Location: Sarasota , 34242
Do Not Show Listings
732 SIESTA DR, SARASOTA, FL 34242
$2,995,000480 Days on yellowkey MLS ID: A4640849
Bed: 3 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3743 Built: 1956 Tax: $13,183 (2024)Community: Bay Island ShoresSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$13,183
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Rare and extraordinary waterfront offering on the coveted North end of Siesta Key, this premier Bay Island estate parcel presents the ultimate canvas for creating a world-class coastal retreat. Set on nearly half an acre, the property commands sweeping waterway views and offers 90 feet of protected sailboat-water frontage, complete with an existing 73-foot composite and tile dock—an exceptional amenity for the discerning boating enthusiast. To seamlessly bring your vision to life, fully customizable luxury home plans, as well as projected expenditure framework are available for review from Salt Wave Construction thus significantly expediting the design-build process. The seller has also committed to demolition of the existing structure, allowing for a smooth and efficient transition to new construction. The proposed residence spans approximately 6,366 square feet, including over 4,000 square feet of refined, air-conditioned living space, thoughtfully designed to maximize waterfront exposure and elevate indoor-outdoor living. Multiple entertaining spaces, expansive terraces, and view-oriented decks create the perfect setting for both grand gatherings and intimate moments, all framed by captivating water vistas. Ideally located for effortless access on and off Siesta Key and just minutes from the culture, dining, and sophistication of Downtown Sarasota, this exceptional property offers the rare combination of privacy, prestige, and proximity. An unparalleled opportunity to craft a legacy waterfront estate in one of Sarasota’s most sought-after enclaves.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jay Mitchell Jr., Pllc (941-586-1754)
5108 SANDY SHORE AVE, SARASOTA, FL 34242
$1,050,00033 Days on yellowkey MLS ID: A4694309
1 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1681 Built: 1960 Tax: $4,305 (2025)Community: Sara SandsSpa: NoSingle Family
Taxes:$4,305
Tax Year: 2025
Middle School: Sarasota Middle
Remarks: Capturing the essence of “location, location, location,” this canal-front pool home is ideally situated on a quiet cul-de-sac street on the desirable north end of Siesta Key. Offering 2 bedrooms & 2 bathrooms, the well-maintained, albeit dated, residence presents an exceptional opportunity to update or build the custom waterfront estate of your dreams. Set in a premier location where the true value lies in the land and lifestyle, the property has not experienced flooding and offers the rare combination of tranquility, boating access, and proximity to the beach. Just 1.1 miles away are the world-renowned white quartz sand beaches of Siesta Beach, with Beach Access #5 conveniently located at the west end of Siesta Key Village. The Village is known for its vibrant island atmosphere, featuring an eclectic mix of restaurants, boutiques, nightlife, and entertainment. For boating enthusiasts, the home offers an 18 minute +/- boat ride via the Grand Canal to Sarasota Bay, with direct access to Big Pass and the Gulf of Mexico. Whether you envision relaxing poolside, spending carefree days at the beach, enjoying boating adventures, or embracing the vibrant island lifestyle, this property offers endless possibilities in one of Sarasota’s most coveted waterfront locations.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Angela Adams (941-809-9760)
1250 N PORTOFINO DR #202, SARASOTA, FL 34242
$469,90026 Days on yellowkey MLS ID: A4695140
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1969Monthly Fee: $958 Tax: $4,389 (2025)Community: Siesta Harbor IiCondo
Taxes:$4,389
Elementary School: None
High School: None
Middle School: None
Remarks: This second floor 2-bedroom, 2 bath condo is located in the Marlin House in the 55+ community of wonderful Siesta Harbor! This unit offers an open floor plan with plenty of light. Step out onto one of the balcony’s to view the peaceful water, boats going by and you may see dolphins playing while you are enjoying your morning beverage. This community offers more than just serene water views. Included in the many amenities are a heated pool, shuffleboard, library and a fitness area. Feel free to participate in movie night, Tai Chi and Happy Hour along with many other activities offered at the clubhouse. Are you a boater? Siesta Harbor is one of the few condos on Siesta Key that offers a boat dock with deep water, for those interested in this bonus extra. If you wish to walk to the beautiful Siesta Key beach, voted best beach in the USA and the world, private access right across the street through a deeded access. Siesta Harbor keeps its grounds and buildings well maintained, recently updated with new roofs and updated common areas. This unit is a must have, with the deep water of the Intracoastal Waterway right in your backyard, the peaceful and serene atmosphere of the area, the beautiful beach just a shore walk away and it can be an income producer should that be something you want to consider.
Listing is courtesy of: BECKMANN REAL ESTATE (941-346-3500)
Listing Agent: Josh Beckmann (941-321-3500)
5179 HIDDEN HARBOR RD, SARASOTA, FL 34242
$7,950,000247 Days on yellowkey MLS ID: A4669099
INCREASED by $450,000 (6.0%) on 06/10/2026
Bed: 6 Bath: 7.5 Gar: 3 Liv Area Sq Ft: 4900 Built: 2026 Tax: $9,659 (2024)Community: Hidden HarborSpa: YesSingle Family
Taxes:$9,659
Remarks: Pre-Construction. To be built. Welcome to this newly imagined Siesta Key residence, a world curated for those with a sophisticated palate for modern architecture at the edge of the sea. Here, light dances across water and peers through your windows blending luxury, privacy and resort-style living within the exclusive enclave of Hidden Harbor. The journey begins as you approach this designer estate—a vision of coastal modernism, 4,900 square feet under air and meticulously crafted by TDI Coastal Homes, celebrated for precision, integrity, and elegance. Clean lines and natural textures blend with lush tropical surroundings, setting the stage for a life that lives like an endless retreat. The lower level invites you to linger outdoors surrounded by the scent of the saltwater breeze and the sounds of the cascading waters of the 65-foot infinity pool and spa. A covered living space blurs the line between home and horizon. A custom waterslide arcs playfully into the pool, while beyond, your private dock with a 20,000-pound lift awaits spontaneous voyages to Roberts Bay. Ascend by elevator or sculpted staircase to the heart of the home—spaces that feel both expansive and intimate. Walls of glass reveal shimmering water views, while the Meile appliance suite anchors a chef’s kitchen made for creating fine cuisine and lasting memories. Every detail and finish bears the signature of master craftsmanship. The home’s six bedrooms include two primary suites, each a retreat of its own with spa-inspired baths. Six full and three half baths offer both comfort and convenience for family and guests alike. A 700-square-foot bonus space stands ready to become whatever your imagination allows—a golf simulator, game lounge, or wellness studio. A three-car garage, new seawall, whole-home generator, and zero water intrusion during the 2024 storms provide unmatched peace of mind. As evening settles, the home transforms. Ambient lighting glows across the infinity edge and the hush of the bay replaces the day’s energy. You can almost hear the future stories unfolding here—laughter by the pool, sunrise swims, quiet coffee on the terrace. 5179 Hidden Harbor Road isn’t just a home; it’s a state of being—modern, effortless, and deeply connected to the water.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
5155 HIDDEN HARBOR RD, SARASOTA, FL 34242
$1,995,000152 Days on yellowkey MLS ID: G5107159
2 Days Off yellowkey (back on 6/10/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2233 Built: 1973Monthly Fee: $332 Tax: $7,806 (2025)Community: Hidden HarborSpa: NoSingle Family
Taxes:$7,806
Remarks: Nearly 200 feet of deep-water frontage in the prestigious Hidden Harbor enclave of Siesta Key—no bridges, quick access to Roberts Bay and the Gulf of America. Move-in ready and never flooded. Enjoy island living in this private waterfront setting surrounded by multi-million dollar estates. Lush, canopy-lined brick paver streets, wide water views, no through streets, and excellent boating access. The home has been thoughtfully renovated with an emphasis on functionality and storage, featuring an updated kitchen, modernized bathrooms, tile flooring throughout, recessed lighting, impact-rated windows and sliders, landscape lighting, a dedicated well with irrigation system, and a heated saltwater pool. Bike to the award-winning Siesta Key Beach, dine and shop in Siesta Village, kayak from your dock to nearby mangrove tunnels, or enjoy the convenience of downtown Sarasota less than seven miles away. A rare waterfront home offering immediate enjoyment and long-term upside in a neighborhood experiencing significant luxury redevelopment.
Listing is courtesy of: LIST NOW REALTY, LLC (352-385-7636)
Listing Agent: Matt Buttner (352-385-7636)
5661 MIDNIGHT PASS RD #401, SARASOTA, FL 34242
$463,000153 Days on yellowkey MLS ID: A4678954
REDUCED by $6,900 (1.5%) on 06/10/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1012 Built: 1975 Tax: $4,629 (2025)Community: White Sands VillageCondo
Taxes:$4,629
Remarks: Welcome to coastal living at its best in White Sands Village, a desirable waterfront community ideally located in the middle of Siesta Key and 1 mile from The Village. This charming 2-bedroom, 2-bath end-unit condominium (no flood damage), offering added peace of mind and ease of ownership. The community is surrounded by lush tropical landscaping and features a clubhouse and sparkling community pool, creating a relaxed island atmosphere. White Sands Village offers water access with Gulf-front amenities and boat slips available via waitlist, perfect for boating enthusiasts. This property may be used as a rental or income-producing investment with a minimum 2-week rental period, making it an excellent option for seasonal use or short-term rental opportunities. Ideally located across the street from world-famous Siesta Key Beach, along with nearby restaurants, shopping, and entertainment, plus convenient on-and-off island access. Whether you’re looking for a full-time residence, vacation retreat, or rental investment, this property delivers the best of the Siesta Key lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lisa Blakeney (616-795-6545)
7108 MIDNIGHT PASS RD, SARASOTA, FL 34242
$4,219,000110 Days on yellowkey MLS ID: A4685107
Bed: 7 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4697 Built: 1970Monthly Fee: $467 Tax: $10,150 (2025)Community: Siesta Properties IncSpa: NoSingle Family
Taxes:$10,150
High School: Riverview High
Remarks: A rare opportunity situated on an expansive 1.8 acres, this estate is located behind the gates of one of Siesta Key’s most exceptional estate settings. Surrounded by lush tropical foliage and serene lagoon-style water features, the property offers remarkable privacy and versatility with a 5-bedroom, 4-bath main residence and a separate 2-bedroom, 1-bath guest house—ideal for multi-generational living, hosting guests, or providing dedicated staff accommodations. The grounds evoke a secluded, natural sanctuary while remaining just minutes from Siesta Key’s vibrant dining, boutique shopping, and world-renowned coastline. Positioned within the prestigious Sanderling Club, the estate grants access to one of Sarasota’s most storied and sought-after communities. Celebrated for its historic bay-to-gulf setting and architectural significance, the Sanderling Club offers residents private beach access, 24-hour gated security, tennis and pickleball courts, a beach front clubhouse, and a members-only marina just steps from the property—delivering a refined coastal lifestyle unlike anywhere else. Located moments from the iconic, powder-soft sands of Siesta Beach, this property presents a rare chance to create a legacy residence in an extraordinary setting. Whether you choose to enhance the existing homes or envision an entirely new custom masterpiece, the possibilities are limitless. Properties of this scale within the Sanderling Club are exceptionally scarce, making this offering truly remarkable.
Listing Agent: Maryana Zilinskiy (941-744-6065)
8250 SANDERLING RD, SARASOTA, FL 34242
$18,900,000320 Days on yellowkey MLS ID: A4660281
Bed: 5 Bath: 6.0 Gar: 6 Liv Area Sq Ft: 7756 Built: 2000Monthly Fee: $450 Tax: $102,460 (2024)Community: Sanderling Club / Siesta KeySpa: YesSingle Family
Taxes:$102,460
Remarks: Guy Peterson's architectural masterpiece is located in Sarasota's most prestigious gated enclave. Positioned on the white sands of Siesta Key, 8250 Sanderling Road is more than a residence; it is a bold statement in modern architecture, masterfully envisioned by renowned architect Guy Peterson, FAIA. Set on 1.54 private acres with 150 feet of Gulf-front beach and 150 feet of lagoon frontage behind the gates of the exclusive Sanderling Club, this estate is a rare fusion of design innovation, artistic expression, and coastal tranquility. Widely recognized as one of Florida’s most iconic modern beach residences, the property has received top honors including the AIA Florida Test of Time Design Award, AIA Florida Gulf Coast Honor Award and the AIA Florida Excellence in Architecture Award, and has been featured in The Wall Street Journal, HGTV’s Homes Across America, Robb Report, Florida Design, Sarasota Magazine and more. It is also prominently included in Four Florida Moderns and 50 US Architects Residential and Planning, placing it among the most significant architectural achievements in the country. The home was designed as a series of four interconnected pavilions anchored in concrete and glass. It was reimagined in 2014 by the original architect, Guy Peterson, alongside Michael K. Walker and Richard Geary. The result is a striking architectural clarity that elevates the original design while introducing refined modern comforts. The sculptural façade is defined by bold horizontal lines, artful cutouts, and a seamless blend of poured concrete, steel, and sanded glass. A shell stone path leads to a dramatic entry, where the residence begins to unfold like a gallery of light and form. Inside, the interiors echo the clean geometry of the exterior. A soaring multi-level foyer acts as a central spine of the home, where light, shadow and structure interplay like a living installation. The custom-designed bar, lit by an onyx countertop, is functional and atmospheric. The dining room is framed by concrete columns and translucent glass, revealing a cinematic view of the Gulf beyond. The kitchen, anchored by warm teak millwork, features dual islands, Miele and Wolf appliances, and honed marble surfaces, creating a space as elegant as it is functional. The owner’s suite offers a peaceful retreat with a sitting area, private terrace, and coffee bar, while dual baths evoke spa-like tranquility with stone finishes and minimalist detailing. A private office with panoramic Gulf views inspires focus, while additional guest suites offer comfort and privacy with en-suite accommodations. Outside, a sprawling terrace connects indoor and outdoor living, ideal for intimate reflection or entertaining against the sound of waves. Residents of The Sanderling Club enjoy access to a private marina and beach plus 24-hour guard-gated enclave celebrated for its discretion and architectural legacy. With its distinguished pedigree and timeless design, 8250 Sanderling Road is a coastal sanctuary that honors the past, elevates the present, and secures its place among the most architecturally significant homes in on Florida’s Gulf Coast.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
6300 MIDNIGHT PASS RD #21, SARASOTA, FL 34242
$869,000152 Days on yellowkey MLS ID: A4678951
REDUCED by $30,000 (3.3%) on 05/26/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1253 Built: 1969 Tax: $5,276 (2025)Community: Crystal Sands 1Villa
Taxes:$5,276
Remarks: Everything is brand new in this beautifully renovated, turnkey furnished two bedroom, two bath end-unit villa offering an exceptional Siesta Key beach lifestyle just steps from the Gulf. The desirable split floor plan features spacious bedrooms, generous closets, and an open-concept living area filled with natural light, enhanced by a sun-lit Florida room. The updated kitchen is thoughtfully designed with granite countertops, a coordinating backsplash, soft-close cabinetry, and new stainless steel appliances. The primary suite offers a wall-to-wall closet, transom window, and sliding glass doors opening to the Florida room. Additional highlights include luxury vinyl plank flooring, all-new furnishings, and an attached one-car garage with washer and dryer plus ample storage for beach gear. Whether enjoyed as a private coastal retreat or a lock-and-leave rental opportunity, this residence truly offers the best of both worlds. Crystal Sands is a well-managed, financially stable beachfront community that has remained highly desirable since 1969 due to consistent upkeep and thoughtful renovations. The condominium comprises a collection of one, two, and three bedroom villas along with a Gulf-front high-rise tower, all set within beautifully maintained grounds. Residents and guests enjoy private beach access with umbrellas and loungers, two heated swimming pools, a clubhouse, on-site rental management, and night security, all just moments from Siesta Key’s renowned dining and shopping.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Bev Murray (941-724-4995)
8501 MIDNIGHT PASS RD, SARASOTA, FL 34242
$29,995,00044 Days on yellowkey MLS ID: A4692839
Bed: 6 Bath: 8.5 Gar: 7 Liv Area Sq Ft: 12000 Built: 2024 Tax: $141,465 (2025)Community: Siesta KeySpa: YesSingle Family
Taxes:$141,465
Remarks: Set across nearly three acres of pristine waterfront on Siesta Key, Crystal Waters is the most significant private estate in Sarasota—a once-in-a-generation offering that redefines luxury living on Florida’s Gulf Coast. With extraordinary scale, architectural pedigree, and 217 feet of direct Sarasota Bay frontage, this landmark property represents a level of craftsmanship, beauty, and exclusivity rarely seen in the region. Designed by renowned architectural firm Stofft Cooney Architects and custom-built by Chris Jorgensen of Florida West Builders, the Palm Beach-inspired estate encompasses 10,267 square feet with five bedrooms, six full baths, and two half baths. Surrounded by lush tropical gardens and panoramic bay views, every aspect of the property has been conceived to deliver an unparalleled waterfront lifestyle. A dual-gated arrival along a Tabby seashell drive leads to a stately façade framed by towering palms and a grand porte cochère. Beyond solid mahogany doors, a magnificent foyer welcomes guests with travertine floors inlaid with cabochon stone and a sweeping staircase featuring hand-crafted Chippendale railings. Walls of impact glass dissolve the boundary between indoors and out, filling the residence with natural light and uninterrupted views of Sarasota Bay. Refined details include a natural gas fireplace with imported limestone hearth, hand-crafted Vitali European oak flooring in a warm Milano finish, custom millwork, and a serene palette of coastal hues. The kitchen is both a showpiece and gathering place, appointed with custom Campbell cabinetry, Cristallo quartzite surfaces, a custom La Cornue range, dual islands, and walk-in and butler’s pantries. A bayfront breakfast nook and formal dining room open seamlessly to expansive waterfront terraces. Nearby, the clubroom showcases hand-painted Gracie chinoiserie panels, vaulted cypress ceilings, and a wet bar. The first-floor primary suite serves as a private sanctuary overlooking the bay, with French doors opening to the pool terrace. Custom dressing rooms and spa-inspired baths surround a striking octagonal vestibule featuring New Ravenna mosaic floors, Calacatta Matarazzo quartzite, a soaking tub, and marble-clad shower. Upstairs, guest suites, a lounge, and an exercise room provide exceptional accommodations. An Old Florida-style guest residence above a four-car garage offers Pecky Cypress-lined interiors, vaulted ceilings, a full kitchen, covered balcony, and spacious bedroom suite. The main residence is further complemented by an oversized three-car garage. Outdoors, winding pathways lead through beautifully curated grounds to a spectacular 56-foot vanishing-edge saltwater pool that appears to merge with the bay beyond. A covered waterfront pavilion with fireplace, summer kitchen, and tongue-and-groove ceiling creates an elegant setting for entertaining. A private tennis court and lighted pavilion with lounge and fireplace complete the resort-caliber amenities. Along the shoreline, a 90-foot dock extends into Little Sarasota Bay and features a floating kayak launch and a 20,000-pound lift capable of accommodating a 34-foot vessel. Crystal Waters is more than a residence—it is Sarasota’s defining waterfront estate. Unmatched in scale, setting, craftsmanship, and provenance, it stands as one of the finest private properties ever created on Florida’s Gulf Coast. Available lot for sale directly across the street enjoys beach access.
Listing Agent: Kim Ogilvie (941-951-6660)
8750 MIDNIGHT PASS RD #501, SARASOTA, FL 34242
$649,000100 Days on yellowkey MLS ID: A4686287
REDUCED by $11,000 (1.7%) on 06/09/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1980 Tax: $6,787 (2025)Community: TortugaCondo
Taxes:$6,787
Remarks: Experience the relaxed elegance of Gulf-front living at Tortuga on the quiet south end of Siesta Key. This beautifully positioned northwest corner residence offers direct views of the Gulf of Mexico and Turtle Beach, where spectacular sunsets paint the sky each evening. With 1,232 square feet of living space, this 2-bedroom, 2-bath condominium is designed to capture natural light and coastal breezes from multiple exposures. Step onto your private lanai and take in panoramic water views, the soothing sound of the surf, and the tranquil atmosphere that makes the south end of Siesta Key so special. Inside, the spacious layout offers comfortable living and dining areas ideal for entertaining or simply relaxing after a day at the beach. Residents of Tortuga enjoy a private beachfront location, heated swimming pool, tennis courts, clubhouse, and convenient access to kayaking and paddleboarding along the nearby lagoon. Covered parking and additional guest parking are included. Located just minutes from Siesta Key Village, dining, and shopping, yet tucked away on the peaceful Turtle Beach side of the island, this residence offers the perfect balance of privacy, nature, and coastal lifestyle. Come discover why Tortuga is one of Siesta Key’s most treasured beachfront communities. CONDO ALL UPGRADED WITH HURRICANE WINDOWS!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Kelly Trippe (941-330-7750)
6266 MIDNIGHT PASS RD #404, SARASOTA, FL 34242
$1,170,00063 Days on yellowkey MLS ID: A4691031
REDUCED by $10,000 (0.8%) on 06/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1263 Built: 1980 Tax: $10,169 (2025)Community: Excelsior Beach To BayCondo
Taxes:$10,169
Remarks: RARELY AVAILABLE INCOME PRODUCING EXCELSIOR GULF FRONT UNIT This large unit has been completely updated and renovated with Impact windows and new HVAC in 2025, Upgraded kitchen and all appliances, plantation shutters, and Hunter Douglas window shades, in-unit washer/dryer, custom tile throughout, tastefully appointed with fine furnishings and all the accoutrements for the Siesta Beach lifestyle. The under-building covered parking and elevators are conveniently located the spacious gulf front patio is the perfect place to relax and enjoy the fabulous views. Excelsior is your Gulf to Bay resort residence with a Private White Sand Beach, Two Large Heated Swimming Pools, Poolside Restrooms / Hot Water Showers, Shuffleboard, Two Heated Whirlpools, Two Lighted Tennis Courts, Two Pickle Ball Courts, Fitness Center, Large Gulfside Sun Deck, Beach Loungers and Chairs, Lounges & Sunbathing Parapets' Outdoor Barbecues / Picnic Areas, Intercoastal Fishing Pier / Shaded Viewing Area, Community Room and monthly community events', Library' Walk to Shopping, Dining, Bike & Boat Rentals Located just a half mile to the S village shops, dining and marina makes this a great spot to enjoy all the best that world famous Siesta Key has to offer.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Bob Stahlschmidt Ii (941-266-2684)
$1,170,00023 Days on yellowkey MLS ID: A4695534
Bed: 2 Bath: 0.0 Liv Area Sq Ft: 1263 Built: 1980 Tax: $10,169 (2025)Community: Excelsior Beach To BayApartment
1280 DOLPHIN BAY WAY #503, SARASOTA, FL 34242
$1,589,00095 Days on yellowkey MLS ID: A4687031
3 Days Off yellowkey (back on 6/8/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2217 Built: 1998Monthly Fee: $1,985 Tax: $13,269 (2025)Community: Dolphin Bay-Siesta Key Sec ACondo
Taxes:$13,269
Remarks: Under contract-accepting backup offers. Experience endless panoramic views of downtown Sarasota and Sarasota Bay from the climate-controlled balcony of this newly renovated top-floor residence in the gated community of Dolphin Bay on Siesta Key. This spacious condo offers over 2,200 square feet of beautifully updated living space, featuring 2 bedrooms, 2 bathrooms, and a den, all enhanced by vaulted ceilings that create an open and airy coastal atmosphere. Enjoy stunning sunsets over Siesta Key Beach from the front entryway each evening, and wake to beautiful sunrises from the primary bedroom and lanai—an exceptional feature of this remarkable home. Residents of Dolphin Bay enjoy a true waterfront lifestyle with access to a private community dock, clubhouse, tennis courts, fitness center, and a resort-style pool. A private one-car garage, with epoxy flake floors, is conveniently located just steps from the elevator. Perfectly situated within minutes of the beach, shops, and restaurants, this residence combines luxury, convenience, and the best of Siesta Key living. Enjoy the waterfront lifestyle at its finest in this exceptional move-in-ready home. Contact me for a private showing today.
6308 MIDNIGHT PASS RD #6, SARASOTA, FL 34242
$995,000357 Days on yellowkey MLS ID: A4657483
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1232 Built: 1965Monthly Fee: $1,005 Tax: $5,582 (2025)Community: Crescent ArmsSpa: NoVilla
Taxes:$5,582
Remarks: Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Derek Edwards (941-929-3183)
5322 CALLE DE LA SIESTA, SARASOTA, FL 34242
$4,900,000132 Days on yellowkey MLS ID: A4682172
Bed: 9 Bath: 0.0 Liv Area Sq Ft: 4437 Built: 1999 Tax: $22,056 (2025)Community: Sarasota BeachSpa: YesMulti-Family 5+
Taxes:$22,056
Remarks: 5.9% Seller Financing and Nightly rentals, a unicorn. This 7-unit investment property is unique in that it operates more similar to hotel than a single family vacation rental. It has years of returning guests and it's one of very few elevated properties allowing the former mentioned, nightly rentals. 2-studios, 2-1 bedrooms, 2-2 bedrooms, and a penthouse suite with wrap around balcony. Your guests will enjoy a great pool area, sizable covered space with a grill, on site laundry, and a roof top deck. It's 1 block to both the Village and beach, guests walk everywhere. Park your car in one of the 7 newly pavered spaces and don't start it again until the vacation is over. Now for you the owner, a private office/guest check in, 2 storage areas for linens housewares etc, and a commercial laundry for turnovers. These types never trade, don't let another 20 years pass before this sells again.
Listing Agent: Jason Skowronski (941-812-6090)
5169 OXFORD DR, SARASOTA, FL 34242
$1,498,80067 Days on yellowkey MLS ID: V4948468
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1658 Built: 1994 Tax: $15,228 (2024)Community: Siesta BeachSpa: NoSingle Family
Taxes:$15,228
Remarks: Under contract-accepting backup offers. WATERFRONT PARADISE!! Welcome to 5169 Oxford Drive, where this elevated, turnkey-furnished home is perfectly positioned on a stunning canal, offering the ideal opportunity for personal enjoyment or rental income. This beautifully maintained property features 3 bedrooms and 3 bathrooms, along with quick access to open water, making it a dream for boating enthusiasts. Start your mornings with a relaxing cup of coffee or tea in your backyard oasis by the private swimming pool. As the day unfolds, gather with family and friends in the warm, inviting living room while enjoying tranquil canal views. The open-concept layout is designed for effortless living, seamlessly connecting to a chef-inspired kitchen just steps away. Upstairs, you’ll find a spacious bedroom and full bathroom, perfect for guests or added privacy. Downstairs features two en-suite bedrooms, providing comfort and convenience for everyone. Step outside to your own private retreat—ideal for entertaining or unwinding. Spend evenings by the pool, fire up the barbecue, or fish right from your private dock and pier. For adventure, grab your paddleboard and head straight out to the Gulf from your backyard. This home showcases exceptional features and thoughtful upgrades throughout, including: • Durable steel roof • Updated flooring • Indoor laundry • Outdoor grilling area • Private swimming pool • Boat slip • Private fishing pier Located just moments from Siesta Beach, you can easily hop on your golf cart or enjoy a scenic walk to one of Florida’s most beautiful shorelines. This is more than just a home—it’s a lifestyle. Seller is offering a one-year home warranty with a full-price contract. Schedule your private showing today and experience this exceptional property and neighborhood firsthand.
Listing is courtesy of: THE C SMITH REAL ESTATE GROUP LLC (407-705-7797)
Listing Agent: John Chalkias (614-284-2560)
5790 MIDNIGHT PASS RD #506, SARASOTA, FL 34242
$1,200,000103 Days on yellowkey MLS ID: A4686142
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1335 Built: 1979Monthly Fee: $1,647 Tax: $10,130 (2025)Community: Gulf & Bay Club Ph 1Condo
Taxes:$10,130
Remarks: Gulf-front views at the Gulf & Bay Club, resort living on Siesta Key! Ideally on the fifth floor of the A Building in Gulf & Bay Club, this expansive two-bedroom residence showcases sweeping Gulf views and the signature lifestyle only Siesta Key ownership provides. With 1,335 square feet of interior living space and private lanai, this property delivers coastal elegance and remarkable comfort in one of Sarasota’s loved beachfront addresses. An open floor plan with tranquil Gulf/beach views. New luxury vinyl wood flooring through main living space and comfortable carpet in both bedrooms. Designed for effortless entertaining, the open living and dining areas connect seamlessly to a stunning Gulf-facing view, ideal for sunset gatherings or quiet mornings with ocean breezes. The new updated kitchen pairs functionality with style, offering solid wood cabinetry, stone counters, a center island and all new stainless appliances. The primary suite is a private retreat, complete with walk-in closet, lanai access, and a luxurious updated en-suite bath featuring dual vanities and a large shower. The guest suite is a generously sized bedroom which provides privacy for family and visitors. An additional feature is a spacious laundry room. The Gulf & Bay Club on Siesta Key delivers unmatched amenity experience. The building boasts an array of amenities designed to elevate everyday living, including on-site management for added convenience. Two electric vehicle charging stations that are available, three large heated pools with Wi-Fi including one lap pool, 800 feet of private soft white sandy beach, six tennis courts including one Har-Tru court, six pickleball courts, basketball/racquetball/pickleball courts, shuffleboard court, organized seasonal golf for men and women, State-of-the-art fitness center, including free weights and yoga room, six dry saunas, hot tub, two clubhouses, library with books, bar, pool table and TVs. Numerous social activities during season, and the world-famous Siesta Key Beach directly on the beautiful Gulf of Mexico, featuring spectacular sunsets. This property serves as a tranquil retreat in an exceptional location whether you're seeking a permanent residence or a vacation getaway.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Lisa Gullick (941-364-4000)
6204 MIDNIGHT PASS RD #205, SARASOTA, FL 34242
$775,000166 Days on yellowkey MLS ID: A4676979
REDUCED by $4,000 (0.5%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1979Monthly Fee: $1,243 Tax: $6,173 (2025)Community: Siesta Dunes BeachCondo
Taxes:$6,173
Remarks: Welcome to your slice of paradise at Siesta Dunes Beach Community. This beautifully maintained 2-bedroom, 2-bath end-unit is located on the second floor and is offered turnkey furnished, making it ideal as a vacation getaway, investment property, or full-time residence. Being an end unit, the condo is filled with extra natural light and offers a charming peek-a-boo ocean view to remind you just how close you are to the beach. Enjoy peace of mind with recent upgrades, including a newer AC, newer roof, and brand-new impact windows (2025). The unit includes a covered parking space and the community provides private beach access and beach chairs, so you’re ready to enjoy the Siesta Key lifestyle from day one. With weekly rentals allowed, this property offers excellent rental potential in a highly desirable beachfront community. Whether you’re relaxing on the sand or generating income, this Siesta Dunes condo checks all the boxes for coastal living which will not disappoint.
Listing Agent: Christine Green (941-914-2463)
1350 N PORTOFINO DR #107, SARASOTA, FL 34242
$373,900305 Days on yellowkey MLS ID: A4662545
REDUCED by $1,000 (0.3%) on 05/17/2026
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 #537 with plenty of guest parking. Outdoor grilling SPOT. Rental friendly but no pets except authentic guide dogs. PRICED BELOW MARKET AT $373,900 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)
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