Between $500,000 - $600,000 Holiday FL Real Estate, Homes, Condos for Sale

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

Waterfront living with Gulf access in Holiday. This 3-bedroom, 2-bathroom pool home at 2123 Bayou Dr sits on a saltwater canal with a private dock and seawall. It has 1,962 square feet of living space and a backyard made for the Florida boating lifestyle. Inside, the comfortable layout gives you room to spread out, with bright living areas for everyday living and hosting friends and family. The primary suite has its own private bath, and the two other bedrooms work well for guests, a home office, or hobbies. Step outside to your private pool overlooking the canal, the perfect spot to unwind and catch the breeze off the water. Tie up at your own dock, protected by a seawall, and cruise straight out to the Gulf of Mexico for fishing, sandbar days, and sunset rides. Boaters, kayakers, and anglers will love having the water right at their back door. You're minutes from Key Vista Nature Park, Anclote River Park, Gulf beaches, the historic Tarpon Springs Sponge Docks, and the shopping and dining along US-19. Clearwater, Tampa, and Tampa International Airport are an easy drive. Saltwater canal homes with a pool, dock, and Gulf access are hard to find. Schedule your private showing today.

2123 Bayou Drive, Holiday

$550,000

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

Welcome to 1937 Blue River Road, located in the highly sought-after Key Vista community in Holiday. This spacious 4-bedroom, 3-bath home with a 3-car garage also features a bonus room and additional flex space, offering plenty of room for a home office, gym, playroom, media room, or guest space. The large kitchen features a generous eat-in area and several newer updates, including the stove, dishwasher, and sink, along with updated sinks and fixtures throughout the home. The interior has also been freshly painted, giving the home a bright, refreshed feel. Major improvements include a 2023 roof and updated front and rear windows with hurricane protection for added peace of mind. The outdoor living space is one of the home’s best features. Situated on an extra-large conservation lot in a non-flood zone, the backyard offers a peaceful and private setting with tranquil views of the surrounding natural landscape. A spacious screened lanai provides the perfect place for morning coffee, outdoor dining, or relaxing in the shade, while the separate pergola area with paver decking creates an additional outdoor entertaining space. Whether hosting friends, grilling on the weekends, or simply enjoying the quiet conservation views, the backyard offers multiple areas to enjoy Florida living year-round. The landscape lighting adds ambiance in the evenings and highlights the outdoor space beautifully. Additional features include an EV charger, garage shelving, and the convenience of a 3-car garage with plenty of room for vehicles, storage, and hobbies. With its flexible floor plan, newer roof, expansive conservation lot, inviting outdoor living areas, and desirable Key Vista location, this home offers an exceptional combination of space, privacy, and Florida lifestyle living.

1937 Blue River Road, Holiday

$500,000

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

SALTWATER POOL. NO REAR NEIGHBORS. 4 BEDROOMS + DEN. This Gulfwinds home brings together the space, privacy, and Florida lifestyle you are looking for. With 2,480 square feet and 3 FULL baths, the SINGLE-STORY split bedroom layout gives you plenty of room to spread out. The spacious kitchen opens to the family room, while separate living and dining areas add flexibility for entertaining, working from home, or simply having a little extra breathing room. Step outside to your own tropical retreat. The screened SALTWATER POOL offers plenty of space to relax, dine, and entertain, while NO REAR NEIGHBORS adds to the sense of privacy. And your furry friends will be happy with pet safe turf running under foot! Several of the big-ticket items are already done, including a NEW ROOF IN 2026, NEW WATER HEATER IN 2026, BRAND-NEW WATER SOFTENER, and A/C replaced in 2018. Gulfwinds offers a COMMUNITY POOL, SIDEWALKS winding throughout the neighborhood, and COMMUNITY PONDS for an evening stroll. And the location? You’re approximately 3 MINUTES FROM WATERFRONT DINING and just 5 MINUTES FROM THE TARPON SPRINGS SPONGE DOCKS, putting restaurants, shops, and one of the area’s most recognizable waterfront destinations practically in your backyard. Come see how much this home — and this location — has to offer.

1419 Blue Marlin Boulevard, Holiday

$549,900

4 Beds ⋅ 4 Baths ⋅ Dodge City First Add SubDv. ⋅ 34690 Zip Code

Welcome to 5657 Oceanic Road, Holiday, Florida — a unique property offering an impressive 3,535 square feet of living space, a massive 1,900-square-foot garage, and a large pool, all situated on an oversized lot in a quiet, peaceful neighborhood. Designed for those who value space, flexibility, and comfort, this property offers room to live, work, entertain, and store vehicles, recreational equipment, or hobby essentials. The expansive garage provides exceptional versatility for car enthusiasts, workshop needs, storage, or additional workspace. Upstairs, the spacious primary suite features its own private living room or sitting area, creating a relaxing retreat separate from the rest of the home. Two dedicated office spaces offer excellent flexibility for remote work, a home-based business, creative pursuits, or additional workspace. Step outside and enjoy the large pool and oversized lot, offering plenty of room to relax, entertain guests, and enjoy the Florida lifestyle. Located in a quiet neighborhood, this property combines generous interior space with outdoor enjoyment and a sense of privacy. An exceptional financing opportunity adds even more appeal: a potential assumable VA loan at an outstanding 2.37% interest rate for qualified VA buyers, subject to lender approval and eligibility requirements.

5657 Oceanic Road, Holiday

$549,900

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

GREAT PRICE REDUCTION * HURRY BEFORE IT'S GONE * WHERE CAN YOU GET A 1.2 ACRE PIECE OF WATERFRONT PROPERTY WITH 5 BEDROOMS, 4 .5 BATHS AND UNOBSTRUCTED WATER VIEWS * 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, WITH 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 OF 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 * PRIVATE FINANCING WITH VERY GOOD TERMS AVAILABLE * REPAIRS NEEDED BUT AT THIS PRICE THE NEW OWNER WILL STILL HAVE HIGH BUILT IN EQUITY IN THE HOME Characters Remaining: 1731 *

1238 Flotilla Drive, Holiday

$545,000

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

$525,000

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

$559,000

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

Under contract-accepting backup offers. "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

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