Holiday Homes For Sale & Real Estate - 328 homes

Remarks: Big Price Reduction!! Great deal waiting for you in the gated, 55+ community of Lake Conley, in Holiday, Florida. You own the land here and have low +/- $70 a month HOA dues, no land lease. This is a 1,152 square foot 2-bedroom, 2 bath home. This pet-friendly park will allow with one dog, or one cat, no more than 25lbs. Service animals and Emotional Support animals require current documentation. No aggressive breeds. The home has a 2 carport, screened porch, storm shutters, shed with laundry and sink, a newer water heater, ceiling fans and comes furnished. The dining room has a built-in hutch, with a mostly original kitchen, but has a newer stainless-steel dishwasher and tiled backsplash. There is a family room and a somewhat updated hall bath, with tiled tub/shower surround and new hardware. It also has a newer sink and toilet, with the main bath having a walk-in shower. The homes floors do have significant soft spots in several areas and will likely need some sub-floor replacement. There’s a boat ramp and fishing pier here for residents to use, as well as a rentable additional boat/RV parking lot/storage area. The community pool and clubhouse are all here to be enjoyed by the residents. Golf carts and motorcycles welcome. Very private and peacefully tucked in off US 19 but yet so close to everything. It’s an easy drive to some of Florida most beautiful beaches, parks, restaurants and shopping. Also, with easy commute to Tarpon Springs. Community offers a heated pool all year round, active clubhouse with year around events, shuffleboard, boat ramp, fishing pier and much more. Call for a showing today.

Listing is courtesy of: SELECT REAL ESTATE OF PINELLAS (727-584-3588)

Listing Agent: Vint Hughes (727-420-0770)

Remarks: Welcome to this 2-bedroom,1-bath home located in the heart of Holiday! This well-maintained residence offers approximately 1,004 sq. ft. of living space with a functional floor plan designed for comfortable everyday living. The home features a bright living area filled with natural light, a practical kitchen and generously sized bedrooms. Ceramic tile throughout for easy maintenance. Enjoy the spacious backyard-perfect for entertaining, pets or future outdoor upgrades. Conveniently located near shopping, dining, parks and just a short drive to Gulf Coast beaches. Easy access to Pinellas County! Don't miss this affordable opportunity to own a piece of Florida living!

Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-835-3110)

Listing Agent: Sheree Landreth (727-919-3713)

Remarks: Owner financing! Welcome to 3215 Bright Dr. in Holiday, a solid home offering comfort, privacy, and endless potential in a convenient location close to everything the Gulf Coast has to offer. Nestled in a quiet neighborhood, this property features spacious living areas filled with natural light, a functional layout perfect for everyday living and entertaining, and a generously sized yard ideal for relaxing or creating your own outdoor oasis. Whether you’re a first-time homebuyer, seasonal resident, or investor, this home presents an incredible opportunity with easy access to beaches, shopping, dining, parks, and major roadways. Seller is offering owner financing with only 10% down, 5.5% interest, and affordable monthly payments of approximately $1,280, creating a rare opportunity for buyers seeking flexible financing options. Enjoy the perfect blend of Florida lifestyle, value, and convenience.

Listing is courtesy of: KELLER WILLIAMS REALTY PORTFOLIO COLLECTION (727-489-0800)

Listing Agent: Helen Spanos (727-798-2195)

Remarks: One or more photo(s) has been virtually staged. Must see WITH AN ASSUMABLE LOAN! 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 1,240 sq ft with an additional 200 sq ft (approximate) 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. Per records, major updates include a roof (2016), AC (2019), and several windows have been replaced! 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!

Listing is courtesy of: KELLER WILLIAMS REALTY- PALM H (727-772-0772)

Listing Agent: Gary Ubaldini (727-420-1765)

Remarks: This delightful property is perfect as a starter home, rental, retirement retreat, or vacation getaway! You own the land, enjoy low property taxes, a low quarterly HOA fee, and there’s no need for flood insurance! Pets are allowed. There are two driveways, one in front and one in the back, plus a carport with access from a different street in the back. There is a block unattached in-law suite with a private entrance separate from the main house. The Beaches and Shopping destinations make it an appealing choice for those seeking a convenient and accessible lifestyle. Residents can enjoy the proximity to various shopping, dining, and entertainment options, as well as the nearby beaches for recreational activities. This meticulously maintained, charming Mobile Home is in Move-In Ready Condition!

Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)

Listing Agent: John Barteau (813-833-7890)

Remarks: Welcome Home. Charming home in a peaceful, low-maintenance neighborhood — no HOA and no CDD! This beautifully remodeled block home features 3 bedrooms and 2 baths with a smart split-floor plan that provides privacy and flow. The one-car garage and fully fenced backyard add convenience and security, while the tile floors throughout make upkeep easy. Interior highlights include a bright, open kitchen with stainless steel appliances, granite countertops plus a raised bar-height counter for casual dining, and a convenient pot filler off the backsplash. Both bathrooms have been fully updated and feature luxury vanities. Additional updates include a newer roof, updated HVAC, and a newer water heater. Back covered patio faced west for sunsets and there is plenty of room to add a swimming pool. Perfect for first-time buyers or investors looking for a rental-ready property (NO HOA Or Rental Restrictions). Enjoy Florida mornings and backyard sunrises, with easy access to shopping, dining, top-rated beaches, and the Historic Tarpon Springs Sponge Docks. Commuting is simple to Tampa, Clearwater, and St. Petersburg. Tours Available

Listing is courtesy of: FRANK ALBERT REALTY (813-546-2503)

Listing Agent: Sean Bowes (239-470-0236)

Remarks: This charming 2 bedroom, 1 bath home with Florida room(easy 3rd bedroom/office) offers newer flooring, fresh interior paint, and a 2024 roof for peace of mind. Beautiful paver patio in the back yard, great for grilling and chilling with family and friends. Large back porch is great for all 4 season! Ideally located near everyday conveniences and just a short drive to area beaches. Schedule your private showing today! A/C-2008, ROOF-2024.

Listing is courtesy of: RE/MAX ALLIANCE GROUP (727-845-4321)

Listing Agent: Dj Arrazcaeta Jr, Llc (727-808-6066)

Remarks: This charming 3-bedroom, 2-bathroom home with a 1-car garage, features a cute stone façade, an extra-wide driveway offering generous parking, and a sidewalk that adds to the neighborhood’s walkable feel. A covered front entry welcomes you in, accented by decorative wood shake shingles, and a small tiled front porch, perfect for enjoying a quiet moment outdoors. Step inside to a bright foyer with white tile flooring that sets the tone for the home’s clean and comfortable layout. To the right, the living room features wood-look laminate flooring and a large window that fills the space with natural light, creating a warm and welcoming atmosphere. Straight ahead from the foyer, the kitchen and breakfast nook open up with white tile flooring and a functional, airy design. The kitchen is equipped with stainless steel appliances, an open pantry, a small breakfast bar, and a unique pass-through opening above the double sink that connects visually to the adjacent living space—perfect for entertaining or staying connected while cooking. A door from the kitchen provides direct access to the garage for added convenience. Just beyond the breakfast nook, you’ll find a spacious additional room that can easily serve as a formal dining area or a comfortable family room, offering flexibility to suit your lifestyle. The primary bedroom features large square tile flooring, a walk-in closet, and an ensuite bathroom with white cabinetry, a single vanity, and a step-in shower. A second bedroom includes two built-in closets, while the third bedroom offers tile flooring and a built-in closet of its own. The second bathroom is equipped with a step-in shower and grab bars for added accessibility. Sliding glass doors from the family or dining area lead into a large sunroom currently being used as an additional bedroom. This light-filled space features tile flooring and an abundance of windows, making it ideal as a sunroom, guest space, home office, or hobby room. Several exterior windows are fitted with awnings, adding both charm and shade. Out back, the rear yard provides a spacious canvas with plenty of room to add future enhancements such as a garden, expanded patio, outdoor entertaining area, or other custom improvements; ready for you to make it your own. Living in Holiday places you close to Anclote River Park and Anclote Gulf Park for waterfront views, boating, and sunsets, the famous Tarpon Springs Sponge Docks for dining and culture, nearby Gulf beaches for relaxation and fishing, and convenient access to shopping, restaurants, and everyday essentials along US-19. This home offers comfort, flexibility, and a great location to enjoy the Florida lifestyle.

Listing is courtesy of: RE/MAX MARKETING SPECIALISTS (352-686-0540)

Listing Agent: Ross Hardy (352-428-3017)

Remarks: Live the Florida Dream in this Beautiful 2 Bedroom 2 Bath Block Home with Oversized Garage in Desirable Crest Ridge Gardens! Newer 2022 Dimensional Roof! Featuring Open Floor Plan with Terrazzo Floors through out. Eat in Kitchen with Newer Refrigerator and Stove. Bonus Room that can be easily converted into 3rd bedroom or office. Freshly Painted and Ready to Move in Today! So Many Extras! Large Fenced in Back yard with 2 Sheds, carport and Double Gates on each side of property to access backyard for parking RV, Boat, Camper, Trailer or any other Toys! Perfect Private Backyard for Buyer that needs Outdoor space! This property is located in an No Flood Zone X and has No Hoa fees or Cdd fees! Easy Access to Highway 19 and minutes from Beaches, Schools, Restaurants and Shopping! 3 Miles to Famous Tarpon Springs Sponge Docks! Call Today for your private showing!

Listing is courtesy of: COLDWELL BANKER REALTY (727-781-3700)

Listing Agent: Linda Karpathios (727-488-5453)

Remarks: Under contract-accepting backup offers. Discover your next opportunity in this charming 4 bed / 2 bath home in Holiday’s Aloha Gardens! With 1,226?sqft of bright, open living space, this single-story residence boasts abundant natural light, thanks to large windows and ceramic tile floors throughout. Stove, fridge, and a handy microwave included. Both bathrooms have been refreshed with contemporary vanities, fixtures, and mirrors. The layout includes generously sized bedrooms and a convenient 1-car attached garage. Step outside to a spacious backyard perfect for barbecues, gardening, or relaxed outdoor enjoyment. Nestled in a quiet neighborhood near US-19, this home provides easy access to local parks, shopping, dining, and the area’s beautiful beaches like Fred Howard Park and the Tarpon Springs Sponge Docks

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Kevin Byrne (813-613-0752)

Remarks: Under contract-accepting backup offers. Beautiful 2-bedroom, 1.5-bathroom home in the heart of Holiday, featuring new windows, a large fenced yard, a screened patio, and fresh remodeling throughout, all in a fantastic location close to beaches, restaurants, and shopping. You must see this one before it’s gone. The property has no flooding history and is not in a flood zone, offering peace of mind and easy Florida living.

Listing is courtesy of: F I GREY & SON RESIDENTIAL (727-495-2424)

Listing Agent: Anita Mccracken (727-776-4638)

Remarks: One or more photo(s) has been virtually staged. Beautifully renovated 2-bedroom, 1-bath home located in a NO FLOOD ZONE, with NO HOA, in the heart of Holiday. This beautiful property features a newer roof (2022), brand-new AC (2026), a brand-new kitchen (2026) with beautiful quartz countertops, a renovated bathroom, and fresh paint inside and out. The open floor plan provides a bright, spacious layout designed for everyday living and entertaining. Enjoy a beautiful screened porch great for relaxing outdoors. Conveniently located near US-19, top-rated schools, shopping, dining, and just minutes from historic Tarpon Springs and beautiful Gulf Coast beaches, this move-in ready home delivers the perfect blend of comfort, style, and location. Don’t miss out on this incredible opportunity!

Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)

Listing Agent: Steven Koleno (804-656-5007)

Remarks: Welcome to this beautifully built 2-story townhome offering modern comfort and effortless living. Featuring 3 bedrooms, 2.5 baths, and a 1-car garage, this home showcases a bright, open-concept first floor perfect for entertaining, with seamless flow between the kitchen, dining, and living areas, plus a convenient half bath. Upstairs, enjoy a thoughtfully designed split-bedroom layout for added privacy. The spacious primary suite includes dual sinks, a walk-in closet, and a well-appointed ensuite bath, while two additional bedrooms share a full bath. Smart home features include a WiFi-enabled garage opener and NEST thermostat. Low HOA fees cover exterior maintenance, cable, and high-speed internet—and NO CDD fees. Ideally located near US-19 and Highway 54, just minutes from the charm of Tarpon Springs, shopping, dining, and Gulf beaches.

Listing is courtesy of: HIGH POINT REALTY INC (727-466-6697)

Listing Agent: David Kerr (727-804-2116)

Remarks: Currently tenant-occupied, but showings are available by appointment. Please contact the listing agent to coordinate access. Well-maintained, move-in ready home in a sought-after community available as either a turn-key rental or stunning personal residence.

Listing is courtesy of: STAR BAY REALTY CORP. (813-533-6467)

Listing Agent: Dan Bulka (801-979-5548)

Remarks: Do not hesitate on this meticulously maintained, one-owner villa in the Gulfwinds community. This exceptional corner-lot property is situated on a beautifully landscaped open space overlooking a pond, offering both privacy and scenic views. As one of the larger units available, the home features three bedrooms, two full bathrooms, and a dedicated den or office space complete with French doors and a decorative transom window. The interior is highlighted by high ceilings and porcelain plank tile flooring throughout. The kitchen is equipped with stainless steel appliances and quartz countertops, opening directly into a spacious great room. The split-bedroom layout ensures privacy for the owner’s suite, which includes dual vanities with updated granite tops, a garden tub, and a walk-in closet. Additional features of the home include a covered rear lanai, a brick paver patio, a separate laundry room with a washer and dryer, a generator, and a garage ceiling storage rack. The Gulfwinds community is an all-ages, pet-friendly neighborhood located in a no-flood zone. The monthly HOA provides significant value by covering lawn care, exterior maintenance (including the roof), internet, cable. Residents also enjoy access to a resort-style pool and recreation area, as well as lighted sidewalks and a bike trail connected to the Pinellas Trail. The location is conveniently situated just ten minutes from the Sponge Docks, local marinas, parks, and top-rated schools. Whether you are looking for a primary residence, a seasonal retreat, or an investment opportunity, this villa offers an incredible combination of luxury and convenience.

Listing is courtesy of: MARK SPAIN REAL ESTATE (855-299-7653)

Listing Agent: Jim Maiorano (727-580-5199)

Remarks: Under contract-accepting backup offers. A PRIME LOCATION APPROXIMATELY4 MILES TO THE PINELLAS COUNTY LINE. A BLOCK HOME WITH A NEWER ROOF, 3 SPACIOUS BEDROOMS, 2 I/2 BATHS, AND OVERSIZED 1 CAR GARAGE. WINDOWS WERE REPLACED IN 2019. OPEN FLOOR PLAN WITH A LIVING/DINING ROOM COMBO AS YOU ENTER THE FRONT DOOR. A LOVELY FAMILY ROOM WITH A WOOD BURNING FIRPLACE FOR THOSE CHILLY EVENINGS. 3 SPACIOUS BEDROOMS WITH ONE A POSSIBLE IN-LAW AS HAS A PRIVATE ENSUITE BATH WITH A GARDEN TUB, A LINEN CLOSET, AND A PRIVATE OUTSIDE ENTRANCE. PRIMARY BATHROOM HAS JUST HAD A BEAUTIFUL WALK-IN SHOWER INSTALLED BY WEST SHORE HOMES. FRONT AND SIDE SCREENED PATIOS TO ENJOY THE FRESH AIR AND A FULLY FENCED BACKYARD WITH TWO STORAGE SHEDS. EXTRA LARGE DRIVEWAY WITH PLENTY OF PARKING, AN OVERSIZED ONE CAR GARAGE WITH A WASHER & DRYER, A GARAGE DOOR OPENER AND 1/2 BATH.

Listing is courtesy of: PITTA AND ASSOC INC (727-458-2738)

Listing Agent: Julie Pitta (727-458-2738)

Remarks: Great buy on this 3 bedroom one & 1/2 bath home in Holiday. Garage has been converted into an additional room for added living space. Over 1,600 square feet, block construction. Located on a quiet cul-de-sac with a spacious back yard. Enclosed rear patio. No flood insurance required. Being sold "as is".

Listing is courtesy of: GULF TO BAY REAL ESTATE (727-586-1500)

Listing Agent: Ann Mcintosh (727-686-3147)

Remarks: Move-in ready three-bedroom, two-bathroom home in the Lullaby Gardens neighborhood. This residence features an inviting interior highlighted by tall ceilings in the living room, creating an airy and spacious atmosphere. The updated kitchen is a standout, boasting granite countertops and modern stainless steel appliances. The layout offers a perfect blend of comfort and functionality, extending to a private, fully fenced backyard that provides a secure space for outdoor activities. Conveniently located just miles from multiple Gulf beaches and the famous Sponge Docks, this home is perfectly positioned for enjoying local dining, shopping, and entertainment. With its prime location and move-in ready condition, this home is ideal for enjoying the best of coastal Florida living. Schedule your private showing today!

Listing is courtesy of: ENTERA REALTY LLC (888-216-6364)

Listing Agent: Robert Salmons (888-216-6364)

Remarks: Under contract-accepting backup offers. Welcome Home! This beautifully updated home is move-in ready and perfect for your next chapter. As you step inside, you’re welcomed by a spacious family room that flows effortlessly into the rest of the home. To your right, you’ll find a hallway bath along with a comfortable guest bedroom, while the owner’s suite features a private ensuite with a walk-in shower and a generous walk-in closet. Both bathrooms have been tastefully updated, and ceramic tile flooring runs throughout the entire home, offering durability and a clean, modern look. The kitchen has been recently updated and comes equipped with brand-new appliances, making it the perfect space for cooking and entertaining. Toward the back of the home, an additional flex room offers endless possibilities—ideal for a home office, bonus room, or easily converted into a third bedroom. Step outside to enjoy a screened-in lanai overlooking a fully fenced backyard—perfect for relaxing or hosting. Unwind in the evenings on your private dock, whether you're enjoying a glass of wine or casting a line to try your luck at fishing. With no HOA, you’ll appreciate the freedom and flexibility this property offers. Schedule your private showing today and make this dream home yours!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Vinh Quang Chau (813-352-6536)

Remarks: Under contract-accepting backup offers. Welcome home! This charming and affordable starter home is a perfect opportunity for buyers looking to get into homeownership without breaking the bank. Featuring a clean, well-maintained interior and brand-new appliances, this home is truly move-in ready and ideal for first-time buyers, downsizers, or anyone looking for a great value. Enjoy a bright open living space, easy-care flooring, and plenty of natural light throughout. The home offers a cozy layout with comfortable bedrooms and a functional kitchen that’s been refreshed and updated for everyday living. Step outside to a spacious yard with room to relax, garden, entertain, or store your toys and best of all, NO HOA! If you’ve been waiting for a solid home at an affordable price point, this one checks the boxes: clean, updated, and ready for its new owner. Schedule your private showing today!

Listing is courtesy of: COASTAL PROPERTIES GROUP INTER (813-553-6869)

Listing Agent: Zach Senter (727-735-4021)