Waterfront Homes for Sale in Holiday, FL

1 Beds ⋅ 1 Baths ⋅ Holiday Lake Villas Condo SubDv.

Virtually Staged. Clean, updated and move-in ready single story villa with no stairs to entry, non flood zone (X), and LOW HOA of $412/mo more than pays for itself! Welcome home to total ease and true maintenance-free Florida living at 3806 Staysail Ln, a beautifully updated, spacious single-story block construction villa in a peaceful 55+ community with no stairs to entry and no unit or neighbors above! Located in a non-flood zone, this home offers added peace of mind before you even step inside. This move-in ready villa has been thoughtfully updated with fresh interior paint, new waterproof LVP flooring throughout, updated AC and newer water heater, while the HOA takes care of the exterior maintenance so you can spend more time enjoying life. A reserved covered carport (#3806) is conveniently located directly in front of the villa, with plenty of guest parking available nearby. Large windows fill the home with natural light, creating an inviting atmosphere throughout. The thoughtfully designed floor plan offers room for a full living room set, an eat-in kitchen with newer cabinetry, clean appliances, and bar stool seating at the counter, plus a separate walk-in utility room and an additional outdoor storage room so you'll never run out of space. The washer and dryer are already installed and convey with the home. Unwind in your enclosed Florida room or lanai, open the windows to enjoy the gentle breeze, and take in tranquil pond and fountain views while watching duck families, blue herons, and other birds gather near the water. The oversized primary bedroom features a large walk-in closet, while the spacious bathroom offers a step-in tile shower and plenty of room to navigate comfortably. The low $412/month HOA fee covers water, sewer, trash, cable, internet, roof, exterior building maintenance, exterior painting, lawn and grounds care, and pest control. Outside your door, you can walk to the active clubhouse for card games, bingo, community BBQs, reserve the space for hosting large family gatherings, enjoy the community pool year-round, play shuffleboard, or take a peaceful stroll around the beautifully maintained neighborhood. Conveniently located just minutes from the world-famous Tarpon Springs Sponge Docks, beautiful Gulf beaches, shopping, dining, medical facilities, and everyday conveniences, you'll enjoy the perfect balance of peaceful living and an unbeatable Florida lifestyle. Opportunities to own a beautifully updated, single-story pond view villa in this community don't come along often. Two small pets are welcome, making this the perfect place to enjoy easy, maintenance-free Florida living.

3806 Staysail Lane, Holiday

$239,900

3 Beds ⋅ 3 Baths ⋅ Aloha Gardens SubDv.

Waterfront Fixer-Upper with Incredible Potential! Calling all investors, flippers, and renovation enthusiasts! This 3-bedroom, 3-bath waterfront property sits on a large lot and is packed with opportunity. Whether you're looking to renovate, rebuild, or create your dream waterfront retreat, the possibilities are endless. With a desirable waterfront location and plenty of space to work with, this is a rare chance to unlock significant value. Cash offers only. Don't miss this investment opportunity with outstanding potential!

4138 Star Island Drive, Holiday

$240,000

2 Beds ⋅ 2 Baths ⋅ Aloha Gardens SubDv.

Wake Up on the Water, Every Single Day, coffee in hand, mist rising off Lake Conley, and a great blue heron gliding past your own dock. This isn't a vacation. It's Tuesday morning at 2228 Society Dr. This 2-bedroom waterfront home sits directly on Lake Conley with access out to Lake Nash, and it comes with the kind of backyard most people only dream about: a seawall, a private dock, and water views from nearly every angle. Cast a line before breakfast. Launch the kayak after lunch. Watch the sunset turn the lake gold before dinner. And here's the part buyers keep asking about. Yes, this home stayed high and dry through the 2024 hurricanes when most waterfront properties did not, offering real peace of mind in a waterfront property. Inside, the home has been thoughtfully updated for easy, comfortable living. No major projects waiting for you, just move in and start enjoying the lake life. And with no HOA, no CDD fees, and a no-money-down purchase option for eligible buyers, this one opens doors that other waterfront listings simply can't. Location? You're minutes from Anclote River Park, Key Vista Nature Park, Fred Howard Beach, the Tarpon Springs Sponge Docks, and New Port Richey's Main Street dining scene. Hop on US-19 and you've got Tampa International Airport and Florida's famed white sand Gulf beaches, including Honeymoon Island, Caladesi Island, and Clearwater Beach, all within easy striking distance. True lakefront, no fees, flexible financing, is definitely one you should see in person. Schedule your private showing today and see why this is the lake life you've been waiting for.

2228 Society Drive, Holiday

$335,000

3 Beds ⋅ 2 Baths ⋅ Forest Hills SubDv.

Welcome to this spectacular waterfront property in the Forest Hills subdivision, a true tropical paradise and boater's dream offering direct Gulf access from your private dock and 10,000-pound boat lift. From the grand circular driveway and beautifully updated landscaping to the expansive wrap-around screened lanai, this ranch-style home is designed for seamless indoor-outdoor living against the backdrop of stunning Anclote River sunrises and sunsets. Inside, a spacious great room features elegant tile flooring, fresh paint, and insulated windows that flood the home with natural light, leading into a beautiful kitchen equipped with premium Bosch, Frigidaire, and Whirlpool appliances. The primary suite serves as a relaxing sanctuary with dual sliding closet doors, a dedicated mini-split AC, and dramatic floor-to-ceiling windows overlooking the water, while the secondary bedrooms offer incredible versatility, including a bonus space with a dry bar and mini-fridge ideal for a home office or gym. Both bathrooms have been completely renovated, featuring modern fixtures, a laundry closet with a premium LG washer and dryer, and a walk-in shower with a stylish glass backsplash and supportive grab bars. Outside, elegant pavers guide you to the private pier where you can catch snook and redfish right from the backyard, while the fenced green space provides a wonderful area for pets to roam. Complete with a converted garage perfect for a workshop and three storage sheds for outdoor gear, this one-of-a-kind riverfront retreat is entirely move-in ready and waiting for your watercraft.

1133 Grand Boulevard, Holiday

$509,000

2 Beds ⋅ 2 Baths ⋅ Baileys Bluff Estates SubDv.

NEVER FLOODED DURING HURRICANE HELENE! This is a rare opportunity to own a Gulf-access waterfront home that offers both an exceptional boating lifestyle and added peace of mind. According to the seller, the home has never experienced flooding or water intrusion, making it an outstanding choice for buyers seeking waterfront living with confidence. Nestled in the highly desirable Baileys Bluff Estates, this move-in-ready waterfront home sits on an oversized 0.31-acre lot with approximately 55 feet of saltwater canal frontage, offering direct Gulf access in about one minute. Bring your boat, kayaks, paddleboards, and fishing gear—your waterfront adventures begin right in your own backyard. Boaters will appreciate the private boat ramp, 10,000-pound boat lift, with, stationary dock, and concrete seawall, making launching and storing your boat effortless. Spend your days fishing, scalloping, island hopping to Anclote Key, or watching spectacular Gulf sunsets just minutes from home. Inside, you'll find an inviting floor plan featuring 2 bedrooms, 1.5 baths, an updated kitchen with solid wood cabinetry, updated bathrooms, comfortable living spaces, and a bright Florida room overlooking the tranquil canal. The home has been well maintained and is ready for its next owner. Major recent improvements provide outstanding value, including a brand-new roof (2025) and a brand-new air conditioning system, helping reduce future maintenance costs while increasing buyer confidence. The spacious backyard provides plenty of room to entertain, garden, or simply relax while enjoying peaceful waterfront views and abundant Florida wildlife. Located just minutes from Anclote River, the Gulf of Mexico, Key Vista Nature Park, the famous Tarpon Springs Sponge Docks, beaches, waterfront dining, shopping, and medical facilities, this home offers the perfect balance of recreation and convenience. Whether you're looking for a year-round residence, seasonal retreat, or waterfront investment, opportunities like this are becoming increasingly difficult to find. No HOA, Move-in ready. Schedule your private showing today and discover why this exceptional Gulf-access waterfront property is one of Holiday's best boating values.

3318 Pineview Drive, Holiday

$90,000

Tahitian Dev SubDv.

Discover the perfect setting for your custom waterfront dream home on this expansive .39-acre canal-front lot located on a quiet cul-de-sac in Holiday. Offering ample space for a variety of home designs, outdoor living areas, and landscaping possibilities, this oversized property provides a rare opportunity to create your ideal Florida retreat. An added bonus - the adjacent lot is also available for purchase, allowing for an even larger homesite or future investment potential. Enjoy peaceful canal views and a tranquil setting in an up-and-coming neighborhood with numerous newly constructed homes. According to the owner, the property has never flooded during past storms, providing additional confidence as you plan your future build. With the property line extending into the water, there is potential to add a private dock, creating the perfect spot for fishing, launching kayaks or paddleboards, enjoying nature, or simply relaxing by the water. Whether you're seeking a waterfront lifestyle or a unique homesite with room to grow, this property offers exceptional possibilities. Conveniently located near shopping centers, restaurants, parks, and zoned schools, the property is also just minutes from the J. Ben Harrill Recreation Complex. Historic Tarpon Springs, known for its waterfront dining, unique shops, festivals, and year-round activities, is only about 15 minutes away. Gulf beaches and endless outdoor recreation opportunities are also within easy reach. Don't miss this rare chance to secure a spacious waterfront lot in a growing area and build the home you've always envisioned.

1504 Jackson Drive, Holiday

$90,000

Tahitian Dev SubDv.

Rare opportunity to build your dream waterfront home on this expansive .27-acre canal-front lot located on a quiet cul-de-sac in Holiday. Offering beautiful canal views and a refreshing breeze, this property provides the ideal canvas for creating your custom Florida retreat. An added bonus - the adjacent lot is also available for purchase, creating the potential for an even larger homesite or investment opportunity. The property line extends into the water, presenting the possibility of adding a private dock and enjoying direct access to the canal. According to the owner, the lot has never flooded during past storms, offering additional peace of mind. Situated on an up-and-coming street, you'll find numerous newly constructed homes nearby, further enhancing the area's appeal. Conveniently located near shopping centers, restaurants, parks, and zoned schools, the property is also just minutes from the J. Ben Harrill Recreation Complex. Historic Tarpon Springs, known for its waterfront dining, sponge docks, local shops, festivals, and year-round activities, is approximately 15 minutes away. Gulf beaches, boating opportunities, and outdoor recreation are all within easy reach. Whether you're looking to build a primary residence, vacation getaway, or investment property, this waterfront lot offers location, potential, and a unique opportunity to enjoy the Florida lifestyle.

1503 Jackson Drive, Holiday

$3,750,000

Tampa Tarpon Spgs Land Co SubDv.

ISLAND READY FOR DEVELOPMENT - 6.4 Acres- Approved for 87 units, multi- family, ENTITLEMENTS GRANTED, PASCO COUNTY. LOCATED ON BERRY HILL ROAD, HOLIDAY, FL, East of Grand Blvd. Parcel ID 29-26-16-0000-00500-0050 FOREST HILL EAST DEVELOPMENT designated and approved for 87 multiple-family apartment units, waterfront, adjacent to the Anclote River with Gulf access. A rare multifamily development opportunity on a private 6.45-acre island surrounded by water, proposed 87-unit luxury apartment community... Designed as a three-story mid-rise development totaling approximately 96,842 SF, the project features modern construction, water-view patios and balconies, covered entrances, assigned parking and storage, elevators, and a resort-inspired amenity package.... Planned community features include a clubhouse with exercise room, kitchenette, conference room, and office, pool, tiki bar, pavilion, and BBQ area.... Including fishing, kayaking, canoeing, and direct access to the Anclote River with routes to the open Gulf waters and Tarpon Springs.... The property blends privacy, recreation, and upscale design into a truly unique rental concept surrounded by natural beauty. Floor plans, renderings, and site plans available.... Its proximity to Pinellas County, one of Florida's most densely populated counties, enhances its appeal for residential, mixed-use, or investment potential. A rare chance to capitalize on the continued growth and demand along Florida's Gulf Coast.

Berry Hill Road, Holiday

$799,000

Total of 1.4675 acres, 2 parcels of land. Owner will not sell properties individually. Nestled on the shimmering Anclote River in prime territory in Holiday, Florida. Situated on a waterway that leads out to the Gulf. Located on a coveted cul-de-sac, 200 feet of water frontage is retained by an existing seawall and encircled by trees for privacy. The property has direct views of a conservation island. ALL utilities including city water, power, and sewer are present. A myriad of possibilities are available including subdividing the land into three individual lots (each .48 acres) or retaining the parcel to accommodate a large, single-family home. Zoning permits a SFH structure or a duplex on each lot; one per lot if so desired. For investors or individuals, this prospect offers true flexibility and the chance to acquire a rare stretch in a market hungry for property to support new construction in well-positioned Pasco County. Minutes from: the sparkling Gulf, the culinary delights found in Tarpon Springs, all the retail you need on US Highway 19, and the multi-faceted Anclote River Park offering kayak/fishing access, picnic area, playground, 24/7 boat ramps, recreational courts and more! This nuanced investment suits numerous objectives. Buyer to verify all dimensions, lot sizes, zoning, permitting, leasing restrictions etc.

Flotilla, Holiday

$160,000

2 Beds ⋅ 2 Baths ⋅ Holiday Lake Villas Condo SubDv.

Welcome to this well-maintained 2 bedroom, 2 bath condominium in the coastal community of Holiday, offering comfort, convenience, and peaceful living along Florida’s Gulf Coast. Flood insurance is not required because located in zone X500. This single-level home features a functional kitchen with appliances and ample counter space, flowing into comfortable living areas designed for easy everyday living. Major updates include a 2020 HVAC system, 2021 hot water heater, and hurricane-impact windows for added peace of mind and efficiency. Two standout features of this unit is its prime setting overlooking a tranquil lake, offering relaxing water views and added privacy. Unlike other units in the community that back to a busy road or have upstairs neighbors, this single-story layout provides a quieter, more desirable living experience with no one above you. Second, there are guest spots easily accessible along with a carport for the owner to park just outside the front door! This Condo is 1,318 SqFT, but if you add in the Florida Room’s SqFT you have 1,542 SqFT of Entertainment Space making the price point of this unit a RARITY! The purchase of the home includes all furnishings and household items, making it truly move-in ready and ideal as a primary residence, seasonal retreat, or investment property. Residents enjoy nearby access to beautiful outdoor destinations such as Anclote River Park and the stunning beaches of Anclote Key Preserve State Park, as well as the charming waterfront dining and cultural experiences in Tarpon Springs. With its combination of updates, furnishings, lake views, and desirable layout, this condo offers an exceptional opportunity to enjoy relaxed Florida living at its best.

3801 Sailmaker Lane, Holiday

$235,000

2 Beds ⋅ 2 Baths ⋅ Beacon Square SubDv.

Don’t miss this beautifully updated corner-lot home with serene pond views. Featuring a newer roof (2022) and a new HVAC system (2023), this property offers peace of mind along with modern upgrades throughout. Inside, the home has been fully remodeled with a brand-new kitchen, updated bathrooms, and all-new flooring. The layout includes two spacious bedrooms and two full bathrooms, along with multiple living spaces—perfect for both relaxing and entertaining. Enjoy a welcoming living room, a separate family room, and a large Florida room that provides additional space to unwind while taking in the peaceful surroundings. Additional highlights include a one-car garage and a desirable corner location that enhances both privacy and curb appeal.

3507 Landale Drive, Holiday

$210,000

2 Beds ⋅ 1 Baths ⋅ Tahitian Dev Sub SubDv.

Welcome to waterfront living on beautiful Lake Conley! This well-maintained 2-bedroom, 1-bathroom single-family home offers a comfortable, move-in-ready retreat in the coastal community of Holiday. Situated directly on Lake Conley, the home features a desirable north-facing orientation and a solid concrete seawall that provides a peaceful waterfront setting to enjoy right from your own property. Inside, the kitchen offers stainless steel appliances and granite countertops, combining style and functionality for everyday living and entertaining. Adding even more value and peace of mind, a new roof and new HVAC system will be installed prior to closing, giving the next owner two significant home improvements from day one. The property is also connected to municipal water and sewer—NO SEPTIC system to maintain. Beyond the waterfront lifestyle at home, you'll be just minutes from Anclote River Park for boating, fishing, and Gulf sunsets, with easy access to Anclote Key Preserve State Park and the beaches of the Gulf. Shopping, dining, and the distinctive restaurants, waterfront, and culture of Tarpon Springs are also just a short drive away. With Lake Conley waterfrontage, municipal water and sewer, a new roof, new HVAC, and a convenient coastal location, this home offers an appealing combination of lifestyle, value, and low-maintenance Florida living. I’d recommend leading with the **Lake Conley waterfront** rather than simply calling it a “waterfront home.” Naming the lake makes the feature more tangible and differentiates the property in MLS searches and buyer marketing.

3510 Wilson Drive, Holiday

Waterfront Homes for Sale in Holiday, FL

All Waterfront Homes for Sale in Holiday, FL

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