Remarks: Turnkey beachside investment opportunity with sought after zoning that allows for nightly vacation rentals. Located literally just steps from the powder white sands of the Gulf, this fully furnished 2 bedroom plus loft, 2 bath coastal retreat is ideally positioned for both strong rental performance and personal enjoyment. A brick paver walkway leads to the home’s welcoming front patio, which is surrounded by charming landscaping. Adirondack seating and a firepit create the perfect setting to relax and unwind after a day at the beach, setting the tone for the coastal lifestyle this property offers. A spacious storage shed keeps all your beach gear and toys organized, and an outdoor shower adds convenience after enjoying the sand and surf. Upon entry, the first floor features the kitchen and dining area, complete with white shaker cabinetry, quartz countertops, GE stainless steel appliance package including a counter-depth French door refrigerator, recessed lighting, and a stylish coffee bar with open shelving. This level also includes a bedroom, a beautifully updated full bathroom with a tiled walk-in shower and frameless glass enclosure, and a convenient washer and dryer. The second floor serves as the main living space, showcasing vaulted ceilings, abundant natural light, and a comfortable gathering area. An enclosed loft on this level provides valuable additional sleeping or flex space, along with a second fully updated bathroom featuring a tiled walk-in shower and frameless glass door. The third floor offers a spacious bedroom, creating a private retreat for guests and separating sleeping areas for larger groups. This thoughtfully designed three level home comfortably sleeps 7 and is ideal for maximizing guest occupancy. The home has been upgraded with luxury vinyl plank flooring throughout the first and second floors and plantation shutters throughout, delivering a clean, coastal aesthetic that is both stylish and durable for short term rental use. A metal roof adds long term value, durability, and peace of mind for owners. The property also offers ample parking, a rare and valuable feature for vacation rentals in this area. Positioned in one of Tampa Bay's most desirable beachside locations, this property consistently attracts vacationers year round. The ability to rent nightly provides a major advantage for income generation, making this an ideal opportunity for investors or buyers seeking a beach home that can offset ownership costs. Popular local dining and entertainment options including Mad Beach Cantina and Bamboo Beach Bar are located just across the street, while John’s Pass Village and Boardwalk is also just steps away, offering waterfront dining, shopping, fishing charters, and boating excursions. Additional nearby favorites such as Candy Kitchen, Dockside Dave’s, Daiquiri Deck, and other local hotspots are all within walking distance. Enjoy incredible sunsets just moments from your front door along the Gulf shoreline. Offered fully furnished and beautifully appointed, this is a true plug and play investment ready for immediate use or continued rental.

Listing is courtesy of: WESTWARD REAL ESTATE (813-285-4456)

Listing Agent: John Pestalozzi Jr Llc (813-285-4456)

Remarks: Unrivaled waterfront living takes center stage in this just-renovated coastal masterpiece, perfectly positioned on a deep-water canal in prestigious Bay Point Estates—with quick, direct access to the Intracoastal Waterway and the Gulf of Mexico, placing world-class boating at your doorstep. Your private dock, sparkling pool, and seamless access to John’s Pass further elevate the experience, redefining the boating lifestyle. Enjoy a 1-mile walk to John’s Pass and a 5-minute walk to Madeira Beach and Caddy’s Waterfront Restaurant. A sweeping circular driveway framed by lush landscaping and swaying palm trees creates a striking first impression, offering exceptional curb appeal and ample parking. Inside, this beautifully designed 2-bedroom, 2-bath residence offers 1,802 square feet of light-filled living space, with a welcoming entry and a stylish front office or bonus room framed by glass-paneled doors—perfect for working from home or a quiet retreat. The home opens into a stunning open-concept living area where the kitchen, dining, and living spaces flow seamlessly together, enhanced by natural light and tranquil waterfront views. NEW Roof and A/C in 2025! At the heart of the home, the designer kitchen showcases quartz countertops, custom bright cabinetry, a center island with seating, and sleek glass-front appliances—ideal for everyday living and entertaining. Warm wood accents, curated coastal lighting, and refined finishes add depth and character, while expansive windows and sliding glass doors create a seamless connection to the waterfront. The open great room is a true showpiece, anchored by a dramatic floor-to-ceiling marble feature wall with a sleek linear fireplace, creating a focal point. Soft coastal tones and generous seating invite relaxation, while walls of glass frame serene water views and fill the space with natural light. The adjoining dining area is perfectly positioned to capture the view, completing the home’s indoor-outdoor flow. Privately tucked away, the primary suite offers a serene retreat with a light, airy ambiance and thoughtfully designed layout. The spa-inspired ensuite bath features a glass-enclosed shower with elegant tilework, dual vanities, and refined finishes reminiscent of a boutique hotel. A custom walk-in closet completes the suite, offering both style and organization. Step outside to your private waterfront oasis, where beautifully designed outdoor living spaces invite relaxation and entertaining. A sparkling pool is surrounded by expansive paver decking, offering multiple areas to lounge, dine, and enjoy the coastal breeze. A covered gazebo creates the perfect shaded retreat for morning coffee or evening cocktails, set against wide water views and swaying palms. The lush lawn and thoughtfully landscaped grounds add privacy and charm, enhancing the home’s resort-style ambiance. Enjoy peaceful moments poolside as dolphins glide by, or unwind on your private dock before heading out for a day on the water—made effortless with your remote-controlled 10,000 lb lift. The dock is new and features lighting for nighttime, two new boat motor lifts, and a fish cleaning station with plumbing and electric. With deep-water access and quick navigation to the Intracoastal Waterway and Gulf of Mexico, this property is truly a boater’s dream. This is coastal living at its finest—where every day feels like a vacation and the water is always within reach. Schedule your private appointment today!

Listing is courtesy of: MIHARA & ASSOCIATES INC. (813-960-2300)

Listing Agent: Raymond Mihara (813-960-2300)

Remarks: Under contract-accepting backup offers. Home received flood damage; Substantial Damage Letter attached under paperclip in MLS. This is a TWO lot parcel being sold for Land ONLY located a short walk to the Gulf of Mexico Beaches to the west.

Listing is courtesy of: RE/MAX PREMIER GROUP (813-929-7600)

Listing Agent: Paula Dysle (813-393-7015)

Remarks: One or more photo(s) has been virtually staged. Welcome to your coastal retreat. This beautifully renovated block construction home blends modern updates with timeless beachside charm, offering the perfect opportunity to enjoy the relaxed Florida lifestyle. This thoughtfully designed 2-bedroom, 1-bath residence features an open floor plan with stylish tile flooring throughout, creating a bright and welcoming living space. The updated kitchen is a standout, complete with stone countertops, custom wood cabinetry, and brand-new stainless steel appliances—perfect for both everyday living and entertaining. The bathroom has been tastefully updated with a double vanity and elegant tilework, combining functionality with a clean, modern aesthetic. Both bedrooms are generously sized with ample closet space, while all-new window treatments add a polished finish and privacy throughout the home. Just off the kitchen, a charming sunroom offers the ideal spot for morning coffee or evening wine. Outside, the beautifully landscaped, low-maintenance yard creates a private outdoor setting perfect for relaxing, grilling, and enjoying the coastal breeze. A unique feature of the property is the detached 240 sq. ft. block construction garage, offering incredible versatility—it could easily be converted into a studio, office, workshop, or additional living space. Recent upgrades include a whole-house water purification system, new hot water heater, new irrigation system, new interior washer and dryer, and an updated HVAC condenser, providing peace of mind for the next owner. Ideally located just minutes from Caddy’s, The Candy Kitchen, The Reef Bar & Grill, John’s Pass, and the beautiful Gulf beaches, this home places dining, shopping, entertainment, and the sand at your fingertips.

Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (727-472-1144)

Listing Agent: Alicia Warburton (201-424-3042)

Remarks: Charming Bungalow Site with Prime Location on Madeira Beach ! This unique property offers an incredible opportunity to build your dream home in one of the most sought-after locations in Florida. Previously a cozy bungalow, this home was impacted by Hurricane Helene and now offers a fresh slate for rebuild or new construction. Situated on a spacious 6,247 sq. ft. lot, an elevated home on this site would boast breathtaking views of the Intracoastal Waterway and it is just a short walk from the vibrant Johns Pass Village and Boardwalk, offering easy access to the beach, shops, restaurants, and local attractions. This prime lot is perfect for those looking to create their own coastal oasis in a thriving beach community. With its desirable location, this premier site is ready to be transformed into the home you've always envisioned. Don’t miss out on this rare chance to own a piece of paradise and start living the beach life today! Seller recently (11/24) completed an independent appraisal of the real property. Reports gives valuation of $595,000.

Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)

Listing Agent: Jacqueline Hammond Pllc (727-645-3029)

Remarks: One or more photo(s) has been virtually staged. SELLER OFFERING $7,500 TOWARDS BUYER'S CLOSING COSTS OR RATE BUYDOWN FOR CONTRACT THAT CLOSES ON or BEFORE MAY 29, 2026. Welcome to this beautifully remodeled 2-bedroom, 2-bath coastal retreat in the heart of Madeira Beach. Thoughtfully updated inside and out, this home offers a crisp, modern feel with quality finishes and true turnkey convenience. Major improvements include a NEW HVAC, new water heater, updated electrical and plumbing, luxury vinyl flooring, fresh interior paint, updated lighting, and a 2021 shingle roof. The kitchen features new cabinetry, stone countertops, and new appliances—including a dishwasher. Both bathrooms have been stylishly renovated, with a tiled walk-in shower in one and a tub/shower combo in the other. Outdoor living is just as enjoyable. The front yard showcases coastal shell landscaping for low-maintenance charm, while the fenced backyard offers excellent privacy with artificial turf—perfect for pets, relaxing, or effortless entertaining. Zoned R-2 and ideally located, short distance to the beach and John’s Pass Village, you’ll love having shopping, dining, and entertainment just moments away. Whether you're seeking a primary residence, second home, or investment opportunity, this property checks all the boxes. Here’s your chance to own a slice of paradise in Madeira Beach—come live where others vacation.

Listing is courtesy of: PLUMLEE GULF BEACH REALTY (727-595-7586)

Listing Agent: Betsy Sheffield (727-417-3204)

Remarks: One or more photo(s) has been virtually staged. One or more photo(s) has been virtually staged. * * INVESTOR ALERT! This is the unicorn you’ve been waiting for: a premium double lot property located right in the heart of the Madeira Beach corridor. NOTE THIS LISTING IS FOR THE SINGLE FAMILY HOME ON ONE LOT ONLY. For the LAND LOT ONLY, see Listing #TB8487234. This puts you just steps from the action, you are you are around the corner form the wildly popular John’s Pass Village, surrounded by the best waterfront dining, shopping, and entertainment the Gulf Coast has to offer. The existing structure is a completely remodeled (by a GC) and fully permitted, turnkey asset. Inside, you’ll find a 2-bedroom, 1-bath layout featuring luxury vinyl plank flooring, new energy-efficient double-hung windows, and a modern kitchen with granite countertops and a brand-new range and refrigerator. For peace of mind and insurance savings, this home is fortified for safety, featuring impact-rated exterior doors and a full set of lightweight Category 5 polycarbonate hurricane shutters. The 2022 roof is equally robust, upgraded with hurricane tie-down straps and a secondary water barrier. Additional mechanical updates include 2025 spray foam insulation in the crawlspace, a new 2024 HVAC, and a 2024 smart Wi-Fi enabled water heater. Combined double lot is zoned for 3 units, split the parcels to build a spec home (while living in the SFR), or utilize the entire compound as a high-performing rental. Seller is open to a purchase of JUST the lot or JUST the house, for the purchase of both please contact the Listing Agent. Opportunities like this in Madeira Beach are vanishingly rare—make your appointment to see it now!

Listing is courtesy of: REDFIN CORPORATION (617-458-2883)

Listing Agent: Katrina Jauregui (949-633-3204)

Remarks: Welcome to your coastal home in the highly sought-after Crystal Island neighborhood of Madeira Beach. This waterfront residence offers the perfect blend of Florida charm and modern updates. Waterfront Living at Its Finest: Situated on a 60' x 115' waterfront lot, this home offers wide canal views and provides quick access to both the Intracoastal Waterway and the Gulf. The home sits a few feet higher than others, and has proven its resilience during Hurricane Helene with very minimal impact. A new seawall and dock (2023) accommodate large vessels, including sailboats, making this an ideal home for boating enthusiasts. Bright, Updated Interiors: Step inside to discover gleaming refinished terrazzo floors throughout, creating a seamless flow between spaces. The bright Florida room serves as a perfect retreat, offering great water views and abundant natural light. The updated kitchen showcases modern quartz countertops, raised-panel cabinetry, stainless steel appliances and a convenient dining peninsula. Recent Upgrades for Peace of Mind: All new impact windows and doors (2023-2025); new shingle roof (2023); updated HVAC system (2021); and new impact-rated garage door (2025). Additional Features: Convenient inside laundry room and included washer/dryer; a spacious two-car garage; and a generous back yard with awning covered patio. This turnkey waterfront property offers the perfect combination of coastal living, modern updates, and boating accessibility. Don't miss this opportunity to own your piece of paradise.

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

Listing Agent: Tami Simms (727-743-6262)

Remarks: Exceptional Waterfront Opportunity on the Intracoastal Waterway! Don't miss this rare chance to own prime waterfront property with direct Gulf access. Positioned along the scenic Intracoastal Waterway, this parcel features a newer seawall and a private composite dock—perfect for boating, jet skiing, paddleboarding, kayaking, fishing, and embracing the full coastal lifestyle. The existing structure sustained significant hurricane damage and has not been remediated; the property is being sold for land value only, offering a blank canvas for you to design and build your custom waterfront oasis. Ideally located within walking distance to world-class beaches, top-rated dining, boutique shopping, and vibrant local entertainment. Whether you're envisioning a serene retreat or a luxurious showpiece, this is your opportunity to create your dream home in one of the area’s most desirable locations. Schedule your showing today and bring your vision to life.

Listing is courtesy of: EXIT KING REALTY (941-497-6060)

Listing Agent: Alysa Casorla (719-660-9695)

Remarks: PRICE IMPROVEMENT – Incredible opportunity in a prime Madeira Beach location just steps from the Gulf of Mexico. This property sustained significant flood damage during last year’s storm and the home is being sold in its current condition. The extent of the damage may require a full renovation or possible tear-down for new construction. Buyers are advised to conduct their own due diligence with the city, county, and any licensed contractors regarding rebuilding options, FEMA requirements, and current building codes. The existing structure previously featured two bedrooms, bonus room/study room, one and a half baths, multiple living areas, a detached one-car garage, and a fenced backyard with patio space. The home's interior, mechanical systems, and finishes were impacted by flooding and will need evaluation. The lot itself offers an exceptional setting in one of the most desirable pockets of Madeira Beach, only a short stroll to the sand, the Intracoastal Waterway, Caddy’s beachfront dining, and nearby shopping and attractions including John’s Pass. This property is now competitively priced according to condition and provides a rare opportunity to create or build your ideal coastal retreat. Sold as-is with the right to inspect. Buyer to verify all building, zoning, and restoration or redevelopment possibilities. If you'd like, I can also give you a slightly more aggressive investor-focused version.

Listing is courtesy of: SUNCOAST HOME REALTY (727-204-5001)

Listing Agent: Keyvan Kohan-Shohet (727-204-5001)

Remarks: Exceptional waterfront redevelopment opportunity in the heart of Madeira Beach. This 50x100 open-water lot at 249 144th Ave offers direct Intracoastal access with only the Johns Pass bridge between you and the Gulf, making this an outstanding site for a custom coastal residence or luxury spec build. The existing storm-damaged structure is being sold strictly AS IS for land value, with the true value centered in the lot, water frontage, and incredible open-water views across a basin lined with newer construction and high-end waterfront homes. The existing dock sustained significant storm damage and will require replacement, creating the perfect opportunity to design a new dock and lift configuration tailored to today’s boating lifestyle. This is the type of Madeira Beach lot that becomes harder to replace each year—surrounded by strong redevelopment momentum, upscale neighboring homes, and one of the most walkable boating-and-beach lifestyles in Pinellas County. Just a short walk to the sugar sand beaches, John’s Pass Village, waterfront dining, and entertainment, this location offers the rare combination of boating access, beach proximity, and premium rebuild upside. Whether you are building your forever waterfront home or positioning a high-end spec project in a market where coastal teardown lots continue to strengthen, this property offers exceptional long-term value in one of Tampa Bay’s most desirable beach communities.

Listing is courtesy of: EASY HOME SALES (727-201-8964)

Listing Agent: Jimmy Culler Jr. (727-290-7615)

Remarks: MOVE-IN READY! This beautiful BEACH HOME situated in a Corner Lot features 2/2 with Garage and back Entrance. This BLOCK house features: Open Layout Floor Plan, Contemporary New Kitchen, Quartz Countertop and Brand-New Stainless-Steel Appliances (2025). IMPACT WINDOWS and DOORS. Porcelain Tiles all around, Contemporary Showers, New Water Heater (2025), Utility Sink and Front-load Washer and Dryer INCLUDED. LED lights and Ceiling fans with remote. 200 AMP Electrical Panel. Irrigation System using reclaimed water. The House has Two Concrete Driveways. Back Entrance is ideal providing separate access to home. No HOA and no CDD. This house is perfect for full-time living, as an investment property, or vacation escape. Nowadays, you can enjoy the water view of Boca Ciega Bay and 150th Ave Drawbridge. Feel the Florida Lifestyle walking to the beach!

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Mia Rodriguez (727-483-4006)

Remarks: Island paradise, with room to relax or redevelop. Fully renovated, extremely spacious, 2-bedroom, 2-bath waterfront home on a rare oversized double lot in Madeira Beach—where boating, breezes, and open space come together the way coastal living is supposed to be. This easygoing beach home features a metal roof (including new trusses, sheeting, metal, insulation - 2013), two-car garage, and a new dock with a 14,000-lb boat lift (2021) complete with water and electric. Launch the boat, cruise the Intracoastal, or head out for a sunset ride—it’s all right in your backyard. Both the front and back yards are fully fenced, offering privacy and plenty of room to relax, entertain, or let pets roam. The expansive lot (over 100' wide) opens the door to outdoor living— waterfront grilling, firepit nights, or simply enjoying the salt air with room to spare. There's plenty of room to add a pool, too! The home was thoughtfully modified in 2013-2015 to provide for an open floorplan and capitalize on the water views. Having undergone an interior renovation in 2025, with all new appliances at that time. It is in near-perfect condition, move-in ready, while still leaving space for future expansion or personal touches. The seller also has full drawings for a 2nd floor addition to add a large primary suite for extra living space. For those looking ahead, the double lot offers potential to subdivide and build two new construction homes, adding long-term flexibility and value. Located just minutes from the beach, restaurants, and shops, this property delivers the laid-back Madeira Beach lifestyle—boating in the morning, beach walks in the afternoon, and waterfront evenings at home. Extra land. Deep coastal roots. Endless possibilities.

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

Listing Agent: Michael Wyckoff (727-642-6621)

Remarks: This is the kind of property some wait on… then regret when it’s gone. Solid block construction, stone and terrazzo floors, and a long water view the second you walk through the door. You’re looking straight out over the Intracoastal from the main living area and the primary bedroom — and it’s that classic Florida “I could do this every day” vibe. Here’s what matters: the demolition has already been done. PVC plumbing inside. Drywall is removed to the studs, floors and ceilings are intact, and the house is wide open for your design and layout. No guessing, no hidden surprises behind finished walls — you’re starting with a clean slate. There’s a davit for a small boat and jet ski's. Perfect for someone who wants water out back, a simple setup, and the beach at the end of the street. New roof (October 2021) Upgraded 200-amp electrical panel Blown-in attic insulation And if you’re thinking about the 50% rule, here’s the info - City of Madeira Beach preliminary report shows NOT substantially damaged Pinellas County Appraiser shows repairs/improvements up to $98,805 allowed for rehab. This is one of those rare Madeira Beach opportunities where you’re not paying for someone else’s design choices — you’re buying location, water, and a head start. Renovate it, elevate it, or rebuild it into something special. Waterfront. Walk to the beach. Long water view from inside the home. Big upside. If you’ve been waiting for a deal on the water in Madeira Beach… this is your shot.

Listing is courtesy of: EXP REALTY LLC (888-883-8509)

Listing Agent: Nathan Shirk (585-356-2197)

Remarks: LIVE THE MADEIRA BEACH DREAM – WALK TO THE BEACH, BOAT FROM YOUR BACKYARD! Just 5 minutes to the sand and sunsets, this updated 2-bed, 2-bath waterfront home captures the full Madeira Beach lifestyle. Beautifully rebuilt post-hurricane, the property has been fully restored to like-new condition—not substantially damaged by FEMA’s 50 Rule, meaning the original structure was preserved with no elevation required. Everything feels renewed: new HVAC system, hurricane-rated windows and doors with shutters, mold- and moisture-resistant drywall, raised electrical outlets for flood protection, and updated electrical throughout. The former porch has been fully enclosed and finished, adding extra flexible living space ideal for a den, office, or optional third bedroom. The lower kitchen cabinets and all bathroom cabinets have been replaced, along with new kitchen appliances and a new washer and dryer. Additional highlights include a tankless water heater, elegant wainscoting, and a freshly painted garage with a new electric door. Step outside to your private dock with a motorized boat lift, offering direct access to Boca Ciega Bay and a 10-minute boat ride to John’s Pass Village for dining, shopping, and entertainment. Beyond the property, you’ll love the neighborhood’s walkability—beach access, cafés, local restaurants, and mini golf - all just minutes away. Across the street, the Madeira Beach Recreation Center offers tennis courts, basketball, softball fields, a playground, and more. Whether you’re seeking a year-round residence or a coastal retreat, 15302 Harbor Drive delivers a rare blend of quality updates, waterfront access, and walkable beachside living—ready for you to move in and enjoy.

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

Listing Agent: Jenna Whitney (813-482-5792)

Remarks: This home is MOVE-IN READY! This 2-bedroom, 2-bathroom coastal retreat has been tastefully renovated on the first floor, offering a fresh, beachy vibe with all the comforts of turnkey living. Enjoy peace of mind with an assumable flood insurance policy. Thoughtfully refreshed, this is the first completed remodel of its kind in the area—giving buyers a rare opportunity for easy, low-maintenance living just steps from the water. A 4-point inspection has been completed. Hurricane-grade windows throughout are complemented by a 2021 HVAC system and a newer water heater, ensuring year-round efficiency and comfort. The primary suite is a must-see, featuring breathtaking intracoastal views and a gorgeous staircase leading to a private second-floor retreat—the perfect place to wake up to sparkling water and unwind with unforgettable sunsets. The downstairs bedroom offers flexibility and can easily be converted into a rentable or guest space, adding to the home’s versatility. Whether you’re seeking an investment property or a primary or secondary beach home, this location checks all the boxes. Tucked away on a peaceful cul-de-sac at the tip of the peninsula, the home is ideal for coastal living—grab your golf cart and hop around town, with easy access to the beach and the vibrant shops, dining, and entertainment of John’s Pass Village, where coastal convenience meets everyday tranquility.

Listing is courtesy of: CENTURY 21 BEGGINS (800-541-9923)

Listing Agent: Caitlin Beaird (727-209-7458)