Explore Brooksville, FL Homes for Sale Between $500,000 to $550,000

Brooksville, FL Homes for Sale Between $500,000 to $550,000 Map Search

Homes for Sale in Brooksville, FL Between $500,000 to $550,000

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Welcome to your dedicated resource for Homes for Sale Between $500,000 to $550,000 in Brooksville, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Brooksville, FL agents, Joseph Sullivan Real Estate specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the properties currently available between $500,000 to $550,000 below, or contact a local agent to discuss the details that matters most to your search.

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All Brooksville, FL Homes for Sale Between $500,000 to $550,000

$539,900
Potterfield Garden Ac SubDv.
3.25 acres of C1 COMMERCIAL LAND with access to 3 roads!! 300+ feet of frontage on Weeping Willow, 160 ft of frontage on Jacqueline Road that runs behind the movie theater, and 300 ft of frontage on Chelsey Rd. The property used to have a home, well(s), and septic(s) on it. The home has been cleared off. Growing area!! Check out all the new commercial construction going up on Jacqueline and in the area of Cortez and Weeping Willow. 42,500 Average Annual Daily Traffic at the corner of Weeping Willow and Cortez Blvd just 450 feet away!! Call for more details.

Weeping Willow Road, Brooksville
$519,900
3 Beds ⋅ 3 Baths ⋅ Southern Hills Plantation Ph 1 SubDv.
A home like this offers one of the best combinations of value and outdoor space in Southern Hills Plantation. With over 0.7 acres across two combined lots, a brand-new roof, and an expansive fenced backyard, you'll enjoy the feel of a much larger estate while remaining in an attainable luxury price point. From the moment you step inside, soaring ceilings, rich crown molding, and classic plantation shutters create a warm, inviting atmosphere. Multiple living spaces--including a formal dining room, elegant sitting room, and spacious family room--provide the flexibility today's buyers are looking for, whether you're entertaining guests or simply enjoying a quiet evening at home. At the heart of the home is a chef-inspired kitchen featuring granite countertops, a gas range, abundant cabinetry, and a sunny breakfast nook overlooking the backyard. One of this home's most unique features is its incredibly versatile floor plan. A dedicated office positioned between two guest bedrooms creates the perfect space for a private guest suite, multi-generational living, children's retreat, or work-from-home setup without sacrificing privacy. Step outside and you'll quickly understand what makes this property so special. The screened lanai opens to an expansive wrought-iron fenced backyard with mature landscaping, flowering gardens, and multiple seating areas. Whether you envision adding a custom pool, hosting family gatherings, letting pets roam freely, or simply enjoying peaceful evenings outdoors, this oversized homesite offers opportunities that few properties in Southern Hills can match. The spacious primary suite provides a relaxing retreat with generous proportions, a large walk-in closet, and plenty of room to unwind after a day on the course or at the clubhouse. Property Features: • Over 0.7 acres across two combined lots • Brand-new roof • Guard-gated Southern Hills Plantation • Wrought-iron fenced backyard • Screened lanai with brick pavers • Gas range • Plantation shutters throughout • Flexible office/in-law suite potential • Beautiful landscaping with exceptional outdoor living space Living in Southern Hills Plantation means enjoying a lifestyle unlike any other, complete with a championship Pete Dye golf course, resort-style pool, fitness center, spa, tennis and pickleball courts, multiple dining venues, walking trails, and a vibrant year-round social calendar. If you've been searching for a luxury home with a truly exceptional yard in Southern Hills Plantation, this is an opportunity you won't want to miss.

19531 Mossy Oak Court, Brooksville
$525,000
4 Beds ⋅ 2 Baths ⋅ Royal Highlands SubDv.
Virtually Staged. Short Sale. Short sale. Set on a fully usable, fenced 1-acre homesite with no HOA, this 4-bedroom, 2-bath residence offers approximately 2,500 square feet of well-designed living space and a true indoor-outdoor Florida lifestyle. Built in 2006 with architectural upgrades not often found in this market, the home features double entry doors with etched glass, tray ceilings, rounded wall accents, and multiple living and entertaining spaces designed for comfort and flow. The open kitchen and family room overlook the screened lanai and saltwater pool, with multiple sliding glass doors providing direct access from nearly every main living area—including the primary suite, formal living room, kitchen nook, and secondary bedroom—creating seamless indoor-outdoor living. The screened lanai and pavered pool area serve as the centerpiece of the home, complete with a built-in outdoor grill and ceramic egg-style cooker, ideal for entertaining or relaxing year-round. The primary suite is privately situated and features lanai access, two walk-in closets, and a spacious bath with dual vanities, walk-in shower, and enclosed toilet room. Three additional bedrooms are located on the opposite side of the home for added privacy. Additional features include a gas fireplace, whole-house central vacuum system, indoor laundry room with utility sink, and an attached three-car garage with storage or workshop potential. Roof replaced in 2022. Septic system. Located in Hernando County near Weeki Wachee Springs, Gulf Coast recreation, shopping, and major roadways.

8476 Madrid Road, Brooksville
$550,000
7 Beds ⋅ 5 Baths ⋅ N/A SubDv.
Virtually Staged. Rare Income-Producing Opportunity: Fully renovated 5-acre multi-family compound in Brooksville, Hernando County, featuring three separate residences plus detached garage/workshop on agriculturally zoned, fully fenced land with NO HOA and NO CDD fees. This turnkey investment property offers immediate rental income potential, multi-generational living flexibility, or agricultural business operations with multiple revenue streams. Zoning: Agricultural (AG)—buyer to verify —allows residential use, livestock, farming, nursery operations, equestrian activities, RV/equipment storage, and home-based businesses, subject to county permits. Property includes 4 structures with individual utilities: (1) Block-constructed 1-bedroom/1-bathroom home (approx. 580sqft) with bonus flex room, completely rewired electrical system(2025), updated kitchen and bathroom, new roof October 2025, central AC, individual electric meter, separate septic system, own postal address, and exterior water/electrical hookups; (2) Renovated 3-bedroom/2-bathroom double-wide mobile home (1973) with complete interior updates, modern kitchen and bathrooms, luxury vinyl flooring, central AC, individual electric meter, separate septic, own postal address, aluminum roof (1999), washer and dryer, and exterior utilities; (3) Second renovated 3-bedroom/2-bathroom double-wide mobile home (1972) with complete electrical system replacement (2025), full interior updates, kitchen, bathrooms, contemporary ceramic tile flooring, central AC, individual electric meter, separate septic system, own postal address, Aluminum Roof (1999), washer and dryer and exterior water/electrical access; (4) Block-constructed detached garage with finished interior, utility sink, electricity, water hookup, new roof October 2025, suitable for studio, workshop, or additional storage/rental income. Each residence has its own postal address, enabling separate rental agreements. The completely fenced 5-acre parcel includes substantial cleared usable land ideal for small livestock, gardens, workshops, equipment parking, RV/boat storage, or future agricultural expansion. Infrastructure highlights: Private well system serving all structures, separate septic tanks, individual electric meters for each living unit allowing tenant-paid utilities, exterior hose bibs and 110V electrical outlets on all structures, central AC systems in all three homes, and ample parking throughout. The fully fenced acreage offers cleared land perfect for vegetable gardens, farming, chicken coops, goat/sheep enclosures, horse paddocks, greenhouse operations, or nursery business—all subject to Hernando County zoning regulations and permits. Income potential: Three rentable residences with separate addresses and utilities create immediate cash flow, while garage/workshop adds rental or business value. Prime Brooksville location with convenient access to US-19, Cortez Boulevard (SR-50), Weeki Wachee Springs State Park, Brooksville downtown, shopping (Walmart, Publix), dining, Oak Hill Hospital, and essential services—perfect balance of rural privacy with urban convenience. This turnkey agricultural compound with NO HOA/NO CDD provides unlimited flexibility for investors, multi-generational families, agricultural entrepreneurs, or income property seekers in Florida's Nature Coast. Showings strongly recommended to appreciate the extensive renovations, income-producing layout, and versatility this rare 5-acre property offers.

15217 Bailey Hill Road, Brooksville
$550,000
Rare 5.1-acre fenced parcel with Public Utilities and Electricity available, located directly on Cortez Blvd (SR-50) in Brooksville and Not in a Flood Zone. Zoned AG, this property allows a Single-family, Mobile, Modular, or Manufactured home, plus accessory structures such as barns, workshops, garages, and equipment storage buildings (per county setbacks). Horses, livestock, crops, and agricultural use are permitted, making it ideal for a private residence, a Hobby Farm, an Equestrian property, or an Income-producing Agricultural venture. No HOA or CDD, giving you full control of the land for your plans and long-term goals. Prime location with excellent exposure on a major corridor near I-75, US-301, and the Suncoast Parkway, offering strong potential for future appreciation or development. Centrally located just 45 minutes to Tampa, 1 hour to Orlando, and 1 hour to Ocala. Financing available with as little as 20% down for qualified buyers.

27360 Cortez Boulevard, Brooksville
$525,000
An incredibly rare opportunity awaits with this 40-acre tract tucked deep within the heart of the 40,000±-acre Chassahowitzka Wildlife Management Area. Completely surrounded by state owned preserve land, this property offers unmatched seclusion and direct access to some of Florida’s most pristine wilderness. A true outdoorsman’s retreat, the land is abundant with game and provides exceptional hunting and outdoor recreation in every direction. Its setting and proximity to the Tampa Bay region, makes it ideal for a private hunt camp, a weekend escape, or simply a place to immerse yourself in the natural beauty of old Florida. This is a one-of-a-kind property featuring a private, off grid setting, while just an hour from Tampa, allowing easy access for day trips or weekend getaways.

Pine Island Drive, Brooksville
$543,000
4 Beds ⋅ 2 Baths ⋅ Royal Highlands SubDv.
One or more photo(s) has been virtually staged. BRAND NEW QUARTZ COUNTERTOPS + UP TO $10,000 IN SELLER CONCESSIONS WITH A REASONABLE OFFER! 4 BEDROOM | 2 BATH | 2,200+ SF | SALTWATER POOL | NEARLY 1/2 ACRE Built in 2020 and set on just under half an acre in Royal Highlands, this 4 bedroom, 2 bathroom pool home offers over 2,200 square feet of living space with high ceilings, a split bedroom layout, and tile flooring throughout the main living areas. The kitchen has been updated with brand new quartz countertops and features a large center island, walk in pantry, plenty of storage, and a stove with a built in air fryer. The breakfast nook overlooks the saltwater pool, creating the perfect spot to start your day. The primary suite features a double vanity and oversized shower, while the 20x12 enclosed porch adds additional living space with pool views and direct bathroom access. Step outside to your own backyard retreat. The screen enclosed saltwater pool is surrounded by travertine pavers and comes alive at night with color changing lights. The fully fenced yard includes two storage sheds, fruit trees, and beautifully maintained landscaping. No HOA. No CDD. Two car garage. Move in ready and built for enjoying the Florida lifestyle year round.

13079 Harris Hawk Road, Brooksville
$525,000
Princeton Place SubDv.
Cleared and level commercial lot. On Yale and Cortez Blvd. 1.3 miles to US 19. Great Location! Need more space? Additional lots available on Yale Ave.

10260 Yale Avenue, Brooksville
$525,000
Princeton Place SubDv.
Just over half an acre, cleared and shovel ready. Frontage on Cortez Blvd and Yale Ave.

10270 Yale Avenue, Brooksville
$525,000
Princeton Place SubDv.
Corner lot .80 Acres. Cleared and level lot. 1.3 miles to US 19, one block to Cortez Blvd. Lot 1.

10201 Yale Avenue, Brooksville
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