Location: Sarasota , 34242
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1200 E PEPPERTREE LN #307, SARASOTA, FL 34242
$699,00050 Days on yellowkey MLS ID: A4683608
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1466 Built: 1973 Tax: $7,547 (2025)Community: Peppertree Bay IiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,547
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Set within Peppertree Bay on Siesta Key, 1200 E Peppertree Lane #307 offers a well-proportioned, turnkey, move-in ready two-bedroom, two-bath residence encompassing 1,466 square feet. The interior presents a bright, open layout anchored by a spacious great room, where crown molding, tile flooring throughout, and an expansive wall of impact glass windows create an airy, light-filled living environment. The adjoining dining area flows seamlessly into the kitchen, reinforcing the home’s functional, connected design. The kitchen features a tray ceiling with inner crown molding, recessed lighting, abundant wood cabinetry, granite countertops, a tile backsplash, and a full suite of stainless-steel newer Whirlpool appliances. A breakfast bar provides additional prep and serving space, supporting both everyday living and casual entertaining. The primary bedroom is generously scaled and benefits from strong natural light, crown molding, a walk-in closet, and direct access to the enclosed sunroom. The primary bath includes a granite-topped vanity, glass-enclosed walk-in shower, linen storage, and updated fixtures. A well-sized guest bedroom with an oversized window alcove and a nearby full bath maintains privacy and flexibility for visitors. An enclosed sunroom lined with windows extends the living space, offering versatility as a lounge, office, or secondary sitting area. A stacked washer and dryer are conveniently positioned within a dedicated closet. Newer HVAC system (2024) and Water heater (2025). Peppertree Bay is a Gulf-to-Bay community providing private deeded beach access, a fishing pier, two resort-style heated pools, clubhouses, a fitness center, saunas, tennis and pickleball courts, covered under building assigned parking with this unit that provides a bicycle rack and unit storage, and multiple outdoor gathering areas. This building has newer elevators along with stairwell access, with the building roof being replaced in 2020. The location places residents directly on Siesta Key, home to Siesta Beach, consistently ranked the #1 beach in the United States by TripAdvisor, further underscoring the appeal of both the setting and lifestyle offered by this residence.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Sharon Chiodi (941-809-0380)
6140 MIDNIGHT PASS RD #A10, SARASOTA, FL 34242
$839,000155 Days on yellowkey MLS ID: A4671897
REDUCED by $10,900 (1.3%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1967 Tax: $7,853 (2024)Community: Horizons WestVilla
Taxes:$7,853
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Are you looking for new? Welcome to your fully renovated, turnkey Siesta Key villa, where everything is new from top to bottom! On the Gulf side with direct beach access, this stunning two-bedroom, two-bath coastal retreat has been beautifully transformed into a modern beachside haven. Every detail has been redone with quality and style, such as new kitchen, furnishings and décor, ready for you to move right in and start living your best island life. In the sought-after Horizons West community, this villa offers the ideal blend of comfort and convenience. Enjoy two community pools (one right on the sand and one near your door), along with beach access. Whether you’re seeking a personal getaway or a high-performing investment property, this villa checks every box, and it’s part of a rental program with flexible leasing options and an on-site manager. Experience the ultimate Siesta Key lifestyle, close to Siesta Key Village, where you’ll find vibrant restaurants, boutique shops and nightly entertainment. Or head just minutes away to downtown Sarasota for arts, dining and culture. Own your piece of paradise today, new, beautiful and next to the #1 beach in the world.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Jaci Krawtschenko (941-284-3789)
9011 MIDNIGHT PASS RD #228, SARASOTA, FL 34242
$399,0001101 Days on yellowkey MLS ID: A4566083
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 783 Built: 1974 Tax: $4,116 (2022)Community: Sunrise Cove Sec 4Condo
Taxes:$4,116
Tax Year: 2022
Remarks: The Lowest Entry Price on the Water! Investor Alert: This is the lowest-priced condo currently available in Sunrise Cove, making it the absolute best entry price for a highly desirable waterfront investment on Siesta Key. Direct Intracoastal Waterway views from your lanai, living area, and bedroom. Enjoy sunrises over Little Sarasota Bay and sunsets at Turtle Beach (deeded beach access across the street). Fully furnished 1-bedroom, 1-bathroom unit featuring an updated kitchen (stainless steel appliances) and a custom-built queen Murphy Bed for maximum sleeping capacity. Rental Income Generator: Community allows lucrative one-month rentals with convenient on-site management Unbeatable Amenities • 2 bayside heated pools • Lighted tennis and pickleball courts • Large clubhouse with fitness rooms and billiards • Boat docks available for a low yearly fee • Adjacent to Turtle's Restaurant and Ophelia's Restaurant • Free trolley stop across the street for easy access to Siesta Key Village and Public Beach. Secure your piece of Siesta Key waterfront real estate at a game-changing price!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Maurice Menager (941-238-8119)
915 SEASIDE DR #407, SARASOTA, FL 34242
$2,900,000193 Days on yellowkey MLS ID: A4667661
0 Days Off yellowkey (back on 2/10/2026)
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2255 Built: 2009 Tax: $15,444 (2024)Community: Siesta Key Beach Residences IiCondo
Taxes:$15,444
Remarks: Experience luxury living at the highly-regarded Hyatt Beach Residence Club of Siesta Key! This stunning 4th-floor condominium boasts 3 bedrooms and 3.5 baths, offering incredible Gulf Views for breathtaking sunsets from your private balcony. From the moment you enter through the elegant foyer, you’ll be transported to a tropical paradise. Every detail in this home has been meticulously designed to create a sense of comfort and sophistication. The master suite is a true sanctuary, featuring a spa-like bath and private access to an outdoor terrace that overlooks the powdery quartz sand beaches of Siesta Key. The deluxe chef’s kitchen is a culinary enthusiast's dream, equipped with top-of-the-line appliances, including a wine refrigerator, making it perfect for entertaining guests. Unwind at the beachfront pool, complete with private cabanas, a hot tub, and a cozy fire pit. Indulge in food and drinks at the Tiki Bar, or head straight to the beach and take advantage of the resort’s paddleboard and beach chair services. The waterfront terrace features a Ping Pong and billiards table, ensuring fun-filled days. Hyatt hospitality is renowned for its legendary concierge services, offering a front desk staff, valet parking, and 24-hour security. Electric charging stations are conveniently located on-site. NIGHTLY RENTALS are permitted, providing an excellent investment opportunity. An onsite program director is available to offer recommendations for recreational activities, and residents have access to an indulgent spa facility and fitness center featuring a steam room. The condo fee covers ALL YOUR MONTHLY EXPENSES, including cable, electric, gas, and water. Plus, enjoy complimentary breakfast each morning! Located just a short distance from Siesta Key Village, you'll find a vibrant array of shopping and dining options, making it the entertainment hub of the island. Proximity to the cultural arts of downtown Sarasota and St. Armand's Circle means even more fantastic dining and shopping experiences right at your fingertips. Don’t miss out on this extraordinary opportunity to own a piece of paradise!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Brian Ward (941-650-7721)
5830 MIDNIGHT PASS RD #T22, SARASOTA, FL 34242
$1,000,0008 Days on yellowkey MLS ID: A4689210
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1194 Built: 1967 Tax: $8,543 (2025)Community: Jamaica Royale Elev AptsCondo
Taxes:$8,543
High School: Riverview High
Remarks: Rare opportunity - Jamaica Royale, Tower 1 Enjoy breathtaking Gulf views from this beautifully positioned second-floor Gulf front condo on world-famous Siesta Key Beach. This 2-bedroom,2-bathroom residence features light-filled open living and dining space. The generous areas flow effortlessly toward the Gulf creating the perfect setting for relaxed coastal living or entertaining guests. Enjoy spectacular sunsets from the expansive balcony accessible from both the living room and primary suite. Ideally located just minutes from the island's vibrant restaurants, boutique shopping and entertainment, this Jamaica Royale beauty is a MUST SEE! Whether as a primary residence, a beach retreat or an investment opportunity this condo offers the best in Gulf front living.
Listing Agent: Alana Kate Sudano (410-456-8783)
5353 SHADOW LAWN DR, SARASOTA, FL 34242
$933,0001 Day on yellowkey MLS ID: A4690427
0 Days Off yellowkey (back on 4/18/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1596 Built: 1960Monthly Fee: $17 Tax: $4,260 (2025)Community: Siesta IslesSingle Family
Taxes:$4,260
Remarks: Under contract-accepting backup offers. With NO WATER DAMAGE OR WATER INTRUSION, you can have peace of mind that you are getting a MOVE IN READY piece of tranquility on the beautiful, world renown island of Siesta Key. Being offered Turnkey Finished negotiable, you are ready to move in and get to relaxing on this spacious lot of over a quarter acre of high and dry land. You will find yourself in a 3-bedroom, 2- bathroom ranch style home with an extra bonus room for friends and family. It has an attached one car garage with a nice extension for storage of bikes and beach items. A key part of this home is that it has an oversized portico in front of the home making it easy to unpack the car out of the rain and in the shade on beautiful Florida sunny days. This home comes with its own caged and heated pool overlooking the extremely private backyard that backs up to a park preserve so you will never have anyone built behind you. This tropical backyard is basically maintenance free with no grass to mow a very peaceful filtered Koi Pond. The property’s tropical landscaping is full of lighting and is watered by a well-fed irrigation system which also automatically fills the pond. It’s as easy as that! Inside the beautiful home you will find an open floor plan with premium tile floors and kitchen offering granite countertops and upgraded soft closing cabinets and drawers. This property has had the water and drainage pipes fully re-piped with PVC, has new A/C ducting, and an upgraded electrical box with a 200-watt service amp. The best part about this property is it is a short bike ride to the famous Siesta Village and .8 miles from the Public Parking Lot to Siesta Key Beach! You can get to both places without ever stepping a foot on the main roads. Schedule a showing today to the one-of-a-kind listing that you could call HOME!
Listing is courtesy of: IRONGATE REALTY INC (941-720-1003)
Listing Agent: Brittany Mccord (941-720-2640)
711 BEACH RD #408, SARASOTA, FL 34242
$1,049,9999 Days on yellowkey MLS ID: A4689303
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 782 Built: 1969 Tax: $6,301 (2025)Community: Sunset RoyaleCondo
Taxes:$6,301
Remarks: **This is the One! Coastal Contemporary Beachside Living!** Welcome to the stunning Penthouse-level, 4th-floor residence at Sunset Royale with beautiful unobstructed Gulf-facing views! Enjoy every sunrise and sunset! Ideally positioned just across the street from world-renowned Siesta Key Beach. This truly move-in ready condo has been beautifully renovated throughout, offering a light-filled coastal interior and effortless flow. The kitchen is a true centerpiece, featuring high-end quartz countertops and backsplash, a large waterfall-edge island, solid wood custom cabinetry, and newer appliances (approximately 2 years). The open layout flows seamlessly into the living space with a fantastic accent wall and out to the balcony, where you can enjoy sweeping Beach/Gulf views. Additional highlights include an in-unit washer and dryer, a newer water heater, and a beautifully updated bathroom with a walk-in shower. A thoughtfully designed welcome area inside the unit provides a perfect arrival space with games, guides, and local information. This property also features an owner's storage unit ideal for beach chairs and gear, a designated parking space, and convenient building amenities including garbage chutes on both sides and two on-site grills available at no charge to owners and guests. Cable is included in the HOA fee, and the building features a new roof put on in 2025. Flexible ownership options allow for **7-day rentals or longer**, with on-site management available through Prime Vacations (optional, not required). Whether for personal use or investment, this penthouse residence delivers the ultimate in convenience, comfort, and location in the heart of Siesta Key! A short stroll to Siesta Key village and only a few steps out to the beautiful white sandy beach! Reach out today to schedule your own private tour!
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Ryan Miller (941-954-6925)
6334 MIDNIGHT PASS RD #41, SARASOTA, FL 34242
$629,00011 Days on yellowkey MLS ID: A4688750
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 612 Built: 1962 Tax: $3,759 (2025)Community: Siesta RoyaleSpa: NoCondo
Taxes:$3,759
Remarks: Siesta Royale is a Beachfront complex on Siesta Key located on the world famous Crescent Beach. This unit is Located right by the pool and close to the beach. This unit has been updated with High end laminant flooring throughout, new appiances, Granite counters and all new impact windows with beautiful finishing touches that makes you feel like you are really on vacation. Perfect for investment or full time use, Parking right outside unit, No stairs. This complex is close to many retaurants, boating, parasailng and shopping. This unit has a good rental histoy with steady rentals though out the year. Dont miss this one.
Listing Agent: Tom Ward (941-350-2463)
5026 CALLE MINORGA, SARASOTA, FL 34242
$990,0001 Day on yellowkey MLS ID: A4690532
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1240 Built: 1954 Tax: $11,005 (2025)Community: Mira Mar ExitSingle Family
Taxes:$11,005
Remarks: RARE OPPORTUNITY IN SIESTA KEY VILLAGE! This charming cottage-style property is ideally located in the heart of Siesta Key Village, just steps from world-renowned Siesta Beach, boutique shopping, and vibrant dining. Zoned OPI (Office, Professional, Institutional), this versatile property offers endless potential for professional office use, boutique business, or residential conversion (buyer to verify). Offered TURN-KEY FURNISHED, this property is move-in or business-ready from day one—an incredible advantage for buyers seeking a seamless transition. Featuring 3 bedrooms, 1 bathroom, a full kitchen, and a spacious Florida room, the layout provides flexibility for a variety of uses. The property has been freshly painted and is move-in ready, with a metal roof approximately 8 years old. A new shell driveway offers convenient on-site parking, a rare find in the Village. Enjoy a peaceful, private setting while being right in the center of it all—ideal for professionals such as attorneys, architects, therapists, consultants, or anyone seeking a unique live/work opportunity in one of Sarasota’s most desirable locations. Don’t miss your chance to own a piece of Siesta Key Village with unmatched walkability, flexibility, and income-producing potential.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Kim Donahue (941-724-2587)
3458 ANGLIN DR, SARASOTA, FL 34242
$2,595,00057 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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Barbara May (404-822-9264)
5740 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,950,0001 Day on yellowkey MLS ID: A4686166
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $12,418 (2025)Community: Gulf & Bay Club Ph 6Spa: YesCondo
Taxes:$12,418
Remarks: A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Drew Jacobsen (941-253-6309)
6154 MIDNIGHT PASS RD #A13, SARASOTA, FL 34242
$615,40040 Days on yellowkey MLS ID: A4685497
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 875 Built: 1966 Tax: $4,775 (2025)Community: Casa Blanca VillasVilla
Taxes:$4,775
Remarks: Larger two-bedroom gulf-side stand-alone villa in Casa Blanca--the gem of gems--and rarely available 980 total square feet floor plan. Just a few steps from the pure, fine, white quartz sand of Siesta Key Beach, great restaurants, shopping, and entertainment. New CUSTOM DESIGN renovation, carefully planned and completed on January 30, 2026. Larger kitchen, stainless steel appliances, quartz countertops, separate dining nook, custom cabinetry, and new luxury vinyl tile flooring inside. The south-facing, screened lanai, with a composite floating floor, invites sunshine and warmth inside. Turn-key furnished and equipped. Wonderful on-site rental management office with approximately $40,000 yearly rental income in 2021-2023. No details overlooked: 110-volt EV charger installed outside and wired for 220 volts; PVC plumbing lines replaced, electrical outlets raised; new raised water heater, HVAC air handler and condenser, new ducts. HVAC 2023. Casa Blanca is well-appointed community on the island, with the South Siesta Village and the Siesta Key Village just a short walk away, with charming shops, restaurants, and nightlife. Enjoy the pool, clubhouse, fitness center, yoga on the beach nearby, and the local cuisine. Casa Blanca Unit A13 is the top-of-the-line villa. Own your own piece of Siesta Key's paradise.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Linda Holley (941-914-4914)
137 AVENIDA MESSINA #1, SARASOTA, FL 34242
$620,000156 Days on yellowkey MLS ID: A4671658
REDUCED by $45,000 (6.8%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1966 Tax: $6,247 (2024)Community: Villa NavarraCondo
Taxes:$6,247
Remarks: Centrally located and fully furnished! Located within the boutique condominium community of Villa Navarra on Siesta Key, this fully updated, turnkey-furnished ground-floor residence offers an exceptional blend of quality, comfort, and convenience. The property is ideally situated one block from Siesta Key Village and approximately two blocks from Siesta Beach, providing easy access to the island’s most popular destinations. Ideal for full time, snow birds or people looking to lease this condo out to renter's for the two month minimum. The residence features two bedrooms and two full bathrooms arranged in an open, functional layout. The spacious living and dining areas flow seamlessly into a thoughtfully renovated kitchen appointed with solid-surface countertops, modern cabinetry, and stainless-steel appliances. Finishes and flooring throughout the home have been carefully selected to create a clean, contemporary aesthetic that complements its coastal setting. The primary suite includes an en-suite bath and generous closet space, while the guest bedroom is conveniently located near the second full bath. The ground-floor design allows direct access to the assigned parking space for added ease. With extensive updates and attention to detail, this residence is move-in ready and designed for practical, comfortable living. Villa Navarra is a well-maintained, low maintenance community of just sixteen units surrounded by tropical landscaping and a relaxed island atmosphere. Residents enjoy convenient access to the free Siesta Key trolley and can easily walk to Siesta Key Village, offering a wide variety of local dining, shopping, and entertainment options. The renowned quartz sands and turquoise waters of Siesta Beach are only a short stroll away. This property is well-suited for a full-time residence, seasonal getaway, or long-term rental investment. Its location, quality, and turnkey condition make it a rare opportunity to enjoy the Siesta Key lifestyle within a private and beautifully maintained setting.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jeffrey Bray, Pllc (941-718-1213)
6157 MIDNIGHT PASS RD #A51, SARASOTA, FL 34242
$350,00045 Days on yellowkey MLS ID: TB8482718
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 690 Built: 1974 Tax: $3,852 (2025)Community: Bay OaksCondo
Taxes:$3,852
Remarks: Looking for a vacation home that also produces income? This one is for you! A charming updated GROUND floor condo featuring 2 rentable bedrooms and 1 bathroom making this the LOWEST priced unit in the Bay Oaks complex. This unit comes completely furnished, allows short term 1 WEEK RENTALS and already has a high rating and excellent cash flow with VRBO #911238. The condo is equipped with a full kitchen and reserved covered parking, a water view from the lanai and is located in beautiful Siesta Key, Florida. This particular unit is located about 30 feet from the intracoastal waterway, so soak up pristine gulf views right from your own lanai! It is also a stone's throw away from the community's heated pool. The unit was refreshed with an updated bathroom, kitchen, lanai tile and added insulation for efficiency and sound dampening. The Bay Oaks community amenities include a heated pool, tennis court, dock on the bay, fishing pier, community barbecue grill, community billiard room, 1 parking space (and access to additional visitor space) and all common area and outdoor maintenance. Internet, water, and trash are also included in the fee. The community is on the Siesta Key trolley line with a stop right out front. Located near the vibrant Sarasota nightlife, upscale shops and dining options, there's always something to explore. Did I mention Siesta Key was named #1 beach in AMERICA and 4th in the WORLD? Its nearly 99% quartz-crystal powdered sand, dubbed the “world’s finest, whitest sand”, never gets hot under the Gulf Coast sun and tropical weather. The 2016 $20 million-dollar renovation added a new playground, two concession stands, more restrooms, a half-mile long esplanade, many shelters and pavilions, and a renovated Sarasota School of Architecture pavilion. With 950 free parking spaces, this venue provides the most parking for any public beach in Sarasota County. You will want to check this out for yourself. Book a week vacation and explore before you buy or book a single showing. Either way, you won't be disappointed.
Listing is courtesy of: TAM BAY REALTY LLC (813-493-2913)
Listing Agent: Natalie Spencer (813-417-7331)
5880 MIDNIGHT PASS RD #906, SARASOTA, FL 34242
$1,150,000169 Days on yellowkey MLS ID: A4670194
REDUCED by $45,000 (3.8%) on 04/16/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1642 Built: 1982 Tax: $7,217 (2024)Community: CasarinaCondo
Taxes:$7,217
Remarks: The least expensive unit in the sought-after Casarina on Siesta Key with another price reduction of $50,000! This Top-floor unit offers stunning views of Siesta Beach and all the comforts of home. The interior has been tastefully updated with modern finishes and stylish decor. The unit is being sold furnished (minus few staging items). The kitchen has newer cabinets and upgraded appliances. Enjoy the spaciousness of the living/dining combination area and be drawn to the expansiveness of the enclosed patio where you can enjoy evening sunsets. The 17-by-12-foot primary bedroom has luxury vinyl flooring and room for a small desk area. The primary bath has new vanities, mirrors and lighting. Casarina has seven acres of newly planted tropical landscaping and 200 feet of private beach. The main lobby has recently been updated. Spend your days swimming in the heated pool, soaking in the spa, playing tennis, pickleball, basketball or simply enjoying the quiet beauty of the #1 Siesta Key Beach. With covered parking, a secure lobby and an on-site manager, everything you need is right here. Enjoy being close to the shops and restaurants of Siesta Village and only minutes from downtown Sarasota’s arts, dining and world-class healthcare. This is your chance to own and live in beautiful Sarasota. Owner has paid all the present assessments for the new upgrades to the property and building.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Robert Sherman (941-313-1301)
8977 MIDNIGHT PASS RD #222, SARASOTA, FL 34242
$589,900104 Days on yellowkey MLS ID: A4676582
58 Days Off yellowkey (back on 4/17/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1093 Built: 1974 Tax: $5,552 (2025)Community: Sunrise Cove Sec 3Condo
Taxes:$5,552
Remarks: Under contract-accepting backup offers. Luxury Waterfront Living Spectacular Views, Resort-Style Amenities Wake to breathtaking sunrises over Little Sarasota Bay and the Intracoastal Waterway. This fully remodeled and furnished 2-bedroom, 2-bath condo offers 1,093 square feet of refined coastal living where the views are the true centerpiece. The Residence Thoughtfully renovated in 2024, this residence blends the modern finishes with timeless coastal elegance. The open living and dining areas are bathed in natural light and perfectly positioned to capture sweeping water views, creating an inviting space for both everyday living and entertaining. Features include: 2 Bedrooms, 2 Bathrooms 1,093 Square Feet Panoramic Bay & Intracoastal Views Luxury Vinyl Flooring (2024) New Stainless-Steel Appliances (2024) New Hot Water Heater (2024) New A/C System (2025) Quartz Countertops Offered Fully Furnished with Upscale Furnishings & Accessories Move-In Ready Resort-Style Waterfront Community Enjoy an amenity-rich lifestyle designed for relaxation, wellness, and recreation: Tennis & Pickleball Courts Two Heated Pools-Including an Olympic-Size Pool with Lap Lanes Clubhouse with Pool Table and Ping Pong Fitness Center with Weight & Exercise Equipment Boat Docks Available for Lease Waterfront Setting with Direct Intracoastal Access An Unmatched Coastal Location Turtle Beach directly across the road Shuttle stop providing easy access to Siesta Beach and Siesta Village World-class beaches, boating, dining, and shopping just minutes away The Lifestyle This home is all about the views- sparkling water, passing boats, and unforgettable sunrises enjoyed from the comfort of your living space. Whether as a primary residence, seasonal retreat, or investment property, this condo delivers a luxury waterfront lifestyle with effortless ease.
Listing is courtesy of: PETER D DONAHUE LICENSED REAL ESTATE BROKER (239-206-0740)
Listing Agent: Peter Donahue (239-206-0740)
5045 OXFORD DR, SARASOTA, FL 34242
$3,999,00050 Days on yellowkey MLS ID: A4681817
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3850 Built: 1950 Tax: $21,230 (2025)Community: Siesta BeachSpa: YesSingle Family
Taxes:$21,230
Elementary School: Southside Elementary
Middle School: Sarasota Middle
Remarks: Exceptional new waterfront offering on the Grand Canal of Siesta Key. Located on a quiet, picturesque canopy road, this coveted property delivers deep-water boating, and a new 31' dock and 10,000 lb. lift. Rare 100' stretch of unspoiled waterfront frontage. Quick access to Sarasota Bay and the Gulf. Designed for elevated coastal living, the residence offers expansive living areas, elegant finishes, and seamless indoor-outdoor flow ideal for entertaining and everyday luxury. Positioned on a double lot, with a stately motor court surrounded by opulent landscaping, the home offers a welcoming atmosphere. The kitchen is expansive, beautifully redesigned, and built for hosting large gatherings; a Culinary Haven with a Chef's Island as the centerpiece, complete with top-of-the-line appliances, including a Wolf 6-burner gas range, a Sub-Zero refrigerator, and a secondary Sub-Zero refrigerator is also included. A nugget ice maker, and wine fridge in the dining room's dry bar sets the tone, with a luxurious dining room offering a large space for dinner parties, also could double as a formal living room. There are two primary suites, one downstairs, and one upstairs. The downstairs suite is perfect for guests or an in-law unit. The second-floor primary suite is a private retreat, elevated above it all and wrapped in natural light. Large windows frame tranquil canal views and lush, mature landscaping, creating a serene, tree-lined outlook that feels both peaceful and secluded. The main primary bath, a dream en-suite bath, a luxurious area that incorporates dual sinks, a rainfall glass enclosed shower, separate soaking tub, and private water closet. A voluminous walk-in closet, with a built-in vanity, acts as the quintessential, functional anchor. An additional 1 to 2 guest bedrooms on the second floor, with a 4th full bath. 2nd floor loft/game room is a perfect room for a getaway, or read a book on its outdoor terrace. Back downstairs is a home office, a private workspace. The first floor family room is a large media room with sliders to access the lanai, and the two-story pool cage that will be a family favorite, with its salt water pool and spa. Step outside and fire up the grill. The expansive outdoor living area is designed for effortless gatherings and all-day enjoyment. An outdoor kitchen with a built-in grill, and eat-up bar, allows for making it easy to host everything from casual lunches to evening cookouts. Multiple table spaces offer comfortable shaded seating, perfect for dining, games, or lingering conversations. Completely renovated estate. This beautiful home is essentially brand new. A grand space that's Just minutes from the sugar-sand shores of world-famous Siesta Key Beach, once again voted the number 1 beach in America by TripAdvisor, along with premier dining, night life at Siesta Key Village, and endless boutiques for shopping. One of Siesta Key's most desirable waterfront locations. Come experience a serious boater's dream come true!
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Darren Beddoe (407-353-8810)
6518 MIDNIGHT PASS RD #209, SARASOTA, FL 34242
$850,000143 Days on yellowkey MLS ID: A4673460
REDUCED by $25,000 (2.9%) on 04/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1215 Built: 1975 Tax: $8,542 (2024)Community: House SunCondo
Taxes:$8,542
Remarks: Experience true beachfront living on world-famous Siesta Key. This turnkey-furnished 2-bedroom, 2-bath residence offers an exceptional opportunity to own along Siesta Key’s shoreline, combining Gulf views with impressive short-term rental income potential. Located just steps from the island’s iconic powder-white sand, this inviting condominium is designed for comfort, convenience, and effortless coastal living. Inside, an open and airy layout welcomes you with abundant natural light and luxury vinyl flooring throughout the main living areas. The living room flows seamlessly to large sliders that open to a wonderful 14x7 private patio, the perfect place to relax and take in the stunning views of the Gulf of Mexico. Kitchen features wooden cabinets providing lots of ample storage, a breakfast bar for additional seating, and a functional layout ideal for everyday cooking or hosting guests. The primary suite includes ceramic tile flooring, a private en-suite bath, and ample closet space. Both bathrooms have been updated with new vanities and granite countertops—the primary bathroom offering a standalone shower, while the guest bathroom features a convenient tub/shower combination. Every window and sliders have recently been replaced by association in the last few years This community is one of the few on Siesta Key allowing weekly rentals, paired with a professional on-site rental management team, creating strong income potential while still giving you the freedom to enjoy your own beach retreat. Resort-style amenities elevate the beachfront experience. Enjoy a beach-facing pool and tennis courts, fitness center, rooftop lounge with panoramic Gulf views, and outdoor grilling/bar areas with firepits—everything you need for relaxed days and evenings by the water. Direct beach access places you just steps from the shoreline. Ideally located near Siesta Key Village’s vibrant shops, dining, and entertainment, this residence offers the perfect combination of coastal living, convenience, and investment appeal—an outstanding opportunity to enjoy and share the Siesta Key lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: David Leventhal (941-518-7694)
5302 LAS ROSAS, SARASOTA, FL 34242
$725,000262 Days on yellowkey MLS ID: A4659614
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1184 Built: 1962Monthly Fee: $4 Tax: $3,190 (2024)Community: Sarasota BeachSingle Family
Taxes:$3,190
Remarks: Welcome to Palm Island, the Heart of Siesta Key!! Palm Island is an Island on an Island, located a short walk to World Famous Sugery Sands of Siesta Key Beach (Beach Access 10) and Siesta Village. With only one small humpback bridge on & off, this beachy neighborhood is a quiet oasis that is close the beach, restaurants and nightlife that makes this area so desirable. Great opportunity to build your dream home or use the current home as an investment or just enjoy the Island lifestyle. Current home has 2 bedrooms, 2 baths and a 2-car garage. Terrazzo floors throughout. The fenced back yard is a Tropical Paradise for taking in the soothing Gulf Breeze.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Dan Miller (941-376-7442)
603 TREMONT ST, SARASOTA, FL 34242
$3,690,00031 Days on yellowkey MLS ID: A4685407
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3996 Built: 2025 Tax: $7,175 (2025)Community: Waterside-Wood Siestas BaysidSingle Family
Taxes:$7,175
Remarks: Perfectly positioned in the heart of Siesta Key, this masterfully crafted New Construction estate epitomizes modern luxury and architectural brilliance. This ultimate entertainment home provides 3,996 square feet of exquisitely designed living space with 4 bedrooms, 4 full bathrooms, 1 half bath, an office, and an upstairs second living room area. From the moment you step inside, you are greeted by a breathtaking open-concept layout accentuated by soaring 20-foot ceilings, floor-to-ceiling glass windows, and sleek porcelain tile flooring, all bathed in natural light and overlooking the lushly landscaped grounds. The state-of-the-art chef’s kitchen is a masterpiece of both style and function, featuring top-of-the-line Monogram appliances, quartz countertops, custom cabinetry, walk-in butlers pantry, and wine display, seamlessly flowing into the luxurious living and dining areas. Designed for an effortless indoor-outdoor lifestyle, this home boasts multiple rooftop decks, two spacious patios, and a resort-style outdoor oasis complete with a fully equipped summer kitchen, built-in grill, pool, and hot tub spa. The primary suite is a private retreat, offering a tranquil terrace, expansive walk-in closet, and a spa-like ensuite with a soaking tub, glass-enclosed shower, and designer finishes. As you ascend the grand staircase to the upper level of the lavish property, you are greeted with a breathtaking sight of three cozy bedrooms, each with its own private ensuite bathroom and featuring private access to a rooftop deck, creating the ultimate serene escape. A second laundry room is conveniently located upstairs to service the secondary bedrooms. Elevating the home’s sophistication, additional highlights include a electric fireplace, custom walk-in closets, high-end quartz cabinetry, and a private elevator for seamless access to every level. This newly built residence offers peace of mind with the latest in building codes, energy efficiency, and storm protection. Modern insulation, impact-rated windows and doors, and up-to-date mechanical systems translate into lower utility bills, reduced maintenance, and enhanced safety. You’ll also benefit from turnkey readiness—no need for costly renovations or updates. Just moments from world-renowned Siesta Key Beach, fine dining, and premier shopping, this extraordinary residence offers an unparalleled combination of tranquility, elegance, and modern convenience. Your dream coastal retreat awaits—contact us today for a private tour!
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
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