Location: Longboat Key
Keyword(s): Bayshore High
Keyword(s) High School: Bayshore High
Do Not Show Listings
761 NORTON ST, LONGBOAT KEY, FL 34228
$4,290,000176 Days on yellowkey MLS ID: A4677200
REDUCED by $100,000 (2.3%) on 05/30/2026
Bed: 4 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 4674 Built: 2004 Tax: $14,281 (2024)Community: Sleepy Lagoon Park 2Spa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,281
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2024
Middle School: Martha B. King Middle
Remarks: NOW OFFERED WITH A SIGNIFICANT PRICE IMPROVEMENT, 761 Norton Street presents an exceptional opportunity to own a luxury waterfront home in Longboat Key's highly desirable Sleepy Lagoon community. Positioned along a quiet canal with direct boating access to Sarasota Bay, the Intracoastal Waterway, and the Gulf, this canal-front residence combines the durability of reinforced concrete construction with the relaxed sophistication of Florida waterfront living. Featuring four bedrooms, four full en-suite baths, three half baths, and 4,674 square feet under air, the residence was thoughtfully designed to accommodate multi-generational living, extended family visits, seasonal guests, or those seeking exceptional flexibility for entertaining. Built with enduring quality in mind, the home features solid poured concrete construction reinforced with rebar throughout, hurricane-rated windows and doors, and a five-stop elevator providing convenient access to every level. A light-filled travertine foyer with an interior water feature creates a memorable arrival, while smart-home technology and newly installed remote-controlled blinds add modern convenience throughout. The main living level centers around an open-concept kitchen and gathering space designed for effortless indoor-outdoor living. Custom wood cabinetry, stainless steel KitchenAid appliances, a cooktop, beverage cooler, and generous entertaining areas flow seamlessly to the outdoor terrace. Beyond the walls of glass, a private resort-style environment awaits. The travertine pool deck features an infinity-edge pool and spa, outdoor shower, summer kitchen, and Coyote grill, creating an ideal setting for waterfront entertaining and year-round enjoyment. For boating enthusiasts, the property's canal-front setting is among its most compelling features. A 28,000-pound boat lift and dedicated lift for two personal watercraft provide convenient access to the region's renowned boating waters, allowing owners to cruise directly to waterfront restaurants, explore Sarasota Bay, spend the day fishing, or enjoy sunset excursions throughout Longboat Key and Sarasota's barrier islands. Inside, architectural details add warmth and character, including a two-tone tray ceiling, travertine fireplace, custom art niches, and generously sized guest suites with walk-in closets and private baths. One suite features a Jacuzzi tub, dual vanities, walk-in shower, and private water closet with bidet, while additional suites provide comfortable accommodations for family and guests. A rare and distinctive feature of the residence is its mirrored floor plan concept, creating two separate yet connected living experiences under one roof. An additional living level includes a second kitchen, bar area, living room, and matching guest accommodations, offering remarkable flexibility for private guest quarters, extended family living, or long-term visitors. Additional highlights include a 4-car tandem garage, abundant storage, and a premier location on Longboat Key. Residents enjoy convenient access to St. Armand's Circle, the St. Regis Longboat Key Resort, downtown Sarasota, Anna Maria Island, championship golf, world-class dining, boutique shopping, and the area's renowned Gulf beaches. Combining direct boating access, exceptional construction quality, resort-inspired outdoor living, and a coveted Longboat Key location, 761 Norton Street represents a rare opportunity to experience the very best of Florida waterfront living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
4960 GULF OF MEXICO DR #206, LONGBOAT KEY, FL 34228
$649,900176 Days on yellowkey MLS ID: A4679160
0 Days Off yellowkey (back on 5/30/2026)
REDUCED by $10,000 (1.5%) on 04/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1523 Built: 1975 Tax: $7,738 (2025)Community: Windward Bay AmdCondo
Taxes:$7,738
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Public showings are now available for the first time. After months of restricted access due to a tenant, this residence is finally available for public showings. Restricted access resulted in only a handful of private showings, giving today’s buyers a rare chance to discover a home that’s been under the radar. Unbeatable opportunity at $649,900 for a full Bayfront Waterview, corner end-unit on Longboat Key. Exceptionally priced below market value—this residence represents the lowest-priced Bayfront end unit in the highly desirable community of Windward Bay, in over 5 years. A compelling price point, providing rare access for those seeking to own a premium waterfront residence at an extraordinary price. Encompassing 1,523 square feet, this stylishly furnished, two-bedroom, two-bath residence is thoughtfully designed to showcase uninterrupted panoramic Bay views from every room. Natural light fills the open living and dining areas, where expansive windows frame ever-changing Bay views from sunrise through the evening’s sunset. The remodeled 2024 kitchen opens seamlessly to the main living area and features recently completed upper cabinetry and a sophisticated yet functional layout ideal for both relaxed daily living and entertaining. Recently acquired “chic” French doors in both bedrooms open to the Florida Room, a signature feature for Longboat Key residences, offering additional living space to enjoy morning light and serene Bay vistas. The spacious primary suite includes a private en-suite bath and a generous walk-in closet, providing comfort, supporting everyday living, and abundant storage. “Pet Friendly” Windward Bay is a well-established waterfront community known for its mature landscaping, waterfront setting, resort-style amenities, a strong proactive association with solid reserves, and an enduring reputation as one of Longboat Key’s most welcoming communities. (Attributes that continue to attract owners who value lifestyle as much as long-term stability.) The Milestone Inspection and Capital Reserve Study are complete. Windward Bay’s Monthly Condo Fees for 2025 were actually reduced and for 2026 only increased slightly by $13 a month, demonstrating a financially healthy Condo Association. Offered furnished and move-in ready, this corner end-unit provides flexibility as a full-time residence, seasonal retreat, or investment opportunity. From dolphins at dawn to sunsets on the Gulf—every day is paradise. Community Highlights: Enjoy three beach access points (including one private), 26 acres of lush tropical surroundings including ½ mile of nature trails, two heated pools for year-round enjoyment, fitness center and sauna, clubhouse for social gatherings, tennis and pickleball courts, boat docks (waitlist) and kayak launches for water enthusiasts, covered parking and storage. With convenient access to Downtown Sarasota, St. Armands Circle, Bridge Street, championship golf courses, renowned restaurants, shopping destinations, and vibrant cultural attractions, you'll never have a shortage of entertainment options. An uncommon offering distinguished by exceptional value, location, and the timeless appeal of gulf to bay living. Private showings are available for those seeking a rare chance to own a premium waterfront residence at an extraordinary price.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Debby Mccaig (941-544-1713)
615 DREAM ISLAND PL #210, LONGBOAT KEY, FL 34228
$949,90077 Days on yellowkey MLS ID: TB8503989
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1509 Built: 1985 Tax: $11,560 (2024)Community: Harbour Villa Club At The BuccaneerSpa: YesCondo
Taxes:$11,560
Remarks: Paradise at Harbour Villa Club – Waterfront Luxury with a boat slip on Longboat Key! Enjoy this condo year round, or rent it weekly when you cannot be there- you choose! Discover this fully renovated 2BR/2BA condo with panoramic views of the gorgeous Sarasota Bay. Bright and spacious, the open floor plan features soaring 9 ft ceilings, custom finishes, a gourmet kitchen with top-of-the-line appliances and a sleek wet bar. The primary suite offers stunning water views, dual closets, and a spa-inspired bath. The second bedroom is spacious and set apart from the primary. Step into the enclosed lanai for breathtaking 180° water views and added living space— perfect for relaxing or entertaining. This unit comes with a deeded 40' boat slip #3 which features upgraded power and plumbing, new wraps, caps, marine grade bumpers and a deck box- a rare bonus that can accommodate a 55' vessel! Harbour Villa Club is nestled in a quiet corner and you can walk or bike to the beach, area restaurants, and beloved Harry's Corner Store. This is a pet friendly community with covered parking, storage, elevators, kayak and bike storage, private dock, heated pool, tennis/pickleball courts, grills and beautiful landscaping. Weekly rentals allowed. Call today!
Listing is courtesy of: CENTURY 21 BILL NYE REALTY (813-782-5506)
Listing Agent: Lori Lahart (813-297-9610)
667 EL CENTRO, LONGBOAT KEY, FL 34228
$380,000311 Days on yellowkey MLS ID: A4664572
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1327 Built: 1969Monthly Fee: $1,340 Tax: $6,206 (2024)Community: Spanish Main Yacht Club CondoVilla
Taxes:$6,206
Remarks: New photos coming on this beautifully updated free-standing villa in Spanish Main Yacht Club on Longboat Key, a warm and vital boating community with private beach access, pool, clubhouse and boat slips. The community is undergoing a renaissance of sorts as many units (including this one) did have water intrusion in the summer storms of 2024. This owner contracted with the community contractor. has paid related assessment and work is nearly completed! This unit has a bright open floor plan and hurricane windows. Main living area has tile flooring and both bedrooms will have new carpet. There are two bonus areas, one is adjacent to the primary bedroom and could be a private reading area or office and the other adjoins the great room. Once completed, this unit will have two new baths, new appliances, kitchen updated, new doors and new paint throughout. This villa is on the corner and has a much-desired additional parking pad, giving as many as four parking spaces depending on car size. The laundry room, typical of Florida, is in a separate room under the carport. Longboat Key is paradise. A barrier island off Sarasota, where you can find wonderful restaurants, community tennis facilities, parks, bike lanes and a short drive to Sarasota and Anna Maria Island.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Holly Switow (941-735-3186)
718 SPANISH DR N, LONGBOAT KEY, FL 34228
$435,000112 Days on yellowkey MLS ID: A4687749
REDUCED by $14,500 (3.2%) on 05/14/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1327 Built: 1969 Tax: $2,539 (2025)Community: Spanish MainVilla
Taxes:$2,539
Remarks: Discover Longboat Key waterfront living at its very best at 718 Spanish Dr N, a beautifully updated freestanding villa in the sought-after Spanish Main Yacht Club. This home has been completely renovated to today’s highest standards following Hurricane Ian, delivering a fresh, high-end coastal finish throughout with meticulous craftsmanship and premium materials. Just steps from your door, enjoy private deeded beach access to the powder sands and turquoise color of the Gulf of Mexico — perfect for sunrise walks, beachcombing, or sunset gatherings. Boaters will appreciate the community’s deep-water marina with boat slips priced around $1,200 annually that have direct access to the Intracoastal Waterway, and quick passage to the open Gulf, along with kayak racks and fishing right at hand. Inside, the bright open-concept 2-bedroom, 2-bath villa showcases an elevated, contemporary coastal design. The gourmet kitchen is a true entertainer’s dream, featuring sleek modern cabinetry, elegant stone countertops, a spacious island, and high-end stainless steel appliances. Sunlight pours through the generous windows and sliders, highlighting the beautiful new flooring that flows seamlessly into the living and dining areas. A sun-drenched Florida room/lanai offers flexible space, ideal for a home office, artist studio, or casual living — all overlooking lush tropical landscaping and a peaceful community setting. Both bedrooms are generously sized with ample closet space, while the updated baths feature contemporary fixtures and finishes for a spa-like feel. Additional highlights include a private outdoor shower, a spacious carport for your island toys, and thoughtful storage throughout. This vibrant, friendly 55+ community (can be under 55 to purchase) offers a heated pool, a clubhouse with marina views, shuffleboard courts, and a welcoming social atmosphere. Maintenance-free living, beautifully landscaped grounds, and covered parking complete the carefree Longboat Key lifestyle. Whether you seek a full-time waterfront residence, seasonal escape, or outstanding investment, 718 Spanish Dr N offers turnkey luxury with effortless deeded beach access and marina convenience in one of Longboat Key’s most desirable waterfront enclaves. Minutes to St. Armand's Circle, downtown Sarasota, and Anna Maria Island, yet tucked away in paradise. Don’t miss this rare opportunity to own a freshly renovated gem in Spanish Main Yacht Club — where high-end coastal living meets the best of island boating and beach life!
Listing is courtesy of: SARASOTA REAL ESTATE GROUP (941-922-8400)
Listing Agent: John Woodward (941-922-8400)
5920 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$1,749,500429 Days on yellowkey MLS ID: A4652254
Bed: 2 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2823 Built: 1973 Tax: $8,478 (2024)Community: Longboat KeySpa: YesSingle Family
Taxes:$8,478
Remarks: DEEDED BEACH ACCESS AND DEEP WATER CANAL at this beautifully renovated mid-key beach house on the barrier island of Longboat Key. You can enjoy a 3-minute walk to the beach using your private beach access or step outside and enjoy the canal on your trex dock. The uncrowded beach with natural surroundings, fine sand beaches, warm breezes, and clear turquoise waters is truly a special place. Entering the home, you are greeted by terrazzo floors, stunning 2 story foyer and a water view of the canal. All new wood kitchen cabinets including island and coffee bar with quartz countertops making this a great area to entertain guests. All 3 bathrooms have been completely renovated and include custom tile showers. Large master bedroom with en-suite bathroom. An enclosed lanai overlooking the canal is a perfect spot for an office or tropical retreat. Large living room with wood burning fireplace and new tile flooring provides a relaxing space. New kitchen and bath fixtures throughout. Ceiling fans in each room. Being in the middle of LBK provides easy access to Anna Maria Island and Bradenton to the north, St. Armands and Sarasota to the south. SRQ airport is less than 45 minutes. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway, deeded beach and canal access with 5924 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together (or use one as a rental for an ongoing revenue stream}. The property is being sold as-is. Please use AS IS Residential Contract for Sale and Purchase_FloridaRealtors-FloridaBar-ASIS-7.xdp
Listing is courtesy of: JOHN DONATO REAL ESTATE INC (941-504-4987)
Listing Agent: John Donato (941-504-4987)
5924 GULF OF MEXICO DR, LONGBOAT KEY, FL 34228
$849,500429 Days on yellowkey MLS ID: A4651805
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1359 Built: 1955 Tax: $11,764 (2024)Community: Fractional SubSingle Family
Taxes:$11,764
Remarks: Sought after mid-key cottage home with DEEDED BEACH ACCESS on the barrier island of Longboat Key. Entering the home, you are greeted by terrazzo floors, wood beam ceilings and a tile accented gas fireplace in the large living room. An additional room overlooking screened in pool can be used as an office, exercise room or extra space for guests. Newly renovated kitchen with wood cabinets, quartz countertops, new sink and fixtures. Bathrooms have been completely renovated with beautiful walk-in tiled showers. A built-in bookcase in the living room adds charm with plantation shutters, accent lighting and ceiling fans throughout. Completely restored home by licensed general contractor and professionally mitigated after hurricane Helene flood damage. The house shares a driveway and deeded beach access with 5920 Gulf of Mexico Drive making it a perfect guest house or family compound when purchased together. Another possibility is to use one as as a rental for an ongoing revenue stream. The property is being sold As-Is (use FAR-BAR-ASIS-7.
7147 LA LENAIRE DR, LONGBOAT KEY, FL 34228
$5,000,000241 Days on yellowkey MLS ID: TB8448347
REDUCED by $235,000 (4.5%) on 05/07/2026
Bed: 5 Bath: 5.5 Liv Area Sq Ft: 3503 Built: 1990Monthly Fee: $283 Tax: $33,963 (2023)Community: Jewfish KeySpa: YesSingle Family
Taxes:$33,963
Tax Year: 2023
Middle School: W.D. Sugg Middle
Remarks: A rare offering on Florida’s coveted west coast, this private island sanctuary feels worlds away yet remains moments from the region’s most beloved coastal destinations. Set on the exclusive 38-acre island of Jewfish Key (accessible only by boat), this remarkable 1.35-acre estate commands its own secluded shoreline and uninterrupted views of crystal clear waters. Inspired by Polynesian architecture and designed to dissolve the boundaries between indoors and out, this estate home unfolds through airy pavilions connected by elevated walkways. Towering palms and lush tropical landscaping envelop the home, while its 18-foot elevation ensures both peace of mind and panoramic, horizon-level vistas. Inside, the freshly reimagined kitchen serves as the gathering heart of the home, with sleek quartz countertops, modern cabinetry, and a spacious oversized island that effortlessly bridges culinary function and relaxed entertaining. Expansive sliding glass doors draw natural light into the living space and frame sweeping views of the sandbar and bay, perfect for sunset watching. The main residence includes four bedrooms and four-and-a-half baths, plus a separate guest suite offering an additional bedroom, kitchen, and full bath, ideal for hosting with comfort and privacy. The primary suite is where the pace of the island truly settles in. Wake up to wide-open bay views, linger with coffee in the sitting area, or enjoy a glass of wine as the sun sinks toward the horizon. The ensuite feels fresh and spa-like, with a soaking tub, walk-in shower, and water views. A series of screened porches and wraparound decks encourage slow living, morning yoga on the deck, afternoon reading in the shade, sunset grilling and cocktails overlooking the Gulf. Outdoors, a newly installed pool and spa with a sun shelf and expansive sundeck overlook the storied Jewfish Key Sandbar. A private dock with jet ski lift offers instant access to calm waters perfect for fishing, snorkeling, paddle boarding, or exploring neighboring Longboat Key and Anna Maria Island, both just minutes away by boat and beloved for dining, boutique shopping, and laid-back coastal culture. Equal parts island hideaway and refined coastal home, this one-of-a-kind property offers the rare combination of true privacy, effortless access, and natural beauty, set against a backdrop of turquoise water, powder soft sand, and endless sky. Here, relaxation, adventure, and natural beauty converge in a setting that feels almost like an escape, yet unmistakably home.
Listing is courtesy of: SIGHT REAL ESTATE, LLC (877-361-0878)
Listing Agent: Chase Moore (727-325-7272)
578 - 580 COMPANION WAY, LONGBOAT KEY, FL 34228
$900,000156 Days on yellowkey MLS ID: A4682264
REDUCED by $99,000 (9.9%) on 05/07/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoApartment
Taxes:$11,672
Remarks: Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value.. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
Listing is courtesy of: NEXTHOME EXCELLENCE (941-893-4505)
Listing Agent: Linh Pham (941-900-6789)
578 COMPANION WAY, LONGBOAT KEY, FL 34228
$900,000156 Days on yellowkey MLS ID: A4682186
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 1792 Built: 1963 Tax: $11,672 (2025)Community: Longboat KeySpa: NoSingle Family
Remarks: Massive Price Reduction - Rare Opportunity to Own Your Slice of Beach Paradise! Live the ultimate coastal lifestyle with sun, sand, and breathtaking surroundings at an exceptional value. Stunning curb appeal duplex located in the highly desirable Longboat Key featuring two separate addresses, 578 Companion Way and 580 Companion Way. This bright and welcoming coastal retreat offers an elegant and comfortable living environment where refreshing sea air and natural sunlight fill the interior through expansive windows. The property features two separate units including one 2 bedroom 2 bathroom unit and one 2 bedroom 1 bathroom unit. Offered fully furnished and showcasing high quality updates throughout, the property includes a new roof, new AC systems, new water heaters, and all new appliances completed in 2025, delivering modern luxury and peace of mind. Residents may enjoy access to Cedars East resort style amenities including pool, fitness center, and tennis courts with a small optional membership fee. Ideally positioned just steps from the pristine, wide, and uncrowded Gulf beaches, this property provides the ultimate Longboat Key lifestyle. Conveniently located near world class dining and shopping at St Armands Circle, vibrant downtown Sarasota, championship golf courses, marinas, cultural attractions, and everything Sarasota has to offer. Vacation rentals are permitted, creating an outstanding opportunity for investors, seasonal residents, or families seeking to live in one unit while generating additional rental income from the second unit.
4380 EXETER DR #H202, LONGBOAT KEY, FL 34228
$499,000249 Days on yellowkey MLS ID: A4671530
REDUCED by $21,000 (4.0%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1970 Tax: $6,314 (2025)Community: Longboat HarbourSpa: NoCondo
Taxes:$6,314
Remarks: Experience the ultimate Bay-to-Beach lifestyle in this turnkey 2-bedroom, 2-bath condo at Longboat Harbour, where nearly every room offers sparkling water views and a sense of calm that only waterfront living can bring. Perfect for investors or seasonal residents, this home combines desirable updates with a lifestyle that’s hard to beat. Fully updated in 2025, this home blends modern luxury with coastal charm. LVP flooring, textured ceilings, and fresh paint flow throughout, while the brand-new kitchen boasts with all-white cabinetry, coffee bar, coastal glass backsplash, and quartz countertops. The master suite features custom closet doors, a new porcelain shower with frameless glass, porcelain flooring, and a quartz-top vanity with Bosch washer/dryer in the bath. The hall bath includes a new porcelain shower/tub combo, stylish vanity with quartz countertops, and contemporary Euroflush toilets. Every detail is designed to make the interior as inviting as the stunning views outside. Every update you could hope for in a ready-to-enjoy condo! Step outside and enjoy the resort-style amenities of a vibrant waterfront community. Longboat Harbour offers four heated pools, tennis and pickleball courts, a recreation hall, billiards, game rooms, docks with sailboat access (no bridges to the bay), and a fitness center. Social committee events, on-site grills, and beautiful landscaping surround you at every turn. For beach lovers, the private deeded beach access at 4415 Gulf of Mexico includes a beach house with restrooms, showers, and reserved parking. A short drive from Longboat Key, St. Armands Circle, and downtown Sarasota, you’ll find boutique shops, delightful dining, arts, festivals, and the wonder of Selby Botanical Gardens. Watch Gulf sunsets paint the sky while manatees, ospreys, and egrets play in the waters below… this condo is all about a life of fun, relaxation, and unforgettable moments.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Ryan Skrzypkowski (941-328-8307)
948 SPANISH DR S, LONGBOAT KEY, FL 34228
$1,199,000128 Days on yellowkey MLS ID: A4685572
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1399 Built: 1968 Tax: $4,945 (2025)Community: Spanish Main Yacht Club CondoVilla
Taxes:$4,945
Remarks: Stunning full bay views as you enter this jaw-dropping magnificent, completely custom renovated stand-alone villa on Sarasota Bay. Professionally designed starting with an 18-by-11-foot gourmet kitchen. With 10-12-foot wood beam ceilings, a beautiful 12-foot quartz island that seats 10-plus people, solid wood cabinetry, Café’ brand double oven, refrigerator with two additional drawers, stainless steel appliance, huge undermount sink, glass backsplash, separate wet bar and more. The 2-by4-foot white porcelain rectangular tile flows seamlessly from room to room with water views that entertain you every moment of every day. With the Intracoastal Waterway just beyond the brick paver back patio, the wildlife is abundant, more than you can imagine, with morning sunrises that softly greet you as you awaken to a true slice of paradise. The entire glass-enclosed 23-by-12-foot lanai brings so much light, brightness and cheerfulness that it makes your heart smile. The end unit offers privacy and protection with lush green mangroves creating a protected area plus easy access for entering the water, going for a swim, fishing or kayaking. Back to the renovations, the main bedroom en suite offers privacy with upscale bath appointments, a double sink, and large designer shower. The enclosed laundry area right off the bedroom was carefully crafted with a walk-in closet, extra storage room and a rare whole-house water purification system. Not to mention all hurricane windows and doors throughout with additional footings, foam support and steel beams under the sliding doors to ensure structural integrity and peace of mind. All appliances are 2025, LG Thin Q washer and dryer, Café kitchen appliances, tankless hot water tank, custom fan and lights, all new plumbing and electrical as the home was taken down to the studs. PVC sewer lines completely replaced all cast iron pipes. New tile roof in 2025. There is nothing to do except move in and relax. You will not be disappointed. All FEMA regulations have been completed, including inspections. Vibrant waterfront 55-plus community with 40-slip marina and deeded beach access to gorgeous beaches of Longboat Key. Close to restaurants, shops, renowned St. Armands Circle, plus 30 minutes to Sarasota International Airport. Take a look.
Listing Agent: Kimberly Freiwald (941-256-6775)
592 JUAN ANASCO DR, LONGBOAT KEY, FL 34228
$4,000,00080 Days on yellowkey MLS ID: A4691388
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3600 Built: 2027 Tax: $6,949 (2025)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$6,949
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, a premier luxury builder known for crafting high-end coastal residences with exceptional attention to detail and durability, this stunning new construction home at 592 Juan Anasco Dr offers an unparalleled blend of sophistication, comfort, and waterfront living. Perfectly positioned on a canal-front lot in Longboat Key, this 5-bedroom, 5.5-bath residence is thoughtfully designed to capture the essence of refined coastal living. Expansive windows, soaring ceilings, and a light-filled interior create an inviting atmosphere, while the home’s modern coastal aesthetic is complemented by carefully curated finishes and timeless design elements that elevate every space. The spacious and well-appointed floor plan offers a seamless balance of functionality and privacy, making it ideal for both everyday living and elevated entertaining. Generous living areas provide a welcoming environment for gathering, while the primary suite serves as a true retreat—offering a peaceful escape with a spa-like feel. Each additional bedroom is designed with comfort in mind, providing flexibility for guests, family, or extended stays. Step outside to your private waterfront oasis, where a resort-style setting invites relaxation and effortless entertaining. Whether hosting friends, enjoying quiet evenings by the water, or taking advantage of Florida’s year-round sunshine, this outdoor space is designed to be experienced. With direct canal access, boating enthusiasts will appreciate the ability to enjoy the Intracoastal lifestyle right from their backyard. Built to meet current FEMA guidelines and elevation requirements, this home offers enhanced protection, improved insurance efficiency, and long-term peace of mind—an essential advantage for waterfront properties. The elevated construction is thoughtfully designed to perform in coastal conditions while maintaining both functionality and architectural appeal. Living on Longboat Key means embracing a lifestyle that is both refined and relaxed. Known for its pristine Gulf beaches, world-class golf, and exclusive residential feel, the island offers a quieter, more private alternative to neighboring destinations. Residents enjoy convenient access to the renowned shops and restaurants of St. Armands Circle, the cultural attractions of downtown Sarasota, and nearby marinas, beach clubs, and nature preserves. From morning walks along the shoreline to sunset cruises and evenings of coastal dining, every day feels like a getaway. This is more than a home—it’s a lifestyle defined by waterfront elegance, modern construction standards, and one of Florida’s most sought-after coastal communities. Pricing, availability, and final details subject to adjustment prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
5055 GULF OF MEXICO DR #412, LONGBOAT KEY, FL 34228
$565,000141 Days on yellowkey MLS ID: A4683419
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1484 Built: 1973 Tax: $8,183 (2024)Community: Club Longboat Beach & TennisSpa: YesCondo
Taxes:$8,183
Remarks: Discover an exceptional value opportunity in Club Longboat on Longboat Key, one of the island’s most desirable beachside communities known for its active lifestyle and resort style amenities. This three bedroom, two bathroom ground floor walkout residence is currently the least expensive unit in the community and presents a rare chance to create a fully customized coastal retreat. With a solid existing layout and desirable ground level access that enhances indoor / outdoor living, the residence offers tremendous flexibility. Buyers have the opportunity to redesign and expand the third bedroom to add additional square footage, whether to create a more spacious primary suite, an inviting guest retreat, or a dedicated office or flex space. The potential to transform this residence into a personalized showpiece is exceptional. Club Longboat is ideal for tennis, pickleball, and beach enthusiasts, offering eight Har Tru tennis courts with three lined for pickleball, two heated swimming pools, and 750 feet of private Gulf front beachfront complete with lounge chairs and umbrellas. The serene waterfront setting enhances the peaceful atmosphere and scenic surroundings. The residence includes a covered parking space directly in front of the unit along with abundant guest parking. On site management serves the 85 residences, providing convenience and peace of mind within a welcoming, all ages community. Owners enjoy a pet friendly environment with no weight restrictions and a flexible rental policy allowing one month minimum rentals up to twelve times per year, creating excellent income potential. Conveniently located near shopping and fine dining, this is a rare opportunity to secure a value driven property in an amenity rich Longboat Key beachfront community and make it entirely your own.
Listing Agent: Ryan Ackerman, Pa (305-205-7700)
597 SUTTON PL, LONGBOAT KEY, FL 34228
$530,000256 Days on yellowkey MLS ID: A4669989
Bed: 2 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 1008 Built: 1972 Tax: $2,379 (2025)Community: Sutton PlaceSpa: NoHalf Duplex
Taxes:$2,379
Remarks: Experience the best of Longboat Key living at Sutton Place, ideally positioned mid-island with convenient access to both Sarasota Bay and the Gulf of Mexico. Enjoy deeded beach access just moments away—perfect for daily beach outings, sunset walks, and the pristine Gulf shoreline. Active living comes naturally here. Bike to Bayfront Park for pickleball or tennis, or visit the nearby dog parks where neighbors and pets gather. When it’s time to relax, choose from two community pools, including one overlooking the marina and peaceful Bay waters. The community also offers multiple BBQ areas, creating ideal spaces for gatherings with friends and family in a beautifully maintained coastal setting. This two-story townhome offers 2 bedrooms and a full bathroom upstairs, with a second bathroom conveniently located on the main level. The eat-in kitchen features a charming dining nook, and the adjoining screened porch provides a tranquil outdoor retreat. A private one-car garage adds convenience and storage for a vehicle, golf cart, or beach essentials. Additional highlights include first-come, first-served dock slips available for a nominal fee and a setting that offers comfort and peace of mind. Seller reports the property had no flooding during Hurricane Helene. Live the Longboat Key lifestyle—sun, sand, coastal breezes, and effortless island living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Simone Schaerf (941-260-1550)
720 TARAWITT DR, LONGBOAT KEY, FL 34228
$2,900,000139 Days on yellowkey MLS ID: A4684316
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2160 Built: 2027 Tax: $8,534 (2025)Community: Longboat KeySingle Family
Taxes:$8,534
Remarks: Pre-Construction. To be built. Build your dream waterfront home on North Longboat Key! Discover an exceptional opportunity to create your custom coastal retreat on this build-to-suit lot with 120 feet of waterfront frontage. The property is primed for development, with a permit filed and anticipated approval. Included in the price are complete architectural plans by Sweet Sparkman Architecture and Interiors, renowned for their innovative designs that harmonize modern luxury with beauty of Florida's coastal landscapes. The thoughtfully designed floor plan ensures a seamless flow for everyday living and entertaining, capturing breathtaking water views from key living areas. Whether you’re relaxing indoors or going out to enjoy the vibrant outdoor spaces, this home has been envisioned to maximize its unparalleled waterfront location. Key features include a new seawall in 2023 that provides a solid foundation for waterfront living. Deeded beach access, just a short distance away, offers private enjoyment of pristine sandy shores on Longboat Key. Boating enthusiasts will appreciate the ample frontage for a dock and boat, providing easy access to Sarasota Bay and beyond. On sought-after North Longboat Key, the property offers proximity to acclaimed restaurants like Shore, Whitney’s and Mar Vista, ensuring dining and entertainment are always nearby. This is your chance to bring a remarkable vision to life in one of Florida’s desired locations. Schedule your private showing today and imagine the possibilities.
Listing Agent: Moriah Taliaferro (941-504-9910)
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