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Brooksville, FL with a Pool for Sale Map Search

Homes for Sale with a Pool in Brooksville, FL

Welcome to your dedicated resource for homes for sale with a pool 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 with a pool properties currently available below, or contact a local agent to discuss the details that matters most to your search.

All Homes for Sale with a Pool in Brooksville, FL

$1,199,000
5 Beds 4 Baths Southern Hills Plantation Ph 1 SubDv.
Welcome to one of the most iconic homes in Southern Hills Plantation, a stunning custom-built luxury estate positioned along the Pete Dye Championship Golf Course with sweeping pond and fairway views in the front and a private preserve behind. This extraordinary residence has become one of the signature homes within the community and offers an unmatched combination of architectural presence, craftsmanship, and resort-style living. This expansive two-story home features 5 bedrooms, 4 full bathrooms, formal living and dining rooms, a large family room, dedicated office space, additional flex/yoga room, private elevator, and an incredible 7-car garage configuration that is nearly impossible to find in Southern Hills. The welcoming wraparound front porch creates unforgettable curb appeal and sets the tone for the elegance found throughout the home. Inside, custom finishes immediately stand out including beautiful wood flooring, extensive millwork, plantation shutters, soaring ceilings, elegant wainscoting, designer lighting, and spacious open living areas filled with natural light. French doors throughout create a seamless connection between indoor and outdoor living. The chef’s kitchen was designed for entertaining and daily living alike, featuring marble and granite countertops, double ovens, custom cabinetry, oversized prep areas, dedicated coffee station, walk-in pantry with water line for an additional ice maker, spacious mud room, and oversized laundry area. Adding warmth and character throughout the home are three fireplaces, including two gas fireplaces—one being a dramatic double-sided centerpiece—as well as an additional wood-burning fireplace. One of the home’s standout features is the private elevator, offering convenience, luxury, and long-term practicality. Upstairs, the primary suite feels like a private retreat complete with spa-inspired bath areas, an extraordinary “Queen’s Closet” with sink and makeup station, and a separate oversized men’s walk-in closet. Every bedroom features its own walk-in closet. The home is fully wired as a smart home with every room hardwired for internet connectivity. Additional smart features include app-controlled above-cabinet lighting, backyard safety lighting, adjustable landscape lighting timers, and hot/cold water hookups on both the lanai and near the maintenance garage door. The outdoor living experience rivals a private resort with an expansive screened pool area featuring multiple entertaining spaces, grilling areas, sunshelf, and a dramatic 10-foot-deep pool. The fully fenced backyard opens to a peaceful preserve setting with no rear neighbors. Car enthusiasts and entertainers will appreciate the massive 7-car garage offering endless possibilities for a workshop, golf simulator, theater space, gym, game room, or showcase collection. Additional highlights include approximately 6,000 square feet of professionally cleaned, re-sanded, and sealed pavers completed in December 2025 and a brand-new roof installed in February 2026. Located within the gated Southern Hills Plantation Club, residents enjoy access to the Pete Dye Championship Golf Course, elegant clubhouse, resort-style pool, poolside dining, tennis and pickleball courts, fitness center, spa services, walking trails, and a true country club lifestyle approximately 50 minutes from Tampa International Airport.

5251 Summit View Drive, Brooksville

$460,000
4 Beds 3 Baths Dogwood Estate Ph I SubDv.
Virtually Staged. BACK ON MARKET, PROPERTY APPRAISED- 10002 Domingo Dr, Brooksville, FL 34601 - Welcome to this beautifully maintained two-story home nestled on just over a half-acre in the highly sought-after community of Dogwood Estates. Featuring 4 bedrooms, 3 full baths.  Offering timeless charm and distinctive character, this residence blends the warmth and elegance of an old Victorian-style home with tasteful modern updates and meticulous care throughout. Boasting 2,173 living square feet plus an additional 336-square-foot enclosed sunroom, this spacious home is designed for both comfortable everyday living and entertaining. From the moment you enter, you are greeted by a large formal living room or study that sets the tone for the home's inviting character and charm. The updated kitchen offers an abundance of counter space, ideal for gatherings and entertaining, while the adjoining sitting area creates the perfect setting for formal dining overlooking the pool area. Beyond the foyer, the expansive family room showcases beautiful views of the pool and outdoor living space. Plantation shutters throughout the home add timeless elegance, while the combination of tile and wood flooring enhances the warm and inviting atmosphere. Crown molding throughout further elevates the interior with refined architectural detail. The first-floor primary suite offers comfort and privacy, featuring a beautifully updated bath complete with a jetted soaking tub, separate shower, and spacious layout designed for relaxation. An additional first-floor guest bedroom and full bath provide excellent flexibility for guests or multigenerational living. Upstairs, two private guest bedrooms share a full bath and each feature access to their own outdoor terrace, creating peaceful retreats with added privacy for family or visitors. The enclosed sunroom features tile flooring and walls of windows overlooking the pool area, offering a bright and relaxing extension of the living space year-round. Step outside and enjoy the beautifully landscaped park-like setting complete with a charming gazebo, spacious pavered pool area, and additional storage shed. The outdoor living space creates the perfect private retreat for relaxing, entertaining, or enjoying Florida living at its finest. Outside, the oversized side-load two-car garage and expansive circular driveway provide ample parking and impressive curb appeal. This home has been meticulously maintained with major updates including a roof replaced in 2011, AC in 2012, and several windows updated in 2021. If you are searching for a home filled with character, warmth, privacy, and timeless appeal in an established community, this exceptional Dogwood Estates property is truly one-of-a-kind.

10002 Domingo Drive, Brooksville

$334,900
4 Beds 3 Baths Benton Hills SubDv.
Pre-Construction. To be built. Two stories of modern brilliance await in the Sycamore, situated on a spacious lot, fully landscaped lot that provides exceptional privacy and curb appeal. Step onto the covered front porch and enter an open foyer that introduces a versatile flex space, perfect for a home office, study, or exercise area. The main floor features ceramic tile flooring throughout an open-concept living area. This layout seamlessly connects the kitchen, dining nook, and an open great room with added windows for abundant natural light. The stunning kitchen features quartz countertops, stainless steel appliances including an eStar side-by-side refrigerator, and a large center island with seating and prep space. From the eating nook, sliding glass doors lead out to a screened-in hip porch, expanding your living space into the outdoors. Upstairs, the second floor features comfortable carpeting throughout the bedrooms. The primary suite spans the entire rear of the property, providing ceramic tile shower, dual vanities with quartz countertops, and two walk-in closets for a wardrobe fit for royalty. Three additional bedrooms complete this level, each generously sized, with one including its own walk-in closet. The fourth bedroom sits at the opposite corner near the secondary full bathroom to provide extra privacy. For ultimate convenience, the second-floor laundry room is centrally located and easily accessible from all sleeping areas. Modern upgrades include a two-car garage with direct home access, irrigation on front and side, architectural roof shingles, and a built-in Smart Home Package featuring a Ring® Video Doorbell, Smart Thermostat, Keyless Entry Smart Door Lock, and Deako® Switches. A full builder warranty provides total peace of mind. This property is part of Benton Hills, a new community located just 4.6 miles from Sherman Hills Golf Club. Designed for connection, recreation, and everyday comfort, the neighborhood provides amenities that make it easy to enjoy the Florida lifestyle. Residents can enjoy a clubhouse, resort-style pool, walking trails, dog park, and playgrounds, all thoughtfully designed to bring neighbors together. Don't wait, schedule a tour today and experience everything that makes the Sycamore exceptional!

31576 Wild Grape Lane, Brooksville

$795,000
3 Beds 2 Baths Evans Lakeside Heights SubDv.
Private 3.6-Acre Pool Retreat in Weeki Wachee with No HOA, 2023 Dimensional Roof, Electric Gated Entry, Fenced & Cross-Fenced Grounds, Oversized 3-Car Garage, 4-Car Carport, RV Parking with 50-Amp Service, and an Incredible Outdoor Entertaining Setup. Although located west of US-19, this property sits High and Dry, helping clear up the common misconception that every west-side property is low or flood-prone. This is not a cookie-cutter home. It is a rare Space-and-Lifestyle Property for the buyer who wants Privacy, Parking, Storage, Pool Living, and Room to Breathe while still being close to Shopping, Restaurants, Medical, the Suncoast Parkway + the Nature Coast Lifestyle. Set on 3.6 Acres, this Inviting Property offers Space, Privacy, & Versatility that is hard to find. The Electric Gate welcomes you in while the Fenced & Cross-Fenced Grounds create Function + Charm. The Park-Like Backyard feels like your own Private Retreat w/ a Swing, Tiki Bar, Frequent Deer Sightings, & a 12x20 Shed. This property is well-equipped for extra Parking, Storage + Flexibility. In addition to the Oversized 960 sq. ft. 3-Car Garage, there is a 240 sq. ft. attached Storage Area w/ Barn Door access, a 4-Car Carport, & RV Parking w/ 50-amp service along the side of the Garage. Garage Screens add even more flexibility & the Breezeway connection to the home enhances Convenience & Character. The newly seal-coated Driveway adds to the overall Appeal. Outdoor Living is where this home truly shines. The Backyard Retreat features a Swimming POOL w/ Vaulted Screen Enclosure, Newly Screened Extended Lanai with paint-chip epoxy finish, Covered Dining Area, & Covered Hot Tub w/ Waterfall & Lighting Features. Whether hosting Gatherings or enjoying a Quiet Evening at home, this Outdoor Space offers the perfect backdrop for Relaxing and Entertaining. Inside, the Open Floor Plan is Warm, Welcoming & full of Character. The Living Room features a Vaulted Ceiling w/ exposed Wood Beam, Stone Wood-Burning Fireplace, & Bay Window for Beautiful Natural Light. The Kitchen is thoughtfully designed w/ Custom Cherry Wood Cabinetry, Granite Countertops, Island / Breakfast Bar, Pull-Outs, Pot Drawers, Built-In Pantry, Appliance Garage, Lazy Susan, Cookie Sheet Storage, Spice Rack, Reverse Osmosis, Full-House Water Filtration System, & Wood Ceiling with Skylight. All Stainless Steel Bosch Kitchen Appliances stay with the home. The Dining Room has a Bay Window, Modern Farmhouse Lighting, & Pocket Sliding Glass Doors that open to the Lanai for easy Indoor-Outdoor Living. The Family Room, currently used as a Game Room & including a Pool Table, offers its own Entrance and Closet Space, making it an ideal Flex Room that could serve as a 4th BEDROOM. The Primary Owner's Suite has Plank-Looking Tile Flooring, a Vaulted Wood-Beam Ceiling + Wayfair Barn Doors leading to the Walk-In Closet & En-Suite Bathroom. The Remodeled Primary Bathroom features a No-Step Tiled Walk-In Shower w/ Glass Waterfall Detail & Glass Door, Taller Vanity w/ Dual Square Sinks, Quartz Countertops, & a Beautiful Mirror that coordinates with the Guest Bathroom. On the opposite side of the home are 2 Additional Bedrooms w/ Generous Closet Space + a Guest Bathroom w/ Tub/Shower Combination. The Laundry Room includes a Folding Table & Brand-New 2026 Stackable Washer/Dryer. If you are looking for more than a standard subdivision home, this property delivers Privacy, Beauty & a True Feeling of Home.

9032 Birmingham Avenue, Brooksville

$650,000
3 Beds 3 Baths Woodland Waters Ph 5 SubDv.
Welcome to the prestigious Woodland Waters community! Discover this truly unique courtyard home — an entertainer’s dream — perfectly designed for comfort, style, and endless gatherings. Nestled near US-19 and just moments from local attractions like Weeki Wachee Springs, this home offers both tranquility and convenience. Enjoy easy access to grocery stores, shops, and restaurants, all within a short drive. Step inside to an inviting open-air design where living spaces flow seamlessly around the courtyard. Abundant natural light streams through sliders throughout the home, creating a bright and welcoming atmosphere. Each bedroom includes its own private bathroom, offering comfort and privacy for family and guests. The one-bedroom in-law suite provides independent living while staying close to the main home. Outdoors, relax or entertain in the private screened and covered lanai or the spacious outdoor patio overlooking the the secluded property with over an acre of land. Car enthusiasts will love the oversized three-car garage with a split A/C system and built-in theater room — perfect as a garage or flexible bonus space — plus an additional detached four-car garage for extra vehicles, toys, or workshop space. The large driveway provides plenty of parking for guests. This remarkable property combines luxury, functionality, and space in one of the area’s most desirable communities.

10120 Shortleaf Court, Brooksville

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