Location: Sarasota , 34242
Do Not Show Listings
5780 MIDNIGHT PASS RD #110, SARASOTA, FL 34242
$1,299,000154 Days on yellowkey MLS ID: A4683108
REDUCED by $50,000 (3.7%) on 05/29/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $10,806 (2025)Community: Gulf & Bay ClubCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,806
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to the effortless rhythm of island living at Gulf & Bay Club, one of Siesta Key’s most prestigious beachfront communities. Behind the 24-hour guard-gated entrance, this beautifully remodeled, rarely available, three-bedroom residence offers the perfect blend of comfort, privacy, and resort-style living in a setting that feels worlds away from the everyday. Positioned on the first floor as a bright end unit, the home is surrounded by windows on three sides, filling the interior with natural light and creating a relaxed coastal atmosphere throughout. The thoughtfully redesigned floor plan opens beautifully for entertaining, with elegant finishes and carefully curated upgrades that make the residence feel both sophisticated and welcoming. The kitchen was designed with gathering in mind, featuring custom cabinetry, quartz countertops, marble backsplash, and premium Bosch appliances including induction cooktop and stainless vent hood. An additional built-in entertaining area with beverage refrigeration and extra storage makes hosting friends and family effortless. Living and dining areas flow naturally to the private lanai overlooking tropical landscaping and a tranquil lagoon, just steps to one of the community’s three pools, where evenings are often spent enjoying the peaceful surroundings and the soft glow of Siesta Key sunsets. The three-bedroom layout provides exceptional flexibility, whether for hosting guests, accommodating family, or creating a quiet home office. The primary suite offers a peaceful retreat with a walk-in closet and a beautifully updated bath featuring custom cabinetry, quartz countertops, and an expanded designer-tiled shower. Extensive renovations throughout the home include raised ceilings, smooth-finish walls, luxury flooring, updated lighting and electrical systems, new ductwork, upgraded panel box, air handler, and quick-recovery water heater. Importantly, the residence did not experience water intrusion during the recent hurricanes, offering additional peace of mind. Life at Gulf & Bay Club is defined by its resort-style amenities across 32 gated beachfront acres and 800 feet of Siesta Key’s famous quartz sand beach. Residents enjoy three heated pools including a lap pool, tennis and pickleball courts, racquetball, a large fitness center, beautifully landscaped walking paths surrounding the freshwater lagoon, clubhouses for gatherings, electric vehicle charging stations, and professional on-site management — all within a secure 24-hour guard-gated community. Just beyond the gates, the vibrant charm of Siesta Key Village awaits with its locally loved restaurants, boutiques, and island nightlife, while downtown Sarasota’s renowned arts and cultural scene is only a short drive away. This is more than a residence — it is an opportunity to experience the best of beachfront living on Siesta Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Natalie Gutwein (941-993-2660)
156 SIESTA DR, SARASOTA, FL 34242
$1,649,000350 Days on yellowkey MLS ID: A4661717
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2901 Built: 1977 Tax: $19,016 (2024)Community: Siesta Rev ResubSingle Family
Taxes:$19,016
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best of upscale coastal living with impressive rental performance. Designed to host gatherings of all sizes, it is perfectly suited as a primary residence, vacation escape, or income-producing property. In 2024, it brought in $132,419 in gross rental income, with 2025 projections at $120,681, showcasing its strong investment appeal. Just a short stroll to Shell Beach and minutes from Siesta Key Village and the world-renowned Siesta Key Beach, the home offers unmatched access to award-winning white sand, vibrant dining, and boutique shopping. A complete renovation in 2019 transformed the property with a new metal roof, hurricane-impact windows, patio and garage doors, upgraded AC systems, and an oversized resurfaced lap pool with all-new equipment, including a heat pump. Over 50 Areca palms frame the lush tropical landscaping, providing beauty and privacy while remaining easy to maintain. The outdoor living space rivals a private resort, featuring a sparkling pool, spacious patio, and tranquil surroundings ideal for lounging or entertaining. Inside, natural light fills the open floor plan, creating seamless flow to the outdoor areas and making it a true entertainer’s haven. Impeccably maintained and move-in ready, this Bay Isle residence offers a rare opportunity to enjoy the island lifestyle while benefiting from consistent rental income.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
5830 MIDNIGHT PASS RD #48, SARASOTA, FL 34242
$558,00060 Days on yellowkey MLS ID: A4695273
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1963 Tax: $3,659 (2025)Community: Jamaica RoyaleCondo
Taxes:$3,659
Remarks: Welcome to your own slice of paradise at Jamaica Royale, located directly on the world-famous shores of Siesta Key Beach. This beautifully remodeled one-bedroom, one-bath condominium, complete with a queen sleeper sofa, and a twin sleeper sofa, offers the perfect combination of coastal sophistication and exceptional rental income potential. Thoughtfully updated throughout, the stunning kitchen features elegant quartz countertops, custom wood cabinetry, stainless steel appliances, and a convenient laundry closet with a stackable washer and dryer—ideal for effortless beachside living and entertaining. The spa-inspired bathroom showcases designer finishes, including a custom-tiled shower and sleek quartz top vanity. Designed with both comfort and style in mind, the open and inviting floor plan is offered fully furnished and turnkey, allowing you to begin enjoying the Siesta Key lifestyle immediately. Whether you're seeking a personal beachfront getaway, an investment property, or both, this residence delivers. Jamaica Royale is one of Siesta Key's most sought-after beachfront communities, offering flexible one-week minimum rentals, making it highly attractive to vacationers and investors alike. Residents and guests enjoy 3 heated community pools, designated BBQ areas, a shuffleboard court and approximately 300 feet of private beachfront, with direct access to the Gulf of Mexico's crystal-clear waters and powder-soft quartz sand. Perfectly positioned just minutes from Siesta Key Village, you'll enjoy easy access to award-winning restaurants, charming boutiques, entertainment, and vibrant nightlife. This is a rare opportunity to own a turnkey beachfront retreat in one of Florida's most desirable coastal destinations—where every day feels like a vacation.
Listing is courtesy of: PEPPERTREE BAY REALTY INC (941-914-3380)
Listing Agent: Eliza Miller (941-914-3380)
5600 BEACH WAY DR #201, SARASOTA, FL 34242
$575,000421 Days on yellowkey MLS ID: A4654536
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1259 Built: 1970Monthly Fee: $1,467 Tax: $5,918 (2024)Community: Beachway AptsSpa: NoCondo
Taxes:$5,918
Remarks: SELLER SAYS BRING ALL OFFERS! MAJOR PRICE IMPROVEMENT!! Reduced over 75k! Have you ever wondered what it's like to own a Siesta Key sunset? Throw on your swimsuit, grab a towel and take a short stroll across the street, because here at Beach Way, you can't get much closer! Embrace your very own next-level Florida lifestyle with this exceptional opportunity. This second floor 2-bedroom, 2-bathroom condo is ideally situated and directly across the street from the world-renowned Siesta Key Beach, continuously celebrated for its powdery soft, white quartz sands and clear waters. This property is being offered fully furnished and is move in ready, presenting a unique chance to personalize your very own dream retreat whether as a permanent residence or a vacation getaway. This unit beams with natural light throughout, showcasing its rare beauty. With a minimum lease period of one month, up to twelve times a year, it also offers potential for rental income. Rental Proforma attached. As you enter the front doors to this beach oasis, prepare to be impressed by an open-concept kitchen that seamlessly flows into the living and dining areas, extending out to a private screened-in lanai where you can take in partial glimpses of the Gulf, creating a perfect setting for relaxation and entertaining. Need a little space? Both bedrooms feature walk-in closets, providing ample storage and comfort. In addition, the unit overlooks the community's heated pool which is maintained at 85 degrees year-round. This well-maintained community was built in 1970, offering a host of amenities designed for convenience and leisure. Residents have access to a community room with a full kitchen for social gatherings, picnic and grilling areas, elevators, laundry facilities on each floor, and a personal storage unit. In addition, your deeded carport is located just steps from your front door, ensuring ease of access. Recent updates to building include a new roof in 2020, an updated elevator installed in 2019, re-plumbed stacks completed in 2018, the addition of new vinyl fencing in 2021. The quarterly condo association fee covers access to all the amenities, pest control, basic cable, water/sewer services, grounds maintenance, weekend on-site maintenance, and community insurance. Living on Siesta Key means more than just proximity to the beach; it's about embracing a lifestyle where every day feels like a vacation. Start your mornings with a peaceful walk along the shoreline, enjoy paddleboarding in the calm Gulf waters, or partake in beach yoga sessions at sunrise and drum circle Sundays. The island's laid-back atmosphere is complemented by its vibrant community, offering a mix of friendly full-time residents and seasonal visitors. Ready to venture out for some more fun? Siesta Key Village, just a short distance away, is the heart of the island's social scene. Here, you'll find an array of casual bars, eateries, and boutiques, perfect for evening outings or weekend brunches. The community's eclectic vibe ensures there's always something happening, from local festivals to live music events. Other close by attractions include the Ringling Bridge, Downtown Sarasota and St. Armands, close proximity to top rated schools and hospitals, SRQ Airport and University Town Center. Don't let another Season pass you by from owning your own slice of paradise in the sand. Schedule your showing today.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Ashley Nevadomski (941-769-7627)
9200 MIDNIGHT PASS RD #25, SARASOTA, FL 34242
$429,00086 Days on yellowkey MLS ID: A4692488
REDUCED by $20,000 (4.5%) on 05/26/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 906 Built: 1972 Tax: $4,028 (2025)Community: Inlet AptsCondo
Taxes:$4,028
Remarks: Introducing Inlet Apartments - Siesta Key, a charming, quaint coastal retreat for a tropical vacation or a beach getaway. This second-floor, one-bedroom, one-bath is quiet and peaceful on the Blind Pass Lagoon at far south end of Siesta Key and just beyond your sliding glass doors. You will be instantly captivated by views of paddleboarders and kayaks going by, plus a heated swimming pool and a partial view of the Gulf. With 906 square feet, this residence is sold turnkey furnished, blending modern sophistication with relaxed coastal living. Contemporary new kitchen with new appliances, white quartz countertops, an oversized island, and crafted for effortless everyday living. The open-concept layout flows through the dining room, with a queen-size Murphy bed for extra guests, and living spaces, enhanced by luxury vinyl wood flooring and modern compact ceiling fans that adjust with touch of a button. Wake up to enchanting lagoon views in the tranquil primary suite, and beautifully updated bath. Go outside to a spectacular 200-square-foot screened lanai with pull-down shades for privacy, ideal for morning espresso, sunset cocktails or simply soaking in Siesta Key’s year-round beauty. There are convenient elevators, laundry facilities and assigned parking for each unit. HVAC in 2021, water heater in 2022. Life at Inlet boating amenities included private boat dockage for sailboats and powerboats up to 26 feet (first-come, first-serve basis). The Blind Pass Lagoon leads into Sarasota Bay and onto the Gulf. There are fishing, kayak storage and launch, waterfront pool, all just minutes from Turtle Beach and a short trolley ride to Crescent Key Village. This is more than a condominium at the beach, it’s a one-of-kind opportunity to own a piece of Siesta Key.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Lisa Gullick (941-364-4000)
1328 SIESTA BAYSIDE DR #1328C, SARASOTA, FL 34242
$714,000257 Days on yellowkey MLS ID: A4672183
REDUCED by $20,000 (2.7%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1280 Built: 1988 Tax: $7,699 (2024)Community: Gulf & Bay Club BaysideCondo
Taxes:$7,699
Remarks: Welcome to Gulf & Bay Club Bayside, one of Siesta Key’s most desirable resort-style communities. This turnkey-furnished residence offers the perfect blend of coastal comfort, modern updates, and access to Siesta Key’s world-famous beaches. Designed with a bright, open layout and porcelain tile flooring throughout, the interior feels fresh and inviting from the moment you step inside. Oversized windows and glass sliders fill the home with natural light and extend the living space to the screen-protected lanai, creating an ideal spot to relax after a day at the beach. The updated kitchen features stone countertops, contemporary cabinetry, quality appliances, and generous storage. The dining and living spaces connect effortlessly, giving the residence a comfortable flow for both everyday living and seasonal enjoyment. Both bedrooms provide privacy for owners and guests, and the primary suite features a walk-in closet, en-suite bath, and direct access to the lanai. A second bedroom serves well as a guest room, home office, or multi-use space. Gulf & Bay Club Bayside is known for its beautiful coastal architecture and outstanding amenities. Residents enjoy two heated swimming pools, tennis courts, pickleball, a well-equipped fitness center, grilling stations, a fishing dock on the Intracoastal Waterway, and a stylish clubhouse. The community’s deeded walking beach access—located directly across the street—places you moments from Siesta Beach’s unique shores and turquoise water, making it effortless to enjoy sunrise or sunset strolls, and spontaneous beach days. Situated in the heart of Siesta Key, the location offers quick access to the island’s best attractions. Explore nearby Siesta Village, known for its open-air restaurants, boutique shops, live music, and laid-back coastal atmosphere. Boaters will appreciate the proximity to the Intracoastal Waterway, marinas, and local rental options. For even more dining, arts, and entertainment, vibrant downtown Sarasota is just a short drive away—home to the Sarasota Opera House, Van Wezel Performing Arts Hall, Selby Gardens, the Ringling Museum, St. Armands Circle, and an ever-growing culinary scene. Whether you’re seeking a full-time residence, a seasonal getaway, or an investment opportunity with weekly rentals permitted, this Gulf & Bay Club Bayside property delivers the ideal combination of location, lifestyle, and value on Siesta Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
4822 OCEAN BLVD #3D, SARASOTA, FL 34242
$825,00070 Days on yellowkey MLS ID: O6406435
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1440 Built: 1973Monthly Fee: $1,667 Tax: $3,838 (2025)Community: Siesta TowersSpa: NoCondo
Taxes:$3,838
Middle School: Booker Middle
Remarks: This condominium at Siesta Towers offers two master suites. Welcome to this extraordinary living experience and location where every day you can enjoy the gulf views and the palm trees dotting the horizon. Swim and relax in the heated outdoor pool that sits right on the waterfront. Enjoy a drink on the cocktail pier while you watch the dolphins swim or bask in the glowing light of the stunning sunsets. Includes gym, fishing pier, BBQ, club house, and bike storage. Located on Siesta Key on the water, close to public beach access and Siesta Key Village. Many local beaches, parks, nature preserves, and bird sanctuary's close by. This turnkey fully furnished condo offers serene personal space, ample storage, walk in closet, lots of natural light, brand-new hurricane doors, eat in kitchen, dining room, living room, and office area. Designated parking space.
Listing is courtesy of: HOUWZER INC (267-765-2080)
Listing Agent: Daniel Robinson (904-447-8922)
7366 POINT OF ROCKS RD, SARASOTA, FL 34242
$26,000,000203 Days on yellowkey MLS ID: A4673754
Bed: 5 Bath: 6.0 Gar: 6 Liv Area Sq Ft: 10600 Built: 2020 Tax: $115,958 (2025)Community: Siesta KeySpa: YesSingle Family
Taxes:$115,958
Remarks: Rising above an enviable stretch of shoreline, this Gulf-front estate showcases timeless architecture and coastal refinement. Designed by CMSA Architects and completed in 2020, the residence features layered rooflines, sculpted stone staircases, and soaring arched windows across more than 180 feet of Gulf frontage. With 10,600 square feet of interiors and 20,982 square feet in total, the home offers a grand yet effortless indoor–outdoor lifestyle, ideal for both elevated entertaining and daily living. A sweeping motor court, mature palms, and a grand double staircase create an immediate sense of arrival. Inside, natural light and uninterrupted Gulf vistas establish a feeling of calm, scale, and sophistication from sunrise to sunset. The great room, lined with floor-to-ceiling arched windows and anchored by a carved-stone fireplace, delivers both serenity and architectural presence. The main kitchen is a triumph of craftsmanship - featuring custom Campbell cabinetry, quartz countertops, designer lighting, Sub-Zero refrigeration, a Wolf six-burner dual-oven range, and a substantial island that anchors the open flow into the living and dining spaces. A prep kitchen and workspace elevate functionality with premium appliances, expansive storage, quartz counters, and a dedicated gift-wrapping wall. The bar and wine room create a refined entertaining destination, defined by custom cabinetry and designer lighting. An iron-and-glass–enclosed, temperature-controlled wine room serves as the focal point, complemented by adjacent illuminated display shelving. Sub-Zero refrigeration, an ice maker, and a Fisher & Paykel dishwasher drawer complete the space. Outdoors, the estate unfolds across three dramatic tiers of Gulf-facing living, featuring arched loggias and a resort-style alfresco kitchen with a wraparound bar that opens seamlessly to the main living spaces. An elevated infinity-edge pool and spa appear to merge with the Gulf, while thoughtfully designed outdoor areas transition effortlessly to a manicured lawn and direct access to the crystal-clear waters at Point of Rocks—where snorkeling, dolphin sightings, and sunset walks become part of daily life. The primary suite forms a private wing, introduced by an illuminated groin-vault corridor that enhances the home’s architectural rhythm. Gulf views fill the bedroom and its terrace, while the bath offers a symmetrically designed retreat with dual vanities, full-height mirrors, multiple chandeliers, a massive double-entry shower, a stone-surround soaking tub, a Sub-Zero–equipped coffee bar, and two exceptional custom closets. Nearby, the office provides a quiet, light-filled workspace. The upper level is devoted to comfort and privacy, offering four well-appointed guest suites, a spacious family room with a wet bar, multiple terraces capturing Gulf views, an additional office, and a laundry room. The ground level is enhanced by indoor–outdoor walkways connecting multiple spaces and generous storage, reinforcing the effortless, resort-style livability. A generator, 3-stop elevator, 6-plus humidity-controlled garage spaces, floor-to-ceiling shades, linear vents, whole-house automation, and shellstone and French oak flooring complete the offering. A short, shaded, tree-lined walk places you at Siesta Key Beach, the No. 1 beach in America by TripAdvisor, offering effortless access to one of the world’s most iconic shorelines.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
915 SEASIDE DR #402, Weeks 10-13, SARASOTA, FL 34242
$100,00065 Days on yellowkey MLS ID: A4694774
Bed: 2 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1750 Built: 2009 Tax: $428 (2026)Community: Siesta Key Beach ResidencesSpa: YesCondo
Taxes:$428
Tax Year: 2026
Remarks: Fractional Ownership. Unique opportunity to own four consecutive weeks in March on Siesta Key Beach. Experience luxury beachfront living with this Winter Fractional Package, offering a 1/8th ownership share at The Residences on Siesta Key Beach. This rare offering provides the opportunity to own a piece of paradise on one of America’s most celebrated beaches while enjoying the comfort, convenience, and elevated service of a luxury resort. This expansive residence features a primary suite, a junior suite and beautifully updated custom furnishings valued at more than $150,000. The fully equipped kitchen is appointed with premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtful details throughout. Owners enjoy the legendary hospitality and services of Hyatt Vacation Club, including daily complimentary continental breakfast, beach service, recreation and front desk staff, assistance with local activities, valet parking, and 24-hour security. Enjoy the best of Siesta Key beachfront living with resort-style amenities, full-service convenience, and luxury condominium ownership, all at a fraction of the cost.
Listing Agent: Kelly Mooney (941-587-8430)
137 AVENIDA MESSINA #1, SARASOTA, FL 34242
$600,000258 Days on yellowkey MLS ID: A4671658
REDUCED by $20,000 (3.2%) on 05/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1966 Tax: $6,247 (2024)Community: Villa NavarraCondo
Taxes:$6,247
Remarks: Centrally located and fully furnished! Located within the boutique condominium community of Villa Navarra on Siesta Key, this fully updated, turnkey-furnished ground-floor residence offers an exceptional blend of quality, comfort, and convenience. The property is ideally situated one block from Siesta Key Village and approximately two blocks from Siesta Beach, providing easy access to the island’s most popular destinations. Ideal for full time, snow birds or people looking to lease this condo out to renter's for the two month minimum. The residence features two bedrooms and two full bathrooms arranged in an open, functional layout. The spacious living and dining areas flow seamlessly into a thoughtfully renovated kitchen appointed with solid-surface countertops, modern cabinetry, and stainless-steel appliances. Finishes and flooring throughout the home have been carefully selected to create a clean, contemporary aesthetic that complements its coastal setting. The primary suite includes an en-suite bath and generous closet space, while the guest bedroom is conveniently located near the second full bath. The ground-floor design allows direct access to the assigned parking space for added ease. With extensive updates and attention to detail, this residence is move-in ready and designed for practical, comfortable living. Villa Navarra is a well-maintained, low maintenance community of just sixteen units surrounded by tropical landscaping and a relaxed island atmosphere. Residents enjoy convenient access to the free Siesta Key trolley and can easily walk to Siesta Key Village, offering a wide variety of local dining, shopping, and entertainment options. The renowned quartz sands and turquoise waters of Siesta Beach are only a short stroll away. This property is well-suited for a full-time residence, seasonal getaway, or long-term rental investment. Its location, quality, and turnkey condition make it a rare opportunity to enjoy the Siesta Key lifestyle within a private and beautifully maintained setting.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jeffrey Bray, Pllc (941-718-1213)
915 SEASIDE DR #312, Weeks 16-17, SARASOTA, FL 34242
$48,00087 Days on yellowkey MLS ID: A4692319
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1750 Built: 2009 Tax: $321 (2026)Community: Siesta Key Beach ResidencesSpa: YesCondo
Taxes:$321
Remarks: Fractional Ownership. Experience luxury beachfront living with this Winter Fractional Package offering a 1/16th share of ownership at The Residences on Siesta Key Beach. This is a rare opportunity to own a piece of paradise on one of America’s top-rated beaches while enjoying the comfort, convenience, and services of a luxury resort. This expansive residence features a primary suite, junior primary suite, and guest bedroom, along with beautifully updated custom furnishings valued at more than $150,000. The fully equipped kitchen includes premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtful details throughout. Owners enjoy legendary Hyatt Vacation Club hospitality services, including daily complimentary continental breakfast, beach service, recreation and front desk staff, assistance with local activities, valet parking, and 24-hour security. Enjoy everything you would expect from a luxury Siesta Key beachfront condominium with resort-style amenities and services, all at a fraction of the cost.
116 VISTA HERMOSA CIR #204C, SARASOTA, FL 34242
$575,00069 Days on yellowkey MLS ID: A4693969
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1971 Tax: $4,243 (2025)Community: Vista HermosaCondo
Taxes:$4,243
High School: Riverview High
Remarks: Welcome to Vista Hermosa! Full remodeled, 2-bedroom, 2-bathroom condo located directly across the street from the world-renowned Crescent Beach on Siesta Key. This second-floor unit (with elevator access) showcases an extensive list of high-end upgrades and thoughtful renovations that make it stand out above the rest. Step inside to find an impact-rated thermal glass door, porcelain tile in the bathrooms, fresh paint, flat ceilings, LED lighting, and luxury waterproof vinyl flooring throughout. The kitchen has been completely redesigned with solid wood, soft-close cabinetry, quartz countertops, a recessed black sink, designer switch plates, and a coordinated Samsung stainless steel appliance package. A center island with drawers offers added prep space and storage, while the commercial hood above the stove, sleek under-cabinet lighting, and modern fixtures complete the contemporary look. Both bathrooms have been remodeled with tiled showers, new vanities, updated fixtures, new Panasonic fans, and a Kohler toilet. Other improvements include new baseboards, upgraded outlets, partial new ductwork, a newer HVAC system , and three impact-rated windows. The bedrooms also feature elegant crown molding, adding a refined touch to these relaxing retreats. This condo makes for an ideal Siesta Key beach home with incredible accessibility to everything you could want including popular shops, restaurants, and the white sand shoreline just steps away. It’s also a fantastic investment opportunity, offering a worry-free experience with no storm damage, on-site management, and covered parking. Enjoy peace of mind, style, and a walkable coastal lifestyle in this beautifully finished condo in one of Siesta Key’s most desirable communities.
Listing Agent: Dawn Bear (941-468-7224)
643 CALLE DE PERU, SARASOTA, FL 34242
$1,996,000362 Days on yellowkey MLS ID: A4658846
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 1982 Built: 1980 Tax: $8,733 (2024)Community: Sarasota BeachSingle Family
Taxes:$8,733
Remarks: Pre-construction. To be built. Custom beach home opportunity! Less than a mile to the #1 Rated Beach in the Nation- Siesta Beach! Almost 1/4 acre lot in a charming neighborhood with close proximity to public beach and Village. The existing structure is a tear down, leaving a beautiful canvas to create your dream home or investment property! Optional Island Series plans by Yoder Custom Homes are available, or choose the builder of your choice, or land only. Just 6.4 mi to downtown Sarasota- known for it's Arts & Culture. Call today for more information! Land only listed in vacant land.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Rachelle Tirey (941-301-9187)
84 AVENIDA VENECCIA #202 & 203, SARASOTA, FL 34242
$7,950,000824 Days on yellowkey MLS ID: A4608628
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6206 Built: 2024Monthly Fee: $6,619 Tax: $72,971 (2024)Community: 89 BeachCondo
Taxes:$72,971
Remarks: One or more photo(s) has been virtually staged. Experience luxury living at its finest in this breathtaking one-of-a-kind new construction condominium nestled directly on the pristine shores of world famous Siesta Beach. Spanning over 6200 square feet, this exclusive residence offers unparalleled opulence and panoramic views of the azure waters and fiery sunsets. Elegance meets convenience with a private elevator whisking you to your sanctuary above. Park your collection of vehicles effortlessly in the expansive 4-car garage before ascending to your private oasis. Step out onto expansive covered balconies to savor the sea breeze and soak in the mesmerizing vistas. Entertain with flair in the rooftop pool area, complete with a firepit for cozy gatherings under the stars. Your own private beach cabana beckons for tranquil moments by the water's edge, while the gated entrance ensures utmost privacy and security. Indulge in the ultimate relaxation within the heart of Siesta Village, where world-class dining and boutique shopping await a mere two blocks away. Retreat to the comfort of your home office or unwind in the bonus/game room after hosting guests in one of the three en suite guest bedrooms, each offering unparalleled comfort and privacy. Luxuriate in the gulf-front master suite, adorned with ceiling-to-floor windows framing the endless ocean vistas. This is a rare opportunity to own a slice of paradise on iconic Siesta Key, where every amenity and indulgence awaits at your doorstep.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Tom Cail, Pa (941-780-2245)
8911 MIDNIGHT PASS RD #208, SARASOTA, FL 34242
$595,000202 Days on yellowkey MLS ID: A4677015
REDUCED by $40,000 (6.3%) on 05/20/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1415 Built: 1973 Tax: $6,230 (2025)Community: Sunrise Cove Sec 2Condo
Taxes:$6,230
Remarks: Welcome to Sunrise Cove and the coveted and quiet south end of Siesta Key. This DIRECT BAYFRONT condo is a 3 BEDROOM CONDO and is directly across the road from TURTLE BEACH with plenty of PUBLIC BEACH ACCESS. This condo unit was re-configured and now has three full bedrooms and two full bathrooms. Features include new interior paint, opened and central kitchen, split bedroom floor plan, washer/dryer inside unit, and it comes completely furnished. The open kitchen features a solid beadboard cabinetry, pantry, and plenty of storage. This is an end unit with end unit windows in two of the bedrooms for added light. Relax and look directly out onto Little Sarasota Bay and enjoy wildlife, dolphins, and manatees as well as beautiful sunrises! This condo is super clean and ready to go! There is a storage closet down the hall for beach items and monthly rentals are allowed plus one brand-new carport is included! SUNRISE COVE features 49 boat slips with vacancies, two heated swimming pools, pickleball, tennis, clubhouse with clubroom, fitness room, billiards/ping pong, kayak storage, BBQ grill with gazebo, and public beach access directly across the street! This is a super well-run and manicured complex and is very near to two delicious restaurants. This south end of Siesta Key is very quiet. Come see this beautiful beach and waterfront condo today!
Listing Agent: Joe Cleary (941-650-8485)
4857 PRIMROSE PATH, SARASOTA, FL 34242
$4,795,00071 Days on yellowkey MLS ID: A4693435
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3935 Built: 2026 Tax: $12,753 (2025)Community: Harmony SubSpa: YesSingle Family
Taxes:$12,753
Remarks: Pre-Construction. To be built. New construction waterfront residence on Siesta Key featuring warm modern coastal architecture, clean lines, and natural materials thoughtfully curated throughout. Located at 4857 Primrose Path, this canal-front home offers approximately 3,935 square feet of air-conditioned living space with 4 bedrooms, expansive indoor-outdoor entertaining spaces, and a private courtyard-style pool design centered around privacy, natural light, and seamless connection to the outdoors. Thoughtfully designed to maximize natural light and spatial flow, the residence features large walls of glass, covered lanais, and multiple rooms overlooking the pool and waterfront. Stone accents, warm wood detailing, and refined architectural finishes create an inviting atmosphere while maintaining a clean contemporary aesthetic. The kitchen serves as the centerpiece of the home with custom cabinetry, an oversized waterfall island, premium appliances, designer surfaces, and a concealed prep pantry providing additional functionality and storage. Positioned on a canal-front homesite in one of Siesta Key’s most desirable neighborhoods, the property offers convenient boating access along with close proximity to Siesta Beach, Siesta Key Village, and downtown Sarasota dining and entertainment. Additional features include: • Approximately 4,300 square feet under roof • Elevated construction designed to current Florida wind and flood standards • Resort-inspired courtyard pool and outdoor entertaining spaces • Large covered terraces and second-floor balcony areas • Custom landscaping and curated architectural detailing throughout • Oversized glass openings designed to maximize natural light • Two-story floor plan with private guest accommodations A thoughtfully designed new construction residence combining refined architecture, quality materials, and waterfront living in one of Siesta Key’s most sought-after locations. Estimated completion: Winter 2026. For additional renderings, floor plans, and project details, visit: 4857PrimrosePath dotc0m
Listing Agent: Carolyn Lobue (847-400-7357)
8710 MIDNIGHT PASS RD #405, SARASOTA, FL 34242
$684,800289 Days on yellowkey MLS ID: A4667487
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1012 Built: 1980 Tax: $8,127 (2024)Community: TortugaCondo
Taxes:$8,127
Remarks: Looking for a beach front condo on Siesta Key? Wait until you see Tortuga condominium complex. This private gated community is the slice of paradise you have been looking for. Amenities include heated community indoor/outdoor pool, sauna. The clubhouse has been renovated and, with its full kitchen and dining area, can be reserved for a private gathering! This 2 bedroom, 2 bath condo is updated throughout with hurricane sliding doors and is being sold turn-key furnished! You have a water view of the Gulf. The best part of this condo is that it is rented December 28, 2025 through March 2026! Tortuga amenities extend to the Bay side also!! Included are boat docks, a fishing pier, tennis and pickleball courts. Tortuga assigned boat slips are 10.5ft wide by 30ft long. So, length including bow anchor platform, swimming platform, engine mount, protruding propeller, or any other extensions cannot exceed 30ft. HOA fees include basic cable and internet, water, trash pickup and an onsite maintenance manager. Whether you envision it as your permanent sunny abode, a splendid second home, or a savvy investment, your own piece of paradise awaits!
Listing is courtesy of: DELUCA REALTY INC (941-487-7162)
Listing Agent: Anthony Deluca (941-685-6001)
915 SEASIDE DR #412, SARASOTA, FL 34242
$1,799,000170 Days on yellowkey MLS ID: A4681675
REDUCED by $200,000 (10.0%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1750 Built: 2009 Tax: $16,278 (2025)Community: Siesta Key Beach Residences IiSpa: YesCondo
Taxes:$16,278
Remarks: Welcome to a premier Siesta Key Beach condo that delivers the ultimate combination of luxury coastal living and high-performing rental income potential. This beautifully updated 3-bedroom, 2-bath condominium is professionally managed through an established onsite program, offering owners a seamless, turnkey experience with the ability to enjoy the home personally while also participating in a proven, income-producing rental program. Located directly on world-famous Siesta Key Beach, consistently ranked among the top beaches in Florida, the U.S., and the world, this property benefits from strong year-round demand for high-end vacation rentals. Whether you’re looking for a beachfront vacation home, a short-term rental investment, or the ideal blend of both, this residence is positioned to deliver outstanding lifestyle value and long-term upside. The current owner has successfully utilized the rental program while still enjoying substantial personal use, making this an exceptional opportunity for buyers seeking a condo with documented rental history and the flexibility to reserve premium seasonal time for themselves. Inside, the condo features a bright, open layout with spacious living areas and finishes that appeal to both owners and guests. Enjoy partial Gulf of Mexico views and Siesta Key Beach scenery from the primary suite, living room, and private lanai—capturing the coastal lifestyle today’s vacation renters are looking for. Owners and guests enjoy access to desirable resort-style amenities, including a sparkling pool, fitness center, concierge services, and professional onsite management. With unbeatable beach access, nearby attractions, and a consistent track record of rental demand, this is one of the most compelling income-producing condos on Siesta Key. Schedule your private showing today and discover the value of owning a luxury Siesta Key vacation rental property.
8750 MIDNIGHT PASS RD #302, SARASOTA, FL 34242
$429,000177 Days on yellowkey MLS ID: A4680093
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 800 Built: 1980 Tax: $4,916 (2025)Community: TortugaCondo
Taxes:$4,916
Remarks: Come live the dream in this great "fully furnished" residence on the south end of Siesta Key. Share amenities with Turtle Bay across the street like tennis, pickleball, and boat slips. Directly on the gulf, enjoy beach and sun year round. Secure, under building covered parking. Washer/dryer combo in unit! This unit is clean and in fabulous condition and comes fully furnished. Situated at the southern end of Siesta Key, it offers a more remote feel. Take the trolley into the village for dinner and shopping. This unit shows excellent and is priced right!
Listing is courtesy of: HOUSEMAX REALTY LLC (941-315-1990)
Listing Agent: Paul Defelice (941-315-1990)
527 BEACH RD, SARASOTA, FL 34242
$3,195,000159 Days on yellowkey MLS ID: O6384340
INCREASED by $220,000 (7.4%) on 05/15/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1803 Built: 1985 Tax: $18,981 (2025)Community: Sarasota BeachApartment
Taxes:$18,981
Remarks: Discover an exceptional income-generating property in the heart of coveted Siesta Key right on Beach Road! This fully renovated raised multi-unit compound features a spacious 2-bedroom, 2-bathroom unit and a 2-bedroom, 1-bathrooom unit (side by side). An impressive gross income in 2023 and n 2024 (despite hurricane-related downtime), this turnkey investment provides immediate cash flow. Note: This property is zoned an RMF (Residential Multifamily) and is legally able to accept nightly rentals. The property boasts recent upgrades including new AC (2022), updated flooring (2025), modernized plumbing (2022), electrical (2022), and hot tubs (2022). This amazing opportunity is the best cap rate on any house on Siesta Key. Whether you're seeking a high-performing Airbnb rental portfolio or a strategic redevelopment opportunity in one of Florida's most desirable beach destinations, this property delivers both immediate income and long-term appreciation potential. Absentee owner managed; turnkey operation available at on a management fee with all staff staying in place. This house already has engineering drawings to enclose the bottom area adding 2,000 additonal square foot, that would increase rent by or more. This property could be purchased as a portfolio with 5228 Calle Menorca and 6550 Sabal Road.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
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