Holiday Homes with Sidewalk Exterior Features

Holiday Homes with Sidewalk Exterior Features

Welcome to Holiday, Florida—a charming gem nestled in Pasco County, where the sun shines bright and the community spirit is as warm as the weather! This delightful town offers a unique blend of suburban tranquility and vibrant local culture, making it an ideal place for families, retirees, and everyone in between.

Holiday is known for its beautiful neighborhoods, many of which feature homes with inviting sidewalk exterior designs. Imagine taking leisurely strolls along tree-lined streets, where friendly neighbors greet you with a smile and the sound of laughter fills the air. The sidewalks not only enhance the aesthetic appeal of the area but also promote an active lifestyle, encouraging residents to enjoy the outdoors and connect with one another.

The homes in Holiday are characterized by their diverse architectural styles, from cozy single-family houses to spacious modern residences, catering to a variety of tastes and budgets. Many properties boast well-maintained gardens and outdoor spaces, perfect for family gatherings or quiet evenings under the stars.

Living in Holiday means enjoying easy access to stunning Gulf Coast beaches, local parks, and recreational facilities, ensuring that there’s always something to do. The community is also conveniently located near shopping centers, dining options, and entertainment venues, making everyday life a breeze.

Whether you’re looking for your first home or a serene retirement retreat, Holiday, Florida, with its charming sidewalks and welcoming atmosphere, is the perfect place to call home. Come and discover the vibrant lifestyle that awaits you in this picturesque town!

Newest Holiday Homes with Sidewalk Exterior Features

1022 Bowsprit Lane Unit 1022, Holiday
$175,000
2 Beds ⋅ 2 Baths ⋅ TB8554815 MLS ⋅ 15 BLDG.
Great location with beautiful pond view from most windows, friendly surroundings, nature and tranquility. The open model perfect home with Vaulted ceilings is perfect for you, just move right in. Amazing updates include Quartz and Granite Countertops, recessed lighting, luxury vinyl floors along with newer ceramic tile and lace ceilings and newer Stainless Steel appliances. Sliders from both the Master Bedroom and Living room lead to Florida Room to relax and enjoy the views. The Master Bedroom has 2 large closets and Master Bath with dual sinks. Separate storage room and Reserved parking with plenty of guest spaces. Clubhouse with heated pool, shuffleboard and activities. The affordable HOA covers exterior maintenance, roof, lawn care, insurance, trash, cable TV, and internet, water/sewer and more, allowing you to truly enjoy worry-free living. Perfectly situated near some of the area’s best attractions, you’re just minutes from the white sandy beaches of the Gulf Coast, Anclote River Park, and the historic Tarpon Springs Sponge Docks, known for its Greek restaurants, local shops, and waterfront charm. Downtown Tarpon Springs offers year-round festivals, farmers markets, and cultural events, while nearby shopping centers, medical facilities, and golf courses ensure everythin you need is winin easy reach. No Flood Zone. Furniture negotiable. PRESENT ALL OFFERS!

1022 Bowsprit Lane Unit 1022, Holiday
3211 Southport Drive, Holiday
$179,900
2 Beds ⋅ 2 Baths ⋅ TB8554656 MLS
Great Waterview as you relax in the Florida room and watch Florida’s wildlife. Home features Newer Windows, Newer Luxury Vinyl Floorings, Walk in closets, Newer HVAC system with UV light, Carport that fits 2 average size cars and Enclosed Porch to enjoy Florida’s nature without being bugged too much. This lovely home is located in a Active 55+ community with Clubhouse, Year round Heated Pool, play Shuffleboard with other home owners, friends or family and low maintenance/HOA fees which includes trash pick up, grounds maintenance, Private Roads and common area taxes. Measurements are approx and information is deemed to be accurate and for the buyer verify.

3211 Southport Drive, Holiday
5111 Forum Boulevard, Holiday
$245,000
2 Beds ⋅ 3 Baths ⋅ TB8553806 MLS ⋅ N/A BLDG.
Short Sale. If you are looking for a great spot situated right between Tarpon Springs and Trinity, this beautifully maintained end-unit townhome is definitely worth a look. The two-bedroom, two-and-a-half-bath layout feels incredibly bright and open from the moment you walk in, thanks to the high ceilings and a ton of natural light. Downstairs, the open-concept living area flows right into a thoughtfully designed kitchen equipped with solid surface counters, stainless steel appliances, and generous cabinetry. You will find easy-care tile flooring across the main level, along with a convenient half bath, and you can step right outside to a private, fenced-in backyard and screened patio that makes an awesome spot for your morning coffee or winding down after a beach day. Enjoy a sneak peek of the lovely pond at the end of the backyard through the picket fence. Heading upstairs to the carpeted second floor, the landing area is actually wide enough to carve out a real workspace if you need a home office setup. The spacious primary suite gives you a great place to recharge, complete with a walk-in closet and a private ensuite bath. You will also find the washer and dryer conveniently located on this upper level, putting the laundry room exactly where you need it most. Adding to the everyday convenience is a roomy one-car garage that offers extra space for storage. It is all located in a pet-friendly community with low HOA fees, giving you quick and easy access to US-19, local shopping, great dining, and some of Florida’s most beautiful Gulf Coast beaches.

5111 Forum Boulevard, Holiday
5410 Flora Avenue, Holiday
$359,900
2 Beds ⋅ 2 Baths ⋅ TB8543370 MLS
Waterfront living with Gulf access in Holiday! This charming one-story concrete block home offers 2 bedrooms, 2 baths and 1,356 square feet of heated living space, ideally positioned on approximately 60 feet of frontage along the Anclote River. For boating and outdoor enthusiasts, the property features a new seawall, composite waterfront deck, dock with boat lift, and a separate floating dock perfect for jet skis, kayaks and paddle boards. The spacious screened-in lanai, finished with brick pavers, creates an inviting outdoor setting for relaxing, entertaining and taking in the ever-changing river views. Watch for dolphins, manatees and native birds, with beautiful sunsets providing an especially memorable backdrop. Inside, the home offers an updated kitchen with granite countertops, wood cabinetry and stainless-steel appliances, along with updated bathrooms and tile flooring throughout. A Florida room extends the living space, while a smaller screened lanai off the primary bedroom provides another peaceful spot to enjoy the outdoors. The roof was replaced in 2019. Conveniently located near Anclote River Park, Anclote Gulf Park, Key Vista Nature Park and Howard Park Beach, with easy access to Tarpon Springs, the historic Sponge Docks, shopping, restaurants and US-19. Whether you're looking for a full-time Florida residence, a second home or a waterfront retreat, this property offers an opportunity to enjoy the boating, fishing, nature and outdoor lifestyle that makes Florida waterfront living so appealing. Schedule your private showing today and experience the waterfront lifestyle for yourself.

5410 Flora Avenue, Holiday
4631 Eastwood Lane, Holiday
$224,900
3 Beds ⋅ 2 Baths ⋅ O6446246 MLS
Welcome to this charming three-bedroom, two-bathroom home located in the desirable Eastwood Acres neighborhood! Designed with a traditional floor plan, the home offers a functional flow throughout the main living spaces. The kitchen is tastefully updated with sleek countertops and all of the necessary appliances, making it a functional and attractive space for daily meals and entertaining. The primary suite features its own dedicated primary bathroom for added convenience. Outside, you will find a fully fenced-in backyard, perfect for outdoor relaxation, pets, or play. Conveniently located near shopping, dining, and major roadways, this home offers easy access to everyday essentials and routine commutes. Schedule your private showing today!

4631 Eastwood Lane, Holiday
1539 Plum Tree Road, Holiday
$239,900
3 Beds ⋅ 2 Baths ⋅ O6446257 MLS
This three-bedroom, two-bathroom home is situated in the desired Forest Hills neighborhood. Inside, the home features a light and bright open floor plan that creates a seamless flow through the main living space. The updated kitchen comes equipped with sleek stainless steel appliances and durable granite countertops, making it an inviting area for cooking and meal preparation. The primary bedroom includes an attached primary bathroom for added convenience and privacy. Step outside to enjoy the privacy of a fully fenced-in backyard, ideal for relaxing or outdoor activities. Located in the heart of Holiday, this home combines a peaceful residential setting with convenient access to shopping, dining, parks, and the beautiful Gulf Coast. Schedule your private showing today!

1539 Plum Tree Road, Holiday
4208 Canterberry Drive, Holiday
$215,000
2 Beds ⋅ 2 Baths ⋅ W7890004 MLS
No rear neighbors, no HOA, and not in a flood zone! This refreshed 2-bedroom, 1.5-bath Holiday home offers fresh interior paint, new light fixtures, new blinds on all windows, and easy-care tile throughout most of the home. Both bedrooms feature brand-new LVP flooring, while the bedrooms and main bathroom have new six-panel doors with stylish black hardware. The main bath also boasts a new vanity and puck lighting. The kitchen features refreshed cabinets with new hardware, new countertops, a deep, durable sink, and a gooseneck faucet. All appliances work, but the seller is offering a $2,000 credit toward new ones of your choice! The kitchen overlooks a spacious, separate family room with sliders opening to a large screened lanai, perfect for enjoying the fully fenced backyard and added privacy of no rear neighbors. The garage includes a washer and dryer, workbench, plus a half bathroom with an additional toilet and step-in shower. Roof replaced in 2018; A/C in 2014. Conveniently located near shopping, medical facilities, entertainment, and more. Schedule your private showing today!

4208 Canterberry Drive, Holiday
1419 Blue Marlin Boulevard, Holiday
$525,000
4 Beds ⋅ 3 Baths ⋅ TB8546084 MLS
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
2546 Arrowpointe Drive, Holiday
$425,000
4 Beds ⋅ 2 Baths ⋅ TB8553146 MLS
If you have been looking for a fully updated, move-in ready home in Holiday, Florida, this one-story, four-bedroom, two-bathroom beauty with a two-car garage in the gated Key Vista neighborhood is exactly what you need. One of the absolute best parts about this property is the location. You get to live incredibly close to the ocean and a wonderful nature park, while sitting safely outside of a flood zone for total peace of mind. So much of the heavy lifting has already been done for you here. The house features a newer roof, a brand new air conditioning unit, fresh paint, new gutters, a new storm door, and gorgeous luxury vinyl, bamboo, and tile floors throughout. As you step inside, the high ceilings really open up the space, making the layout feel bright, airy, and welcoming. The kitchen is completely remodeled, offering beautiful cabinets, crisp quartz countertops, an oversized island, and stainless steel appliances. It flows wonderfully into a formal, separate dining room that is ready for your next gathering. When it is time to unwind, the primary bedroom suite gives you a fantastic space with dual sinks, a garden tub, and a separate shower. Both bathrooms have been fully remodeled from top to bottom. Out back, you have a screened, covered patio that is perfect for enjoying the lovely weather year-round. Living in Key Vista means you get great community perks, including a clubhouse with a fitness center, tennis and volleyball courts, a heated pool and spa, and a playground. There are absolutely no CDD fees, and your monthly HOA fee is incredibly practical since it covers your cable TV, internet, gate access, and all those recreational facilities. To top it all off, you are just a short, easy drive from Howard Park, Sunset Beach, the Gulf of Mexico, Honeymoon Island State Park, and Caladesi Island. Come see it for yourself!

2546 Arrowpointe Drive, Holiday
3415 Monticello Street, Holiday
$220,000
2 Beds ⋅ 1 Baths ⋅ TB8550815 MLS
Move in and add your personality to this solid block 2 bedroom Holiday home west of US 19. Situated mid block on a quiet street close to everything a new homeowner needs. This home has been well maintained and features 2 generous bedrooms, one full bath, large family room, kitchen and dining room combo, and a flex room that can be utilized as office space, media room or possibly a guest bedroom. The home also features a 1 car garage with laundry area and fenced back yard. Conveniently located close to major highways 19 and 54, outdoor recreation, night life, shopping, restaurants and a short drive to world class beaches.

3415 Monticello Street, Holiday
5404 Front Drive, Holiday
$265,000
3 Beds ⋅ 2 Baths ⋅ TB8552102 MLS
Short Sale. A Short SALE that is a MUST SEE! Welcome to 5404 Front Dr in Holiday, FL, where space, style, and location come together on an oversized .21-acre lot with room to roam, expand, and even potentially add a pool. Best of all, there’s NO HOA or deed restrictions, giving you the freedom and flexibility today’s buyers dream of! Plus, this move-in-ready home is located in desirable Flood Zone X for added peace of mind. Inside, you’ll find approximately 1,422 sq ft with an additional BONUS SPACE under air, featuring 3 bedrooms plus a bonus 4th bedroom, 2 full bathrooms, and a garage conversion that offers extra living space—perfect for a primary suite, home office, or private guest retreat. The updated kitchen is sure to stop your scroll, showcasing refreshed cabinetry with new pulls, a stylish backsplash, sleek butcher-block countertops, a modern sink, stainless steel appliances, and durable LVP flooring—ideal for both everyday living and entertaining. The main bathroom is tastefully updated with beautiful new tile, classic subway tile, and updated fixtures, with no detail overlooked. The spacious enclosed Florida room (approximately 10x20) adds even more versatility and can easily serve as a family room, media room, playroom, or work-from-home space. According to the SELLER, the major UPDATES include ROOF: (2016), AC: (2019), and several WINDOWS have been replaced! Septic routinely maintained! All of this is in a prime location with quick access to US Highway 19 for easy commuting, just minutes from the sugary sand Gulf beaches and the Jolley Trolley, and a short drive to the charm of the historic Tarpon Springs Sponge Docks. Opportunities like this don’t last—act fast and make this incredible home yours today!

5404 Front Drive, Holiday
4149 Darlington Road, Holiday
$229,900
2 Beds ⋅ 2 Baths ⋅ TB8550934 MLS
Welcome home to this beautifully updated 2-bedroom, 2-bath home in Tahitian Homes with NO HOA! An inviting covered front porch opens to a bright interior featuring wood-look tile flooring, contemporary lighting, and a flowing layout for comfortable living and entertaining. The kitchen showcases crisp white cabinetry, stone countertops, a tile backsplash, and stainless steel appliances. Generously sized bedrooms and tastefully updated bathrooms complete the home’s welcoming feel. Step outside to a spacious backyard with a fenced area and room for outdoor dining, gardening, or simply enjoying the Florida sunshine. Conveniently located near shopping, dining, and US-19, this home also puts coastal recreation within easy reach. Enjoy boating at Anclote River Park, explore the shops and waterfront restaurants at Tarpon Springs’ historic Sponge Docks, or unwind on the beach at Fred Howard Park. Schedule your private showing and discover everything this home has to offer!

4149 Darlington Road, Holiday
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