Madeira Beach Homes with Sailboat Water Water Frontage

Madeira Beach Homes with Sailboat Water Water Frontage

Welcome to Madeira Beach, Florida, a charming coastal gem nestled in Pinellas County. Known for its stunning sunsets, pristine sandy shores, and vibrant community, Madeira Beach is the perfect destination for those seeking a laid-back lifestyle infused with the beauty of the Gulf of Mexico. With a unique blend of small-town charm and modern amenities, this picturesque city is a haven for beach lovers and water enthusiasts alike.

One of the most coveted features of Madeira Beach is its sailboat water frontage. Homes in this area offer direct access to the sparkling waters, making it a dream come true for boating aficionados and fishing enthusiasts. Imagine waking up to the gentle sound of waves lapping against your dock, with the sun rising over the horizon, ready to embark on a day of adventure. Whether you’re sailing to nearby islands or enjoying a leisurely cruise at sunset, the possibilities are endless.

The real estate market in Madeira Beach is diverse, offering a range of beautiful homes that cater to various tastes and budgets. From charming beach cottages to luxurious waterfront estates, each property is designed to maximize the breathtaking views and create a seamless indoor-outdoor living experience. With the convenience of local shops, delectable dining options, and vibrant community events just a stone’s throw away, life in Madeira Beach is as delightful as it is fulfilling.

If you’re looking for a place where coastal living meets community spirit, Madeira Beach is calling your name. Explore the possibilities of owning a home with sailboat water frontage and make your dream of waterfront living a reality!

Newest Madeira Beach Homes with Sailboat Water Water Frontage

$929,000
3 Beds 2 Baths Island Estates Unit 1 Sec A SubDv. 33708 Zip Code
Virtually Staged. BEACH, BOATING OR POOL? WHY CHOOSE WHEN YOU CAN HAVE ALL THREE! WELCOME TO YOUR PRIVATE WATERFRONT ESCAPE ON ISLAND ESTATES! Situated on a cul-de-sac street, this exceptional coastal retreat has been renovated from top to bottom. Start your morning with your favorite beverage overlooking the water, or step onto your private dock equipped with a 8,000 lb. boat lift with NEW cables and GEM REMOTES CONTROL BOX and set off for a quick ride to the Gulf! Spend the day cruising to sandbars, fishing the Gulf waters, or stopping at your favorite waterfront restaurant. Step inside your new home to a bright, open-concept floor plan featuring crown molding, shiplap ceilings, a skylight that brings abundant natural light into the living room, energy-efficient windows, plank-style tile flooring, and a wood-burning fireplace that adds warmth on those rare cooler evenings. The impressive kitchen showcases rich navy-blue cabinetry, sleek quartz countertops, a deep basin sink, elegant gold faucet and hardware, NEW stainless steel range, dishwasher, and microwave, a closet pantry, breakfast bar with pendant lighting, plus there’s additional cabinet storage in the oversized laundry room. Designed with privacy in mind, the split-bedroom layout places the primary suite with ensuite bath and the second bedroom and guest bath on one side of the home. Both bathrooms have been tastefully remodeled with a fresh, coastal-inspired design. The third bedroom overlooks the pool and water and a generous bonus room offers even more flexibility for a media room, game room, fitness area, hobby space, or whatever best complements your lifestyle. Additional highlights include a 5-unit mini-split A/C system, NEWER modified bitumen roof installed in 2023, NEW water heater in 2025, NEW pool pump motor installed August 2026, pavered driveway, converted garage ideal for storage or golf cart parking, plus an additional exterior storage room. Surrounded by mature tropical landscaping, the fenced backyard was created for relaxation, entertaining and making the most of Florida’s sunshine. Lounge on the sun shelf of the sparkling inground pool, gather with friends and family at the covered outdoor bar, or get cozy in your favorite chair on the expansive pavered patio and enjoy tranquil water views. This Island Estates location is hard to beat! Take a quick 5-minute walk to the area’s sugar-sand beaches, or explore nearby boutiques, restaurants, local pubs, and live entertainment. Hop on a golf cart, stroll, or ride your bike and enjoy an easygoing way to experience everything the area has to offer. Nearby attractions include fishing charters and ROC Park, featuring pickleball courts, outdoor events, and concerts, along with the famous John’s Pass Village & Boardwalk, where shops, dining, watersport rentals, music, and activities provide something for everyone. St. Pete-Clearwater International Airport is approximately 30 minutes away, while Tampa International Airport is about a 40-minute drive. Whether you're heading out for an early-morning boat ride to the sandbars, enjoying waterside dining or a sunset cruise, fishing the Gulf, spending the afternoon at the beach, or gathering poolside under the stars, this remarkable property puts the Florida waterfront lifestyle right outside your door. Discover a place where beach, boating, pool days, laid back living and Island charm come together to create an extraordinary place to call HOME!

403 Normandy Road, Madeira Beach

$999,800
3 Beds 2 Baths Madeira Shores 1st Add SubDv. 33708 Zip Code
Stunning inside. Deep water outside. Direct Gulf access. Minutes to everything you could want, all wrapped up in one beautiful package. Professionally designed and renovated from top to bottom, this 3 bedroom, 2 bath waterfront home is among the first to be brought to market. Renovations include new electrical, new HVAC, new water heater, and new engineered wood flooring throughout. The gorgeous kitchen features two tone wood cabinetry, ceiling-height uppers, and new stainless steel appliances. All three bedrooms are spacious, while the primary bedroom and one guest bedroom enjoy beautiful long water views. Both bathrooms are meticulously finished with sophisticated design and modern finishes. The open living area flows effortlessly into the dining area and waterfront family room, where you may just want to take a seat and admire the view. Step outside to relax on the shaded, screened patio, soak up some sunshine on the back deck, or head out to the dock. The 10,000-lb boat lift keeps your boat high, dry, and ready to head out on the water at a moment's notice. The oversized one-car garage offers even more functionality with a shower and washer/dryer hookups. This home is truly ready for you to kick off your shoes, relax, and live like you're on vacation. It's an opportunity to own a prime piece of waterfront in one of the best locations in Madeira Beach - just 500 steps (3 blocks) from the sugary sand of the Gulf beaches and only half a mile from Madeira Beach Town Center, with shopping, dining, and the coming-soon Legacy Beachmaker. Madeira Beach residents also enjoy the convenience of a free parking pass. Beautiful inside, deep water out back, and the beach just steps away. This is Madeira Beach living. With rebuilding and new construction continuing throughout Madeira Beach, this is an opportunity to get in early BEFORE more newly finished and new construction homes come to market and reset waterfront values higher.

360 145th Avenue E, Madeira Beach

$849,000
2 Beds 2 Baths Crystal Island 1st Add SubDv. 33708 Zip Code
Virtually Staged. One or more photo(s) was virtually staged. Wake up to breathtaking sunrises over the water, enjoy your morning coffee beneath the shade of mature trees, and set out for an unforgettable day on the Gulf, all from the comfort of home. Positioned along a serene, wide canal offering sailboat water and no fixed bridges, this beautifully renovated two bedroom, two bathroom residence blends timeless coastal charm with effortless waterfront living. Inside, a bright and open floor plan creates an inviting atmosphere for relaxed everyday living and easy entertaining. Beautiful shiplap accents throughout bring warmth, character, and a refined coastal feel, while plantation shutters add another layer of timeless style. The thoughtfully updated kitchen features all new appliances, and generously sized bedrooms provide peaceful places to unwind. Move in ready and beautifully refreshed, this home allows you to begin enjoying the waterfront lifestyle from the moment you arrive. Step outside to the tranquil, east facing backyard, where lush, mature trees provide welcome shade and privacy. A private boat dock and lift make it easy to step aboard and cruise toward the open Gulf whenever adventure calls. It is the perfect setting for quiet mornings, leisurely afternoons, and evenings spent enjoying the gentle coastal breeze. Additional improvements include a new water heater, updated electrical panel with a generator connection, and brand new garage door, offering added comfort, convenience, and peace of mind. Whether you are an avid boater searching for your next waterfront adventure or dreaming of a peaceful coastal retreat, this charming home invites you to slow down, soak up the sunshine, and embrace the Florida lifestyle you have been waiting for. Come discover your own slice of waterfront paradise, where every day feels like a getaway.

541 Lillian Drive, Madeira Beach

$2,599,000
4 Beds 3 Baths Crystal Island 2nd Add SubDv. 33708 Zip Code
STUNNING WATERFRONT residence in the exclusive Crystal Island enclave of Madeira Beach — a refined island retreat offering effortless indoor/outdoor living and direct deep-water access. Beautifully renovated, this 4-bedroom, 3-bath home (gross 4,800 sq. ft.) features an open floor plan that showcases breathtaking open-water views from nearly every living space. Perfect for boater enthusiasts and minutes to John’s Pass and the Gulf of Mexico, the property offers a 2018 Trex-deck dock with full power and water, a 35,000-lb lift and a 16,000-lb lift — deep water in a no-wake zone for large vessels and only a five-minute boat ride to John’s Pass and the Gulf. Thoughtfully appointed for entertaining, the lower level hosts a custom bar area with a beer fridge and ice maker, while the expansive rear patio includes an outdoor kitchen and grilling area. The chef’s kitchen features custom cabinetry, Quartz/Cambria countertops and newer stainless steel appliances overlooking the oversized back deck and waterfront. The spacious second-floor master suite offers a large walk-in closet and an en suite with a travertine shower and sunken tub. Luxury finishes include luxury vinyl flooring upstairs, solid wood doors, new hardware, 5" baseboards, crown molding and casings. Recent upgrades include new hurricane-impact sliders and windows throughout, New water softener system 2024, pool resurfaced 2022, new pool heater 2022, and a Hayward Pro-Grid water heater (2021). Notably, the home did NOT flood during Hurricane Helene. Enjoy island living in a friendly golf-cart community just 2 miles from Madeira Beaches sands. This is coastal luxury with unmatched waterfront lifestyle — schedule your private showing today.

503 Johns Pass Avenue, 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

$1,270,000
3 Beds 3 Baths Residences At Town Center Condo SubDv. 33708 Zip Code
Discover your coastal sanctuary at the Residences at Town Center on Madeira Beach, where refined luxury meets the effortless rhythm of Gulf front living. From the moment you arrive, you’ll feel the quiet exclusivity of this boutique waterfront community, perfectly suited for those seeking a sophisticated second home or a full-time escape by the sea. This penthouse residence offers a rare opportunity to wake each morning to shimmering water views and end each day with unforgettable sunsets from your private 28 foot balcony. Inside, the open-concept design is both elegant and inviting, featuring 10 foot ceilings, luxury vinyl plank flooring, and a double door entry that creates an immediate sense of arrival. The designer kitchen is beautifully appointed with gorgeous Quartz, solid wood cabinetry, and premium GE Café appliances. Perched on the top floor, this residence offers a level of privacy and unobstructed panoramic views that few can claim. Whether enjoying morning coffee as boats pass quietly below or unwinding beneath the colors of a Gulf sunset, this home offers a daily connection to the water that is both peaceful and inspiring. Life in Madeira Beach is defined by its authentic coastal charm. Residents enjoy miles of powder soft sand, warm Gulf waters, and a welcoming, unhurried atmosphere. Golf cart rides to dinner, sunset walks along the shoreline, and afternoons spent boating or dining at local waterfront restaurants become part of your everyday lifestyle. The recent addition of the Beachmaker Resort, part of the Marriott Autograph Collection, further enhances the area’s appeal, bringing a new level of luxury, fine dining, and long term value to this already sought after destination. At the Residences at Town Center, amenities are designed to complement this exceptional lifestyle. Enjoy the heated pool and spa, rooftop terrace with breathtaking 360 degree views stretching from the Gulf beaches to downtown St. Petersburg, private rooftop cabanas, fitness center, and marina. With just 27 residences, two secure under building parking spaces, plenty of guest and golf cart parking, and pet-friendly policies with no size restrictions, every detail has been thoughtfully considered. Whether you are seeking a luxurious winter retreat, an investment with strong rental flexibility, or a permanent waterfront residence, this penthouse offers a rare opportunity to own in one of Florida’s most desirable and evolving coastal communities. Schedule your private showing today and experience the effortless luxury of life on Madeira Beach.

400 150th Avenue Unit 504, 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

$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

$999,490
3 Beds 3 Baths The Residences At Town Center SubDv. 33708 Zip Code
WATERFRONT LUXURY UNDER $1 MILLION — MAJOR PRICE REDUCTION - Ready for immediate occupancy. Discover one of the final opportunities to own a brand-new, never-lived-in waterfront 3-bedroom, 3-bath ensuite residence in this exclusive 27-residence boutique community in the heart of Madeira Beach. Offered directly by the developer and available for immediate occupancy, this residence combines new-construction quality, waterfront living and exceptional value at a price point becoming increasingly difficult to find along Florida’s Gulf Coast. Unlike competing resale properties, this home has never been occupied and offers the opportunity to move in and enjoy the beach lifestyle without the need for renovations or updates. Residents enjoy an impressive collection of resort-style amenities, including a heated waterfront pool and spa, fitness center, club room, secure under-building parking and a spectacular rooftop terrace with panoramic views extending from the Gulf of Mexico to downtown St. Petersburg. Located in Madeira Beach’s highly desirable Town Center district, the residence is just steps from the beach, restaurants, bars, parks, shopping, marinas and the future Beachmaker Marriott Autograph Collection Resort. For boating enthusiasts, the developer also owns the adjacent marina, and boat-slip rentals may be arranged for purchasers of developer-owned residences, subject to availability, separate rental agreement and applicable terms. Enjoy the flexibility to use the property as a primary residence, second home or income-producing property, with rentals permitted subject to a 30-day minimum. Immediate occupancy may also make this an attractive option for buyers considering a potential 1031 tax-deferred exchange. Two pets are permitted, including large dogs. For buyers seeking brand-new construction, waterfront living, walkability, resort-style amenities, boating opportunities and flexible ownership below $1 million, this residence presents a rare combination of lifestyle and value. Aggressively priced to sell—schedule your private showing today and experience one of Madeira Beach’s final brand-new developer residences.

400 150th Avenue Unit 205, Madeira Beach

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