Location: Crystal Island, Madeira Beach
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583 CRYSTAL DR, MADEIRA BEACH, FL 33708
$2,950,000114 Days on yellowkey MLS ID: TB8474247
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3614 Built: 1959 Tax: $19,391 (2024)Community: Crystal IslandSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$19,391
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Where Open Water Views Meet Privacy Positioned at the very end of the road with protected preserve frontage, this exceptional Madeira Beach waterfront estate enjoys a level of privacy rarely found along Florida's Gulf Coast. Here, water becomes horizon, neighbors disappear into the distance, and the views remain protected for generations to come. Set on nearly 160 linear feet of deep-water frontage, this remarkable residence offers the rare combination of wide-open water views, direct Gulf access, and a resort-inspired lifestyle designed for both relaxation and entertaining. Beyond its refined aesthetic, the home has been comprehensively remodeled with an emphasis on longevity, flow, and peace of mind. A thoughtful renovation transformed the home's connection to the water by removing walls and opening the living spaces to breathtaking panoramic views, creating a light-filled environment where nearly every gathering is framed by sparkling blue water. The chef's kitchen blends beauty and functionality with premium appliances, including a gas range with pot filler, while the reimagined living and dining spaces create an effortless flow for both everyday living and large-scale entertaining. Fully renovated bathrooms, impact-rated waterside windows and sliding glass doors, a newer HVAC system, updated electrical panel, and a 2021 barrel tile roof provide confidence behind the beauty. Step outside and discover what truly sets this property apart. Expansive pavered patios surround the resort-style pool, creating multiple venues for entertaining, relaxing, and enjoying the waterfront setting. A one-of-a-kind custom fire pit gathering area invites unforgettable evenings beneath the stars, while the open-water backdrop creates a sense of tranquility rarely found in today's waterfront market. Throughout the year, the property serves as a front-row seat to one of the area's most beloved traditions as illuminated boats glide across the water during the annual Christmas Boat Parade, creating a magical experience from the comfort of your own backyard. For boating enthusiasts, this is a true mariner's paradise. Nearly 160 feet of deep-water seawall, dual 10,000-pound boat lifts, and direct Gulf access with no fixed bridges provide effortless access to some of Florida's finest boating, fishing, and waterfront destinations. Despite its remarkable privacy, the home remains moments from Madeira Beach's award-winning shoreline, premier dining, shopping, and exciting new luxury developments, including the forthcoming Madeira Beach Marriott Autograph Collection Hotel. Convenient access to both St. Pete-Clearwater International Airport and Tampa International Airport makes travel effortless for full-time residents and seasonal owners alike. Rarely does a property combine open-water views, protected privacy, deep-water boating access, extensive renovations, and an irreplaceable location in a single offering. This is more than a waterfront home. It's a front-row seat to the Gulf Coast lifestyle.
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Tina Herrell (727-251-6630)
565 CRYSTAL DR, MADEIRA BEACH, FL 33708
$1,299,00086 Days on yellowkey MLS ID: TB8484714
REDUCED by $50,500 (3.7%) on 04/22/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2253 Built: 1959 Tax: $7,139 (2025)Community: Crystal IslandSpa: YesSingle Family
Taxes:$7,139
Elementary School: Orange Grove Elementary-PN
High School: Seminole High-PN
Tax Year: 2025
Middle School: Seminole Middle-PN
Remarks: Waterfront Perfection on Boca Ciega Bay/ Intracoastal! Experience the pinnacle of coastal living in this newly renovated Madeira Beach retreat, perfectly situated in the coveted Crystal Island enclave. This boater’s paradise features an expansive open floor plan that centers on panoramic Intracoastal views, with natural light pouring through brand-new hurricane-impact windows and sliding glass doors. Brand new updated kitchen featuring Frigidaire gallery appliance package, high-end quartz countertops, and top quality solid wood cabinetry with tons of space and storage throughout. Every inch of the interior feels fresh and sophisticated, from the 2.5 updated bathrooms with LED mirrors and sleek fixtures to the updated plumbing, electrical, and designer lighting throughout. Outside, a private backyard oasis awaits, featuring a sparkling pool with an brand new Jandy pool equipment (2026) with full spa automation and salt water system plus brand new gas heater (buried LP tank) and brand new electric sub panel with wireless/phone app control, lush landscaping, and a 2022 private dock with a high-end boat 10,000 lb lift with gem remote recently serviced and inspected and ready for your boat offering direct Gulf access! HVAC system is only a couple of years old and top quality Daikin, recently serviced/inspected, and in excellent shape. The Hot Water heater is brand new (2026), a 50-gal Rheem. Fenced back yard with all fencing and gates in great condition. This terrific home comes complete with a spacious two-car garage and is located less than a mile from the beach. This turn-key residence offers a seamless blend of luxury, comfort, and the ultimate Florida waterfront lifestyle. Seller Financing available!!!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Dawn Liedtke (813-956-3829)
534 CRYSTAL DR, MADEIRA BEACH, FL 33708
$3,449,00019 Days on yellowkey MLS ID: TB8509230
Bed: 6 Bath: 5.5 Gar: 6 Liv Area Sq Ft: 4848 Built: 2026 Tax: $8,137 (2025)Community: Crystal IslandSpa: YesSingle Family
Taxes:$8,137
Remarks: Perched along the sparkling Intracoastal Waterway in the heart of Madeira Beach, this exceptional new construction estate at 534 Crystal Dr delivers the rare combination of modern luxury, boating convenience, and elevated coastal living. Just moments from the sugar-sand beaches and vibrant waterfront dining of John's Pass Village & Boardwalk, this is a residence designed for those who want the very best of the Florida lifestyle. With quick access to the open waters of the Gulf of Mexico, boating enthusiasts will appreciate the premier waterfront setting with deep water dock, while the home itself offers an impressive collection of features rarely found at this price point. Thoughtfully designed for both grand-scale entertaining and everyday comfort, the expansive open-concept floorplan centers around a stunning chef’s kitchen with oversized gathering spaces inculding custom wood cabinetry, soild stone countertop and seamless indoor-outdoor flow. Offering 6 spacious bedrooms, a private theater room, dedicated home office, and an extraordinary 6-car garage, salt water heated pool, the residence blends sophistication with functionality for modern family living. The luxurious primary suite serves as a private retreat, complete with spa-inspired finishes and generous walk-in accommodations expected of a true luxury waterfront home. Along with the peace of mind that comes with all concrete block construction. Beyond the property itself, Madeira Beach offers an unmatched quality of life — known for its welcoming coastal community, excellent schools, family-friendly atmosphere, and year-round outdoor lifestyle. Whether enjoying sunset cruises, weekends at the beach, or entertaining waterfront guests, this home represents a rare opportunity to experience the best of Florida’s Gulf Coast living.
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Paul Simon (727-919-1927)
541 LILLIAN DR, MADEIRA BEACH, FL 33708
$875,000106 Days on yellowkey MLS ID: TB8477517
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1595 Built: 1960 Tax: $2,832 (2025)Community: Crystal Island 1St AddSpa: NoSingle Family
Taxes:$2,832
Remarks: Nestled along a serene wide canal with sailboat water and no fixed bridges, this delightful two-bedroom, two-bath home is a true waterfront haven. Picture yourself stepping aboard your boat and cruising effortlessly to the Gulf in just minutes—this is the kind of lifestyle dreams are made of. Recently updated and move-in ready, this charming retreat features an east-facing backyard shaded by mature trees—perfect for sipping your morning coffee or unwinding with a good book while the gentle breeze rolls in. Inside, the open floor plan flows beautifully, making it easy to entertain or simply relax. The spacious bedrooms are complemented by timeless plantation shutters throughout, adding elegance and charm. And with thoughtful updates like a new hot water heater, an electric panel with a generator plug, and a brand-new garage door, you’ll have convenience and comfort at every turn. Wake up to stunning sunrises over the water and embrace the tranquility of this coastal gem. Whether you’re an avid boater or simply looking for a peaceful retreat, this home is ready to welcome you to a life of relaxation and endless coastal beauty.
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: Amanda Baldwin (808-352-8669)
516 CRYSTAL DR, MADEIRA BEACH, FL 33708
$965,000225 Days on yellowkey MLS ID: TB8439054
REDUCED by $15,000 (1.5%) on 05/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2091 Built: 1959 Tax: $14,948 (2024)Community: Crystal IslandSingle Family
Taxes:$14,948
Remarks: Welcome to 516 Crystal Dr, a beautiful single-family POOL home! This fully updated 3-bedroom, 2-bathroom property offers nearly 2,100 square feet of living space, a 2-car garage, and a waterfront lot with a pool, dock, AND a new seawall! The home is move-in ready with a new kitchen that includes stainless steel appliances, white shaker-style cabinets, and an island with beautiful waterfall countertops. The open concept floor plan provides plenty of room for entertaining in the living room and dining room areas, and it also offers stellar views of the water and backyard. The primary bedroom also has direct access to the backyard and offers an en-suite bathroom with a freestanding tub and separate shower with floor-to-ceiling tilework. The additional bedrooms (one of which is a massive 18 ft x 14 ft) share the second full bathroom. The backyard includes pavers, a freeform pool, a dock, and unbelievable views of the waterfront with access to the bay. Conveniently located near schools, shopping, and major roadways. Call to schedule a showing today!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Matt Gardner (724-513-6012)
525 LILLIAN DR, MADEIRA BEACH, FL 33708
$800,000413 Days on yellowkey MLS ID: TB8376063
1 Days Off yellowkey (back on 5/26/2026)
REDUCED by $25,000 (3.0%) on 05/18/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1441 Built: 1963 Tax: $9,936 (2024)Community: Crystal IslandSingle Family
Taxes:$9,936
Remarks: Under contract-accepting backup offers. 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 Agent: Tami Simms (727-743-6262)
547 JOHNS PASS AVE, MADEIRA BEACH, FL 33708
$2,595,00015 Days on yellowkey MLS ID: TB8510503
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3481 Built: 1961 Tax: $14,555 (2025)Community: Crystal Island 2Nd AddSpa: NoSingle Family
Taxes:$14,555
Remarks: WELCOME TO 547 JOHNS PASS AVENUE A RARE OPEN WATER ESTATE FEATURING TWO PRIMARY SUITES, BREATHTAKING PANORAMIC VIEWS, AND THE ULTIMATE FLORIDA WATERFRONT LIFESTYLE. Perfectly positioned on an expansive stretch of wide-open water, this extraordinary coastal retreat was thoughtfully designed to capture spectacular views from nearly every room while blending luxurious indoor-outdoor living seamlessly throughout the home. From the moment you arrive, the circular paver driveway, lush tropical landscaping, and striking coastal architecture create an unforgettable first impression. Step through the grand entryway into a light-filled open-concept floorplan where soaring ceilings, oversized windows, and endless water views immediately steal the show. Designed for both elegant everyday living and effortless entertaining, the expansive living and dining spaces flow beautifully into the gourmet chef’s kitchen featuring custom cabinetry, stunning quartz countertops, oversized center island, premium Bosch appliances, designer backsplash, abundant storage, and an impressive wet bar with beverage refrigeration. Every detail has been thoughtfully curated to complement the home’s coastal aesthetic. One of the home’s most exceptional features is the presence of TWO PRIVATE PRIMARY SUITES offering incredible flexibility for multigenerational living, guests, or creating the ultimate private retreat experience. The first-floor primary suite features a spacious walk-in closet, ensuite bath, and convenient access to the main living areas, while two additional well-appointed guest bedrooms share a beautifully updated guest bathroom. A spacious laundry room is also conveniently located on the first floor. The entire second floor is dedicated to the luxurious grand primary retreat a true sanctuary of peace and tranquility. Wake up each morning to breathtaking sunrises and sweeping open water views through oversized windows designed to showcase the incredible scenery. This remarkable suite offers a spa-inspired ensuite bath, expansive walk-in closet space, private waterfront balcony, and a loft/office area ideal for working remotely while overlooking one of the most spectacular waterfront settings on the Gulf Coast. The upstairs retreat feels like a private penthouse oasis suspended above the water. Step outside into your private waterfront paradise where resort-style living awaits. The expansive travertine pool deck surrounds the sparkling saltwater pool and creates multiple areas for lounging, dining, and entertaining while overlooking the stunning open water backdrop. The covered balcony provides the perfect setting for morning coffee, evening cocktails, and unforgettable sunsets. Boating enthusiasts will appreciate the private dock and lift with direct access to open water. Every detail of this exceptional residence has been carefully designed to embrace the beauty of waterfront living while offering luxury, comfort, and functionality. With its rare dual primary suite layout, breathtaking views, and seamless indoor-outdoor design, this is more than just a home it is a private coastal sanctuary designed to experience the very best of luxury waterfront living.
Listing Agent: Kristin Leon (727-501-6516)
545 LILLIAN DR, MADEIRA BEACH, FL 33708
$735,000547 Days on yellowkey MLS ID: TB8327627
0 Days Off yellowkey (back on 5/11/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1697 Built: 1966 Tax: $2,820 (2024)Community: Crystal Island 1St AddSpa: NoSingle Family
Taxes:$2,820
Remarks: This Florida waterfront sailboat water lot and home has been partially remediated after the storms. It is ready for you, whether your goal is to rehab into a Florida winter home of your dreams or build up with new construction. As a 3 bedroom with bonus room it offers a large footprint on a wide 100ft canal that is just minutes from the Gulf of Mexico and Johns Pass. No storm will take the waterfront views away. The Christmas boat parades, the boating and fishing lifestyle and the neighborhood of family homes offer the best in Florida living. The wide 2-car garage and bonus room add footprint to elevate and room to remodel as desired. Our drone pic show you views from the 1st, 2nd and 3rd floor of a new potential residence so that you can see for yourself just how wonderful the Crystal Islands are as a place to make home.
Listing is courtesy of: CENTURY 21 BEGGINS (800-541-9923)
Listing Agent: Michael Reichenbach, Llc (800-541-9923)
584 CRYSTAL DR, MADEIRA BEACH, FL 33708
$1,550,00065 Days on yellowkey MLS ID: G5110056
REDUCED by $250,000 (13.9%) on 05/03/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1512 Built: 1958 Tax: $18,207 (2025)Community: Crystal IslandSpa: NoSingle Family
Taxes:$18,207
Remarks: Exceptional opportunity to own a prime waterfront lot in the highly desirable Madeira Beach, perfectly positioned on a quiet cul-de-sac on the Intracoastal Waterway. Boasting expansive, unobstructed Intracoastal water views, this property offers a rare setting to build a custom coastal retreat. The existing 3-bedroom, 2 bath home includes a private dock(equipped with a new 20,000 lb lift and secondary 10,000 lb lift), and pool-ideal for immediate use while planning your future vision. Surrounded by newer elevated homes, this location is perfectly suited for redevelopment or a high-end custom build. This property is a must see with its stunning water views, providing the ultimate backdrop for luxury waterfront living with direct boating access. Enjoy the best of coastal living with the beach located less than a mile away for quick trips to the sand and sunsets.
Listing is courtesy of: SCHMID PROPERTIES, LLC (352-243-3720)
Listing Agent: Carol Schmid (407-529-7399)
551 CRYSTAL DR, MADEIRA BEACH, FL 33708
$1,299,00039 Days on yellowkey MLS ID: TB8500772
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2436 Built: 1960 Tax: $6,551 (2025)Community: Crystal IslandSingle Family
Taxes:$6,551
Remarks: Sailboat water and over 2,400 square feet of living space in desirable Madeira Beach! This spacious waterfront home features three full bedrooms, each with its own private ensuite bathroom, and a desirable split floor plan for added privacy. The primary suite offers a walk-in closet and beautiful water views, creating a relaxing retreat. The open and airy layout is perfect for entertaining, with floor-to-ceiling water views from all main living areas, allowing you to enjoy the waterfront lifestyle from nearly every room. A formal dining room showcases a unique built-in stone dining table with seating for up to 12—ideal for hosting family gatherings and special occasions. Step outside and take advantage of true sailboat water access, complete with a 20,000-pound boat lift included, making this property perfect for boating enthusiasts. Enjoy the best of Florida waterfront living with space, comfort, and direct access to the open water. AC 2025 and Roof 2015.
Listing is courtesy of: ACTION REALTY OF TAMPA BAY INC (727-743-4083)
Listing Agent: Debbie Jackson (727-743-4083)
532 CRYSTAL DR, MADEIRA BEACH, FL 33708
$935,00078 Days on yellowkey MLS ID: TB8487459
0 Days Off yellowkey (back on 4/13/2026)
REDUCED by $15,000 (1.6%) on 04/06/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1748 Built: 1959 Tax: $6,888 (2025)Community: Crystal IslandSingle Family
Taxes:$6,888
Remarks: Under contract-accepting backup offers. Welcome to your waterfront retreat in Madeira Beach - a beautifully renovated three-bedroom, three-bathroom, two-story home designed for the ultimate Florida lifestyle. With direct canal access, a 2018 10,000 lb boat lift and dock this is truly a boater’s paradise where you can head out on the water anytime you please. This home offers peace of mind with major updates including 2025 Downstairs & 2019 upstairs A/C systems (with yearly maintenance), a 2024 water heater, 2024 & 2018 roofs, a 2014 seawall, hurricane-impact windows throughout, a hurricane-rated garage door, and paid-off solar panels - keeping the electric bill incredibly low. The first level features a bright open floor plan with stunning canal views, two bedrooms, two full bathrooms, and a flexible room that can be used as a dedicated office space perfect for working from home or easily converting to suit your needs. The kitchen is both stylish and functional, offering solid wood cabinetry, updated stainless steel appliances, quartz countertops, and a breakfast bar. The spacious living room is filled with natural light and features large glass sliders that seamlessly connect indoor and outdoor living - perfect for entertaining. One of the downstairs bedrooms includes its own private en-suite bathroom, while the guest bathroom offers a tub/shower combo. Ceiling fans are thoughtfully placed throughout the home for added comfort. The entire upstairs and balcony were added in 2018 and is dedicated entirely to the primary suite, creating a private sanctuary complete with hardwood flooring in both the bedroom and closet. Wake up to serene water views and step out onto your private balcony. The spa-like bathroom features a soaking tub, dual-sink vanity, abundant storage, and a glass-enclosed shower with a rain shower head and detachable handle. A large walk-in closet with custom shelving and the added convenience of a washer and dryer inside the bathroom complete this luxurious space. Step outside to your own slice of paradise where the great space outside was completed in 2012 - featuring a covered pavered patio ideal for dining, grilling, and relaxing year-round. The fenced backyard, dock, and waterfront setting make it easy to enjoy boating, kayaking, or simply watching wildlife right from your backyard. A large paver driveway leads to a two-car garage, providing ample parking and storage. Located just minutes from the beach, with easy access to bike lanes on Gulf Blvd to the Pinellas County trail, and close to local restaurants, parks, shopping, and activities, this home offers the perfect combination of luxury, location, and lifestyle. Don’t miss your opportunity to own this exceptional waterfront property!
Listing is courtesy of: EXP REALTY LLC (866-308-7109)
Listing Agent: Jeffrey Borham, Pa (866-308-7109)
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