Location: Island Estates, Clearwater Beach
Do Not Show Listings
442 MIDWAY IS, CLEARWATER BEACH, FL 33767
$3,495,000344 Days on yellowkey MLS ID: TB8399954
REDUCED by $455,000 (11.5%) on 05/28/2026
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4039 Built: 2008 Tax: $19,718 (2024)Community: Island Estates Of ClearwaterSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$19,718
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: One-of-a-Kind Island Estates Waterfront Masterpiece Welcome to an extraordinary waterfront retreat in the prestigious and highly sought-after community of Island Estates. Perfectly positioned at the end of the island on deep, open water, this exceptional residence offers 150 feet of pristine water frontage, providing the ultimate haven for boating enthusiasts - with space to accommodate any size vessel you desire. From the moment you arrive, the home's curb appeal is undeniable. A welcoming driveway, beautifully manicured landscaping, and graceful palm trees create a peaceful, tropical setting. Thoughtfully constructed with superior craftsmanship, this elevated Key West-style home rests atop nearly 50 reinforced pilings, offering lasting strength, security, and peace of mind against Florida's coastal storms. Spanning over 9,000 total square feet (4,000 square feet under air) across three thoughtfully designed levels, this property offers versatility, luxury, and space in abundance. The ground level includes two separate garages and an enormous storage area - ideal for multiple uses such as a gym, workshop, hobby space, or simply an incredible amount of storage for all your toys and gear. On the main living level, a wrap-around veranda welcomes you to relax and take in the endless water views. Step inside to soaring 20-foot ceilings, walls of windows (nearly 100 in total!) and gleaming Brazilian cherry wood floors that create warmth and elegance throughout the space. Wherever you stand, you're greeted by breathtaking water vistas - it's impossible not to be inspired by the beauty surrounding you. The heart of the home is the expansive, open-concept great room and gourmet kitchen, designed for both entertaining and everyday living. A beautifully appointed wet bar makes hosting friends and family effortless. For more formal gatherings, enjoy the elegant dining room or unwind in the charming sitting room/parlor. A private guest suite with its own en-suite bath completes this level, offering comfort and privacy for visitors. Upstairs, the primary suite is a true retreat - complete with vaulted cathedral ceilings, a private balcony overlooking the water, and a recently renovated, spa-inspired en-suite bathroom featuring luxurious finishes, an oversized walk-in shower, soaking tub, and dual vanities. The custom wrap-around closet offers exceptional storage and organization. Three additional bedrooms, each with either an en-suite or Jack-and-Jill bathroom, ensure that every family member or guest has their own private haven- and each has a balcony with captivating water views. And for the grand finale - ascend to the one-of-a-kind rooftop sun deck, thoughtfully engineered to support a hot tub if desired. From this exclusive perch, enjoy unmatched 360-degree views of Island Estates, the Intracoastal Waterway, and Clearwater Beach - truly the best view in town. Whether savoring sunsets, hosting gatherings, or simply soaking in the peaceful surroundings, this private rooftop escape is unforgettable. With deep water access, robust construction, designer finishes, endless storage potential, and panoramic views from every corner of the home, this Island Estates masterpiece is a rare and exceptional offering - where luxury, comfort, and coastal living come together in perfect harmony.
Listing is courtesy of: CENTURY 21 BE3 (727-596-1811)
Listing Agent: Prudy Cole (863-397-7305)
670 ISLAND WAY #304, CLEARWATER BEACH, FL 33767
$935,000109 Days on yellowkey MLS ID: TB8472962
REDUCED by $40,000 (4.1%) on 04/08/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 2142 Built: 1997Community: Sunwatch On Island EstatesCondo
Taxes:$0
Tax Year: 2025
Remarks: Seller is offering a substantial buyer incentive at closing equal to 9 months of current HOA dues (over $12,900 in value) providing extra flexibility for closing costs, reserves, or future updates. The seller is motivated and ready to negotiate. Interior is freshly painted, all new luxury vinyl flooring and new baseboards. The kitchen and bathrooms provide an excellent opportunity to personalize the home while building equity in one of Island Estates' most sought-after waterfront communities. Sunwatch has completed its Milestone Inspection and Structural Integrity Reserve Study, with major improvements including a new roof and exterior painting completed in 2024. Residents enjoy resort-style amenities including two pools, heated spa, fitness center, tennis and pickleball courts, guest suites, clubhouse, marina access, secure entry, and under-building parking. Minutes to Clearwater Beach, Publix, dining, shopping, and the Jolley Trolley. Exceptional waterfront living with outstanding value and endless potential.
Listing is courtesy of: SILVER ROOTS REAL ESTATE GROUP (727-288-0142)
Listing Agent: Sandra Ceballos (727-424-5443)
231 MIDWAY IS, CLEARWATER BEACH, FL 33767
$3,590,000250 Days on yellowkey MLS ID: TB8431098
REDUCED by $50,000 (1.4%) on 06/02/2026
Bed: 3 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 4509 Built: 2015 Tax: $35,251 (2024)Community: Island Estates Of ClearwaterSpa: YesSingle Family
Taxes:$35,251
Elementary School: Sandy Lane Elementary-PN
High School: East Lake High-PN
Middle School: Dunedin Highland Middle-PN
Remarks: Experience refined coastal living with just the right amount of Florida flair in this elegant Spanish Mediterranean waterfront residence, perfectly positioned on the sparkling Intracoastal waters of Clearwater Bay. Think luxury, sunshine, salt air, and enough waterfront charm to make your friends suddenly “available” every weekend. Move-in ready and partially furnished with curated Restoration Hardware pieces, this home makes stepping into the coastal lifestyle almost too easy. From the moment you enter, you’re greeted by bright, airy spaces filled with natural light and elevated by extensive custom millwork, including coffered ceilings, layered crown molding, tray ceilings, detailed wainscoting, and the kind of craftsmanship that quietly says, “Yes, this home has excellent taste.” A private elevator services each level, adding everyday convenience with a polished luxury touch. The gourmet kitchen is truly the heart of the home, thoughtfully designed for entertaining, everyday living, and pretending your morning coffee tastes better because you’re drinking it by the water, spoiler alert, it probably does. Custom solid wood cabinetry with seeded glass accents, granite countertops and full backsplash, a spacious breakfast bar, farmhouse sink, and premium appliances create a kitchen that is both stunning and highly functional. Features include a six-burner Wolf range with pot filler, Sub-Zero refrigerator, dishwasher, built-in microwave, ice maker, beverage fridge, and wine fridge, because in Florida, hydration is important and sometimes it comes chilled. A charming eat-in nook offers the perfect spot for sunrise coffee, casual meals, or evening wine while watching the sky do that gorgeous Clearwater thing. The main level also includes a beautifully appointed half bath for guests and a luxurious primary suite designed as a private waterfront retreat. The spa-inspired primary bathroom features dual vanities, a freestanding soaking tub, and a separate walk-in shower, creating a peaceful space to unwind after a day on the boat, at the beach, or simply supervising the sunset. Three closets provide exceptional storage, including a versatile dressing room that was formerly a private office with its own entrance, easily converted back depending on whether your wardrobe or your work-from-home life needs more space. Upstairs, two additional bedrooms each feature their own en suite bath and walk-in closet, offering comfort and privacy for family and guests alike. It is the perfect setup for visitors who come for “just a few days” and then remember they love Clearwater. Elegant, move-in ready, partially furnished, and set along one of Florida’s most beautiful waterfront backdrops, this home delivers the luxury coastal lifestyle people dream about, with no filter required.
Listing is courtesy of: IMPACT REALTY TAMPA BAY (813-321-1200)
Listing Agent: Becky Billeci (925-383-5760)
330 LEEWARD IS, CLEARWATER BEACH, FL 33767
$2,375,000176 Days on yellowkey MLS ID: TB8451016
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2749 Built: 1958 Tax: $36,530 (2024)Community: Island Estates Of ClearwaterSpa: NoSingle Family
Taxes:$36,530
Remarks: Discover the best of Florida waterfront living at 330 Leeward Island, a spacious and inviting residence positioned along the Intracoastal Waterway in Island Estates. This single-story home features 4 bedrooms, 3 full bathrooms, and 2,749 square feet of interior living space designed for comfort, natural light, and year-round enjoyment of the coastal environment. Located on a deep waterfront lot, the property offers direct boating access and an ideal setting for outdoor living. Inside, the home offers an open and flowing floor plan with multiple gathering spaces, including a formal living area, family room, and a dining space adjacent to the kitchen. Large windows, sliding doors, custom shiplap, level 5 drywall finish on both walls and ceilings, Anderson Tuftex Engineered Hardwood floors and a bright interior color palette accentuate the stunning water views. The chef inspired kitchen exudes unparalleled sophistication featuring expansive counter space and a striking center island finished in Cristallo Gold quartzite, with fully LED-backlit luminescence seamlessly controllable via Bluetooth. A sleek, updated ZLINE appliance package in a stainless- black monochromatic finish complements the premium white oak cabinetry, culminating in a truly high-end, modern culinary masterpiece. A split-bedroom layout provides privacy, while additional features such as a gas fireplace and wet bar enhance the home’s functionality. Step outside to your own private retreat featuring a heated saltwater pool surrounded by tropical landscaping and extensive travertine marble pavers. The covered patio offers the perfect place for outdoor dining or relaxing while enjoying the waterfront setting. The private dock - 2022 - complete with 2 boat lifts - the lift under the boathouse is 16,000 lbs, the other lift is an 4,000 lb lift-ideal for a skiff, jet ski(s) or paddle boards! The two-car garage with workshop space and ample driveway parking just adds to the convenience of this waterfront lifestyle. Premium Galvalume metal standing seam roof - 2021. Island Estates is one of Clearwater Beach’s most desirable neighborhoods, known for its walkability, golf-cart access, and proximity to shopping, dining, marinas, and the beach. With no HOA and a rare combination of indoor comfort and waterfront amenities, this home is ideal as a primary residence, second home, or investment property. Buyers should verify flood insurance requirements based on current zoning. This is a standout opportunity to secure a waterfront lifestyle in a prime coastal location.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Tanner Tillung (727-479-4548)
707 SNUG IS, CLEARWATER BEACH, FL 33767
$1,875,00073 Days on yellowkey MLS ID: TB8489063
REDUCED by $25,000 (1.3%) on 05/19/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2997 Built: 1970 Tax: $12,033 (2025)Community: Island Estates Of Clearwater Unit 7BSpa: NoSingle Family
Taxes:$12,033
Remarks: WATERFRONT LIVING AT ITS BEST! Experience the ultimate in tropical luxury with this stunning 2-story waterfront home. Offering 2 car garage, 3 spacious bedrooms, 3 full bathrooms, and a stylish half bath. The first floor en-suite features an attached living room for an in law arrangement, home office or even a live in nanny. Featuring hickory hardwood floors throughout, this residence blends contemporary design with warm, natural tones for effortless coastal charm. Enjoy resort- style living with a oversized pool, outdoor kitchen with built-in seating, and lush surroundings perfect for entertaining or relaxing in privacy. The homes 2023 new roof and 2021 flat roof provide peace of mind, while PGT impact windows and a whole-house water system ensure comfort and security. Inside, the 2024 kitchen remodel showcases refined craftsmanship with modern finishes and premium appliances. The kitchen opens to the combined living room dining room with vaulted ceilings. Freshly painted exterior, every detail has been thoughtfully updated for a move- in -ready experience that feels brand new. The second floor features 2 more bedrooms with attached baths. The primary retreat has a huge walk in closet, double sinks with custom vanity, soaking tub with jets and a walk in shower. The primary retreat also has a huge balcony to enjoy your morning coffee while catching every sunrise. This home also features a large dock with 10,000lbs boat lift. Located on Island Estates, there is a Publix grocery, post office and gas station along with fine dining and all a short stroll to our famous Clearwater Beach. This Property sits high and dry, didn't flood! This property captures the essence of coastal sophistication, elegance, low maintenance, and designed for those seeking the ultimate in Island Life. BE SURE TO CHECK OUT MY VIRTUAL TOUR
Listing is courtesy of: CHARLES RUTENBERG REALTY INC (727-538-9200)
Listing Agent: Mary Donovan, Pa (727-560-1985)
430 PALM IS SE, CLEARWATER BEACH, FL 33767
$1,999,00082 Days on yellowkey MLS ID: TB8484148
REDUCED by $225,000 (10.1%) on 05/07/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2780 Built: 1968 Tax: $9,713 (2025)Community: Island Estates Of Clearwater Unit 6-ASingle Family
Taxes:$9,713
Remarks: One or more photo(s) has been virtually staged. Experience the ultimate Florida beach and boating lifestyle in this stunning waterfront home located in the exclusive community of Island Estates. A true boater’s paradise, this exceptional property offers effortless access to the Intracoastal Waterway and the sparkling waters of the Gulf of Mexico. Skip the stress of marinas and boat trailers — simply step outside and head straight to the water whenever you choose. With room for your boat, jet skis, and all your waterfront toys, every day feels like a vacation. Spanning 2,780 square feet, this beautifully updated residence features 4 spacious bedrooms and 3½ baths with a bright open floor plan designed for entertaining and everyday living. The chef’s kitchen is the heart of the home, complete with island bar seating, brand-new Bosch gas range, refrigerator, and dishwasher (2025), and seamless flow into the living and dining areas. Extensive upgrades completed in 2025 include a new metal roof, thoughtfully designed room addition, solid wood triple crown molding, expanded primary closet, additional bedroom and bath, new entryway, and a stylish coffee/wet bar. New flooring throughout the home, excluding tile, creates a fresh modern feel, while a new Maytag washer and gas dryer add convenience. Designed for relaxation and entertaining alike, the outdoor living spaces are ideal for hosting unforgettable weekends and gatherings with family and friends. The expansive patio features a built-in outdoor grill and bar, creating the perfect setting after a day on the water. Boating enthusiasts will appreciate the dock installed in 2020 with all new pilings, along with two boat lifts — a 16,000 lb lift (2020) and a 9,000 lb lift (2015) — making it easy to keep multiple vessels ready for sunset cruises or fishing adventures. Located just minutes from the white sands of Clearwater Beach, this exceptional property offers the rare opportunity to enjoy luxury waterfront living with direct boating access and world-class beaches nearby.
Listing is courtesy of: COASTAL PROPERTIES GROUP INTERNATIONAL (727-493-1555)
Listing Agent: Lindsay Irwin (603-969-6132)
136 WINDWARD IS, CLEARWATER BEACH, FL 33767
$1,690,000109 Days on yellowkey MLS ID: TB8475218
REDUCED by $59,000 (3.4%) on 05/30/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2390 Built: 1964 Tax: $14,913 (2024)Community: Island Estates Of ClearwaterSingle Family
Taxes:$14,913
High School: Clearwater High-PN
Remarks: FULLY REMODELED, TWO BOAT LIFTS, GREAT VALUE WATERFRONT ISLAND ESTATES HOME! Welcome to 136 Windward Island, located in the desirable community of Island Estates in Clearwater Beach, this beautifully remodeled 5-bedroom, 3-bath waterfront home offers nearly 2,400 heated square feet of well-designed living space on an oversized lot with 84 linear feet of waterfront and western exposure for sunset views. The home welcomes you through a new double-door entry, opening to expansive water views that extend through the main living areas toward the pool and outdoor living space. The open layout is ideal for both everyday living and entertaining. The gourmet kitchen features a large center island, granite countertops, and solid wood cabinetry, and flows seamlessly into the spacious family room with custom built-ins and an ideal space for a TV or fireplace. Hurricane-rated windows and sliding glass doors enhance natural light while providing added durability and storm protection. The primary suite includes an upgraded ensuite bath with double vanities, a remodeled shower, and updated plumbing (2019). Additional improvements include luxury vinyl flooring, new AC units (2019), and a hurricane-rated garage door (2019). Outdoor living is highlighted by an extra-large pool, a waterfront seating area along the seawall, and a DOCK with two boat lifts, which have bern updated with 2 new motors and belts and Electric panel, offering convenient boating access and protected mooring. Island Estates offers close proximity to Clearwater Beach, along with nearby restaurants, grocery stores, banks, and everyday conveniences closeby, providing a well-rounded coastal lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (727-581-9411)
Listing Agent: Michelle Chenault (727-481-5700)
354 LARBOARD WAY, CLEARWATER BEACH, FL 33767
$1,320,00018 Days on yellowkey MLS ID: TB8503358
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2975 Built: 1998Monthly Fee: $200 Tax: $10,163 (2025)Community: Island Estates - Dolphins LandingSpa: NoTownhouse
Taxes:$10,163
Elementary School: Sunset Hills Elementary-PN
Remarks: Luxury Island Living Without the Work – Island Estates. Welcome to a rare opportunity to enjoy the space and privacy of a nearly 3,000 sq ft luxury home—without the time, cost or upkeep typically required to maintain one. Perfectly positioned in sought-after Island Estates, this exceptional home delivers the space and convenience of single-family residence with the ease of low maintenance living – an exceptional opportunity in today’s Clearwater Beach real estate market. With HOA fees of just $200 per month, you’ll save over $1,000 per month compared to nearby condos—enough to fund an annual luxury vacation. Even better, enjoy no surprise assessments, providing true peace of mind. Add in current homeowners’ insurance just a little over $3,000, a $200 average electric bill and $130 monthly water bill, this property delivers exceptional value – especially when compared to nearby condos and similar properties. Designed for effortless living, this home offers no yard work, shared building maintenance, and a 2 car enclosed garage. A boating friendly community with a shared waterfront area, ideal for fishing, kayaking and paddleboarding, along with community boat slips (not included with this unit); this home gives you all the perks of waterfront ownership with none of the hassle. The house was renovated in 2026 with new paint throughout and high-quality luxury vinyl plank flooring in the primary suite and hallways, reflecting a significant investment and creating a clean, modern coastal feel. Inside, you’ll find beautiful upgrades throughout, generous living spaces, and plenty of storage, like his and her closets, double closets in both bedrooms, garage racks, a large attic and an enclosed garage that doubles as a gym. The pocket sliding glass doors open to a private lanai, with remote-controlled awning, doubling your entertaining space. This expansive space is ideal for dining, relaxing and hosting, and includes built-in cabinetry and countertops designed for effortless outdoor dining and entertaining. Beyond the terrace, an additional private patio offers even more room to grill (no waiting in line for a shared condo grill) and gather with friends while enjoying the surrounding coastal setting. Upstairs, the primary suite offers a private retreat with its own screened balcony. Wake up to tranquil water views and unwind with stunning sunsets in the evening, creating a serene and private escape. The spacious layout features 2 large walk-in closets with custom built-ins and a well-appointed ensuite bath. One of the guestrooms includes hidden office space and connects via a Jack-and-Jill bathroom to a second bedroom, offering flexibility for working from home, room for guests, or additional living space. For added peace of mind, the home is equipped with electric hurricane shutters on all windows and doors, and reinforced garage door bracing, and has not experienced any flooding. As an added bonus, the seller is offering a $5,000 credit at closing to reimagine any space, with select furnishings that are negotiable – creating a truly turnkey opportunity. Just minutes from world-famous Clearwater Beach, trendy restaurants, and vibrant entertainment venues—yet tucked away in the serene Island Estates community, this is luxury coastal living—water views, all the space, expansive outdoor living, none of the stress. Schedule your private showing of 354 Larboard Way and start living the coastal lifestyle you deserve.
Listing is courtesy of: EXP REALTY (727-449-9276)
Listing Agent: Kathie Lea (727-422-9455)
824 ISLAND WAY, CLEARWATER BEACH, FL 33767
$3,700,00092 Days on yellowkey MLS ID: TB8481851
Bed: 6 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4934 Built: 2005Monthly Fee: $4 Tax: $63,372 (2025)Community: Island Estates Of ClearwaterSpa: YesSingle Family
Taxes:$63,372
Remarks: Your waterfront dream home awaits at 824 Island Way. Perfectly positioned on the open water side of Island Estates, this nearly 5,000-square-foot custom-built Mark Maconi residence delivers luxury coastal living with two spacious primary suites and an exceptional list of recent upgrades. The home now showcases a freshly painted exterior with a refined Mediterranean flair, complemented by new exterior lighting that enhances its architectural detail and evening curb appeal. Additional improvements include a stunning tile roof, solar panel system, two 16-foot sliding glass door systems, and two extended composite decks that expand your outdoor living space and maximize the stunning waterfront views. A floating dock was also added in 2021. Step through the grand foyer and take in sweeping views across the Mandalay Channel toward the Gulf of America. Custom plantation shutters add elegance throughout, while the main-floor study features built-in shelving and can easily serve as a sixth bedroom. A well-appointed butler’s bar with a built-in wine refrigerator sits conveniently near the private elevator. The chef’s kitchen is designed for entertaining and everyday ease, offering a large island, Viking gas range, stainless steel appliances, built-in oven and microwave, and a central vacuum system. Upstairs, a thoughtful split floor plan provides privacy for two impressive primary suites. The main suite features an oversized bath with a walk-in shower, separate floating tub, built-in shelving, dual vanities leading to one private water closet on the right with a washer/dryer closet on the left, and a generous walk-in closet. Private east- and west-facing balconies offer breathtaking sunrise and sunset views. The secondary suite includes a wet bar, two closets, a full bath with double vanities and walk-in shower, plus a private office that opens to its own balcony. Three additional bedrooms, two bathrooms, an oversized laundry room, and abundant storage complete the second level. Outdoor entertaining is effortless with a heated saltwater pool with full automation controlled via smartphone app, outdoor kitchen and grill. The refurbished dock features a 16,000-pound lift and a deep-water slip accommodating vessels up to 70 feet. The three-car garage houses the tankless water heater system, Air Vac filtration system, and the complete Enphase solar battery backup system. Elevated above many neighboring homes with a 12 foot elevation, this property benefits from reduced flood insurance costs and added peace of mind with its solar power system—essentially functioning as a built-in generator. Located in the coastal Island Estates community, home to Clearwater Marine Aquarium, residents enjoy close proximity to Island Way Grill, Publix, and the world-famous shores of Clearwater Beach. Discover your private waterfront sanctuary at 824 Island Way—where dolphins play just beyond your dock and spectacular Gulf Coast sunsets are part of your everyday view.
Listing Agent: Kathy Grams (727-259-9247)
207 MIDWAY IS, CLEARWATER BEACH, FL 33767
$2,349,900126 Days on yellowkey MLS ID: TB8467513
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4172 Built: 1964Monthly Fee: $4 Tax: $8,351 (2025)Community: Island Estates Of ClearwaterSingle Family
Taxes:$8,351
Remarks: Indulge in Coastal Opulence at 207 Midway Island! Prepare to be captivated by the allure of Island living with this extraordinary property now available for sale on the prestigious Island Estates. Nestled amidst the sparkling waters of the Intercoastal Waterway, this 4 bedroom 4 bath stunning residence offers a rare opportunity to own a slice of paradise unlike any other. From the moment you arrive, you'll be swept away by the spaciousness of this home at over 4,000 square feet situated on an expansive waterfront lot. This estate boasts panoramic views of the Intercoastal, offering a front-row seat to dolphins playing and breathtaking sunrises. Step inside to discover a world of water views from every room. With an open concept master retreat upstairs you can walk out to a large deck and enjoy looking over the waterway and pergola downstairs. The master suite features spacious his and her own walk-in closets along with a large master bath, plus the benefit of additional room - perfect for a nursery or craft room. Every detail of this home has been meticulously designed to provide the utmost in comfort, storage, and style. Whether you're hosting lavish gatherings or enjoying the quiet of relaxation, this residence offers the perfect setting for every occasion. Conveniently located just a 10-minute walk to Clearwater's #1 beach, famous Clearwater Marine Aquarium, shopping centers, etc. This property offers the perfect blend of privacy and convenience. Whether you're seeking a serene retreat away from the hustle and bustle of the beach, or a luxurious waterfront escape to call your own, 207 Midway Island embodies the epitome of coastal living! Don't miss out on the opportunity to make this exquisite estate your new home. Contact us today to schedule a private tour and experience the unparalleled beauty and luxury that awaits you at 207 Midway Island - your island paradise awaits!
240 WINDWARD PSGE #1001, CLEARWATER BEACH, FL 33767
$359,00046 Days on yellowkey MLS ID: TB8498732
REDUCED by $40,000 (10.0%) on 05/08/2026
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1728 Built: 1982Monthly Fee: $1,139 Tax: $2,486 (2025)Community: Village On Island EstatesSpa: NoCondo
Taxes:$2,486
Remarks: Opportunity awaits at 240 Windward Passage, Unit 1001, a spacious multi-level residence perfectly positioned in the exclusive Island Estates community. This property represents the ultimate "blank canvas" for an investor or a visionary homeowner looking to create a custom coastal masterpiece just moments from the world-renowned sands of Clearwater Beach. While the home requires a full cosmetic rehab, its bones offer incredible potential, featuring soaring vaulted ceilings that flood the main living area with natural light and a rare, oversized two-car garage with a bonus flex space. With private balconies off the bedrooms and a location within walking distance of fine dining, shopping, and the Clearwater Marine Aquarium, this is a rare chance to sweat-equity your way into one of Florida’s most desirable zip codes. Bring your contractor and your imagination to unlock the true value of this premier island retreat.
Listing is courtesy of: CIGAR CITY REALTY LLC (813-468-8109)
Listing Agent: Michael Olivera (813-420-5593)
240 WINDWARD PSGE #1004, CLEARWATER BEACH, FL 33767
$675,00015 Days on yellowkey MLS ID: TB8509508
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2062 Built: 1982 Tax: $9,090 (2025)Community: Village On Island EstatesTownhouse
Taxes:$9,090
Remarks: Come enjoy the Florida Lifestyle you deserve in this elegantly designed townhome on Island Estates. Beautifully decorated Entryway invites you to the second floor that features a living room, dining area, kitchen, den/bonus room, laundry room, & half bath. Gorgeous porcelain flooring showcases the second floor living area. Enjoy relaxing in the living room in front of the electric fireplace, or enjoy grilling out on the balcony deck. The kitchen features imported Italian Cucina glass front cabinets with 2 slide out pantries, quartz counter tops, Gaggeneau in-counter steamer, stainless steel refrigerator & Samsung split oven range (2015), & porcelain tile, & Breakfast Bar. The laundry room is off the kitchen. The powder room has stunning blue glass tile & Antonio Lupi molded sink. The den has cork flooring, crown molding & a balcony. Go up the newer spiral staircase to the third floor features the master bedroom with oak flooring, crown molding, his & her closets, a window seat & balcony. The master bath has walk in shower and dual vanity quartz countertop. The third bedroom features ash wood flooring & built-in workstation & yes another balcony that is shared with the 2nd bedroom. The bath has Robern slide-up/lighted cabinets, Agape sink & recessed lighting over the tub. The bathrooms are European designed, featuring German Duravit toilets & Hansgrohe fixtures/faucets. Other upgrades are solid wood doors & water heater in 2015, Trane a/c & air handler (2024), water conditioner/purifier, & newer light fixtures. Miami code rated garage door (2015) & windows installed in 2011. 2 car garage with a 10x25 workshop. deep water boat slips (as available) & 2 community pools. The building exterior was painted & driveways resurfaced in 2016. Roofs were replaced about 7 years ago. Price includes all furniture as displayed. Come enjoy Clearwater Beach, famous for its sugar sand beaches, vibrant atmosphere, nightlife, retaurants & gorgeous sunsets!
Listing is courtesy of: FLORIDA WEST COAST HOMES, LLC (727-234-0950)
Listing Agent: Lynn Rice (727-234-0950)
450 PALM IS NE, CLEARWATER BEACH, FL 33767
$2,290,000110 Days on yellowkey MLS ID: TB8468677
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2783 Built: 1967 Tax: $24,739 (2025)Community: Island EstatesSpa: YesSingle Family
Taxes:$24,739
Remarks: Wake up to breathtaking sunrises and unwind with unforgettable sunsets from this premier deep-water estate on one of Island Estates’ most coveted cul-de-sacs in Clearwater Beach. This 4 bedroom, 3 bath waterfront residence sits on a rare lot with spectacular open water views, a covered boat lift for larger vessels, a dual PWC drive on jet ski lift, and a resort-style pool and spa designed for year round coastal living. Notably, no water entered the home during recent storms, offering added peace of mind. Inside, a bright vaulted living area with a stunning two-sided fireplace creates the perfect space for gathering and entertaining, complemented by a flowing layout, large bedrooms, wind-rated windows, and a spacious three-car garage. Whether you choose to personalize this beautiful home into your ultimate waterfront retreat or take advantage of the premier lot to build a brand new luxury residence, the opportunity is exceptional. Just minutes from world famous Clearwater Beach, enjoy powder soft sand, amazing waters, top-rated dining, vibrant nightlife, boating, fishing, and endless outdoor activities this is Florida coastal living at its absolute finest!
Listing is courtesy of: ENGEL & VOLKERS BELLEAIR (727-461-1000)
Listing Agent: Kristin Hallamek (727-642-7985)
511 WINDWARD PSGE, CLEARWATER BEACH, FL 33767
$2,999,000117 Days on yellowkey MLS ID: TB8472453
3 Days Off yellowkey (back on 5/12/2026)
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 5006 Built: 1959 Tax: $19,315 (2024)Community: Island Estates Of ClearwaterSpa: YesSingle Family
Taxes:$19,315
Remarks: Under contract-accepting backup offers. Wake up to the island life, where every day feels like vacation. Set on an oversized lot with 179 feet of pristine waterfront, this Island Estates retreat lives like a private resort with a sparkling PebbleTec pool and spa, a putting green for short-game practice, and a deep-water dock featuring a covered boat lift plus a combo lift for personal watercraft. Trade traffic for palm-lined bike rides to world-famous Clearwater Beach, or cast off from your backyard and cruise straight to dinner at your favorite waterfront restaurant. Inside, more than 5,000 square feet of thoughtfully updated living space blends coastal luxury with everyday comfort. A sunlit foyer opens to grand, airy gathering spaces and a chef’s kitchen finished with Viking appliances, marble countertops, and classic subway tile. The split layout ensures privacy for the primary suite, where a spa-inspired bath and a breezy balcony set the scene for morning coffee above the water. Take the elevator upstairs to multiple en-suite bedrooms and a versatile 20×23 bonus room—perfect for a media lounge or game room. Whether you’re lounging by the pool, practicing putts between swims, or launching kayaks from the dock, the backyard is designed for pure Florida fun. With effortless boating access, an easy walk or bike ride to the beach, and every island convenience just minutes away, this property defines the Clearwater waterfront lifestyle—polished, playful, and perfectly positioned to enjoy it all.
Listing Agent: Kerryn Ellson (727-408-4888)
451 PALM IS NE, CLEARWATER BEACH, FL 33767
$2,494,900121 Days on yellowkey MLS ID: TB8471225
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3086 Built: 1978 Tax: $22,896 (2025)Community: Island EstatesSingle Family
Taxes:$22,896
Remarks: Elegant Waterfront Home on prestigious Island Estates offers Florida lifestyle at its best! The home sits at the end of beautiful Palm Island, safely elevated high above the water line (no flooding). The 5-bedrooms 4-baths home is filled with sunlight and offers an open concept living with beautiful water views. Welcome your guests …to gather in the elegant 2-story open ceiling living room …. or to sip a Prosecco on the upstairs balcony overlooking the water ….or to get cozy around the woodburning fireplace. Outside you are greeted by a lush green front yard, an elegant driveway, a sparkling saltwater pool, a large pool deck to watch the dolphins come by, and a brand-new dock and boat lift for your dreamboat. The waterfront has deep water access that welcomes every type of boat and sits right on the intracoastal waterways that take you out to Gulf. Whether you're looking for a full-time waterfront residence or a seasonal getaway, this easy to maintain property has it all. Upgrades include 2 new HVAC systems to cool down the summer heat, impact rated doors and windows for peace of mind during storm season, new impact rated garage door, new custom kitchen with granite countertop, new stainless-steel appliances, new bathrooms, new pool pump, pool and much more. Irrigation is supported by reclaimed water with new pipes and sprinkler heads. Clearwater Beach is an all-year-round Gulf coast paradise with beautiful white sandy beaches, clear turquoise water and a family friendly atmosphere. Luxurious hotels, trendy restaurants, The Sound concert venue, bars with live music and the famous Pier 60 with its nightly vendors and performers, will keep you entertained! The TampaBay area offers endless elegant Golf courses, adorable beach towns, museums, sport venues and top health care facilities. This waterfront property is only 30min from TPA Tampa International Airport and easy to reach from all over the US and Europe. Call us today for your private showing!
Listing is courtesy of: NEDWED REAL ESTATE (310-801-0288)
Listing Agent: Katinka Nedwed (310-801-0288)
311 ISLAND WAY #203, CLEARWATER BEACH, FL 33767
$569,00075 Days on yellowkey MLS ID: TB8488135
0 Days Off yellowkey (back on 4/24/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1367 Built: 1971 Tax: $7,374 (2025)Community: Bay Island Condo Island EstatesCondo
Taxes:$7,374
Remarks: Under contract-accepting backup offers. Welcome to Island Estates — where your boat is practically your second front door. This beautifully updated 2-bedroom, 2-bath condo offers 1,367 sq ft of coastal living with a deeded boat slip featuring a 10,000 lb lift with new motors and controller, accommodating vessels up to 30 feet — all just steps from home. Inside, you’ll find brand new flooring, a newly updated kitchen with granite countertops, a brand new primary bath, plantation shutters, and two private balconies to soak in that Island Estates air. During the holiday's, you can enjoy the During the holidays, you can enjoy the annual Christmas boat parade from the comfort of your living room! The new central AC system (2024) keeps everything comfortable year-round. And for those looking for a truly seamless move — the unit may be available fully furnished, making this an effortless turn-key opportunity whether you’re relocating, investing, or simply ready to start living the Florida dream from day one. The complex itself has been fully renovated — new flat roof (2025), new gutters and downspouts, new exterior lighting, fresh landscaping, and new stairs and rails — with all assessments paid through 2026. HOA covers flood insurance and water, and the quiet 8-unit building means you’ll actually know your neighbors. Trolley stop right in front of Publix, a 3-minute walk to groceries, and Clearwater Beach just a short ride away. This is the Florida lifestyle; turnkey, low-maintenance, and ready for your next season.
Listing is courtesy of: AGILE GROUP REALTY (813-569-6294)
Listing Agent: Colleen Ramirez (845-453-5327)
350 HARBOR PSGE, CLEARWATER BEACH, FL 33767
$1,999,00077 Days on yellowkey MLS ID: TB8487226
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3366 Built: 1971 Tax: $8,145 (2025)Community: Island EstatesSpa: NoSingle Family
Taxes:$8,145
Elementary School: Plumb Elementary-PN
Remarks: One or more photo(s) has been virtually staged. Experience true Florida waterfront living in this elevated lot which had NO FLOODING in last major storms. This beautiful property is a spacious 3,366 sq ft residence featuring 4 bedrooms, 3.5 baths, and a private pool overlooking the water. Light-filled interiors offer generous living and entertaining spaces, including a large kitchen with direct access to the pool deck for seamless indoor-outdoor living. The adjoining dining and living areas are complemented by a versatile bonus space ideal for a home office or additional family room, along with a secondary flex room near the garage. It is a blank canvas ready for you to make your own. The primary suite provides a private retreat with en-suite bath, while upstairs, two guest bedrooms open to a shared balcony—perfect for enjoying coastal breezes and water views. Outdoors, enjoy a private dock with davit lift option, offering easy access to boating, fishing, and sunset cruises. The expansive patio and pool area are ideal for entertaining. An oversized 2-car garage includes a convenient half bath serving the pool area. A rare opportunity to own a spacious waterfront home in sought-after Island Estates—close to Clearwater Beach, dining, and shopping.
301 MIDWAY IS, CLEARWATER BEACH, FL 33767
$2,399,000253 Days on yellowkey MLS ID: TB8430210
0 Days Off yellowkey (back on 3/27/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 4176 Built: 1997 Tax: $25,387 (2024)Community: Island Estates Of ClearwaterSingle Family
Taxes:$25,387
Remarks: Experience the pinnacle of turnkey coastal luxury in this fully furnished architectural masterpiece, where modern sophistication meets enduring resilience. Offered complete with all designer-selected furniture, bespoke décor, and high-end fittings, this exceptional tri-level estate is truly move-in ready—an extraordinary opportunity for the discerning buyer or savvy investor seeking immediate income potential with zero compromise. Fully upgraded and meticulously curated to the highest standards, the residence is constructed to current flood elevation requirements, providing remarkable peace of mind. Having remained completely unscathed by two recent storms, the home stands as a testament to superior craftsmanship and structural integrity. Upon arrival, you are welcomed into a breathtaking great room crowned by soaring 20-foot ceilings and bathed in natural light. A custom-built mahogany bar with seating for six and a temperature-controlled wine chiller anchors the space, creating an entertainer’s showpiece designed for unforgettable evenings. Every furnishing has been thoughtfully selected to complement the home’s architectural grandeur, enhancing both comfort and aesthetic refinement. The chef’s kitchen is a culinary sanctuary, appointed with top-tier appliances, natural gas, and exquisite custom cabinetry. Seamlessly flowing into the family room and breakfast nook, the space is warmed by a gas fireplace and framed by a dramatic wall of glass that reveals captivating views of the redesigned heated pool. Outdoors, a private resort-style oasis unfolds—featuring a sumptuous Jacuzzi, cascading waterfalls, ambient lighting, and lush tropical landscaping designed for both relaxation and refined entertaining. For the avid boater, the deep-water dock—constructed with premium composite decking—includes a lift and moorings suitable for a 50+ foot yacht, offering effortless access to open water and embodying the very essence of luxury waterfront living. The thoughtfully designed floor plan provides exceptional versatility. The ground level hosts a private suite ideal as a fourth bedroom, executive office, or sophisticated den. Two beautifully appointed guest suites occupy the mid-level, while the crown jewel of the home awaits above: an extraordinary top-floor primary retreat. This serene sanctuary showcases sweeping Intracoastal views, a spa-inspired bath with a jetted soaking tub, dual vanities, and an expansive glass-enclosed shower—an indulgent escape designed for tranquility. Ascend further to a private loft and expansive rooftop terrace, where panoramic sunsets paint the sky in gold and crimson. Whether hosting elegant soirées or enjoying quiet evenings under the stars, this elevated outdoor sanctuary defines the art of coastal living. Every detail—from architectural lighting to impeccable finishes—reflects timeless sophistication. Delivered fully furnished and impeccably styled, this is more than a home; it is a rare investment-grade, turnkey waterfront estate offering immediate enjoyment, income potential, and uncompromising luxury.
Listing is courtesy of: BHHS FLORIDA PROPERTIES GROUP (727-461-1700)
Listing Agent: Michael Jones (727-458-4712)
514 WINDWARD PSGE, CLEARWATER BEACH, FL 33767
$1,799,000256 Days on yellowkey MLS ID: TB8428935
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3022 Built: 1965Community: Island Estates Of ClearwaterSingle Family
Taxes:
Tax Year:
Remarks: As you enter your new home through the Double entry doors you will be met by this completely remodeled 5 bedroom, 4 bath home, you have beautiful open water views from your living area and a wood burning fireplace. Spectacular Open floor plan, overlooking the pool and inviting backyard. This Island Estates home has a split bedroom floor plan and is over 3200 Sq Feet of living space space. Inside the home, the New Wood Plank Tile Flooring is throughout making all areas flow together. The kitchen has all new Stainless Steel Samsung appliances, large Island with plenty of counter space and additional storage and has an open view into the dining room, which has two Large built in Buffets with extra storage. This open floor plan allows spectacular views from the main living areas. Open the Sliders in the Living area and head out to the pool area, where there is plenty of space for outdoor living and dining. The Primary bedroom with EnSuite is an Oasis in your home with double vanity and shower area. There is an additional room off the bath that could be used as an office or Dressing area. The Walk in Closet is large and has built-ins. All of the secondary bedrooms have sliders/or French Doors that lead outside to either the yard or pool area, Your guests will enjoy their privacy as two of the bedrooms have an Ensuite and the other 2 share a Secondary Bath, with 1 bedroom having direct access. Relax or Entertain by the Pool and the back yard through one of the many sets of sliding glass doors and out to the spacious lanai, enjoy a sparkling pebbletec pool and covered dock with Boat Lift and rare open Canal views that stretch all the way to Caladesi Island. Roof was installed in 2016. Owner's are in process of reinforcing the dock stringers and new decking.
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