Browse All Holiday FL Between $500K - $600K Properties for Sale

5 Beds ⋅ 6 Baths ⋅ Forest Hills Un #22 SubDv. ⋅ 34690 Zip Code

PRICED TO SELL * HERE'S ANOTHER OPPORTUNITY TO PURCHASE THIS UNIQUE AND MAGNIFICENT WATERFRONT HOME, SURROUNDED ON THREE SIDES BY SPECTACULAR WATER VIEWS * THIS HOME WITH SPANISH AND MEDITTERANEAN ARCHITECTURE, FEATURES SUCH AS BEAMED CEILINGS AND ARCHED OPENINGS THROUGHOUT IS VERY SPACIOUS AND HAS AN ATTRACTIVE LAYOUT ON TWO FLOORS * TWO MASTER BEDROOMS, EACH ACCESSED BY TWO SEPARATE STAIRWAYS OPEN UP TO DECKS WITH UNOBSTRUCTED WATER VIEWS * BEAUTIFUL MARBLED DESIGN CERAMIC TILE THROUGHOUT HOME * THE GROUND FLOOR IS ACCESSED BY A WELCOMING FOYER WITH STEP DOWN TO A LARGE LIVING ROOM ON ONE SIDE AND OFFICE/TV ROOM ON THE OTHER * HALLWAY LEADS TO A LARGE LIBRARY, A HALF BATH AND A STAIRWAY TO THE SECOND FLOOR * FOUR BEDROOMS AND 3 FULL BATHS GREET YOU WITH SERENE AND PEACEFUL VIEWS OF THE ANCLOTE RIVER * UPGRADES BY THE PRESENT OWNERS INCLUDE THREE AC SYSTEMS REPLACED WITHIN THE LAST 4 YREARS * 1 YR OLD HOT WATER HEATER * NEW KITCHEN WITH AMPLE CABINETS, ISLAND WITH SITTING AREA AND A SPACIOUS DINING AREA LEADING OUT TO THE POOL * THE GROUND FLOOR ALSO PROVIDES A MASSIVE GAMES ROOM WITH A WOOD BURNING FIREPLACE * PERFECT FOR GATHERINGS AND ENTERTAINTMENT * A FULL BATH WITH A SAUNA ADDS TO THE COMFORT OF THIS HOME * WALK OUTSIDE TO THE COVERED DECK FOR YEAR ROUND USE, HUGE PAVED DECK, POOL GAZEBO AND WATER VIEWS ALL AROUND. WITH 630 FEET OF WATERFRONT WALL PROVIDES NEW OWNERS THE OPPORTUNITY TO BUILD A DOCK WITH A BOAT LIFT AND POSSIBLY A BOATHOUSE * THE LARGE PIECE OF PROPERTY IS PERFECT FOR LOTS OF OUTDOOR ACTIVITIES * LOTS PARKING SPACE FOR MULTIPLE BIG TOYS AND VEHICLES * 3 LARGE OPEN GARAGE SPACES * DON'T MISS THIS ONCE IN A LIFETIME OPPORTUNITY TO OWN A BEAUTIFUL PIECE OF PARADISE * Characters Remaining: 1731 *

1238 Flotilla Drive, Holiday

$550,000

4 Beds ⋅ 3 Baths ⋅ Gulfwinds SubDv. ⋅ 34691 Zip Code

Welcome to 2309 Swordfish Ave, a beautifully maintained 4-bedroom, 3-bathroom, 2,462-square-foot single-story home situated on a spacious 10,320-square-foot lot in the desirable Gulfwinds community of Holiday, Florida. Offering an ideal combination of comfortable living space, thoughtful updates, privacy, and exceptional outdoor amenities, this home is designed for both everyday living and entertaining. The freshly painted interior features a spacious and versatile floor plan with tile flooring throughout the kitchen, breakfast nook, family room, living room, and dining room. The primary bedroom features attractive wood-look tile flooring, while the three additional bedrooms are carpeted. A dedicated office provides an ideal work-from-home space and features brand-new epoxy-resin flooring. Plantation shutters enhance the windows and sliding glass doors throughout the home. The kitchen offers granite countertops, a backsplash installed approximately two years ago, under-cabinet lighting, and a double-door refrigerator. The washer and dryer are included. The primary suite features an updated bathroom with new granite countertops, new tile, new faucets, a walk-in shower, and a walk-in tub. Additional improvements include a roof approximately three years old, a four-year-old HVAC system that has been recently serviced, and a tankless water heater. Outside, the private backyard is enclosed by a vinyl privacy fence and features a screened outdoor living area with a heated saltwater pool and heated hot tub, each equipped with its own separate pump. A newer double-wide side entrance can provide convenient access for a boat, recreational vehicle, or additional vehicle, subject to applicable HOA and county regulations. The property also features an irrigation system and a 3-car garage with newly installed aluminum attic steps for convenient access to additional storage. For added preparedness, the home features a dedicated generator connection with its own junction box and dedicated electrical circuits, providing a convenient setup for connecting a generator when needed. Residents of Gulfwinds enjoy community amenities including a nearby community pool, with HOA services covering community pool access, community grounds maintenance, cable TV, and internet. Gulfside Elementary in Holiday, Florida, closed in mid-2026 and has merged with Paul R. Smith Middle School K1-8. The two nearby, under-capacity campuses combined to form a single unified K-8 school operating at the Paul R. Smith site on Sweetbriar Drive. Conveniently located near the historic Tarpon Springs Sponge Docks, Belle Harbour and Port Tarpon Marinas, Fred Howard Park Beach, boating, dining, shopping, riding and walking trails, the Anclote River and Gulf parks, nearby islands, and spectacular Gulf Coast sunsets. With four bedrooms, three full bathrooms, a dedicated office, multiple living and dining areas, a 3-car garage, private fenced yard, heated saltwater pool and hot tub, tankless water heater, plantation shutters, and numerous recent improvements, 2309 Swordfish Ave offers an exceptional combination of comfort, functionality, and Florida outdoor living. Experience effortless Florida living in Gulfwinds—schedule your showing today!

2309 Swordfish Avenue, Holiday

$575,000

4 Beds ⋅ 3 Baths ⋅ Glenwood Gulf Trace SubDv. ⋅ 34691 Zip Code

Welcome to this spacious 4-bedroom, 3-bath pool home offering approximately 2,857 square feet of comfortable living space in the desirable Gulf Trace community of Holiday. Designed with both everyday living and entertaining in mind, the home features a split-bedroom floor plan, an expansive family room with a cozy fireplace, a generous kitchen with abundant cabinetry, a bright breakfast nook, a formal dining room, separate living room, dedicated laundry room, and an oversized 2-car garage. The private primary suite includes a large walk-in closet and spacious en-suite bath, while three additional bedrooms and multiple bathrooms provide flexibility for family, guests, or a home office. Step outside to an impressive screen-enclosed pool and oversized lanai, creating the perfect setting for year-round Florida living. Ideally located just minutes from the Gulf of Mexico, you'll enjoy easy access to Key Vista Nature Park, Anclote River Park, Gulf beaches, boating, fishing, waterfront dining, and the historic Tarpon Springs Sponge Docks, with Clearwater Beach, Tampa, and Tampa International Airport all within an easy drive. Combining generous living space, a functional layout, and an exceptional location, this home offers the very best of Florida's Gulf Coast lifestyle.

3225 Glenwood Circle, Holiday

$509,000

2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv. ⋅ 34691 Zip Code

NEVER FLOODED DURING HURRICANE HELENE! This is a rare opportunity to own a Gulf-access waterfront home that offers both an exceptional boating lifestyle and added peace of mind. According to the seller, the home has never experienced flooding or water intrusion, making it an outstanding choice for buyers seeking waterfront living with confidence. Nestled in the highly desirable Baileys Bluff Estates, this move-in-ready waterfront home sits on an oversized 0.31-acre lot with approximately 55 feet of saltwater canal frontage, offering direct Gulf access in about one minute. Bring your boat, kayaks, paddleboards, and fishing gear—your waterfront adventures begin right in your own backyard. Boaters will appreciate the private boat ramp, 10,000-pound boat lift, with, stationary dock, and concrete seawall, making launching and storing your boat effortless. Spend your days fishing, scalloping, island hopping to Anclote Key, or watching spectacular Gulf sunsets just minutes from home. Inside, you'll find an inviting floor plan featuring 2 bedrooms, 1.5 baths, an updated kitchen with solid wood cabinetry, updated bathrooms, comfortable living spaces, and a bright Florida room overlooking the tranquil canal. The home has been well maintained and is ready for its next owner. Major recent improvements provide outstanding value, including a brand-new roof (2025) and a brand-new air conditioning system, helping reduce future maintenance costs while increasing buyer confidence. The spacious backyard provides plenty of room to entertain, garden, or simply relax while enjoying peaceful waterfront views and abundant Florida wildlife. Located just minutes from Anclote River, the Gulf of Mexico, Key Vista Nature Park, the famous Tarpon Springs Sponge Docks, beaches, waterfront dining, shopping, and medical facilities, this home offers the perfect balance of recreation and convenience. Whether you're looking for a year-round residence, seasonal retreat, or waterfront investment, opportunities like this are becoming increasingly difficult to find. No HOA, Move-in ready. Schedule your private showing today and discover why this exceptional Gulf-access waterfront property is one of Holiday's best boating values.

3318 Pineview Drive, Holiday

$579,000

3 Beds ⋅ 4 Baths ⋅ Ibis Sub SubDv. ⋅ 34691 Zip Code

"Luxury Living in an Exclusive Gated Community" Experience coastal elegance in this custom-built executive residence, privately situated on a quiet cul-de-sac within an exclusive gated community. Offering 2,367 square feet of thoughtfully designed living space, this exceptional three-story home combines luxury, comfort, and functionality with partial Gulf views from multiple balconies. From the moment you arrive, the impressive stamped concrete driveway and striking architectural design create unforgettable curb appeal. Inside, you'll find soaring ceilings, custom 8-foot doors, elegant crown molding, engineered hardwood flooring, marble and travertine finishes, and an open-concept floor plan designed for both entertaining and everyday living. The gourmet kitchen is truly the heart of the home, featuring granite countertops, abundant custom cabinetry, a walk-in pantry, breakfast bar, and newer stainless-steel appliances—perfect for preparing meals while staying connected with family and guests. Escape to the luxurious owner's retreat occupying the entire upper level. This private sanctuary offers partial Gulf views, a spacious walk-in closet, and a spa-inspired ensuite featuring dual vanities, an oversized walk-in shower, and a relaxing whirlpool tub. Step outside and enjoy Florida living at its finest. Four travertine balconies provide multiple places to relax and enjoy the coastal breeze, while the beautiful in-ground pool and expansive paver patio create the perfect setting for entertaining family and friends. The oversized garage offers room for multiple vehicles, a workshop, abundant storage, and even includes a convenient full pool bath.Recent upgrades provide peace of mind and modern convenience, including: New roof (2021), Newer-zone HVAC system, Updated stainless-steel kitchen appliances Central vacuum system Premium flooring throughout. Ideally located enjoy indoor pickleball, weekly gymnasium schedule, summer camp, soccer fields, baseball, tennis and more at J. Ben Harrill Recreation Center is a short walk from your front gate. Just minutes from Anclote Gulf Park, public boat ramps, Gulf beaches, the Pinellas Trail, and the world-famous Tarpon Springs Sponge Docks, you'll also enjoy convenient access to shopping, dining, and endless waterfront recreation. Luxury, location, and lifestyle come together in one extraordinary home. Schedule your private showing today and discover why this exceptional property is one you won't want to miss.

3020 Sheppards Crook Court, Holiday

$575,000

5 Beds ⋅ 3 Baths ⋅ Key Vista Prcl 18 SubDv. ⋅ 34691 Zip Code

Welcome to this beautiful 5 bedroom 3 bathroom two-story home located in the highly desirable community of Key Vista. Upon entry you immediately feel welcome and at home with the large formal dining area and front living area with electric fireplace. The large kitchen boasts tall cabinetry and plenty of counter space with amazing views of the tree line that reflects along the waters edge. One bedroom with private bathroom is conveniently located on the first floor and four bedrooms are located on the second story with the large master bedroom with private bathroom also has an adjoining bonus room. Enjoy the privacy of no rear neighbors with breathtaking views of nature in your own backyard!!! Only minutes away from some of the most beautiful beaches and parks in Florida. Schedule your private showing today!!!

1914 Oswego Drive, Holiday

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