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14077 N Bayshore Drive, Madeira Beach
$2,290,000
3 Beds ⋅ 2 Baths ⋅ Gulf Shores 3rd Add Rep SubDv. ⋅ 33708 Zip Code
Virtually Staged. LUXURIOUS AND CONTEMPORARY, WITH THE PERFECT L.A. BLEND OF MINIMALISTIC ELEGANCE, SUPERIOR FORM AND ADVANCED FUNCTION, THIS VISUALLY-STUNNING WATERFRONT RESIDENCE WAS BUILT WITH REFINED IMAGINATION AND YEARS OF FORWARD-THINKING! Remarkable planning and extraordinary attention to the smallest of details have yielded a home that breathes a beautifully rare and clean simplicity. High ceilings, tall windows, elegant engineered hardwood flooring and finishes designed to “float” throughout the home, deliver a deeply-satisfying, Andy Worhol-like living experience. Modern concept kitchen features inconspicuous white cabinetry, high-quality stainless steel appliances, gas cooking, quartz counters, large island bar and a wonderful multi-function pantry hidden away from the home’s open areas. Superb built-ins offer a distinct art deco flare that complement posh, state-of-the-art lighting and generous use of skylights. The inspired living area, with its sleek fireplace illumination, transitions to a fabulous open dining space overlooking the waterfront. Through pocketing sliding glass, take in grand, sweeping and unobstructed water views made possible by exquisitely-engineered cantilevered construction. Bringing all of your waterfront into view, you’ll love the expansive, 50 ft-wide (approx.) covered balcony with pristine porcelain floors, exterior marble façade, bench, planter and built-in gas for outdoor cooking & firepit. The owner’s suite enjoys private balcony access, neo-contemporary built-ins and a richly detailed closet system. Owner’s bath is a lavish, pampering experience; with its own unique combination of materials, design and color, you’ll be enthralled by the purity of concept in the partially-open rainshower, sublime soaking tub and custom double vanity – merging vintage wood credenza and modern granite surfaces. Large 2nd bedroom complements owner’s suite in style & substance. You’ll be drawn to the delightfully-appealing guest bath and its amazing use of light, tilework and composition. Plush theater room functions as a 3rd bedroom. Lower-level entry foyer has a rich welcoming feel, and extensive multi-purpose/storage space. Out back, discover 2 sizable covered private waterfront decks overlooking a gorgeous Pebbletech pool. Updated seawall, composite dock, backup generator, and many extras. Brilliantly conceived, and exceptionally well-built.

14077 N Bayshore Drive, Madeira Beach

249 144th Avenue, Madeira Beach
$799,000
2 Beds ⋅ 2 Baths ⋅ Madeira Shores 1st Add SubDv. ⋅ 33708 Zip Code
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.

249 144th Avenue, Madeira Beach

352 145th Avenue E, Madeira Beach
$3,299,000
4 Beds ⋅ 5 Baths ⋅ Madeira Shores 1st Add SubDv. ⋅ 33708 Zip Code
Stunning open-water sunset balcony views walking distance to the beach! This impressive three-story home has never been lived in and is designed for both luxurious living, sophistication, comfort and unforgettable entertaining. Inside, the residence showcases an impressive chef's dream Venetian-inspired gourmet kitchen designed to satisfy. Outfitted with an oversized 8-burner professional range, pot filler, and double ovens, this culinary space is as functional as it is striking. A 36-inch refrigerator and 36-inch freezer positioned side by side provide exceptional cold storage and convenience for large household, holiday gatherings, or upscale entertaining. Step outside to your resort-style oasis featuring a heated beach-entry pool with a swim-up bar and an attached under balcony heated 8-person spa that beautifully cascades into the pool. The hot summer southerly sun is no problem as the back balconies and 12 ft. sliding windows face North. For boating enthusiasts, your private dock offers a 9,000 lb. boat lift and an additional expansive 45-foot boat slip. Whether it's sailing, kayaking, paddleboarding or fishing from your dock prepare to have curious dolphins swim up under your feet adding that extra excitement to waterfront living. Upstairs, you'll find Italian tile throughout the second and third floors, adding timeless elegance throughout the home. The spacious primary suite features a luxurious stone floor finished double-headed walk-in shower along with an air jetted spa and tub for the ultimate inside retreat. This one-of-a-kind custom waterfront property combines luxury, comfort, boating access, and breathtaking sunset views in an exceptional coastal setting with local entertainment and activities at your doorstep. The entire home is concrete filled solid block three stories high to handle the elements. No top floor wood framing like most homes. The ground level provides garage capacity for up to 5 vehicles, allowing ample space for luxury automobiles, golf carts, water toys, or additional storage. An oversized rich wood finished elevator offers convenient access from the chandelier lit foyer to the upper floors, enhancing both comfort and accessibility throughout the home. This one-of-a-kind waterfront property offers an extraordinary combination of open-water views, beach proximity, boating accommodations, luxury amenities, and refined design making it a rare opportunity to own a premier piece of Gulf coastal real estate.

352 145th Avenue E, Madeira Beach

358 Boca Ciega Drive, Madeira Beach
$419,000
2 Beds ⋅ 2 Baths ⋅ Pages Rep Of Mitchells Beach 2 SubDv. ⋅ 33708 Zip Code
Virtually Staged. 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.

358 Boca Ciega Drive, Madeira Beach

583 Crystal Drive, Madeira Beach
$2,695,000
4 Beds ⋅ 4 Baths ⋅ Crystal Island SubDv. ⋅ 33708 Zip Code
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.

583 Crystal Drive, Madeira Beach

15302 Harbor Drive, Madeira Beach
$824,995
2 Beds ⋅ 2 Baths ⋅ Lone Palm Beach 5th Add Blk 29 Rep SubDv. ⋅ 33708 Zip Code
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.

15302 Harbor Drive, Madeira Beach

582 Johns Pass Avenue, Madeira Beach
$3,199,000
6 Beds ⋅ 6 Baths ⋅ Crystal Island 2nd Add SubDv. ⋅ 33708 Zip Code
Enjoy an exquisite 6,504 sq. ft. open water estate home on Madeira Beach’s limited access Crystal Island. This home offers 200 feet of open bay frontage at the end of a private cul-de-sac and was completely reimagined in 2013 with all new construction including roof, electric, plumbing, travertine floors, and hurricane-grade windows & doors, this residence blends elegance with peace of mind. This residence, with 4,255 HSF, welcomes you with a grand two-story entry and glass elevator. Grand staircase leads to a spacious second-floor great room with a full wall of sliders all opening to 1,461 sq. ft. balcony and spectacular open water views. The updated gourmet kitchen features stainless steel appliances, a large island with seating leading to open dining and living areas, ideal for entertaining bringing the outdoors in and inviting guests to enjoy the best in waterfront Florida living. Two master suites with luxurious ensuites complement three additional bedrooms and baths, plus a private mother-in-law suite on the lower level with direct bay access. Outdoor living shines and continues with another 1,125 sq. ft. covered porch featuring an outdoor kitchen, ample shaded seating and dining areas along with game area with Ping Pong, Table Tennis, Darts and fireplace. All this opens to the 40' pool and waterfall hot tub, and then a large pavered patio with comfortable lounge chairs for sunbathing. Added is a semicircular seated fire pit area for evening get togethers, cocktails and stories of the day’s activities. These likely came from the watersport fun from your array of toys, or your boats or trip on your yacht all kept at your updated deep-water dock equipped with power and water, as well as two lifts and large dock. The grounds are immaculately designed with water features and landscaped grounds at the front of the home and large available open astro-turfed areas in back. 3 Sheds provide additional storage and dual system ACs, and equipment are all out of view, but provide all the comfort expected. All of this is nestled within the limited-access Crystal Island subdivision of Madeira Beach - known for its golf-cart-friendly streets, award-winning beaches, lively City amenities including local festivals, boat parades, parks, libraries and more, and proximity to the shops, dining, and entertainment of Johns Pass Village - this home combines luxury and convenience. Just 35 minutes to Tampa International Airport and 25 minutes to St. Pete-Clearwater Airport, residents also enjoy quick access to the renowned arts districts of downtown St. Petersburg and championship sports franchises including the Tampa Bay Rays, Rowdies, Lightning, and Buccaneers and more. Just a day trip to some of the world's best theme parks means living here checks off all the boxes of luxury living along Florida’s best waters.

582 Johns Pass Avenue, Madeira Beach

440 S Bayshore Drive, Madeira Beach
$290,000
3 Beds ⋅ 2 Baths ⋅ Gulf Shores 4th Add SubDv. ⋅ 33708 Zip Code
INVESTMENT OPPORTUNITY. FLOOD DAMAGED HOUSE! PRICE HAS BEEN LOWERED ! AMAZING VALUE CLOSE TO THE WATER ! Welcome to a fantastic opportunity in Madeira Beach! This charming 3-bedroom, 2-bathroom single-family residence, built in 1945, offers a blank canvas ready for your vision. Nestled on a 3,986 square-foot lot, the home provides ample space for you to create your dream sanctuary. Step inside to discover a warm and inviting atmosphere. The home's interior features a spacious open layout, where natural light floods the rooms, creating a bright and airy feel throughout. The central air conditioning ensures comfort, while tile flooring adds a sleek, modern touch. Though the kitchen and living areas are in need of some TLC, the possibilities are endless, allowing you to transform the space into a home that truly reflects your style. The primary bedroom, along with two additional bedrooms, each offers plenty of potential. While none of the bedrooms come with built-in closets, this presents a unique opportunity to design custom storage solutions that perfectly fit your needs. The two bathrooms, though simple, provide a functional space ready for upgrades. The home sits on a slab foundation with a traditional shingle roof, providing durability for years to come. Though there is no garage, the carport area offers convenient parking, and with no HOA restrictions, you're free to make this property truly yours. A true fixer-upper, this property allows you to reimagine every corner, whether you're looking to modernize the interior or create an outdoor oasis. The backyard is a blank slate, offering the ideal space for a garden, patio, or additional entertaining areas. Located just moments away from the pretty Madeira Beach , this home promises to be a rewarding project for the right buyer. Don't miss out on this rare opportunity to own a piece of Madeira Beach with immense potential. With a bit of imagination and effort, you can turn this house into your forever home! The back yard belongs to the city, it is not private.

440 S Bayshore Drive, Madeira Beach

13004 Boca Ciega Avenue, Madeira Beach
$559,000
2 Beds ⋅ 2 Baths ⋅ Pages Rep Of Mitchells Beach 2 SubDv. ⋅ 33708 Zip Code
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.

13004 Boca Ciega Avenue, Madeira Beach

15318 Harbor Drive, Madeira Beach
$1,500,000
3 Beds ⋅ 2 Baths ⋅ Lone Palm Beach 5th Add Blk 29 Rep SubDv. ⋅ 33708 Zip Code
Diamond In the Rough. New Fence, New Garage Door. You have a fabulous opportunity to purchase this unique property in one of the fastest-growing cities. Madeira Beach. This pool home is on a dead-end street among Multi-Million Dollar homes. This home sits on 90 feet of Boca Ciega intercoastal waterway—Sailboat waters with a dock connected to water & electricity. Due to Helene visiting this home the owner is planning on renovating. If this is your planned area you can make this 3/2 home a mid-century modern potential the way YOU want and make this property a Multi-Million dollar home. Walking distance to shopping centre, beach, restaurants, and more. This home is perfect for the boat & fishing lover. Enter the KING OF THE BEACH tournament or watch the boats come in with the big ones while sitting at your pool with a margarita or walk over and see the weigh-in. Don't miss out on this gem. The owner is ready for the country. Are you ready for the Beach?

15318 Harbor Drive, Madeira Beach