Holiday Homes For Sale & Real Estate - 324 homes

Remarks: This 3 bedroom, 1 and a half bathroom home is nestled on a spacious, oversized lot, offering room to roam, play, and entertain. The true highlight is its incredible location. You're just a short distance from everything you need and love: from trendy shops and delicious restaurants to exciting entertainment venues and, of course, the stunning nearby beaches.

Listing is courtesy of: PREMIER REALTY CONSULTANTS (727-939-7811)

Listing Agent: Asteropi Tsalickis (727-967-0633)

Remarks: BEST VALUE IN GULFWINDS – A TURNKEY OPPORTUNITY WITH BUYER FLEXIBILITY! Major updates are already handled with a 2022 HVAC system and 2018 WATER HEATER, plus a WATER SOFTENER giving buyers peace of mind from day one. If you’ve been waiting for the right opportunity in Gulfwinds, this is it. This 3-bedroom, 2-bath home with 1,740 sq ft delivers space, updates, a private backyard, and a true maintenance-free lifestyle—positioned to stand out in today’s market. Inside, you’ll find vaulted ceilings with crown molding and an open layout that flows seamlessly between the living, dining, and kitchen areas—creating a bright, inviting space that lives larger than expected. The split floor plan offers privacy, with a spacious primary suite featuring a walk-in closet, dual vanities, soaking tub, and frameless glass shower. Secondary bedrooms are perfect for guests or a home office. The kitchen is both functional and spacious, featuring 42-inch cherry wood cabinetry, ample counter space, GE appliances, and Moen fixtures. Step outside to a screened lanai overlooking one of the larger fenced backyards in the community, ideal for relaxing or entertaining. The oversized two-car garage is highlighted by a newly installed premium decorative epoxy floor coating with an attractive flake finish, creating a clean, showroom-quality appearance while providing exceptional durability, stain resistance, and easy maintenance. Built with durability in mind, this home includes concrete block construction, hurricane shutters, low-E double-pane windows, R-30 insulation, and a 200-amp service. Gulfwinds offers a true maintenance-free lifestyle, with HOA covering roof maintenance, lawn care, exterior painting, cable, internet, community grounds, and a resort-style pool. Located just minutes from beaches, marinas, parks, shopping, dining, and the Tarpon Springs Sponge Docks, this home combines convenience with value. Homes in this price range are moving—don’t miss your chance. SELLER OFFERING $5,000 CREDIT TO BUYER AT CLOSING WITH ACCEPTABLE OFFER. Schedule your showing today!

Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)

Listing Agent: Benjamin Elkins (202-794-3424)

Remarks: Income-Generating Property - the best Price! "Excellent investment opportunity in the Holiday market! This 3-bedroom, 2-bathroom property stands out for its generous size (2,628 sq. ft.) and excellent condition, including a brand-new roof and a beautiful in-ground pool. The house is being sold with a tenant already in place, paying $1,750/month, eliminating the wait time to find a new tenant. Priced $50,000 below appraised value, this property offers an immediate entry into the market with equity. Ideal for investors seeking both profitability and security!

Listing is courtesy of: GLOBAL FORTUNE REALTY LLC (813-876-8329)

Listing Agent: Francisco Rojas (813-345-7177)

Remarks: Under contract-accepting backup offers. Welcome to 3410 Darlington Rd,  the perfect move-in-ready opportunity for anyone looking for a beautifully updated home without the renovation headaches. This 3-bedroom home features a bright, modern interior with brand new luxury vinyl plank flooring throughout, fresh paint, new light fixtures and other stylish updates completed in 2026. The fully renovated kitchen shines with white shaker cabinetry, stone countertops, attractive tile backsplash, and all new stainless steel appliances, creating a clean and timeless space perfect for everyday living and entertaining. The bathrooms have also been tastefully updated with fresh modern finishes. Major improvements include a new roof in 2024 and HVAC in 2022 for added peace of mind. Enjoy a circular driveway and attached 1-car garage for plenty of parking. This turnkey home combines major updates and affordability all in one package.

Listing is courtesy of: BLAKE REAL ESTATE INC (727-359-0388)

Listing Agent: Angela Balthazar (727-421-0272)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated 4-bedroom, 2-bathroom block home offering the perfect blend of modern style, comfort, and functionality. From the moment you arrive, the inviting covered front entryway creates warm curb appeal, while the bright and airy interior immediately makes the home feel open and welcoming. Inside, you’ll find a thoughtfully designed split floor plan with stylish updates throughout, including brand-new windows and wood-look tile flooring flowing seamlessly throughout the home, creating a clean, modern, and cohesive feel. Originally a 2-bedroom, 1-bathroom home, the property was thoughtfully expanded into a spacious 4-bedroom, 2-bathroom layout with all additions and improvements completed with permits and inspections for added peace of mind. The kitchen is a true standout, featuring crisp white shaker cabinetry, sleek quartz countertops, and brand-new appliances that make both everyday living and entertaining feel effortless. Both bathrooms have been fully renovated with clean, modern finishes, creating spa-like spaces that feel fresh and elevated. The spacious primary bedroom offers a unique touch with French doors leading directly outside, adding character and flexibility to the space. Major upgrades provide exceptional peace of mind, including a brand-new HVAC system with upgraded ductwork, a new roof, a new water heater, upgraded 200-amp electrical main service, all new electrical wiring throughout the home, and updated plumbing throughout. Outside, the fully vinyl-fenced backyard offers privacy and plenty of room to relax, entertain, or create your dream outdoor oasis. The oversized 2-car carport adds convenience and functionality, while the solid block construction offers durability and classic Florida living appeal. Perfectly located just minutes from US-19 with endless dining, shopping, and everyday conveniences nearby, this home is also close to the famous Tarpon Springs Sponge Docks, beautiful waterfront scenery, and the trails and nature views of Anclote River Park, giving you the best of both convenience and coastal charm.

Listing is courtesy of: NETWORTH REALTY OF TAMPA, LLC (813-282-7444)

Listing Agent: Valeria Aliaga (813-990-7319)

Remarks: Under contract-accepting backup offers. Completely renovated and move-in ready, this 3-bedroom, 1-bath charmer in Holiday checks all the boxes. Solid block construction paired with a brand-new roof offers peace of mind, while the stylish interior delivers today’s most sought-after finishes. The all-new kitchen features white shaker cabinetry with soft-close drawers, a pantry, lazy Susan, farm sink, microwave hood, range, and side-by-side refrigerator with ice maker. Luxury vinyl flooring runs throughout the home, complemented by solid wood interior doors, custom window trim, and ceiling fans. Major updates include new impact-rated windows and doors, a new AC system, and a new water heater. The beautifully renovated bathroom showcases oversized 24x48 porcelain tile, granite countertops, and a white shaker vanity. Step outside to a fully fenced yard with brand-new vinyl fencing, offering plenty of space to add a pool or create your dream outdoor retreat. Enjoy two rear patio decks—perfect for relaxing or entertaining. A one-car garage includes washer and dryer hookups for added convenience. With its open floor plan, this home lives larger than expected and is ideal for a first-time buyer, downsizer, or anyone looking for a turnkey property.

Listing is courtesy of: COMPASS FLORIDA LLC (813-365-9935)

Listing Agent: Beth Raulerson (813-422-4846)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully renovated 3-bedroom, 2-bath single-family home in Holiday! This move-in-ready property features a bright open floor plan with stylish vinyl laminate flooring throughout, creating a modern and inviting living space. The fully updated kitchen is a true highlight, showcasing elegant quartz countertops, brand-new appliances, and plenty of space for cooking and entertaining. Major upgrades provide peace of mind, including a full roof replacement completed in March 2026 and a newer A/C system installed in 2023. Step outside to enjoy a spacious backyard with plenty of room for outdoor living, gardening, or future enhancements. The garage offers a unique opportunity to convert into a mother-in-law suite or additional living space, adding flexibility and value. Don’t miss this turnkey home combining comfort, style, and potential!

Listing is courtesy of: PEOPLE'S CHOICE REALTY SVC LLC (813-933-0677)

Listing Agent: Miguel Davila, Pa (813-842-1061)

Remarks: Price reduced! Motivated seller offering $6,000 toward buyer’s closing costs, prepaids, or rate buy-down with acceptable terms! Move-in ready 3-bedroom, 2-bath home offering 1,392 sq ft of comfortable living space in Holiday. This well-maintained property features tile flooring throughout, providing both durability and easy maintenance. The functional layout offers spacious living areas and a seamless flow, ideal for everyday living and entertaining. Enjoy the outdoors with a fully fenced yard, perfect for pets, gatherings, or added privacy, along with a large shed for extra storage. Located outside of a flood zone and with no HOA, this home provides added peace of mind and flexibility. Conveniently situated near US-19 with easy access to Fred Howard Park Beach, as well as shopping, dining, schools, and local parks. A great opportunity for homeowners or investors alike. Schedule your showing today.

Listing is courtesy of: DALTON WADE INC (888-668-8283)

Listing Agent: Arlethys Cordero Beltran (813-679-0566)

Remarks: Welcome to the established and friendly Holiday Lake Estates community, a quiet residential neighborhood just a stroll from the Anclote River and Gulf Coast beaches. This charming home features 3 bedrooms, 2 bathrooms, and a convenient 1-car garage. With some recent updates and 1558 sq. ft. of living space, the home offers a comfortable floor plan perfect for families or those seeking serene Florida living. Enjoy proximity to local parks, fishing, and boating, with easy access to shopping, dining in Tarpon Springs. The spacious backyard provides the perfect space for outdoor relaxation or entertaining. Don't miss this opportunity to own this beautiful property!

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

Listing Agent: Corey Auld (727-657-7977)

Remarks: Under contract-accepting backup offers. Short Sale. *Short Sale Opportunity!** Seize this remarkable chance to own your dream home. This stunning 2-bedroom, 2½-bathroom residence, featuring a one-car garage and constructed in 2023, is situated in a serene and well-maintained neighborhood. The upper level includes two bedrooms, each with its own private bathroom, while the downstairs boasts a spacious living area that offers picturesque views of the pond, all under a covered patio. Additionally, there is an outdoor storage room for added convenience. This home seamlessly combines comfort, style, and value.

Listing is courtesy of: MARTINEZ 2 & ASSOCIATES OF FLO (813-431-8785)

Listing Agent: Stephanie Bonefont (813-504-5758)

Remarks: Welcome home to this lovely Four bedroom two bath home with a fantastic front porch and fenced backyard! This property boasts fresh paint and new appliances with ceramic tile throughout. New roof January 2025. Fantastic oversized one car garage and an oversized driveway make for fantastic parking. This property has the fenced backyard with an additional parking pad on the side of the home for that boat or RV. Come take a look at this home and make it your own today.

Listing is courtesy of: GULF PROPERTY MANAGEMENT LLC (727-639-1949)

Listing Agent: Joel Rodgers (727-639-1949)

Remarks: INVESTOR SPECIAL – OWNER FINANCING AVAILABLE! Opportunity knocks at 1846 Hoyle Drive in Holiday. This 2/1-bedroom, 1-bath mobile home with land included offers significant upside potential for investors, rehabbers, landlords, and creative buyers. Property requires repairs, updating, and cleanup and is being sold AS-IS. Seller will consider owner financing for qualified investor buyers. Flexible financing structures may be available depending upon buyer qualifications, down payment, and proposed use of the property. Property is intended for investment purposes and may be suitable for buy-and-hold investors, rehab projects, rental portfolios, or future resale strategies. No lot rent. Convenient location near shopping, restaurants, parks, beaches, and major transportation routes. Affordable entry into the Holiday market with substantial value-add potential. Buyer responsible for all due diligence regarding financing, title, insurance, occupancy requirements, and future transferability of financing arrangements. Terms subject to seller approval. Room dimentions are estimate and not guaranteed. Property is as is and MLS data is not guaranteed.

Listing is courtesy of: ADVANCED REALTY TEAM INC (727-734-8286)

Listing Agent: George Beardsley (727-251-5323)

Remarks: Under contract-accepting backup offers. Take advantage of a unique opportunity to own an expansive duplex that includes both units of the property. Each side features 3 bedrooms and 2 bathrooms with nearly 1,700 square feet of living space, totaling 3,384 heated square feet and 7,062 square feet overall, with one unit being sold furnished for added convenience. Both units offer oversized two-car garage doors, ideal for car enthusiasts, contractors, or anyone needing ample storage or workspace. Well-suited for personal use or as a vacation rental or investment property, this duplex is ideally located along the New Anclote Bike Trail and directly across from Anclote River Park, which offers a public boat ramp, sandy beach, picnic areas, and a playground. This setting provides the perfect balance of outdoor recreation and relaxation, all just minutes from the shops, dining, and waterfront attractions of historic Tarpon Springs, making this versatile property a standout opportunity.

Listing is courtesy of: COLDWELL BANKER REALTY (863-294-7541)

Listing Agent: Erin Floyd (863-412-2286)

Remarks: **WOW! BEST DEAL in HOLIDAY with NO HOA!** This contemporary one-story home is sure to steal your heart. Homes like this don’t come available very often, and this one has everything you’ve been dreaming of with a BRAND NEW ROOF! Get ready to fall in love… this home offers wide-open living spaces with tons of natural light and elegant waterproof luxury plank flooring throughout the living areas. As you walk in, you will love the welcoming formal living room with cozy dining space leading you to the kitchen. The kitchen is a chef's dream with tons of countertop space, ALL-WOOD white shaker-style cabinets, gorgeous QUARTZ COUNTERTOPS, and STAINLESS STEEL APPLIANCES, creating a true centerpiece for the gatherings. The master bedroom is a perfect retreat at the end of a long day. Featuring a large closet space, and a luxurious en-suite bathroom, the master bedroom offers serenity and comfort. Thanks to a great floor plan, the two additional bedrooms and a family-sized hall bathroom give everyone plenty of space to stretch out. The backyard is the perfect oasis for enjoying the year-round Florida lifestyle in your FENCED YARD. Other great features include an indoor laundry area, fresh paint, and fresh carpet throughout. All that's left to do is move right in. Run, don’t walk to see this incredible home!

Listing is courtesy of: PINEYWOODS REALTY LLC (813-225-1890)

Listing Agent: Stephen Scott Pa (813-688-0068)

Remarks: Virtually Staged. Welcome home to this beautiful 3-bedroom, 2-bathroom home with a two-car garage situated on the serene shores of Lake Conley. As you step inside, you will immediately appreciate the bright, open feel of the home, enhanced by a neutral color palette that creates a warm and inviting atmosphere. The spacious living room provides plenty of room for relaxing or entertaining guests, while the adjacent dining area, conveniently located between the living room and kitchen, offers the perfect setting for everyday meals or gatherings. The well-appointed kitchen features stainless steel appliances, granite countertops, and a convenient breakfast bar, making it both functional and stylish. In addition to the living room, the home offers a large family room, providing even more space for entertaining, relaxing, or creating a flexible living area to suit your needs. Just off the family room, you will find an enclosed back porch, the perfect place to unwind while enjoying peaceful views of the lake. Step outside to the open dock, where you can park your boat and enjoy easy access to the water, making lakefront living a reality. The primary bedroom is generously sized and features an en-suite bathroom complete with a large vanity offering plenty of storage and a walk-in shower. Conveniently located near US 19, this home provides easy access to shopping, dining, entertainment, and medical facilities, offering both comfort and convenience. Don’t miss this opportunity to enjoy lakefront living—schedule your private showing today!

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

Listing Agent: Dawn Walls

Remarks: Built in 2023, this townhome offers modern construction without the typical new-build growing pains. The open main level features ceramic tile flooring, recessed lighting, a functional open-living layout that includes a breakfast bar flowing directly into the living room—ideal for everyday living and casual entertaining. The kitchen is equipped with quartz countertops (matched throughout the home), a deep farmhouse sink with a touchless faucet, black shaker cabinetry, stainless GE appliances, spacious closet pantry plus an island that anchors the space and provides extra cabinetry. Upstairs, all bedrooms are thoughtfully positioned, with the primary suite privately separated from the secondary bedrooms. The primary bedroom includes a walk-in closet and an en-suite bath with dual vanities and a glass-enclosed shower—an owner upgrade not included with standard new construction. The laundry closet with stackable washer/dryer combo is also located upstairs for everyday convenience. The screened lanai, another owner-added improvement, provides a comfortable outdoor living space with ceiling fan and peaceful greenery views. Unlike many association communities, grilling is permitted. Additional features include Ecobee smart thermostat with app-based temperature control, pre-installed TV mounts, aluminum storm shutters for doors and windows providing potential insurance savings. Parking is well-covered with a one-car garage, driveway parking, and nearby guest spaces along with the community mailbox located close to the home. The community has no CDD fees and no land lease, and the association handles ground maintenance with irrigation and exterior maintenance to include the roof. Quarterly association dues are $571.80, which amounts to $190.60 per month, covering cable, internet, common area upkeep and property manager. Located in Holiday, FL—Pasco County’s closest northern community to Pinellas County—this area offers a lower cost of living while remaining approximately 30 minutes from the Gulf beaches and the Tarpon Springs Sponge Docks. Outdoor and lifestyle amenities nearby include Anclote River Park, Key Vista Nature Park, and the Jay B. Starkey Wilderness Preserve, offering miles of hiking and biking trails. For boaters and water lovers, the Anclote sandbar is a popular weekend destination, with local sandbar groups often gathering for fun in the sun. Easy access to US-19 provides convenient connections to both Pasco and Pinellas County destinations.

Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)

Listing Agent: Julie Sartain (727-420-6107)

Remarks: WOW! Move in ready and full of potential! This charming home features bright open living spaces and great outdoor area complete with brand new fence! Great open space for a bar-b-q's or put your own swimming pool! This 2 bederoom home has an extra room that could be made into a 3rd bedroom, office or guest space. The A/C is 2021, Roof 2022 and new Hurricane-rated Garage door and opener 2025. New Hurricane rated Windows in the Living room, 2nd bedroom and a new Hurricane rated Sliding Glass Doors in the Primary Bedroom! Whether you are looking to make this your full time or or Winter retreat or investment or a air B & B! Located near Shopping, Sponge Dockes and beaches! Schedule your showing today! This won't last!

Listing is courtesy of: YELLOWFIN REALTY (813-347-7547)

Listing Agent: Tamie Hopp (813-277-4957)

Remarks: Under contract-accepting backup offers. Welcome to this beautifully updated 3 bedroom, 2 bathroom home offering the perfect blend of privacy, functionality, and modern Florida living. Located on a quiet street with no direct front neighbors and added privacy from a neighboring water department-owned lot, this move in ready property is conveniently close to shopping, dining, parks, schools, medical facilities, and Gulf beaches. Inside, you’ll find a bright open-concept layout with abundant natural light, spacious living areas, and durable tile flooring throughout most of the home. The updated kitchen features newer countertops, newer refrigerator, extensive cabinetry, built-in pantry storage, and oversized bar seating ideal for entertaining. The split-bedroom floor plan provides added privacy, while the spacious primary suite offers excellent closet space. Outside, enjoy the oversized fenced backyard with covered outdoor living space, patio area, and plenty of room for pets, gardening, or a future pool. Additional highlights include fresh exterior paint, updated windows, oversized 2-car garage, covered front porch, and rear covered porch. Whether you're searching for a primary residence, seasonal getaway, or investment opportunity, this well-maintained Holiday home offers exceptional value and convenience. (ROOF-2013)(FLAT ROOF-2023)(A/C-2015)

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

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

Remarks: Welcome to waterfront living in Holiday! This beautifully maintained 2-bedroom, 2-bath home offers 1,334 square feet of comfortable living space with no HOA and peaceful pond views. Enjoy your own private dock, perfect for fishing, sunset watching, stargazing, or launching a canoe or kayak. The waterway also allows small boating with a trolling motor, making it ideal for quiet, scenic cruising right from your backyard. Inside, the home features a bright and spacious layout with abundant natural light, tile flooring throughout the main living areas, waterproof laminate flooring, and an updated kitchen with a new refrigerator, range, and dishwasher installed in 2025. Major updates provide peace of mind, including new interior and exterior doors in 2025, updated windows in 2011, a new roof in 2020, and A/C and furnace replacements in 2020. Relax and enjoy tranquil water views right from your backyard or venture out to nearby Gulf Coast attractions. Conveniently located near Fred Howard Park, Howard Park Beach, Key Vista Nature Park, Anclote River Park, and the historic Sponge Docks in nearby Tarpon Springs, known for its waterfront dining, shopping, and entertainment. Ferry access to Anclote Key Island is also just minutes away, offering pristine beaches and outdoor adventures. Home sold "as-is" for seller's convenience. NOTE: THIS PROPERTY IS NOT LISTED AS A RENTAL

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

Listing Agent: Nicole Dufala (727-656-8145)

Remarks: Tiki Village. NON-FLOOD ZONE. Only $400 a year. Gated. 55 and Older. You OWN THE LAND. Massive front porch 9 feet by 19 feet. This spacious home stands out as one of the community’s largest units at 1344 Sq Feet. Home has an oversized living room, expansive dining area and generously sized kitchen, also features a screened-in side porch and a carport. The hall bathroom features a high-end walk-in jetted bathtub, offering comfort, accessibility, and a spa-like experience. The primary suite includes a beautifully updated shower with a brand-new surround. Utility room with full sized washer and dryer. While the kitchen offers abundant space and storage, it is dated and presents a great opportunity for a buyer to update and personalize to their taste. Low Maintenance lot, Home is on a dead end, so there is less traffic. Tiki Village is owner/member managed and has made significant improvements, including reducing the annual fee from $520 to $400 a year. Propane tank is leased.

Listing is courtesy of: FLORIDA REAL ESTATE PARTNERS (727-409-4663)

Listing Agent: Randal Jenkins (727-409-4663)