Location: Madeira Beach
Do Not Show Listings
728 PRUITT DR, MADEIRA BEACH, FL 33708
$1,225,00050 Days on yellowkey MLS ID: TB8494283
REDUCED by $25,000 (2.0%) on 04/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1802 Built: 1954 Tax: $6,822 (2025)Community: Bay Point Estates 1St AddSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$6,822
Elementary School: Orange Grove Elementary-PN
High School: Seminole High-PN
Tax Year: 2025
Middle School: Seminole Middle-PN
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)
14033 PALM ST, MADEIRA BEACH, FL 33708
$450,00066 Days on yellowkey MLS ID: TB8488524
0 Days Off yellowkey (back on 4/24/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1357 Built: 1948 Tax: $3,558 (2024)Community: Gulf Shores 2Nd AddSingle Family
Taxes:$3,558
Elementary School: Bauder Elementary-PN
Tax Year: 2024
Remarks: Under contract-accepting backup offers. Here’s your chance to own an affordable BEACH HOUSE in the heart of Madeira Beach, just steps from the sand and moments from breathtaking Gulf sunsets. Perfectly positioned with beach access directly across the street at Caddy’s, this property offers the ultimate coastal lifestyle in one of the most desirable locations on Florida’s Gulf Coast. This 3-bedroom, 3-bath beach cottage features an open-concept layout with a spacious kitchen, living, and dining area designed for easy living and entertaining. The large primary suite includes a walk-in closet and private ensuite bath, adding comfort and functionality. Step outside to a truly unique and fully fenced backyard oasis built for entertaining, complete with a custom outdoor bar, dedicated cornhole court with sand alley, paver patio, raised wooden deck, and ambient string lighting. The garage has been thoughtfully converted to enhance the outdoor experience and includes a 12x9 climate-controlled space—ideal for storage, tools, or even a keg setup. A large Lifetime shed adds even more storage flexibility. The low-maintenance yard, paved driveway, and ample parking make this property as practical as it is fun. Originally renovated in 2015, the home offers a strong foundation for its next owner, including mostly (around 90%) updated electrical, PVC plumbing, hurricane-impact windows and doors, and a roof approximately 10 years old. The home sits on a raised crawl space. While the property did experience flooding during Hurricane Helene, it has been officially deemed NOT substantially damaged, offering a valuable opportunity to restore, customize, or reimagine the space to your vision. Flood insurance is assumable, providing additional peace of mind. Located just minutes from John’s Pass, local restaurants, shopping, and entertainment. With trolley access nearby, this home is ideal as a primary residence, vacation getaway, or investment property.**Interior pictures include both pre and post storm**
Listing Agent: Michael Cinquemano, Jr. (813-960-2300)
725 SUNSET CV, MADEIRA BEACH, FL 33708
$499,999293 Days on yellowkey MLS ID: TB8415202
REDUCED by $20,001 (3.8%) on 05/14/2026
Bed: 3 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 1233 Built: 1952 Tax: $3,555 (2024)Community: Bay Point Estates 1St AddSingle Family
Taxes:$3,555
Elementary School: None
High School: None
Middle School: None
Remarks: Move right in! Beautiful, Florida Beach Home. Completely remodeled with permitting. This could be your Florida Beach Home to love and enjoy. What a pretty location. Just a couple houses walk to the private, neighborhood waterfront dock and green space. This waterfront park also has a small boat ramp. Sip your morning coffee or enjoy the evening sunsets here-waterside. Watch the dolphins play and maybe even see a group of manatee swim by. This is a true 2 bedroom home with a third very large room that could be used for an amazing third bedroom or guest room. The current owner is using it as an office and an oversized "department store" style closet! You may fall in love with it too. The home has an inside laundry/utility room plus a one car garage that could fit a small/compact car or fun Deluxe-Beach Golf Cart, kayaks, paddle boards and more. Outside you have a resort style front and back yard. The back yard has an outside shower that's great after a day of boating, swimming at the beach or gardening. Enjoy the extra storage and especially the outside Kitchen/grilling entertaining area. Relax and put your face to the sun. Fall asleep reading your favorite book. You can unwind in the small yet attractive portable fresh water pool the owner has set up. The home inside has been remodeled with most updates being as new as 2025! The home has an attractive modern kitchen with an island sitting area. All appliances will be staying for the new owner. Both bedrooms are a good size with nice window placement allowing the natural sunlight in! The woodwork throughout adds to the character and quality of this home. Look at the doors, door trim, crown molding and baseboards. Notice the high quality and stylish bathroom design and tile work. The back room would be a nice dining area, library, exercise or hobby/art room. You'll find neutral paint colors with a splash of bright color throughout. Sunset Cove is a beautiful street with two green space lots nearby this home. What a wonderful place to live! You could Move right in now and make this your full time residence...or make a nice Florida real estate investment purchase. There's plenty of parking with the paved circle drive. This could be an amazing opportunity also as a second Florid Beach Property (only blocks to the beach) for Family, Friends to visit. The entire Central heat and A/C have just been replaced August 2025. Walk to the beach. Enjoy nearby breakfast cafe and Candy Kitchen for ice creme and sweet treats. The Famous waterfront John's Pass Village is fun to walk or bike ride to with jet ski rentals, parasailing, fishing charters and dolphin watching tours available.. Dining, entertainment and shopping seem extra special here at the beach! Bring your boat, paddle boards, kayaks and enjoy the outdoors. It's so comfortable and beautiful here. We love it!
Listing is courtesy of: COLDWELL BANKER PICKETT FENCES REALTY (727-395-9492)
Listing Agent: Heather Staton (727-709-7355)
14919 N BAYSHORE DR, MADEIRA BEACH, FL 33708
$625,000105 Days on yellowkey MLS ID: TB8475137
3 Days Off yellowkey (back on 5/13/2026)
REDUCED by $25,000 (3.8%) on 05/04/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1404 Built: 1972 Tax: $7,703 (2025)Community: North Madeira ShoresSingle Family
Taxes:$7,703
Remarks: Under contract-accepting backup offers. Exceptional investment opportunity in highly desirable Madeira Beach. This fully renovated duplex has been updated from top to bottom and is move-in ready. Both units feature brand-new kitchens with white shaker cabinetry and quartz countertops, with matching finishes carried into the bathrooms. Additional upgrades include luxury vinyl plank flooring throughout, new ceiling fixtures, new doors, new drywall, all new electrical wiring, a new roof, newer windows (approximately 4 years old), and a new water heater. Each unit offers 2 bedrooms and 1 bathroom, providing flexible living options — occupy one side while generating income from the other, or rent both units for strong cash flow potential. Comparable canal-area rentals of similar size are leasing for approximately $2,500 per month per unit, creating an estimated income potential near $5,000 monthly. Ideally located in the heart of Madeira Beach, just moments from the renowned white sandy beaches, dining, shopping, and entertainment. Schedule your showing today and secure a turnkey coastal investment before it’s gone.
Listing is courtesy of: YOU FIRST REALTY AND ASSOC LLC (813-458-6686)
Listing Agent: Ramez Lahham (813-458-6686)
352 144TH AVE, MADEIRA BEACH, FL 33708
$750,00036 Days on yellowkey MLS ID: TB8499790
REDUCED by $49,000 (6.1%) on 05/13/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1232 Built: 1950 Tax: $5,288 (2025)Community: Madeira Shores 1St AddSingle Family
Taxes:$5,288
Remarks: PRICE REDUCED !!!!! This three-bedroom, two-bathroom residence boasts a meticulously renovated interior, blending contemporary elegance with a welcoming atmosphere. All plumbing and electrical systems are entirely new, and the appliances—brand new—remain with the property for immediate convenience. Located in Madeira Beach, just two blocks from the shore, it offers an enviable location for vacations or family living. The interior dazzles with newly tiled floors throughout, and the roof was fully renovated in 2021 for lasting durability. Impact-resistant windows ensure protection from hurricane winds. Additionally, the air conditioning and water heater are also newly installed, ensuring maximum comfort. The façade, with its coastal blue hue and crisp white accents, radiates freshness, while the geometric driveway and palm trees add a tropical character. In the backyard, a modern pool and relaxation area create a private oasis. Don’t miss the opportunity to make this beautiful property yours in the Sunshine State, where quality, location, and style come together to offer you the home you’ve always dreamed of!
Listing is courtesy of: DOMINO REALTY (407-466-3585)
Listing Agent: Ivan Santana (407-466-3585)
14215 N BAYSHORE DR, MADEIRA BEACH, FL 33708
$1,450,000125 Days on yellowkey MLS ID: V4946801
REDUCED by $25,000 (1.7%) on 05/11/2026
Bed: 3 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3358 Built: 2001 Tax: $21,742 (2025)Community: Gulf Shores 1St AddSpa: NoSingle Family
Taxes:$21,742
Remarks: Experience refined coastal luxury with sweeping views of the Gulf of Mexico. This elevated waterfront residence offers 3 bedrooms, 3.5 baths, TWO primary suites, an elevator, and a 3-car garage, thoughtfully designed for upscale living. The open-concept main level features a chef’s kitchen flowing seamlessly into the living and dining areas, all framed by breathtaking water views and abundant natural light. The third-floor primary suite is a private retreat with its own balcony, two walk-in closets, and a spa-style bath with jacuzzi tub and walk-in shower. A second primary suite offers Gulf views, private balcony, and en-suite bath. Additional highlights include two wood-burning fireplaces, luxury vinyl flooring, and surround sound. Enjoy effortless waterfront living with a brick paver yard, mature palms, private dock, and 10,000-lb boat lift with quick Gulf access. Watch dolphins, fish from your dock, and enjoy Madeira Beach fireworks from home. Recent updates include a 2023 roof and water heater, updated HVAC, fresh interior paint, dishwasher and refrigerator (2025). Just steps to the beach and minutes to John’s Pass, dining, and shopping—this is truly a boater’s paradise.
Listing is courtesy of: OCEAN REALTY PARTNERS LLC (321-323-1212)
Listing Agent: Melanie Zwolski (407-462-8588)
545 LILLIAN DR, MADEIRA BEACH, FL 33708
$735,000538 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)
13004 BOCA CIEGA AVE, MADEIRA BEACH, FL 33708
$559,000741 Days on yellowkey MLS ID: U8243128
REDUCED by $10,000 (1.8%) on 05/09/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1196 Built: 1946 Tax: $1,731 (2024)Community: Pages Rep Of Mitchells Beach 2Single Family
Taxes:$1,731
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 Agent: Caitlin Beaird (727-209-7458)
451 VIRGINIA AVE, MADEIRA BEACH, FL 33708
$299,00021 Days on yellowkey MLS ID: TB8505099
0 Days Off yellowkey (back on 5/8/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1008 Built: 1954 Tax: $4,406 (2025)Community: Gulf Shores 4Th AddSingle Family
Taxes:$4,406
Remarks: Under contract-accepting backup offers. Exceptional redevelopment opportunity in the heart of Madeira Beach. This 52-by-100-foot property offers the potential to build a custom coastal residence or explore renovation possibilities for the existing structure, which sustained storm-related damage from recent hurricanes. Buyers are encouraged to verify all structural conditions, zoning requirements and redevelopment potential. Existing improvements include a detached carport and a roof replaced in 2020. Whether envisioning a luxury beach retreat, full-time residence or investment project, the property presents a rare opportunity in one of the Gulf Coast’s most active redevelopment areas. Madeira Beach continues to experience significant revitalization and new development activity, further enhancing the area’s long-term appeal and value potential. Located just moments from the Gulf beaches, local restaurants, shopping and waterfront attractions, with John’s Pass Village and Boardwalk nearby and convenient access to downtown St. Petersburg and Tampa International Airport. A prime opportunity to secure a piece of Madeira Beach as the area continues to evolve and grow.
Listing is courtesy of: BEACH & BAY REALTY LLC (727-595-0366)
Listing Agent: Aimee Smith (727-304-8776)
538 LILLIAN DR, MADEIRA BEACH, FL 33708
$959,90074 Days on yellowkey MLS ID: TB8486579
1 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1600 Built: 1963 Tax: $4,753 (2025)Community: Crystal Island 1St AddSingle Family
Taxes:$4,753
Remarks: Under contract-accepting backup offers. BACK ON THE MARKET! Lets get you in there to take a look.Welcome to 538 Lillian Dr, Madeira Beach, FL! This beautifully renovated 3-bedroom, 2-bathroom home is a true gem, offering the perfect combination of coastal charm and modern upgrades. Located just minutes from the pristine beaches of Madeira Beach, this home is a dream for those looking to enjoy the best of Florida living. Step inside to find stunning new flooring throughout, creating a sleek and cohesive look. The completely updated kitchen is a chef’s delight, featuring brand-new cabinets, gorgeous granite countertops, and top-of-the-line stainless steel appliances. It’s the perfect space for cooking and entertaining. Both bathrooms have been fully renovated with modern finishes, new fixtures, stylish vanities, and custom tiling. Every detail has been thoughtfully designed for comfort and style. The open-concept living area is beaming with natural light, and the flow from the living room to the dining area and kitchen creates a welcoming, spacious environment. The Florida room has been transformed into a cool addition to the living space. Step outside to a beautifully landscaped yard with plenty of room for outdoor activities, plus a covered patio – perfect for enjoying Florida’s year-round sunshine. Additional features include a 2-car garage, plenty of parking space, and a location just minutes from local shops, dining, and the famous John’s Pass Village. This property has two boat lifts, 1-19 ton the other a 10 ton lift. This home is a true turnkey opportunity—schedule your showing today and make 538 Lillian Dr your new paradise retreat!
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Timothy Dube (727-201-6265)
584 CRYSTAL DR, MADEIRA BEACH, FL 33708
$1,550,00056 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)
13135 4TH ST E, MADEIRA BEACH, FL 33708
$450,00090 Days on yellowkey MLS ID: TB8480037
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 793 Built: 1946 Tax: $6,730 (2025)Community: Pages Rep Of Mitchells BeachSingle Family
Taxes:$6,730
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)
363 145TH AVE E, MADEIRA BEACH, FL 33708
$479,900249 Days on yellowkey MLS ID: TB8428034
0 Days Off yellowkey (back on 5/2/2026)
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1351 Built: 1950 Tax: $8,821 (2024)Community: Madeira Shores 1St AddSingle Family
Taxes:$8,821
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)
15424 2ND ST E, MADEIRA BEACH, FL 33708
$575,00077 Days on yellowkey MLS ID: TB8483691
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1103 Built: 1947 Tax: $4,451 (2025)Community: Lone Palm Beach 4Th AddSingle Family
Taxes:$4,451
Remarks: Paradise awaits just two blocks from the beach! Nestled in a sought-after neighborhood behind the iconic Smuggler’s Cove Miniature Golf Course, this stunning 3-bedroom, 2-bathroom home is ready for you to move right in. The property boasts a spacious backyard, offering endless potential to create your own private oasis. Every detail of this home has been thoughtfully updated, with brand-new features throughout, ensuring a fresh and modern living experience. Imagine enjoying the beach lifestyle every day, with the convenience of being within walking distance to a variety of local shops, vibrant bars, and delicious restaurants. Whether you're searching for a primary residence or the perfect beachside escape, this home delivers the ultimate coastal living experience. Plus, with easy access to two major airports, weekend getaways and travel plans couldn't be more convenient. If you've been dreaming of sun, sand, and a laid-back lifestyle, this is your chance to make it a reality. Welcome to your slice of paradise!
Listing is courtesy of: COMPASS FLORIDA LLC (727-339-7902)
Listing Agent: David Petrucelli (813-629-1358)
14045 E PARSLEY DR, MADEIRA BEACH, FL 33708
$629,00035 Days on yellowkey MLS ID: TB8498934
1 Days Off yellowkey (back on 5/1/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1627 Built: 1958 Tax: $2,506 (2025)Community: Gulf Shores 6Th AddSingle Family
Taxes:$2,506
Remarks: Under contract-accepting backup offers. Set on a wide canal with 48 feet of water frontage and quick access to the Intracoastal and the Gulf, this is a true waterfront opportunity in the heart of Madeira Beach. The setting delivers the beach lifestyle buyers are looking for—easy boat access with a coastal environment where dolphins, manatees, and native birdlife are part of the everyday scene. There’s also ample room to design a backyard with a pool, creating a true indoor-outdoor waterfront setup. The beach is just 700 yards away, making Gulf access just as convenient by foot as it is by boat. Nearby favorites like Corner Kitchen & Coffee House, Caddy's, and Smuggler's Cove are all within easy reach, while John's Pass Village is less than a mile and a half away for waterfront dining, shopping, and live music. Beyond the immediate area, you’re approximately 15 minutes to Corey Avenue and its popular Sunday market, about 30 minutes to downtown St. Petersburg, 30 minutes to St. Pete–Clearwater International Airport, and roughly 35 minutes to the Gandy Bridge connecting you into Tampa. This location has the perfect balance of a laid-back residential feel with close access to everything that makes the area desirable. This is the perfect blank canvas to create your dream, where the lot, location, and water access set the stage for something exceptional.
Listing Agent: Melinda Persuitte (813-777-6336)
50 137TH AVENUE CIR, MADEIRA BEACH, FL 33708
$424,900141 Days on yellowkey MLS ID: TB8456428
REDUCED by $44,100 (9.4%) on 05/01/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1947 Tax: $6,993 (2024)Community: Gulf Shores Harbor SubSpa: NoSingle Family
Taxes:$6,993
Remarks: Exceptional waterfront opportunity in the heart of Madeira Beach. Just steps from Gulf Boulevard with convenient public beach access—never worry about finding parking, and walkable to Caddy’s Madeira Beach and the iconic Candy Kitchen. Offering 27 ft of seawall and direct access to Boca Ciega Bay, this property provides excellent boating potential with access through John’s Pass and no fixed bridges. The property has been remediated post-Hurricane Helene, creating a solid starting point for a future build or custom coastal vision. Located on a 3,502 sq ft lot, the existing residence offers a flexible footprint and a true blank canvas. With no HOA restrictions, buyers have the freedom to design and build in alignment with modern standards and today’s design preferences. Surrounded by new construction and continued reinvestment, this area continues to evolve, making it an ideal opportunity for builders, investors, or buyers seeking a prime Madeira Beach location. Minutes to John’s Pass Village & Boardwalk, boating, dining, shopping, and entertainment, with easy access to Downtown St. Petersburg and Tampa International Airport. Sold as-is with right to inspect.
Listing is courtesy of: COLDWELL BANKER REALTY (813-286-6563)
Listing Agent: Lisa Mcintyre (630-414-7370)
583 CRYSTAL DR, MADEIRA BEACH, FL 33708
$2,950,000105 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
Taxes:$19,391
Remarks: Where open water views meet privacy... A lifestyle-driven, wide-open-water estate with resort outdoor living. Positioned where water becomes horizon and privacy becomes absolute, this exceptional Madeira Beach estate offers a level of seclusion rarely found on the Gulf Coast. End-of-the-road placement with preserve frontage ensures uninterrupted views, enduring privacy, and no future development risk. Beyond its refined aesthetic, the residence has been comprehensively remodeled with an emphasis on longevity, flow, and peace of mind. During renovation, the original water-facing wall and Northeast wall was thoughtfully removed to open the home to expansive water views, creating a new luminous dining area and living experience. Enhancements include a 2021 barrel tile roof, new impact windows and sliding glass doors along the waterside, a newer HVAC system, new electrical panel (2021), all new appliances, including a gas stove with a pot filler, and fully reimagined bathrooms throughout—ensuring the home is as sound as it is beautiful. Outdoors, a resort-style pool is surrounded by expansive paved patios, a one of a kind fire pit surround, and all of this is framed by water on three sides, offering an ideal setting for both intimate gatherings and grand celebrations. This spot gives you a front row seat to the most Spectacular Christmas Boat Parades. Nearly 160 linear feet of deep-water seawall, dual 10,000-lb boat lifts, and direct Gulf access with no fixed bridges create a true mariner’s haven. Set within a peaceful enclave of Madeira Beach, yet moments from world-class dining, shopping, new luxury development, a short drive to both St. Pete/ Clearwater airport and Tampa airport and the forthcoming Madeira Beach Marriott Autograph Hotel, this residence offers the rare balance of tranquility and proximity. For buyers seeking a waterfront home that combines location, lifestyle, and meaningful upgrades for long-term confidence—this is a compelling opportunity in today’s market. This is Gulf Coast living—elevated.
Listing is courtesy of: RE/MAX ACTION FIRST OF FLORIDA (727-531-2006)
Listing Agent: Tina Herrell (727-251-6630)
551 CRYSTAL DR, MADEIRA BEACH, FL 33708
$1,299,00030 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)
249 BOCA CIEGA DR, MADEIRA BEACH, FL 33708
$1,785,00032 Days on yellowkey MLS ID: O6402270
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 2160 Built: 1930 Tax: $12,232 (2025)Community: Pages Rep Of Mitchells BeachSingle Family
Taxes:$12,232
Elementary School: Madeira Beach Elementary-PN
High School: Boca Ciega High-PN
Middle School: Madeira Beach Middle-PN
Remarks: The property is approximately 9,587 square feet of deep hurricane sheltered waterfront. The lot currently has three small cottages across two lots that must remain in place to secure the grandfathered non-conforming footprint. Once a site development plan has been approved the cottages can be torn down. Depending on the purchaser, either the footprint can be maintained with three single family homes built or the two lots can support two single family homes that most likely would require variances with set backs due to buildable lot size. Ideally the purchaser will build three FEMA, County and City approved structures, three stories each with parking on the first floor and two floors of living space. The current footprints of each structure is roughly 16 feet wide by 45 feet long.
Listing is courtesy of: ROMAN'S PRO REALTY LLC (407-610-1970)
Listing Agent: Petie Bilyk (407-361-1415)
445 129TH AVE E, MADEIRA BEACH, FL 33708
$6,700,000251 Days on yellowkey MLS ID: TB8427384
Bed: 5 Bath: 5.5 Gar: 8 Liv Area Sq Ft: 5785 Built: 2025 Tax: $14,392 (2024)Community: Williams Bill Madeira Harbor Sub 3Rd AddSpa: YesSingle Family
Taxes:$14,392
Remarks: Auction Property. LUXURY PRIVATE AUCTION. This property is being offered via luxury private auction. Submit offers now through June 18th. Seller may accept or reject bids at any time. Visit Paramount Realty USA’s website for full terms and details. This architectural marvel, designed and developed by Tulia Homes, is an artistically thoughtful residence that is the epitome of luxury waterfront Florida living. Location is everything with this home, which is nestled on a peninsula overlooking Boca Ciega Bay, with clear sightlines to Little Bird Key and Eleanor Island. You can enjoy ocean breezes with sunsets or sunrises, whether you experience them inside or out. Owning this home is more than owning a house — it's a lifestyle, and it does not disappoint. Your private dock allows convenience when you embark on boating excursions to the Gulf, with quick and easy access through John's Pass. This 5,785 sq. ft. residence boasts an open-floor living space for ultimate entertaining, five bedrooms, four en suites, one and a half guest baths, a gym/yoga meditation room, pool/spa, 360-degree view rooftop, and an eight-car parking garage. Enjoy picturesque views from every corner of this home. Floor-to-ceiling windows overlooking the ocean to the east allow for perfect sunrises as dolphins swim by while you sip your morning coffee from one of the expansive terraces or relax by the saltwater pool. High above sea level is the main living space, thoughtfully designed for coastal living and entertaining. A chef's kitchen, butler's pantry, two living areas, wet bar, temperature-controlled wine room, and a dining room all overlook the shimmering sea. All of this can be enjoyed with the entire wall of windows automatically opening to the fresh ocean breeze. This level also has two guest bedrooms (or office) with en suites, walk-in closets, and a powder room. On the second floor, you will find two guest bedrooms, two bathrooms, a fitness room, laundry area, an informal living room, and a spacious and serene primary suite with its exquisite spa-like bathroom equipped with a breakfast bar, double shower, soaking tub, and formal dressing room. Next, take the all-floor-access elevator up to the third floor and be greeted by a wet bar, which leads you to an incredible 360-degree view rooftop — perfect for spectacularly memorable sunsets or improving your putting skills, all while overlooking the ocean. All of this is located just steps away from the John's Pass Boardwalk, John's Pass Park & Beach, and everything Gulf Boulevard has to offer. Tulia Homes doesn't just build homes — they build sanctuaries for joy, pride, and cherished memories with family and friends for generations to come! Contact us today to schedule a private tour of this breathtaking and visually stunning property, sitting at the access point of the Gulf and the apex of Florida coastal living
Listing Agent: Dj Soucy, Jr (617-308-4442)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.