Location: Sarasota , 34242
Do Not Show Listings
1250 N PORTOFINO DR #304, SARASOTA, FL 34242
$428,000364 Days on yellowkey MLS ID: A4649477
REDUCED by $10,000 (2.3%) on 04/15/2026
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 780 Built: 1969 Tax: $3,898 (2024)Community: Siesta Harbor IiCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$3,898
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Looking for a home for your boat, a beach lifestyle, or an investment? Enjoy sunrises over the marina, afternoons on Siesta Key Beach, and evenings on your enclosed balcony overlooking the boats and colorful skies. This furnished 1BR/2BA condo in Siesta Harbor is beautifully updated with an open floor plan, luxury vinyl flooring, remodeled kitchen (2022) with white shaker cabinetry, granite counters, glass backsplash, peninsula seating, and stainless appliances. Bathrooms feature quartz vanities and tiled showers; guest bath includes a soaking tub. Impact windows, same-floor laundry, and private storage add convenience. Siesta Harbor, a 55+ community, offers private beach access, heated pool/spa, lush landscaping, fishing pier, and a full calendar of social activities. Dock leases may be available for boats up to 30’. Additional amenities include covered parking, on-site manager, and a new roof (2025). Ideally located off the South Bridge near dining, shops, and the free Siesta Key trolley, this turnkey condo is perfect as a vacation retreat, full-time residence, or investment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Marci Mcfarland (941-961-3390)
527 FREELING DR, SARASOTA, FL 34242
$5,825,000123 Days on yellowkey MLS ID: A4669657
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 4310 Built: 2026 Tax: $6,458 (2024)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$6,458
Remarks: Under Construction. The exterior presentation of this spectacular waterfront residence is most impressive with its blend of modern architecture and refined luxury. With superior elevation high above the water’s edge on Siesta Key’s prestigious Bay Island, this new to-be-built 4,310 sq. ft. residence is an unparalleled oasis of tranquility in a breathtaking setting. A place where architectural elegance and natural beauty converge in perfect harmony with elaborate artisanal work, functional design, and top-tier amenities. For boaters, the location is ideal with a new seawall and a private dock allowing quick access to the bay and gulf beyond. Built with intention and quality, large windows flood the space with natural light illuminating the graceful enhancements within. When entering the home through the 4-car garage, an elevator takes you to the first and second living levels. An elegant foyer entry with double-height ceiling and sleek iron-railed staircase usher you into the spacious interiors where every detail, from the fluid layout to the custom finishes, is thoughtfully curated. Adding a distinctive touch to the stunning great room are 20-foot ceilings and a two-story entertainment wall flanked by artistic display niches. A wall of glass sliders sets a dramatic tone, framing water views and uniting indoor-outdoor living. Designed for effortless entertaining and timeless family gatherings, the outdoor area overlooks the water to create a tranquil setting that feels both secluded and well-connected. With nearly 500 sq. ft. of covered lanai, an outdoor cook center and a heated pool/spa, there’s ample opportunity for hosting special gatherings or simply enjoying the quiet beauty laid before you. Lovely landscaping, lush greenery and outdoor spaces add to the home's overall aesthetic appeal. A remarkable gourmet kitchen is designed for functionality and style, equipped with high-end finishes, top-tier appliances, a large island and a butler’s pantry with additional refrigerator and dishwasher. An adjoining dining room comfortably seats 8-10 and offers wonderful water views while dining. The primary wing is remarkable with an exquisite spa bath, enlarged customized wardrobe room, and direct access to the laundry facilities. The first level also includes a den suite ideal for remote work or creative pursuits and a completely private guest bedroom with its own full bath. Upstairs, there’s an overlook to the great room below, 2 bedrooms, 2 full baths, and an amazingly-sized bonus room with private balcony. The award-winning and talented team of professionals at Allegra Homes has thoughtfully and expertly created a residence offering a secure, exclusive lifestyle in one of Sarasota's most sought-after and high-value areas. The construction quality is of the highest standard, ensuring that the home is both beautiful and built to last. Just minutes to the mainland, downtown’s cultural mecca, world-class dining and shopping venues, gorgeous area beaches and a top-ranked school system coveted by families for generations, the prized waterfront location couldn’t be better. Showcasing extraordinary craftsmanship throughout, this never-lived-in showplace is the ultimate vision for those who value the very best of coastal Florida living. There’s still time to make your own personal choices for creating the perfect custom home tailored to your family’s taste and style.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1260 DOLPHIN BAY WAY #404, SARASOTA, FL 34242
$1,395,000136 Days on yellowkey MLS ID: A4673762
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1997 Tax: $12,793 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,793
Tax Year: 2025
Remarks: ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a single family home with charm and character. The kitchen was custom built by Yoder Construction, a well-known local company, highly respected for their craftsmanship. Living room and dining area are bright and spacious. The large primary bedroom has a walk-in closet and ensuite with shower and separate soaking tub. There are two other ensuite bedrooms. All three bedrooms have California Closet systems. All windows have custom plantation shutters, adding to the charm and comfort of this amazing condo. You will want to spend your day on the light filled lanai, perfect for entertaining or simply relaxing. Dolphin Bay is a highly desirable, gated, pet friendly, 50-unit complex with a fun filled community atmosphere with three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier and kayak access. Dolphin Bay is well maintained with a freshly updated exterior and new elevators in 2024 and beautifully landscaped grounds. Just a short walk to the world famous, white crystal sands of Siesta Key beach.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
6480 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,100,000182 Days on yellowkey MLS ID: C7516381
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1979 Tax: $9,359 (2025)Community: Siesta BreakersCondo
Taxes:$9,359
Remarks: Fabulous Siesta Beach Condo at the Siesta Breakers #403 — Where Paradise Meets Profit Some properties are nice. This one is life-changing. Welcome to Unit #403 at Siesta Breakers — a rare, true beachfront end-unit perched directly on Crescent Beach, one of the most celebrated stretches of coastline on the planet. This isn't just a condo. It's a front-row seat to the Gulf of Mexico, every single day. Siesta Key's world-famous quartz-crystal sand stays cool even in the Florida heat — and 340 linear feet of it belongs exclusively to you and your guests. Across 5.6 lush acres, this gated community delivers a resort lifestyle that most only dream about. Inside, everything is already perfect. Bright. Open. Elevated. The open-concept living space flows effortlessly from designer interiors to a private balcony where sweeping Gulf views and legendary Siesta Key sunsets steal the show — every evening, without fail. The primary suite is a true sanctuary: a generous walk-in closet, an updated bath, and serene water views to wake up to. The guest bedroom is smartly designed for comfort, making it ideal for family or high-paying renters alike. It's offered completely turnkey — furniture, décor, and everything in between. Walk in and start living. Or start earning. Speaking of earning, the numbers speak for themselves. Unit #403 consistently generates $85,000+ annually in rental income, is already booked weekly through July 2026, and plugs directly into Siesta Breakers' highly sought-after weekly rental program. This isn't speculative income potential — the bookings are already in place. The community matches the lifestyle. Heated resort-style pool with tropical landscaping, Lighted tennis & pickleball courts, Private clubhouse, Security Gated Entrance, Secure under-building parking, Steps to island dining, boutique shopping & the free Siesta Key Breeze Trolley. Why #403 is the one: ? Prime beachfront end-unit — panoramic Gulf, pool & sunset views ? 340 ft. of private beach on world-renowned Crescent Beach ? Turnkey furnished & rental-ready from day one ? $85,000+ proven annual rental income ? Bookings already in place through July 2026 ? Low-maintenance luxury in a treasured, gated community Whether you're seeking your forever escape, a luxury vacation retreat, or a high-performing investment — this is the rare opportunity where all three align perfectly. Siesta Breakers #403 isn't just a purchase. It's a decision you'll never regret. Showings are only available on Saturdays between 2pm-4pm. Property is rented weekly thru July 2026.
Listing is courtesy of: CHARLOTTE COUNTY PROPERTIES (941-655-8804)
Listing Agent: Leo Albanes (941-626-9000)
4708 OCEAN BLVD #E7, SARASOTA, FL 34242
$2,350,000206 Days on yellowkey MLS ID: A4665893
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2277 Built: 1981 Tax: $16,841 (2025)Community: Windward PassageCondo
Taxes:$16,841
Remarks: 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)
5780 MIDNIGHT PASS RD #210, SARASOTA, FL 34242
$999,000136 Days on yellowkey MLS ID: A4673708
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1361 Built: 1979 Tax: $9,269 (2025)Community: Gulf & Bay Club Ph 2Condo
Taxes:$9,269
High School: Riverview High
Remarks: BEST VALUE AT SIESTA KEY BEACH GULF & BAY CLUB. Imagine living in Paradise…Welcome to your dream home on Siesta Key, where every day feels like a vacation. This beautiful beachfront corner unit in the prestigious GULF & BAY CLUB is located on the #1 Beach in America per Trip Advisor. Step into this stunning two-bedroom, two-bathroom unit, filled with natural light from expansive windows. Enjoy breathtaking sunrise and sunset views as part of your daily routine. The renovated interior features high ceilings, a gourmet kitchen with an office, modern bathrooms, smart storages and elegant details. Gulf & Bay Club is the gated resort community on the key. The serene property spans on 32 acres with 800 feet of private quartz sand beach, offering exceptional living. Beyond your home, Gulf & Bay Club offers world-class amenities, including scenic pathways to a freshwater lake with a rustic footbridge, a lush tropical courtyard with 3 heated pools, 6 pickleball courts, 4 tennis courts, 2 clubhouses and barbecue grills for social gatherings. Fitness enthusiasts can access a commercial gym, sauna, and media facility, while EV charging stations promote eco-friendliness. With an on-site rental management for one-month minimum rentals, this property is perfect for luxurious living and smart investment. Make this waterfront oasis your home where warm hospitality and serenity await.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Melanie Albaric (941-233-0957)
843 NORSOTA WAY, SARASOTA, FL 34242
$5,499,000108 Days on yellowkey MLS ID: A4676472
0 Days Off yellowkey (back on 2/11/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2467 Built: 1963 Tax: $51,752 (2025)Community: Bay IslandSpa: NoSingle Family
Taxes:$51,752
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Set along one of Siesta Key’s most coveted bayfront streets, this exceptional property offers some of the most breathtaking views in all of Sarasota—spanning open water, the city skyline, and endlessly changing sunsets. Positioned in an enclave of multi-million-dollar homes, the location alone is extraordinary, with deep, open boating water and immediate access to Sarasota Bay. While the true value lies in the irreplaceable bayfront land, the home itself has been recently remodeled and exudes a charming Siesta Key cottage vibe—warm, inviting, and perfectly suited for relaxed coastal living. Thoughtful updates blend seamlessly with the home’s character, creating a space that feels both comfortable and refined. Outdoors, enjoy a private pool overlooking the water, ideal for entertaining or unwinding after a day on the bay. A two-car garage provides convenience and storage, while the property’s proximity to world-famous Siesta Beach, downtown Sarasota, and Sarasota Memorial Hospital offers unmatched lifestyle appeal. Whether envisioned as a serene waterfront retreat, a rental investment, or the future site of a custom estate, this bayfront opportunity combines remarkable views, premier boating, and one of the finest locations on Siesta Key.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Tom Cail, Pa (941-780-2245)
276 ISLAND CIR, SARASOTA, FL 34242
$3,100,000195 Days on yellowkey MLS ID: A4667090
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2292 Built: 2026 Tax: $13,048 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$13,048
Remarks: Under Construction. Update as of 4/15/26: The home is nearly completed! Landscaping will be completed by 4/16. Inside, the final painting has taken place. There are a few odds and ends left that are almost finished! Call today to arrange your private showing! Photos are of a previous model, finishings vary. Located less than a half mile from the world-famous Siesta Key Beach, this brand-new coastal retreat is nestled on Palm Island, one of the Key’s most coveted waterfront enclaves. Sophisticated yet welcoming, this four bedroom, three bathroom home is thoughtfully designed and set on an oversized lot with a brand new 107-foot seawall. Built by Clark Horne Construction, this home showcases exceptional craftsmanship, quality materials, and thoughtful design throughout. Step through double doors into a sunlit open floor plan where every detail has been curated for modern coastal living. The gourmet kitchen is as functional as it is beautiful, featuring a Wolf range with custom hood, paneled Sub-Zero refrigerator, Bosch paneled dishwasher, Sharp microwave drawer, and a wine cooler showcased within a stunning glass-door pantry. Elegant statement lighting highlights waterfall quartz countertops, creating the perfect ambiance for quiet evenings or vibrant gatherings. The primary suite is a true sanctuary, offering volume ceilings, a spa-inspired bath, two spacious walk-in closets, and sliding glass doors that open directly onto the resort-style pool deck. Designed for seamless indoor-outdoor living, the oversized lot provides room to roam and enjoy waterfront activities—from kayaking and paddle boarding to simply soaking in the serene setting. Here, a sparkling pool and flush spa overlook tranquil canal views, completing this tropical paradise of comfort and relaxation. The expansive covered patio and entertainment-ready pool deck make every day feel like a getaway. Situated just moments from the quartz-white sands of Siesta Key Beach and the vibrant Siesta Key Village, you'll enjoy easy access to dining, boutique shopping, and live entertainment. On Palm Island, every day is a retreat—boat from your backyard, walk to the beach at sunset, and return to your own slice of tropical paradise. Call today to schedule your private showing!
Listing is courtesy of: CELLA'S REAL ESTATE INC (941-952-8649)
Listing Agent: Michael Cella (941-952-8649)
1400 COVE II PL #631, SARASOTA, FL 34242
$660,00067 Days on yellowkey MLS ID: A4681753
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 860 Built: 1979 Tax: $5,509 (2025)Community: Midnight Cove IiCondo
Taxes:$5,509
Remarks: Welcome to the most adorable condo on world famous SIESTA KEY. Start enjoying the island lifestyle in this TURNKEY condo with great water and pool views! Very comfortable open floor plan with balcony to sip your cocktails and relax. The PRIVATE DEEDED BEACH ACCESS to the quartz sand Siesta beach in priceless. Midnight Cove offers tennis, pickleball, barbecue areas, fitness, pool, on site management, boat docks and more. Very importantly, there was no storm damage. Take the free trolley to Siesta Village or walk to the south village restaurants and shops. An excellent opportunity for your vacation getaway or investment property.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Livya Hament (941-735-1227)
6157 MIDNIGHT PASS RD #E63, SARASOTA, FL 34242
$420,000239 Days on yellowkey MLS ID: A4662792
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1101 Built: 1974 Tax: $5,101 (2024)Community: Bay OaksCondo
Taxes:$5,101
Remarks: Secure This Siesta Key Condo Before it's gone! Priced to sell and ready to rent! Don’t wait - own a turnkey 2-bedroom, 2-bath condo in the highly desirable Bay Oaks community. Just minutes from the world-famous white sands of Siesta Key Beach. With weekly rentals allowed, this condo is perfect for a vacation getaway, short-term rentals, your personal island retreat, or full-time Florida living. Fully furnished and move-in ready. Enjoy poolside views from your screened porch, low HOA fees, and resort-style amenities including a heated pool, tennis courts, waterfront BBQ area, community room with pool table, and a fishing dock set in a lush, park-like setting along the bay. Centrally located on Siesta Key, you’re minutes from North and South Village shops, restaurants, and the free island trolley. Seller says bring offers. Act now - Make this Siesta Key condo your island paradise this spring!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Greg Hudson (941-302-1485)
523 REID ST, SARASOTA, FL 34242
$749,00073 Days on yellowkey MLS ID: A4681042
2 Days Off yellowkey (back on 4/15/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2249 Built: 1967 Tax: $3,377 (2025)Community: Ocean Beach RepSingle Family
Taxes:$3,377
Remarks: Under contract-accepting backup offers. Bring your vision to this Siesta Key property located directly across from The Out-of-Door Academy! The home experienced hurricane flooding, with drywall removed approximately four feet up in much of the interior and flooring removed in several areas. Property is being sold as-is. With abundant natural light, vaulted ceilings, and an existing layout ready for redesign, this home offers a blank canvas for renovation. The private lot features mature trees, deck space, and a peaceful setting in a highly sought-after location close to Siesta Key beaches and everyday conveniences. An excellent opportunity for buyers seeking to renovate in a premier school district and established neighborhood.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
208 HOURGLASS WAY #V11, SARASOTA, FL 34242
$475,00016 Days on yellowkey MLS ID: A4688135
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1432 Built: 1968Monthly Fee: $1,793 Tax: $3,258 (2025)Community: Whispering SandsVilla
Taxes:$3,258
Remarks: Under contract-accepting backup offers. 3 bedroom/2 bath freestanding villa with fenced patio. Remediation from 2024 hurricane damage completed. Property has yet to be rebuilt.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
1350 N PORTOFINO DR #107, SARASOTA, FL 34242
$374,900237 Days on yellowkey MLS ID: A4662545
Bed: 1 Bath: 2.0 Liv Area Sq Ft: 780 Built: 1969 Tax: $2,300 (2024)Community: Siesta Harbor IiSpa: NoCondo
Taxes:$2,300
Remarks: SIESTA HARBOR...55+...BEAUTIFUL CANAL & Intercoastal Water Way VISTAS with boats slowly IDILYING By and YOU HAVE BEACH ACCESS. BRING YOUR BOAT up to 30' because it only costs $1,000 ANNUALLY to berth your boat at your home! BUT WAIT till you see this TOTALLY RENOVATED BEAUTIFUL 1 bedroom 2 full bathroom condo! NEW, NEW, NEW...everything is new...Ceramic tile flooring, baseboards, interior doors & hardware, impact windows throughout, Popcorn removed and new texture ceilings, New electric plugs and switches, new kitchen with floating cabinetry, Quartz counters, new appliances, High end and modern lighting fixtures throughout, updated bathrooms also with floating vanities, incandescent lighting mirrors, new shower, New hot water tank, HVAC is only 2 years old, etc. You have plenty of storage as the bedroom has 2 closets (one is walk in), linen closet, Hall coat closet, pantry closet AND just outside your front door is a storage room for your bikes etc.! Amenities include a beautiful pool overlooking the water, shuffleboard, rec center, pier for boat watching and gatherings, tandem boat docks, fitness center FREE laundry on 2nd, 3rd and 4th floors PLUS FOB access to the beach across the street @ Crescent Arms. ALSO you have one DESIGNATED covered carport parking spot with plenty of guest parking #537. Outdoor grilling SPOT. Rental friendly but no pets except authentic guide dogs. PRICED BELOW MARKET AT $374,900 Please consider a pre-approval from Buddy Moore / Owner of Moore Mortgage here in Sarasota...Buddy will pay for your appraisal (a $650 value) AND get you a GREAT RATE!
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Scotty Ledford (941-400-7360)
5103 WINDWARD AVE, SARASOTA, FL 34242
$3,657,625104 Days on yellowkey MLS ID: A4676707
Bed: 3 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3034 Built: 2026 Tax: $4,091 (2024)Community: Sara SandsSpa: YesSingle Family
Taxes:$4,091
Remarks: Completed new construction! Built safely and securely ten feet above the island’s flood plain, 5103 Windward is unparalleled new construction with saltwater boating access to the Intracoastal Waterway and Gulf beyond. Along the water’s edge, this homesite spans nearly 1/3 acre on the Grand Canal with 90 ft. of new seawall. The central Siesta Key location makes getting to the spectacular white sand beaches and charming Siesta Village easy and convenient. The free-flowing plan, offering 3,034 sq. ft. of open living, will seduce you with its inviting atmosphere wrapped in casual elegance and modern sophistication. With plenty of natural light, the great room boasts double-height ceilings adorned with rich architectural detail, an elaborate floor-to-ceiling fireplace wall, and see-through views to the expansive outdoor space and coveted canal setting. Beyond the great room’s glass doors, an entertaining lounge with wood ceiling accents, a professional grill station, and a heated pool/spa await your plans for spending cherished time with family and friends. As evening approaches, night lighting transforms the beautiful backyard and creates a timeless ambiance that encourages relaxation and reflection. A gorgeous kitchen is enhanced with an abundance of amenities including a premium Sub-Zero and Wolf appliance package, stone counters, stylized fixtures and finishes, a walk-in pantry, and adjoining laundry. The formal dining room features a built-in buffet and French doors leading to a brick paver patio, making it a wonderful spot for dining alfresco under the stars. The bonus room, with wet bar and pool bath, features two walls of glass sliders showcasing the extensive outdoors and picturesque water views. The primary suite is an oasis of serenity with an office outfitted with built-ins, a generous wardrobe for two, and an exquisite bath intended to pamper and spoil with a free-standing tub, a frameless glass shower with rain head, separate vanities with stone tops, and a water closet. Two additional en-suites offer plenty of room to unwind and rejuvenate in comfortable privacy. A brick paver drive, a 3-car garage, professional landscaping with timed irrigation, eye-catching curb appeal, and other notable customizations inside and out, complete this magnificent waterfront home. This fresh new residence, designed by the award-winning team at Allegra Homes, has been artfully designed and crafted to offer the highest quality to those who live here. An exciting opportunity to make this island paradise yours!
546 FREELING DR, SARASOTA, FL 34242
$12,500,0003 Days on yellowkey MLS ID: A4687147
Bed: 5 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 4353 Built: 2027 Tax: $17,536 (2025)Community: Bay IslandSpa: YesSingle Family
Taxes:$17,536
Remarks: Pre-Construction. To be built. Discover an extraordinary opportunity to own an expansive double lot of 0.52 acres on North Siesta Key with this single-story, new construction transitional modern-style luxury home by Pham Development. Offering 170 feet of deep-water canal frontage, the residence features 4,353 square feet under air and 15,453 square feet under roof. With 5 bedrooms, 5 full bathrooms, 2 half baths, and a designated private office, the home showcases soaring 17.5-foot vaulted ceilings and a striking glass wine wall, complemented by designer finishes that fill the interiors with natural light and tranquil water views. Across the canal, lush landscaping provides a serene and private backdrop, with flexibility to customize finishes and style. Designed for both comfort and entertaining, the open-concept living spaces flow seamlessly to a resort-style outdoor retreat. The expansive back patio is equipped with remote-controlled electric mosquito screens, allowing you to enclose the space at the touch of a button for year-round enjoyment. Enjoy a spectacular pool with a champagne hot tub spa, a generous patio, and a fully equipped outdoor kitchen perfect for alfresco dining. A scenic path leads to your private dock with a state-of-the-art electric system and space for a boat up to 37 feet, offering smooth access to the bay and Gulf. The primary suite is a private sanctuary with spa-inspired amenities and dedicated quarters. A chef’s kitchen anchors the heart of the home with premium appliances and refined finishes. An elegant circular driveway creates a grand entrance, while the expansive ground level offers room for up to 10 cars, complemented by an impressive 10-car garage—ideal for collectors or additional storage. This exceptional waterfront residence delivers effortless luxury and refined coastal living.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
4634 HIGEL AVE, SARASOTA, FL 34242
$7,500,0003 Days on yellowkey MLS ID: A4689982
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3875 Built: 2024 Tax: $36,904 (2025)Community: Ocean Beach RepSpa: YesSingle Family
Taxes:$36,904
Remarks: Start living your dream lifestyle on world-famous Siesta Key in this Pham Development custom-built waterfront British West Indies–style home. Located on a quiet street on the north end of the key—close to the beach, Siesta Key Village and Out-of-Door Academy—and just minutes on and off the island, this residence offers island living at its best. Set on a corner canal-front lot, the two-story home features 5 bedrooms, 5 full bathrooms and 1 half bath, with 3,875 square feet under air, a great room floor plan, soaring 22-foot vaulted ceilings, and walls of windows and doors—including large pocket sliders—that bring in abundant natural light and seamlessly connect indoor and outdoor living.
105 ISLAND CIR, SARASOTA, FL 34242
$2,680,950365 Days on yellowkey MLS ID: A4647817
0 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2750 Built: 1953 Tax: $7,593 (2024)Community: Palm IslandSpa: YesSingle Family
Taxes:$7,593
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Pre-Construction. To be built. IMAGINE a Custom Coastal Contemporary Home on Palm Island, Siesta Key. Picture a thoughtfully designed residence offering 2,750 sf of indoor living space and 3,467 sf of total indoor/outdoor space. E/M Custom Homes is renowned for their impeccable craftsmanship and modern coastal design creating a one-of-a-kind residence to be tailored to your lifestyle. This stunning 4-bedroom, 3.5-bath home includes an open Concept Floor Plan, Gourmet Kitchen with custom cabinetry, luxury appliances, and a walk-in pantry—ideal for entertaining. Enjoy a First-Floor Master Suite with a spa-inspired en suite bath and a large walk-in closet. The Second Floor boasts 3 bedrooms, a second gathering room, an office, a laundry room, and a Balcony to relax and enjoy island breezes and views. Be inspired to grill in your Outdoor Kitchen on the expansive covered lanai, perfect for alfresco dining. Lounge in your Custom Designed Private Pool, appreciating outdoor living. You also have an Oversized 2-Car Garage with easy access to the downstairs Laundry/Mudroom entry. Set on 2 lots, totaling 0.45 acres (19,456 sf), this property offers a rare combination of space and luxury. Just a 2 block stroll to sink your toes into the luxurious quartz sand and sparkling water of our award-winning Siesta Key Beach. The Village is minutes away where you will find fabulous restaurants, live music, specialty shops, night life, Sunday Farmers Market, art festivals and more. Your dream coastal lifestyle awaits!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Linda Scheller, Llc (941-806-7981)
1275 SIESTA BAYSIDE DR #1275, SARASOTA, FL 34242
$999,00038 Days on yellowkey MLS ID: A4684885
1 Days Off yellowkey (back on 4/14/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1645 Built: 1988 Tax: $9,421 (2024)Community: Gulf & Bay Club BaysideCondo
Taxes:$9,421
Remarks: An amazing year-round residence, vacation or investment property! Don't miss this rare opportunity to own a beautifully furnished 3-bedroom, 2-bath + loft unit just steps from world-renowned Siesta Beach with dedicated beach access. Recently renovated, this turnkey residence features a bright open floor plan with wood-look tile, shiplap accents, and raised ceilings in the hallways, kitchen and dining areas, a rare update in the community. The kitchen boasts full height solid wood cabinetry, quartz countertops, stainless appliances, and a charming, windowed breakfast nook. Enjoy multiple dining options including a formal area, bar, and a glass-enclosed lanai, perfect for entertaining. The spacious primary suite opens to a Florida room with tongue and groove wood ceiling overlooking a serene pond and wildlife, with a renovated ensuite featuring dual sinks, walk-in shower, abundant storage, and a large closet. Upstairs includes a versatile loft, two guest bedrooms, and a full bath. Relax on the inviting front porch with views of Siesta’s iconic sunrises and sunsets. Additional perks include a one-car garage, private driveway, and in-unit laundry. Unit has all brand new screens. Located in Gulf & Bay Club Bayside, a gated community with resort-style amenities: two pools, tennis/pickleball courts, clubhouse, fitness center, sauna, fishing pier, walking paths, and BBQ areas. On-site management and a one-week rental minimum make this a standout investment property with income potential of $80k plus. Spend your days enjoying effortless beach access for sunrise coffee, long shoreline walks, and unforgettable Gulf sunsets. When it’s time to explore, Siesta Key Village is just minutes away with favorite restaurants, local shops, and live music—an unbeatable setting to experience Siesta Key at its finest.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Robert Ruiz (941-544-3299)
4508 WOODSIDE RD, SARASOTA, FL 34242
$2,450,000128 Days on yellowkey MLS ID: A4674684
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2276 Built: 1969 Tax: $7,045 (2025)Community: Siestas Bayside Waterside WoodSpa: YesSingle Family
Taxes:$7,045
Remarks: Luxury Waterfront Living Now Priced to Move Welcome to 4508 Woodside Rd, a true boater’s paradise on Siesta Key offering privacy, deep-water access, and refined coastal living. Positioned on one of the island’s deepest canals, this property provides quick access to the Intracoastal and Sarasota Bay, with 95 feet of waterfront and a 75-foot dock designed for serious boating. Inside, the home features a fully renovated interior with designer tile flooring, an open-concept layout, and expansive sliding glass doors that seamlessly connect indoor and outdoor living. The chef’s kitchen is equipped with custom cabinetry, a Viking hood system, gas cooktop, and premium appliances, while a temperature-controlled wine cellar adds a true luxury touch. The primary suite is a private retreat with a spacious layout, oversized walk-in closet, and a spa-style bathroom featuring a glass-enclosed shower and outdoor shower access. Every detail has been thoughtfully designed for comfort and functionality. Step outside to your own private resort complete with a saltwater pool and spa, lush landscaping, integrated lighting, and a covered pergola with outdoor lounge space, propane fire pit, and TV viewing area. A retractable awning and outdoor wet bar enhance the space, making it ideal for entertaining year-round. Additional highlights include a 250-gallon propane tank, 14.5 KW generator, updated HVAC, newer water heater with circulating system, epoxy-finished garage, and hurricane protection features. Originally introduced at $2,690,000, the property has undergone multiple strategic price adjustments and is now positioned to sell, presenting one of the best waterfront opportunities on Siesta Key. With nearby properties trading at significant premiums for land value alone, this offering delivers exceptional value for both end-users and investors. Also available: luxury yacht (inquire for details).
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
1345 MOONMIST DR #T6, SARASOTA, FL 34242
$620,000204 Days on yellowkey MLS ID: A4654050
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1575 Built: 1968 Tax: $3,545 (2024)Community: Polynesian GardensVilla
Taxes:$3,545
Remarks: Welcome to your dream villa! This spacious coastal villa retreat on Siesta Key boasts 2-bedrooms and 2-bathrooms and offers 1,575 square feet of comfortable, open-concept living space, perfect for both relaxing and entertaining. Step inside to a freshly painted interior featuring a modern, neutral palette that complements any décor. This wonderful detached-villa is in a serene location just across the street from million-dollar residences on the Bay and offers low-maintenance living with a luxurious feel. It is high and dry and has never flooded. This villa has an impressive list of updates including a new Barrel Tile Roof and complete Air Conditioning System. The large open dinning/living room area has bamboo flooring and sliding glass doors leading to your retractable awning-covered paved patio. A separate office area with built in desk and shelving and the potential for adding a sleeper sofa. A spacious primary bedroom with en-suite bathroom has a walk in closet and separate storage area. The second bedroom is roomy, light and pleasant ideal for either family or guests. The kitchen was completely remolded in 2016 and has a built in pantry, shaker cabinets with pullout shelving and a breakfast nook. Don’t miss this move-in ready gem with big-ticket upgrades already done! Polynesian Gardens is ideally located and provides a tranquil and unique Siesta Key escape for owners and guests alike. Relax and enjoy the tropical palms, large heated pool and peaceful intracoastal pier that provide a relaxing Siesta Key experience. Either take a short walk or take the free trolley which stops directly in the front of the community to world famous Siesta Key Beach, local restaurants, shopping, boat and fishing charters and rentals for all outdoor and water activities. Additional Features: •New Barrel Tile Roof. •This home features a spacious carport, offering sheltered parking and added storage potential. •Laundry room with full-size washer & dryer. •Quiet, well-maintained community. •Community amenities included; landscaping, exterior maintenance, cable tv, water, intracoastal pier and large heated pool. *The Polynesian Gardens Home Owners Association has plans in effect to paint the exterior of this Villa at no cost to the owner. Potentially the new owner will have their choice of colors. The unit is VACANT!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Dean Hall (941-726-7197)
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