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Single Family Homes for Sale in Holiday, FL

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Welcome to your dedicated resource for single family homes for sale in Holiday, FL. This page is your live portal for listings that match the exact homes for sale you demand, filtering out irrelevant properties to save you time. As local Holiday, FL agents, Joseph Sullivan Real Estate specializes in the unique market dynamics of this area, offering insights into amenities, home values, and investment potential. Start exploring the single family properties currently available below, or contact a local agent to discuss the details that matters most to your search.

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All Single Family Homes for Sale in Holiday, FL

$299,000
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
$359,900
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
$199,000
2 Beds ⋅ 1 Baths ⋅ Orangewood Village SubDv.
Welcome to 4718 Trafford Rd. Fresh interior and exterior paint give the home an updated feel throughout. The kitchen features stainless steel appliances and an accent backsplash. Out back, a fully fenced yard and covered patio extend the living space for dining or relaxing in the shade. Included 100-Day Home Warranty with buyer activation

4718 Trafford Road, Holiday
$320,000
3 Beds ⋅ 3 Baths ⋅ Colonial Oaks SubDv.
This beautifully maintained 3-bedroom, 2-bathroom home is located in a peaceful, NO-HOA neighborhood—making it a perfect place to call home! Tucked on a quiet street with a corner lot, this residence offers the perfect balance of comfort and everyday functionality. Inside, vaulted ceilings enhance the sense of space and natural light throughout the home, creating an inviting atmosphere from the moment you enter. The primary suite provides a relaxing retreat with a generous walk-in closet and a spacious suite bathroom complete with a garden tub and separate shower. Two additional spacious bedrooms feature parquet flooring with vaulted ceilings as well. The attached two-car garage has been upgraded with a sleek, freshly applied epoxy coating—ideal for a clean, durable workspace or simply keeping your vehicles in style. Located just minutes from local favorites like Anclote River Park, Fred Howard Park Beach, the famous Tarpon Springs Sponge Docks, and Seven Springs Golf & Country Club, this home puts you close to the best of the Gulf Coast lifestyle. Don’t miss this exceptional investment opportunity—schedule your private tour today!

5116 Plantation Drive, Holiday
$379,000
3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv.
Welcome to 1346 Chancellor Dr, a charming house that invites you to explore its unique character and potential.Direct canal access to the gulf, New Roof .Nestled in a desirable location, this property accords a wonderful opportunity for those seeking a place to call home. With its classic architectural design, the exterior exudes curb appeal, while the interior awaits your personal touch. Whether you're looking to relax in a cozy living space or entertain guests, this house provides a versatile layout to suit your needs. The surrounding area accords a peaceful atmosphere, appropriate for enjoying outdoor activities and leisurely strolls. Don't miss the chance to make this house your own and create lasting memories in a welcoming community.

1346 Chancellor Drive, Holiday
$250,000
3 Beds ⋅ 2 Baths ⋅ La Villa Gardens SubDv.
Your search ends here! This stunning three-bedroom, two-bathroom home boasts over 1500 square feet of living space. Enjoy the spacious screened front porch, triple-wide driveway, and fenced yard. The kitchen features cherry wood cabinets and beautiful Corian countertops. It opens up to a breakfast bar that seamlessly connects to the family room. The master suite is a luxurious retreat, complete with a newer countertop, sinks, fixtures, exhaust fan, updated vanity, and a walk-in shower. Both bathrooms have new lights and interior paint. The entire home is adorned with new closet doors, and a newer 6-foot vinyl fence. Step onto the front screened lanai, which is equipped with new outlets, and relax by the pool. The open back patio offers additional outdoor living space. The home is conveniently located near shopping and restaurants, with easy access to the library and Anclote Elementary School. Just a 2.5-mile drive away is Starkey Wilderness Park, and you can reach Suncoast Parkway in 17 minutes. Popular Tarpon Springs is a 12-minute drive, while Beach Fred Howard Park is 19 minutes away. For those traveling to Tampa International Airport, the home is a 30-minute drive away. The roof is from 2012, and the HVAC system was updated in 2021. Note: The previous contract was canceled, and neither the property nor the seller was at fault.

5646 Andrea Drive, Holiday
$255,000
2 Beds ⋅ 2 Baths ⋅ Tahitian Dev Sub SubDv.
WELCOME TO WATERFRONT FLORIDA LIVING! This 2-bedroom, 2-bath POOL HOME offers picturesque water views, a PRIVATE DOCK, screened-in pool and lanai, and NO HOA. Situated along a wide lagoon of Lake Conley, this property is ideal for boating, fishing, kayaking, or simply relaxing and enjoying the peaceful waterfront setting. Step inside to a bright and inviting floor plan filled with natural light. The spacious living and dining areas flow into the kitchen and out to the screened pool and lanai, creating an ideal layout for indoor-outdoor living and entertaining. Both bedrooms are generously sized, and both full bathrooms have been updated. The outdoor living space is the true highlight. Enjoy the screened-in pool overlooking Lake Conley, with plenty of room for lounging, dining, and entertaining year-round. Beyond the pool, the backyard leads to your private custom dock, giving you direct access to the water from your own property. Launch a kayak, head out on the water, fish from the dock, or enjoy your morning coffee while taking in the peaceful waterfront views. This home also features an oversized 412 sq. ft. 1-car garage, double-pane windows, NEW A/C in 2025, washer and dryer, water heater approximately 4 years old, dishwasher and disposal approximately 3 years old, and pool pump approximately 2 years old. The home did NOT FLOOD in the recent hurricanes and offers an excellent opportunity as a full-time residence, vacation retreat, or investment property. With NO HOA OR CDD, you can enjoy waterfront living without the added community fees. Conveniently located in Holiday near Tarpon Springs and the Sponge Docks, Gulf beaches, parks, shopping, dining, medical facilities, and Tampa International Airport. Schedule your private showing today!

1954 Coolidge Road, Holiday
$239,900
2 Beds ⋅ 2 Baths ⋅ Aloha Gardens SubDv.
Virtually Staged. INVESTMENT OPPORTUNITY OR FIRST-TIME HOMEOWNER OPPORTUNITY IN A OPORTUNE LOCATON! Minutes from Pinellas County and Tarpon Spring BEACHES! This charming 2-bedroom, 1.5-bathroom Lake Conley home offers an exciting opportunity to create the waterfront home you’ve been dreaming of or add a promising property to your investment portfolio. With a brand-new kitchen, updated windows, a 2019 A/C unit, roof replaced approximately four years ago, and a spacious 1.5-car garage, several of the major updates are already in place—leaving you the opportunity to add your own personal touches and build equity. Situated directly on beautiful Lake Conley, this property offers tranquil water views and a desirable waterfront lifestyle. The versatile layout features an A/C-cooled Florida room flowing into an additional uncooled sunroom overlooking the lake, creating flexible space for relaxing, entertaining, a home office, or simply enjoying the peaceful surroundings. Step outside to discover a back lanai and checkered-style paver patio overlooking the water—perfect for morning coffee, afternoon relaxation, or entertaining while taking in the lake views. Whether you're a first-time buyer looking for an affordable way to enter the market and customize a home to your taste, a buyer seeking a waterfront property with room to add value, or an investor searching for your next opportunity, this Lake Conley property offers LOCATION, WATERFRONT LIVING, AND POTENTIAL! Bring your vision and make this home your own!

3852 Sunray Drive, Holiday
$230,000
3 Beds ⋅ 1 Baths ⋅ Holiday Lake Estates SubDv.
Welcome to 1031 Conoley Ln, a beautifully maintained and thoughtfully updated 3-bedroom, 1-bath home in the desirable Holiday Lake Estates community of Holiday, Florida! Offering 1,004 square feet of comfortable living space on a spacious 5,663-square-foot lot, this home delivers an ideal combination of updates, functionality, and Florida living. From the moment you arrive, the pride of ownership is evident with attractive landscaping and well-maintained exterior. Inside, the home features a bright and functional layout with tile and vinyl flooring throughout the home. The updated kitchen offers wood cabinetry and a stainless-steel refrigerator, while the remodeled bathroom features updated fixtures, tile, and a modern vanity. The bedrooms provide comfortable living space with durable vinyl flooring, making this home both stylish and practical. Numerous major improvements provide valuable peace of mind. Outside, the backyard is designed for both enjoyment and convenience, featuring a patio, fire pit, and two storage sheds offering plenty of room for tools, hobbies, lawn equipment, bikes, and more. The attached garage adds even more storage and everyday convenience. Important ages include Roof 2013, Water Heater 2018, Electric panel 2018, AC 2018 and Water Softener 2018. Located in an established residential neighborhood, this home puts you close to shopping, restaurants, schools, parks, nature trails, dog parks, and some of the area's beautiful Gulf Coast beaches. Whether you're searching for a comfortable primary residence, a Florida getaway, or an investment opportunity, this property offers an incredible combination of location, updates, outdoor space, and value. With its move-in-ready condition, versatile 3-bedroom floor plan, and extensive list of improvements, 1031 Conoley Ln is a property you will want to see in person. Schedule your showing today

1031 Conoley Lane, Holiday
$550,000
4 Beds ⋅ 3 Baths ⋅ Gulfwinds SubDv.
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
$175,000
2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.
Your Florida opportunity is here! This 2-bedroom, 2-bath home in desirable Beacon Square in Holiday offers the perfect blank canvas for you to make it your own. Featuring durable terrazzo flooring throughout and an enclosed lanai that provides additional flexible living space, this home has plenty of potential for both homeowners and investors. The additional den/bonus room gives you even more versatility—use it as a home office, hobby room, guest space, or whatever fits your lifestyle. With a little vision and some personal touches, this home could truly shine. Located in Holiday, you're conveniently close to the Gulf, beaches, shopping, restaurants, parks, and everyday conveniences, making it easy to enjoy the Florida lifestyle without being far from everything you need. Whether you're searching for your first home, a winter getaway, or an income-producing investment, this property is ready for its next chapter. Bring your ideas and make this one yours!

3519 Brookston Drive, Holiday
$205,000
2 Beds ⋅ 1 Baths ⋅ Lullaby Gardens Add SubDv.
Come check out this great property located in Holiday Florida. This home offers 2 bedrooms, 1 full bathroom, 2 family rooms, kitchen and laundry inside. The interior features tile flooring throughout, window coverings, and appliances included with washer/dryer. The bathroom has an upgraded sit in whirlpool style bathtub. On the exterior you'll find a 2-car covered carport, a front screened in porch, an extra RV style parking structure, and covered patio and fenced in backyard. Additionally, the home has a tankless water heater, AC unit 2 years new, water conditioner, roof within the last 10 years, hurricane panels, and generator for backup power. This home's lot is situated the end of the street, with a greenbelt adjacent. An easy starter home or investor potential, see for yourself!

1650 Aqua Lane, Holiday
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