Location: Sarasota , 34242
Do Not Show Listings
5830 MIDNIGHT PASS RD #61, SARASOTA, FL 34242
$598,000198 Days on yellowkey MLS ID: A4672481
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1963 Tax: $3,746 (2025)Community: Jamaica RoyaleCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,746
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Welcome to a place where mornings begin with the sound of gentle waves and evenings settle into sunsets that linger long after the sky fades. This ground-level villa places you within steps of the Gulf in one of Siesta Key’s most cherished beachfront communities. The interior of this home has been completely transformed with a full remodel, bringing a fresh, modern feel to every room. This renovation was done with both comfort and longevity in mind, creating a space that is truly ready for its next chapter with a new owner. Updates include state-of -the art impact resistant doors and windows, a re-imagined kitchen with new lower cabinets and granite countertops, an upgraded primary bathroom, new base trim and interior doors, and all-new furniture and appliances, including a new dishwasher, refrigerator, washer, dryer, AC, and water heater. Jamaica Royale is known for its private white-sand beach, three heated pools, serene garden pathways, and welcoming coastal atmosphere. Not only do residents enjoy true maintenance-free living in Jamaica Royal, but cable, internet, water, and sewer are also included in association dues. The convenience continues with optional in-house rental management, allowing owners to easily generate income when they are away while keeping their home professionally cared for. Everything you need is within easy reach, yet every moment here feels like a getaway. Spend your days stretched out on the sand in a private cabana, making new friends while wandering the shoreline at sunset, or grilling up the day's fresh catch on the beachside BBQ. Then, when it's time for venturing out, public transportation makes it easy to head to downtown Sarasota, Gulf Gate, or Siesta Village for dining, music, and local coastal charm. If you have been waiting for the perfect home by the beach, that has already been beautifully updated and offers the full island lifestyle, this villa is the one. Schedule your private showing and experience what makes Jamaica Royale such a special place to call home. A 1% RATE BUY-DOWN IS AVAILABLE TO QUALIFIED BUYERS WHO WORK WITH THE SELLER'S PREFERRED LENDER.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Domanic Calamese (941-914-0038)
8504 HERON LAGOON CIR, SARASOTA, FL 34242
$2,800,000128 Days on yellowkey MLS ID: A4681098
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 2675 Built: 2026 Tax: $3,873 (2025)Community: Heron Lagoon LodgesSpa: YesSingle Family
Taxes:$3,873
Elementary School: None
High School: Riverview High
Middle School: Sarasota Middle
Remarks: Pre-Construction. To be built. Dreaming of building a brand-new home on Siesta Key but not sure where to start? Have you ever built a bonfire on the beach and had 50 of your closest family and friends over for a beach party? This happens no where else on Siesta Key. Residents in the neighborhood enjoy the unique privilege of crossing Heron Lagoon via a private bridge to the sands of Siesta Key beach. There’s a cabana for storing your beach chairs, kayaks and water toys. It’s a one minute walk from your front door to the bridge and another minute to cross it! Here's an opportunity to build your dream home on a pristine, oversized lot nestled on the quiet end of Siesta Key. At this lot the hard work has already been done for you. This to-be-built coastal residence has been thoughtfully designed as a 4-bedroom, 4.5-bath home with a den and club room and an experienced builder is already secured. All that's left is for you to personalize the finishes and make it distinctly yours. This exceptional lot offers unparalleled privacy, lush natural surroundings on an expansive corner parcel. Only minutes to restaurants, a marina to house your boat, and beautiful Turtle Beach where you can walk to newly opened Midnight Pass. The previous structure has been removed, and a clean slate is waiting for your vision. Use the Showing Time button to schedule your visit today. This is your opportunity to step into the Siesta Key lifestyle with a custom home already in motion, without the typical delays of starting from scratch. Schedule your visit and walk the property to experience the location firsthand. Property is also being sold as land only.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
757 BEACH RD #308, SARASOTA, FL 34242
$549,00073 Days on yellowkey MLS ID: TB8492005
0 Days Off yellowkey (back on 4/29/2026)
REDUCED by $46,500 (7.8%) on 04/23/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 816 Built: 1970 Tax: $5,582 (2025)Community: Crescent RoyaleCondo
Taxes:$5,582
Remarks: 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
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
5880 MIDNIGHT PASS RD #605, SARASOTA, FL 34242
$1,150,000111 Days on yellowkey MLS ID: A4683118
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $10,494 (2025)Community: CasarinaSpa: YesCondo
Taxes:$10,494
High School: None
Middle School: None
Remarks: Imagine awakening each morning to the gentle symphony of waves caressing powder-white sand on Siesta Key, where the Gulf of Mexico stretches endlessly before you in shimmering turquoise splendor. This exquisite two-bedroom, two-bathroom condominium nestled within the prestigious Casarina community offers a lifestyle that transcends ordinary coastal living. Perched elegantly upon seven acres of lush, tropical grounds directly on world-renowned Crescent Beach, this beautifully updated residence delivers the quintessential beach sanctuary you have been dreaming of. Hurricane impact windows provide peace of mind while framing breathtaking beach and gulf views that will steal your breath daily. The thoughtfully renovated kitchen boasts stainless steel appliances, while sophisticated stone-look tile graces the lanai, creating a seamless indoor-outdoor retreat. Beyond your private haven, Casarina's resort-caliber amenities rival the finest destinations. An expansive heated pool and spa with cabana and outdoor kitchen beckons lazy afternoons, while two grilling areas invite convivial gatherings under swaying palms. A sunset beach-side deck transforms evenings into pure magic, and lighted tennis and pickle-ball courts satisfy your competitive spirit. The community thoughtfully provides an on-site management office, fitness room, and generous community center for celebrations and social events. Just moments away, the charming Siesta Key Village offers eclectic dining and boutique shopping, while Phillippi Estate Park provides serene natural escapes. Whether you envision this as your permanent paradise or a cherished seasonal retreat, this freshly repainted gem delivers beach-side living at its absolute finest. Schedule your private showing today and let the Gulf whisper your name.
Listing is courtesy of: SARABAY REAL ESTATE INC (941-355-7696)
Listing Agent: Dion Souza (941-302-3881)
757 BEACH RD #310, SARASOTA, FL 34242
$950,000191 Days on yellowkey MLS ID: A4673722
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1122 Built: 1970 Tax: $8,252 (2024)Community: Crescent RoyaleCondo
Taxes:$8,252
Tax Year: 2024
Remarks: Front row view of the world-renowned Siesta Key Beach. This unit is situated right across from the public beach and is withing 0.9 miles/3 minutes to the village. This turnkey fully furnished and equipped unit is move in ready. Right thru the front door you are greeted with an open floor plan overlooking the beach and the gulf water views. Smell the salt air as you lounge or dine on your large private screen in patio. The unit offers a beach vibe paint palette well-appointed furnishing and shows ownership pride. As you enter you are greeted with a large kitchen with stainless steel appliances an abundance of cabinets and granite counter tops and a large island. The kitchen is fully stocked and ready for all your cooking needs. Next to the kitchen is a large dining area with a table for 6. The living room also overlooks the beach and water views. It has a large sectional and side chair plenty of room for all your guests. This unit offers a master suite overlooking the gulf with an ensuite full bathroom. The guest room is also a great size and has a full attached bathroom. Both bedrooms have oversized walk-in closets plus a separate owner's closet. The unit also offers luxury vinyl flooring, tile and carpet. Impact patio doors for a piece of mind. The community is gated, and you have an assigned carport for parking. Crescent Royal has a managed onsite weekly rental program. The site offers a heated pool, fitness center, shuffleboard, and a grilling area. Public beach is right across the street. Also, there is Trolley that gives you access to the village or take a short stroll to dining, entertainment, shopping and yes sand dollar picking on the sand bar. This unit is currently in the rental program and has an excellent rental history and future bookings. The gulf is calling don't miss this beautiful beach retreat.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Shirley Pyles, Pa (941-894-4297)
3458 ANGLIN DR, SARASOTA, FL 34242
$2,595,000111 Days on yellowkey MLS ID: A4683447
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2513 Built: 1983 Tax: $19,659 (2025)Community: Bay Island ParkSpa: NoSingle Family
Taxes:$19,659
Remarks: Welcome to Bay Island, ideally positioned on the north end of Siesta Key, where island living meets exceptional convenience. Just moments from Siesta Beach, Siesta Key Village, and downtown Sarasota’s waterfront dining and cultural offerings—with easy access on and off the island—this elevated Key West-style residence is set across a rare double lot, an uncommon offering on Siesta Key. Fully renovated in late 2019, the home features new siding, roof, electrical, plumbing, irrigation, hurricane-rated windows and French doors, and two HVAC systems. It has since been further enhanced with premium retractable invisible screens on all French doors, kitchen and bath refinements, and a whole-house water filtration system, along with additional upgrades that reflect its continued care and quality. The open-concept floor plan is filled with natural light, highlighted by vaulted ceilings, LVP flooring, and a natural gas fireplace. Multiple covered terraces extend the living space outdoors, reinforcing the home’s relaxed coastal design. The kitchen is designed for both everyday living and entertaining, centered around a large quartzite island with extensive drawer storage and pull-out shelving. A full Thermador appliance package includes a gas range, refrigerator and freezer columns, and dishwasher. Soft-close cabinetry and thoughtful storage solutions provide both function and efficiency. French doors open to an oversized covered deck overlooking mature tropical landscaping. The well-sized owner’s suite is located on the main living level and includes a walk-in closet and a private en-suite bathroom featuring a double vanity and large walk-in shower. A den on this level offers flexibility and can easily serve as a fourth bedroom or home office. Upstairs, two generously sized guest bedrooms share a newly appointed bathroom and enjoy access to a third-level terrace ideal for sunset views. Outdoor living sets this property apart. The double lot creates an expansive backyard with a recently resurfaced pool, travertine decking, and multiple covered terraces—an uncommon offering on Siesta Key. The additional lot provides flexibility for future enhancements while preserving privacy and open space.
Listing Agent: Barbara May (404-822-9264)
4626 GLEASON AVE, SARASOTA, FL 34242
$695,000132 Days on yellowkey MLS ID: A4680372
0 Days Off yellowkey (back on 4/28/2026)
REDUCED by $35,000 (4.8%) on 04/02/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 1144 Built: 1955 Tax: $6,783 (2025)Community: Ocean BeachSingle Family
Taxes:$6,783
Remarks: Under contract-accepting backup offers. You're about to miss it...coming off the market 6/1. A perfect blend of old-school cool and 2026 finishes, this mid-century modern bungalow is a true "buy it and move-in tomorrow” type home. Most importantly, no high condo/HOA fees. Polished terrazzo floors, vaulted ceilings, it’s just fun all over. Fully renovated with crisp coastal selections. It has a nice sunroom for a large party gathering or workout room, art studio, play area. Carport equipped with RV hookups and motor court driveway. Plenty of parking space for bikes, scooters, and golf carts. The landscaping is immaculate, professionally designed by the owner including an advanced drainage system helping keep you dry 24/7/365. Not far from the Village, close to the beach, and minutes to North bridge. Clean, affordable, easy beach living. Being offered turn-key furnished.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Jason Skowronski (941-812-6090)
5920 MIDNIGHT PASS RD #406, SARASOTA, FL 34242
$1,299,000421 Days on yellowkey MLS ID: A4649118
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1334 Built: 1971 Tax: $10,637 (2024)Community: Sarasota Surf & RacquetCondo
Taxes:$10,637
Remarks: TOWER RESIDENCE IN SARASOTA SURF AND RACQUET CLUB. 2BR/2BA in a Gulf & Beach Front Community – Resort Style Amenities – Proven Vacation Rental – Move In Ready - Enjoy the island lifestyle in one of Siesta Key’s most desirable beach front communities, located directly on Crescent Beach, the powdery white sand shoreline that makes Siesta Key world-famous. This beautifully appointed 4th-floor residence in the sought-after Tower Building offers convenient access to the pool and beach, making it a favorite for owners and vacation guests alike. Expansive windows invite natural light and offer a Gulf view, creating a bright and inviting coastal retreat. Interior highlights include: Luxury vinyl plank (LVT) flooring throughout; Granite kitchen countertops; Split-bedroom floor plan for added privacy; Open living and dining areas designed for relaxed beach living. Residents and guests enjoy private access to Siesta Key’s Crescent Beach along with exceptional on-site amenities: Two heated swimming pools; Beachside & poolside BBQ grills; Fully equipped fitness center; Four pickleball courts; Three tennis courts (including two Har-Tru clay courts - the only resort clay courts on Siesta Key); On-site rentals for cabanas, tents, umbrellas & beach equipment. With a three-night minimum rental policy and professional on-site rental management, this condo offers exceptional opportunity in one of Siesta Key’s most recognized beachfront communities. Ideal as a personal beach retreat, full time residence or a high-demand vacation rental. Offered fully furnished, ready for immediate enjoyment, this residence delivers the Siesta Key lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Greg Hudson (941-302-1485)
604 AVENIDA DE MAYO, SARASOTA, FL 34242
$1,250,000206 Days on yellowkey MLS ID: A4671973
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 2173 Built: 1951 Tax: $12,202 (2023)Community: Siesta BeachApartment
Taxes:$12,202
Tax Year: 2023
Remarks: Back on the market! Beautiful triplex that went through a total renovation 2024. A re-roof project was completed in 2022 and is under a transferable warranty. Property can be rented as 3 separate units - Studio, One Bedroom, Three Bedroom. Property could easily be converted to a duplex (2 BR / 1 BA + 3 BR / 2 BA) in the event the owner prefers to live in one unit and rent the other. Just a few blocks from Siesta Village and an easy stroll to the beach, this is a great location to enjoy what Siesta Key has to offer! Total living Space - 2173 SF Main Unit - 3 BR / 2 BA - Approx - 1400 SF Second Unit - 1 BR / 1 BA - Approx. 600 SF Third Unit - Studio / 1 BR 1 BA - Approx - 200 SF Total living Space - 2173 SF Main Unit - 3 BR / 2 BA - Approx - 1400 SF Second Unit - 1 BR / 1 BA - Approx. 600 SF Third Unit - Studio / 1 BR 1 BA - Approx - 200 SF
Listing Agent: Dan Desoto, Jr (941-567-8006)
316 BEACH RD, SARASOTA, FL 34242
$5,499,000106 Days on yellowkey MLS ID: A4683801
Bed: 8 Bath: 9.0 Gar: 2 Liv Area Sq Ft: 4681 Built: 1996 Tax: $37,822 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$37,822
Remarks: Just steps from the shoreline, this coastal home offers deeded beach access and sweeping panoramic views of the Gulf. Completely remodeled in 2021, the property lives and performs like new construction, blending modern coastal design with durable, rental-ready finishes throughout. Thoughtfully designed across three living levels and serviced by a private elevator, the home features 8 bedrooms, 8 full baths, and 2 half baths, with expansive gathering spaces suited for both everyday living and hosting. With a proven track record as a high-performing short-term rental, the property generates approximately $400,000 to $500,000 annually, offering strong income potential alongside its lifestyle appeal. The top floor serves as the heart of the home, where the main kitchen and primary living area open directly to a Gulf-facing balcony showcasing breathtaking, unobstructed water views. This elevated vantage point creates a stunning backdrop for daily living, with the kitchen, dining space, and great room all positioned to take in the scenery. A secondary club room with wet bar provides an additional space to gather, while multiple balconies throughout the home frame the coastal setting from different vantage points, including select bedroom suites. Below, the outdoor living space features a private pool and integrated spa surrounded by lush landscaping, along with a fully equipped outdoor kitchen with built-in grill, refrigeration, and dining area. All eight bedroom suites offer ensuite baths and generous accommodations, with several enjoying Gulf views and private balcony access. Located near beach access and Siesta Key Village, this is a rare opportunity to own a fully renovated coastal home that delivers both luxury living and compelling investment performance.
Listing Agent: Curt Ware (941-587-9122)
445 REID ST, SARASOTA, FL 34242
$1,340,000205 Days on yellowkey MLS ID: A4671563
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1750 Built: 1961 Tax: $10,958 (2024)Community: Ocean Beach RepSpa: NoSingle Family
Taxes:$10,958
Remarks: Coastal Chic meets Contemporary Classic on Siesta Key. This 3-bed, 2-bath oasis with saltwater pool boasts 1,750 square feet under air, $100,000 in upgrades and $50,000+ in brand new designer furnishings from Crate & Barrel. In 2025, the owners installed new tile flooring throughout the home, all new appliances, new washer & dryer, new doors (except the front door), new water heater and pool pump. New kitchen cabinetry and countertops, new cabinetry in both baths, and new ceiling fans. HVAC is 3 years old. The 30-year dimensional roof is 7. Home has been re-plumbed. Offered turnkey furnished, this distinctive property earns $70K in rental income annually. The open concept living area invites you to unwind, with natural light that glistens through three sets of brand-new impact resistant French doors overlooking your private lanai and pool. The wood burning fireplace & skylight create a space where relaxation & indulgence harmoniously coexist. The fully stocked kitchen provides the perfect ambiance for intimate gatherings & lively entertainment. Step onto the 35’ long screened patio and take a dip in the heated saltwater pool. Rinse off after a day at the beach in the outdoor shower. Lounge on the deck and soak up the sun. Gather around for unforgettable barbecues under the starlit sky. Retreat to the tranquil owners’ suite, your personal sanctuary, with a serene atmosphere, private en-suite bath, and walk in closet. Surrounded by lush foliage, a glass enclosed sunroom is perfect as an office or meditation room. The primary bath features dual sinks and modern fixtures. The additional 2 bedrooms provide versatility for accommodating guests. A laundry room is just off the primary suite, with a separate entrance to the covered carport. Fully fenced for privacy. Xeriscape means never having to mow! Mature landscaping & circular driveway on an oversized corner lot with room for an RV or boat. Renowned for its vibrant coastal lifestyle, this residence is a stone’s throw from the #1 Beach in the US. Situated in a quiet neighborhood on the North end of Siesta Key, the home is one mile from Siesta Village, bustling with restaurants, cafes and shops, as well as Siesta Key’s world-famous Sunset Beach & Pier. Downtown Sarasota’s Bayfront, with its world-class shopping, dining, & cultural events is 5 miles away. Nature lovers, sports enthusiasts, and patrons of the arts have the best of Sarasota at their fingertips with outdoor activities that include waterfront dining, boating, biking, golfing, hiking & fishing nearby. With easy access to state-of-the-art medical facilities, Sarasota International Airport, and the I-75, the location of this home offers the perfect blend of serenity & convenience. A mix of modern luxury & coastal charm, this home presents an extraordinary opportunity to live your best life, whether it be used as a private retreat for your own personal enjoyment, or a lucrative seasonal or annual rental.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Robin Leonardi (941-685-6270)
3360 HIGEL AVE, SARASOTA, FL 34242
$1,549,000120 Days on yellowkey MLS ID: A4682008
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2006 Built: 1960 Tax: $13,348 (2025)Community: Siesta Rev OfSpa: YesSingle Family
Taxes:$13,348
Remarks: Welcome to the home you've been waiting for! Your opportunity to own a fully updated island retreat pool home on world-famous Siesta Key. Imagine waking up minutes from powdery white quartz sand beaches, spending your afternoons poolside under the Florida sun, and ending your evenings with sunset walks along the water. This four-bedroom, three-bathroom home offers the flexibility, comfort, and lifestyle today’s buyers are looking for — whether as your primary residence, second home, or income-producing weekly rental. Inside, the home has been completely updated and thoughtfully designed for modern coastal living. With three separate living room areas, there is space for everyone to gather, relax, and spread out comfortably. Whether hosting friends, accommodating extended family, or welcoming vacation guests, the multiple living spaces provide both connection and privacy — a rare and valuable feature in Siesta Key homes. Natural light fills the interiors, creating a bright and inviting atmosphere that reflects the relaxed elegance of island life. Step outside to your new private pool and expansive outdoor living space designed for year-round enjoyment. Lounge poolside with morning coffee, host dinners, or unwind after a day at the beach. The seamless indoor-outdoor flow captures what Siesta Key living is all about. One of the most compelling features of this property is the one-week minimum rental allowance — a highly sought-after benefit on Siesta Key. Weekly rental flexibility allows you to generate strong short-term rental income while still enjoying personal time in your island home. With Siesta Key consistently ranked among the top beaches in the world, demand for updated weekly rental properties remains strong throughout the year. Residents of this neighborhood also enjoy private access to a beach area on the Pass — a peaceful waterfront setting perfect for sunset strolls, kayaking, paddle boarding, fishing, or simply relaxing away from the main beach crowds. Located just minutes from Siesta Key Village, you are close to dining, boutique shopping, live music, and vibrant island culture. Downtown Sarasota, marinas, golf courses, and Sarasota-Bradenton International Airport are all within easy reach. Whether you are searching for your own Siesta Key escape, a turnkey beach home with a pool, or a high-performing weekly rental investment in Sarasota, 3360 Higel Avenue offers the rare combination of lifestyle, flexibility, and location in one of Florida’s most coveted coastal communities.
Listing Agent: Natalie Gutwein (941-993-2660)
218 PASS KEY RD #218, SARASOTA, FL 34242
$645,00062 Days on yellowkey MLS ID: A4689143
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1175 Built: 1973Monthly Fee: $1,323 Tax: $5,091 (2025)Community: Sandy Cove IiiCondo
Taxes:$5,091
Remarks: Enjoy the best of Siesta Key living in the highly sought-after Sandy Cove III, an intimate waterfront community of just 16 residences. This beautifully maintained, turnkey-furnished 2-bedroom, 2-bath condo offers comfort, style, and an unbeatable location just moments from Siesta Key Village and the Gulf. The open-concept main living area features tile flooring throughout and a thoughtfully updated kitchen with upgraded cabinetry and countertops, perfect for entertaining. Storm-rated sliding glass doors provide peace of mind while bringing in abundant natural light. An indoor laundry area adds convenience to everyday living. The second level includes a spacious guest bedroom, full bath, and a versatile bonus room currently used as an additional sleeping space—ideal for guests or a home office.Surrounded by lush tropical landscaping, Sandy Cove III offers a true coastal retreat with amenities including a heated community pool, kayak storage, and a charming historic clubhouse. Residents enjoy access to a private fishing pier and shell beach, where you can take in breathtaking Gulf views and unforgettable sunsets.This pet-friendly community is just a short walk to Siesta Key Village, known for its vibrant dining, shopping, and entertainment. Plus, you’re only a short drive to downtown Sarasota and St. Armands Circle for world-class shopping, dining, and cultural attractions. Whether you’re looking for a full-time residence, vacation getaway, or investment opportunity, this property checks all the boxes. Schedule your private showing today and experience the very best of Siesta Key living.
Listing Agent: Tim Yocum, Sr (941-915-4545)
1253 N BASIN LN, SARASOTA, FL 34242
$3,295,000239 Days on yellowkey MLS ID: A4668457
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3464 Built: 1971Monthly Fee: $450 Tax: $42,282 (2024)Community: Siesta Properties IncSpa: YesSingle Family
Taxes:$42,282
Remarks: One or more photo(s) has been virtually staged. This exquisitely reimagined waterfront estate embodies modern luxury and serene exclusivity, offering 174 feet of prime waterfrontage in the prestigious Sanderling Club on Siesta Key. On a lush, nearly half-acre parcel, the residence enjoys a southern orientation, where panoramic views of a bridgeless bay unfold through walls of glass. A backdrop of meticulously landscaped greenery ensures privacy, all just near the water’s edge. At the heart of the home lies a state-of-the-art culinary haven. The chef’s kitchen is equipped with premium Wolf and Sub-Zero appliances, including a gas range and integrated espresso system, set within rich Merillat solid-wood cabinetry and dual islands designed for function and entertaining. Flowing seamlessly into the sunlit living and dining areas, the open-plan design creates an effortless connection between indoors and out. The living space extends gracefully to a sophisticated entertainment patio, where a firelit lounge, sparkling pool and fully appointed outdoor kitchen echo the refinement found within. The primary suite offers a tranquil retreat, framed by a garden and oak vista, and complemented by a spa-inspired bath featuring a deep soaking tub, dual vanities, and indoor and outdoor showers. An adjoining office doubles as a guest suite, while additional en-suite accommodations ensure privacy and comfort for visitors. Modern conveniences and peace of mind abound such as remote-controlled wrought-iron gates, impact-resistant windows and doors, whole-house water treatment, advanced smart-home systems, new roof, backup generator and environmentally conscious amenities, including a 500-gallon propane supply and integrated mosquito-repellent system. As a resident of Sanderling Club, you’ll enjoy access to a private beach, boat slips, tennis courts, clubhouse and 24-hour security, an unrivaled blend of leisure, privacy and coastal sophistication. This residence has been meticulously curated for those who seek the ultimate fusion of luxury and tranquility, an invitation to a lifestyle defined by elegance, ease and timeless waterfront living.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Louis Wery (941-232-3001)
6154 MIDNIGHT PASS RD #A-3, SARASOTA, FL 34242
$619,00062 Days on yellowkey MLS ID: A4689306
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 836 Built: 1966 Tax: $4,427 (2025)Community: Casa Blanca VillasCondo
Taxes:$4,427
Remarks: Tucked along the sugar-white sands of world-renowned Siesta Key, this freestanding villa offers the rare combination of effortless ownership, strong rental potential, and immediate coastal enjoyment. With direct beach access just steps away, every day begins and ends with the Gulf as your backdrop. Thoughtfully and completely updated, the residence features easy-care terrazzo flooring, a beautifully renovated kitchen with stainless appliances and dining space, along with a refreshed full bath and convenient half bath. The screened porch invites year-round indoor-outdoor living, while an impact-rated sliding glass door enhances both comfort and peace of mind. Positioned just steps from the community pool and clubhouse, this villa is part of an active, well-managed rental community offering flexible 5–7 day minimum rentals, making it an exceptional opportunity for those seeking income potential with personal-use flexibility. On-site management simplifies ownership, whether you’re local or remote. Sold furnished, the home is ready for immediate enjoyment or rental—just bring your suitcase. Parking is conveniently located directly in front of the unit. Beyond the property, you’re ideally situated near Siesta Key’s popular dining, shopping, and parks, while still enjoying a quieter stretch of beach perfect for morning walks, sunset swims, and relaxed days on the sand. Whether you’re looking for a smart investment, a personal retreat, or the perfect blend of both—this villa delivers the Siesta Key lifestyle with ease.
Listing Agent: Ryndie Brusco (941-809-6913)
847 FREELING DR, SARASOTA, FL 34242
$3,950,00048 Days on yellowkey MLS ID: A4690268
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4034 Built: 1954 Tax: $40,498 (2025)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$40,498
Remarks: Located in the highly sought-after Bay Isles community on Siesta Key, this property at 847 Freeling Drive offers a rare opportunity to customize and create your ideal coastal home. Positioned on the first street onto Siesta Key, the location provides exceptional convenience to the bridge, mainland, and all that the island has to offer. The home features 4 bedrooms and 4.5 bathrooms, with the upper level remaining intact and in great condition. The ground level experienced flooding during the recent hurricanes; however, the seller has already completed professional remediation, providing a clean slate for updates and renovations to suit your vision. Situated on a protected deep-water basin, the property is ideal for boating and waterfront living, complete with a private dock, no fixed bridges, and direct access just minutes to the Gulf. The home also features a pool, offering the perfect foundation to create a true coastal retreat. This is a unique opportunity to secure a well-located waterfront property and finish it to your exact specifications in one of Siesta Key’s most desirable communities.
Listing Agent: Michelle Ward (941-920-2460)
6006 MIDNIGHT PASS RD #51, SARASOTA, FL 34242
$575,00064 Days on yellowkey MLS ID: P4938368
Bed: 1 Bath: 0.0 Liv Area Sq Ft: 600 Built: 1960 Tax: $3,999 (2025)Community: Casa MarSpa: NoApartment
Taxes:$3,999
Remarks: PRIVATE BEACHFRONT CONDO! Experience the ultimate Siesta Key lifestyle with this beautifully updated, TURNKEY FURNISHED 1-bedroom, 1-bath residence in the highly sought-after Casa Mar community, offering 300ft of GULF/OCEAN FRONT, WATERFRONT, WATER ACCESS to the world-famous Siesta Key Beach. This property is ALREADY GENERATING INCOME with a strong short term rental history, making it an exceptional investment opportunity or personal beach vacation retreat. Perfectly positioned within the complex and just steps from the pool, this bright and modern unit features a spacious layout with a welcoming foyer (found in only select units), a large bedroom with abundant closet space, and a versatile Florida room overlooking the courtyard and pool...ideal for relaxing, morning coffee, or hosting guests. Hurricane-rated windows and doors provide peace, quiet, and year-round comfort. Enjoy resort-style amenities including two pools (one heated), tennis and pickleball courts, shuffleboard, BBQ grilling areas, picnic spaces, and lush tropical landscaping, all within a no-road-to-cross beachfront setting. Recent community upgrades include a NEW ROOF, NEW SEAWALL, landscaping, and a secure gated entry for added privacy. Additional conveniences include covered parking just steps from your door, nearby laundry facilities, onsite management, and a private mailbox. This high-demand weekly rental property offers both immediate income and future upside, with OWNER FINANCING AVAILABLE for added flexibility. Located just minutes from dining, shopping, and Siesta Key Village, with trolley access right outside, this is a rare opportunity to own a piece of paradise that seamlessly blends income potential with effortless coastal living. Seller financing and private financing available. Do NOT WAIT, it will not last long!
Listing is courtesy of: HUT REALTY, LLC (407-559-2929)
Listing Agent: Daniel Hut (863-400-6090)
5400 OCEAN BLVD #5-3, SARASOTA, FL 34242
$1,295,000220 Days on yellowkey MLS ID: A4669686
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 928 Built: 1970Monthly Fee: $1,599 Tax: $10,150 (2025)Community: Beach TerraceCondo
Taxes:$10,150
Middle School: McIntosh Middle
Remarks: New price! Experience the ultimate in Siesta Key beachfront living. Directly on world-renowned Siesta Beach, rated #1 in the U.S. and #4 worldwide by TripAdvisor, this stunning fifth-floor corner residence captures the essence of luxury coastal living. Recently renovated to perfection, this one-bedroom, 1.5-bath condominium offers a rare combination of modern sophistication, coastal elegance and sweeping Gulf views. Designed by the acclaimed architect Frank Folsom Smith, the iconic Beach Terrace building is an architectural gem. This residence is a standout, meticulously renovated by a designer whose impeccable taste and attention to detail elevate the home well beyond expectation, with a focus on efficient use of space. The result is a move-in-ready retreat where every inch reflects exceptional craftsmanship and thoughtful design. Go inside to discover two walls of wrap-around, floor-to-ceiling impact-rated sliding glass doors that open to three private balconies, expanding the total usable space to 1,284 square feet, immersing you in stunning views of the Gulf’s turquoise waters and legendary white quartz sand. The chef’s kitchen is a masterpiece, featuring Quartzite countertops, custom European cabinetry, high-end stainless steel appliances and an expansive island that anchors the open concept living area. The spacious great room, bathed in natural light, includes a custom Murphy bed for overnight guests and provides a setting to enjoy Siesta Key’s radiant sunsets. Every element of this home is designed for comfort and style, from the serene primary suite to the elegant finishes throughout. The primary bath reflects a flawless balance of form and function. Featuring European cabinetry, a glass-enclosed walk-in shower and spectacular floor-to-ceiling tilework, this serene space exudes modern elegance. Every detail, from the sleek fixtures to the artful tile patterns, has been thoughtfully curated to create a spa-like sanctuary that complements the residence’s sophisticated coastal aesthetic. Additional improvements include a new air conditioning system with updated ductwork, new electrical upgrades and a new water heater, ensuring comfort and peace of mind for years to come. Within Beach Terrace’s exclusive enclave, residents enjoy the security of a controlled-access lobby, the convenience of an on-site manager, and premium amenities including a heated saltwater pool overlooking the Gulf, fitness center and community lounge. Go outside and you’re just moments from Siesta Key Village, where you’ll find inviting boutiques, beachside cafés and vibrant local dining. With the beach at your doorstep, a car becomes optional. And when you crave a touch of city life, downtown Sarasota’s acclaimed cultural scene, restaurants, galleries, opera, ballet, and theaters, is just minutes away across the north bridge. This is more than a residence, it’s a rare opportunity to own a beautifully reimagined piece of paradise, where luxury, location and lifestyle converge to create an extraordinary beachfront experience on Siesta Key.
Listing Agent: Judie Berger (941-928-3424)
9393 MIDNIGHT PASS RD #P4, SARASOTA, FL 34242
$659,000224 Days on yellowkey MLS ID: A4669033
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1380 Built: 1975 Tax: $7,483 (2024)Community: Pointe On Midnight PassCondo
Taxes:$7,483
Remarks: Price Reduction!! ENJOY AWE-INSPIRING SUNRISES AND SUNSETS from this stunning two bedroom, two bath PENTHOUSE condo at the southernmost end of Siesta Key. A corner unit with extra windows, enjoy water views from every room! Wake to breath-taking sunrises over Neville Preserve on Little Sarasota Bay and marvel at spectacular sunsets over the Gulf of Mexico. The largest of units offered at The Pointe, this 10th floor residence is filled with natural light through abundant windows and sliding glass doors. The large kitchen opens to the living room which features beautiful engineered hardwood flooring, crown and base molding, and ceiling beams to separate the dining and living areas. A generous screened and glassed lanai - accessible from both the living room and the primary suite - provides your front-row seat to sunrises, downtown Sarasota, and spectacular wildlife. The private primary retreat offers a large bedroom, a walk-in closet, a built-in vanity with sink, and an ensuite bath with walk-in shower, second sink and toilet. A comfortable guest bedroom and full hall bath complete the main living space. A large laundry room with ample cabinetry, a walk-in utility room off the lanai and a large ground floor assigned lock-off bin provide coveted storage space. An oversized under-building parking space convenient to the building entry completes this unit. Located at the southern tip of Siesta Key, this 5+ acre gated community is beautifully landscaped and features every amenity: heated pool and spa, lighted tennis and pickle ball courts, private boat docks, kayak and canoe racks and launch, a beautiful and fully equipped club house, saunas, fitness centers, an island pavilion with grills, and on-site management and maintenance. A walkway along the water surrounding the property is idyllic for scenic strolls. The Pointe is just minutes' walk to Turtle Beach and three great restaurants. This really is a must see!
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Robert Ruiz (941-544-3299)
6157 MIDNIGHT PASS RD #E22, SARASOTA, FL 34242
$399,900104 Days on yellowkey MLS ID: A4684348
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 748 Built: 1974 Tax: $3,648 (2025)Community: Bay OaksCondo
Taxes:$3,648
Remarks: BEAUTIFUL 1 BEDROOM 1 BATH UNIT IN BAY OAKS on SIESTA KEY ** TURNKEY FURNISHED ** 1 WEEK RENTALS ALLOWED ** The waves crash, the sand is sugar-coated and the sunsets are striking on Siesta Key.. There is no better location to invest in a 2nd home or investment property. This condo is located on the 2nd floor of building E in Bay Oaks. You will love the large open kitchen and expansive design of this "Santa Fe" themed unit. Located at the end of the 2nd floor in a corner of the building, privacy and tree lined views from the patio create serenity for the owner and tenants. Boasting 750ft2 of living area, there is no wasted space with eat-in dining and wide-open family space. The master bedroom is also open & airy with an on-suite vanity and large walk-in closet, including a washer/dryer. Bay oaks is located just north of the Stickney point bridge allowing more quick escape off the island to Publix, Bealls, Starbucks and Gulf Gate shopping. The community provides a wonderful community pool and tennis court with a full-time manager on site. Beach access 12 is the best public access to the white sands of Siesta Key or catch the Trolley and enjoy and scenic ride to the public beach. Now is the time to invest in Siesta Key real estate.
Listing is courtesy of: SHIRLEY INTERNATIONAL REALTY (941-448-4872)
Listing Agent: Justin Shirley (941-448-4872)
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