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5830 Midnight Pass Road Unit 101, Sarasota
$560,000
2 Beds ⋅ 2 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Beach living on Siesta Key. Discover the ultimate coastal retreat in this completely remodeled condominium, positioned along the pristine shores of Siesta Key. Jamaica Royale offers 300 feet of private white sandy beach on Siesta Key Beach with lush tropical grounds and this two-bedroom, two-bath residence has been completely renovated and is offered turnkey furnished, ready for immediate enjoyment. Go inside to find luxury vinyl floors and an open floor plan that seamlessly blends beach vacation with functionality. The kitchen is beautifully redone featuring stainless steel appliances, quartz countertops, shaker style cabinets with soft-close doors and drawers. The spacious primary suite is a private space with a stunning en suite primary bath. There is plenty of storage with extra deep double closets in both bedrooms. The additional bedroom provides ample comfort for your guests with two full beds. You will appreciate the convenience of your laundry closet, private patio and covered parking directly outside your door. This exceptional condominium offers a combination of beach fun, stylish comfort and unbeatable coastal living. Jamaica Royale is on a private lane that leads directly to the beach with no through traffic and no streets to cross ~ just go to the famed white sands of Siesta Key Beach. There are three pools and plenty of lounge chairs to enjoy the beach life. Enjoy quiet, beachfront seclusion where you can soak up the sun, cool off in the water and view the beautiful sunsets. You are steps to the beach where you can walk the white quartz sand that is soft underneath you while enjoying the tranquility of soft waves splashing, and beautiful turquoise waters. The drum circle is sure to entertain you some nights or just sit and watch a beautiful sunset. If you prefer, at any given time of the day, you can catch the shuttle which will transport you up and down Siesta Key to your favorite entertainment spot, dinner, and/or shopping.

5830 Midnight Pass Road Unit 101, Sarasota

1055 W Peppertree Drive Unit 505AA, Sarasota
$555,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Peppertree is a Gulf-to-Bay community of resort style living situated on 16 acres of beautifully landscaped tropical grounds, providing private access to Crescent Beach and within easy walking distance of Siesta Key Beach and Siesta Village. Amenities include two clubhouses, two heated pools, tennis courts, a recently renovated fitness center with locker and sauna, and a fishing pier on the Intracoastal Waterway, BBQ grills, on-site management, rental program and security. Original owners! This vintage unit is located on the gulf side of the property and is ready for a remodel, allowing you to create your dream coastal retreat. Spacious supersized laundry/utility inside the unit. Secure elevators and under building parking is provided. New hurricane windows to be installed by the association at no cost to the owners. Shopping, golfing, restaurants and the Arts are all just minutes away. This is a rare opportunity to own in one of Siesta Key's most desirable communities. Don't miss out - schedule your private showing today!

1055 W Peppertree Drive Unit 505AA, Sarasota

6415 Midnight Pass Road Unit 705, Sarasota
$550,000
2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code
Welcome to the best location on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Walk to bars, restaurants, the beach. You can walk across the street and rent a boat. Speaking of boats you can dock your boat on our giant seawall for $10.00... yes...ten dollars a month. Your new condominium is an open floor plan with living room/dining room combo. All three rooms have hurricane sliding doors. The main bedroom is very large and the master bath has a walk-in shower. The guest bedroom has 2 double beds with a tub/shower! You also have one covered parking space underneath the main building valued at $25,000.00. We have a beach easement to Siesta Key beach! Our Seawall was replaced in 2019. The building and grounds are in wonderful shape! The Anchorage has so many amenities to offer owners and renters, including an Olympic-size heated swimming pool, Fitness Center, Lighted Pickleball & Tennis Courts, Clubhouse, BBQ & Picnic Areas and Kayak Storage! There is a trolly that you could take to Siesta Key Village to enjoy more shopping, entertainment and dining options. The Anchorage is very conveniently located near Stickney Point Bridge to give you easy access to the mainland, including downtown Sarasota!

6415 Midnight Pass Road Unit 705, Sarasota

6415 Midnight Pass Road Unit 306, Sarasota
$550,000
2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code
Welcome to one of the best locations on Siesta Key. The Anchorage is located on the corner of Stickney Point and Midnight Pass. It’s all about convenience and living the good life. Location is fantastic! Wait until you see the grounds! You have the best of both worlds. Your new condominium is a 2 bedroom 2 bathroom split plan with brand-new hurricane sliding doors. Inside you have abundant natural light and a spacious combo kitchen/dining room/living room setting offering a move-in-ready condition. What truly sets The Anchorage apart is its canal-front dockage with first-come, first-serve boat slips, providing direct access to Sarasota Bay and the Intracoastal Waterway. For boating enthusiasts, this is an exceptional value, $10.00 per month boat slip fee. This is crazy insane ridiculous pricing for a boat slip…offering a rare opportunity to enjoy waterfront living and boating convenience without the premium price or waitlists typically found on Siesta Key. The building is solid concrete! Buyer has one car spot #77. This is a perfect investment for rental opportunities. Weekly rentals are allowed. The building and grounds are in wonderful shape! The Anchorage has so many amenities to offer owners and renters, including an Olympic-size heated swimming pool, Fitness Center, Lighted Pickleball & Tennis Courts, Clubhouse, BBQ & Picnic Areas and Kayak Storage. If you have a boat, The Anchorage also offers free dockage along the Seawall! There is a trolly that you could take to Siesta Key Village to enjoy more shopping, entertainment and dining options. Your new condo has its own carport. The Anchorage is very conveniently located near Stickney Point Bridge to give you easy access to the mainland, including downtown Sarasota!

6415 Midnight Pass Road Unit 306, Sarasota

5830 Midnight Pass Road Unit 63, Sarasota
$550,000
1 Beds ⋅ 2 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
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.

5830 Midnight Pass Road Unit 63, Sarasota

1325 S Portofino Drive Unit 309, Sarasota
$550,000
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
*****UNDER CONTRACT, ACCEPTING BACK UP OFFERS***** -$108,900 MAJOR PRICE REDUCTION! Priced to sell quickly. Owner retiring from Property investments. The ONLY All Age Building (Pompano) in Siesta Harbor! No need to search anymore since this is not a 55+ condo on World Renowned Siesta Key, Florida. This unit is on the 3rd floor and did Not suffer any hurricane damage. High and Dry! This is the one! 2/2 Split plan condo with beach access. Completely furnished with Tommy Bahama furnishings with Kitchen, Dining and Living room and lanai all encompassed in an Open Floor plan. Water views from every room. The Florida room expands beyond the Dining and Living Room area creating an Indoor/Outdoor experience. Open up the Sliders in the Florida room and enjoy a Screened in porch for fresh air and year around Florida temperatures. Don't forget, Florida is called the Sunshine State for a reason! Enjoy the Siesta Key life annually or use as a seasonal unit. This unit has been rented over the years with satisfied tenants, several asking to come back the next year. Fabulous investment property whether you use it for yourself or as a short term or long-term rental, or BOTH. Buyer must verify rental requirements with the association. Currently a 2-month minimum. Boat slips available for up to a 30 ft vessel - around $1,000 annual fee which association will verify. New Water heater installed 2-5-21. New AC installed 4-25-22. Shower pan; stacks and both bathrooms have updated plumbing. Community includes a clubhouse with kitchen, BBQ, heated pool, outdoor spa and shower, sauna, state of the art fitness center, daily activities, shuffleboard, fishing pier and more. Storage unit and laundry area outside of unit on the same floor. Designated underground parking space with remote control and open parking available. This is a beautiful condo and location! Walk across the street (FOB use required) for your deeded private access to the beach or 2 blocks from Captain Curts, the grocery store or Crescent Beach. This condo has it all. Motivated seller. Set up your showing today! #1 Rated beach in the USA for several years! Live the Salt Life! Please submit all offers to listing agent with either POF or prequalification letter. Buyer to pay all closing costs except Doc Stamps.

1325 S Portofino Drive Unit 309, Sarasota

782 Birdsong Lane, Sarasota
$550,000
2 Beds ⋅ 2 Baths ⋅ Siestas Bayside Waterside SubDv. ⋅ 34242 Zip Code
Opportunity knocks in one of the most sought-after locations on Siesta Key! Roof in good shape and impact windows throughout the home. This prime property offers the perfect chance to create your ideal coastal retreat. Situated just moments from world-famous Siesta Key Beach, this lot presents a blank canvas for a stunning new build or a visionary renovation. Currently, the property features a 2-bed, 2-bath home, which has been stripped to the studs following storm damage. Whether you choose to restore and reimagine the existing structure or start fresh with a custom-built masterpiece, this is your chance to bring your vision to life while incorporating modern building codes and coastal design elements. Enjoy the island lifestyle with white sandy beaches, turquoise waters, and vibrant dining and shopping nearby. Seize this rare opportunity to craft the ultimate dream home in paradise!

782 Birdsong Lane, Sarasota

6150 Midnight Pass Road Unit V4, Sarasota
$550,000
2 Beds ⋅ 1 Baths ⋅ Island House SubDv. ⋅ 34242 Zip Code
Welcome to this stunning waterfront Siesta Key beach community featuring a private beach, gorgeous views of the Gulf, and spectacular sunsets. Lowest priced beachside Villa. This spacious, fully furnished, two bedroom single family Villa was totally renovated in 2025. The large new kitchen is a masterpiece with stainless steel appliances and quartz countertops. The huge open living area features a living room and dining room each with access to the screened front porch. Two spacious bedrooms and a stunningly renovated new bathroom round out this beautiful villa. The true treasure of this community lies in its direct access to the world-famous Siesta Key Beach, complete with private beach cabanas, a beach rinsing station, community pool, and beach chairs. Potential rental income of $50k make this a great investment property.

6150 Midnight Pass Road Unit V4, Sarasota

757 Beach Road Unit 308, Sarasota
$545,000
1 Beds ⋅ 1 Baths ⋅ Crescent Royale SubDv. ⋅ 34242 Zip Code
Prime location directly across the street from Siesta Key Public beach has a full Gulf view that enjoys gorgeous sunrises and sunsets! Unit was completely gutted and remodeled with high end finishes, paint, and furniture in 2011. Everything is in excellent condition. This third floor unit in the highly desired Crescent Royale Condominium complex has a screened lanai, assigned covered parking space and storage locker for beach gear. Complex has large heated pool, grills with picnic area, bike parking, shuffleboard, a Clubhouse with pool table, exercise room and bathrooms. One mile to the Village restaurants and shops. This unit is sold turnkey furnished and allows weekly rentals. Use excellent on-site management or DIY on VRBO and AirBNB. Start your revenue stream from day one - ask to see our stunning rental history! Great income producer - $48,622 in 2025

757 Beach Road Unit 308, Sarasota

1900 Cove Ii Place Unit 122, Sarasota
$535,000
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code
OPPORTUNITY KNOCKS - UNOBSTRUCTED WATER VIEWS!!! RARE OPPORTUNITY, INCREDIBLE PRICE - DIRECT INTRACOASTAL WATERFRONT | DEEDED BEACH ACCESS | 2 OVERSIZED BEDROOMS | WEEKLY RENTALS. Experience the best of both worlds at Midnight Cove II—complete privacy and breathtaking direct Intracoastal Waterway views, combined with a deeded beach walkway just across the street to the pristine sands of Crescent Beach and world-famous Siesta Key Beach. This beautifully furnished, move-in-ready 2-bedroom, 1½-bath condo offers an exceptional waterfront lifestyle and the flexibility of weekly rentals, making it an ideal vacation retreat, personal residence, or investment property. Step inside and immediately take in the abundance of natural light and the unobstructed direct-water views. This is the only building in Midnight Cove II offering a direct east-facing Intracoastal view, creating a spectacular setting to watch boats and jet skis pass by, dolphins glide through the water, and Florida's beautiful birds soar overhead. The open kitchen has been thoughtfully updated with beautiful new lighting, attractive cabinetry, abundant storage, an appliance garage, newer appliances, and a large granite countertop with seating for two. The walls have been removed from the lanai, creating a more expansive living area and allowing the spectacular waterfront setting to become part of the living space. Both bedrooms are generously sized to accommodate king-size beds. The primary bedroom is beautifully furnished with a quality King bedroom suite, while the second bedroom features comfortable twin beds and equally attractive modern furnishings. Both bedrooms include excellent closet and storage space. A stackable washer and dryer are conveniently tucked behind mirrored glass doors, along with additional storage. Even more storage is available just steps from the front door—perfect for beach chairs, umbrellas, and other beach essentials. Midnight Cove II offers an impressive resort-style amenity package, including: Large heated swimming pool and expansive pool deck, Newly rebuilt pickleball and tennis courts, Basketball court, Fitness center, Clubhouse, Lush tropical landscaping and mature oak trees, Kayak storage near the water, Fishing pier extending toward the Intracoastal Waterway, Rental dock space for boats, subject to availability and applicable fees, Multiple BBQ areas, Car wash area, Active community programming, including live music, yoga, and tennis. For investors, weekly rentals are permitted, and the on-site rental management operation provides an attractive option for owners who want professional assistance managing their vacation rental. For personal enjoyment, the location is hard to beat. Cross the street to the deeded beach walkway and you're on the way to the spectacular quartz-rich sands of Crescent Beach and Siesta Key Beach. Enjoy nearby restaurants, shopping, entertainment, and an easy trolley ride to Siesta Key Village for dining, dancing, live music, shops, and more. Waterfront privacy. Beach access. Weekly rental potential. Two spacious bedrooms. Resort amenities. And an extraordinary direct Intracoastal view. This is the kind of Siesta Key property that offers something for everyone—a place to enjoy, a place to escape, and an opportunity to generate rental income when you're away.

1900 Cove Ii Place Unit 122, Sarasota

1400 Cove Ii Place Unit 631, Sarasota
$535,000
2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code
Welcome to the most adorable condo on world famous SIESTA KEY. Start enjoying the island lifestyle in this TURNKEY furnished condo with GREAT WATER VIEWS and pool views! ***WEEKLY RENTALS ALLOWED***Very comfortable open floor plan with balcony to sip your cocktails relax and enjoy the view! The PRIVATE DEEDED BEACH ACCESS to the quartz sand Siesta beach in priceless. Midnight Cove offers tennis, pickleball, barbecue areas, fitness, pool, on site management and rental services, boat docks and more. Take the free trolley to Siesta Village or walk to the south village restaurants and shops. Downtown Sarasota and St Armand's Circle just a short drive away. An excellent opportunity for your vacation getaway or investment property.

1400 Cove Ii Place Unit 631, Sarasota

8977 Midnight Pass Road Unit 223, Sarasota
$535,000
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Experience coastal living at Sunrise Cove, one of Siesta Key’s most amenity-rich and sought-after waterfront communities. This beautifully updated 2-bedroom, 2-bath residence offers an ideal location directly on Sarasota Bay and just across from the turquoise waters and sandy shoreline of Turtle Beach. Updated within the last four years and offered turn-key furnished, this home features impact-rated windows, new flooring, upgraded lighting, HVAC, and kitchen improvements, all designed with a bright coastal aesthetic. The open concept layout flows from the kitchen to the dining and living areas and out to a private terrace where breathtaking sunrises over the bay greet you each morning. With the recent opening of Midnight Pass, the bay now boasts exceptional water clarity in vibrant blues and greens. Boaters will appreciate the rare ability to dock on property at the expansive new dock and slips currently under construction, with an additional full-service marina conveniently located at the adjacent property. Sunrise Cove offers true resort-style amenities including two heated waterfront pools, a recently updated clubhouse with kitchen, ping-pong and billiards, a fitness center, BBQ and picnic area, two lighted tennis/pickleball courts, kayak storage and launch, covered parking, and a washer and dryer on every floor. A popular bayfront restaurant is just steps away, with more dining, shopping, and nightlife a short distance up the road in Crescent Village. This residence delivers the perfect combination of beach access, boating, and amenity-rich island living—move in this season and enjoy the best of Siesta Key.

8977 Midnight Pass Road Unit 223, Sarasota

8779 Midnight Pass Road Unit 401H, Sarasota
$535,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
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, cute brunch spots and dancing and live music every night of the week!

8779 Midnight Pass Road Unit 401H, Sarasota

6012 W Peppertree Way Unit 227B, Sarasota
$532,500
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Gulf-Side Condo on Siesta Key! Don’t miss this great opportunity to own a beautiful condo with a pool view and just steps from the beach. This spacious first-floor unit features 2 bedrooms and 2 bathrooms, high ceilings, and generously sized rooms that provide plenty of space for family and guests. The condo also includes a private garage and the convenience of an in-unit washer and dryer. Ideally located just a short walk from the pool, fitness center and the beach, this home is part of Peppertree Bay, a desirable beach-to-bay community. Residents enjoy an impressive array of amenities, including a private beach, two heated pools, two clubhouses perfect for gatherings, BBQ areas, tennis and pickleball courts, a fitness center, sauna, and a fishing pier. On-site management adds to the ease of ownership, making this an ideal full-time residence, vacation home, or investment property.

6012 W Peppertree Way Unit 227B, Sarasota

9397 Midnight Pass Road Unit 505, Sarasota
$530,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
Discover an exclusive, gated oasis at the southernmost tip of Siesta Key. This recently renovated 5th-floor condo, nestled within the private 5.2 acre community of The Pointe, offers a lifestyle of unparalleled luxury & tranquility. The residence provides a rare opportunity to witness breathtaking sunrises over Sarasota Bay & celebrate unforgettable sunsets over Midnight Pass & the Gulf of America. Inside, a chef’s kitchen features solid-wood, soft-close cabinetry, granite countertops & several new appliances. The 2 full bathrooms are equally modern with new fixtures & sleek quartz vanity tops. Throughout the light-filled, move-in-ready home with Impact Glass windows, elegant luxury vinyl & porcelain tile provide low-maintenance sophistication. The new professional staging can be included or purchased separately. Relax on your spacious, 29-foot screened lanai as you watch kayakers glide over the water & observe the natural beauty of the Neville Bird Sanctuary. Engage with resort-style amenities, including a heated lap pool & spa, lighted tennis & pickleball courts, a fitness center & saunas. The pet-friendly community offers the ultimate peace of mind with a dedicated management team & dual elevators. For the boater, slips up to 26 feet & kayak storage are available for a nominal annual fee. Located on an elevated part of the Key, this property had no water damage or storm assessments in 2024. Enjoy the convenience of a short stroll to Turtle Beach & the free public trolley to Siesta Village & Siesta Beach.

9397 Midnight Pass Road Unit 505, Sarasota

8977 Midnight Pass Road Unit 519, Sarasota
$527,500
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Wake Up Above Sarasota Bay — Penthouse Views, Coastal Living, and Endless Horizons! Imagine beginning each day from your top-floor residence with breathtaking panoramic views of Sarasota Bay and glimpses of the Gulf of Mexico beyond. From morning coffee to spectacular sunsets reflecting across the water, this exceptional 2-bedroom, 2-bath condominium offers a front-row seat to Sarasota's coastal beauty. Perched on the top level, this light-filled residence showcases expansive water views, abundant natural light, and an inviting floor plan designed for comfortable living and effortless entertaining. Watch sailboats glide across the bay, spot dolphins at play, and enjoy the ever-changing scenery from the comfort of your own home. Whether you're searching for a year-round residence, seasonal retreat, or investment in one of Sarasota's most desirable locations, this residence offers the perfect blend of luxury, convenience, and waterfront charm. Ideally located near world-renowned beaches, vibrant downtown Sarasota, exceptional dining, shopping, arts, and cultural attractions, you'll enjoy the very best of Florida's Gulf Coast lifestyle. Top Floor opportunities with sweeping bay views and Gulf vistas are rare. Experience elevated living where every day begins and ends with unforgettable views. If it can't get any better than this, January and Feburary are rented bringing immediate income to future owner!

8977 Midnight Pass Road Unit 519, Sarasota

8767 Midnight Pass Road Unit 101F, Sarasota
$525,000
2 Beds ⋅ 3 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
$50,000 Price Improvement — Now One of the Best Values on Siesta Key. At $535,000, this 1,700+ sq ft Island Reef condo is priced in line with nearby 1,300 sq ft units—creating a rare opportunity to own significantly more space without paying a premium. Located on the quieter south end of Siesta Key, this ground-floor residence overlooks Little Sarasota Bay and offers the kind of easy, coastal living that’s increasingly hard to find. The split-bedroom layout features two en suite bedrooms positioned on opposite sides of the condo, plus a half bath and a flexible space ideal for a small home office. Inside, the scale of the home stands out immediately—a massive living area, separate dining room, and an enclosed Florida room that captures peaceful bay and Intracoastal views. Natural light fills the space from morning through mid-day, while ceramic tile flooring throughout keeps maintenance simple and practical. The kitchen is equipped with butcher block countertops, abundant cabinetry, and a full-size layout that supports everyday living or extended stays. A full laundry room with standard-size washer and dryer adds to the convenience. What truly sets this unit apart is its ground-floor accessibility, generous square footage, and a strong track record of staying dry during past storms—an increasingly important consideration for waterfront buyers. Island Reef is a well-maintained, financially sound Gulf-to-Bay community with no upcoming assessments and on-site management. Residents enjoy deeded beach access just a short walk away, along with bayfront boat docks (with lift options), two heated pools, tennis and pickleball courts, fitness center, clubhouse, and an active social calendar. The free Siesta Key trolley stops right in front of the community, providing easy access to Siesta Village, dining, shopping, Turtle Beach, and nearby marinas. Offered turnkey furnished, this is a compelling opportunity for full-time living or seasonal enjoyment—especially for buyers who recognize value when they see it. Schedule your private showing today.

8767 Midnight Pass Road Unit 101F, Sarasota

5830 Midnight Pass Road Unit 107, Sarasota
$525,000
2 Beds ⋅ 2 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
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!

5830 Midnight Pass Road Unit 107, Sarasota

9393 Midnight Pass Road Unit 201, Sarasota
$525,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
Welcome to your waterfront paradise. The Pointe at Midnight Pass on Siesta Key, is a 5+ acre gated coastal oasis surrounded by Little Sarasota Bay, the ICW, Blind Pass Lagoon, the Gulf of Mexico, and Jim Neville Marine Preserve. This beautifully updated 2BR/2BA second-floor condo showcases breathtaking water views and invites you to experience nature up close with frequent visits from playful dolphins, gentle manatees, and an array of vibrant seabirds. This tranquil waterfront setting perfectly complements a lifestyle of adventure and relaxation. Enjoy direct water access with kayak launches and boat docks—ideal for paddling, fishing, or cruising. Inside, the gourmet kitchen is a chef’s dream, showcasing granite countertops, custom wood cabinetry, and classic travertine flooring. High-end details continue throughout, with luxury ceiling upgrades that include recessed lighting, crown molding, and refined architectural accents—adding depth and elegance to every room. Built-in custom wood cabinetry and shelving provide both beauty and functionality throughout the condo. Both bedrooms boast stunning water views and direct access to the lanai, where you’ll enjoy breathtaking panoramic vistas—the perfect place to unwind and take in the coastal serenity. Resort-style living awaits at The Pointe, featuring a heated pool, spa, fitness rooms, clubhouse with full kitchen, outdoor grilling and picnic areas, herb garden, lighted tennis and pickleball courts, lush tropical landscaping, butterfly gardens, and your very own private island with BBQ, gazebo, and a front-row seat to observe The Pointe’s resident osprey nest. Seasonal social events, plus walk, bike, or drive to Turtle Beach with ample parking, Crescent Beach, Point of Rocks, and Siesta Key Beach. Free Siesta Breeze Trolley nearby. Easy walk, bike, drive, or trolly to local shopping, dining, entertainment, and recreational water activities. Seize the opportunity to own at this stunning waterfront sanctuary—schedule your private tour today and begin living the coastal lifestyle you've always dreamed of.

9393 Midnight Pass Road Unit 201, Sarasota

5830 Midnight Pass Road Unit 25, Sarasota
$522,500
1 Beds ⋅ 1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Now pending—accepting backup offers. Turnkey furnished 1 bedroom, 1 bathroom condo at Jamaica Royale on Siesta Key, offering a true hands-off investment opportunity with onsite rental office and future bookings already in place for 2026. This fully renovated condo features high-end finishes and thoughtful upgrades throughout, making it ideal as a vacation rental, second home, or full-time residence. The updated kitchen showcases quartz countertops, a coastal-inspired backsplash, soft-close cabinetry, brand-new stainless steel appliances, and a spacious island—perfect for entertaining. Luxury waterproof vinyl plank (LVP) flooring flows throughout the living area, which is furnished with all-new high-end furniture. The large bedroom is furnished with two queen beds, offering comfort and flexibility for guests. The spa-inspired bathroom features a walk-in shower with built-in bench, porcelain tile, and a sleek backlit mirror. Thoughtful storage, including an expanded hallway closet, enhances functionality and makes this condo truly move-in ready. Jamaica Royale is a well-maintained beachfront community known for its private deeded beach and resort-style amenities, including three pools (one beachfront), newly renovated beachside restrooms and changing facilities, and an outdoor kitchen with grills and seating. With onsite rental management, this condo provides an easy, low-maintenance investment opportunity. Whether you’re searching for a turnkey vacation rental, income-producing investment property, or coastal retreat, this Jamaica Royale condo offers location, luxury, and convenience.

5830 Midnight Pass Road Unit 25, Sarasota

1140 S Moonmist Court Unit M5, Sarasota
$520,000
2 Beds ⋅ 2 Baths ⋅ Polynesian Gardens SubDv. ⋅ 34242 Zip Code
FULLY renovated and appointed, in 2025, villa. Offered turnkey furnished, ready to use or rent for the season! The Polynesian Gardens community is well located on Siesta Key's south end; Walking distance to shopping, dining, nightlife of Captain Curt's corner, coffee and ice cream shops, grocery store, public beach access, boat rentals, and all things Siesta Key! Grab a golf cart or Free Trolly to the village for additional adventures, relax by the community pool or look for manatee and dolphins on the community dock overlooking the Intracoastal Waterway. This charming 2 bed 2 bath villa, with 2 patio's, an outdoor shower for post beach sand removal, offers the perfect beach lifestyle, living like a home with the convenience of a lock and go, low maintenance villa. Come relax, enjoy the beauty of SK!! Some personal items and artwork do not convey

1140 S Moonmist Court Unit M5, Sarasota

8977 Midnight Pass Road Unit 224, Sarasota
$512,500
2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
Welcome to Your Slice of Paradise at Sunrise Cove. It starts with the light. From the moment you step into this rarely available second-floor end unit, you're greeted by an abundance of natural sunlight and sweeping views of the bay. With almost 1,400 square feet, this is one of the largest floorplans in the entire community. Inside, you'll find tile and luxury vinyl flooring throughout, an in-unit washer and dryer, and a layout that lives large, whether you’re relaxing or entertaining. Offered turnkey furnished, it’s ready for you to drop your bags and begin enjoying the laid-back luxury of life on Siesta Key. Start your morning with coffee overlooking the bay, then head across the street to Turtle Beach for a walk in the sand or a swim in the Gulf. If you're a boater, take advantage of available dock slips just steps from your door—ideal for quick access to Sarasota Bay and beyond. Prefer a paddle? There’s also a kayak launch ready for your next adventure. Back at Sunrise Cove, the recently renovated clubhouse offers a stylish space to gather, complete with fitness center and social areas. Take a dip in one of two heated pools, meet friends for a match on the tennis or pickleball courts, and end the day with dinner at nearby favorites like Ophelia’s on the Bay or Turtle’s Restaurant, both within walking distance. With a one-month minimum rental policy, Sunrise Cove provides a rare balance of income potential and residential charm. This is the kind of place that feels like vacation but lives like home.

8977 Midnight Pass Road Unit 224, Sarasota

925 Beach Road Unit 107, Sarasota
$512,000
2 Beds ⋅ 2 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code
Offered at $529,000, this 2-bedroom, 2-bath residence represents one of the most competitively priced opportunities to own directly across the street from Siesta Key Beach. Enjoy effortless access to the sugar-white sand and turquoise waters with an easy five-minute walk—no driving, no searching for parking, just the relaxed coastal lifestyle that makes this location so desirable. With one of the largest two-bedroom, two-bath floor plans in the community, this residence offers approximately 940 square feet of comfortable living space with an open-concept layout designed for easy island living. The updated kitchen showcases wood cabinetry, granite countertops, and stainless steel appliances, flowing seamlessly into the dining and living areas. Tile flooring throughout provides durability and low-maintenance living, while the split-bedroom design provides added privacy for owners and guests alike. Weekly rentals are permitted during peak season, with a minimum four-day rental period during the off-season, creating exceptional flexibility and increased income-producing potential throughout the year. On-site rental management is available for owners seeking a turnkey investment, and a comprehensive investor package, including historical rental income and operating information, is available upon request. The residence also includes a deeded covered carport along with ample guest parking. 925_Beach_Rd_107_Investor_Package 2.pdf La Siesta residents enjoy a heated swimming pool, fitness center, clubhouse, and beautifully maintained tropical grounds. Located just minutes from Siesta Key Village’s restaurants, boutique shopping, and entertainment, the community offers the perfect blend of relaxation, convenience, and investment potential. Whether you’re searching for a personal beach retreat, a seasonal residence, or a high-demand vacation rental, this property offers an exceptional opportunity to own in one of Siesta Key’s most desirable locations at a compelling price.

925 Beach Road Unit 107, Sarasota

925 Beach Road Unit 112, Siesta Key
$506,000
2 Beds ⋅ 2 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code
Endless vacations await at La Siesta! Condo-hotel daily/weekly/monthly rental allowed through association. This highly desirable first-floor, recently remodeled two-bedroom, two-bath corner condo has been beautifully updated throughout, including a modern new kitchen, stylish finishes, and tasteful décor. The open layout and all-tile flooring make the space bright and inviting for both relaxation and entertaining. Step out to your private screened lanai and enjoy a short stroll to the main entrance of Siesta Beach, ranked the #1 beach in the U.S. by TripAdvisor in 2020. Spend your days on the island’s famous quartz sands, play volleyball or tennis, dine at Siesta Beach Eats, or take in breathtaking Gulf sunsets from the beachside viewing deck. At La Siesta, you’ll enjoy resort-style amenities including a heated pool, fitness center, clubhouse, grilling stations, on-site laundry, and professional full-time management. A covered parking space and additional storage are also included. With a seven-day rental minimum and strong demand year-round, this unit offers excellent income potential, with bookings already secured well into 2026. Perfectly situated near the shops and restaurants of Siesta Key Village, and with easy access via Stickney Point Road, this turnkey-furnished residence blends vacation living, smart investing, and everyday comfort. Move-in ready, recently renovated, and steps from Siesta Beach — this is the opportunity you’ve been waiting for.

925 Beach Road Unit 112, Siesta Key

1125 W Peppertree Drive Unit 302, Sarasota
$500,500
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Discover the potential of this 2-bedroom, 2-bath condominium in the highly sought-after Peppertree Bay community on Siesta Key. Located on the Gulf side with deeded beach access, this residence offers easy, direct access to Siesta Key’s world-famous quartz sand beach, making it highly attractive to both owners and renters. The condo provides a great opportunity to personalize and add value to suit your style. Monthly rentals are permitted up to four times per year, offering strong income potential in a consistently high-demand vacation market. All new windows are scheduled to be installed in 2026 at no cost to the owner with no assessment required, enhancing long-term value and appeal. Peppertree Bay is a well-established, amenity-rich community featuring a resort-style pool, fitness center, tennis courts, and beautifully maintained grounds, all of which are highly desirable to owners and renters. Whether you’re seeking a personal beach retreat with income potential or a strategic investment on Siesta Key’s Gulf side, this property offers a rare combination of location, rental flexibility, and upside potential.

1125 W Peppertree Drive Unit 302, Sarasota

4660 Ocean Boulevard Unit Q1, Sarasota
$500,000
2 Beds ⋅ 2 Baths ⋅ Sea Village SubDv. ⋅ 34242 Zip Code
PRICED TO SELL! NEW impact-rated sliding glass doors were installed in June 2026, providing enhanced storm protection and complementing the home’s existing hurricane-impact windows. 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 additional protection 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.

4660 Ocean Boulevard Unit Q1, Sarasota

175 Island Circle, Sarasota
$500,000
2 Beds ⋅ 1 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Discover a unique opportunity to embrace the Siesta Key lifestyle in this 1952 cottage. Nestled in the Heart of Palm Island - a tranquil neighborhood and just a short walk from both iconic Siesta Key Beach and vibrant Siesta Key Village. This property is a blank canvas awaiting your vision. Whether you’re considering a renovation or building it up or tearing it down to build your dream home, endless potential awaits. The home backs onto a serene, tidal saltwater ravine, offering a private backdrop. With ample room for a pool and personalized landscaping, this home invites you to create your own outdoor oasis. Please note that there is mold present as a result of the past hurricane. This is an exciting project for the visionary buyer. Step into a lifestyle where every day feels like a vacation. Your Siesta Key sanctuary awaits! Roof 4 years old A/C replaced in 2019. Pecky Cypress siding, wood beamed ceilings. Loaded with potential. Great quiet neighborhood.

175 Island Circle, Sarasota

5219 Calle De Rio, Sarasota
$500,000
Sarasota Beach SubDv. ⋅ 34242 Zip Code
Major Price Reduction for this buildable lot.... New Years Resolution.. Build the Dream House on Siesta Key!!! Seize this rare opportunity to own a ready-to-build lot just steps from Siesta Key Village in one of the island’s most sought-after locations! Why You'll Love This Property: ~Cleared & Ready to Build – No demolition needed—just bring your vision to life! ~Flexible Use – Ideal for a luxury residence, vacation retreat, or high-income rental. ~Prime Location – Walk to Siesta Key Village for dining, shopping, and entertainment. ~Beach Life Awaits – Minutes from Siesta Key Beach, known for its powder-soft quartz sand & breathtaking sunsets. Whether you're dreaming of an elegant coastal oasis or a savvy investment property, this blank canvas is waiting for you. Don’t miss out—make your Siesta Key dream a reality today!

5219 Calle De Rio, Sarasota

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