Siesta Key Homes under $500,000

Siesta Key Homes under $500,000

Welcome to Siesta Key, Florida – a picturesque barrier island nestled along the stunning Gulf Coast in Sarasota County. Known for its powdery white sands and vibrant turquoise waters, Siesta Key is more than just a beach paradise; it’s a community filled with charm, character, and an enviable lifestyle that attracts residents and visitors alike.

Siesta Key boasts a laid-back atmosphere that perfectly complements its natural beauty. With a variety of outdoor activities, from kayaking and paddleboarding to sunset strolls on the beach, there's always something to keep you engaged. The local dining scene is a culinary delight, offering everything from fresh seafood to gourmet cuisine, ensuring that every meal is a memorable experience.

For those looking to make Siesta Key their home, there are fantastic opportunities available, especially for properties under $500,000. Whether you're seeking a cozy beachfront condo, a charming cottage, or a modern townhouse, Siesta Key offers a range of options that cater to diverse tastes and budgets. These homes provide an ideal retreat for those wanting to embrace the island lifestyle, while still being within reach of the vibrant city of Sarasota, known for its arts, culture, and shopping.

Living in Siesta Key means enjoying a unique blend of relaxation and recreation, all while being part of a welcoming community. With its stunning scenery, rich local culture, and affordable housing options, Siesta Key is truly a hidden gem waiting to be discovered. Explore your dream home today and start living the life you've always envisioned!

Newest Siesta Key Homes under $500,000

5950 Midnight Pass Road Unit 101, Sarasota
$485,999
1 Beds ⋅ 1 Baths ⋅ Siesta Beach House SubDv. ⋅ 34242 Zip Code
An exceptional opportunity to own a beautifully updated and turn-key beach condominium in the heart of Siesta Key, offering the flexibility of a strong rental investment, seasonal getaway, or your own private coastal retreat. Built a solid foundation of bookings into February and March bookings. Repeat Guests and higher demand! Located within Siesta Beach House this residence places you just a short walk to both Siesta Beach and Crescent Beach, while also offering the rare advantage of private beach access exclusively for residents and guests. Inside, the condo has been thoughtfully upgraded and meticulously maintained, creating a bright and modern coastal atmosphere. The kitchen features quartz countertops, ceramic tile backsplash, under-cabinet lighting, stainless steel appliances, and solid wood cabinetry, all opening seamlessly into the main living space. Porcelain ceramic tile flooring runs throughout, enhancing the clean, beach-inspired feel of the home. Additional improvements provide peace of mind and long-term value, including a new elevated A/C system installed in 2024 and a brand-new electrical panel completed in 2025. Beautiful upgraded baseboards in the living room, extra hallway storage, and tasteful finishes throughout further separate this condo from many others currently available on the island. The spacious bedroom includes a walk-in closet, while the open-concept floor plan maximizes functionality and comfort within the space. Being sold fully furnished and turnkey, this property is truly ready for immediate enjoyment or rental use. The Siesta Beach House community offers a community pool and direct private beach access, all within a highly desirable location. With a flexible minimum lease period of just 3 days, this property also presents excellent income-producing potential for investors seeking short-term rental opportunities. Whether you are searching for a beachside investment property, a lock-and-leave vacation home, or a cozy private condominium steps from world-renowned beaches, this Siesta Key opportunity delivers exceptional lifestyle and value in one of Sarasota’s most sought-after coastal destinations. Schedule your private showing today and experience the island lifestyle firsthand.

5950 Midnight Pass Road Unit 101, Sarasota
6157 Midnight Pass Road Unit E53, Sarasota
$449,000
2 Beds ⋅ 2 Baths ⋅ Siesta Plat SubDv. ⋅ 34242 Zip Code
Experience the best of island living in this inviting third-floor condo located in the sought-after Bay Oaks community on Siesta Key. Spanning 1,101 square feet, this two-bedroom, two-bathroom residence offers a seamless blend of comfort and convenience, with elevator access making every arrival effortless. The interior is bright and welcoming, designed with both relaxation and functionality in mind. The kitchen has stone counter tops with tile backsplash. Ceramic tile covers the floor throughout. The primary bedroom serves as a private retreat, featuring an en-suite bathroom with a spacious walk-in shower and large walk-in closet. The second bedroom is equally well-appointed, with easy access to the second bathroom which boasts a large whirlpool tub and shower—perfect for unwinding after a day in the sun. Throughout the condo, you’ll find plenty of storage options, ensuring a tidy and organized living space. Large living room and dining area add to this comfort as well as the screened in balcony overlooking the pool. Besides the large, heated community pool, Bay Oaks also provides, tennis courts, a community room with pool table & a waterfront park like setting with a BBQ area. Nature enthusiasts will appreciate the private fishing pier situated right on the Intracoastal Waterway at the rear of the complex—a perfect spot to watch the morning light dance on the water. It’s the lifestyle outside your door that truly shines. When you're ready for the sand, the world-famous beach of Siesta Key is easily accessible nearby. A free island trolley is accessible at street side in front of the condominium that will take you to one end of the Island to the other to enjoy, Turtle Beach, South Village Amenities, the public beach with lifeguards and the famous Siesta Village. This property isn't just a beautiful retreat; it’s a proven performer with a strong rental track record. For an investor or a savvy buyer, the transition could not be simpler. The condo is being sold fully turnkey furnished, meaning it comes with everything needed to hit the ground running. It is completely ready for immediate renters the moment you close. The timing couldn't be better—the unit is already booked for January, February, and March. If you close by the end of the year, you’ll step into immediate ownership with three months of rental income already booked. Whether you are looking for a lucrative investment or a seasonal getaway or your new home, this condo places you in the heart of everything that makes Siesta Key a premier destination. Come see why life is better when you’re surrounded by the beauty of the Bay and the Gulf.

6157 Midnight Pass Road Unit E53, Sarasota
6703 Midnight Pass Road Unit 101, Sarasota
$400,000
2 Beds ⋅ 2 Baths ⋅ Sea Winds SubDv. ⋅ 34242 Zip Code
Picture a full day on Siesta Key without ever touching your car keys. Coffee from Crescent Beach Market. Breakfast at Toasted Mango Café. A few hours on the soft white sand of Crescent Beach, then a walk down the shoreline to Point of Rocks, known for the best snorkeling on the key. Rent a boat at the marina by the Stickney Point bridge, watch the sun drop into the Gulf, and finish the night under the thatched roofs at Captain Curt’s with a cold drink in your hand. Want to go farther? The trolley stops right in front of the building. All of it starts at the front door of Unit 101 at Sea Winds. And when you are not here, it can be working for you. The condo comes fully furnished, down to the beach chairs, towels, and cart, it sleeps seven, and Sea Winds allows leases as short as 2 weeks, with the board reviewing a change to 1 week. Turnkey on day one, whether day one is your vacation or a renter’s. The owner even has prospective renters on standby. Then there is the patio. Unit 101 is the ground floor end unit, and it has the largest fenced patio at Sea Winds, shaded by its own tree, lined with hanging flower baskets, with a grill and a table for six that tends to stay set long after dinner is done. Slide the door open and the living room and patio become one space. No elevator, no long hallway, and your parking space is painted right outside the front door. Sea Winds is the kind of community where neighbors still get together in the clubhouse for games. The heated pool was rebuilt in 2025, the roof was replaced in 2024, the underground pipes and parking lot were redone in 2026, and the A/C is from 2022, so the big projects are already behind it. The $973 monthly fee covers cable, water, sewer, landscaping, and building maintenance, so there is nothing to manage while you are away. There is more to love here than fits in a description. Reach out to the listing agent for the full feature sheet, including the rental details, or to schedule your private showing.

6703 Midnight Pass Road Unit 101, Sarasota
8911 Midnight Pass Road Unit 511, Sarasota
$385,000
1 Beds ⋅ 1 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code
TOP-FLOOR COASTAL LIVING WITH BREATHTAKING VIEWS OF THE INTRACOASTAL WATERWAY AND THE GULF OF MEXICO! Experience the best of Siesta Key living from this exceptional, turnkey furnished one-bedroom, one-bath residence in desirable Sunrise Cove. Enjoy the rare opportunity to take in spectacular sunrises over Sarasota Bay and magnificent sunsets over the Gulf of Mexico, all from your top-floor coastal retreat! With stunning water views in both directions, sparkling blue waters, and passing boats, every day feels like a vacation in paradise. The bright, inviting interior flows seamlessly into a Florida room where sweeping Intracoastal views take center stage. A built-in Murphy bed provides additional sleeping accommodations for family and guests, while the spacious primary bedroom features a generous walk-in closet. An updated bathroom and turnkey furnishings make this beautiful condo ready for immediate enjoyment. RESORT-STYLE LIVING AT SUNRISE COVE! Enjoy two heated swimming pools, tennis and pickleball courts, a fitness center, game room, and waterfront docks available to lease for a nominal fee on a first-come, first-served basis. Recent community improvements include new roofs, docks, and carports. LOCATION, LOCATION, LOCATION! Perfectly situated directly across from Turtle Beach and just steps from waterfront dining at Ophelia's on the Bay and Turtles on the Bay. The complimentary Siesta Key Breeze trolley offers convenient access to the charming boutiques, restaurants, and entertainment of Siesta Key Village. On-site management and a 30-day minimum rental policy provide added flexibility for seasonal owners and rental opportunities. Whether you're searching for a seasonal escape, investment opportunity, or year-round residence, this top-floor gem offers an exceptional combination of dual water views, resort-style amenities, and an unbeatable Siesta Key location. Discover the coastal lifestyle you've been dreaming of! Your little piece of paradise awaits!

8911 Midnight Pass Road Unit 511, Sarasota
5830 Midnight Pass Road Unit 8, Sarasota
$429,000
1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
BEACH LOVERS AND INVESTORS, THIS ONE IS ALL ABOUT THE LOCATION! Welcome to Unit 8 at Jamaica Royale on Siesta Key, where being close to the beach doesn't get much better! Just steps from the world-famous Siesta Key Beach, this is one of the closest villas to the sand, making it easy to spend your days enjoying the Gulf's turquoise waters. Even better, the pool is right off your back patio, putting two of the most sought-after vacation amenities just outside your door! This prime location is a major draw for renters looking for the ultimate beach getaway. Thoughtfully renovated and designed to maximize comfort and functionality, this studio features a fresh coastal theme, luxury vinyl plank flooring, quartz countertops, and soft-close cabinetry. The inviting interior includes a Murphy-style bed, comfortable leather sofa, and dining for four. Offered turnkey furnished, it's ready for you to enjoy or begin generating rental income. Weekly rentals are permitted, and owners have the flexibility to use the onsite rental company or choose their own rental management. Even better, owners may have up to two pets! Beyond your villa, Jamaica Royale welcomes you with beautifully maintained grounds, lush tropical landscaping, private deeded beach access, and three resort-style pools. A nearby stop for the Siesta Key trolley makes it easy to explore Siesta Key Village, with its charming boutiques, local restaurants, and lively entertainment. Whether you're searching for a personal beach escape, a vacation rental investment, or the best of both worlds, this is your opportunity to own a slice of paradise in a location that truly stands out!

5830 Midnight Pass Road Unit 8, Sarasota
6006 Midnight Pass Road Unit 11, Sarasota
$449,000
1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code
Your opportunity to own a piece of Siesta Key at an exceptional value, with nearly 200 feet of deeded beach frontage! Priced as the lowest-priced true 1-bedroom condo on Siesta Key, this charming, TURNKEY furnished 1-bedroom, 1-bath unit at Casa Mar features two additional sleeper sofas and has been refreshed by the new owners. Whether you’re searching for a personal beach retreat, a seasonal escape, or an income-producing vacation rental, this is your chance to own a slice of paradise! Walk to Siesta Key’s world-famous white quartz sand beaches and the turquoise waters of the Gulf of Mexico from this inviting beachside condo offering 600 square feet of interior living space, a 108-square-foot screened lanai, and a brand-new outdoor paver patio currently being completed. The new patio will provide an adorable additional space for outdoor seating, relaxing, and enjoying the island breeze. Inside, vintage island character meets relaxed coastal living, with freshly painted vaulted wood-beamed ceilings, timeless terrazzo flooring, abundant natural light, and an open living area that flows seamlessly to the screened lanai. It’s the perfect spot for morning coffee or unwinding after a day at the beach. The kitchen features solid-surface countertops, an eat-in dining area, and an open connection to the main living space. The spacious bedroom offers ample storage, including built-in closet cabinetry, while the bathroom features a walk-in shower. Recent improvements include a new A/C in 2025, a new building roof in 2024, a water heater replaced in 2021, updated bathroom plumbing, and partial impact windows. An assigned covered carport is conveniently located directly outside the private ground-floor entrance, making access effortless with no stairs to navigate. Casa Mar delivers the Siesta Key lifestyle buyers dream of, with private deeded beach frontage, two covered beach pavilions, two community pools, tennis and pickleball courts, basketball, a clubhouse, four BBQ grilling areas with picnic tables, and community laundry facilities. The condo fee includes cable TV, internet, water and sewer, building insurance, and grounds maintenance. Getting around the island is easy, too! The Siesta Key Breeze Trolley stops right at the Casa Mar entrance on Midnight Pass Road, offering convenient transportation to Siesta Key Village for dining, shopping, and nightlife, or south to Turtle Beach. With exceptional amenities, weekly rentals permitted, and the flexibility to enjoy it yourself or generate rental income, this TURNKEY beach getaway offers the best of island living. Don’t miss this opportunity to own your own piece of paradise on Siesta Key!

6006 Midnight Pass Road Unit 11, Sarasota
1300 N Portofino Drive Unit 105, Sarasota
$399,900
1 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
YOU DESERVE PARADISE! MOVE RIGHT IN TO THIS PRISTINE DOLLHOUSE! BEACH ACCESS! BOATING! PERECT ONE BEDROOM WITH 2 FULL BATHS! GRANITE COUNTERTOPS, TOP OF THE LINE SHOWER ENCLOSURE, IMPACT/HURRICANE WINDOWS!! THIS HAS IT ALL!, WALK RIGHT OUT FROM YOUR LANAI TO YOUR BOAT DOCK, HEATING SWIMMING POOL, HOT TUB, SAUNA, SHUFFLEBOARD, DOCK ON THE INTRACOASTAL FOR MEETING WITH YOUR FRIENDS, FISHING OR JUST RELAXING! SIESTA HARBOR IS IN A PRIME LOCATION ON THE KEY, WALKING DISTANCE TO SHOPS, RESTAURANTS, CATCH THE TROLLEY RIGHT OUTSIDE YOUR DOOR, BEACH ACCESS RIGHT ACROSS THE STREET TO BEAUTIFUL SIESTA KEY BEACH WITH QUARTZ CRYSTAL SAND! THIS UNIT IS HOME OR A RENTAL, UP TO YOU! MOVE RIGHT IN, NEW HVAC, TILE FLOORS, CROWN MOLDING, PLANTATION SHUTTERS, FULL GLASS ENCLOSURE ON THE LANAI THAT BRINGS IN THE SUNSHINE, WATCH THE DOLPHINS, BOATING.. EVERYTHING UPGRADED WITH THOUGHT, NO POPCORN ON THE CEILINGS, ALL REDONE! ALL UNDER $400,000! YOU DESERVE PARADISE!

1300 N Portofino Drive Unit 105, Sarasota
5673 Midnight Pass Road Unit 202, Sarasota
$479,999
2 Beds ⋅ 2 Baths ⋅ White Sands Village SubDv. ⋅ 34242 Zip Code
Welcome to Paradise! White Sands Village is great property that is located directly across from the world- famous beautiful Siesta Key beach! It is a great investment or your own private island retreat. This 2bedroom 2 bath well maintained condo is turnkey. Pet friendly, furnished coastal getaway. The large primary suite has an en-suite bath with extra closet space great for full-time living or income producing vacation rental. The guest bedroom has twin beds as well as air mattresses to accommodate many guests. Plenty of guest parking this unit has 1 covered parking space available. Heated community pool, club house sauna, BBQ grills as well a boat dock available for fishing.

5673 Midnight Pass Road Unit 202, Sarasota
116 Vista Hermosa Circle Unit 108C, Sarasota
$400,000
2 Beds ⋅ 2 Baths ⋅ Vista Hermosa SubDv. ⋅ 34242 Zip Code
Your Siesta Key Lifestyle Awaits — The Time to Own Is Now! Welcome to one of Sarasota’s most sought-after coastal destinations, where the beauty of Siesta Key is right outside your door. This completely updated ground-floor residence captures the true essence of coastal living with a soft, neutral palette and a relaxed, welcoming atmosphere. This property sets itself apart from all the others—it makes you feel right at home at the beach the minute you arrive. The spacious bedrooms provide plenty of room for family and guests, with the oversized guest bedroom large enough to accommodate two full-size beds, comfortably sleeping four. The beautifully refreshed kitchen features new appliances, quartz countertops, updated cabinetry, and a new tile backsplash that perfectly complements the home’s coastal-inspired design. Extend your enjoyment outdoors in the enclosed lanai, offering privacy and a comfortable space to enjoy year-round. There is also the possibility of adding a paver extension to the lanai, creating even more outdoor living space for relaxing and entertaining. A convenient in-unit laundry closet with washer and dryer adds to the ease of everyday living, while storm windows and doors provide added peace of mind. And then there’s the lifestyle! Spend your days enjoying the world-famous sands of Siesta Key Beach, explore the beauty of Selby Gardens, shop and dine at St. Armands Circle, or head into downtown Sarasota for its incredible restaurants, arts, culture, and waterfront attractions. And don’t miss one of the area’s most anticipated fall events—the Siesta Key Crystal Classic Sand Sculpting Festival. Come be part of the fun, experience the incredible artistry, and enjoy yet another reason why life on Siesta Key is so special. The time is now to make this coastal retreat your own and be ready for the 2027 season. Whether you’re looking for a full-time residence, a beach escape, or your own piece of the Siesta Key lifestyle, this beautifully updated home offers something truly special. Come see for yourself why this one feels different. Your beach lifestyle begins the minute you arrive.

116 Vista Hermosa Circle Unit 108C, Sarasota
6157 Midnight Pass Road Unit G11, Sarasota
$399,000
2 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
Enjoy easy island living in this beautifully maintained first-floor condominium at Bay Oaks on Siesta Key. With your assigned carport just steps from the front door, there's no need to wait for elevators, making everyday living and guest arrivals effortless. This versatile one-bedroom residence features a converted den that functions as a second bedroom, allowing the property to be successfully marketed and rented as a two-bedroom vacation rental. A favorite among returning guests, this turnkey-furnished unit offers an excellent opportunity for personal enjoyment or investment income. Inside, ceramic tile flooring flows throughout the living and dining areas, while the flexible floor plan comfortably accommodates family and visitors. Step outside to a private patio surrounded by mature trees, providing a peaceful retreat and convenient rear access to the community's resort-style amenities. Residents and guests enjoy Bay Oaks' impressive amenities, including a heated pool, tennis courts, fishing dock, social room, and outdoor grilling areas. Located directly on the free Siesta Key trolley route, you'll have easy access to world-famous Siesta Beach and the shops, dining, and entertainment of Siesta Key Village. Bay Oaks permits one-week rentals, making this a highly desirable and consistently popular rental property. Sold turnkey furnished, this island getaway is ready for immediate enjoyment or rental income from day one.

6157 Midnight Pass Road Unit G11, Sarasota
1300 N Portofino Drive Unit 103, Sarasota
$449,500
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
Welcome to your own piece of paradise on world renowned Siesta Key! This beautifully updated and freshly painted 2 bedroom, 2 bathroom residence in the highly desirable Siesta Harbor 55+ community is clean, bright, inviting, and ready for its next owner. Just steps from the soft, powdery sands of Siesta Beach, this is the perfect opportunity to enjoy the laid back island lifestyle you've been dreaming about. From the moment you walk in, you'll appreciate the fresh coastal feel and thoughtful updates throughout. The residence features beautiful luxury vinyl flooring, a renovated kitchen, updated bathrooms, a brand-new vanity in the guest bath, and new and newer appliances. The open and comfortable floor plan is filled with natural light and designed for easy everyday living. Adding even more peace of mind, a brand new air conditioning system was installed in October 2026, so the next owner can enjoy the comfort of a brand-new system from day one. One of the true highlights is the spacious all season's lanai, where you can sit back, relax, and take in the fantastic waterfront views. Watch boats cruise along the shimmering saltwater canal as you enjoy your morning coffee or unwind with a glass of wine in the evening. The canal leads directly to the Intracoastal Waterway and Gulf of Mexico, creating a beautiful backdrop and a constant reminder that you are living on Siesta Key. Siesta Harbor is an active and welcoming 55+ community with an incredible selection of amenities and activities. Enjoy the heated pool and spa, fitness center, sauna, clubhouse, shuffleboard courts, private Intracoastal pier, and a wonderful social calendar filled with community events and activities. Fishing enthusiasts will love the private waterfront pier, while boaters have the opportunity to lease dock space on a first come, first served basis. Residents also enjoy deeded beach access through Crescent Arms, beautifully maintained tropical grounds, on site management, private storage, and same floor laundry. With the free trolley stop conveniently located just outside the community, Siesta Key Village, local shops, restaurants, and entertainment are all easily accessible. The South Bridge provides convenient access to mainland Sarasota, downtown, and the area's many cultural attractions. Whether you're looking for a full-time home, a seasonal escape, or your own island retreat, this residence offers an incredible combination of location, thoughtful updates, waterfront views, amenities, and lifestyle. With the brand-new air-conditioning system, freshly painted interior, updated kitchen and baths, and beautiful waterfront setting, so much has already been taken care of for you. Just move in, relax and enjoy everything Siesta Key has to offer. Come see why life is better on the Key!

1300 N Portofino Drive Unit 103, Sarasota
9034 Midnight Pass Road Unit 6, Sarasota
$399,000
2 Beds ⋅ 2 Baths ⋅ Cozy Cove SubDv. ⋅ 34242 Zip Code
Opportunity knocks on Siesta Key at $399,000, and the seller is paying your first six months of association fees.Located within Cozy Cove, an intimate six-residence waterfront community on the quiet southern end of the island, this 2-bedroom, 2-bath single-level condominium offers a compelling entry point for the buyer ready to create something of their own. The residence is clean and functional today, but its largely original interior presents the opportunity for a full renovation and repositioning. Buy now, renovate through the off-season, and have it ready for Season 2027, whether your strategy is vacation rental, resale, or simply creating your own Siesta Key getaway. Cozy Cove offers weekly rentals, a waterfront pool, brand-new docks along Blind Pass, and even a glimpse of the Intracoastal from the residence, all just minutes from Turtle Beach. Whether the plan is to hold, rent, renovate and resell, or some combination of the three, opportunities to enter Siesta Key at this price point are increasingly hard to find.

9034 Midnight Pass Road Unit 6, Sarasota
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