Siesta Key FL Recently Sold Homes

3 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer | BEACH VIBES? Check, PRIME LOCATION? Check, HIGH END RENOVATIONS all completed in 2025? Check, check & check! Welcome to the ultimate in Florida living – whether you are looking to settle in full time or score an amazing SHORT TERM RENTAL/VACATION HOME, this one is a MUST SEE! Located in the heart of Siesta Key, this single story POOL HOME puts you just a 10 minute stroll to Siesta Key Village, and 5 minutes past that you are on the powdery sands of the world-famous beach. Nestled in a quiet, tree lined, no HOA community, you are living large with easy access to US-41, SR-72, and I-75. It’s the best of laid back island living with every modern convenience at your fingertips! Looking for CURB APPEAL? It’s through the ROOF (which was replaced in 2020)! With lush tropical landscaping, a circular paver driveway, covered portico, and an EV CHARGING STATION, the tone is set before you ever step inside. The covered front entry features a charming glass-inset front door that opens into an adorable foyer with immediate beach house energy. Inside you will find porcelain WOOD LOOK TILE FLOORS throughout and a living area full of personality – think vaulted TONGUE & GROOVE WOOD SLAT/BEAM CEILINGS, a cozy WOOD BURNING FIREPLACE, and CUSTOM BUILT-INS! You will appreciate the seamless flow into the light filled dining area, where sliding glass doors paired with a large window connects the interior to your outdoor oasis and includes a built-in bar and extra storage. The kitchen is a showstopper – a 2025 renovation with on trend TWO-TONE CABINETRY, stylish TILED BACKSPLASH set in a modern herringbone pattern, sleek QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, and a window over the sink so you don’t miss a second of the party outside. Enjoy idyllic indoor/outdoor living with a COVERED LANAI and the recently resurfaced SALT WATER POOL, complete with ceiling fans and new screens in the enclosure for maximum comfort, and convenient outdoor/pool bath access. The fenced backyard is both low maintenance and private – perfect for soaking up the Siesta Key sunshine! Last but certainly not least, your PRIMARY SUITE is a peaceful hideaway with a huge WALK-IN CLOSET, French door access to the lanai, and a spa-like en-suite bath featuring DUAL SINKS under LIGHTED MIRRORS, and a custom tiled walk-in shower behind seamless glass. Need space for guests, a home office or additional rental potential? The PRIVATE MOTHER-IN-LAW-SUITE is a game changer - delivering its own entrance off the pool area for endless versatility with additional pavered parking close by. Also take note of the NEWER A/C, UPDATED PLUMBING & WATER HEATER (2025), partial ELECTRICAL UPDATES, IMPACT GLASS/DOUBLE PANE STORM WINDOWS (most under 5 years old), and extra storage cabinets in the garage – to sum up Saint Albans Ave… The vibe? Fresh, modern and full of character! The location? Out of this world! The lifestyle? Pure Siesta Key magic! Call today!

5108 Saint Albans Avenue, Siesta Key

$335,000

1 Beds ⋅ 1 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code

WATERFRONT LUXURY ON SIESTA KEY Spacious 1-Bedroom Condo with Panoramic Bay Views Experience the best of coastal living in this beautifully appointed one-bedroom, one-bathroom condo, ideally situated on the Intracoastal Waterway in the sought-after Sunrise Cove community. This rare waterfront offering features unobstructed views of Little Sarasota Bay and a veiw of the Gulf of Mexico from the front of the unit—a truly unique find on Siesta Key. Whether you're seeking a full-time residence, a seasonal escape, or an income-generating investment, this property delivers exceptional flexibility. With an on-site rental manager, owners can rent the unit during peak season (rental rates for 1-bedrooms range from $6,000–$7,000/month) and enjoy personal use during the off-season, helping to offset ownership costs. Interior Highlights: Bright, open floor plan Large enclosed lanai with panoramic bay views Perfect space for enjoying morning sunrises and daily waterfront activity Community Amenities Include: Two resort-style waterfront pools Fully equipped modern fitness center Bayside BBQ grills and picnic areas for entertaining Tennis and pickleball courts Kayak and bicycle storage Boat slips with water and electric—ideal for boaters or guests Covered assigned parking plus ample guest parking Unlimited use of laundry facilities—conveniently located just outside the unit Recent updates to the roof, carports, and seawall ensure peace of mind and long-term value. Prime Location: Steps from Turtle Beach Park with kayak/boat launches, playground, and beach access Adjacent to Turtles Restaurant and just minutes from Siesta Key Village with shopping, dining, and nightlife Easy access via the free Siesta Key trolley This residence offers an exceptional location, lifestyle, and investment potential blend. Don’t miss your chance to own a piece of paradise on Siesta Key.

8977 Midnight Pass Road Unit 521, Sarasota

$1,200,000

2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code

The Gulf & Bay Club on Siesta Key is, by its own definition: exclusive, elegant and engaging. A gated 32-acre community with unrivaled waterfrontage and amenities, this is not your typical beach front condo, this is unparalleled resort living on Siesta Key. In this premium community, building F is ostensibly the prime location with sprawling views of the white sands of Crescent beach that gently fade under lapping waves into the crystal-clear waters of the Gulf. Spacious and turnkey furnished, this bright unit offers just under 1,500 square feet of living space and an open concept that allows you to move and converse freely throughout. A kitchen outfitted with ample storage also offers an informal dinette while the dining area still boasts seating for 8. The comfortable living space, adjacent to the integrated lanai, will keep you comfortable while you gaze upon the coveted, unobstructed horizon view. Retreat to your owner’s suite with generous space and more captivating panorama. Guests will be comfortable in the additional bedroom and full bath while laundry and closet space benefit your organized routine. A dedicated, covered parking space is an added bonus. Meander along the footpaths through the meticulously manicured courtyard with a freshwater lake and fountain features, an island situated in a lagoon, and three heated swimming pools. Take advantage of any number of organized events, cultural outings or recreation happenings at the two clubhouses with pool tables, tennis, pickleball, racquetball and basketball courts, media facilities and print/video libraries. Stay active and feel your best at the commercial grade fitness center, hot tub and dry saunas. Driving electric? Gulf & Bay is one of only two communities on the island offering charging stations! You simply must visit to fully understand just how much is offered at the Gulf & Bay Club, where you can create your own adventure from sunrise to sunset along the award winning Crescent Beach on Siesta Key!

5740 Midnight Pass Road Unit 402, Sarasota

$600,000

2 Beds ⋅ 2 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code

Existing home has been mitigated for water damage. One of the best values on Siesta Key. Photos of the existing home are prior to the 2024 storm damage. Large lot at over 10,880 SF Right by Out of Door Academy and walking distance to beach and Siesta Village. Attention Veterans! It may be possible for qualifying veterans to assume a huge part of the purchase price in the form of a 2.85% VA loan. *VA approval process required* Last photo of new build home and floorplan are an example only that could be built on this lot by Cannon Homes. Current List price DOES NOT include this home but is only shown for example purposes of home that would fit on this lot** Separate pricing for this new build is available if desired.

4522 Banan Place, Sarasota

$630,000

2 Beds ⋅ 2 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code

New build or restoration opportunity!! This unique two-bedroom, two bathroom, three car garage bungalow is nestled in the heart of Siesta Key. Located minutes away from, world famous Siesta Key beach and the village; it is perfectly situated to live the island life. Unfortunately, the house was flooded during Helene and has been stripped down and is ready for its new owners. Remodel the house or start over either way you will be please to know that the three car garage was built in 2015 and can be incorporated into either option. Plans for the garage addition, survey and recent appraisal are available for review. House is being sold "As Is." Don't miss out on this once-in-a-lifetime opportunity to own your slice of paradise.

633 Calle De Peru, Sarasota

$1,150,000

2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code

Gulf-front living at its finest in the exclusive Gulf & Bay Club on Siesta Key! This updated 2BD/2BA condo offers breathtaking, unobstructed views of the Gulf and Siesta Key Beach with their stunning nightly sunsets. The open layout features a modern kitchen with granite counters and white contemporary cabinetry. A spacious living/dining area that opens to a private beachfront balcony. The primary suite boasts Gulf views, balcony access, walk-in closet, and en-suite bath. Gulf & Bay Club is a gated, resort-style community with 800’ of private beach, 3 pools, 8 tennis courts, pickleball, fitness center, 2 clubhouses, saunas, grills, and more. On-site rental management with 1-month minimum rentals. A rare opportunity for luxury coastal living or investment!

5790 Midnight Pass Road Unit 702, Sarasota

$1,100,000

2 Beds ⋅ 2 Baths ⋅ Siesta Breakers SubDv. ⋅ 34242 Zip Code

Step into this beautifully refreshed 2-bedroom, 2-bathroom condo offering 1,285 sq ft of upscale comfort with breathtaking views of the Gulf of Mexico. Nearly every feature is under three years old—including stylish furnishings, bedroom carpet, fresh interior paint, a modern master shower, washer and dryer, refrigerator, and a brand-new AC installed in April 2025. Located on the desirable Siesta Key, this unit combines comfort, style, and breathtaking beauty. The bright, open layout features neutral tile floors throughout the main living areas, with plush carpeting in the bedrooms. The spacious living room opens to a private patio, perfect for enjoying the panoramic Gulf views. The well-equipped kitchen boasts ample wood cabinetry, a peninsula island with an eat-in breakfast bar, and appliances, including a full-size refrigerator, range, microwave, and dishwasher. The master suite is a peaceful retreat with sliding doors leading to the patio and Gulf views. It includes a king-sized bed, lounging chair, and two walk-in closets. The ensuite bathroom offers double sinks and a large shower. The guest bedroom, with two twin beds, provides a cozy space with easy access to the second full bath featuring a tub/shower combination. Additional conveniences include an in-unit washer and dryer, along with window treatments and a dedicated entryway. Fully turnkey furnished, this condo is ready for you to move in or rent out. Siesta Breakers offers an exceptional array of amenities for its owners and tenants. The property features a private, gated beach access, so you can step out from your unit directly to the soft, powdery sands of Siesta Key’s world-famous beach. The heated community pool is perfect for relaxing or swimming laps, with plenty of outdoor seating and a private air-conditioned clubhouse that includes a small library, tables for socializing or playing games, and a comfortable atmosphere for gathering with neighbors. For those who enjoy a more active lifestyle, the community offers on-site tennis and pickleball courts, and the HOA maintains the grounds to ensure they are always beautiful. Parking is a breeze with a dedicated, covered carport space, as well as guest parking available for your visitors. An on-site manager makes it easy to rent out your unit for additional income, with a minimum one-week rental policy, allowing you to capitalize on the popularity of Siesta Key as a vacation destination. Whether you use the on-site management or choose to self-manage the rentals, this property is an excellent income-producing opportunity. In 2024, it generated over $84,000 in rental income, and solid bookings are already in place well into 2026, making it a great investment. Just steps from the beach, Siesta Breakers is also within walking distance to shopping, dining, and local markets, offering the best of island living. With easy access to Sarasota-Bradenton International Airport, travel is a breeze. Whether you’re looking for a second home, vacation rental, or full-time residence, this condo offers the ultimate Siesta Key lifestyle with income potential, luxury, and unbeatable Gulf views.

6480 Midnight Pass Road Unit 315, Sarasota

$920,000

5 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code

Lovingly owned for 20 years, this tropical retreat offers privacy, charm, and thoughtful updates throughout. Recent enhancements include lush Areca palms for a private, resort-style setting, and an expanded pool area complete with a cozy seating space, large umbrella, and fire pit-perfect for relaxing or entertaining under the stars. Nestled in the heart of Siesta Key, and close to one of the best beaches in the U.S., this spacious 5-bedroom, 3.5 bathroom home offers a perfect blend of comfort, style, and functionality. Featuring engineered hardwood floors throughout, this residence is designed for family living and entertaining. The living room flows seamlessly into the dining room, which is conveniently located next to the kitchen. The kitchen features shaker style cabinetry and Corian counters. A pass-through window and breakfast bar open to the casual dining area, which can easily be transformed into a game room or flex space to suit your needs. On the other side of the of the kitchen is the spacious family room, with soaring vaulted ceilings and fireplace. A French door from the family room leads to the open pool area. A fiberglass salt water pool was added in 2008 with a travertine deck. The spacious Primary bedroom suite includes a sitting area with large window that offers serene views, an adjoining library/office that allows for work from home with floor to ceiling bookshelves with a separate exterior door. A major renovation in 2014 added two additional upstairs bedrooms bringing the total to four, plus a half bath with a charming turquoise/green tile display on the mirrored wall. The full bath upstairs has Quartz counters, shaker cabinets, double sinks, and skylight in the shower giving the space an abundance of natural light. The home is built for durability with a metal roof, hurricane impact windows upstairs, and many downstairs, with custom hurricane Fabric shields protecting non-impact windows and doors. The 10’ elevation has kept the property free from hurricane damage. The home is ideally situated a short distance from Glebe Park, one of Siesta Key’s hidden gems. Perfect for families and active lifestyles, the park features a baseball field, basketball court, multi-purpose field(great for soccer or casual games), pickleball court, playground, restrooms, and a gazebo for parties and picnics. The mid-island location offers easy access to both the North and South bridges.

614 Tropical Circle, Sarasota

$590,000

2 Beds ⋅ 1 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code

Siesta Key Beachfront Paradise – Rare Top-Floor Gulf View Condo! Location, location, location! This stunning 2-bedroom, 1-bathroom, 753 sq. ft. top-floor unit in La Siesta’s Building A offers unobstructed, direct Gulf views from both the private screened balcony and the spacious primary bedroom. Rarely available and highly sought after, this turn-key furnished condo is situated directly across from Siesta Key Public Beach, providing the perfect opportunity for vacation living or an income-producing rental - this is one of the few weekly rental properties on Siesta Key with on-site management. Designed for both comfort and style, this coastal-inspired retreat comfortably accommodates six guests. The primary suite features a king-size bed, walk-in closet, full dresser, and 48” wall-mounted TV, all with stunning beachfront views. The second bedroom offers a full-over-full bunk bed, dresser, walk-in closet, and 32” smart TV, while the living room provides a queen sleeper sofa, plush seating, a 55” smart TV. The fully equipped kitchen allows for home-cooked meals, but for those who prefer to explore, charming Siesta Key Village is just a short walk or free trolley ride away, offering restaurants, shops, and nightlife. La Siesta offers resort-style amenities, including a heated pool, fitness center, recreation room with pool table and ping pong, shuffleboard courts, grilling areas, laundry facilities, and assigned covered parking. The on-site full-time management team ensures easy rentals and a hassle-free experience. Whether you're looking for a dream vacation home or a high-performing rental property, this rare top-floor Gulf-view condo is an incredible opportunity—don’t miss out!

901 Beach Road Unit 402, Sarasota

$700,000

2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code

Here is your opportunity for a Gulf and Bay Bayside 2nd-floor walk-up Condo. Oh so lovely views of the pond and the water fountain, Weekly rental makes this an excellent investment. Just a short walk and you are on our famous Siesta Key Beach along with this deeded beach access there are wonderful amenities. - Two heated pools, clubhouse, BBQ area, fishing pier, pickleball and tennis courts, fitness room, and a warm welcoming community. The one-car garage and driveway parking make it all so very convenient, and on-site rental management at this Key West Style complex adds to the convenience. In move-in condition. Just a short of trolley ride to Siesta Village with all the shopping and restaurants with great nightlife. No carpet, all tile fIn

1228 Siesta Bayside Drive Unit 1228-C, Sarasota

$629,900

2 Beds ⋅ 1 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code

Rare Turnkey "PENTHOUSE OPPORTUNITY" located in one of the front buildings with a Full Gulf View directly across from the world-famous #1 rated Siesta Key Beach with beautiful quartz crystal sand! The exceptional office staff make this community well managed & this unit has a proven track record of 57K gross rental income in '2023 & 53K for '2024 & year-to-date in '25 (Jan-June) 37K which can be a great money maker for you! This condo is also used much by family when not in use! La Siesta offers 1 week minimum stays for easy rentals & has low monthly fees of only $841.67/month which make it even better! This condo is turnkey furnished with tasteful updates/furniture & has everything you need for a wonderful stay. Owner/Broker has used this condo on occasion for personal use when not rented. You'll love the nightly variety of sunsets from your screened balcony & you will feel the energy being right across the street from this world-renowned beach! Many upgrades in '22 including some of the following: A/C*most furniture & accessories*quartz tops*vinyl flooring*carpet & padding*fresh paint*balcony rescreened*plantation shutters/blinds*lanai rescreened '24 & more. The trolley stop is located right in front & is more than just a convenience ... it will connect you to fine restaurants~shopping~nightlife/entertainment in the vibrant village & throughout the key. This complex is perfectly positioned & is nestled amidst everything you could want or need. The helpful & dedicated staff will also accommodate your requests. For outside activities, La Siesta offers a heated pool, shuffleboard, cornhole & BBQ grills on-site. Unit owners may have 1 small pet under 25 lbs. with board approval. Elevator access & Laundry on the same floor make it easy. Hurry on this one & enjoy it in between tenants before the busy winter season (this unit fully rented throughout season) & secure your own piece of paradise today. Don't miss out on this exceptional investment opportunity. Being sold as is with the right to inspect. All showings require confirmation in case a tenant is in place during that time.

925 Beach Road Unit 408, Sarasota

$650,000

3 Beds ⋅ 2 Baths ⋅ Waterside East SubDv. ⋅ 34242 Zip Code

Imagine living in your dream home on world renowned Siesta Key…. THIS PROPERTY IS BEING SOLD FOR LAND VALUE ONLY!!! The cul-de-sac location offers privacy with no homes across the street. Live the local’s lifestyle in Waterside East, an established community with very little rental traffic. Easy access to the north and south bridges. The current home on the property has a footprint of 3,173 square feet. The tile roof 2018 and A/C 2021, condition unknown since the recent hurricanes. 2 feet of drywall was removed immediately after Helene. Windows were scheduled to be installed prior to the storms, they are in the garage if a buyer wants to renovate the home, no sliders. Property is being offered as-is. You can bring your own builder but E/M Custom Homes is the sellers preferred contractor. Or…..This is your chance to collaborate with E/M Custom Homes, renowned for their impeccable craftsmanship and modern coastal design, to create a one-of-a-kind residence tailored to your lifestyle. A thoughtfully designed Coastal Contemporary home plan has been situated on the lot offering 2,750 sq. ft. of luxurious indoor living space, with a total of 3,467 sq. ft. of indoor/outdoor space perfect for enjoying Florida’s year-round sunshine. Features of this stunning home include, Gourmet Kitchen with custom cabinetry, luxury appliances, and a walk-in pantry—ideal for both casual meals and gourmet entertaining. An open-concept floor plan filled with natural light, seamlessly connecting the kitchen, dining area, and great room. 4 spacious bedrooms and 3.5 bathrooms, providing plenty of room for family and guests. A first-floor Master Suite with a spa-inspired ensuite bath and a large walk-in closet—your private retreat. A second-floor balcony for enjoying views and relaxing in the breeze. An outdoor kitchen on the expansive covered lanai, perfect for alfresco dining. A beautiful custom designed private pool to enhance your outdoor living experience. An oversized 2-car garage and a convenient Laundry/Mudroom for everyday functionality and convenience. Don’t miss this rare opportunity to design a home that reflects your vision in a tropical paradise. Build your coastal dream home today!

670 Venice Lane, Sarasota

$680,000

2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code

Welcome to Peppertree Bay, one of Siesta Key’s most coveted Gulf to Bay communities, where island living meets effortless elegance. This turnkey, beautifully reimagined 2 bedroom, 2 bathroom residence is nestled within the desirable midrise building on the beach side of the complex, offering the perfect combination of privacy, convenience, and resort style amenities. Just steps from Siesta Key’s world renowned quartz sand, this home embodies the island lifestyle. From the moment you enter, you’ll be captivated by the peaceful view of the tranquil pond and fountain, setting the tone for relaxation. This updated unit has been thoughtfully redone, showcasing a spacious open concept floor plan that seamlessly blends form and function. The gourmet kitchen is a showstopper, featuring granite countertops, stainless steel appliances, soft close cabinetry, and a breakfast bar perfect for casual dining or entertaining. Elegant ceiling fans and updated fixtures enhance the coastal vibe, while the dining and living areas flow together effortlessly, creating a bright and inviting space for family gatherings or quiet evenings. The primary suite is a serene retreat with a walk in closet and ensuite bath, and the guest bedroom provides a comfortable haven for visitors. With a strong rental history, this property is as appealing to investors as it is to those seeking a full time residence or seasonal escape. At Peppertree Bay, residents enjoy private deeded beach access, two heated swimming pools, tennis courts, a fitness center, clubhouse, fishing pier, and professional onsite management. Covered parking and extra storage add convenience to this lock and leave lifestyle. Situated close to Siesta Key Village, eclectic dining, boutique shopping, and vibrant cultural experiences, this home truly offers it all. Whether you are looking for an income producing investment, a sun soaked seasonal retreat, or a luxurious full time residence, this residence at Peppertree Bay delivers the very best of Siesta Key living.

1055 W Peppertree Drive Unit 106AA, Sarasota

$1,700,000

3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code

Designer waterfront retreat on Siesta Key. Welcome to your dream coastal getaway! Tucked away on a quiet cul-de-sac, just moments from the world-renowned, powdery quartz sands of Siesta Beach, this impeccably renovated and landscaped waterfront home captures the essence of laid-back luxury and island living. Boaters will delight in the deepwater Grand Canal access—just one fixed bridge to Sarasota Bay and the Intracoastal Waterway, with direct Gulf of Mexico access. This fabulous single-level, three-bedroom, two-bath residence offers an open and airy floor plan filled with natural light, making it ideal for both full-time residence and an exceptional vacation retreat. A stunning 2023 designer renovation has infused the home with texture, warmth, and playful sophistication. From natural materials and artistic wallpaper to colorful accents and layered finishes, every detail is thoughtfully curated. Upgrades include new flooring, kitchen, bathrooms, plumbing, lighting, electrical systems, and front and garage doors. Enter through the statement front door into a welcoming foyer that opens to the expansive living room, featuring sleek, floating built-ins. The heart of the home is the striking kitchen and dining space, featuring a custom terrazzo island, quartz counters, Wolf and Miele appliances, and handcrafted cabinetry that offers generous storage. The island’s induction cooktop, drop-down exhaust fan, and bar seating blend form and function beautifully. A dedicated bar area with a wine cooler enhances the entertaining experience. The wide plank engineered oak flooring flows throughout, uniting each space with warmth and elegance. The spacious waterfront primary suite is a serene escape, complete with a spa-inspired bath, dual sinks, and a walk-in shower with private access to the pool. A thoughtful split floor plan provides privacy for two guest bedrooms and a second full bath. Even the laundry room is a showpiece, featuring art tile, a stacked washer and dryer, a beverage cooler, and whimsical details. Additional features include remote-controlled blinds, reverse osmosis in the kitchen, impact glass doors, windows, and garage door, an air-conditioned two-car garage with a paver driveway and walkways, Leaf Guard gutters, a 2023 HVAC system, 2023 attic and exterior insulation, and a 2020 roof. Seamless indoor-outdoor living begins with sliding impact glass doors that lead to the covered lanai and an oversized paver deck. Enjoy alfresco dining by the heated saltwater pool, resurfaced and retiled in 2022 with a sun shelf and spa also added for lounging. The lush, tropically landscaped backyard is fully fenced with faux turf, a putting green, and a fenced dog run, making it ideal for relaxation or play. Boating and water activities are a breeze from your private dock with a 14,000-pound remote-controlled lift, kayak launch, and seawall (2022). Just 15 minutes to open water, you'll savor days of fishing, paddleboarding, and Gulf cruising—right from your backyard. Ideally located near Siesta Village’s charming shops and restaurants, yet just minutes from mainland amenities, top-rated schools, and vibrant downtown Sarasota. Grab your flip-flops and sunscreen; this one-of-a-kind home offers the complete island lifestyle.

1031 Contento Street, Sarasota

$400,000

2 Beds ⋅ 3 Baths ⋅ Bay Oaks SubDv. ⋅ 34242 Zip Code

PRICED FOR QUICK, AS-IS SALE - Lowest price per sq. foot condo on Island! Siesta Key Waterfront for a Great Price! TWO-STORY, 2 BEDROOMS, 3 BATHROOMS, & 1-WEEK RENTALS PERMITTED gem in the popular Bay Oaks community. This spacious condo features two oversized ensuite bedrooms, a guest half bath, and three private lanais—two of them covered, and two with stunning Intracoastal Waterway views. Sip your morning coffee or evening cocktail while watching boats drift by from your living room or lanai—paradise found! Whether you're looking for a smart investment with income potential or your own personal beach sanctuary, this is a rare opportunity to own on world-famous Siesta Key at an amazing value. Just a short walk to Crescent Beach access points #12 and #13, where you'll find the powdery white quartz sand that’s cool to the touch and consistently ranked among the best in the world. Bay Oaks offers a peaceful tropical setting, yet you're close to it all—fine dining, pubs, shopping, and fun in the sun. The free Siesta Key Breeze Trolley stops right in front of the complex, making it easy to explore the island without ever needing your car. Don't miss your chance to own this slice of island life—it’s beautiful, versatile, and priced to move!

6157 Midnight Pass Road Unit B42, Sarasota

$510,000

2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code

Rarely available end-unit condo at Sunrise Cove on Siesta Key offering breathtaking, unobstructed views of both the Bay and the Gulf. This larger end unit features more windows for added natural light and space. The kitchen has been updated with newer flooring, cabinets, and countertops, while the rest of the unit is clean and well-maintained. Unit includes one carport space and a storage unit. Enjoy two bayfront pools, boat slips (available at a low cost, first-come basis), kayak storage, tennis and pickleball courts, a fitness center, and more. Located across from Siesta Key’s Turtle Beach access and trolley stop. No flooding from the 2024 storms—solid construction and an ideal island retreat. Monthly rentals allowed.

8897 Midnight Pass Road Unit 407, Sarasota

$550,000

2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code

THE ANCHORAGE - PARADISE AWAITS: A UNIQUE CORNER CONDO WITH DEEDED ACCESS TO SIESTA KEY BEACH ....Experience coastal paradise at this stunning 2-bedroom, 2-bathroom corner condo offering three private balconies and coveted deeded access to TripAdvisor's #1 Rated Beach in the USA. This fully furnished retreat captures Florida's natural beauty through its unique double-aspect design, flooding the space with abundant sunlight and panoramic views. The thoughtfully designed open floor plan features two spacious master suites, an updated kitchen with modern appliances, convenient breakfast nook, and VIEWS —creating an expansive, luxurious feel throughout. Start each day with breathtaking sunrises, unwind on your private balcony during tranquil afternoons, and toast to spectacular Gulf sunsets each evening. Ideally situated at the gateway to Siesta Key, enjoy the convenient proximity to shopping, diverse dining options, and effortless access to the complimentary Siesta Key Village Trolley. The Anchorage, a meticulously maintained and low-density complex, enhances your lifestyle with resort-style amenities, park like grounds and offers an optional on-site rental program allowing weekly stays, making this versatile property ideal as your private Florida retreat, personal sanctuary away from the everyday, or a lucrative rental income generator with impressive return potential! Don't miss this opportunity to own your special piece of Florida paradise!

6415 Midnight Pass Rd Unit 204, Sarasota

$1,115,000

4 Beds ⋅ 5 Baths ⋅ Siesta Properties Inc SubDv. ⋅ 34242 Zip Code

Discover the potential of this property in the iconic Sanderling Club community, nestled on the desirable south end of Siesta Key. Whether you're dreaming of a new build or a restoration, this expansive lot offers endless possibilities in a prime waterfront location. The existing four-bedroom, four-and-a-half-bath residence features a two-car garage, solid block construction, durable roof, paver driveway and a pool. The interior has been stripped and is ready for your vision. While the property was affected by flooding during the hurricanes, it now presents a clean slate for creating your dream home. Located just minutes from the world-famous Siesta Key Beach and the charming village, this property is perfectly positioned to embrace island living. As part of the Sanderling Club, the only guard-gated, single-family neighborhood on Siesta Key, you’ll enjoy unparalleled privacy, luxury, and access to exclusive amenities, including private beach access, a historic clubhouse, tennis and pickleball courts and a marina. Whether you choose to refurbish or start fresh with a modern coastal retreat or a luxurious family estate, this is your chance to own a piece of paradise in one of Florida's most sought-after Gulf-front communities. Don't miss this remarkable opportunity to transform this property into your personal haven! The Sanderling Club has released renderings that envision a new era for its historic clubhouse and private waterfront setting. Potential assessments are being discussed.

7618 Midnight Pass Road, Sarasota

$1,170,000

2 Beds ⋅ 2 Baths ⋅ Crescent Arms SubDv. ⋅ 34242 Zip Code

Siesta Key Beachfront Gem - Just Like New! Welcome to your slice of paradise on world-famous Siesta Key Beach! This stunning 2 bedroom, 2 bath elevated first floor end unit offers the ultimate in coastal living with direct beach access and breathtaking Gulf views. Step into a fully remodeled interior, professionally remediated and redesigned from top to bottom--including stylish furnishings--so you can move right in or start renting immediately. Rentals in place for 2025 & 2026. Featuring impact rated windows and doors, this condo offers peace of mind and modern efficiency. The private lawn area leading straight to the sand is a rare and highly desirable feature--perfect for families, seniors, or anyone who loves easy access to the beach. Additional highlights include: 1 car covered parking, Short-term rentals allowed with excellent income history, even with personal owner usage. Rental bookings already secured through the end of 2025. Don't miss this rare opportunity to own a turn-key beachfront condo on Siesta Key with both strong investment potential and unbeatable lifestyle appeal. Paradise is calling--schedule your private showing today!

6312 Midnight Pass Road Unit 102S, Sarasota

$4,325,000

5 Beds ⋅ 6 Baths ⋅ Gulfmead Estates SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. *Located on the north end of Siesta Key, this custom-built luxury waterfront home sits on a very private lot, surrounded by lush tropical landscaping and mature coconut palms. Perfectly positioned on a coastal playground just off Big Pass, it offers deep-water access, boating convenience, and serene natural beauty. The flexible layout includes 5 en-suite bedrooms, an elevator to all three levels, and a spacious main-level suite ideal for guests or multigenerational living. An engineer-approved option to remove a non-load-bearing wall allows for easy creation of a great room concept—a virtual rendering is included in the photo gallery to illustrate the potential. The chef’s kitchen features GE Monogram and Fisher & Paykel appliances, a butler’s pantry, beverage station, and pocketing glass doors opening to a full summer kitchen, PebbleTec saltwater pool and spa, and lush outdoor spaces. Hurricane-rated windows and doors, elevated construction, and a full-home generator protected the interior during recent storms—no water intrusion or damage occurred, with water reaching only the garage level. Extras include a 13,000 lb. lift, composite dock, 3-car garage with EV charger, whole-house water filtration, security system, and ample storage. A rare opportunity to own a private, resilient, and reimagined Siesta Key waterfront retreat.

3465 Gulfmead Drive, Sarasota

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