Brooksville Homes with Three+ Story Property Description

Welcome to Brooksville, a charming city located in Hernando County, Florida. Known for its picturesque landscapes and friendly community, Brooksville offers a peaceful retreat while still being conveniently located near major cities like Tampa and Orlando.

If you are looking for homes with unique character and plenty of space, you'll be delighted to discover properties with three or more stories in Brooksville. These homes offer not only ample living space but also stunning views of the surrounding area. Whether you're looking for a historic Victorian-style home or a modern townhouse, you'll find a variety of options to choose from in Brooksville.

Living in a three-story home in Brooksville allows you to enjoy the beauty of the city from a different perspective. Imagine sipping your morning coffee on a balcony overlooking the rolling hills or hosting a dinner party in a spacious living room with high ceilings. With a three-story home, the possibilities are endless.

Whether you're looking to relocate to Brooksville or already call this city home, owning a three-story property is a unique opportunity to experience luxury living in a serene setting. Don't miss out on the chance to find your dream home in Brooksville, where small-town charm meets modern convenience.

Newest Brooksville Homes with Three+ Story Property Description

$485,000

5 Beds ⋅ 3 Baths ⋅ Woodland Valley SubDv. ⋅ 34602 Zip Code

High upon the hill, Crafted and cared for through the years with amazing stewardship sits a home perfectly ready for only its second owner. If you're looking for a home with storage, capabilities to easily work from home, live with in-laws, or disaster readiness this is your home. With a full dry basement for riding out Florida storms or prepping for the future and a full attic for storage, five bedrooms, and a studio with it's own separate entrance this home is more than capable of improving your daily living. The beautiful bright and custom kitchen is just one of the many thoughtful updates. Tired of the cookie cutter builder specs? This home is the antidote. Plenty of storage space, plenty of room for the whole family with none of the useless space to waste time maintaining. Mature landscaping lovingly grown includes; persimmons, peaches, lemons, an olive tree and so much more. Come see all the reasons this house is perfect for you.

29249 Wilpayne Road, Brooksville

$1,425,000

5 Beds ⋅ 5 Baths ⋅ Royal Oaks Estate SubDv. ⋅ 34601 Zip Code

NEW LOWERED PRICE-SELLER MOTIVATED-Live in luxury on 2.5 private acres bordering a 100+ acre protected deer preserve. This one-of-a-kind 12,400+ sq ft custom estate offers resort-style living with complete privacy and impressive amenities. Completely rebuilt in 1995, the main home features 5 bedrooms and 4.5 bathrooms, while the detached guest house above the two-car garage includes 1 bedroom, 1 bath, a full kitchen, and a private viewing deck — perfect for multi-generational living or rental income. As you arrive, the gated driveway reveals a grand entrance with an imported Venetian chandelier and dramatic spiral staircase, setting the tone for this exceptional home. The spacious layout includes a formal living room with intricate molding, a formal dining room featuring a stunning Venetian crystal chandelier, a large primary suite overlooking the pool, and flexible spaces ideal for a family room, game room, theater, or office. Upstairs you’ll find an additional bedroom, a large den with separate exterior entrance, and a dramatic loft with elegant backlit mirrors from Oklahoma’s Governor’s Mansion. The heart of the home is the oversized heated indoor pool with skylights and opening sliding glass doors, seamlessly connected to an air-conditioned professional racquetball court (perfect for pickleball, batting practice, or more). Outside, enjoy the oversized screened lanai with gas fire pit, wrap-around porch, pavered seating areas, and lush backyard. Additional highlights include a secure fenced dog area and beautiful views of the preserve. A 2025-updated kitchen with all-new appliances, combined with expansive living areas, makes this 3-story estate ideal for large-scale entertaining or relaxing in total privacy. Recent major updates include a NEW ROOF (2022), 4 newer AC units, and luxury vinyl plank flooring in select areas. Located in the exclusive Royal Oaks Estates with NO HOA, this home is just 35 minutes from Tampa and 10 minutes to hospitals, shopping, and restaurants. This magnificent custom property is truly one-of-a-kind. Contact us today to schedule your private tour. SELLER WOULD CONSIDER A LEASE OR A LEASE TO OWN OPTION.

21033 Violet Road, Brooksville

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