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Single Family Homes for Sale in Holiday, FL

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

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All Single Family Homes for Sale in Holiday, FL

$299,000
3 Beds ⋅ 2 Baths ⋅ Gulfwinds SubDv.
VERY MOTIVATED SELLER, BRING AN OFFER!! Experience the best of the Florida lifestyle in this spacious, low-maintenance villa just minutes from charming downtown Tarpon Springs. Offering 1,740 square feet of thoughtfully designed living space, this 3-bedroom, 2-bath residence with a versatile den/office delivers the comfort and functionality of a single-family home without the upkeep. The open-concept floor plan seamlessly connects the kitchen, dining, and living areas—creating the perfect setting for entertaining guests or enjoying relaxed evenings at home. The kitchen shines with 42-inch maple cabinetry, granite countertops, and generous prep space, providing both style and practicality. Retreat to the expansive primary suite featuring a spa-inspired ensuite bath with dual vanities, a soaking tub, walk-in shower, and a large walk-in closet. Additional highlights include a full-size laundry room with utility sink and built-in shelving, as well as a spacious two-car garage with plenty of room for vehicles, beach gear, or recreational equipment. Located within a beautifully maintained community, the HOA covers lawn care, exterior painting, internet, cable, and trash service—allowing you to fully enjoy the amenities, including a resort-style pool and recreation area. Situated in a no-flood zone and just 10 minutes from the iconic Sponge Docks, marinas, parks, and top-rated schools, bike trail connected to the Pinellas Trail. Whether you're searching for a full-time residence, seasonal retreat, or investment opportunity, this villa offers exceptional value and convenience. Schedule your private showing today and discover everything this vibrant community has to offer.

2334 Barracuda Court, Holiday
$199,000
2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.
Welcome to this charming 2-bedroom, 2-bath home located at 3425 Richboro Drive in Holiday, Florida. This well-maintained property offers comfortable living with a functional layout perfect for year-round residents or seasonal homeowners. Enjoy relaxing mornings and peaceful evenings in the enclosed screened lanai, providing the perfect indoor-outdoor space to unwind or entertain. The fully fenced backyard offers added privacy and plenty of room for pets, gardening, or outdoor gatherings. This home is a wonderful opportunity to enjoy Florida living at its best. Schedule your private showing today!

3425 Richboro Drive, Holiday
$575,000
5 Beds ⋅ 3 Baths ⋅ Key Vista Prcl 18 SubDv.
Welcome to this beautiful 5 bedroom 3 bathroom two-story home located in the highly desirable community of Key Vista. Upon entry you immediately feel welcome and at home with the large formal dining area and front living area with electric fireplace. The large kitchen boasts tall cabinetry and plenty of counter space with amazing views of the tree line that reflects along the waters edge. One bedroom with private bathroom is conveniently located on the first floor and four bedrooms are located on the second story with the large master bedroom with private bathroom also has an adjoining bonus room. Enjoy the privacy of no rear neighbors with breathtaking views of nature in your own backyard!!! Only minutes away from some of the most beautiful beaches and parks in Florida. Schedule your private showing today!!!

1914 Oswego Drive, Holiday
$825,000
3 Beds ⋅ 3 Baths ⋅ Baileys Bluff Estates SubDv.
Virtually Staged. Open access to the Gulf!! Experience elevated waterfront living in this elegant 3 bed/2 bath residence with a versatile bonus room, thoughtfully designed to blend architectural charm, refined finishes, and seamless indoor–outdoor flow, all in the sought after Baileys Bluff Estates! The generously sized secondary bedrooms offer ample closet space and share a beautifully appointed full bath with a tub/shower combination. A hallway linen closet with built-in shelving provides additional storage. The primary suite is a true retreat, featuring sliding-door access to the lanai and a spa-inspired bath complete with a step-in shower with sliding glass doors—also opening to the exterior—dual-sink vanity, private water closet, and a dedicated dressing hallway with abundant closet space. A separate pool-access bath with sink and toilet can be closed off from the primary suite for added privacy. A nearby washer and dryer closet enhances everyday convenience. The main living areas impress with soaring volume ceilings, recessed lighting, and a striking corner stone fireplace anchoring the space. The chef’s kitchen is as functional as it is beautiful, showcasing wood soft-close cabinetry, granite countertops, stainless steel appliances, a breakfast bar, pantry closets with extensive shelving, a built-in corner desk, and a sun-filled breakfast nook. Architectural details add warmth and character, including a barn-style sliding door allowing the kitchen to be closed off when desired, and a decorative wicker-accent opening that enhances the home’s charm. A flexible dining area offers the option of formal dining and opens through sliding doors to a charming brick patio. The bonus room provides exceptional flexibility—ideal as a home office, media room, or optional fourth bedroom—complete with a utility sink closet, additional storage, and direct garage access. Outdoors, the expansive screened-in lanai and pool create a private oasis perfect for entertaining, complemented by an outdoor shower. The generous fenced backyard leads to your waterfront dock area, where tranquil water views can be enjoyed from the living room, breakfast nook, dining area, and kitchen. Additional highlights include light wood luxury vinyl flooring throughout; tile flooring in all bathrooms, oversized windows providing abundant natural light, ample storage throughout, and an oversized two-car garage. Located just two blocks from the Coastal Anclote Trail, which offers over four miles of scenic paths that connect to the Pinellas Trail in Tarpon Springs. Enjoy easy water access via the bayou and creek with just a five-minute boat ride to the Gulf. The area is also ideal for kayaking. Pickleball courts with weekly league play are located within one mile. This exceptional waterfront property offers the perfect blend of lifestyle, comfort, and convenience. Schedule your private showing today.

2138 Bayou Drive, Holiday
$329,980
3 Beds ⋅ 2 Baths ⋅ Gulfwinds SubDv.
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!

2302 Barracuda Court, Holiday
$229,900
2 Beds ⋅ 2 Baths ⋅ Holiday Lake Estates SubDv.
Don’t miss this charming 2-bedroom, 2-bath solid block and stucco home featuring a separate Florida room plus a spacious bonus room that can easily be converted into a third bedroom and includes a wood-burning fireplace. The garage has been converted into a large bonus space, offering excellent flexibility for a home office, guest suite, or additional living area. Recent updates include a newer roof and water heater, providing peace of mind for years to come. You’ll love the expansive fenced backyard with plenty of room to store a boat or RV, along with a storage shed for lawn equipment. Situated on a nice-sized corner lot, this property offers both space and functionality. Located in a non-flood zone with no flood insurance required, the home is just minutes from the beaches, shopping, dining, marinas, and vibrant nightlife. Priced to sell, this move-in-ready home is perfect for first-time buyers, those looking to downsize, or anyone seeking a vacation or second home. Schedule your showing today—you’ll be glad you did.

3208 Kilburn Road, Holiday
$289,000
2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.
Welcome to this charming two bedroom, two bath home with a spacious Florida room that offers beautiful water views. The semi-open floor plan features updated kitchen counters, and fresh paint, along with new flooring installed after last year’s storms. Enjoy the serene water view complemented by a mature tree in the backyard, perfect for fishing and budget friendly lifestyle. The home has been lightly used over the past five years, ensuring it’s in great condition. The second bedroom features its own bathroom, and there’s a separate dining room plus a large living room area. Don’t miss out on this wonderful opportunity!New refrigerator, fresh paint, new flooring throughout the house, new kitchen countertops as of 2023. New 3 ton AC unit installed in 2024 and new electrical panel in 2021. New Water Heater 2026.

3228 Rock Valley Drive, Holiday
$410,000
3 Beds ⋅ 2 Baths ⋅ Key Vista Ph 4 SubDv.
LENDER PAID 1% BUY DOWN WITH PREFERRED LENDER FOR INITIAL 12 MONTHS OF MORTGAGE PAYMENTS. Totally renovated 3bedroom 2 bathroom 2 car garage home in quiet community. Roof, HVAC,Water Heater, Flooring, Kitchen and Bathrooms all brand new.Wood cabinets and stone counter tops in Kitchen and Bathrooms. Huge lot with vaulted screened in lanai. Low HOA covers community pool and cable. Come and make this charmer your new home!!!

2700 Sierra Vista Way, Holiday
$216,000
2 Beds ⋅ 1 Baths ⋅ Holiday Gardens SubDv.
Quintessential Florida Living in Holiday! Welcome to this charming 2-bedroom, 1-bath, 1-car garage Florida home offering 1,200 sq ft of bright and inviting living space in the heart of Holiday, FL. From the moment you step inside, you’ll appreciate the beautiful white terrazzo floors and the abundance of natural light streaming through the many windows. The original kitchen and bathroom have been impeccably maintained, showcasing timeless character and pride of ownership. The eat-in kitchen opens to the living room and features a convenient breakfast bar, making it perfect for casual meals and entertaining. A formal dining area open to the family room provides flexible space for gatherings and everyday living. Step outside to enjoy a private, fully fenced backyard with a covered patio—ideal for relaxing, hosting barbecues, or soaking up the Florida lifestyle. Major updates include a new 2026 water heater & utility sink, 2018 newer roof & A/C, offering peace of mind for years to come. Best of all, this home is located in a non-flood zone, with no HOA or CDD fees. Easy access to beaches, shopping, and dining, this property is perfectly situated for both convenience and coastal enjoyment. Whether you’re a first-time buyer, downsizing, or looking for a beach-close retreat, this home is a must-see!

2128 Shannon Drive, Holiday
$244,900
3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv.
Located in a fantastic area of Holiday with its close proximity to Pinellas County, this three-bedroom, two-bathroom home is nicely updated and completely turn-key! New laminate flooring was just installed throughout the home ready for the new owners. The fully updated galley kitchen features level 2 granite, a full array of modern stainless-steel appliances and a breakfast nook area overlooking the backyard. The bonus room opens up even more possibilities for the indoor space and leads into the screened-in lanai and the fully fenced back yard complete with newly resealed pavers and a built-in firepit. The nicely updated bathrooms feature newer vanities and exquisite tile work. Part of the garage was converted into the 3rd bedroom but can easily be put back if a buyer so chooses. The roof and AC are newer as well, and the windows have been updated with modern double-pane impact windows. There is plenty of space for parking on the driveway, plus a storage bay garage. The laundry room is within the home and unlike other listings, the washer and dryer are INCLUDED. This home is clean, inviting and situated in an area close to parks, beaches, shopping, medical facilities and all the best that Florida has to offer. Make your appointment today!

1148 Fernwood Drive, Holiday
$304,900
3 Beds ⋅ 2 Baths ⋅ Gulfwinds SubDv.
Freshly painted and ready for a new owner! This bright, private, and easy to enjoy 3-bedroom, 2-bath Gulfwinds villa offers 1,740 square feet of single-story living with a screened lanai, fully fenced backyard, extended brick-paver patio, and two-car garage. Inside, vaulted ceilings, three solar tube skylights, and engineered hardwood flooring create an open, light-filled main living space. The split-bedroom layout keeps the primary suite tucked away from the guest bedrooms, offering flexibility for guests, a home office, or everyday living. The outdoor space is where this home really stands out. Enjoy a screened lanai that opens to a private fenced backyard and extended paver patio—ideal for relaxing, entertaining, grilling, or simply enjoying Florida’s year-round weather. Major updates include HVAC in 2019, water heater in 2022, whole-house surge protection in 2022, and an included water softener. Hurricane shutters/windows provide added peace of mind. Gulfwinds offers low-maintenance living with HOA-covered lawn care, exterior painting, cable, internet, roof maintenance, and community pool access. Roof replacement is planned through the HOA for 2027. Located in Flood Zone X and minutes from Tarpon Springs, the Sponge Docks, Anclote River Park, marinas, beaches, shopping, dining, and medical facilities. Schedule your private showing today.

2153 Barracuda Court, Holiday
$278,900
3 Beds ⋅ 2 Baths ⋅ Holiday Lake Estates SubDv.
GREAT HOME FOR THE GROWING FAMILY. LARGER THAN NORMAL BEDROOMS, PLENTY OF CLOSET SPACE. LIGHT AND BRIGHT UPGRADED KITCHEN WITH GRANITE COUNTERS INCLUDING A FAMILY ROOM KITCHEN COMBO. EVEN A WINDOW AT SINK TO LOOK OUTSIDE. LARGE LIVING ROOM WITH A LARGE WINDOW FOR LIGHTING. OUTDOOR COVERED PATIO AREA FOR A PARTY AND NEXT TO THAT IS A EXTRA OUTDOOR KITCHEN AREA. YOU WILL FEEL AT HOME HERE. SINGLE CAR GARAGE FOR YOUR OR STORAGE. WASHER/DRYER HOOK UPS. UP GRADED ELECTRICAL PANEL AND WATER HEATER. NO FLOOD INSURANCE HERE.

1324 Viking Drive, Holiday
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