Holiday Homes with Pool Community features

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Newest Holiday Homes with Pool Community features

$239,900

3 Beds ⋅ 2 Baths ⋅ TB8542483 MLS

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

Listing courtesy of FUTURE HOME REALTY INC. 813-855-4982

$155,000

2 Beds ⋅ 2 Baths ⋅ TB8542704 MLS ⋅ 3828 BLDG.

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

Listing courtesy of LIPPLY REAL ESTATE. 727-314-1000

$359,900

3 Beds ⋅ 2 Baths ⋅ TB8542321 MLS

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

Listing courtesy of RE/MAX ALLIANCE GROUP. 727-845-4321

$134,900

2 Beds ⋅ 2 Baths ⋅ TB8541598 MLS ⋅ 16 BLDG.

Come see this unique opportunity to own in the desirable, 55+ gated community of Tahitian Gardens! This partially furnished corner-unit condominium offers two bedrooms and one-and-a-half baths, making it ideal as a primary residence or second home. The bright, open living area features cross-cut tile flooring and floor-to-ceiling windows that fill the space with natural light. The kitchen flows into a separate dining area. The primary bedroom offers a walk-in closet and half bath, while the main bathroom features a full-size walk-in shower. An included washer/dryer add everyday convenience. Recent improvements include energy-efficient storm windows, a newer roof (2021), and an on-demand water heater (2022). A new AC System was installed in 2016. Relax on the private patio and enjoy a walk around the lake located directly behind the unit. Tahitian Gardens offers an active community lifestyle with a heated swimming pool, shuffleboard courts, two community buildings, arts and crafts, bingo, a bicycling club, and a variety of activities and events. Conveniently located near shopping, dining, Tarpon Springs, Howard Park Beach, and other Gulf Coast beaches, this well-cared-for condo is ready for you. Schedule your private showing today!

4330 Tahitian Gardens Circle Unit A, Holiday

Listing courtesy of COASTAL FLORIDA REAL ESTATE. 727-471-9115

$550,000

4 Beds ⋅ 3 Baths ⋅ TB8540451 MLS

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

Listing courtesy of KELLER WILLIAMS REALTY- PALM HARBOR. 727-772-0772

$279,900

3 Beds ⋅ 2 Baths ⋅ TB8540537 MLS

Virtually Staged. Welcome to your beautifully updated Florida retreat in the heart of Holiday — a move-in-ready 3-bedroom, 2-bath home where modern finishes meet everyday comfort. Step inside and feel the warmth of a bright, open floor plan that flows effortlessly from the living room to the kitchen and into the enclosed Florida room, creating the perfect space for relaxing, entertaining, or enjoying quiet mornings with coffee. The stylishly renovated kitchen features white shaker cabinets, quartz countertops, and a convenient pass-through window that brings natural light into the home and makes hosting effortless. Both bathrooms have been tastefully updated, and the entire home shines with new luxury vinyl flooring, fresh interior and exterior paint, and a brand-new roof for peace of mind and long-term value. Enjoy the flexibility of an enclosed Florida room — perfect as a second living area, playroom, or home office — along with a fenced backyard offering privacy and space for pets, gardening, or weekend gatherings. A one-car garage adds convenience and storage options. Enjoy access to a sparkling pool, clubhouse, and playground, adding lifestyle amenities without the high HOA fees. And with the Gulf of Mexico, shopping, dining, parks, and recreation just minutes away, this home offers the perfect blend of comfort and convenience in a prime Holiday location. This beautifully refreshed home is ready for its next chapter — all that’s missing is you.

3128 Harvardston Loop, Holiday

Listing courtesy of EXP REALTY LLC. 866-308-7109

$375,000

3 Beds ⋅ 2 Baths ⋅ TB8538169 MLS

Virtually Staged. Welcome to this beautifully updated 3-bedroom, 2-bathroom, 2-car garage home in the desirable gated community of Key Vista! Thoughtfully refreshed, this warm and inviting home features luxury vinyl plank flooring, fresh interior paint, modern lighting and ceiling fans, beautiful bathrooms, a new water heater, and a new French-door refrigerator. Enjoy the low HOA fee (and no CDD) that includes cable and internet, along with resort-style amenities including a clubhouse, heated pool and hot tub, fitness center, tennis and pickleball courts, volleyball courts, playground, and optional RV/boat storage. Even better, travel out the back gate with convenient access to the community’s recreational amenities, putting them just a short walk from home. For added peace of mind, the property is located in Flood Zone X and sustained no damage from Hurricanes Helene or Milton. Inside, the spacious kitchen offers abundant cabinetry and counter space and flows comfortably into the living and dining areas, creating an inviting space for everyday living, casual meals, and entertaining family and friends. Step outside to the covered lanai and fully fenced backyard with vinyl privacy fencing—a private outdoor retreat perfect for morning coffee, relaxing at the end of the day, spending time with pets, or gathering with family and friends. Key Vista offers a wonderful Florida lifestyle with Anclote Nature Park, Anclote Beach, and the community recreation center nearby, plus convenient access to boating, fishing, shopping, dining, and the Gulf Coast. With its beautiful features, low HOA, gated-community amenities, private backyard, and location, this Key Vista home is ready to welcome its next owner!

2638 Big Pine Drive, Holiday

Listing courtesy of REDFIN CORPORATION. 813-518-8756

$139,900

2 Beds ⋅ 2 Baths ⋅ TB8536062 MLS

You'll love coming home to this beautifully remodeled 2-bedroom, 2-bathroom double-wide mobile home in the highly sought-after 55+ gated community of Lake Conley MHP, where you own the land! Enjoy peaceful water views from the spacious, fully enclosed front porch—the perfect spot to sip your morning coffee or unwind at the end of the day. From the moment you enter the meticulously maintained gates of Lake Conley MHP, you'll appreciate the pride of ownership, beautifully landscaped grounds, and welcoming atmosphere that define this exceptional community. Step inside this move-in-ready home—just bring your toothbrush! The light-filled, open floor plan has been thoughtfully updated with quality improvements throughout. The remodeled kitchen (2019) features new cabinetry and offers plenty of storage and workspace, while a new dishwasher was installed in 2025. Additional updates include new windows and blinds (2018), laminate flooring and subfloors (2018), remodeled bathrooms (2020), a new A/C system (2021), a decorative driveway (2022), a new electrical panel (2023), new porch screens (2023), new skirting (2024), and a roof resealed with a new vent installed (2025). Lake Conley MHP offers affordable living with low monthly HOA fees of just $63.82. This pet-friendly, golf cart community features an active social calendar, a heated swimming pool, shuffleboard courts, and a clubhouse. Residents also enjoy access to a private fishing dock and community boat ramp. RV and boat storage is available on-site for an additional annual fee, subject to availability (small spaces: $240/year; large spaces: $480/year). Conveniently located in Holiday, you'll be just minutes from shopping, restaurants, entertainment, beautiful Gulf beaches, Honeymoon Island, and the famous Tarpon Springs Sponge Docks. Tampa International Airport is approximately 35 minutes away, and Orlando's world-renowned theme parks are about a 90-minute drive. Don't miss this incredible opportunity to own a beautifully updated home in one of the area's most desirable 55+ communities. Pack your bags—you've just found your new home! Bonus Opportunity!!!!! Golf cart available for purchase! The golf cart may be included with the sale of the home with a full-price offer.

2122 Waterview Drive, Holiday

Listing courtesy of PENNY GOULD REALTY INC. 727-789-5899

$114,900

1 Beds ⋅ 1 Baths ⋅ O6429748 MLS ⋅ 8 BLDG.

Enjoy one of the most picturesque waterfront settings in the privately gated community of Tahitian Gardens! This beautifully maintained condominium sits directly on the lake overlooking the community fountain, offering peaceful water views from the comfort of your own home. A mature shade tree creates a relaxing outdoor setting, while the nearby cul-de-sac parking adds everyday convenience that few units enjoy. Inside, you'll find luxury vinyl flooring throughout, an updated bathroom with a new vanity, and updated fixtures throughout the home. Major improvements include a new A/C system (2024) and new water heater (2025), providing peace of mind for years to come. Expansive windows showcase the tranquil lake and fountain, filling the living space with natural light and beautiful views. Located within the 55+ Tahitian Gardens community, residents enjoy a clubhouse, community pool, beautifully maintained grounds, scenic walking paths, and a convenient location just minutes from shopping, dining, medical facilities, parks, beaches, and the Gulf Coast.

4318 Tahitian Gardens Circle Unit F, Holiday

Listing courtesy of VERANDA REALTY GROUP. 727-372-8053

$119,000

2 Beds ⋅ 2 Baths ⋅ TB8533456 MLS ⋅ 25 BLDG.

Welcome to Holiday Lake Villas, a 55+ community in Holiday! This affordable, move-in-ready, one level end unit villa offers 2 bedrooms, 2 full baths, and approximately 1,316 square feet of comfortable living space. The spacious kitchen features abundant cabinet space and overlooks the bright living room, where vaulted ceilings and plenty of natural light create an open and inviting atmosphere. The spacious primary suite includes a walk-in closet and a private bathroom with dual vanities. The home also features a generously sized second bedroom and an enclosed Florida room that provides flexible bonus space. Additional highlights include a new A/C system installed in 2026, a newer water heater, and a washer and dryer. Community amenities include a pool, clubhouse, shuffleboard courts, and gathering areas. Conveniently located near shopping, restaurants, historic Tarpon Springs, the Sponge Docks, parks, and Gulf Coast beaches. Enjoy easy Florida living in this welcoming community! Property is being sold as-is for the seller's convinience and has been priced accordingly.

3960 Sailmaker Lane, Holiday

Listing courtesy of PALM PARADISE REALTY GROUP. 239-955-7256

$125,000

2 Beds ⋅ 2 Baths ⋅ TB8534758 MLS ⋅ 4313 BLDG.

BEING SOLD FURNISHED JUST BRING YOUR PERSONAL BELONGINGS. UPRIGHT PIANO WILL BE REMOVED IF NOT WANTED. DISH WASHER IS NOT WORKING AND WILL NOT BE REPLACED. REFRIGERATOR IS 5 YEARS OLD, A/C INSTALLED 2/2023, WATER HEATER 2007, STACKED WASHER & DRYER 2024. ROOF SHINGLES REPLACED BY HOA. AS YOU ENTER THE GATE TIRN LEFT BUILDING IS THE FIRST BUILDING ON YOUR LEFT UNIT B. EASY ACCESS COMING AND GOING, NO NEED TO DRIVE OVER TO MANY SPEED BUMPS. VERY CONVENIENT. WORTH THE DRIVE TO TAKE A LOOK. TAHITIAN GARDENS IS A VERY CONVENIENT LOCATION TO SHOPPING AND HEADING TO THE SPONGE DOCKS IN TARPON SPRINGS.

4313 Tahitian Gardens Circle Circle Unit B, Holiday

Listing courtesy of CHARLES P CARTER. 727-389-3418

$79,500

1 Beds ⋅ 2 Baths ⋅ TB8534345 MLS

LOOKING FOR A WINTER GET-AWAY OR A 1 BEDROOM 1 AND 1/2 BATH YEAR-AROUND HOME. THIS HOME HAS A GREAT VIEW OF THE POND WHERE YOU CAN WATCH THE WILDLIFE, ALSO SITUATED IN A CUL-DE-SAC STREET. HOME HAS EXTRA ROOM OFF MASTER BEDROOM, FOR A OFFICE OR CRAFT ROOM, ENCLOSED FRONT PORCH. SELLER HAS NEVER LIVED IN HOME AND IS SELLING HOME IN AS=IS, AS-SEEN CONDITION. HOME IS IN A VERY ACTIVE 55+ COMMUNITY WITH YEAR-ROUND HEATED POOL AND SHUFFLEBOARD. CLUBHOUSE IS HANDICAPPED MODIFIED. Sold as is. Measurements are approx. Buyer to verify all information that is deemed to be accurate.

3350 Courtney Drive, Holiday

Listing courtesy of CITY BREEZE ACTION REALTY. 813-394-4135

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