Holiday Real Estate Search

Holiday Properties for Sale

Our website features the best Holiday real estate search for homes, condo, land and foreclosure properties available. It is the only site you will ever need! It is easy-to-use and updated by the official REALTOR®’s database every 15 minutes. 

You can save searches, and get daily email alerts of new listings, price changes, sold data, and market reports. Our Interactive Map Search allows you to view properties on a map or refine your search by drawing the boundaries around the area you desire.

Curious about what’s happening in the Holiday real estate market? Sign up for a  Holiday Real Estate Market Report to see what’s active, under contract, and sold!

Newest Holiday Properties for Sale

$235,000
3 Beds 2 Baths Crest Ridge Gardens SubDv. 34690 Zip Code
Step into a piece of Florida charm at 1617 Derrick Street, Holiday, FL. This lovingly maintained 3-bedroom, 2-bath home with a 1-car carport sits on an expansive corner lot and offers a rare opportunity to own a home that has been beautifully preserved while showcasing the character and craftsmanship of its original 1967 construction. From the moment you enter, you'll appreciate the stunning terrazzo floors that flow throughout much of the home, providing timeless style and durability. The original kitchen and bathrooms have been exceptionally cared for and remain in excellent condition, offering the kind of authentic mid-century character that is becoming increasingly difficult to find. For buyers who appreciate nostalgic details and vintage charm, this home is a true gem. Outside, classic metal awnings provide both character and practical storm protection, while the generous corner lot offers plenty of space for gardening, entertaining, or simply enjoying the Florida sunshine. 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. Enjoy nearby beaches, waterfront parks, boating, fishing, and some of Florida's most spectacular sunsets, all just a short drive away. If you've been searching for a home with authentic character, exceptional upkeep, and a location that embraces the laid-back Florida lifestyle, 1617 Derrick Street is ready to welcome you home.

1617 Derrick Street, Holiday

$210,000
2 Beds 1 Baths Tahitian Dev Sub SubDv. 34691 Zip Code
PROPERTY HIGHLIGHTS • Situated at approximately 14 feet elevation — home and street have NEVER FLOODED, including during the major hurricanes of 2024 • LARGE CORNER LOT WITH NO HOA • Fully fenced backyard featuring double gate access, allowing convenient boat or trailer storage/access • Ideally positioned near waterfront parks, Gulf Coast recreation, local restaurants, and outdoor activities • Approximately 10 minutes to both Downtown Tarpon Springs and Downtown New Port Richey • Less than 10 minutes from Key Vista Nature Park, offering scenic Gulf views, walking and biking trails, hiking paths, and kayak launch access • Approximately 20 minutes from Downtown Dunedin • Convenient access to shopping, dining, entertainment, nightlife, and locally owned coffee shops INTERIOR & EXTERIOR UPDATES • New front entry door • Fresh interior and exterior paint • Updated modern fixtures throughout the home • Brand new kitchen appliances installed December 2025 • New washing machine installed in 2026 • Solid surface countertops installed November 2021 • Bathroom remodeled in 2021 MAJOR SYSTEM IMPROVEMENTS • Complete HVAC system replacement completed October 2021, including condenser, air handler, ductwork, vents, and associated components • Water heater replaced in 2025 • Roof equipped with hurricane clips, providing additional structural reinforcement between the roof system and exterior masonry walls • Full set of hurricane shutters included for all windows ADDITIONAL FEATURES • Monitored ADT security system • Keyless front door entry EXCLUSIONS • Dining room chandelier and kitchen island does not convey and will be removed prior to closing unless otherwise negotiated.

3547 Wilson Drive, Holiday

$305,000
3 Beds 3 Baths Holiday Lake Estates SubDv. 34691 Zip Code
Turn-Key 3 bedroom home with Dual Primary Suites-Ideal for Multi-Generational Living or Income Potential! Welcome to this spacious 3bedroom, 3 bathroom home located in the established Holiday Lake Estates community. Offering 1,667 sqft of living space, this home features a flexible split-bedroom floor plan with two primary suites, making it perfect for multi-generational living, guests, or potential rental income. The interior showcases an open layout with tile flooring, solid wood cabinetry, and a beautifully updated kitchen featuring granite countertops, stainless steel applicances, and a custom backsplash. An eat-in kitchen area provides additional dining space and is ideal for everyday living. Major updates include updated electricial system, tankless water heater, and newer central AC, providing peace of mind for years to come. Situated on a fenced lot with a 1-car attached garage, this property offers both privacy and functionality. With no HOA restrictions, homeowners have added flexibility for personal use or investment. Conveniently located near schools, parks, shopping, dining, and Gulf beaches, this property combines comfort, value, and versatility. Whether you're looking for a primary residence, multi-generational home, or income-producing opportunity, this property checks all the boxes. All information pertaining to the property is deemed reliable, but not guaranteed. Information to be verified by the Buyer. Be advised that cameras may exist recording audio and video inside/outside the property, such as ring doorbells. Photos are digitally enhanced and could be altered, please verify.

1050 Deal Lane, Holiday

$199,999
2 Beds 2 Baths Beacon Square SubDv. 34691 Zip Code
Charming 2-Bedroom, 2-Bath Home on a Spacious Corner Lot, never been flooded!! Move-in ready and available immediately! This well-maintained 2-bedroom, 2-bath home offers comfort, convenience, and plenty of space both inside and out. Step inside to discover two spacious living areas, providing flexible options for entertaining, relaxing, or creating a home office. The freshly painted interior gives the home a bright, clean feel, while the kitchen features new appliances, ample cabinet space, and a convenient pantry closet, making meal preparation a pleasure. Situated on a large corner lot, the property boasts a fully fenced backyard perfect for pets, outdoor gatherings, and weekend barbecues. Enjoy Florida's beautiful weather year-round from the inviting covered back porch. Additional features include: 2 spacious bedrooms and 2 full bathrooms Oversized one-car garage Washer and dryer hookups located in the garage Fresh interior paint throughout New kitchen appliances Large fenced backyard Corner lot with added privacy and curb appeal Covered rear porch for outdoor enjoyment Ideally located near beautiful Gulf beaches, airports, shopping, dining, and local amenities, this home is an excellent opportunity for first-time homebuyers, seasonal residents, or investors looking to add a quality property to their portfolio. Don't miss your chance to own this charming Florida home—schedule your showing today!

3452 Columbus Drive, Holiday

$239,999
3 Beds 3 Baths Anclote Square SubDv. 34691 Zip Code
Short Sale. Skip the projects, skip the surprises, and step into a home that already feels dialed-in. Built in 2023, this 3-bedroom townhome delivers that crisp, like-new vibe—without the builder waitlist or the premium price tag. The main level has an easy, open flow from the living area into a kitchen designed for real everyday use. This one upgrades the standard package with stainless steel appliances, a granite countertop, and a clean, neutral backsplash that ties everything together. Your enclosed patio sits just off the living room, giving you a private spot for morning coffee or unwinding after work, all without the upkeep of a yard. Upstairs, the layout keeps life simple and functional. The primary suite has its own private bath, while the two additional bedrooms flex perfectly for guests, a roommate, or a dedicated office. And with blonde laminate flooring throughout the second floor—no carpet anywhere—the space feels bright, modern, and easy to maintain. Laundry is right where it should be: upstairs near the bedrooms. Your monthly overhead stays low thanks to NO CDD fee, and the HOA covers exterior maintenance, high-speed internet, and cable. A 1-car garage and metal storm shutters check off the practical boxes. The location puts you in the sweet spot between convenience and coastal living. You’re minutes from grocery stores, retail, medical facilities, and US-19 for an easy commute. And when you want to get out and enjoy the area, you’re right near the Pinellas County line—close to the Tarpon Springs Sponge Docks, Anclote River Park, boat launches, waterfront dining, and scenic trails. Clean, modern, low-maintenance, and move-in ready—this is the kind of home that gives you your weekends back.

3083 Victoria Inlet Drive, Holiday

$239,999
3 Beds 3 Baths Anclote Square SubDv. 34691 Zip Code
Virtually Staged. Short Sale. Forget the endless weekend honey-do lists and the hidden costs of an older home. Built in 2023, this 3-bedroom townhome gives you that clean, brand-new feel without the builder’s waitlist. The main floor is wide open, flowing from the living room right into a kitchen that actually has room to move. The owners upgraded the kitchen past the builder-grade standard by adding a custom tile backsplash that pairs with the neutral white quartz counters and breakfast bar. Just past the living area, you can step out onto your enclosed patio space—perfect for morning coffee or unwinding in the evening with the rare perk of having zero backyard neighbors directly behind you. Upstairs keeps life practical: the primary suite features its own private bath, while the other two bedrooms work perfectly for guests, roommates, or a dedicated home office. Plus, the laundry closet is upstairs right where the clothes actually are. Your monthly overhead is incredibly lean here. There is NO CDD fee, and the low HOA covers your exterior maintenance, high-speed internet, and cable TV package right out of the gate. Metal storm shutters and a 1-car garage are already checked off the list for you. Location-wise, you are right in the sweet spot for everyday convenience and weekend fun. For daily needs, you’re just minutes from major grocery chains, retail shopping, medical facilities, and US-19 for an easy commute. When you want to head out, you're a stone's throw from the Pinellas County line, putting the historic Tarpon Springs Sponge Docks, Anclote River Park boat launches, coastal trails, and local waterfront dining practically in your backyard. Clean, modern, private, and zero yard work to eat up your weekends.

3048 Victoria Inlet Drive, Holiday

$380,000
2 Beds 2 Baths Shadow Oaks Sub SubDv. 34690 Zip Code
Poolside Living Meets Prime Location! This beautifully maintained pool home offers a desirable split-bedroom floor plan, giving the primary suite added privacy from the secondary bedrooms. Step inside to discover a gorgeous, updated kitchen remodeled in 2021, featuring modern finishes, electrical outlets conveniently installed within the cabinetry, and Alexa-controlled under-cabinet lighting for added style and functionality. The spacious primary suite provides a private retreat, while the open living areas flow seamlessly to the outdoor oasis. Enjoy Florida living year-round with a screened-in lanai, covered patio, and sparkling pool—perfect for entertaining guests or relaxing after a long day. This home has been thoughtfully updated with numerous improvements, including updated electrical, a brand-new garage door, epoxy-coated garage floors, and a water heater installed in March 2022. Roof 2012 Outside, you’ll find a storage shed for additional space and new fencing with double gates, offering convenient access for boats, trailers, or recreational vehicles. Ideally located just 10 minutes from downtown Tarpon Springs and 15 minutes from downtown New Port Richey, you’ll enjoy easy access to charming waterfront dining, shopping, festivals, and local entertainment. You’re also only minutes from Fred Howard Park and Beach, one of the area’s most beloved coastal destinations. Plus, Clearwater-St. Pete Airport and Tampa International Airport are both within approximately 45 minutes, making travel a breeze while keeping you close to all the area’s popular downtowns, restaurants, and local hotspots. Don’t miss this opportunity to own a move-in-ready pool home in an unbeatable location that combines comfort, convenience, and the best of Florida living.

3110 Shadow Oaks Drive, Holiday

$235,000
2 Beds 2 Baths Aloha Gardens SubDv. 34691 Zip Code
BRAND NEW AC - June 2026! Newer roof 2022! Welcome to this beautifully maintained 2-bedroom, 2-bathroom home in Holiday where thoughtful updates and a functional layout create the perfect blend of comfort and convenience. With a freshly painted exterior and front door and a 2020 water heater, this move-in-ready home offers both curb appeal and peace of mind. Step inside to a bright and inviting front living room filled with natural light, complemented by ceiling fans throughout the home for year-round comfort. The open floor plan flows seamlessly into the spacious kitchen featuring stainless steel appliances, abundant cabinetry, and a separate pantry for extra storage. The kitchen overlooks both the dining area and cozy family room, creating an ideal setup for entertaining guests or enjoying everyday living. The primary suite offers a walk-in closet and a private en suite bathroom with fresh paint, while the secondary bedroom provides flexible space for guests, a home office, or hobbies. Sliding glass doors from the dining area open to a covered and screened-in porch, the perfect spot to relax and enjoy Florida’s beautiful weather in comfort. Outside, the backyard has been transformed with all concrete removed and replaced with fresh sod, creating a lush outdoor space with endless possibilities for entertaining, pets, gardening, or simply enjoying the outdoors. The fully fenced yard adds privacy and functionality, while the newly refreshed landscaping enhances the home’s inviting feel. Additional highlights include a freshly painted garage and garage floor, adding to the home’s clean and updated appearance. Conveniently located in a quiet neighborhood near shopping, dining, parks, and everyday amenities, this charming Holiday home is ready for its next owner to move right in and enjoy. Schedule your showing today!

3510 Allandale Drive, Holiday

$225,000
3 Beds 2 Baths Holiday Lake Estates SubDv. 34691 Zip Code
Welcome to this beautifully maintained concrete block stucco home offering 3 bedrooms, 2 bathrooms, and an inviting open floor plan designed for comfortable everyday living and entertaining! From the moment you step inside, you’ll appreciate the spacious layout and durable 18” ceramic tile flooring flowing throughout the entire home for easy maintenance and a clean modern feel. The kitchen features real wood white shaker cabinets, white appliances, a double stainless steel sink, and a custom tiled backsplash that adds the perfect touch of style and character. Ceiling fans throughout the home help keep things comfortable year-round. One of the standout features of this property is the incredible energy-saving package that comes fully included in the purchase price! The home is equipped with a fully paid 5-year-old solar system along with two Tesla Powerwall backup battery packs, providing efficiency, energy savings, and peace of mind for the new owner. The electrical panel was also updated just 5 years ago to support the system. Step outside and enjoy the large screened rear patio complete with its own dedicated A/C unit, creating the perfect space to relax or entertain regardless of the season. The fenced backyard offers privacy and functionality while the two separate tool sheds provide plenty of additional storage space for tools, hobbies, or outdoor equipment. Additional updates include a 4-year-old HVAC system, 8-year-old roof, and 8-year-old hot water heater. The property also features a 1-car garage and an additional covered 1-car carport for extra parking convenience. Conveniently located close to fantastic restaurants, shopping, and everyday amenities, this move-in ready home combines comfort, efficiency, and value all in one incredible package. Schedule your private showing today before this one is gone!

3415 Coldwell Drive, Holiday

$425,000
4 Beds 3 Baths Gulfwinds SubDv. 34691 Zip Code
Welcome to your turnkey coastal retreat in the highly desirable Gulfwinds community, where homes rarely become available and the Florida lifestyle takes center stage. This spacious 4-bedroom, 3-bath home offers over 2,600 square feet of living space with a bright open layout, soaring ceilings, and a functional split-bedroom floorplan designed for both everyday living and entertaining. Located in an X flood zone where flood insurance is typically not required, this move-in ready home combines peace of mind with comfort and convenience. Inside, you'll find an open-concept living area, solid wood cabinetry, solid surface countertops, walk-in closets, and a spacious kitchen that flows seamlessly into the main living spaces. The home also features a 3-car garage, hurricane shutters, irrigation system, indoor laundry room, and comes turnkey furnished for an easy move right in experience. Perfectly positioned just minutes from historic downtown Tarpon Springs and the famous Sponge Docks along the Anclote River, this location offers the ideal blend of laid-back coastal charm and everyday convenience. Enjoy quick access to local restaurants, boating, waterfront parks, golf cart rides through the neighborhood, nearby Gulf beaches, and the scenic Coastal Anclote Trail connecting you to parks, nature, and downtown Tarpon Springs. Local schools are also just a short walk away, making this an ideal setting for full-time residents, seasonal owners, or anyone looking to enjoy the best of Florida living. Whether you're looking for more space, a low-maintenance Florida home, or a peaceful coastal community close to it all, this property delivers. Schedule your private showing today!

1316 Blue Marlin Boulevard, Holiday

$250,000
2 Beds 1 Baths Holiday Lakes West SubDv. 34691 Zip Code
Available to homeowners as well as investors! New to the market is an adorable and well maintained 2 bedroom, 1 bath home with an attached garage in Holiday Lakes West. Seller will have a new roof installed with an acceptable offer. And A/C system is from 2021. Sunroom has been drywalled in and adds additional living square footage. Recent upgrades include a new SS refrigerator, new laminate flooring, new carpet, and fresh interior and exterior paint with interior doors replaced as well. Spacious back yard to host family and friend gatherings, enjoy your hobbies, gardening, or let your furbabies enjoy the outdoors. This home would make an ideal cozy and comfortable year round residence for the next chapter of your life, but it could also serve as a wonderful seasonal getaway. And investors, yes, you can utilize this as an immediate investment property with no HOA restrictions. Nor are there any CDD fees! Property is in "X500" flood zone and seller has never experienced any flooding issues. Utility companies are Duke for electric and PCU for water. There is no shortage of shopping, dining, cultural events, outdoor activities, golf venues, amusement parks, sports arenas, beaches and scenic parks, boating options, the Pinellas Trail and more! Proximity to two international airports, Tampa, Clearwater and St. Pete, as well as Lake Tarpon and the famous Tarpon Springs Sponge Docks. Allow yourself to fall in love with the coastal, laidback lifestyle of Florida living. Call to schedule your private showing today! All information contained herein is deemed accurate, including leasing restrictions and approximate room measurements, but should be verified by buyer and buyer's agent. NO SIGHT UNSEEN OFFERS WILL BE CONSIDERED.

1238 Fuchsia Drive, Holiday

$340,000
3 Beds 2 Baths Gulfwinds SubDv. 34691 Zip Code
2201 Parrot Fish Drive, Holiday, FL Gulfwinds Villa | 3 Bed + Den/Office | 2 Bath | 2-Car Garage | 1,876 Sq Ft | Maintenance-Free Living | NOT in a flood zone Built in 2013, this beautifully designed one-story villa lives like a single-family home - without single-family maintenance headaches. Tucked away on a private cul-de-sac, this 1,876-square-foot home features soaring ceilings and an open-concept kitchen, dining, and family room that creates an airy, spacious feel. The oversized granite island is perfect for entertaining, while the kitchen also features 42-inch wood cabinets with pull-out shelves, stainless steel appliances, an undermount sink, a closet pantry, and large neutral ceramic tile throughout. Every space is designed to be both functional and stylish. The private primary suite is thoughtfully designed with a large walk-in closet and a spa-like en suite bathroom featuring dual granite vanities, an oval soaking tub, walk-in shower, and private water closet. Bedrooms two and three are located on the opposite side of the home with a second full bathroom, offering ideal separation for guests, family, or hobbies. The den, complete with French doors, provides flexible space perfect for a dedicated home office or additional sitting area. An interior laundry room with full-size appliances, utility sink, cabinetry, and extra storage adds even more convenience. Step outside to the screened lanai with double doors and enjoy true indoor-outdoor Florida living. With no rear neighbors, privacy landscaping, and ample space to relax, the backyard feels like a private retreat. The lanai is also hot tub-ready with a dedicated 240-volt hookup. The fully fenced yard includes beautiful landscaping on a programable irrigation system, a stone paver patio, raised garden bed, and dedicated grilling area. Additional features include a spacious 2-car garage with built-in workbench, attic storage with ladder access, and plenty of room for organization. A whole-home water softener system enhances daily comfort while adding to the home's thoughtful upgrades and functionality Low HOA fees cover lawn service, internet, cable, exterior maintenance, roof replacement, and more. The community pool is just around the corner, making year-round relaxation effortless. This truly is maintenance-free living at its best. Gulfwinds is ideally located close to schools, marinas, fishing piers, shopping, golf, dog parks, splash parks, and the natural beauty of Florida's Gulf Coast. Nearby attractions include Anclote River Park, Anclote Gulf Park, and Tarpon Springs Sponge Docks with its famous Greek restaurants, shops, and cultural events. A new walking and biking trail system conveniently connects the community to nearby parks and the Pinellas Trail. Private cul-de-sac location. Smart floor plan. Low maintenance. Exceptional location.

2201 Parrot Fish Drive, Holiday

$300,000
3 Beds 2 Baths Holiday Lake Estates 21 SubDv. 34691 Zip Code
JUST REDUCED TO 300K AND SELLER TO CONTRIBUTE ANOTHER 5K INCENTIVE TO THE BUYER!!! NO HOA!!! Welcome to your Holiday home retreat! Nestled against a conservation-lot along the canal, you'll enjoy peaceful nature views and abundant wildlife right from your backyard while enjoying the privacy of no rear neighbors, a true rarity at this price point. This beautifully maintained 3-bedroom, 2-bath, 1-car garage + extra wide driveway, screened lanai, and fully fenced home offers 1,462 square feet of comfortable Florida living. Inside, you'll find a bright, functional floor plan with a living room and dining area, a versatile family room or office space, and three generously sized bedrooms with two full baths. Step outside to your own secluded oasis featuring an inground pool enclosed by a screened lanai — ideal for year-round entertaining, weekend cookouts, or simply relaxing in the Florida sunshine in total comfort. Major-ticket items are already taken care of: new impact windows and sliding glass door installed in 2025. Roof, HVAC and pool pump 2016, plus a brand-new 2026 water heater - move in with confidence and skip the costly upgrades. Best of all - NO HOA and NO CDD fees! Access the Coastal Anclote Trail right from the neighborhood and bike to the Anclote River Boat Ramp and fishing pier or connect to the Pinellas Trail in Tarpon. Just a short drive to Fred Howard Park, white-sand beaches, and the scenic causeway. You're also minutes from historic Tarpon Springs Sponge Docks, fantastic Greek dining, shopping, golf, and all the charm the Nature Coast has to offer. Homes like this — with a pool, conservation lot, no HOA, — don't come along often. Schedule your private showing today before it's gone!

1853 Dartmouth Drive, Holiday

Start Your Search