Holiday Homes For Sale & Real Estate - 327 homes

Remarks: Here is your opportunity to watch the wildlife and beautiful sunsets from the finished enclosed porch or the outside concrete patio overlooking the lake for your enjoyment. Home feature laminate flooring, dining area, split bedrooms, 2 full baths, new front door, new washer, range/oven. Home comes completely furnished and features loads of storage and linen space. You OWN YOUR OWN LAND in this 55+ community with low monthly maintenance fee of $143.00 per month which includes, lawn maintenance, trash removal, heated year-round pool, Clubhouse, maintenance of private roads, and much more. Sold As Is. Buyer to verify all information that is deemed to be accurate. Easy to show. Measurements are approx.

Listing is courtesy of: CITY BREEZE ACTION REALTY (727-372-9000)

Listing Agent: Stella Wooster (727-247-2790)

Remarks: Price improved! This 2/2 Sunny Florida Lakeview Home beckon you! Come Enjoy this peaceful, Golfcart friendly 55+ Active Community where you OWN your Own LAND! The Low HOA monthly fee of $ 143 includes, ground maintenance, Heated Year-Round Pool, Trash removal, Private Road, Clubhouse amenities, etc., Short distance of shopping, restaurants, close proximity to Beaches, Historic Tarpon Springs with the famous Sponge Docks, Wine Festival, etc. Easy drive to Tampa or to go North. Measurements are approx. Buyer to verify all information that is deemed accurate. Sold As Is. Easy to show/view.

Listing is courtesy of: CITY BREEZE ACTION REALTY (727-372-9000)

Listing Agent: Stella Wooster (727-247-2790)

Remarks: Charming, 2-bedroom, 1.5-bathroom single-family home available for sale in Holiday. This property boasts a renovated kitchen featuring wooden cabinets paired with granite countertops, offering a classic and modern look. Key updates include ceramic tile throughout, a new HVAC system (2025), a new electric water heater (2025), and a roof from 2015. The fully enclosed rear yard features low-maintenance vinyl fencing,  ensures a safe haven for pets and play while providing a serene retreat or quiet reflection. Whether you're seeking a permanent residence or an investment opportunity, this property provides excellent flexibility. It is centrally located in Holiday, just 0.7 miles from US 19 and less than 1.5 miles from supermarkets, dining, and entertainment. The home was not impacted by rising water during the last two storms. It has been meticulously maintained and is in move-in ready condition.

Listing is courtesy of: LONDON FOSTER REALTY (305-514-0100)

Listing Agent: Hector Mendez Garcia, Pa (786-683-9407)

Remarks: Move-in ready home for you in a quiet neighborhood, but very close to shopping and easy to commute. Nicely updated and very little lived in by the owner, who was coming only for a couple of months in winter time. Roof, windows and entry door were replaced in 2015. All floors are tiled, kitchen has nice wooden cabinets, like new appliances, and washer and dryer in the garage. Furniture is negotiable. A good size enclosed back porch gives you place to relax and a very large back yard with chain link fence all around. Nice curb appeal and all rooms of good size. Owner recently installed additional insulation, for energy efficiency. This is a great opportunity for a first time buyer to enjoy homeownership.

Listing is courtesy of: OLYMPIC REALTY SERVICES LLC (727-937-0107)

Listing Agent: Maria Kastritsos (727-460-6383)

Remarks: Nicely updated 2-bedroom, 2 bath home where you own the land! This beautiful and recently updated 2-bedroom home has a newer open kitchen, updated baths, newer plank floors. The kitchen was remodeled in 2022, with shaker cabinets, appliances including dishwasher, ceiling fans and recessed lights. There is tile backsplash, a large stainless steel kitchen sink, garbage disposal and custom counter tops. The hall bath is updated with a newer and taller vanity and has tiled floors. The home has crown molding and many exterior storm shutters. It also has a total of 5 ceiling fans and the central air and heat unit replaced in 2022. It has vapor barrier and a screened porch area. There is a Florida room is in the front, with ceramic tile floors. The home has vinyl siding, storm shutters, window blinds. Laundry is in the shed. The home has a metal roof-over from 2016, and screws are recently sealed. It has a newer washer 2 years old, dryer 1 year old. There is also a front screened porch area to enjoy, perfect spot for morning coffee or an evening drink. Custom painted and sealed driveway. Home can be sold furnished with acceptable sales price. Your new home is waiting for you in the gated Lake Conley MHP, on Lake Conley, in town of Holiday. It is a highly sought after waterfront 55+gated Community, where you Own the Land, with no lot rent. It also has low taxes, as well as HOA Fees around $63.41 a month. 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. 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. This home comes with a non-potable water well for lawn and gardening. 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: Short Sale. Welcome to this beautifully maintained home in the heart of Holiday, offering the perfect blend of comfort, efficiency, and serene outdoor living. Situated on a picturesque conservation lot with a peaceful water view, this property provides a private backyard setting that’s ideal for relaxing or entertaining. Inside, you’ll find a spacious and versatile layout featuring an additional bonus living room—perfect for a second family room, office, or flex space to fit your needs. The primary suite is a true retreat, complete with a large walk-in closet, en suite bathroom, and elegant French doors that open directly to the tranquil backyard. The home is packed with valuable upgrades, including updated double-pane windows for energy efficiency and a solar panel system that helps reduce utility costs—an incredible long-term benefit for homeowners. Major systems have been taken care of, with a new roof installed in 2024 and the AC replaced in 2021, offering peace of mind for years to come. A water softener system is also in place for added comfort. Additional highlights include a spacious two-car garage and a layout that maximizes both functionality and natural light throughout. Enjoy Florida living at its finest with beautiful views, modern upgrades, and a quiet setting—all while being conveniently located near shopping, dining, and local amenities.

Listing is courtesy of: INSPIRED REALTY, LLC (727-503-7865)

Listing Agent: Tyler Grisley, Llc (727-232-3850)

Remarks: price adjustment and a very motived seller,,,Move-in ready and full of potential! This 2-bedroom, 2-bath home features an open floorplan with vaulted and cathedral ceilings, creating a bright, spacious feel throughout. The living room/dining room combo is perfect for everyday living and entertaining, while solid wood cabinets and solid surface counters add lasting quality to the kitchenEnjoy a split bedroom layout for privacy, walk-in closets, and ceiling fans for year-round comfort. Conveniently located near shopping, dining, and major roadways, this Holiday home delivers space, function, and value in one smart package.

Listing is courtesy of: HOMETRUST REALTY GROUP (813-444-5777)

Listing Agent: Donna Kroll (813-444-5777)

Remarks: Move-in ready renovated home! This 4-bedroom, 2-bath property features a fully updated kitchen with modern cabinets, granite countertops, and updated appliances. Water-resistant vinyl flooring in the main areas and new carpet in the family room for added comfort. The home also offers new impact windows and doors, new insulation for improved efficiency and energy savings. The backyard includes a pool, shed, and gazebo—perfect for outdoor entertaining. Located in a quiet neighborhood close to restaurants, shops, services, and main roads. A fantastic opportunity!

Listing is courtesy of: HOME PRIME REALTY LLC (813-497-4441)

Listing Agent: Yenislei Machado (813-609-7088)

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: Welcome to 1715 Kenilworth Street in Holiday, Florida, a beautifully renovated home offering modern updates, functional living spaces, and the added benefit of no HOA restrictions. This move-in-ready property features refreshed interiors, contemporary finishes, and a layout designed for both everyday comfort and easy entertaining. The spacious backyard includes a private pool, creating the perfect setting to enjoy the Florida lifestyle year-round. The property is currently rented on a month-to-month basis. This is an excellent opportunity to own a renovated pool home with no HOA in a desirable Holiday location.

Listing is courtesy of: LPT REALTY, LLC (877-366-2213)

Listing Agent: Alejandro Conti (321-424-8903)

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 ranch-style 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: Welcome to this charming Florida neighborhood three bedroom two bathroom mobile home in Holiday, 1,701 sq ft with NO HOA, where relaxed living and natural beauty come together to create the perfect place to call home. This inviting residence offers an ideal retreat to unwind after a long day, starting with the front wrap-around deck, a peaceful spot to enjoy your morning coffee while taking in the view of two mature oak trees gracing the front yard. Step inside and you’re welcomed by a spacious, light-filled kitchen featuring stainless steel appliances, large windows, a skylight, and an in-kitchen dining area—truly the heart of the home. The living room provides a cozy yet stylish atmosphere with a stone-faced fireplace. For dining, you’ll find both an intimate dining room accented with rustic wood paneling and a large window, as well as a family dining room designed for entertaining, complete with space for a large table, French doors, rustic wood paneling, and expansive windows that flood the room with natural light. The owner’s retreat is generously sized to accommodate a king-size bed and offers his-and-her closets, opening into a spacious bathroom highlighted by a skylight, wood-paneled ceiling, and dual-sink vanity. Two additional spacious bedrooms provide flexibility for a home office, guest room, or extra space. Outside, enjoy a fully fenced yard offering privacy and room to relax or entertain. Gather around the fire pit on warm Florida evenings to make s’mores and lasting memories. This property also includes a 12.5’ x 16’ air-conditioned and powered “Man Cave,” a 10’ x 24’ freestanding workshop, and an 8’ x 10’ utility shed, providing ample storage and workspace. Major updates include a new roof and water heater installed in 2017. The location is unbeatable—just 0.8 miles from the dog-friendly Anclote River Park, offering a boat launch, paved bike trails, playground, picnic shelters, hiking trails, swimming, kayaking, and fishing. Nearby are a bait and tackle shop, Anclote Village Marina, and Miss Vicki’s on the River restaurant, making this area a true outdoor enthusiast’s paradise. Plus, you’re only 7 minutes from the historic Tarpon Springs Sponge Docks.Whether you’re a fisherman, nature lover, or simply seeking a home with character and flexibility, this property offers something special. Schedule your private showing today and envision your future here.

Listing is courtesy of: EXP REALTY LLC (866-308-7109)

Listing Agent: Jeffrey Borham, Pa (866-308-7109)

Remarks: Under contract-accepting backup offers. Welcome to this well-maintained two-bedroom, two-bathroom home tucked away on a quiet cul-de-sac in Holiday. With a wide driveway, inviting front porch, and thoughtful updates throughout, this home offers both comfort and convenience. Major improvements include a 2022 roof and a 2021 A/C and water heater, providing peace of mind for years to come. Inside, you’ll find classic terrazzo flooring, an open floor plan, and ceiling fans throughout, creating a light and comfortable living space. The front living room flows seamlessly into the kitchen and dining area, making it ideal for everyday living and entertaining. The kitchen features a center island perfect for meal prep or casual dining, matching appliances, and a dining area just off the kitchen. Toward the back of the home, a heated and cooled sunroom offers additional living space - perfect for relaxing year-round. The primary bedroom includes an impressive wall-length closet, providing plenty of storage. The second bathroom is conveniently located in the garage, and the home also includes a new washer and dryer. Step outside to enjoy a Partially fenced-in backyard with a patio area for grilling and outdoor gatherings. A shed with power adds even more functionality, ideal for storage, hobbies, or a workshop space. Conveniently located near shopping centers, dining options, and everyday amenities, this home is a fantastic opportunity whether you’re looking for a primary residence, seasonal getaway, or investment property. Schedule your showing today!

Listing is courtesy of: EXP REALTY LLC (866-308-7109)

Listing Agent: Jeffrey Borham, Pa (866-308-7109)

Remarks: Price Adjustment on this Charming 3-Bedroom Home in Holiday Lake Estates – Close to Tarpon Springs! This 3-bedroom, 2-bathroom home with a 1-car garage sits on a desirable corner lot, just a short drive from historic Tarpon Springs and the famous Sponge Docks. Enjoy local events, waterfront dining, and easy access to Pinellas County. Featuring a newer solar panel system (2021, owned) and new roof (2023), this home offers energy efficiency and long-term savings. The spacious, fully fenced backyard includes an 8x10' vinyl shed and double gates, making it perfect for storing a trailer or boat. Additional updates include a newer AC (2020), 200-amp electrical panel (2021), and water heater (2020). Grab the sunscreen and hit the beaches, this home has an ideal location that can't be beat!

Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)

Listing Agent: Jessica Macmichael (727-871-2638)

Remarks: Lake Conley Mobile Home Park welcomes you into this gated home in Desirable 55+ community. This tastefully meticulously well kept home is ready for you with all furnishings provided. You enter through a coded secure gate while enjoying the private lake view, wild bird life and tranquil community. There is so much to enjoy!! You have fishing, boating, golf cart riding, club house with great social life gatherings, serene heated pool area, shuffleboard, community dock and boat ramp, and optional boat/RV storage (subject to availability for a fee)—all for a super low monthly fee. As you enter, you will appreciate this cheerful light and bright new kitchen with all new stainless steel appliances and all new soft close kitchen cabinetry along with new flooring throughout the home. You have a separate dining area and large comforting living room with a closed in front porch attached where you can enjoy morning coffee or evening cocktails surrounded by windows throughout. The primary bedroom has its own full bathroom and walk-in closet. The 2nd bedroom has a walk in closet as well with the guest bathroom nearby. The laundry is in the attached shed with plenty of room for storage. 2025 vapor barrier replaced. 2025 roof was recoated for preventative maintenance only. 2018 AC 3 ton heat pump replaced by previous owner with 10 year parts warranty. There is plenty of covered parking space for your vehicle and golf cart. You Own the Land, with no lot rent, low taxes, as well as HOA Fees approx. $63.41 a month. Pet-friendly park will allow with one dog or one cat no more than 25lbs. Conveniently located near the famous Tarpon Springs Sponge Docks and Fabulous Downtown New Port Richey that is full of entertainment, just 45 minutes to Tampa International Airport/St Pete/Clearwater airport and 45 minutes to world famous Clearwater Beach! Easy show, come see this Florida lifestyle.

Listing is courtesy of: PARADISE WEST REALTY, INC (727-863-4567)

Listing Agent: Linda Saunders (727-967-1204)

Remarks: Discover your Florida retreat in the heart of Holiday Lake Estates! This beautifully refreshed 4-bedroom, 1.5-bath home with NO HOA invites you to experience laid-back living, walking distance to Tarpon Springs’ quaint shops, waterfront dining, and sandy shores. Step inside to all-new vinyl flooring (2025) throughout. The kitchen dazzles with fresh 2025 cabinetry, sleek granite counters, and stainless appliances—perfect for hosting friends or whipping up seaside snacks. The split-plan design includes a bedroom with direct access to a private backyard patio, creating flexibility for family, guests, or office space. Recent upgrades ensure peace of mind: roof, HVAC, and insulated windows (2017); updated electrical (2018); and a fully remodeled bathroom (2017). A fenced yard, double driveway, and attached garage + bonus half bath deliver both functionality and comfort. Just a short drive to beaches, marinas, and local hotspots—this home blends convenience with coastal charm. Whether you're looking for a primary residence, an investment opportunity, or a rental-ready gem, this move-in ready block home offers versatility and value.

Listing is courtesy of: COLDWELL BANKER REALTY (813-253-2444)

Listing Agent: Nicole Alexiou (727-265-0324)

Remarks: Welcome to this beautifully updated 2 bedroom, 1-bathroom, single-family home, offering both comfort and versatility! A thoughtfully designed bonus room can serve as an additional bedroom, home office, or extra living space to fit your needs. Step inside to find a stunningly renovated kitchen featuring stainless steel appliances, modern finishes, and ample storage. The stylishly updated bathroom complements the home's contemporary feel. Enjoy outdoor living with a covered front patio and an extended back patio, perfect for entertaining or simply unwinding in the serene surroundings. The sprawling backyard, nearly half an acre, extends to the pond behind the home, providing a peaceful waterfront setting. Additional highlights include a security system for peace of mind and solar panels for energy efficiency. Located just minutes from Anclote Park & Boat Ramp, Anclote Gulf Park, and Key Vista Nature Park, this home offers convenient access to outdoor recreation, boating and nature trails. Don't miss out on this unique property - Schedule your showing today!

Listing is courtesy of: ENGEL & VOLKERS MADEIRA BEACH (727-394-7365)

Listing Agent: Kate Glassell (727-424-4525)

Remarks: The highlight of this property is the Mother-in-Law Suite, making it ideal for multi-generational living or as an income-producing rental. This beautifully updated home offers the perfect balance of relaxation, convenience, and income potential. Just 10 minutes from a nature preserve filled with trails, sea life, birds, and beaches, and only 20–30 minutes from Florida’s most stunning sandy beaches, you’ll feel like you’re on vacation all year long. Surrounded by charming small towns with unique shops, restaurants, breweries, and vibrant nightlife, this home puts you in the heart of it all. Inside, everything is completely updated—move-in ready with no work required. Enjoy your home without the hassle of renovations. The fenced backyard offers plenty of space for a large pool, outdoor entertaining, and creating your own private retreat. The highlight of this property is the Mother-in-Law Suite, making it ideal for multi-generational living or as an income-producing rental opportunity.

Listing is courtesy of: HOME PRIME REALTY LLC (813-497-4441)

Listing Agent: Joneisy Diaz Ramirez (305-878-0210)

Remarks: Stunning Ocean views from this waterfront paradise. The opportunity has arisen to acquire the former home of the renowned local artist Elaine Hahn and AIA emeritus architect Byron G McIntyre. Located in the sought-after Bailey’s Bluff community, this stunning 4-bedroom, 4-bath elevated home offers 3,412 square feet of coastal living with panoramic water views throughout and 160 feet of private water frontage with direct access to the Gulf. Located at the very end of a Cul-de-sac the private driveway leads to a spacious 4 plus vehicle garage. Take the inside elevator to the open plan 2nd floor, with feature light maple hardwood flooring accentuating the amazing natural light that flows into the living room. This floor also contains an open-plan kitchen, dining area, master bedroom suite and artist studio which has the most amazing views you will find for any home office. There is a covered front balcony and wrap around back balcony where you can enjoy the wonderful Gulf breezes. The third floor has three further bedrooms and addition Den/office. Also, you will find a secluded third-floor balcony that looks out at more spectacular views across to Anclote Key. In addition to the ground level garage, there is a covered parking area. Inside the garage is workshop space with French doors onto the pool deck. The backyard has a tranquil, tropical and beach feel with floating dock and boat lift. Take a 15-minute stroll to Key Vista Nature Park with its many trails and observation tower overlooking the Gulf. Enjoy boating, fishing, scalloping and island hopping. A short drive to a recreational complex, parks, beaches and the charming community of Tarpon Springs, complete with shopping and dining options. This home is solidly built to withstand hurricanes, being elevated, and with concertina or roll down shutters to all windows. During 2024 storms only suffered minor damage, not even losing power. There is no HOA, but an optional Baileys Bluff Civic Assoc. membership is just $100 a year, providing a private beach, boat ramp, & clubhouse. Don't miss the opportunity to make this slice of paradise your own!

Listing is courtesy of: BANNER INT'L REAL ESTATE (407-574-5741)

Listing Agent: Nick Horton (407-733-7197)

Remarks: One or more photo(s) has been virtually staged. Discover unparalleled Gulf Front living in this stunning custom-built home with breathtaking OPEN 75’ Gulf front views and sunsets from multiple vantage points! This home features a BRAND NEW DOCK AND SEAWALL and with 3 bedrooms, 2.5 bathrooms, and a 2-car garage, this newly constructed home offers the perfect blend of luxury and modern convenience!! This home is a rare find offering the best waterfront living with high end finishes and thoughtful design including a fully equipped gourmet kitchen with new, elegant quartz countertops and backsplash, center island with pendulum lighting and farmer’s sink, new induction cooktop, new stainless steel double oven, sleek stainless steel hood vent and walk in pantry with custom shelving, family room with coffered ceilings and recess lighting perfect for entertaining, formal dining with coffered ceiling, new Luxury Vinyl floors and quad sliders leading you the oversized, raised, paved new patio and to the elongated NEW dock with a newer 7500lb boat lift! Wondrous master suite with astounding water views and walk in closets, exquisite master bath with Quartz countertops, pearl nickel fixtures and vast walk in shower with rainmaker shower head, modern lighting and mirror, immense guest quarters offer the 1st guest room with a walk in closet and impeccable views with a jack-n-jill bath boasting Quartz countertops, tiled floors and walk in shower with pebble flooring accents and rainmaker shower head, third guest room with double closets and beautiful view, NEW Luxury high end flooring throughout and electrical shades for added convenience and comfort and more! Don’t miss your chance to own this piece of paradise!

Listing is courtesy of: M3 REAL ESTATE PROFESSIONALS LLC (813-601-4752)

Listing Agent: Marsha Paul (813-601-4752)