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5-Bedroom Homes for Sale in Brooksville, FL with Private Pool

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  • /57

    $989,900

    • 5 Beds
    • 4 Baths
    • 4,364 Sq Ft

    11159 Cindy Dr, Brooksville, FL 34601

    Step into timeless elegance with this custom-built British Colonial masterpiece, offering over 4,300 sq. ft. of air-conditioned living space plus an enclosed sunroom, spacious patio, and an oversized 2-car garage with additional storage. Set on 2.5 beautifully landscaped acres filled with fruit trees and flowering plants, this home offers space, privacy, and charm in equal measure. Built in 1983

    Agent Photo

    Tiffany Flanders

    SOUTHERN BELLE REALTY, INC

    (352) 520-3886

    11159 Cindy Dr, Brooksville, FL 34601
  • /60

    $499,000

    • 5 Beds
    • 2 Baths
    • 2,441 Sq Ft

    15059 Woodbury Rd, Brooksville, FL 34604

    Spacious 5-Bedroom Pool Home in Springwood EstatesThis 5-bedroom, 2-bath home sits on a large 0.6-acre lot in the popular Springwood Estates neighborhood. It has tile floors throughout, a split floor plan for privacy, and a new roof installed in 2021.The primary bedroom has sliding doors to the pool and a big bathroom with two sinks, a sunken tub, a walk-in shower, and a walk-in

    Agent Photo

    Tiffany Flanders

    SOUTHERN BELLE REALTY, INC

    (352) 703-1646

    15059 Woodbury Rd, Brooksville, FL 34604
  • /114

    $1,324,900

    • 6 Beds
    • 4.5 Baths
    • 5,845 Sq Ft

    18308 Valor Path, Brooksville, FL 34604

    Rarely does a a home this unique come to market, and this home is truly special! Natures' private hideaway, nestled in the trees and off the beaten path. 5 acres of unspoiled beauty, your incredible 6 bedroom, 4.5 bath sanctuary awaits. Stately two-story Estate Home offers open spaces, lots of natural light, high ceilings, dormers, screened porches, a free-form dip pool and spa, a huge primary

    David Longspaugh RE/MAX Sunset Realty

    18308 Valor Path, Brooksville, FL 34604
  • /45

    $999,900

    • 5 Beds
    • 5 Baths
    • 3,226 Sq Ft

    22770 Skyview Cir, Brooksville, FL 34602

    CLASSIC VICTORIAN STYLE 5 BEDROOM, 3 FULL BATHROOM + 2 HALF BATH HOME ON PRIVATE 6.3 WOODED ACRES!This spacious 3,226 sq ft home blends timeless charm with modern amenities. The heart of the home is a large island kitchen with Corian countertops and eat-in dining, which opens to a cozy family room with fireplace — perfect for entertaining or relaxing evenings.The second-floor

    Alan Hengesbach Realty Executives America

    22770 Skyview Cir, Brooksville, FL 34602
  • /67

    $1,200,000

    • 5 Beds
    • 5 Baths
    • 3,900 Sq Ft

    1353 Spring Lake Hwy, Brooksville, FL 34602

    Rustic Luxury on 16.6 Acres – Private Homestead Retreat in Spring Lake, Brooksville.Nestled in the scenic hills of Spring Lake, this exceptional Brooksville estate blends timeless rustic charm with modern comfort. Featuring a spring-fed creek, a half-acre stocked pond, and sprawling, lush pastures, this private homestead offers the serenity and seclusion ideal for those craving a

    Frank Ely Herron Real Estate LLC

    1353 Spring Lake Hwy, Brooksville, FL 34602
  • /49

    $1,100,000

    • 5 Beds
    • 3 Baths
    • 3,116 Sq Ft

    18104 Ayers Rd, Brooksville, FL 34604

    Motivated seller! Welcome to Belleau Wood Manor! Enjoy the winding and picturesque private drive as it leads you to the entrance of this modern Victorian beauty. Feel free to stop at the separate cabin on your way up! Boasting five bedrooms and over 3,100 sqft of living space, the primary residence offers three levels of quiet and private country living. Hardwood floors, granite

    Emil Varrichio III Dennis Realty & Investment Corp

    18104 Ayers Rd, Brooksville, FL 34604
  • /69

    $880,000

    • 5 Beds
    • 4.5 Baths
    • 3,513 Sq Ft

    19256 Hidden Oaks Dr, Brooksville, FL 34604

    PRICE REDUCTION- SELLERS ARE MOTIVATED and ready to make a deal! Tucked away in the beautiful neighborhood of Hidden Oaks sits this beautiful country estate featuring a 3/2 main house and 2/2.5 guest cottage on 8.3 acres. The home offers an open floorpan with the kitchen overlooking the dining and living room areas with a central office and full laundry room equipped with a tankless water heater.

    Krista Plagge TROPIC SHORES REALTY LLC

    19256 Hidden Oaks Dr, Brooksville, FL 34604
  • /75

    $1,250,000

    • 5 Beds
    • 4.5 Baths
    • 4,555 Sq Ft

    6375 Emanuels Way, Brooksville, FL 34602

    Recent luxury enhancements include newly installed engineered hardwood flooring throughout the upper level and fresh interior paint in elegant, neutral tones —offering a sophisticated and move-in ready aesthetic. Step into a world where charming country living meets stately European elegance in this custom-built masterpiece. This extraordinary residence, perched on 8.4 acres with the option to

    Marisa Brewer Preferred Property Associates,

    6375 Emanuels Way, Brooksville, FL 34602
  • /66

    $825,000

    • 9 Beds
    • 4.5 Baths
    • 5,104 Sq Ft

    4063 Baseball Pond Rd, Brooksville, FL 34602

    Endless opportunities at this incredible property on 10.3 ACRES! Zoned AG + additionally zoned for an Assisted Living Facility, this property features a 9 bedroom 4.5 bathroom home with a POOL, a detached guest house, 8 fully fenced pastures, and multiple barns. Bring your animals! The main home with stunning stone accents and Hardie Board siding boasts over 5,100 of heated square feet! Upstairs

    Jessie Morris JT REALTY & ASSOCIATES

    4063 Baseball Pond Rd, Brooksville, FL 34602
  • /67

    $599,900

    • 5 Beds
    • 3 Baths
    • 3,107 Sq Ft

    15287 Coot Rd, Brooksville, FL 34614

    Check out this Incredible 5 Bedroom, 3 Bathroom 3+ Car Garage with over 4,500 Square Feet under roof is Ready for You & Your Family with a Separate In-Law Suite with Private Entrance!! This Luxurious Open Concept Home with Split Plan 3/2 Home has an Attached but Separate In-Law Suite with 2 Bedrooms, 1 Handicap Accessible Bathroom and includes Full Kitchen, Additional Laundry Room, Family Room &

    Elizabeth Casner TROPIC SHORES REALTY LLC

    15287 Coot Rd, Brooksville, FL 34614
  • /68

    $330,000

    • 6 Beds
    • 2 Baths
    • 2,280 Sq Ft

    4435 Orlando Ave, Brooksville, FL 34604

    Welcome to 4435 Orlando Avenue, where opportunity and flexibility meet comfort and charm. Tucked away on nearly half an acre in Brooksville, this unique 6-bedroom, 2-bathroom manufactured home sits on two fully fenced parcels with multiple gated entries—perfect for privacy, pets, or a variety of uses. From the moment you arrive, you'll appreciate the mature landscaping, a welcoming front porch

    Elizabeth Dougherty Keller Williams-Elite Partners

    4435 Orlando Ave, Brooksville, FL 34604
  • /55

    $825,000

    • 5 Beds
    • 3.5 Baths
    • 3,554 Sq Ft

    10110 Weeks Dr, Brooksville, FL 34601

    HUGE POOL HOME IN HERNANDO COUNTRY CLUB WITH NEW ROOF!! WELCOME TO YOUR DREAM HOME!! An impressive 5 bedroom, 3.5 bath residence with an OVERSIZED 3.5 CAR GARAGE & VERY SPACIOUS (44X12) ATTIC, nestled in one of the area's most sought-after neighborhoods. From the moment you step into the grand foyer, you'll be captivated by the soaring 10ft ceilings, 8ft doorways, large windows, true dormers, and

    Jami Frazier, PA SOUTHERN COAST TO COUNTRY RLTY

    10110 Weeks Dr, Brooksville, FL 34601
  • /85

    $822,777

    • 5 Beds
    • 3 Baths
    • 3,300 Sq Ft

    7376 Fall St, Brooksville, FL 34613

    INCREDIBLE...THIS ONE HAS IT ALL!! ALMOST NEW 2024 Dream Custom Home with amazing outdoor living space - built by the builder as his custom home with all the upgrades!! 5 bedrooms (or 4 with office) + 3 full bathrooms + 4 car garage with 9,000 lb lift and 8' tall garage doors (18' and 14' wide) for your larger vehicles + private pool with sun shelf and safety fence + completely fenced + nestled

    Kimberly Pye HOME LAND REAL ESTATE INC

    7376 Fall St, Brooksville, FL 34613

Home Trends in Brooksville, FL

Housing Trends

Median Sale Price
$349,990
Median Single Family Sale Price
$345,000
Median 2 Bedroom Sale Price
$205,333
Average Price Per Sq Ft
$213
Number of Homes for Sale
74
Last 12 months Home Sales
841
Months of Supply
1.10
Median List Price
$372,990
Median Change From 1st List Price
3%
Median Home Sale Price YoY Change
7%
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