Location: Sarasota , 34242
Do Not Show Listings
4708 OCEAN BLVD #E7, SARASOTA, FL 34242
$2,299,000307 Days on yellowkey MLS ID: A4665893
1 Days Off yellowkey (back on 7/23/2026)
REDUCED by $51,000 (2.2%) on 05/04/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 1981 Tax: $16,841 (2025)Community: Windward PassageCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$16,841
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. Experience refined coastal living in North Siesta Key at 4708 Ocean Boulevard, a fully renovated 2025 corner residence ideally positioned on the Gulf of Mexico at Big Pass. This exceptional 3-bedroom, 3-bath condominium offers unobstructed panoramic views of the Gulf, Sarasota Bay, and distant vistas of Lido Key and downtown Sarasota. Encompassing 2,277 square feet with miles of Gulf-front views, the residence has been thoughtfully redesigned with wide-plank European engineered oak flooring, impact-rated windows and doors, and integrated smart-home technology throughout. The chef’s kitchen is a statement in both form and function, featuring custom cabinetry, Milano Dolomite countertops, a striking Macaubas Quartzite island, and premium GE Café appliances—perfect for entertaining against a backdrop of endless blue water. The primary suite is a private retreat with direct access to a Gulf-front balcony and a spa-inspired bath complete with dual vanities, rainfall shower, and bidet. Two additional guest suites provide comfort and privacy, each finished with designer details. Additional highlights include a two-car tandem garage with hurricane-rated door, new HVAC systems, electric hurricane shutters, and an integrated sound and entertainment system. Amenities include a heated pool, guest parking, and direct walking access to the sugar-white sands and vibrant Village of Siesta Key. This residence blends timeless coastal elegance with modern luxury—an extraordinary Gulf-front retreat on one of Siesta Key’s most coveted stretches of shoreline.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Stacey King (646-734-5014)
1128 W PEPPERTREE LN #111, SARASOTA, FL 34242
$669,00054 Days on yellowkey MLS ID: A4695723
0 Days Off yellowkey (back on 7/23/2026)
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 1120 Built: 1974 Tax: $3,746 (2025)Community: Peppertree Bay IiiSpa: NoCondo
Taxes:$3,746
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Experience the ultimate Siesta Key lifestyle in this beautifully updated Gulf side first-floor, turnkey furnished 2-bedroom, 1.5-bath condo with tranquil pond views and deeded beach access to the #1 beach in the USA. Thoughtfully renovated and move-in ready, this charming residence features large-format porcelain tile flooring, crown molding, fresh paint, updated plumbing, new impact-resistant glass doors and windows, spacious walk-in closets, a beautifully remodeled kitchen with new appliances, full-size washer and dryer, new ceiling fans, Tempur-Pedic mattresses, and quality Pottery Barn and Crate & Barrel furnishings. Relax in the enclosed lanai overlooking the peaceful pond and stone waterfall, or enjoy the convenience of your designated parking space just outside the door. Located within the highly desirable 16-acre beach-to-bay community of Peppertree, residents enjoy private beach access, two heated pools, two clubhouses, a fitness center, saunas, tennis and pickleball courts, BBQ areas, a fishing pier, on-site management, and a rental office. Just minutes from Siesta Key Village's shopping, dining, and entertainment, this property offers the perfect combination of personal enjoyment and investment potential, with existing rentals in place from February 1 through March 31 for immediate income. Simply bring your suitcase and start enjoying your own private slice of paradise.
Listing is courtesy of: PEPPERTREE BAY REALTY INC (941-914-3380)
Listing Agent: Cheryl Santelli (941-924-8305)
1135 LAKE HOUSE CIR #C115, SARASOTA, FL 34242
$799,9005 Days on yellowkey MLS ID: A4700455
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1352 Built: 1981Monthly Fee: $1,096 Tax: $6,916 (2025)Community: Our House At The Bch PhiiCondo
Taxes:$6,916
High School: Riverview High
Remarks: Welcome to your Siesta Key beach retreat! Perfectly positioned directly across from world-famous Siesta Key Beach, this immaculate, beautifully renovated 2-bedroom, 2-bath condominium offers the ideal combination of coastal luxury and exceptional investment potential. Completely renovated in 2019, this turnkey residence features recently installed hurricane-impact windows and sliding glass doors, a beautifully updated kitchen with stone countertops and stainless-steel appliances, a remodeled master suite, updated bathrooms, all-new PVC plumbing throughout, in-unit laundry, and a bright, open floor plan designed for easy beach living. Relax on your private lanai overlooking the tranquil lake or take a short walk to the powder-soft sands and crystal-clear waters of Siesta Key Beach. A rare attached private garage with epoxy floors provides additional convenience and storage. Residents and guests enjoy outstanding community amenities, including a pavilion with grills, an outdoor shower, a heated pool, tennis and pickleball courts, and beautifully maintained tropical grounds. Investors will appreciate the short-term rental flexibility, with both on-site professional property management and self-management options available, allowing owners to maximize rental income while maintaining complete flexibility. Whether you’re searching for a full-time residence, vacation getaway, or income-producing property, this condominium checks every box. Most furnishings are negotiable, offering the opportunity to purchase a fully furnished, turnkey property and begin enjoying or renting it immediately. Located just minutes from Siesta Key Village’s popular restaurants, boutique shopping, and entertainment, this is a rare opportunity to own a move-in-ready property in one of Florida’s most sought-after beach communities.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Joey Mccall (585-721-8922)
5673 MIDNIGHT PASS RD #201, SARASOTA, FL 34242
$449,50058 Days on yellowkey MLS ID: A4694956
REDUCED by $10,500 (2.3%) on 07/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1012 Built: 1975 Tax: $5,128 (2025)Community: White Sands VillageCondo
Taxes:$5,128
Remarks: Welcome to Unit 201 at White Sands Condominium — a bright, airy coastal retreat perfectly positioned on iconic Midnight Pass Road, Siesta Key. This spacious 1,012 sq ft, two-bedroom, two-bathroom condo is your gateway to the laid-back island lifestyle you've been dreaming of. Whether you choose to walk, cycle, or simply stroll, the world-famous Siesta Key Beach — voted the #1 beach in the USA — is just moments from your front door. Step inside and feel immediately at home. Generous natural light floods the open living spaces, beautifully complemented by wood-look flooring that runs throughout the unit, giving it a polished feel with all the ease of coastal living. The thoughtful layout offers two full bathrooms plus a convenient in-unit washer and dryer, so laundry day never interrupts island day. A dedicated storage closet rounds things out, giving you that extra breathing room that makes everyday life so much easier. When the sun starts to dip and the breeze picks up, step out onto your private covered lanai — the ideal spot to mix a cocktail, host friends, or simply let the Siesta Key evening wash over you. Sheltered and spacious, it extends your living space outdoors in true Florida fashion, and is the kind of feature you'll use every single day. Beyond your front door, White Sands offers a wonderful sense of community. Take a dip in the sparkling community pool, or take advantage of the community boat docks — available on a first-come, first-served basis — perfect for those who love life on the water. And with your own deeded covered parking spot, convenience is always part of the package. This is more than a condo — it's a front-row seat to everything that makes Siesta Key one of Florida's most sought-after addresses. Whether you're looking for a full-time residence, a vacation escape, or a smart investment, Unit 201 checks every box.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Ed French (747-272-6070)
5400 OCEAN BLVD #17-04, SARASOTA, FL 34242
$1,559,00025 Days on yellowkey MLS ID: A4698764
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1970 Tax: $13,856 (2024)Community: TerraceSpa: YesCondo
Taxes:$13,856
Elementary School: Southside Elementary
Tax Year: 2024
Remarks: The iconic Terrace building is a masterpiece designed by renowned architect Frank Folsom Smith. This modernist building, built of poured concrete exudes strength and durability. Situated directly on Siesta Key Beach, and built with walls of sliding glass doors in every room to take advantage of the diverse, magnificent views in all directions. This is the penthouse being offered turnkey furnished. Fantastic views in all directions. It's perfect location on the island within walking distance to Siesta Key Village, and all its offerings. The rooftop saltwater pool is a beautiful addition that provides privacy and lovely beach views. Take a cocktail out to watch the sunset over the water! The building itself has undergone significant upgrades, making it a prestigious address on Siesta Key. Complete replacement of cast-iron pipes, geothermal well driven HVAC system keeps cost low, new generator for entire building, monitored water sensors in all units, installation of new gates at the front entrance. The elevators have been replaced, the lobby has been redone, and is a waterfront masterpiece. Only the 4 penthouse units have use of the rooftop with decks. Come see for yourself why this stunning property is so very special.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Carol Thomas (941-349-3444)
70 AVENIDA VENECCIA #402, SARASOTA, FL 34242
$9,400,000784 Days on yellowkey MLS ID: A4612536
0 Days Off yellowkey (back on 6/3/2024)
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4510 Built: 2025 Tax: $7,518 (2023)Community: Sunset BeachSpa: YesCondo
Taxes:$7,518
Tax Year: 2023
Remarks: Virtually Staged. Pre-Construction. To be built. Introducing Sunset Beach, the premier boutique condominium on Siesta Key, offering refined beachfront living with breathtaking Gulf views. This exclusive collection features 11 residences with open-concept, flow-through floor plans and expansive glass walls. The spacious terraces and thoughtfully designed great room provide ample space for gathering, dining with family, entertaining guests, or simply relaxing and recharging. Experience the epitome of waterfront luxury, sophistication, and style, surrounded by nature's unmatched beauty. Nestled in a quintessential Siesta Key neighborhood, Sunset Beach offers the ultimate tropical modern luxury experience. With 175 linear feet of pristine private shoreline on the Gulf of Mexico, each home is uniquely designed by the world-renowned architecture firm MHK and features integrated native-inspired landscaping and gardens by DWJA Landscape Architects. Each residence includes 10-foot ceilings (except where dropped), floor-to-ceiling windows, oversized terraces with direct Gulf views, spacious living, dining, and entertaining areas, custom kitchens and bars with Sub-Zero and Wolf appliances, solid-core 8’ high entry and interior doors, floor-to-ceiling hurricane-resistant balcony sliders with laminated solar tint glass, sound-limiting laminated/insulated windows with solar-tinted glass, glass balcony railings, low voltage pre-wiring for state-of-the-art Smart Home technology, high-efficiency air conditioning and heating systems, and stained tongue-and-groove ceilings on terraces. This four-story development spans two and a half Gulf-front acres and includes a secured residential lobby with direct private elevator entry to each residence. The three-bedroom plus study residences range from 3,780 to 5,310 square feet. Spend your day relaxing by the poolside or take a few steps to a beachside lounge chair, where you can relax under an umbrella and enjoy the stunning views of crystal-clear water and white sand. Amenities include a beachfront swimming pool, spa, cabanas, and fire pit, lounge chairs, umbrellas, kayaks, paddle boards, and bikes, a state-of-the-art fitness center, beachfront grilling area, and private on-site storage units. Call us today to learn more!
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-867-9866)
Listing Agent: David Lehrman (941-321-5595)
8779 MIDNIGHT PASS RD #401H, SARASOTA, FL 34242
$595,000353 Days on yellowkey MLS ID: A4661131
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1485 Built: 1980 Tax: $4,969 (2025)Community: Island Reef Ii Ph 1 2 & 3Spa: NoCondo
Taxes:$4,969
Remarks: ENJOY THE BAY VIEWS FROM THIS UPDATED HOME! Kitchen with Granite countertop, Laundry in Residence, office space off foyer. Partially Furnished! Carport! Island Reef is a serene waterfront community, one of the few Gulf to Bay community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed) two lit tennis courts, pickleball, 2 fitness rooms, Kayak Storage, Library, Billiards, game room, clubhouse, two heated pools and Gas Grills, PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key’s popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cute brunch spots and dancing and live music every night of the week!
Listing Agent: Marlene Marshall (941-539-8850)
8773 MIDNIGHT PASS RD #302G, SARASOTA, FL 34242
$500,00083 Days on yellowkey MLS ID: A4691760
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1303 Built: 1981 Tax: $4,030 (2025)Community: Island Reef Ii Ph 1 2 & 3Condo
Taxes:$4,030
Remarks: Turnkey Furnished residence at Island Reef with two bedrooms and two baths. Laundry in residence. Furnished! Carport! island Reef is a serene waterfront community, one of the few gulf to Bay Community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed), Two lit Tennis Courts, Pickleball, 2 Fitness Rooms, Kayak storage, Library, Billiards, Game room, Clubhouse, two Heated Pools, and Gas grills. PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key's popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cute brunch spots and dancing and live music every night of the week.
6703 MIDNIGHT PASS RD #101, SARASOTA, FL 34242
$424,90077 Days on yellowkey MLS ID: A4693235
REDUCED by $15,000 (3.4%) on 06/23/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1974 Tax: $4,605 (2025)Community: Sea WindsCondo
Taxes:$4,605
Remarks: LOCATION, LOCATION, LOCATION – Live the “beach life” and a wonderful investment opportunity in beautiful Siesta Key, Florida! Enjoy your own piece of paradise at Sea Winds Condominium, Unit 101. This inviting first-floor, turnkey- “fully furnished”condo offers 2 bedrooms, 2 bathrooms, and beautiful views, all within a short walk to the world-famous beaches of Siesta Key. Meticulously decorated and thoughtfully designed, this charming condo features a comfortable living space with easy first-floor access. The unit comfortably sleeps 7 guests. The spacious primary bedroom includes a queen bed, tv, and dedicated workspace, making it ideal for remote work or extended stays. The second bedroom features a trundle bed with an additional matching twin bed, along with its own television. The living room offers additional sleeping accommodations with a queen-size sleeper sofa. The fully-equipped kitchen provides everything needed for everyday living and entertaining, while the dining area seats 6 comfortably. An adjustable coffee table offers seating for two additional guests. The unit includes a designated parking space directly in front of the condo, along with additional guest parking. Cable, water, and sewer are included in the Condo fee. Step outside to your own large, fully fenced private patio oasis featuring a Weber grill, a dining table with umbrella seating for six, and a relaxing conversation area with chairs— perfect for enjoying the Florida sunshine or entertaining guests outdoors. Residents of Sea Winds Condominium enjoy access to a heated community pool with lounge chairs, umbrellas, outdoor shower, and bathrooms for year-round enjoyment. Additional amenities include bicycle storage room, a social room for gatherings, barbeque grill and two shared laundry facilities. For added convenience, the condo also includes beach chairs, beach towels, and a rolling beach storage cart and a large storage unit on the 2nd floor. Beyond the comfort of the condominium, you are only a five-minute walk from the pristine quartz sands of Siesta Key Beach, consistently ranked among the top beaches in the United States. Spend your days soaking up the sun, strolling along the shoreline, or enjoying the spectacular sunsets for which Siesta Key is famous. Leave the light on in the condo, because when you walk back from the beach at night, it feels like a beacon calling you back. Just a short walk away, you’ll find the South Village area featuring restaurants, boutiques, beach bars, ice cream shops, and rental companies offering fishing equipment, boats, kayaks, bicycles, and passenger golf carts. A daily trolley service with stops directly in front of the Sea Winds complex provides convenient access to Siesta Key Village and other island attractions. Being well built all above Sea Level, this inviting two level complex has enjoyed being water free from any storm or hurricane since it was built. Recent community improvements include:• New roof (2024)• Newly renovated swimming pool (2025)• New storm drainage and sewer lines (2025)• Newly paved and striped parking area (2026)Do not miss this incredible opportunity to enjoy coastal living at its finest. This Sea Winds Condominium offers the perfect combination of relaxation, convenience, and adventure in one of Florida’s most sought-after beach destinations. More important though, to truly appreciate this little gem, come and see it for yourself. This unit is precious and deserves to be loved.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Sean Hickey (941-587-4244)
3820 FLAMINGO AVE, SARASOTA, FL 34242
$8,395,000236 Days on yellowkey MLS ID: A4673215
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4775 Built: 1962 Tax: $18,005 (2024)Community: Bay IslandSpa: YesSingle Family
Taxes:$18,005
Remarks: Under Construction. Incredible opportunity in highly desirable Bay Island, easy access to downtown Sarasota and Siesta beaches. Currently under construction with acclaimed Voigt Brothers construction, early 2027 completion date. Walls are up, roof is on, time to make your selections!!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Fred Sassen (404-408-5956)
5400 OCEAN BLVD #8-05, SARASOTA, FL 34242
$630,000264 Days on yellowkey MLS ID: A4670371
REDUCED by $60,000 (8.7%) on 07/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 522 Built: 1970 Tax: $6,969 (2025)Community: Beach TerraceCondo
Taxes:$6,969
Remarks: BEACH TERRACE - STUDIO GULF-FRONT RESIDENCE: YOUR PERFECT SIESTA KEY PIED-À-TERRE Discover your ideal coastal escape at Beach Terrace, perfectly positioned at the end of Siesta Key Village with direct Gulf of Mexico frontage. This charming studio residence offers the perfect pied-à-terre for those seeking an effortless weekend getaway to paradise. Whether you call Sarasota or Lakewood Ranch home, imagine having your own Siesta Key retreat just moments away, a place to unwind, recharge, and embrace the coastal lifestyle whenever you need it. The private balcony frames stunning Gulf views, while the thoughtfully designed interior maximizes space and comfort. Covered parking provides convenient, weather-protected access to your beach escape, while the residence's prime location puts you steps from all the dining, shopping, and entertainment that Siesta Key Village has to offer. No need to drive once you arrive, everything is at your fingertips. Resort-style amenities elevate the experience: enjoy the elevated heated saltwater pool with its spectacular sunset views (truly the best amenity besides the unbeatable location), stay active in the fitness center, gather in the community room, and access the world-renowned Siesta Key Beach directly from the property. The powdery white sand and crystal-clear waters are quite literally your backyard. More than a weekend residence, this is your personal gateway to the Gulf-front lifestyle. Whether it's a spontaneous Friday escape or a planned coastal retreat, your Siesta Key sanctuary awaits. This is the effortless beach lifestyle you've been dreaming of, close to home, yet worlds away.
Listing Agent: Mickey Kiernan (941-402-9115)
9000 BLIND PASS RD #303, SARASOTA, FL 34242
$799,00017 Days on yellowkey MLS ID: A4699697
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 871 Built: 1968 Tax: $5,849 (2025)Community: Fishermans CoveSpa: NoCondo
Taxes:$5,849
Remarks: Turnkey furnished and beautifully reimagined in 2024, this top-floor Gulf-front residence at Fisherman's Cove offers a rare opportunity to own one of Siesta Key's most distinctive beachfront retreats. Positioned at the quiet southern end of the island, this one-bedroom residence enjoys unobstructed panoramic views of the Gulf of Mexico from nearly every room, where turquoise waters, sugar-white sand, and breathtaking sunsets become part of everyday living. Thoughtfully renovated throughout, this residence is also the only one-bedroom floor plan in the community offering both a full bath and an additional half bath, providing added comfort and convenience for guests. Designed to maximize natural light and waterfront scenery, the open floor plan flows effortlessly from room to room. The Gulf-front terrace has been enclosed, expanding the living space while walls of impact-rated glass frame uninterrupted beach views. Soft coastal finishes, elegant tile flooring, and a fresh, contemporary palette create a relaxed yet refined atmosphere ideal for full-time living, seasonal enjoyment, or investment. The remodeled kitchen features custom cabinetry, stone countertops, newer appliances, generous storage, and an open design that overlooks the living and dining areas while keeping the Gulf as the focal point. Renovations completed in 2024 include impact windows and sliding glass doors, beautifully updated bathrooms, and quality finishes throughout, while a newer air-conditioning system installed in 2023 adds peace of mind. The spacious primary suite enjoys spectacular Gulf views through oversized windows and features an updated en-suite bath. The additional powder room is a rare feature within Fisherman's Cove, allowing guests the convenience of a separate bath while maintaining the privacy of the primary suite. Nestled between the Gulf of Mexico and Blind Pass Lagoon, Fisherman's Cove offers one of Siesta Key's most desirable waterfront settings. Residents enjoy direct beach access, a heated community pool, fishing pier, complimentary first-come boat slips, and easy access to kayaking, paddleboarding, and boating that leads to Sarasota Bay and the Gulf. The island's south end is also renowned for exceptional shelling and miles of unspoiled shoreline stretching toward Casey Key. Ideally located just minutes from Siesta Key Village, waterfront dining, marinas, and downtown Sarasota's renowned Cultural Coast, residents enjoy boutique shopping, acclaimed restaurants, theaters, galleries, Selby Gardens, and year-round entertainment. Whether you're searching for a luxurious beachfront escape, a high-demand investment with one-week rental flexibility, or a move-in-ready Gulf-front residence, this exceptional Fisherman's Cove offering delivers the very best of Siesta Key living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Roger Pettingell (941-387-1840)
5830 MIDNIGHT PASS RD #61, SARASOTA, FL 34242
$575,000244 Days on yellowkey MLS ID: A4672481
REDUCED by $23,000 (3.8%) on 07/22/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1963 Tax: $3,746 (2025)Community: Jamaica RoyaleCondo
Remarks: At its new price point, this fully remodeled beachfront villa offers something rare on Siesta Key. It is one of the most accessible ways to own on the Gulf here, with full resort amenities and real income potential. Jamaica Royale is a true beachfront community, with its own private white sand beach, three heated pools, and quiet garden pathways leading down to the shore. The interior has been completely transformed. This ground floor villa sits steps from the Gulf, where mornings begin with gentle waves and evenings settle into lingering sunsets. At a generous 728 square feet, it lives larger than most one bedroom homes on the beach, with a smart layout that makes the most of every foot. Updates include new doors and windows engineered to resist impact, a redesigned kitchen with new lower cabinets and granite countertops, an upgraded primary bathroom, and new base trim and interior doors. The furniture and appliances are all new, including the dishwasher, refrigerator, washer, dryer, AC, and water heater. Everything is ready, whether you want to move in and enjoy it or rent it out right away. Ownership here is refreshingly simple. Cable, water, and sewer are all included in association dues, so carrying costs stay predictable with no upkeep to manage. An optional rental program, run right on the property, makes it easy to generate income while you are away, with the home professionally cared for the whole time. Spend your days in a private cabana on the sand, walking the shoreline, or grilling at the beachside BBQ. When you want to explore, public transportation reaches downtown Sarasota, Gulf Gate, and Siesta Village. Whether you want a smart beachfront investment, a second home that pays its own way, or both, this villa delivers rare value on one of the most celebrated beaches in the country. Schedule your private showing and see what makes Jamaica Royale so special. A 1% RATE REDUCTION 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)
6020 MIDNIGHT PASS RD #49, SARASOTA, FL 34242
$625,00025 Days on yellowkey MLS ID: A4698693
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 834 Built: 1964 Tax: $3,492 (2025)Community: Aloha Kai AptsCondo
Taxes:$3,492
Middle School: Sarasota Middle
Remarks: Turn-Key Furnished Villa in Aloha Kai – One of Siesta Key's Premier Beachfront Communities! Welcome to your island retreat just steps from world-famous Siesta Key Beach. This beautifully updated 2-bedroom, 1.5-bath villa offers the perfect combination of coastal living, investment potential, and resort-style amenities. Whether you're searching for a seasonal getaway, full-time residence, or income-producing property, this exceptional opportunity checks every box. Thoughtfully updated, the home features a newer metal roof (2020), impact-rated windows and front door, upgraded 200-amp electrical service, a 2023 water heater, and an updated kitchen with modern cabinetry, quality countertops, and newer appliances. Offered turn-key furnished, it's ready for immediate enjoyment or rental. The first floor experienced water intrusion during Hurricane Milton. Following the storm, the owners completed professional remediation, including a fully permitted renovation and independent mold testing with negative results. Documentation is available, providing confidence in the quality of the restoration. Nestled within the lush, tropical grounds of Aloha Kai, residents enjoy private deeded beach access to Siesta Key Beach, a heated Olympic-size swimming pool, clubhouse, shuffleboard courts, beautifully maintained landscaping, and on-site management. The community permits short-term rentals, making this an attractive opportunity for both personal enjoyment and investment income. Ideally located near Siesta Key Village, waterfront dining, shopping, boating, and all that Sarasota has to offer, this is your opportunity to own a move-in-ready beach villa in one of Florida's most desirable coastal communities. Buyer should verify all room dimensions, rental policies, and community regulations with the co-op association and management.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Rex Glasson (941-587-6135)
159 VISTA HERMOSA CIR #27B, SARASOTA, FL 34242
$399,00017 Days on yellowkey MLS ID: A4698551
REDUCED by $30,000 (7.0%) on 07/18/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1971Monthly Fee: $1,104 Tax: $3,709 (2025)Community: Vista HermosaVilla
Taxes:$3,709
Remarks: ATTENTION INVESTORS, VALUE MINDED BUYERS AND HOMEOWNERS!, one of the best value for a 2 bedroom 2 bath villa currently on beautiful Siesta Key. Discover effortless island living in this beautifully updated, TURNKEY FURNISHED , maintenance-free villa on Siesta Key. Offering two bedrooms and two full baths plus its OWN CARPORT, this renovated residence is ideally located just a very short distance from the world-famous sugary sands of Crescent Beach on beautiful Siesta Key. The stylish kitchen has been refreshed with brand new appliances, and contemporary designed cabinets that is both functional and inviting. Recent upgrades also include a new HVAC system and water heater, providing year-round comfort and peace of mind. Luxury vinyl plank flooring in all bedrooms and tile throughout the unit for that extra "Clean feel", creating a cohesive look while offering lasting durability and easy maintenance. Storm windows and energy efficient throughout ( except the sliders). WASHER AND DRYER INCLUDED! Unwind in the private screened lanai, ideal setting to enjoy the gentle Gulf breezes any time of day, enhanced with an extra storage closet for all the beach toys, not to mention a laundry closet with brand new washer and dryer to boot . Both bathrooms have been tastefully remodeled with modern finishes, completing the home's move-in-ready appeal. HOA also includes water and internet service and flood insurance. The villa is conveniently situated just steps from the community clubhouse, swimming pool, outdoor grilling area. Enjoy the convenience of nearby boutiques, restaurants, and local entertainment, all within very short distance. The complimentary Siesta Key trolley provides easy transportation to Siesta Key Village, where you'll find additional shopping, dining, and vibrant island attractions. Whether you're searching for a seasonal getaway, an income-producing investment property, or a full-time coastal residence, this exceptional villa offers the perfect opportunity to experience the relaxed Siesta Key lifestyle. Schedule your private showing today and discover everything this island paradise has in store for you.
Listing is courtesy of: CP REALTY INTERNATIONAL (941-685-8441)
Listing Agent: Claude Pierre (941-685-8441)
5920 MIDNIGHT PASS RD #1003, SARASOTA, FL 34242
$1,350,000143 Days on yellowkey MLS ID: A4683544
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1334 Built: 1971 Tax: $10,983 (2025)Community: Sarasota Surf & RacquetSpa: NoCondo
Taxes:$10,983
Remarks: Great Opportunity at Sarasota Surf & Racquet Club!! Beautifully turn-key furnished 2BR/2BA condo with a split bedroom floorplan for privacy in Tower 10 Unit 3 right on the beach with a gorgeous view of the Gulf and the beautiful quartz sand beach and shoreline. The onsite rental management team takes care of your investment. You use it when you want and enjoy the great revenue stream coming your way with a rare and great opportunity to take advantage of their 3 night rental minimum policy and managing all the reservations and taking care of the upkeep and cleaning of your unit. This is really exceptional beachfront living on Siesta Key with so many resort style amenities. You have direct access to private Crescent Beach, two heated swimming pools, rental options for tents, cabanas and umbrellas, beachside and poolside BBQ grills, four pickleball courts, three tennis courts (one hard court and two Har-Tru clay) – the only clay courts for a resort community on Siesta Key. There is a fitness center on the property and a recreation room where owners can come together for fun. The interior of this unit has been re-modeled with a lovely coastal look. Both bathrooms have been beautifully re-modeled. The primary bedroom features a king size bed, large walk-in closet and has its own private vanity area and a stunning tiled walk-in shower with a seat and gorgeous glass block. The second bedroom features two queen size beds and large walk-in closet. There is a lanai/room looking out to the beach and Gulf that is perfect for a quiet space for reading or computer work. Washer and Dryer located in laundry room just steps from the unit. This resort style property has it all! Catch the trolley or walk into the Siesta Key village for great shops and lots of great casual dining or more polished dining experiences. Coastal music flows out from the open air fun places for entertainment. Come enjoy Paradise!!!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jay Mitchell Jr., Pllc (941-586-1754)
1138 SUN N SEA DR, SARASOTA, FL 34242
$1,349,00070 Days on yellowkey MLS ID: A4693618
1 Days Off yellowkey (back on 7/22/2026)
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1246 Built: 1958 Tax: $10,436 (2025)Community: Not Part Of A SubdivisionSingle Family
Taxes:$10,436
Remarks: Under contract-accepting backup offers. Rare opportunity on Siesta Key to own a fully remodeled multifamily property just moments from world-famous Siesta Key Beach. Offering two separate residences, each featuring 2 bedrooms and 1 bathroom, this property presents flexible potential for personal use, short-term rental income, or a live-in investment opportunity. Both units have been extensively updated throughout, featuring luxury vinyl plank flooring, updated electrical and plumbing, fresh interior finishes, new interior doors, and bright coastal-inspired design elements. The kitchens showcase white shaker cabinetry, quartz countertops, stainless steel appliances, and striking teal subway tile backsplashes that bring a fun yet refined coastal character to the space. Open living areas are filled with natural light from oversized windows and complemented by custom wood accent detailing. Each residence includes remodeled bathrooms, private entrances, and in-unit stacked washers and dryers for convenience. Outside, the property offers exceptional curb appeal with tropical landscaping, decorative stone accents, paver courtyard spaces, pergola detailing, and a charming gated entry. Residents and guests can also enjoy access to a nearby community pool. What’s special: guests enjoy private gated beach access through the club, with lounge chairs and umbrellas provided for effortless days on the sand. Located in one of Siesta Key’s most desirable beachside areas, this move-in-ready property offers a rare combination of style, flexibility, and investment potential in an unbeatable location.
Listing Agent: Curt Ware (941-587-9122)
6300 MIDNIGHT PASS RD #702, SARASOTA, FL 34242
$1,749,00087 Days on yellowkey MLS ID: A4692155
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1240 Built: 1970 Tax: $9,386 (2025)Community: Crystal Sands 2Condo
Taxes:$9,386
Remarks: Under contract-accepting backup offers. Set on the 7th floor of Crystal Sands, this fully updated residence offers a front-row position to the Gulf, with sweeping views stretching south along Crescent Beach toward Point of Rocks. Located in the sought-after “2” stack, the building sits just steps from the sand, creating a rare level of proximity to the shoreline with water views from every room. The 2-bedroom, 2-bath split floor plan is both functional and well-balanced, offering privacy between suites while keeping the main living space open and connected. Wide-plank flooring runs throughout, leading into a light-filled living and dining area that opens seamlessly to the Gulf beyond. A 30+ foot lanai spans the width of the residence and is accessible from both bedrooms and the main living area, creating an easy indoor-outdoor flow and a natural extension of the living space for everyday use. The kitchen is finished with shaker-style cabinetry, quartz countertops, a center island with bar seating, and stainless appliances, designed to feel clean, current, and easy to live in. Both bedrooms are well-proportioned with direct lanai access and calming water views, while the bathrooms have been thoughtfully updated with refined finishes, frameless glass showers, and cohesive tilework that carries the modern coastal aesthetic throughout the home. Residents of Crystal Sands enjoy direct beach access, a Gulf-front pool, and a prime location just minutes from Siesta Key Village’s dining and shops. With its combination of view, proximity to the sand, and updated interiors, this is one of those residences that simply works the moment you walk in.
6480 MIDNIGHT PASS RD #503, SARASOTA, FL 34242
$1,149,00075 Days on yellowkey MLS ID: N6144252
REDUCED by $50,000 (4.2%) on 07/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1979 Tax: $9,073 (2025)Community: Siesta BreakersCondo
Taxes:$9,073
Remarks: Turnkey-furnished and move-in ready, experience the ultimate coastal lifestyle in this beautifully maintained beachfront condo located on the beautiful, world-famous Siesta Key. Enjoy the soft, white sand of Crescent beach, with a Beach Attendant managing a 200 ft section of private beach. Whether you’re searching for a full-time residence, seasonal getaway, or income-producing investment property, this luxury condo offers the perfect blend of comfort, convenience, and breathtaking Gulf views. Enjoy relaxing mornings and stunning sunsets from your private screened balcony overlooking the sparkling heated pool, tropical courtyard, and turquoise waters of the Gulf of Mexico. Inside, the condo features an open and airy floor plan filled with natural light, tile flooring throughout the main living areas, and tasteful coastal finishes. The kitchen offers ample cabinetry, stainless steel appliances, recessed lighting, tray ceiling detail, and space for entertaining guests with a breakfast bar & dining area. The spacious primary suite provides a peaceful retreat with pool view, plantation shutters and sliding doors that open to the balcony. The ensuite has been updated with dual granite vanities, large walk-in shower and abundant storage. Open the sliders to the balcony for a seamless indoor-outdoor living experience. Residents and guests enjoy resort-style amenities including a beachfront heated pool, direct private beach access with free beach lounge chairs, option to rent an umbrella or cabana, beautifully maintained grounds, covered parking, grills and lighted tennis / pickleball courts. This condo also offers excellent rental potential, making it a fantastic opportunity for investors seeking vacation rental income in one of Florida’s most desirable beach destinations. Ideally located, walk to restaurants, bars, grocery, boat/bike/kayak/jet ski rentals, gift shops and more! Wake up to the beautiful beach & ocean views, where every day feels like a vacation!
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Heather Lakeman (941-412-6083)
734 BIRDSONG LN, SARASOTA, FL 34242
$1,295,00012 Days on yellowkey MLS ID: A4699745
4 Days Off yellowkey (back on 7/21/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1890 Built: 1972 Tax: $7,033 (2025)Community: Siestas Bayside Waterside SouthSpa: NoSingle Family
Taxes:$7,033
Remarks: Under contract-accepting backup offers. Luxury Coastal Contemporary Home all on the first floor with no stairs anywere...This 3 Bedroom Pool Home on Siesta Key offers an Oversized Primary Bedroom with a ensuite bathroom, large roll in shower, Two custom closests, seperate den/workout room looking over the heated pool. Two additional oversized Bedrooms one with a King bedroom set and the other with a Queen and two twins which sleeps 4 or can be modified to a king bedroom also Custom closets and smart tv's. Beautifully appointed and fully turnkey furnished, this exceptional residence features an open and inviting floor plan with designer finishes, spacious living areas, and a fully equipped kitchen with stainless steel appliances. Step outside to your own private tropical paradise, complete with a sparkling pool, outdoor covered dinnig and a Grill area, lush landscaping, and a beautifully maintained backyard designed for relaxing or entertaining. Whether you're enjoying your morning coffee by the pool or hosting friends for an evening under the stars, this outdoor space is truly spectacular. Additional features include a 2-car garage,outdoor shower, in-home laundry, ample storage,a second french door refrigerator with a cafe ice maker and everything needed for year-round living. Ideally located just minutes from Siesta Key's world-famous beaches, fine dining, shopping, marinas, and downtown Sarasota, this home offers the ultimate Florida lifestyle. Luxury at its best—this exceptional Siesta Key home offers the perfect opportunity to enjoy year-round island living in one of Florida's most desirable locations. A must see!
Listing is courtesy of: WILLIAM RAVEIS - FLORIDA LLC (941-867-3901)
Listing Agent: Bob Mcgrath (941-628-1069)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.