Homes for Sale with a Pool in Holiday, FL

Welcome to this 4-bedroom, 2-bath, solar-powered, pool home offering plenty of comfortable living space on the water. The property also features its own dock right in the backyard, providing direct access to Lake Conley. Inside, the home offers a bright, open feel with abundant natural light, a neutral color palette, and luxury vinyl plank flooring throughout the living areas. The kitchen is equipped with stainless steel appliances and a convenient pass-through with bar seating, ideal for everyday living and entertaining. Major updates include a 2019 roof and 2019 HVAC, offering peace of mind for years to come. The property also did not experience flooding during recent storms. Garage is currently in the process of being converted into a mother-in-law suite with a separate entrance. Step outside to be greeted by the sparkling pool in a screened lanai, a relaxing space to enjoy the Florida lifestyle year-round. The pool also features a safety fence for peace of mind. Located just minutes from local beaches, parks, shopping, and dining, this home offers a perfect balance of everything that makes living in Florida wonderful.

3022 Jackson Drive, Holiday

$133,000

2 Beds ⋅ 2 Baths ⋅ Tanglewood Mobile Village SubDv.

Price improvement. Motivated sellers! Stop and check out this well-maintained home in a very active 55+ community. Home is furnished with 2 bedrooms, 2 bathrooms, finished Florida room with separate a/c. Central heat and air-conditioning NEW in 2022, NEW Refrigerator, NEW dryer, enclosed and screen lanai. Windows have been replaced; seller is not sure of year of replacement. Low monthly maintenance fee of $143.00 includes lawn service, garbage removal, maintenance of year-around-heated pool, Clubhouse, Shuffleboard and the common areas. You OWN YOUR LAND. Measurements are approx. Buyer to verify all information that is deemed to be accurate.

4809 Empress Lane, Holiday

1804 Rising Sun Drive Unit 1804, Holiday

$155,000

2 Beds ⋅ 2 Baths ⋅ Sunrise Square Villas SubDv.

Welcome to this 55+ community of Sunrise Square Villas! Check out this clean updated 2-bedroom, 2-bath condo that includes a 1 car carport. This condo features newer appliances, solid wood kitchen cabinets, a newer tankless hot water heater, a split floor plan and a relaxing Florida room. The living/dining room area has vaulted ceilings. Excellent location that is close to beaches, parks, Tarpon Springs Sponge Docks, shopping and much more. Don't miss this wonderful property!!!

1804 Rising Sun Drive Unit 1804, Holiday

$625,000

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

$775,000

4 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

$134,900

2 Beds ⋅ 2 Baths ⋅ Tanglewood Mobile Village SubDv.

Price improvement! 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.

3141 Nantucket Drive, Holiday

$89,900

2 Beds ⋅ 2 Baths ⋅ Tanglewood Mobile Village SubDv.

Looking for a winter get-away, don't want to deal with moving all your furnishing? Then see this move-in-ready fully furnished home, right down to housewares. Owned by one family since construction. Why would you rent a lot elsewhere if you could OWN YOUR LAND in Tanglewood Mobile Village? Perfect as a Florida vacation home or a year-round residence in a very active 55+ community with year-round heated pool, low monthly HOA ($143.00) that provides lawn care, trash removal, clubhouse, shuffleboard, and many community activities. No Rentals are allowed, so the community stays private and settled. Features two bedrooms, two baths (one having a walk-in shower) combination of laminate floors, and carpeting, kitchen with eat-in area. Hookup for a stackable washer and dryer in larger bedroom. New water heater. screened in lanai with vinyl windows, carport with storage shed, patio area behind shed. Sold-as-is Buyers to verify all information that is deemed to be accurate. Measurements are approx.

3405 Lanark Drive, Holiday

$410,000

3 Beds ⋅ 2 Baths ⋅ Key Vista Ph 4 SubDv.

Virtually Staged. LENDER PAID 1% BUY DOWN WITH PREFERRED LENDER FOR INITIAL 24 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

$295,000

3 Beds ⋅ 2 Baths ⋅ Gulfwinds SubDv.

NEW PRICE — $295,000! FRESHLY PAINTED INTERIOR + LENDER-PAID 1-0 INTEREST RATE BUYDOWN AVAILABLE! Enjoy the space and comfort of a single-family home with the convenience of low-maintenance villa living! Located in the desirable GULFWINDS community, this beautifully maintained 3-bedroom, 2-bath villa offers 1,740 square feet of living space, a 2-CAR GARAGE, and a private fenced backyard with an extended brick paver patio. Step inside to discover a bright, spacious OPEN FLOOR PLAN featuring HIGH CEILINGS, FRESH INTERIOR PAINT, and ENGINEERED HARDWOOD FLOORING throughout the main living areas and bedrooms. Three solar tubes bring additional natural light into the home, creating a warm and inviting atmosphere. The kitchen features wood cabinetry, stainless steel appliances, generous counter space, and a breakfast bar overlooking the dining and living areas. The desirable SPLIT-BEDROOM FLOOR PLAN provides privacy and flexibility. The spacious primary suite features a walk-in closet and an en-suite bathroom with dual vanities, a soaking tub, and a separate shower. Two additional bedrooms provide plenty of room for guests, a home office, or hobbies. YOUR OWN PRIVATE OUTDOOR RETREAT! Sliding glass doors lead to a covered, screened lanai overlooking the FENCED BACKYARD and EXTENDED BRICK PAVER PATIO. Whether enjoying morning coffee, entertaining friends, or simply relaxing outdoors, this inviting space is perfect for enjoying Florida living year-round. Additional highlights include HURRICANE SHUTTERS, a WHOLE-HOUSE SURGE PROTECTOR, HVAC replaced in 2019, and a water heater replaced in 2022. LOW-MAINTENANCE LIVING WITH EXCEPTIONAL HOA BENEFITS! Gulfwinds offers a community swimming pool, sidewalks, scenic ponds, and beautifully maintained common areas. The monthly HOA includes LAWN MAINTENANCE, EXTERIOR PAINTING, ROOF MAINTENANCE/REPLACEMENT, CABLE TV, and INTERNET SERVICE. The HOA currently anticipates roof replacement in early 2027; buyers should verify the schedule and details with the association. ENJOY THE GULF COAST LIFESTYLE! Conveniently located near ANCLOTE RIVER PARK, featuring a sandy beach, boat ramps, fishing, and waterfront views. Explore KEY VISTA NATURE PARK and the COASTAL ANCLOTE TRAIL for walking, biking, and outdoor recreation. Just a short drive away, the historic TARPON SPRINGS SPONGE DOCKS offer waterfront dining, authentic Greek cuisine, shopping, and sightseeing cruises. Beaches, parks, restaurants, shopping, and everyday conveniences are all within easy reach. SPECIAL BUYER FINANCING INCENTIVE! A LENDER-PAID 1-0 TEMPORARY INTEREST RATE BUYDOWN is available for qualified buyers through a participating lender! This program reduces the buyer’s interest rate by 1 percentage point during the first year of the loan, with the note rate applying thereafter. Subject to lender approval, loan program eligibility, and applicable terms. Whether you’re searching for a full-time residence, seasonal Florida getaway, or a spacious home with less exterior maintenance, this villa offers an exceptional opportunity. FRESHLY PAINTED, ATTRACTIVELY PRICED AT $295,000, AND READY FOR ITS NEXT OWNER! SCHEDULE YOUR PRIVATE SHOWING TODAY!

2153 Barracuda Court, Holiday

$275,000

2 Beds ⋅ 2 Baths ⋅ Key Vista Ph 02 SubDv.

Welcome to one of Holiday’s most sought after 55+ gated communities, where privacy, comfort, and an active Florida lifestyle come together seamlessly. This beautifully maintained 2 bedroom, 2 bath home in Key Vista offers 1,555 square feet of well designed living space, along with a versatile office/flex room that can easily serve as a third bedroom, hobby room, or dedicated workspace. Situated on a rare homesite with no neighbor to the right or behind, this property provides exceptional privacy and tranquility. Inside, you’ll find an inviting open floor plan filled with natural light and thoughtfully designed for everyday living and effortless entertaining. The spacious kitchen is a highlight, featuring a large island, breakfast bar, pantry, and plenty of cabinetry ideal for meal prep, gatherings, and morning coffee. The oversized living and dining areas provide flexible layout options and a warm, welcoming feel. A screened-in lanai extends your living space outdoors, perfect for relaxing, dining al fresco, or unwinding while enjoying Florida’s calming breezes. The primary suite offers comfort and functionality with ample closet space and an ensuite bath. The guest bedroom and bath are equally inviting, offering privacy for visitors. Additional features include an attached two-car garage and dedicated laundry area. Residents enjoy low HOA fees, no CDD, and access to two clubhouses. One exclusively for 55+ residents with a private pool, plus a master clubhouse with a pool, spa, gym, tennis and pickleball courts, sand volleyball, playground, and more. On site RV and boat storage is also available for a small monthly fee. If you're looking to venture outside of the community there is nearby Key Vista Nature Park. Enjoy incredible sunsets or walk through one of the many nature trails to enjoy everything Gulf Coast living. This home is also close to parks, shopping, dining, and Gulf beaches. Everyday conveniences are also close at hand. This Holiday gem blends privacy, space, and resort-style amenities in an unbeatable location. Schedule your private tour today!

2453 Pleasant Hill Lane, Holiday

$100,000

2 Beds ⋅ 2 Baths ⋅ Tanglewood Mobile Village SubDv.

Price Improvement. Come and enjoy all the activities offered in this well-maintained 55+ Community with a low monthly maintenance fee of $143.00 a month which is includes lawn maintenance, garbage service, maintenance of clubhouse and year-around heated pool. Home features new roof 2025, newer air/heat system, 2 bedrooms, 2 baths, screen lanai, finished and enclosed front porch. Home is unfurnished, No Refrigerator. YOU OWN YOUR OWN LAND! This is an estate property, Sellers have never lived in home, Sellers disclosure is all the knowledge they know. Measurements are approx. Sold As Is. Buyer to verify all information that is deemed to be accurate.

3211 Lanark Drive, Holiday

Homes for Sale with a Pool in Holiday, FL

All Homes for Sale with a Pool in Holiday, FL

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