minutes to PINE ISLAND for sunsets, boating, and fishing. Less than 10 minutes to the SUNCOAST PARKWAY for quick access to Tampa International Airport and everything Tampa Bay has to offer. An hour to top rated beaches. 90 minutes to Disney World, Universal Studios, and all the theme parks. Shopping, groceries, restaurants, hospitals, and schools -- all close by. Over 4 acres. 6 bedrooms. And a new roof before closing. This one checks every box and then keeps going!!

11200 Woodland Waters Boulevard, Brooksville

Listing courtesy of MERIDIAN REAL ESTATE. Contact: 352-585-6317

18308 Valor Path, Brooksville
$1,149,000
6 Beds ⋅ 5 Baths ⋅ 2260302 MLS
THIS ONE HAS IT All!!! A rare find with 2 homes + private pool nestled on 5 secluded acres in Beautiful Brooksville!! Home will get a NEW ROOF before closing!! Great property for multi-generational living!! The main home is impressive and offers 4 bedrooms + 3.5 bathrooms + 6 car detached garage + Spa! The home has gorgeous 2-story ceilings, an open floor plan, large glass windows making this home feel light, bright and spacious!! Gorgeous upgraded kitchen and bathrooms!! The second full home offers 2 bedrooms + 1 full bathroom + full kitchen + 1 car attached garage + pool access!! This rare property offers a total of 5,845 living space and 8,435 total sq footage!!! 6 bedrooms + 4.5 bathrooms + 7 car garage spaces + pool + 5 acres. The two homes are connected through a common area, but can be completely closed off, as well, for privacy! The home has lots of updates, these were done in 2020: Well Pump, wiring & pipes, Water Filtration System, 2 Tankless Water heaters, Spa Heater, fencing in front of home, Water Filtration System, Dishwasher & Refrigerator, fencing in front of home, and added a delivery access driveway for UPS/FedEx. 2021: Whole house generator, Grout redone in master shower & 3 other bath(s) & showers, New AC for downstairs, remodeled rec room/bar, added glass patio doors. 2022: New Flooring in Guest house living room, kitchen & halls, Patio screen redone, New Copper sink & faucets in kitchen. 2023: New AC for upstairs, Septic Filter replaced, New spa pump & filter, Driveway repacked & filled, Decorative boulders placed in drainage ravine. 2024: New Filter in Well System, Floor in bedroom 2 redone, Cleared 1 acre of underbrush, New vanity in the guest house bathroom. 2025: New sink faucet in bathroom 2, Complete Interior repainted, including trim, New carpet in office & guest house 2 bedrooms, New Wall Oven/Microwave Combo, New drainage stone put down around the outside perimeter (20 yards total), Removed all tree & branch debris around yard & cleared, Cut down dead or damaged trees endangering the garage & front gate area,New Spa timer & New washer. Close to everything!! Shoppes, restaurants, hospitals, schools...everything!! Close to kayaking, paddle-boarding, and swimming with the manatees in the clear Weeki Wachee River or enjoying a day at Buccaneer Bay Water Park!! Close to the sunsets at Pine Island, boating and fishing!! Less than 10 minutes to the Suncoast Parkway for quick and easy access to Tampa International Airport and for all the fun that Tampa Bay has to offer!! 1 hour + to TOP US BEACHES!! 1.5 hours to Disney World and Universal Studios and all the theme parks!!

18308 Valor Path, Brooksville

Listing courtesy of Home Land Real Estate Inc. Contact:

18308 Valor Path, Brooksville
$1,149,000
6 Beds ⋅ 5 Baths ⋅ W7887749 MLS
THIS ONE HAS IT All!!! A rare find with 2 homes + private pool nestled on 5 secluded acres in Beautiful Brooksville!! Home will get a NEW ROOF before closing!! PERFECT property for multi-generational living!! The main home is impressive and offers 4 bedrooms + 3.5 bathrooms + 6 car detached garage + Spa! The home has gorgeous 2-story ceilings, an open floor plan, large glass windows making this home feel light, bright and spacious!! Gorgeous upgraded kitchen and bathrooms!! The second full home offers 2 bedrooms + 1 full bathroom + full kitchen + 1 car attached garage + pool access!! This rare property offers a total of 5,845 living space and 8,435 total sq footage!!! 6 bedrooms + 4.5 bathrooms + 7 car garage spaces + pool + 5 acres. The two homes are connected through a common area, but can be completely closed off, as well, for privacy! The home has lots of updates, these were done in 2020: Well Pump, wiring & pipes, Water Filtration System, 2 Tankless Water heaters, Spa Heater, fencing in front of home, Water Filtration System, Dishwasher & Refrigerator, fencing in front of home, and added a delivery access driveway for UPS/FedEx. 2021: Whole house generator, Grout redone in master shower & 3 other bath(s) & showers, New AC for downstairs, remodeled rec room/bar, added glass patio doors. 2022: New Flooring in Guest house living room, kitchen & halls, Patio screen redone, New Copper sink & faucets in kitchen. 2023: New AC for upstairs, Septic Filter replaced, New spa pump & filter, Driveway repacked & filled, Decorative boulders placed in drainage ravine. 2024: New Filter in Well System, Floor in bedroom 2 redone, Cleared 1 acre of underbrush, New vanity in the guest house bathroom. 2025: New sink faucet in bathroom 2, Complete Interior repainted, including trim, New carpet in office & guest house 2 bedrooms, New Wall Oven/Microwave Combo, New drainage stone put down around the outside perimeter (20 yards total), Removed all tree & branch debris around yard & cleared, Cut down dead or damaged trees endangering the garage & front gate area,New Spa timer & New washer. Close to everything!! Shoppes, restaurants, hospitals, schools...everything!! Close to kayaking, paddle-boarding, and swimming with the manatees in the clear Weeki Wachee River or enjoying a day at Buccaneer Bay Water Park!! Close to the sunsets at Pine Island, boating and fishing!! Less than 10 minutes to the Suncoast Parkway for quick and easy access to Tampa International Airport and for all the fun that Tampa Bay has to offer!! 1 hour + to TOP US BEACHES!! 1.5 hours to Disney World and Universal Studios and all the theme parks!!

18308 Valor Path, Brooksville

Listing courtesy of HOME LAND REAL ESTATE INC. Contact: 352-556-0909

19222 Fort Dade Avenue, Brooksville
$299,400
7 Beds ⋅ 3 Baths ⋅ TB8499884 MLS
Fully renovated and income-producing, this turnkey property is an exceptional investment opportunity with strong, stable cash flow. The home features brand new flooring and subflooring, fresh interior paint, a newly installed septic system and drainfield, a 2022 roof, and a 2024 water heater with most plumbing lines updated. The bathroom has been renovated, and the HVAC system was serviced in 2025, helping minimize near-term capital expenditures. The property is currently configured for co-living with seven tenants in place, generating $4,575 in monthly rent, plus an additional $100 from two storage tenants, bringing total gross monthly income to $4,675. All tenants have been thoroughly background and credit screened and are set up on digital payment platforms, providing a streamlined and reliable rent collection process. Operational efficiency is enhanced with smart locks installed on both the front entry and individual room doors. A property cleaner/onsite contact is already in place to assist with maintenance and lawn care, making this a truly hands-off investment. SELLER FINANCING IS NOT AVAILABLE. All leases are available for review upon request for qualified buyers. This is a rare opportunity to acquire a fully stabilized asset with immediate cash flow from day one. Information is believed to be accurate but not warranted. Buyer and buyer’s agent are responsible for independently verifying all property details, including but not limited to measurements, zoning, taxes, income, leases, and condition.

19222 Fort Dade Avenue, Brooksville

Listing courtesy of LOTUS REAL ESTATE LLC. Contact: 954-393-3781

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All listings featuring the RAPB + GFLR logo are provided by the Realtors® of the Palm Beaches and Greater Fort Lauderdale, Inc. and BeachesMLS, Inc. This information is not verified for authenticity or accuracy and is not guaranteed. Copyright © 2019 Realtors® of the Palm Beaches and Greater Fort Lauderdale Inc. and BeachesMLS, Inc.

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