Location: Sarasota , 34242
Do Not Show Listings
316 BEACH RD, SARASOTA, FL 34242
$5,499,00054 Days on yellowkey MLS ID: A4683801
Bed: 8 Bath: 9.0 Gar: 2 Liv Area Sq Ft: 4681 Built: 1996 Tax: $37,822 (2025)Community: Sarasota BeachSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$37,822
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Just steps from the shoreline, this coastal home offers deeded beach access and sweeping panoramic views of the Gulf. Thoughtfully designed across three living levels and serviced by a private elevator, the home features 8 bedrooms, 8 full baths, and 2 half baths, with expansive gathering spaces suited for both everyday living and hosting. The top floor serves as the heart of the home, where the main kitchen and primary living area open directly to a Gulf-facing balcony showcasing breathtaking, unobstructed water views. This elevated vantage point creates a stunning backdrop for daily living, with the kitchen, dining space, and great room all positioned to take in the scenery. A secondary club room with wet bar provides an additional space to gather, while multiple balconies throughout the home frame the coastal setting from different vantage points, including select bedroom suites. Below, the outdoor living space features a private pool and integrated spa surrounded by lush landscaping, along with a fully equipped outdoor kitchen with built-in grill, refrigeration, and dining area. All eight bedroom suites offer ensuite baths and generous accommodations, with several enjoying Gulf views and private balcony access. This income-producing property offers flexibility for personal enjoyment, investment potential, or both. Located near beach access and Siesta Key Village, this is a rare opportunity to own a well-positioned coastal home that blends lifestyle appeal with proven performance.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
1200 SIESTA BAYSIDE DR #1200G, SARASOTA, FL 34242
$475,00034 Days on yellowkey MLS ID: A4685175
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 845 Built: 1988 Tax: $4,441 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$4,441
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Welcome to the world-famous Siesta Key! Now available a second-floor one-bedroom, one-bath condominium in the desirable Gulf and Bay Club Bayside. This particular condo had zero flood or storm damage. This home is just waiting for your personal touch! Enjoy direct deeded beach access just across the street to Siesta Key Beach and live a true resort-style life with wonderful amenities at your fingertips. An open floor plan greets you with tile on the diagonal, a spacious living/dining area, and a balcony overlooking the community pool. The unit is complete with a private one-car garage, indoor laundry with a brand-new stackable washer and dryer, and turnkey furnished and ready for you or your guests. Gulf and Bay Club Bayside features: Two resort-style pools Tennis and pickleball courts Newly renovated fishing dock Walking paths, boat loading zones, and four BBQ areas Clubhouse for private parties and events. This weekly-rental-friendly community also offers onsite management (directly below the unit), making it a great income opportunity for investors or those seeking a snowbird property. Location cannot be beat you just cross the road for beach access or take the free trolley to explore Siesta Key Village or South Siesta! Live the island lifestyle at Gulf and Bay Club Bayside. Tenant occupied best showing time Saturday but with enough notice we can manage a showing. Must be scheduled and approved by tenants.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Jessica Ross, Pa (941-321-9000)
5830 MIDNIGHT PASS RD #107, SARASOTA, FL 34242
$649,00088 Days on yellowkey MLS ID: A4679302
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 921 Built: 1970 Tax: $4,451 (2025)Community: Jamaica RoyaleCondo
Taxes:$4,451
Remarks: Welcome to your slice of paradise at Jamaica Royale on world famous Siesta Key Beach. This completely remodeled 2 bedroom, 2 bath condo offers the perfect blend of coastal elegance and income producing potential. The stunning kitchen features quartz countertops, custom wood cabinetry, stainless steel appliances, dining space, and a laundry closet with stackable washer and dryer, ideal for entertaining after a day on the sand. Both bathrooms have been beautifully updated with designer finishes, including marble like tile shower and sleek quartz-top vanities, creating a spa like retreat. The thoughtfully designed floor plan is comfortable, stylish, and Turn-key move-in ready. Located in a highly desirable beachfront community with one week minimum rentals, this condo is an excellent investment or vacation getaway. Enjoy a heated pool and approximately 300 ft of private beach frontage, just steps from the Gulf’s crystal clear waters and powder soft sand. Ideally situated near Siesta Key Village, you’re moments from renowned dining, boutique shopping, and vibrant night life. Whether you are seeking a personal retreat, rental income, or both, this is coastal living at it’s best!
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Jennifer Bright (941-320-4989)
4660 OCEAN BLVD #Q1, SARASOTA, FL 34242
$525,000242 Days on yellowkey MLS ID: A4659204
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971 Tax: $7,101 (2024)Community: Sea VillageCondo
Taxes:$7,101
Tax Year: 2024
Remarks: PRICED TO SELL! New hurricane-impact sliders have been ordered and will be installed prior to closing. Experience million-dollar, direct Gulf views from this ground floor condominium in the sought after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring throughout, and plantation shutters. Hurricane-impact windows provide peace of mind and lasting value. Additional features and upgrades include a 2021 water heater, 2022 HVAC, 2023 electrical panel, in-unit washer and dryer, designated parking, storage shed, and bike storage. Sea Village offers residents a true coastal lifestyle with a heated waterfront pool, tropical grounds, and easy access to dining, shopping, and Siesta Key’s vibrant village. Covered parking and generous guest parking make entertaining convenient. Perfect as a primary residence or seasonal retreat, this home blends unmatched views with modern upgrades in one of Sarasota’s most desirable island communities.
Listing Agent: Halie Monde (941-735-4707)
3607 FLAMINGO AVE, SARASOTA, FL 34242
$4,950,000206 Days on yellowkey MLS ID: A4662402
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3876 Built: 2005 Tax: $17,596 (2024)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$17,596
Remarks: DIRECT ACCESS TO INTRACOASTAL WATERWAY - North Siesta Key's Bay Island Boater's Dream - Experience the best of coastal living in this elegant 4bd/4ba residence - just minutes to the Intracoastal Waterway. The home features a 2023 14,000lb dock/lift with electric and 3pnt moorage. Step inside a welcoming slate tile entry foyer to discover timeless quality design with Brazilian Ipe hardwood flooring throughout, hurricane rated windows and French doors and volume ceilings. At the heart of the home is a true cook's kitchen with Wolff Gas Range, built-in Sub-Zero stainless refrigerator, Fisher Paykel dishwasher and soap-stone counter-tops. A true Chef's pantry, abundant cabinetry and full bar with wine refrigeration elevate the entertaining experience. The Primary Bedroom Suite, set in its own private wing, offers a tranquil retreat w/French Doors opening to a full private deck, perfect to enjoy sunrise and coffee; generous closet space and spa-inspired Bath; Guests Private wing and other rooms offer flexibility; French doors, automated window coverings, and architectural details create a refined and comfortable atmosphere. A full laundry room w/sink, office nook and mudroom are conveniently located off the 3-car garage. Outdoors, enjoy multiple covered decks, one with gas-fireplace for perfect evening waterfront ambiance; overlooking heated salt-water pool/spa; lush tropical landscape; Minutes to downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Maria Beck, Pa (646-531-4118)
4822 OCEAN BLVD #11E, SARASOTA, FL 34242
$419,0005 Days on yellowkey MLS ID: TB8498225
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 820 Built: 1973 Tax: $4,517 (2025)Community: Siesta TowersSpa: NoCondo
Taxes:$4,517
Remarks: 11th-floor Gulf views, Siesta Key Beach right down the road, and a price point that gives you real upside. This the kind of condo/value comination people hope for. The unit has modest finishes as it sits, but the real play here is the value. You get a front-row seat to the Gulf, a private balcony for sunsets every night, and the chance to update it the way you want without paying a premium for someone else’s remodel. This is a bright west-facing 1-bedroom in Siesta Towers, so the natural light and water views are the star of the show. Whether you want a full-time place, beach getaway, or investment hold, this one checks the box for location and long-term potential. Siesta Towers is a well-kept beachfront community with a community pool, covered parking assigned by seniority, updated lobby/amenities, and beautifully maintained grounds. The building completed its milestone inspection in 2024, major exterior repairs were done in 2023, the roof was replaced in 2018, and the association fully funds both mandatory structural reserves and general reserves. You are also right in the middle of what makes this area so desirable. Siesta Key Beach is close by, and Siesta Key Village is right there for dining, shopping, and nightlife. It is hard to beat this combination of views, location, and value on Siesta Key.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Nathan Shirk (585-356-2197)
6263 MIDNIGHT PASS RD #301, SARASOTA, FL 34242
$749,90038 Days on yellowkey MLS ID: TB8486242
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2018 Built: 1981 Tax: $9,637 (2025)Community: Excelsior Beach To Bay 7Spa: YesCondo
Taxes:$9,637
Remarks: Welcome to coastal living at its finest in the highly sought-after Gulf-to-Bay community of Excelsior Beach to Bay on world-famous Siesta Key. Perfectly positioned in Building One, this 3 bed/3 bath, spacious third-floor residence offers over 2,000 square feet of bright, open living space with partial Gulf views and a unique architectural design rarely found in condominium living. From the moment you enter, soaring vaulted ceilings and an elegant spiral staircase create a dramatic focal point while expansive living and dining areas invite both relaxation and entertaining. Large windows and sliding glass doors lead to a 19x5 enclosed lanai, the perfect spot for morning coffee, reading, or a quiet workspace surrounded by natural light and tropical scenery. The well-appointed kitchen features generous cabinetry, granite countertops, and a convenient pass-through to the living area, allowing seamless interaction with guests and family. The spacious primary suite serves as a private retreat with a large ensuite bath featuring a walk-in shower and soaking tub, while two additional bedrooms and bathrooms provide ideal accommodations for guests, family, or rental flexibility. A new HVAC system offers peace of mind and efficiency, and the residence also includes in-unit washer and dryer, assigned under-building parking, a private storage unit, and additional guest parking. Excelsior Beach to Bay is one of Siesta Key’s most desirable communities, offering a true resort-style lifestyle with private beach access just steps away across Midnight Pass Road, allowing you to walk directly to the powder-soft quartz sand of Siesta Key Beach. Residents enjoy an impressive array of amenities including two heated pools and spas, lively pickleball and tennis courts, a fitness center, fishing pier and bay front dock, library, beautifully maintained tropical grounds, and an active social atmosphere welcoming residents of all ages. With a two-week minimum rental policy, this property presents an outstanding opportunity for full-time residents, seasonal owners, or investors seeking strong rental potential in one of Florida’s most iconic beach destinations, with onsite management available. Owners may have one small pet. Located just minutes from the vibrant Siesta Key Village with its waterfront dining, boutique shopping, and entertainment, this exceptional residence offers the perfect combination of location, lifestyle, and investment opportunity in one of the Gulf Coast’s most coveted communities. Make your appointment today! Life is Short - Buy the Beach House!
Listing Agent: Mindy Smith, Pa (727-599-5534)
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,595,00026 Days on yellowkey MLS ID: A4687301
REDUCED by $100,000 (1.8%) on 04/16/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$25,684
Remarks: Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Samantha Callaway (630-865-3189)
332 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,595,00027 Days on yellowkey MLS ID: A4687188
Bed: 9 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 4055 Built: 2019 Tax: $26,520 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$26,520
Remarks: ~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautiful home boasts 8 bedrooms + an additional bonus room = 9, plus 8 bathrooms, including 6 en-suite retreats, perfectly suited for a large primary residence or a high-performing luxury vacation rental. Ideally located and just steps from premier dining, boutique shopping, & vibrant nightlife, and only a short stroll or bike ride to the world-renowned Siesta Key Beach. This property offers the ultimate blend of convenience with the feel of a resort-style escape. Upon entering take the stairs or the convenient elevator up to the main living space. Here you will find an open chef's kitchen, large island, a beverage bar, along with the spacious living room and dining area. There are 2 bedrooms also on this level. Multiple balconies showcase great views of the village, while the home’s prime location places you moments from everything Siesta Key has to offer. It has been thoughtfully designed with high-end designer finishes and furnishings, every detail for both comfort and entertaining. The bonus room on the 4th level leads out to a spiral staircase and then up to the rooftop deck where both village and GULF VIEWS create a great backdrop for stunning SIESTA SUNSETS. Back on the 1st level, walk out to the covered patio and enjoy your private outdoor oasis with lush landscaping and the tranquil heated pool & spa designed for both relaxation and entertainment. It features an oversized sun shelf, wraparound lounge ledge and in-water bar seating. Whether you're hosting family and friends, a large group getaway or seeking a luxury investment property, this extraordinary beach house delivers unmatched living spaces throughout. It also comes beautifully turnkey furnished and ready for immediate enjoyment or rental income. THIS IS YOUR COASTAL ESCAPE...where luxury, location, and lifestyle all meet!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sabrina Ullmann (203-300-8181)
20 WHISPERING SANDS DR #1201, SARASOTA, FL 34242
$1,195,00098 Days on yellowkey MLS ID: A4678026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,398 Tax: $10,552 (2025)Community: Whispering SandsCondo
Taxes:$10,552
Remarks: A truly RARE offering, this TOP floor, GULF FRONT penthouse residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL GULF views from this unit unfurl in every direction, offering a daily masterpiece of colors that shift with the rising and setting sun. Wake up to breathtaking Gulf views that seem to stretch to infinity, offering a tranquil retreat from the ordinary. In the evening, enjoy the golden hues of Florida sunsets and starlit dinners from your expansive 28’ balcony, where the Gulf breezes and soft cries of the seagulls serve as the perfect soundtrack. This penthouse is more than just a property – it’s also a canvas for your imagination. Distinctive architectural elements and premium untapped potential invite you to curate a space that reflects your own unique style and vision. Whether you envision modern sophistication, coastal charm, or timeless elegance, the untapped possibilities of this unit invite your imagination to run free as you create the ultimate sanctuary tailored to your personal vision. Whispering Sands' relaxed, informal lifestyle provides the perfect backdrop for your next chapter. Start your day with a set of vigorous laps or water aerobics in one of two beautiful, heated pools - one beachside, one clubside. You’ll never need to leave the property to get your gym workout in the main clubhouse currently undergoing a complete remodel. Plant your feet in the cool quartz sand and enjoy daily dips in the balmy Gulf. Beach loungers are set out daily for the exclusive use of owners. Enjoy an impromptu game of beachside shuffleboard followed by a picnic supper at the Tiki Hut. Whether spending time exploring the vibrant cultural offerings of Sarasota just across the North Bridge, indulging in the local arts scene, or simply relaxing on your breezy private balcony with a good book, the options this property offers are endless. Secure your private viewing of this unique residence and claim your place in this coveted coastal community!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
191 VISTA HERMOSA CIR, SARASOTA, FL 34242
$570,00074 Days on yellowkey MLS ID: A4680721
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 993 Built: 1971Monthly Fee: $1,104 Tax: $4,566 (2025)Community: Vista HermosaVilla
Taxes:$4,566
Remarks: One or more photos have been virtually staged. Welcome to your maintenance free, dream beach retreat on Siesta Key! This charming and meticulously remodeled 2-bedroom, 2-bath villa offers the perfect blend of luxury and convenience, just a short stroll from the pristine sands of Crescent Beach. Enjoy cooking in a stunning kitchen featuring brand new quartz countertops, stainless steel appliances, and stylish light fixtures. Experience comfort year-round with newly installed HVAC and energy-efficient tankless water heater. Luxury vinyl panel floors flows seamlessly throughout, offering both durability and aesthetic appeal. Relax in the attached, screened-in lanai, complete with No-See-Um screen, aluminum framing and a new Hunter, wet-rated ceiling fan, perfect for warm island evenings. Both bathrooms have been beautifully remodeled providing a fresh, contemporary feel. Located just a few steps from the Clubhouse, heated pool, outside grilling areas and laundry facility. Walking distance to shops, restaurants and entertainment. Enjoy the easy, island lifestyle with access to the free trolley service to Siesta Key Village for even more shopping and dining experiences. Ideal for a second home, rental investment, or full-time residence. Don't miss this great opportunity to own a piece of paradise! Schedule your showing today and embrace the Siesta Key lifestyle!
Listing Agent: Denise Barbato (941-400-8773)
157 VISTA HERMOSA CIR, SARASOTA, FL 34242
$569,00084 Days on yellowkey MLS ID: A4677280
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1971Monthly Fee: $1,041 Tax: $3,568 (2025)Community: Vista HermosaVilla
Taxes:$3,568
Remarks: Completely renovated in 2025, this 2 bedroom/2 bath, maintenance free villa is walking distance to the powdery sands of beautiful Crescent beach on Siesta Key. Great opportunity for a second home, vacation rental or full-time residence. 2-week minimum, 26 times a year rental policy. All kitchen upgrades include new cabinets, quartz countertop, sink and all new stainless steel appliances including, microwave, refrigerator, stovetop and dishwasher. Convenient all new washer and dryer in unit! New tile flooring throughout. Amenities include a renovated clubhouse with full kitchen, heated swimming pool and outdoor grilling areas. This well-managed island retreat is located just a short distance to restaurants, shopping, entertainment and water sports. Enjoy the stress free, beach lifestyle of Siesta Key!
185 VISTA HERMOSA CIRCLE, SARASOTA, FL 34242
$575,000193 Days on yellowkey MLS ID: A4667525
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1971Monthly Fee: $1,041 Tax: $5,222 (2024)Community: Vista HermosaSpa: NoVilla
Taxes:$5,222
Remarks: Welcome to Vista Hermosa, your ultimate maintenance-free, island retreat a short stroll from the powdery sands of Crescent Beach on world renowned Siesta Key. This beautifully renovated villa is turnkey-furnished and move-in ready with brand new upgrades including luxury vinyl flooring throughout, quartz countertops in kitchen and bath, stainless steel appliances including, dishwasher, stove top and microwave and a newly installed A/C system. Amenities include a renovated club house with full kitchen, heated swimming pool and grilling areas. Vista Hermosa is located just a short distance to restaurants, shopping, entertainment and water sports. Enjoy the convenience of living close to Stickney Point bridge where you can venture off the Key and within a short drive visit Downtown Sarasota, St. Armand's Key, Longboat and Lido Keys. Great opportunity for a second home, vacation rental or full-time residence. 2-week minimum, 26 times a year rental policy allows for great income potential! Own a piece of paradise and enjoy the laid back, tropical lifestyle of Siesta Key. Schedule a showing today!
1255 E PEPPERTREE DR #201, SARASOTA, FL 34242
$499,000252 Days on yellowkey MLS ID: A4661191
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1460 Built: 1972 Tax: $5,890 (2024)Community: Peppertree Bay ISpa: NoCondo
Taxes:$5,890
Remarks: Move in ready AND priced to sell quickly! Don't miss the chance to own this beautifully updated turnkey furnished 2-bedroom condo at Peppertree Bay, available at an unbeatable price! Experience resort-style living in this bayfront and beachside community. The interior boasts an open floor plan with spacious, welcoming rooms, tile and luxury vinyl plank flooring, and a generous 29-foot lanai. Peppertree Bay offers luxurious amenities, including under building parking, private beach access, two heated swimming pools, tennis and pickleball courts, two clubhouses, a fitness center, and a fishing pier. It’s like a vacation every day! When you want a change of pace, leave your car behind and take the trolley to all the wonderful restaurants and shopping Siesta Key has to offer. With onsite management and a rental desk, this Peppertree Bay condo serves as an ideal coastal getaway or a smart investment choice. Don’t let this one get away.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
527 FREELING DR, SARASOTA, FL 34242
$5,825,000126 Days on yellowkey MLS ID: A4669657
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 4310 Built: 2026 Tax: $6,458 (2024)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$6,458
Remarks: Under Construction. The exterior presentation of this spectacular waterfront residence is most impressive with its blend of modern architecture and refined luxury. With superior elevation high above the water’s edge on Siesta Key’s prestigious Bay Island, this new to-be-built 4,310 sq. ft. residence is an unparalleled oasis of tranquility in a breathtaking setting. A place where architectural elegance and natural beauty converge in perfect harmony with elaborate artisanal work, functional design, and top-tier amenities. For boaters, the location is ideal with a new seawall and a private dock allowing quick access to the bay and gulf beyond. Built with intention and quality, large windows flood the space with natural light illuminating the graceful enhancements within. When entering the home through the 4-car garage, an elevator takes you to the first and second living levels. An elegant foyer entry with double-height ceiling and sleek iron-railed staircase usher you into the spacious interiors where every detail, from the fluid layout to the custom finishes, is thoughtfully curated. Adding a distinctive touch to the stunning great room are 20-foot ceilings and a two-story entertainment wall flanked by artistic display niches. A wall of glass sliders sets a dramatic tone, framing water views and uniting indoor-outdoor living. Designed for effortless entertaining and timeless family gatherings, the outdoor area overlooks the water to create a tranquil setting that feels both secluded and well-connected. With nearly 500 sq. ft. of covered lanai, an outdoor cook center and a heated pool/spa, there’s ample opportunity for hosting special gatherings or simply enjoying the quiet beauty laid before you. Lovely landscaping, lush greenery and outdoor spaces add to the home's overall aesthetic appeal. A remarkable gourmet kitchen is designed for functionality and style, equipped with high-end finishes, top-tier appliances, a large island and a butler’s pantry with additional refrigerator and dishwasher. An adjoining dining room comfortably seats 8-10 and offers wonderful water views while dining. The primary wing is remarkable with an exquisite spa bath, enlarged customized wardrobe room, and direct access to the laundry facilities. The first level also includes a den suite ideal for remote work or creative pursuits and a completely private guest bedroom with its own full bath. Upstairs, there’s an overlook to the great room below, 2 bedrooms, 2 full baths, and an amazingly-sized bonus room with private balcony. The award-winning and talented team of professionals at Allegra Homes has thoughtfully and expertly created a residence offering a secure, exclusive lifestyle in one of Sarasota's most sought-after and high-value areas. The construction quality is of the highest standard, ensuring that the home is both beautiful and built to last. Just minutes to the mainland, downtown’s cultural mecca, world-class dining and shopping venues, gorgeous area beaches and a top-ranked school system coveted by families for generations, the prized waterfront location couldn’t be better. Showcasing extraordinary craftsmanship throughout, this never-lived-in showplace is the ultimate vision for those who value the very best of coastal Florida living. There’s still time to make your own personal choices for creating the perfect custom home tailored to your family’s taste and style.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1260 DOLPHIN BAY WAY #404, SARASOTA, FL 34242
$1,395,000139 Days on yellowkey MLS ID: A4673762
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1997 Tax: $12,793 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,793
Remarks: ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a single family home with charm and character. The kitchen was custom built by Yoder Construction, a well-known local company, highly respected for their craftsmanship. Living room and dining area are bright and spacious. The large primary bedroom has a walk-in closet and ensuite with shower and separate soaking tub. There are two other ensuite bedrooms. All three bedrooms have California Closet systems. All windows have custom plantation shutters, adding to the charm and comfort of this amazing condo. You will want to spend your day on the light filled lanai, perfect for entertaining or simply relaxing. Dolphin Bay is a highly desirable, gated, pet friendly, 50-unit complex with a fun filled community atmosphere with three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier and kayak access. Dolphin Bay is well maintained with a freshly updated exterior and new elevators in 2024 and beautifully landscaped grounds. Just a short walk to the world famous, white crystal sands of Siesta Key beach.
5780 MIDNIGHT PASS RD #210, SARASOTA, FL 34242
$999,000139 Days on yellowkey MLS ID: A4673708
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $9,269 (2025)Community: Gulf & Bay Club Ph 2Condo
Taxes:$9,269
High School: Riverview High
Remarks: BEST VALUE AT SIESTA KEY BEACH GULF & BAY CLUB. Imagine living in Paradise…Welcome to your dream home on Siesta Key, where every day feels like a vacation. This beautiful beachfront corner unit in the prestigious GULF & BAY CLUB is located on the #1 Beach in America per Trip Advisor. Step into this stunning two-bedroom, two-bathroom unit, filled with natural light from expansive windows. Enjoy breathtaking sunrise and sunset views as part of your daily routine. The renovated interior features high ceilings, a gourmet kitchen with an office, modern bathrooms, smart storages and elegant details. Gulf & Bay Club is the gated resort community on the key. The serene property spans on 32 acres with 800 feet of private quartz sand beach, offering exceptional living. Beyond your home, Gulf & Bay Club offers world-class amenities, including scenic pathways to a freshwater lake with a rustic footbridge, a lush tropical courtyard with 3 heated pools, 6 pickleball courts, 4 tennis courts, 2 clubhouses and barbecue grills for social gatherings. Fitness enthusiasts can access a commercial gym, sauna, and media facility, while EV charging stations promote eco-friendliness. With an on-site rental management for one-month minimum rentals, this property is perfect for luxurious living and smart investment. Make this waterfront oasis your home where warm hospitality and serenity await.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Melanie Albaric (941-233-0957)
843 NORSOTA WAY, SARASOTA, FL 34242
$5,499,000111 Days on yellowkey MLS ID: A4676472
0 Days Off yellowkey (back on 2/11/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2467 Built: 1963 Tax: $51,752 (2025)Community: Bay IslandSpa: NoSingle Family
Taxes:$51,752
Remarks: Under contract-accepting backup offers. Set along one of Siesta Key’s most coveted bayfront streets, this exceptional property offers some of the most breathtaking views in all of Sarasota—spanning open water, the city skyline, and endlessly changing sunsets. Positioned in an enclave of multi-million-dollar homes, the location alone is extraordinary, with deep, open boating water and immediate access to Sarasota Bay. While the true value lies in the irreplaceable bayfront land, the home itself has been recently remodeled and exudes a charming Siesta Key cottage vibe—warm, inviting, and perfectly suited for relaxed coastal living. Thoughtful updates blend seamlessly with the home’s character, creating a space that feels both comfortable and refined. Outdoors, enjoy a private pool overlooking the water, ideal for entertaining or unwinding after a day on the bay. A two-car garage provides convenience and storage, while the property’s proximity to world-famous Siesta Beach, downtown Sarasota, and Sarasota Memorial Hospital offers unmatched lifestyle appeal. Whether envisioned as a serene waterfront retreat, a rental investment, or the future site of a custom estate, this bayfront opportunity combines remarkable views, premier boating, and one of the finest locations on Siesta Key.
Listing Agent: Tom Cail, Pa (941-780-2245)
276 ISLAND CIR, SARASOTA, FL 34242
$3,100,000198 Days on yellowkey MLS ID: A4667090
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2292 Built: 2026 Tax: $13,048 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$13,048
Remarks: Under Construction. Update as of 4/15/26: The home is nearly completed! Landscaping will be completed by 4/16. Inside, the final painting has taken place. There are a few odds and ends left that are almost finished! Call today to arrange your private showing! Photos are of a previous model, finishings vary. Located less than a half mile from the world-famous Siesta Key Beach, this brand-new coastal retreat is nestled on Palm Island, one of the Key’s most coveted waterfront enclaves. Sophisticated yet welcoming, this four bedroom, three bathroom home is thoughtfully designed and set on an oversized lot with a brand new 107-foot seawall. Built by Clark Horne Construction, this home showcases exceptional craftsmanship, quality materials, and thoughtful design throughout. Step through double doors into a sunlit open floor plan where every detail has been curated for modern coastal living. The gourmet kitchen is as functional as it is beautiful, featuring a Wolf range with custom hood, paneled Sub-Zero refrigerator, Bosch paneled dishwasher, Sharp microwave drawer, and a wine cooler showcased within a stunning glass-door pantry. Elegant statement lighting highlights waterfall quartz countertops, creating the perfect ambiance for quiet evenings or vibrant gatherings. The primary suite is a true sanctuary, offering volume ceilings, a spa-inspired bath, two spacious walk-in closets, and sliding glass doors that open directly onto the resort-style pool deck. Designed for seamless indoor-outdoor living, the oversized lot provides room to roam and enjoy waterfront activities—from kayaking and paddle boarding to simply soaking in the serene setting. Here, a sparkling pool and flush spa overlook tranquil canal views, completing this tropical paradise of comfort and relaxation. The expansive covered patio and entertainment-ready pool deck make every day feel like a getaway. Situated just moments from the quartz-white sands of Siesta Key Beach and the vibrant Siesta Key Village, you'll enjoy easy access to dining, boutique shopping, and live entertainment. On Palm Island, every day is a retreat—boat from your backyard, walk to the beach at sunset, and return to your own slice of tropical paradise. Call today to schedule your private showing!
Listing is courtesy of: CELLA'S REAL ESTATE INC (941-952-8649)
Listing Agent: Michael Cella (941-952-8649)
6157 MIDNIGHT PASS RD #E63, SARASOTA, FL 34242
$420,000242 Days on yellowkey MLS ID: A4662792
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1101 Built: 1974 Tax: $5,101 (2024)Community: Bay OaksCondo
Taxes:$5,101
Remarks: Secure This Siesta Key Condo Before it's gone! Priced to sell and ready to rent! Don’t wait - own a turnkey 2-bedroom, 2-bath condo in the highly desirable Bay Oaks community. Just minutes from the world-famous white sands of Siesta Key Beach. With weekly rentals allowed, this condo is perfect for a vacation getaway, short-term rentals, your personal island retreat, or full-time Florida living. Fully furnished and move-in ready. Enjoy poolside views from your screened porch, low HOA fees, and resort-style amenities including a heated pool, tennis courts, waterfront BBQ area, community room with pool table, and a fishing dock set in a lush, park-like setting along the bay. Centrally located on Siesta Key, you’re minutes from North and South Village shops, restaurants, and the free island trolley. Seller says bring offers. Act now - Make this Siesta Key condo your island paradise this spring!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Greg Hudson (941-302-1485)
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