Homes for Sale with a Pool in Holiday, FL

Welcome to your own tropical oasis and the waterfront lifestyle you’ve been dreaming of! This beautifully renovated 3-bedroom, 3-bathroom waterfront pool home with a spacious bonus room is situated on a large lot along the Anclote River, offering approximately 70 feet of seawall and direct access to the Gulf. The sellers will have the solar panels removed and the roof replaced prior to closing, providing added peace of mind for the new owners. Inside, a desirable split-bedroom floor plan and new wood-plank tile flooring create a stylish and functional living space. The spacious living room flows seamlessly into the dining area, while sliding glass doors open to an expansive screened-in patio, bringing the best of Florida’s indoor-outdoor lifestyle home. A hallway off the main living area leads to two generously sized guest bedrooms. One features a private bathroom with convenient access to the pool area, while the second offers a large walk-in closet and easy access to the additional guest bathroom. The beautifully appointed kitchen features stainless-steel appliances, wood cabinetry, granite countertops, and a cozy breakfast nook—perfect for casual meals or morning coffee. The spacious primary suite offers a walk-in closet and an updated bathroom with a convenient step-in shower. Just beyond the primary suite, a large bonus room provides versatile space for a home office, den, nursery, gym, or additional living area. Step outside and discover your private Florida retreat. The expansive screened-in patio overlooks a sparkling swimming pool surrounded by stamped-concrete decking, while the large, fenced backyard provides plenty of space to relax, entertain, and enjoy the outdoors. A composite deck with pergola creates an inviting setting for outdoor dining, lounging, and soaking up the Florida sunshine year-round. And for boating enthusiasts, this property truly stands apart. Just steps from the deck, a composite boat dock with a 10,000-pound boat lift provides convenient access to the Anclote River and the Gulf. Spend the day boating, exploring nearby tropical islands, or enjoying the area’s beautiful sandy beaches—all from your own waterfront backyard. Bring your boat, your family, and your love of the water. This is Gulf Coast living at its best!

1324 Chancellor Drive, Holiday

4349 Tahitian Gardens Circle Unit G, Holiday

$95,000

1 Beds ⋅ 1 Baths ⋅ Tahitian Gardens Condo SubDv.

Welcome to easy Florida living in the active 55+ community of Tahitian Gardens! This charming 1-bedroom, 1-bathroom villa-style condo offers comfortable, low-maintenance living in a community where there is always something to do. Fresh interior paint and luxury vinyl flooring create a clean feel, while a newer water heater (2022) helps make this home truly move-in ready. Residents of Tahitian Gardens can take advantage of the community pool and a variety of activities and social events, including cookouts, fashion shows, bingo, shuffleboard, bocce ball, horseshoes, sailboat races, dances and line dancing. Game enthusiasts can enjoy pinochle, euchre, mahjong, dominoes and other card games. Located only 10 minutes from Tarpon Springs and sponge docks, this community is close to restaurants, shopping and activities. Whether you're looking for a full-time Florida home, a seasonal getaway, or a place to enjoy an active and social lifestyle, this villa offers an inviting opportunity to make Florida living simple.

4349 Tahitian Gardens Circle Unit G, Holiday

$284,900

3 Beds ⋅ 2 Baths ⋅ Oak Hill SubDv.

This 3-bedroom, 2-bathroom home is located in the Oak Hill Unit neighbourhood. This home features a welcoming open floor plan that creates a seamless flow throughout the main living spaces, perfect for both everyday life and entertaining. The updated kitchen is beautifully appointed with granite countertops and stainless-steel appliances. For your privacy, the primary bedroom includes a dedicated attached bathroom. Step outside to discover your own private swimming pool, offering a great space to relax and unwind. Conveniently located near public schools and just a short drive to Gulf beaches, shopping, dining, and other amenities. Schedule your private showing today! One or more photos in this listing have been virtually staged.

2641 Flintwood Drive, Holiday

$479,900

3 Beds ⋅ 2 Baths ⋅ Key Vista Ph 04 SubDv.

Welcome to this beautifully updated three-bedroom, two-bathroom pool home in the gated community of Key Vista in Holiday! Offering an impressive combination of thoughtful updates, smart-home technology, and resort-style amenities, this home is designed for comfortable and easy Florida living. Major improvements include a 2024 roof with a 25-year warranty, 2024 water heater, 2019 windows, 2021 Shaw Luxury Vinyl Plank flooring with 5¼-inch baseboards, and a 2020 AC compressor replacement featuring a 3-ton, 14 SEER heat pump with a 10-year warranty. The AC condenser is also from 2020. Additional updates include 2019 kitchen appliances, 2021 garage door opener and springs, 2017 washer and dryer, 2021 renovations to both bathrooms, and permanent exterior lighting installed in 2025. The open-concept interior offers a spacious and inviting layout with a large kitchen island perfect for meal preparation and casual dining, granite countertops, stainless steel appliances, abundant cabinetry, and a breakfast nook overlooking the pool. A separate dining room provides additional space for entertaining. The spacious primary bedroom features a vaulted ceiling, ceiling fan, and relaxing pool views. The beautifully renovated primary bathroom features a dual-sink granite-top vanity, glass-enclosed shower, and newly tiled finishes, while the second bathroom was also renovated in 2021. Step outside and enjoy your private pool and fenced backyard, designed for effortless outdoor living. The pool features Hayward OmniLogic automation that allows you to control the pump, spa, and heater remotely from your smartphone, making it easy to turn everything on before you even step outside. The pool and spa lights can also be operated remotely, eliminating the need to go outside the screened enclosure to adjust switches. A 2025 salt cell replacement provides added convenience, while 2026 LED pool and spa lights offer enhanced lighting and remote operation. The pool also features beautiful natural travertine decking, a built-in pool-wall vacuum system, and an included Hayward robotic pool cleaner. The extended screened lanai features an Elite roof, creating additional covered outdoor living space. Smart technology continues throughout the home with a Sensi smart thermostat that can be controlled through your smartphone and a smart garage door opener that can notify you if the garage is left open too long or when you leave home. The home includes a generator that provides backup power for lighting, ceiling fans, and other select areas of the home that is prewired with a transfer switch, which was installed around 2023. Additional exterior features include gutters, a professionally installed drainage system, hurricane shutters for the entire home, front-door and Palladian-window mesh hurricane protection, and a professionally painted exterior using Sherwin-Williams Emerald Shield paint in 2021. Ring Doorbell and Ring security cameras provide additional smart-home convenience and security around the front garage area and pool lanai. The Key Vista community offers an outstanding lifestyle with a community pool, clubhouse, sport courts, and additional amenities, while the master association includes cable. Conveniently located near the J. Ben Harrill Recreation Complex, numerous parks and trails, dining and shopping options, and zoned schools. Schedule your showing today!

2530 Arrowpointe Drive, Holiday

$135,000

2 Beds ⋅ 2 Baths ⋅ Holiday Lake Villas Condo SubDv.

Virtually Staged. Beautiful Corner unit in Holiday Lake Villas Condos. This beauty is located directly across from the Club House and Pool. There are 2 bedrooms and 2 bathrooms. The primary bedroom features sliding glass doors directly to the enclosed porch, a walk in closet, a mirrored dressing table as well as a dual sink vanity. The kitchen has a breakfast nook and a pass through to the living room, dining room. Unit has been beautifully updated with fresh paint, flooring and appliances. This condo was built in 1981 and has 1318 sq ft living area plus a 216 sq ft enclosed porch. Just perfect for a maintenance free winter home or a fulltime residence

3936 Sailmaker Lane, Holiday

$549,900

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

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

$449,900

3 Beds ⋅ 2 Baths ⋅ Glenwood Gulf Trace SubDv.

Recent Appraisal square footage is living space of 2151! Beautifully Updated 3-Bedroom Home on an Oversized Cul-de-Sac Lot Welcome home! This beautifully maintained 3-bedroom, 2-bath home sits on an oversized corner lot in a desirable cul-de-sac, offering extra space, privacy, and flexibility. With an impressive list of updates already completed, this home is truly move-in ready! 2019 — Exceptional Kitchen, Pool & Window Upgrades • Double-Pane, Impact-Rated Windows Installed, providing enhanced protection, energy efficiency, comfort, and peace of mind while also enhancing curb appeal and comfort. • Pool refinished and filtration system replaced. • Granite countertops add beauty, durability, and elegance. • Stainless steel appliances create a modern kitchen. • Soft-close kitchen cabinet drawers provide a premium finishing touch. 2020 — Added Protection • Gutters installed, helping direct rainwater away from the home. Well-fed irrigation system helps keep the lawn and landscaping looking green, healthy, and beautiful while providing an economical irrigation source. 2023 — Major System Improvements • Roof replaced, providing valuable peace of mind. • HVAC system replaced, keeping the home comfortable year-round. 2024 — Fresh Exterior • Exterior painted, delivering a fresh, attractive appearance and enhanced curb appeal. 2025 — Garage Upgrade • Garage door replaced, adding functionality, security, and curb appeal. NEW — Beautiful Flooring Luxury Vinyl Plank flooring has been newly installed throughout the main living spaces, creating a stylish, durable, and easy-to-maintain foundation. The Secondary bedrooms feature comfortable carpeting, creating cozy private spaces. Flexible Space to Make Your Own The home's 3-bedroom, 2-bath layout also offers additional space that can be transformed into an office, craft room, hobby space, or potentially a 4th bedroom, depending on your needs and applicable requirements. THE BIG STORY This home offers the rare opportunity to enjoy the benefits of years of thoughtful improvements without taking on the projects yourself. Major updates include the roof, HVAC, windows, pool, filtration system, gutters, exterior paint, garage door, kitchen features, irrigation system, and NEW flooring. Add the oversized cul-de-sac lot, private pool, flexible living space, and move-in-ready condition, and this home delivers an incredible combination of comfort, style, functionality, and value! Come see it, and make it yours!

3225 Hearthstone Court, Holiday

$234,900

3 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.

MOVE-IN READY! Welcome home to this charming 3-bedroom, 2-bathroom home featuring a desirable split-bedroom floor plan and spacious living areas. The large living room flows into the dining area, while the family room is open to both the dining room and kitchen, creating a great layout for everyday living and entertaining. Tile flooring runs throughout the home. The fenced backyard offers privacy and relaxation with a cute gazebo and no rear neighbors. An optional Civic Association offers access to a community pool. Enjoy an abundance of nearby recreational opportunities, including Anclote River Beach Park with boat ramp and fishing pier, Key Vista Nature Park, Eagle Point Park with playground and kayak trail, and Green Key Beach on the Gulf. Come enjoy your own piece of Paradise!

3431 Overland Drive, Holiday

$249,999

3 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.

Virtually Staged. TROPICAL POOL & POND PARADISE HOME FEATURING A SPARKLING SWIMMING POOL, 3 BEDROOMS, 2 BATHROOMS AND A LARGE COVERED LANAI AND SCREEN-ENCLOSED POOL-DECK. NEW ROOF, NEW KITCHEN, NEW AC, NEW APPLIANCES, QUARTZ COUNTERSTOPS, NEW LUXURY WATERPROOF VINYL PLANK FLOORS, new electrical panel, new pool pump and new cartridge filter! All new interior paint and fixtures. Beautiful curb appeal with a spacious driveway and covered front porch. 22 Ft long garage with side entrance door. Private backyard with pond access and beautiful wildlife views. Perfectly located near great shopping, restaurants, parks and beaches! Enjoy the fun in the sun that a tropical paradise pool home offers!

3349 Overland Drive, Holiday

$139,900

2 Beds ⋅ 2 Baths ⋅ Holiday Lake Villas Condo SubDv.

Come see this well-maintained 2-bedroom, 2-bath villa-style condo in the desirable Holiday Lake Villas community. This single-story home offers 1,114 square feet of comfortable living space with a practical layout and a number of attractive updates. The kitchen, fully redone in 2025, features bright white cabinetry, granite countertops, stainless steel appliances, and a convenient breakfast area overlooking the front of the home. The spacious living and dining areas feature durable wood-look flooring and open naturally to the enclosed Florida room through large sliding glass doors, creating an additional space to relax, entertain, or enjoy the Florida weather year-round. The Florida room also offers extra INTERIOR storage space that not every home in this community has. This home features all new windows replaced in 2025 as well, for YEARS of peace of mind. Both bedrooms are comfortably sized and offer ample closet space, while the two full bathrooms provide convenience for residents and guests. An interior laundry closet includes a full-size Samsung washer and dryer, and the home also comes with an assigned covered carport space. Outside, the property features a landscaped front entry and a private rear patio area overlooking a grassy common area. Holiday Lake Villas offers a low-maintenance lifestyle with community amenities including a clubhouse, pool, and recreational facilities. Conveniently located in Holiday with easy access to shopping, dining, parks, beaches, and the Tarpon Springs area, this home offers an excellent opportunity for anyone looking for a comfortable Florida residence in an established community.

3828 Sailmaker Lane, Holiday

$289,000

2 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv.

Welcome to your slice of the Florida waterfront lifestyle. This 2-bedroom, 2-bathroom home sits directly on the Anclote River with deeded Gulf of Mexico access, a rare opportunity to own true boating water at an approachable price point, on a nice block of well-kept homes. Step into your own private oasis with a screened, in-ground pool overlooking the river, a private dock with new wood decking ready for your boat, a seawall in good condition, and a spacious backyard made for sunset views and morning coffee on the water, while new windows across the back of the home flood the living space with natural light and frame those river views beautifully. This home has been well cared for where it counts most, with a new roof (2025), HVAC (approx. 2 years), fencing (1 year old), and pool pump (1.5 years old) already updated, making this a true opportunity for an investor or a buyer ready to add cosmetic value through new flooring, kitchen, and bath finishes and build significant equity, whether renovating to sell, to rent, or to make it your own. Tucked in the Flotilla Dr riverfront enclave of Holiday, the home is minutes from Anclote River Park, with its boat ramp, kayak launch, and Gulf-access swimming, and just a short drive from the world-famous Tarpon Springs Sponge Docks, known for its historic Greek waterfront district, dolphin cruises, and waterfront dining, with boaters able to head straight out the Anclote River to Anclote Key Preserve State Park or nearby Fred Howard Park and Sunset Beach. Families will also appreciate the school zoning for Sunray Elementary, Paul R. Smith Middle School, and Anclote High School. Homes with true river frontage and Gulf access rarely come to market at this price point, so bring your contractor and your vision, and turn this riverfront gem into something spectacular!

1332 Flotilla Drive, Holiday

$349,900

3 Beds ⋅ 2 Baths ⋅ Gulfwinds SubDv.

Maintenance-Free Living Meets the Florida Lifestyle! This beautifully designed 3-bedroom plus den, 2-bath villa offers 1,876 square feet of thoughtfully designed living space and truly lives like a single-family home—without the maintenance headaches. Best of all, it is not in a flood zone and offers a 2-car garage! Step inside to soaring ceilings and an inviting open-concept layout where the kitchen, dining area, and family room flow seamlessly together. The spacious kitchen is a standout, featuring 42-inch wood cabinetry, newer stainless steel appliances, an undermount sink, closet pantry, and an oversized granite island that is perfect for meal prep, casual dining, or entertaining friends and family. The private primary suite is your own retreat, complete with a large walk-in closet and a beautifully appointed en suite bathroom featuring dual granite vanities, an oval soaking tub, walk-in shower, and private water closet. Bedrooms two and three are thoughtfully located on the opposite side of the home, along with the second full bathroom, providing excellent privacy and flexibility for family, guests, or hobbies. The den with French doors makes an ideal home office, reading room, or additional sitting area. Outside, the screened-in paver lanai creates the perfect space to enjoy Florida's year-round outdoor living, while the privacy-fenced backyard provides an added sense of seclusion. The interior laundry room also offers valuable storage and convenience. This home has been lovingly updated with hurricane windows throughout (2023), a new A/C in 2021 with a 10-year warranty, hurricane-impact back door (2023), new garage door opener (2026), updated faucets and showerheads, updated lighting, and newer kitchen appliances. The low HOA fee makes life even easier by covering lawn service, internet, cable, exterior maintenance, roof replacement, and more. The community pool is just around the corner, giving you a convenient place to relax and enjoy the Florida sunshine without the upkeep of a private pool. Located in desirable Gulfwinds, you are close to schools, marinas, fishing piers, shopping, golf, dog parks, splash parks, and some of the area's most beautiful Gulf Coast destinations. Enjoy nearby Anclote River Park, Anclote Gulf Park, and the famous Tarpon Springs Sponge Docks, where you can explore unique shops, enjoy Greek cuisine, and experience local culture and events. A new walking and biking trail system also provides convenient connections to nearby parks and the Pinellas Trail. If you're looking for a beautifully updated home with the space and feel of a single-family residence, but the convenience of maintenance-free living, this Gulfwinds villa deserves a spot at the top of your list.

2220 Parrot Fish Drive, Holiday

Homes for Sale with a Pool in Holiday, FL

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