Location: Longboat Key, 34228
Do Not Show Listings
713 SAINT JUDES DR S #1, LONGBOAT KEY, FL 34228
$569,000186 Days on yellowkey MLS ID: TB8459956
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1215 Built: 1966Monthly Fee: $1,043 Tax: $1,454 (2024)Community: Saint Judes AptsCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$1,454
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Wake up to tranquil canal views, step outside to the water, and embrace the effortless island lifestyle that makes Longboat Key one of Florida's most sought-after coastal destinations. This beautifully updated 2-bedroom, 2-bath waterfront condo offers 1,215 square feet of thoughtfully designed living space, along with a carport and two dedicated parking spaces—a rare convenience for island living. Perfectly positioned on a peaceful canal with direct access to the Intracoastal Waterway, this property is ideal for boating enthusiasts, investors, or anyone seeking a true waterfront retreat. A brand-new private dock provides the perfect place to keep your boat, enjoy morning coffee by the water, or spend evenings watching the sunset over the canal. Inside, the residence has been completely transformed into a clean, coastal-inspired retreat with high-end updates throughout. The fully permitted renovation was completed with an emphasis on quality craftsmanship, long-term value, and peace of mind. The stunning new kitchen features updated cabinetry, countertops, and appliances, while both bathrooms have been thoughtfully redesigned with elegant, modern finishes that create a spa-like atmosphere. Beautifully updated vanities, new fixtures, designer tilework, and carefully selected finishes elevate the spaces, providing a luxurious and relaxing experience. Additional improvements include a new A/C system, complete plumbing repipe with new water and sanitary lines, new water heater, upgraded electrical panel, and all new impact windows and exterior doors. The building also benefits from a durable metal roof installed in 2016, offering insurance advantages and low-maintenance ownership. Beyond the exceptional lifestyle, the property also presents outstanding income potential, generating approximately $5,000+ per month during season and $3,500+ per month in the off-season, making it an ideal blend of personal enjoyment and investment performance. Located just minutes from pristine Gulf beaches, local dining, shopping, and everyday conveniences, the property is also near Joan M. Durante Community Park, known for its scenic walking trails, native gardens, and breathtaking bayfront sunset views. Rare Opportunity: The adjacent unit is also available, presenting the unique chance to own the entire building as a waterfront duplex—ideal for a private family compound, multi-generational living, or maximizing rental income potential. Whether you're seeking a primary residence, seasonal escape, or income-producing investment, this property offers a rare combination of location, condition, boating access, and exceptional waterfront living. Schedule your private showing today and experience the very best of Longboat Key living.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Connor Meckley (941-279-0013)
677 LANDS END DR, LONGBOAT KEY, FL 34228
$2,695,000141 Days on yellowkey MLS ID: A4682565
REDUCED by $95,000 (3.4%) on 06/12/2026
Bed: 3 Bath: 3.0 Gar: 4 Liv Area Sq Ft: 4182 Built: 1989Monthly Fee: $967 Tax: $33,361 (2025)Community: Lands EndSpa: NoSingle Family
Taxes:$33,361
Elementary School: Anna Maria Elementary
High School: Bayshore High
Tax Year: 2025
Middle School: W.D. Sugg Middle
Remarks: Experience the timeless appeal of a quintessential Florida island home, immersed in a lush tropical waterfront setting on Longboat Key. Elevated above a serene natural bayou off Sarasota Bay, this distinctive residence embodies the relaxed elegance of island living, with soaring ceilings, expansive wraparound decks, and pristine Gulf beaches just moments away. Launch a kayak from your private dock, enjoy exceptional fishing and bird-watching from your backyard, or keep your boat in one of the community's deepwater slips on the open bay. The association offers slips up to 43 feet in length, and either your private dock on the bayou or a bayfront slip may accommodate an optional boat lift. The spacious elevated residence is anchored by a dramatic great room featuring vaulted cedar ceilings and exposed beams. An expansive sunroom with a bar area and handcrafted display shelving, a dedicated library, an inviting family room, and a private office with extensive built-in cabinetry contribute to the home's distinctive character. The entire main living area is thoughtfully arranged on a single level. Extensive decking welcomes you at the front entry and wraps around a lush central atrium courtyard, creating exceptional spaces for outdoor dining, entertaining, and relaxation. A shaded cabana-inspired retreat offers comfort throughout the day, while the setting is equally suited for the addition of an elevated outdoor spa. The kitchen, centered around a generous island, is perfectly positioned for gathering with family and friends. The primary suite features a wall of windows overlooking the tranquil bayou, dual walk-in closets, and an additional wall of custom closet storage. A desirable split floor plan creates a private guest wing with two additional bedrooms and baths. Each guest room enjoys direct access to the surrounding decks and views of the tropical atrium. Two garages accommodate up to four vehicles and provide ample space for boats, golf carts, paddleboards, and additional storage. Most furnishings are included. Within Land's End, an intimate gated enclave of just 12 residences, owners enjoy maintenance-free landscaping, a heated swimming pool, tennis and pickleball courts, and beautifully landscaped grounds nestled among mature trees for exceptional privacy and convenient bay access. From here, a short walk or golf cart ride leads to the Gulf beach and popular island dining destinations, including Shore Longboat Key, Mar Vista Dockside Restaurant, and Whitney's. Nearby waterfront cafés, boutique shopping, fitness facilities, and a Pilates studio further enhance the island lifestyle. Enjoy breathtaking Gulf sunsets and tranquil bay sunrises from this exceptional waterfront community. Rarely does a property so perfectly capture the spirit of Old Florida, where tropical beauty, boating, nature, and beachside living come together in one of Longboat Key's most treasured island enclaves.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-383-2500)
Listing Agent: Cindy Fischer (941-465-1124)
701 MARBURY LANE, LONGBOAT KEY, FL 34228
$1,350,000370 Days on yellowkey MLS ID: A4657604
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2246 Built: 1993Monthly Fee: $2 Tax: $8,587 (2024)Community: Sleepy Lagoon Part No 2Single Family
Taxes:$8,587
Middle School: Martha B. King Middle
Remarks: Welcome to Bougain Villa, your Tropical Island Oasis on a deep water canal leading to secluded sandbars, the turquoise waters of the Gulf of Mexico, and several nearby waterfront restaurants. From the moment you arrive at this magical property, Zen Vibes will calm the mind and put it's whimsical spell on you. Lush plantings, perfectly positioned sitting areas, a private cocktail pool and a custom dock flanked by native mangroves surround this elevated Charmer. Perfectly updated and decorated for maximum pleasure, the vaulted ceilings, clerestory windows providing lots of natural light, and huge back deck enhance the inviting living space and make this home perfect for entertaining indoors & outdoors. Cherry wood cabinetry, a cozy breakfast bar, granite tops, gas range and stainless steel appliances enhance the private kitchen which overlooks the comfortable family room. The primary suite with it's vaulted ceilings and wood floors is totally tucked away, and it's spa-like bathroom with dual sink, separate shower and jetted tub is a perfect retreat highlighted by natural stone and Travertine finishes. The guest bedrooms offer sunrise views, vaulted ceilings and cozy wood flooring and share a Moroccan inspired bathroom. The pecky cypress ceilings, indirect lighting throughout the living space and the colorful interior design and decor are truly special and the enclosed workshop, garage space and gardening sheds below provide additional room for fun. Easy access to miles of Longboat Key's pristine sugar sand beaches where neighbors gather to enjoy spectacular sunsets or just to enjoy a relaxing beach day. The convenience of nearby casual & fine dining, shopping and a short drive to Anna Maria Island's popular night life spots, as well as the Longboat Key Club with resort style amenities, make this the perfect island location for anyone dreaming of living the coveted Florida lifestyle. So come and discover your coastal adventures today on Florida's most prestigious barrier island.
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Tina Rudek Stark, Pa (941-920-0303)
1561 GULF OF MEXICO DR #403, LONGBOAT KEY, FL 34228
$13,000,000603 Days on yellowkey MLS ID: A4627926
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4187 Built: 2024 Tax: $81,320 (2025)Community: St. Regis Longboat KeyCondo
Taxes:$81,320
Remarks: Experience unparalleled luxury with breathtaking views of the Gulf of Mexico in the Armand Building. This exceptional residence features an open-concept floorplan designed for entertaining, complete with floor-to-ceiling glass doors that lead to an expansive terrace outfitted with a built-in gas grill, perfect for seamless indoor-outdoor living. Ideal for multi-generational gatherings, the clubroom serves as a fantastic bonus space, featuring a wet bar equipped with an ice maker, bar sink, and wine fridge. The gourmet kitchen is a chef’s dream, showcasing top-of-the-line Wolf and Sub-Zero appliances, including a 6-burner gas cooktop, double ovens, and an integrated cabinet front side-by-side refrigerator/freezer. A semi-private elevator with keyless entry transports you directly from your private two-car garage to your residence. The owner’s suite offers a spacious walk-in closet, a luxurious soaking tub, a frameless walk-in shower, and dual vanities with separate water closets. Designed with technology-ready infrastructure, this home allows for easy customization of your automation preferences. Located within the first branded residential community and ultra-luxe 5-star resort hotel on the Gulf, The Residences at The St. Regis Longboat Key blend legendary service with the allure of a serene seaside retreat. Spanning over 17 acres with 800 feet of direct beachfront, residents can indulge in unparalleled amenities, including signature St. Regis Butler and Concierge services, a world-renowned spa, in-residence dining, a resident-only pool and spa, a private clubhouse, a fitness center, and beachside cabanas. Discover a life of luxury and leisure at The Residences at The St. Regis Longboat Key—where every day feels like a getaway. The owner will consider a lease purchase with acceptable terms on this residence.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-383-7591)
Listing Agent: Michael Moulton (941-928-3559)
595 BOWSPRIT LN, LONGBOAT KEY, FL 34228
$3,099,000263 Days on yellowkey MLS ID: A4668868
REDUCED by $41,000 (1.3%) on 07/05/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2550 Built: 1966Monthly Fee: $21 Tax: $26,814 (2025)Community: Country Club ShoresSingle Family
Taxes:$26,814
Elementary School: Southside Elementary
High School: Booker High
Middle School: Booker Middle
Remarks: Longboat Key Waterfront Luxury. Experience the ultimate in waterfront living in this 4-bedroom, 2.5-bath Country Club Shores residence, tucked just off Sarasota Bay on a nice canal with quick access to the Gulf, sandbars, and every boating adventure Sarasota has to offer. A private dock, two boat lifts (20,000 lb and 7,000 lb), new seawall, and a custom fish cleaning station create a true boater’s paradise, while canal and bay views enhance the coastal setting. After a day of boating, sandbar hopping, fishing, or cruising the bay, come home to your heated pool, travertine-decked outdoor retreat. Retractable glass sliders, and pool bar blur the line between indoors and out, making this the perfect place to gather, unwind, and relive the day’s best moments on the water. Thoughtfully remodeled twice in recent years, the home blends refined coastal style with exceptional updates including a 2016 effective build year, roof, plumbing, electrical, PGT hurricane-impact windows and sliders, and two new A/C systems in 2024. The chef’s kitchen is a standout, featuring custom Devittori cabinetry, leathered granite, a dramatic 11’x5’ island, and premium Sub-Zero and Wolf appliances. Deeded private beach access, nearby Longboat Key Club amenities, and close proximity to St. Armands Circle and Downtown Sarasota complete this exceptional island offering.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Melissa Gissinger (941-404-2722)
7094 LONGBOAT DR E, LONGBOAT KEY, FL 34228
$6,995,0009 Days on yellowkey MLS ID: A4697907
Bed: 6 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 4776 Built: 1979 Tax: $22,736 (2025)Community: Longbeach On Longboat KeySpa: YesSingle Family
Taxes:$22,736
Remarks: Pre-Construction. To be built. An extraordinary opportunity to create a world-class waterfront estate on Sarasota Bay, this stunning new construction residence offers the ultimate blend of luxury, craftsmanship, and coastal living in one of Sarasota’s most coveted locations. Situated on an expansive 11,000+ square foot bayfront homesite, this magnificent two-story design features six spacious bedrooms, six and a half impeccably appointed baths, and a three-car garage, thoughtfully curated to embrace both elegant entertaining and relaxed waterfront living. With permits already in place and construction ready to begin, buyers have the rare advantage of securing a brand-new custom home while potentially taking delivery turnkey furnished for a truly effortless transition to paradise. Designed to maximize breathtaking water views and the coveted Sarasota lifestyle, the residence will showcase superior architectural details, expansive living spaces, and seamless indoor-outdoor connections that celebrate the beauty of its spectacular setting. The resort-inspired outdoor oasis will feature a sparkling pool and spa, a fully equipped outdoor kitchen, and generous entertaining areas perfectly suited for hosting family and friends against the backdrop of stunning bay vistas and unforgettable sunsets. Boating enthusiasts will appreciate the exceptional location, offering immediate access to Sarasota Bay and the Gulf of Mexico, making this an ideal retreat for those who embrace life on the water. Beyond the privacy and prestige of this remarkable homesite, residents will enjoy the convenience of walking to the beloved restaurants, boutiques, and vibrant atmosphere of Sarasota’s charming north end, while the sugar-sand beaches and turquoise waters are just moments away. Every detail of this exceptional offering has been thoughtfully envisioned to deliver a lifestyle defined by luxury, comfort, and coastal elegance, creating a rare opportunity to own a brand-new waterfront masterpiece in one of Florida’s most desirable destinations. Whether envisioned as a year-round residence or an extraordinary seasonal retreat, this soon-to-be-completed estate represents the pinnacle of Sarasota bayfront living, where impeccable design, modern conveniences, and an unrivaled location come together to create a legacy property for generations to come. Construction has not started yet however plans are available! Call now for more details!
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
530 DE NARVAEZ DR, LONGBOAT KEY, FL 34228
$4,295,000259 Days on yellowkey MLS ID: A4669195
REDUCED by $200,000 (4.4%) on 06/16/2026
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2025 Tax: $12,064 (2024)Community: Sleepy Lagoon ParkSpa: YesSingle Family
Taxes:$12,064
Remarks: New Construction - Discover the epitome of waterfront luxury with this newly built home in the heart of Longboat Key—competitively priced and move-in ready. Nestled along a private canal, this 4-bedroom plus den, 4,106 sq ft residence blends contemporary sophistication with coastal appeal. Designed for effortless indoor-outdoor living, the home boasts two spacious lanais, a private pool and spa, and an elevated foundation at 9.5 feet for added peace of mind. Boaters will enjoy concrete canal bulkhead with quick access to the Gulf of Mexico, perfect for endless days on the water. Inside, the home features engineered hardwood flooring, sleek quartz countertops throughout, a large walk-in pantry, and the convenience of dual laundry rooms. Set in a tranquil, private location just minutes from Longboat Key’s renowned beaches, golf courses, and upscale dining, this home is a rare gem. Don’t miss your opportunity to own a waterfront retreat in one of Florida’s most sought-after coastal communities.
Listing Agent: Joshua Freed (941-577-5121)
552 JUAN ANASCO DRIVE, LONGBOAT KEY, FL 34228
$975,000152 Days on yellowkey MLS ID: A4680786
0 Days Off yellowkey (back on 7/3/2026)
REDUCED by $24,999 (2.5%) on 06/03/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1846 Built: 1960 Tax: $17,419 (2024)Community: Sleepy Lagoon ParkSingle Family
Taxes:$17,419
Remarks: Under contract-accepting backup offers. Imagine living the coastal lifestyle only dreams are made of! Wake each morning to the sunrise over your local beach—just a short stroll down the street—where you can sink your toes into sugary white sand, take an early walk, or collect seashells along the shore. Return home to enjoy coffee outdoors by your heated pool, relaxing on the deck as tranquil water views set the tone for the day. Take a refreshing dip, then unwind as nature’s canvas unfolds before you, with shifting light and brilliant shades of blue and azure. In the evening, hop on your boat from your backyard and cruise effortlessly to waterfront restaurants and sunset destinations. With a 20,000-lb boat lift, personal watercraft lift, and a 40-foot dock on a deep-water canal, you’ll enjoy immediate access to Sarasota Bay, the Intracoastal Waterway, and the Gulf—with no fixed bridges along the way. End your days with breathtaking sunsets as the sky ignites in color, dolphins play, and manatees glide by. Inside, the home offers an optimal floor plan ready for your personal touches. The spacious eat-in kitchen features an expansive island perfect for casual entertaining, complemented by new stainless-steel appliances. A wall of sliding glass doors seamlessly blends indoor and outdoor living, filling the home with natural light and water views. All main living areas open to the pool and outdoor spaces. Recent updates include a new AC system and a recently refinished pool. The home offers three bedrooms and four baths, with the flexibility to modify the layout or easily add a fourth bedroom. A wood-burning fireplace adds warmth and charm to the living room. Located on the barrier island of Longboat Key, this exceptional property is perfectly suited for the most discerning buyers. Enjoy nearby golf, pickleball, boutique shopping, and dining, with St. Armands Circle and downtown Sarasota just minutes away. Convenient access to SRQ Airport makes this an ideal full-time residence or luxury vacation retreat. Call today to schedule your private showing and experience coastal living at its finest.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER (941-729-7400)
Listing Agent: Kathy Cahill (941-807-3565)
5231 GULF OF MEXICO DR #104, LONGBOAT KEY, FL 34228
$499,000186 Days on yellowkey MLS ID: A4676730
REDUCED by $46,000 (8.4%) on 06/15/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 720 Built: 1973 Tax: $6,784 (2024)Community: Covert IiCondo
Taxes:$6,784
Remarks: Have you dreamed of the perfect island getaway situated right on a gorgeous stretch of beach on Longboat Key? This is by far the lowest priced direct beachfront condo on the entire island and it is already completely updated! Whether you decide to use it yourself or use it as an investment with outstanding monthly rental income availability, this is the one. With a fabulous ground floor location, you can have your toes in the sand in only a few steps! This condo offers Italian porcelain tile throughout and a completely new kitchen with beautiful counter tops, all new cabinets and new appliances. The bathroom has been beautifully updated as well and features custom tile work in a seaside theme. The view is fabulous in either direction with the sparkling pool out front and the gorgeous Gulf of Mexico out back. The open living and dining area allows plenty of space to entertain or to quietly contemplate whether it’s a beach day, a day for a soak in the pool or a walk to the Covert bayside fishing pier. The bedroom offers the same stunning beach view and features storm rated sliders to the screened in lanai. The midkey location allows for easy access to multiple restaurants and shopping. The tree filled mangrove trails of Joan Durante Park are a birders’ paradise and the 12 mile long bike path give you many options to soak in the sun while getting in your daily exercise. This is island living at its best at a price you may never thought you could find!
Listing Agent: Jodene Moneuse, Pa (941-302-4913)
4720 GULF OF MEXICO DR #Villa 2, LONGBOAT KEY, FL 34228
$599,000135 Days on yellowkey MLS ID: A4679458
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 912 Built: 1974Monthly Fee: $1,305 Tax: $1,356 (2025)Community: Windward Bay AmdVilla
Taxes:$1,356
Remarks: Welcome to coastal luxury living in Windward Bay, one of Longboat Key's most sought-after waterfront communities. Perfectly positioned between the sparkling waters of Sarasota Bay and the pristine Gulf beaches, this completely renovated 2-bedroom, 2-bath villa offers an exceptional blend of modern elegance, resort-style amenities, and the coveted island lifestyle buyers dream about. Fully reimagined and rebuilt from the studs, this stunning residence showcases high-end craftsmanship and designer finishes throughout. Every detail has been thoughtfully upgraded, including brand-new electrical systems, plumbing, drywall, insulation, kitchen, bathrooms, fixtures, and finishes—providing the peace of mind and comfort of essentially new construction within an established waterfront community. The bright, open-concept floor plan is flooded with natural light and designed for effortless indoor-outdoor living. The beautifully appointed chef's kitchen flows seamlessly into the living and dining areas, creating an inviting space ideal for entertaining, seasonal gatherings, or everyday enjoyment. A dedicated 220-volt outlet offers convenient electric vehicle charging, adding modern functionality and future-ready convenience. One of the villa's most desirable features is its easy ground-level access with no stairs, making everyday living simple and accessible. Pet lovers will appreciate Windward Bay's generous pet-friendly policy allowing up to two pets, a rare and highly desirable amenity on Longboat Key. Step outside to your private patio retreat surrounded by lush tropical landscaping and mature greenery. Enjoy peaceful mornings with coffee, spectacular sunset skies, and relaxing evenings gathered around the fire pit just moments from beach access. The Gulf of Mexico is only steps away, offering endless opportunities for shelling, beach walks, swimming, paddleboarding, and breathtaking sunsets. Residents of Windward Bay enjoy an unmatched collection of resort-style amenities set across nearly 27 acres of beautifully maintained waterfront property, including: Three beach access points to the powdery sand beaches of Longboat Key. Nearly one-half mile of scenic waterfront walking paths and nature trails. Two heated swimming pools. Six tennis and pickleball courts. Fitness center, sauna, clubhouse, library, and social gathering spaces. Two private marinas with boat slips and jet ski slips (for rent and subject to availability). Private fishing pier with panoramic bay views. Kayak storage and launch areas. Outdoor grilling stations, fire pits, and waterfront gathering areas. Lush park-like grounds with mature tropical landscaping. Whether you're searching for a primary residence, seasonal retreat, second home, snowbird escape, waterfront villa, beach getaway, or investment opportunity, this move-in-ready residence offers an unparalleled combination of location, lifestyle, and value. Ideally located minutes to St. Armands Circle, Sarasota's vibrant arts and dining scene, championship golf courses, boating destinations, waterfront restaurants, and world-renowned Gulf Coast beaches, this exceptional property delivers the very best of Longboat Key living. Experience the ultimate in island living where luxury, comfort, boating, beach access, and resort-style amenities come together in one extraordinary coastal retreat.
Listing Agent: Sharon Austin (678-756-4020)
4340 FALMOUTH DR #D-204, LONGBOAT KEY, FL 34228
$479,00011 Days on yellowkey MLS ID: A4698081
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1072 Built: 1969 Tax: $5,411 (2025)Community: Longboat HarbourCondo
Taxes:$5,411
Remarks: Welcome to Longboat Harbour D-204, a beautifully maintained second-floor condominium in one of Longboat Key's most desirable gated waterfront communities. Ideally located in Building D—the closest building to the community's private Gulf beach access—this residence offers umatched convenience to the beach pavilion, showers, restrooms, and private beach lockers. Inside, you'll find a bright and comfortable floor plan featuring granite countertops, an in-unit washer and dryer, a spacious bedroom with a new impact window, and electric blinds. Additional highlights include a private storage locker, covered carport parking space, proximity to the elevator, a new roof, and all assessments fully paid. Longboat Harbour offers resort-style amenities including four heated swimming pools, a fitness center with sauna, tennis and pickleball courts, art studios, a woodworking shop, and a yacht club with a protected harbor. Located just miles from St. Armands, Lido Beach, Downtown Sarasota, Anna Maria Island, Homes Beach, and Bradenton Beach, this is the perfect opportunity to enjoy the best of Longboat Key waterfront and beach living.
Listing is courtesy of: WAGNER REALTY (941-383-5577)
Listing Agent: Jonna Humphries (941-465-2357)
626 BUTTONWOOD DR, LONGBOAT KEY, FL 34228
$4,495,00026 Days on yellowkey MLS ID: A4696767
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4106 Built: 2026Monthly Fee: $50 Tax: $4,789 (2025)Community: Longboat Shores RevSpa: YesSingle Family
Taxes:$4,789
Remarks: Experience the pinnacle of coastal living in this exceptional new construction waterfront residence, ideally situated in the heart of Longboat Key. Perfectly positioned across from the community marina with direct boating access to the Gulf of Mexico, this move-in-ready home offers an extraordinary blend of modern elegance, superior craftsmanship, and the relaxed sophistication of island life. Spanning 4,106 square feet, this thoughtfully designed residence features 4 spacious bedrooms, a private office/den, and 4 luxurious bathrooms, creating an ideal setting for both everyday living and entertaining. Finished floor elevation above base flood elevation, the home provides added peace of mind while maximizing its commanding presence. Designed to embrace Florida’s indoor-outdoor lifestyle, expansive sliding glass doors seamlessly connect the interior living spaces to two generous covered lanais, overlooking a resort-style heated pool and spa. Whether hosting sunset gatherings or enjoying a quiet morning overlooking the water, every space has been crafted to capture the beauty and serenity of waterfront living. Inside, sophisticated finishes and attention to detail abound. Wide-plank engineered hardwood flooring flows throughout the home, complemented by designer quartz countertops, custom cabinetry, and an open-concept floor plan filled with natural light. The chef-inspired kitchen serves as the centerpiece of the home, featuring an oversized island, premium finishes, and a spacious walk-in pantry. The convenience of dual laundry rooms further enhances the home's thoughtful design. For boating enthusiasts, the property features a concrete seawall and marina access, offering quick and convenient access to Sarasota Bay and the Gulf waters beyond—making it easy to enjoy world-class fishing, waterfront dining, and unforgettable days on the water. A boat slip is currently leased by the owner. Tucked away on a quiet street, yet just moments from Longboat Key’s pristine white-sand beaches, championship golf courses, marinas, boutique shopping, and renowned dining destinations, this residence delivers the perfect balance of privacy and accessibility. Offering the rare combination of new construction, waterfront location, elevated construction, luxury finishes, and Gulf boating access, 626 Buttonwood Drive represents an exceptional opportunity to own a premier Longboat Key waterfront retreat in one of Florida’s most coveted coastal communities. Luxury. Boating. Beach Life. Welcome Home.
5260 GULF OF MEXICO DR #413, LONGBOAT KEY, FL 34228
$550,0005 Days on yellowkey MLS ID: A4698906
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1155 Built: 1974 Tax: $2,618 (2025)Community: The Banyan Bay ClubCondo
Taxes:$2,618
Remarks: Move-in-ready condition, ground-floor bayside condominium with Sarasota Bay views and deeded private Gulf beach access in the sought-after Banyan Bay Beach Club! Discover effortless coastal living in this beautifully updated 2-bedroom, 2-bath residence offering 1,155 square feet on the bayside of Longboat Key. Thoughtfully renovated throughout, this inviting home features new luxury vinyl plank flooring, new kitchen appliances, updated bathrooms with new vanities, and a bright, open floor plan designed for comfortable island living. Enjoy Sarasota Bay views from the living room, primary bedroom, and private rear patio. Step directly from your patio onto the beautifully landscaped lawn, where you can enjoy your morning coffee, watch boats and dolphins pass by, observe abundant coastal wildlife, and welcome beautiful Florida sunrises. The convenient ground-floor location offers effortless access and seamlessly blends indoor and outdoor living. Residents of this pet-friendly community enjoy the best of both worlds with deeded private Gulf beach access and outstanding amenities, including a heated pool, clubhouse, pickleball, tennis, fishing pier, kayak storage and launch, and assigned parking. Whether you enjoy boating, kayaking, fishing, shelling, or relaxing on the beach, this community offers the quintessential Longboat Key lifestyle. Ideally located near championship golf, waterfront dining, marinas, boutique shopping, St. Armand's Circle, and downtown Sarasota, this exceptional residence is perfect as a primary home, seasonal retreat, or investment opportunity. Don't miss this rare opportunity to own an updated, move-in-ready, bayside condominium with Sarasota Bay views, deeded private Gulf beach access, and the relaxed elegance of island living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Bobbie Banan (941-356-2659)
4350 CHATHAM DR #105, LONGBOAT KEY, FL 34228
$310,00019 Days on yellowkey MLS ID: A4697241
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 747 Built: 1969Monthly Fee: $1,147 Tax: $1,457 (2025)Community: Longboat HarbourCondo
Taxes:$1,457
Remarks: Exceptional opportunity to own a beautifully furnished waterfront residence in a gated, amenity-rich boating community. This one-bedroom unit features hurricane-impact sliding glass doors and windows, allowing abundant natural light while providing peace of mind. Enjoy waterfront living with access to a private beach located at 4415 Gulf of Mexico Drive, complete with gated parking, indoor facilities, and beachside amenities. Residents have access to an impressive array of community features, including four heated swimming pools, a spacious fitness center, pickleball courts, tennis courts, kayak and bicycle storage, and a vibrant boating community with first-come, first-served boat slips. Additional amenities include a banquet hall and numerous social and recreational opportunities. Whether you're seeking a full-time residence, seasonal retreat, or investment property, this waterfront gem offers the perfect combination of coastal lifestyle, convenience, and value.
Listing Agent: Malihe Karimi (941-376-5099)
5655 GULF OF MEXICO DR #A107, LONGBOAT KEY, FL 34228
$799,00088 Days on yellowkey MLS ID: A4687549
1 Days Off yellowkey (back on 5/28/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1274 Built: 1975Monthly Fee: $1,164 Tax: $3,185 (2025)Community: Cedars West Of Longboat IncCondo
Taxes:$3,185
Remarks: Under contract-accepting backup offers. Experience the best of Gulf-front living and gorgeous views in this move-in-ready, two-bedroom, two-bath waterfront condominium, perfectly positioned in an elevated community just steps from the beach. This home is in impeccable condition and is designed for relaxation, with a seamless blend of comfort, style and convenience. It's being sold turnkey with lovely furnishings. The kitchen features new Samsung stainless steel appliances, plenty of counter space, and a comfortable sitting area. An open floor plan with a large living room, remote-controlled sunshades and three-panel impact sliding glass doors opens to an inviting screened lanai with a tropical ceiling fan, blurring the lines between indoor and outdoor living. There are ceiling fans in every room. The primary suite offers a large bath with a separate water closet and a huge walk-in closet. There are also impact sliders leading out to the lanai with a view of the Gulf. The guest suite is spacious with lots of closet space. The laundry is neatly tucked away and features Bosch machines. If you love the beach and enjoy stunning sunsets, Cedars West is really the perfect place to live. This location is walking distance to our local restaurants (Lo-Key, Harry's and Hugos), convenience shopping and all the amenities you’ll need to enjoy life here on Longboat Key. This community has tennis, a heated pool, BBQ area, bike racks, and kayak storage. Cedars East, just across the street, offers tennis membership with a world-class facility. This financially sound community offers peace of mind with a new roof and no assessments planned. With a liberal rental policy allowing up to 26 rentals/year, this property presents an exceptional investment opportunity while still offering the flexibility to enjoy your own beach getaway. There is a locking owner's closet in the unit. You have to see this home to really appreciate how special it is.
Listing Agent: Judy Mitchell (941-275-6838)
1945 GULF OF MEXICO DR #M2-402, LONGBOAT KEY, FL 34228
$515,0005 Days on yellowkey MLS ID: TB8525404
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 933 Built: 1978Monthly Fee: $1,333 Tax: $5,390 (2025)Community: Seaplace VCondo
Taxes:$5,390
Remarks: Seaplace Condominiums, half mile Gulf of Mexico beachfront property with chaise lounges & umbrellas provided on private beach portion. Assigned parking space is 590. I have "hurricane-impact doors & windows".
Listing is courtesy of: FLAT FEE MLS REALTY (813-642-6030)
Listing Agent: Stephen Hachey (813-642-6030)
2850 GULF OF MEXICO DR #4, LONGBOAT KEY, FL 34228
$325,0005 Days on yellowkey MLS ID: A4698791
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 532 Built: 1967 Tax: $3,248 (2025)Community: Neptune On Longboat KeyCondo
Taxes:$3,248
Remarks: Coastal Living on Longboat Key – Neptune Condominium Welcome to your island retreat at Neptune on Longboat Key, a charming boutique community just moments from the Gulf of Mexico. This beautifully updated 1-bedroom, 1-bath condominium offers the perfect blend of comfort, style, and an unbeatable Longboat Key lifestyle. Step inside to discover a bright, open floor plan featuring luxury vinyl flooring, coastal-inspired décor, crown molding, and a tastefully renovated kitchen with cabinetry, updated appliances, quartz-look countertops, and a deep stainless sink. The spacious living and dining area flows effortlessly onto a screened lanai where you can relax with a morning coffee. The generous bedroom provides a peaceful retreat with abundant natural light, while the updated bath and thoughtful finishes create a move-in-ready coastal escape. Located on the desirable south end of Longboat Key, Neptune is a small boutique community known for its quiet atmosphere and convenient location. You're just a short stroll to the beach and only minutes from St. Armands Circle, where you'll enjoy world-class dining, shopping, and entertainment. Downtown Sarasota, cultural attractions, golf, boating, and marinas are also just a short drive away. Neptune is a small, low-density community with minimal common amenities, helping keep ownership simple while offering a peaceful island setting. Whether you're looking for a full-time residence, seasonal getaway, or investment opportunity, this turnkey-furnished condo offers an exceptional opportunity to own a piece of paradise on Longboat Key.
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Michael Renick Pllc (941-400-8735)
1135 GULF OF MEXICO DR #505, LONGBOAT KEY, FL 34228
$1,175,00046 Days on yellowkey MLS ID: A4694362
5 Days Off yellowkey (back on 7/2/2026)
REDUCED by $125,000 (9.6%) on 06/03/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1503 Built: 1980 Tax: $13,396 (2025)Community: Beachplace ICondo
Taxes:$13,396
Remarks: Under contract-accepting backup offers. DIRECT BEACH FRONT VIEWS AND FIFTH FLOOR EXTRORDINARY PANORAMA! Come visit this property soon, as it boasts Two Parking spots, one in garage, near the elevator and one outside near the front door. Reimagined kitchen with lots of cupboard space, all KITCHEN AID appliances, 2019 Air Handler, never rented and barely occupied. Furnished with exquisite taste and comfortable living space! Beachplace is unique from other communities due to its high rental appeal for returning families! Enjoy the great Olympic size pool located in the center of the complex, plus the oversized hot tub, workout facilities, tennis courts, pickle ball and more! Not to forget the covered baby pool for ages 3 and under! The highest and most sought after units are always BEACHFRONT, holding the best value!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: James Weingart (440-623-9068)
803 BAYPORT WAY #803, LONGBOAT KEY, FL 34228
$775,000112 Days on yellowkey MLS ID: A4686552
1 Days Off yellowkey (back on 5/14/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1456 Built: 1981 Tax: $6,376 (2025)Community: Bayport Bch & Ten Ph ECondo
Taxes:$6,376
Remarks: Under contract-accepting backup offers. Welcome to the true tropical oasis of Bayport Beach & Tennis Club, a Longboat Key Gulf to Bay community. Bayport was designed by Tim Siebert, one of the founding architects of the renowned Sarasota School of Architecture and is recognized for its award-winning, timeless design. Bayport offers 27 lushly landscaped acres with 1,200 feet of private beach. This tastefully renovated second-floor unit offers two expansive bedrooms and two beautiful bathrooms and comes fully turn-key. This unit was curated with attention to detail and functionality in mind. The kitchen offers plenty of storage, stainless steel appliances, quartz countertops and beautiful accent details. Enjoy three patios that allow for great indoor/outdoor living. Fully equipped with Hurricane impact doors and windows. One under building parking space included, along with a locked storage closet - perfect for bikes and beach gear. When not at the beach, enjoy the meticulously kept nature trails, landscaped grounds and wildlife. Just steps away from the well appointed clubhouse is equipped with a Junior-Olympic sized heated pool, four har-tru tennis courts, a fitness center and more. In addition, Bayport residents are proud of their active social and recreational calendar. Water enthusiasts can utilize the secluded fishing pier that stretches out onto Sarasota Bay; to fish, watch the sunrise, the Manatees swim or the Egrets wading among the mangrove trees. Residents also benefit from conveniently located on-site paddle board and kayak launch and storage areas. Bayport residents enjoy an array of restaurants locally, and the convenience of a nearby supermarket, pharmacy and boutique shops. Recreational enthusiasts also benefit from the nearby Bayfront Park which offers a popular pickle-ball program, dog park and other bayside activities. The nearby Longboat Key Club offers private access to championship waterfront golf, extensive leisure activities and boating facilities. Within minutes, one can access the famous St Armand's Circle with its exceptional shopping and dining amenities. From there, cross the iconic Ringling Bridge to downtown Sarasota, which is well known for world-class theater, culture and dining.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Alexis Smith-Frady (352-225-1724)
1211 GULF OF MEXICO DR #701, LONGBOAT KEY, FL 34228
$2,125,00035 Days on yellowkey MLS ID: A4694983
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2100 Built: 1985 Tax: $17,857 (2025)Community: PromenadeSpa: YesCondo
Taxes:$17,857
Remarks: Virtually Staged. Sweeping sunrise to sunset views define this beautifully reimagined 7th floor residence at the Promenade on Longboat Key. Fully renovated in 2026, this three-bedroom, three full bath home offers floor to ceiling windows, abundant natural light, and 180- degree views of both the Gulf of Mexico and Sarasota Bay. The double door entry opens to a freshly painted residence with new luxury plank flooring, nine-foot ceilings and modern lighting throughout. This residence is designed for entertaining with a large open living area and a full wet bar and wine refrigerator. The kitchen features quartz countertops and full quartz backsplash, Sub-Zero refrigerator, Cafe stove and double convection oven, and matching panel dishwasher. The custom modern white soft closed cabinetry with polished nickel hardware provides a stylish look as well as large amounts of storage and pantry space. A reimagined kitchen layout allows for a separate island that can be used for morning coffee, workspace or meal preparation all while enjoying gorgeous bay views. The primary suite features a spa-like oasis with new enlarged glass enclosed shower featuring waterfall and wall shower-heads, all quartz countertops, dual sinks, polished nickel faucets, fully backlit electric mirrors, separate water closet, linen storage and a custom designed walk-in closet. The two additional bedrooms each offer private bathrooms, one with a dazzling walk-in shower and the other with a new bathtub/shower. The renovations included removing all popcorn ceilings, updates to electrical and plumbing systems, all new fire sprinkler hardware and base boards. The full-sized laundry room includes new storage cabinetry, full sized washer/dryer and a wash-sink. All new interior doors fitted with Emtek polished nickel door hardware. The residence includes a private storage locker that is humidity and temperature controlled and a deeded underground parking space. The Promenade has undergone significant renovation over the past few years and features elegant marble foyer, 24-hour gate security, manned concierge desk, his and hers fitness rooms with shower and sauna, luxurious party rooms, EV charging station, a well-maintained pool deck and hot tub, verdant tropical landscaping and dual BBQ areas. The beach is located directly behind the building and features a secure entrance and beach chairs. There are also 4 Har-Tru tennis courts to complete the Longboat Key lifestyle. The Promenade is located near the south end of Longboat Key, minutes from St. Armand's Circle and the restaurants and arts offerings of downtown Sarasota. The Longboat Key Club and its golf, tennis and marina offerings is available for membership and just outside the property.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Maggie Hicks (941-321-1759)
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