Location: Sarasota , 34242
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1055 W PEPPERTREE DR #102AA, SARASOTA, FL 34242
$850,000151 Days on yellowkey MLS ID: A4677695
1 Days Off yellowkey (back on 5/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1163 Built: 1974 Tax: $4,365 (2025)Community: Peppertree Bay IvSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,365
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. Rare opportunity to own one of the most resilient and desirable residences on Siesta Key! This 2-bedroom, 2-bath condominium offers 1,163 square feet of living space (1,462 gross square feet) and is ideally positioned on the west side of the building on an elevated first floor, approximately 15 feet above sea level. It is also the closest high-rise condominium to the beach, offering exceptional proximity to the Gulf. One of only six residences in the building with an expansive deck, this sought-after middle-unit location provides a truly rare outdoor living experience. The oversized deck offers ample space for dining, entertaining, or simply relaxing while enjoying coastal breezes and sunsets. The residence has demonstrated remarkable storm resilience, sustaining no damage through three major hurricanes. This is attributed to its elevated positioning, protected west-side exposure, and six hurricane-rated doors installed in 2021. Recent interior upgrades enhance both style and comfort, including luxury vinyl flooring and freshly painted walls completed in 2025. The refrigerator, washer, dryer, and garbage disposal were also replaced in 2025. A dedicated parking space conveys with the unit. Owned by the same family since 1976, the home reflects decades of pride of ownership and thoughtful care. The community features two pools and two clubhouses on both the Gulfside and Bayside, along with a Gulfside fitness center. A well-managed rental program offers flexibility for owners while preserving a relaxed residential atmosphere. Located in one of Florida’s most coveted coastal settings, this exceptional residence offers a rare blend of scarcity, storm resilience, expansive outdoor living, and resort-style amenities—making it an outstanding lifestyle choice and investment opportunity.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Tanya Stutzman (941-504-8785)
1215 S PORTOFINO DR #406, SARASOTA, FL 34242
$435,00032 Days on yellowkey MLS ID: A4691798
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1968 Tax: $4,559 (2025)Community: Siesta Harbor ICondo
Taxes:$4,559
Elementary School: None
High School: None
Middle School: None
Remarks: Escape the winter chill and step into your endless summer at this meticulously maintained, fully turn-key furnished 2-bedroom, 2-bathroom condo in the desirable Siesta Harbor community on Siesta Key. This 4th-floor gem has been lovingly cared for by the owners and offers charming peek-a-boo ocean views along with direct canal frontage — perfect for morning coffee with a waterfront breeze or romantic sunset dinner. This active 55+ community delivers the true Siesta Key lifestyle with outstanding amenities: deeded beach access via Crescent Arms, a fishing pier on the Intracoastal Waterway, a heated community pool, boat docks, onsite management, and a vibrant calendar of social activities. You’re just minutes from downtown Sarasota’s top restaurants, shops, and cultural attractions.Enjoy low HOA fees, worry-free maintenance, and peace of mind knowing the property has sustained no storm damage. This turn-key condo is your opportunity to own a slice of the laid-back tropical dream on Siesta Key.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-556-2150)
Listing Agent: Miao Whiteside (941-263-9898)
5740 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,950,00057 Days on yellowkey MLS ID: A4686166
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $12,418 (2025)Community: Gulf & Bay Club Ph 6Spa: YesCondo
Taxes:$12,418
Remarks: A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Drew Jacobsen (941-253-6309)
5880 MIDNIGHT PASS RD #306, SARASOTA, FL 34242
$1,285,000265 Days on yellowkey MLS ID: A4665591
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $8,594 (2025)Community: CasarinaCondo
Taxes:$8,594
Remarks: Welcome to Your Siesta Key Sanctuary. Step into paradise with this turnkey furnished condo in the highly sought-after Casarina complex, offering 200 feet of private beach access on the world-renowned Crescent Beach. Nestled on a lush 7-acre property, Casarina features beautifully landscaped gardens, tennis and pickleball courts, a beachside pool and spa, an elevated beach deck, and a welcoming clubhouse—all just steps from the famous crystal sands of Siesta Key Beach. Located on the third floor, this residence boasts a newly updated kitchen, luxury vinyl flooring, an updated guest bath, and a new AC unit. Enjoy serene garden views from your 17-foot screened balcony, with a peek-a-boo view of the Gulf and pool areas. Need extra space? The flexible 8’ x 8’ breakfast nook can easily be transformed into a home office or additional sleeping area. Casarina is a well-maintained 89-unit complex with fully funded reserves and recent complex renovations. Owners can bring one small pet, and enjoy the convenience of a covered carport and access to the free Siesta Key Trolley for dining, shopping, and entertainment. Whether you're paddle boarding, kayaking, biking, or simply relaxing on the beach, this condo offers the perfect blend of island lifestyle and resort-style amenities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
8779 MIDNIGHT PASS RD #401H, SARASOTA, FL 34242
$595,000309 Days on yellowkey MLS ID: A4661131
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1485 Built: 1980 Tax: $4,969 (2025)Community: Island Reef Ii Ph 1 2 & 3Spa: NoCondo
Taxes:$4,969
Remarks: ENJOY THE BAY VIEWS FROM THIS UPDATED HOME! Kitchen with Granite countertop, Laundry in Residence, office space off foyer. Partially Furnished! Carport! Island Reef is a serene waterfront community, one of the few Gulf to Bay community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed) two lit tennis courts, pickleball, 2 fitness rooms, Kayak Storage, Library, Billiards, game room, clubhouse, two heated pools and Gas Grills, PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key’s popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cut brunch spots and dancing and live music every night of the week!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Marlene Marshall (941-539-8850)
8710 MIDNIGHT PASS RD #203B, SARASOTA, FL 34242
$699,00073 Days on yellowkey MLS ID: A4688439
REDUCED by $36,000 (4.9%) on 05/05/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1650 Built: 1980 Tax: $8,179 (2025)Community: Tortuga Beach ClubSpa: YesCondo
Taxes:$8,179
Remarks: Perfect Beach Life on Siesta Key! Tortuga Beach has so much to offer. Private 77 unit complex has the small intimate feel with a luxury with it's many offerings. Private Beachfront, Tennis, Clubhouse with kitchen, library and entertainment area, indoor/outdoor community pool, sauna, sun deck with grills and seating, and boat slips across the street on the bay. There are 3 slips open for rental for $300 a year. Just fill out your application. With the friendly residents you can enjoy the relaxing atmosphere with the wonderful views of the Gulf of Mexico from daytime sunbathing to sunset pleasures. Upon arrival to the condo you will find an enclosed lanai to offer more living space in the 1650 Square feet. Kitchen has plenty of space with it's wood cabinets and granite countertops with pass through breakfast bar. New AC. Split Floor plan. Primary bedroom closet contains the washer dryer but Tortuga also offers a laundry facility if you are in need. Separate dining room just off the kitchen for entertainment. Covered Parking spot very close to the entrance and elevator for easy loading and unloading.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
6480 MIDNIGHT PASS RD #503, SARASOTA, FL 34242
$1,199,00031 Days on yellowkey MLS ID: N6144252
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1979 Tax: $9,073 (2025)Community: Siesta BreakersCondo
Taxes:$9,073
Middle School: Sarasota Middle
Remarks: Turnkey-furnished and move-in ready, experience the ultimate coastal lifestyle in this beautifully maintained beachfront condo located on the beautiful, world-famous Siesta Key. Enjoy the soft, white sand of Crescent beach, with a Beach Attendant managing a 200 ft section of private beach. Whether you’re searching for a full-time residence, seasonal getaway, or income-producing investment property, this luxury condo offers the perfect blend of comfort, convenience, and breathtaking Gulf views. Enjoy relaxing mornings and stunning sunsets from your private screened balcony overlooking the sparkling heated pool, tropical courtyard, and turquoise waters of the Gulf of Mexico. Inside, the condo features an open and airy floor plan filled with natural light, tile flooring throughout the main living areas, and tasteful coastal finishes. The kitchen offers ample cabinetry, stainless steel appliances, recessed lighting, tray ceiling detail, and space for entertaining guests with a breakfast bar & dining area. The spacious primary suite provides a peaceful retreat with pool view, plantation shutters and sliding doors that open to the balcony. The ensuite has been updated with dual granite vanities, large walk-in shower and abundant storage. Open the sliders to the balcony for a seamless indoor-outdoor living experience. Residents and guests enjoy resort-style amenities including a beachfront heated pool, direct private beach access with free beach lounge chairs, option to rent an umbrella or cabana, beautifully maintained grounds, covered parking, grills and lighted tennis / pickleball courts. This condo also offers excellent rental potential, making it a fantastic opportunity for investors seeking vacation rental income in one of Florida’s most desirable beach destinations. Ideally located, walk to restaurants, bars, grocery, boat/bike/kayak/jet ski rentals, gift shops and more! Wake up to the beautiful beach & ocean views, where every day feels like a vacation!
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Heather Lakeman (941-412-6083)
1203 SIESTA BAYSIDE DR #1203-D, SARASOTA, FL 34242
$498,00054 Days on yellowkey MLS ID: A4690769
REDUCED by $27,000 (5.1%) on 04/27/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 959 Built: 1988 Tax: $5,340 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$5,340
Remarks: Sellers Are Highly Motivated! Welcome to your slice of paradise on world famous Siesta Key, just steps from the powdery white sands of Siesta Beach, recently ranked the number one beach in the United States. This beautifully updated one bedroom, one bathroom residence is the perfect blend of comfort, style, and location, ideal as a primary home, vacation retreat, or income producing investment with weekly rentals allowed. From the moment you enter the gated community of Gulf and Bay Club Bayside, you are surrounded by lush tropical landscaping and a sense of pride in ownership that truly sets this community apart. This impeccably maintained residence offers easy single level living with a bright and open layout, finished in a warm neutral palette. The living and dining areas are enhanced with charming details such as wainscoting, while the updated kitchen features stainless steel appliances, beautiful countertops, and well-appointed cabinetry, all flowing seamlessly into the main living space. The oversized primary bedroom offers a peaceful retreat with a large walk-in closet, while the upgraded bathroom features a stunning tile shower, dual sinks with quartz countertops, and excellent storage. A private laundry area adds convenience, and with no carpet throughout, the home is clean, modern, and move in ready. The AC and water heater were both replaced in 2022. Enjoy your morning coffee in the adorable dining nook or unwind in the bright and airy lanai, the perfect place to relax at the end of the day. This residence also includes a rare one car garage and private driveway, making island living effortless. Gulf and Bay Club Bayside offers an exceptional array of resort style amenities including two heated pools, a clubhouse, fitness center, saunas, pickleball and tennis courts, BBQ areas, walking paths, scenic ponds with fountains, and a fishing pier on the Intracoastal Waterway where you can enjoy sunsets, dolphins, and passing boats. Private deeded beach access just across the street makes it easy to enjoy the turquoise waters and world-famous quartz sand whenever you choose. Ideally located between Siesta Key Village and Stickney Point Road, you are moments from top rated dining, boutique shopping, live entertainment, and water activities. The Siesta Key Trolley provides easy access across the island, making every day feel like a vacation. Offered furnished and thoughtfully updated, this residence truly lives larger than expected and is ready for immediate enjoyment. Whether you are looking to relax, entertain, or invest, this is an incredible opportunity to own in one of the most desirable communities on Siesta Key. Schedule your private showing today and experience the coastal lifestyle you have been dreaming of.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
1249 DOCKSIDE PL #110, SARASOTA, FL 34242
$825,00079 Days on yellowkey MLS ID: A4687526
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1217 Built: 1982 Tax: $7,705 (2025)Community: Harbour TowneCondo
Taxes:$7,705
Remarks: Welcome to your slice of paradise on Siesta Key! This beautifully maintained two-bedroom, two-bath first-floor end unit offers a blend of comfort, convenience and coastal living with no stairs to climb and easy access throughout. Ideally just a short two-block stroll to world-famous Siesta Key Beach, you’ll enjoy powdery quartz sand that stays cool underfoot, even on warmest days. This well-maintained island condominium features a roomy layout and comes fully furnished, making it move-in ready or ideal as an income-producing rental. The generous screened lanai overlooks the peaceful marina, creating a spot to relax with your morning coffee or unwind at sunset. Boating enthusiasts will appreciate the sought-after deeded boat dock, providing direct water access to the Intracoastal Waterway. The private garage with overhead storage offers plenty of extra space for beach, fishing gear and more. Within the desirable Harbour Towne community, residents enjoy a host of amenities including a heated swimming pool, spa, tennis and pickleball courts, plus a welcoming clubhouse known for its friendly, social atmosphere. Whether you're seeking a seasonal getaway or investment opportunity, this condominium checks every box. Enjoy the laid-back Siesta Key lifestyle with dining, shopping and entertainment just minutes away, all while living near one of the world’s celebrated beaches.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Peg Davant (941-356-4552)
5132 JUNGLE PLUM RD, SARASOTA, FL 34242
$5,985,000395 Days on yellowkey MLS ID: A4651663
Bed: 5 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 6928 Built: 2008Monthly Fee: $247 Tax: $45,860 (2024)Community: Hidden HarborSpa: YesSingle Family
Taxes:$45,860
Tax Year: 2024
Remarks: Positioned along a deepwater canal in the private, tree-lined enclave of Hidden Harbor on Siesta Key, this remarkable estate captures the essence of timeless coastal architecture and elevated Florida living. With a design that transcends trends and nearly 7,000 square feet of thoughtfully curated interiors, the home embodies a sense of enduring sophistication, where natural materials, warm textures and elegant proportions create an atmosphere that is refined and welcoming. Just over a mile from the world-renowned sands of Siesta Key Beach, this is a home that celebrates the best of Sarasota’s lifestyle, a water connection, a celebration of indoor-outdoor living and architectural details that convey quiet luxury. Set on more than half an acre with 135 feet of water frontage, the residence opens with a stunning walnut-domed foyer, where soaring ceilings and floor-to-ceiling windows flood the space with light. Rich finishes—including Birdseye maple, tongue-and-groove cypress tray ceilings, and handcrafted millwork—are woven throughout the home, delivering a consistent sense of quality and character. The kitchen is a dream for chefs and entertainers alike, appointed with quartz countertops, a large center island, professional-grade appliances, a built-in espresso machine, and a walk-in butler’s pantry that seamlessly connects to formal and casual living areas. The owner’s suite is a private retreat, complete with a sitting room, dual walk-in closets, a spa-style bath with steam shower and a peaceful balcony overlooking the water. Each of the four guest suites offers its own en-suite bathroom and generous closet space, with three featuring walk-in closets and one boasting a built-in wall closet, ensuring privacy and comfort. Whether you need a quiet office, a vibrant game room or a cozy retreat, the bonus room, game room and loft offer the flexibility to suit your lifestyle. True to its coastal character, the home opens fully to expansive covered terraces designed for year-round enjoyment. Retractable screens, a wood-paneled ceiling, integrated fans, and ambient lighting create an outdoor living room atmosphere, complete with a fireplace and a full summer kitchen with built-in grill and bar seating. Beyond, the resort-style pool and raised spa are surrounded by tropical landscaping and natural stone decking, with multiple lounge areas designed for sun and shade. A custom fire pit anchors the space, offering a cozy, elegant setting for evening gatherings with water views. Water enthusiasts will appreciate the boat dock, built to accommodate a large vessel, complete with a boat lift. With quick access to the Intracoastal Waterway, the location is as functional as it is beautiful. Below, the expansive under-building garage offers room for more than 10 vehicles across five bays, plus a workshop, EV charging station and golf cart storage. A brand new whole-house generator was installed in June of 2025, creating peace of mind. Set on a quiet cul-de-sac just minutes from Sarasota’s best beaches, shopping, dining and cultural destinations, this rare offering is a seamless blend of timeless design, superior craftsmanship and the relaxed elegance of coastal Florida living.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
145 AVENIDA MESSINA #3, SARASOTA, FL 34242
$630,000254 Days on yellowkey MLS ID: A4667146
2 Days Off yellowkey (back on 3/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1025 Built: 1966 Tax: $5,561 (2024)Community: Villa NavarraCondo
Taxes:$5,561
Remarks: Welcome to this wonderful condominium complex directly on the edge of the Siesta Key Village! This UPSTAIRS unit has been completely remodeled from top to bottom and is absolutely stunning! The opened kitchen features stainless steel appliances, handsome quartz counters, and a tan tiger-look cabinetry. There is all new lighting, fans, receptacles and switches, and a neutral plank-like ceramic tile flooring throughout. The guest bath was completely remodeled along with the primary bathroom that has been expanded for a little extra elbow room. This has a new water heater and HVAC system, new roof in 2025, all new doors, impact windows, ceiling texture and it doesn't stop there. This comes very tastefully turnkey furnished in a warm coastal theme! Relax on your screened patio and look out to palms and foliage and take in the gulf breezes. The pristine beach is 2/10 of a mile away and the SK Village is about 100 feet away with a large selection of restaurants, shopping, grocery, nightlife, and so much more! Don't miss this beautiful condo in the heart of all that Siesta Key has to offer in a very well-run complex.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joe Cleary (941-650-8485)
1700 COVE II PL #324, SARASOTA, FL 34242
$824,90085 Days on yellowkey MLS ID: A4686403
0 Days Off yellowkey (back on 5/22/2026)
REDUCED by $25,000 (2.9%) on 05/17/2026
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1720 Built: 1979 Tax: $7,965 (2025)Community: Midnight Cove IiCondo
Taxes:$7,965
Remarks: Under contract-accepting backup offers. 3 BEDROOMS ON SIESTA KEY! ONE WEEK RENTALS! DEEDED BEACH ACCESS! WATER VIEWS! DOCKS AVAILABLE! Fantastic 3 bedroom townhouse at Midnight Cove II. 2nd and 3rd floor with lovely views and deeded beach access. Plenty of room for family and friends. Large sized living, dining and kitchen area. Perfect for family gatherings! Midnight Cove II offers deeded beach access directly across the street, marina with slips available, beautiful grounds, grilling area, tennis, pickleball, basketball court, fitness center and a large, heated pool. And bring the large pup too! Great association with onsite rental and management office. Fully funded reserves, milestone inspections complete! Turnkey furnished too! Walk to nearby dining, shopping, water sports and more. See this unit today!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Kim Sheridan (941-313-0262)
116 VISTA HERMOSA CIR #204C, SARASOTA, FL 34242
$575,00023 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 is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Dawn Bear (941-468-7224)
643 CALLE DE PERU, SARASOTA, FL 34242
$1,996,000316 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)
5569 CAPE LEYTE DR, SARASOTA, FL 34242
$4,495,00093 Days on yellowkey MLS ID: A4685577
Bed: 5 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 3654 Built: 2016 Tax: $32,419 (2025)Community: Siesta IslesSpa: YesSingle Family
Taxes:$32,419
Remarks: LOCATION, LOCATION, LOCATION !!! One Block to the Crystal Sands of Siesta Key Beach the #1 Beach in the USA! Or spend the day on the Aqua waters with two boats on lifts out back, and 119' of frontage on the Grand Canal leading to the ICW (only one bridge with about 15’ clearance to the Gulf). Oversized 16,163 sf Lot, elevated concrete block home and spectacular pool in your view from most every room! Not just the best location, but this custom-built in 2016 West Indies style home is a fortress all on one level, including the pool, and is well above the FEMA flood zone. High and dry through the "storms of the century" in 2024. Beautiful, engineered hardwood floors, custom cabinetry throughout by Elite Woodworking in the Kitchen, all Bathrooms and Great Room. The entire house has been freshly painted inside & out. Three large en-suite bedrooms. Additional rooms currently utilized as office with Murphy Bed as well as very large Bonus Room could be utilized as additional bedrooms #4 & 5, if desired. Even the powder bath has a shower for guest convenience. Large walls of sliding glass doors in all waterfront rooms extend living spaces to a huge, screened Lanai which adds over 500 sf to living space under roof, and much more in the screened Lanai area.. All hurricane rated extra heavy duty PGT doors and windows. The total A/C space is 3,654 sf, with a overall total of 5,075 under roof. The oversized 3-car garage with an Epoxy floor has a very high ceiling which allows 2 more cars to be added on lifts for a total of 5 vehicles for the enthusiast. Isonene insulated and floored attic storage space is available above the garage. New in the past year: A/C Condenser & Air Handler system in 1 (of 2) zones, water heater, refrigerator, ice maker, boat lift control boxes on both Lifts. The large free form pool and spa have new (wifi) Pentair pool pump & heater & auto chlorinator. Both boats as well as professional decorator staged furniture, decor and pictures may be available for separate purchase for "Turn-Key" possession. DEFINITELY check out the Virtual Tour, since it provides “3D walk through any direction” photos which can really give you the flow of the house as you manipulate your way around.
Listing Agent: Steve Hagan (941-900-4126)
5830 MIDNIGHT PASS RD #63, SARASOTA, FL 34242
$598,000204 Days on yellowkey MLS ID: A4672897
0 Days Off yellowkey (back on 5/21/2026)
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 728 Built: 1963Monthly Fee: $1,232 Tax: $6,113 (2024)Community: Jamaica RoyaleCondo
Taxes:$6,113
Remarks: Under contract-accepting backup offers. Experience the best of Gulf-side living in this beautifully renovated 1-bed, 1.5-bath condo on Siesta Key — just steps from the world-famous quartz-sand beaches of Siesta Key. Completely updated from top to bottom, this turnkey coastal retreat features brand-new designer furniture and appliances, making it move-in or rental-ready from the moment you arrive. The spacious layout includes a highly desirable extra half bath—a rare and valuable upgrade that enhances comfort for both owners and guests. Inside, you’ll find premium ceramic tile flooring with a warm, wood-inspired finish, European-imported cabinets and interior doors, and modern quartz countertops. The renovated kitchen blends clean lines with elegant finishes, creating a stylish space for cooking, gathering, or entertaining. Other recent upgrades include a new AC and water heater installed in October 2024, providing year-round comfort and peace of mind. Outside your door, you’ll enjoy direct private beach access to Siesta Key’s legendary shoreline—perfect for daily walks, sunset lounging, or soaking up the Gulf breeze. The community also offers three resort-style pools, giving you multiple options for relaxation, swimming, or enjoying the Florida sunshine in a beautifully maintained setting. Whether you're seeking a personal island getaway, a high-demand investment property, or both, this impeccably finished condo delivers the ultimate Siesta Key lifestyle—modern, effortless, and just moments from the Gulf.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Noelle Vihrachoff (570-262-4594)
5830 MIDNIGHT PASS RD #29, SARASOTA, FL 34242
$545,00025 Days on yellowkey MLS ID: A4694023
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1962Monthly Fee: $1,226 Tax: $3,460 (2025)Community: Jamaica RoyaleCondo
Taxes:$3,460
Remarks: Live the ultimate beachfront lifestyle in this beautifully renovated condo located on world-famous Siesta Key, home to the #1 beach in the United States. Completely updated with stylish modern finishes, this coastal retreat offers the perfect blend of comfort, luxury, and location. Enjoy direct access to the powdery quartz sand beaches and stunning Gulf sunsets just yards away. Whether you are looking for a vacation getaway, investment opportunity, or full-time residence, this property offers excellent rental potential in one of Florida’s most sought-after beach destinations. A rare opportunity to own a fully renovated slice of paradise on iconic Midnight Pass Road.
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Cristina Campbell, Pa (561-239-1498)
5830 MIDNIGHT PASS RD #107, SARASOTA, FL 34242
$599,000142 Days on yellowkey MLS ID: A4679302
REDUCED by $50,000 (7.7%) on 05/21/2026
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)
6236 MIDNIGHT PASS RD #305, SARASOTA, FL 34242
$800,000217 Days on yellowkey MLS ID: A4671409
1 Days Off yellowkey (back on 5/21/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1250 Built: 1979Monthly Fee: $1,096 Tax: $8,844 (2025)Community: Siesta Dunes BeachSpa: YesCondo
Taxes:$8,844
Remarks: Under contract-accepting backup offers. Rarely for sale TURNKEY FURNISHED beach condo at Siesta Dunes, where living the Siesta Key lifestyle comes naturally. Enjoy true convenience with DIRECT BEACH ACCESS to powdery white sand and the sparkling Gulf- no streets to cross, just a short, breezy walk to the beach, pool, hot tub, or tennis court right within the community. With onsite management available and WEEKLY RENTALS allowed, owning and renting is refreshingly simple. Whether you're strolling to dinner, biking to the Village, or simply putting your toes in the sand, every moment here feels effortless. Lovingly maintained by the same owner for 40 years, this residence shines with thoughtful updates, brand-new IMPACT WINDOWS for added peace of mind, and even a gorgeous blue Gulf VIEW from your primary bedroom. Whether you're looking for a smart investment or a sunny place to call home, this Siesta Dunes gem is ready to welcome you!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Alex Chau (941-812-8781)
84 AVENIDA VENECCIA #202 & 203, SARASOTA, FL 34242
$7,950,000778 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 Agent: Tom Cail, Pa (941-780-2245)
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