Location: Sarasota , 34242
Do Not Show Listings
5108 SANDY SHORE AVE, SARASOTA, FL 34242
$1,050,00020 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,305
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
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)
6910 MIDNIGHT PASS RD #B, SARASOTA, FL 34242
$2,895,000Listed 06/10/2026 4:29PM MLS ID: A4694978
Bed: 6 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2801 Built: 2021 Tax: $22,665 (2025)Community: Point Of Rocks TerraceSpa: YesApartment
Taxes:$22,665
Remarks: There Is Only One. Point of Rocks. Crescent Beach. Captain Curt's. For generations, this stretch of Siesta Key has attracted families, vacationers, and investors alike, and that demand has endured year after year for what seems to be one simple reason: people never seem to stop coming back. Positioned just moments from beach access located at the end of the street, Point of Rocks is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, waterslide, and expansive indoor-outdoor living spaces designed to accommodate up to fourteen guests. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment potential. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
5855 MIDNIGHT PASS RD #514, SARASOTA, FL 34242
$478,0005 Days on yellowkey MLS ID: OM724368
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 751 Built: 1976 Tax: $3,878 (2025)Community: Harbor TowersCondo
Taxes:$3,878
Elementary School: None
High School: None
Middle School: None
Remarks: COASTAL RESORT LIVING JUST MINUTES FROM SIESTA KEY BEACH! Enjoy the best of Siesta Key living in this beautifully updated and move-in-ready condominium at Harbor Towers, one of the island's most sought-after waterfront communities. Located just a short distance from the world-renowned Siesta Key Beach, this large one-bedroom, one-bath residence offers beautiful bay and intracoastal water views, exceptional amenities, and outstanding ownership value. Recent improvements provide peace of mind, including a new air conditioning system (2026), new hot water heater (2026), fresh interior paint, a new window, and a new screened lanai door. The spacious floor plan features an oversized bedroom with room for multiple sleeping arrangements, generous closet space, a full-size kitchen with refrigerator and dishwasher, keypad entry, and abundant natural light. Harbor Towers offers an impressive collection of resort-style amenities, including a heated pool and spa, fitness center, marina, fishing pier, boat slips available for lease, tennis courts, clubhouse, walking paths, grilling areas, and secured gated access. A deeded covered parking space is conveniently located near the building entrance. Ideal as a primary residence, vacation getaway, or investment opportunity. Historical rental activity reflects gross rental income of approximately $34,000 annually; future rental income may vary. All special assessments have been paid, HOA fees are paid through 2026, and there are no other outstanding fees, providing added peace of mind for the next owner. Ideally situated near Siesta Key Village, residents enjoy convenient access to restaurants, shopping, entertainment, and beach access, with trolley and transportation options nearby. Experience the convenience, amenities, and coastal lifestyle that make Harbor Towers one of Siesta Key's most desirable waterfront communities. With elevator access, a practical layout, convenient amenities, and low-maintenance living, this residence offers comfort and ease of ownership.
Listing is courtesy of: ENGEL & VOLKERS OCALA (352-820-4770)
Listing Agent: Jamie Zeigler (863-969-9145)
420 BEACH RD #606, SARASOTA, FL 34242
$1,595,000104 Days on yellowkey MLS ID: A4683822
REDUCED by $90,000 (5.3%) on 05/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1980 Tax: $8,066 (2025)Community: Siesta Gulf ViewSpa: NoCondo
Taxes:$8,066
Remarks: This Rare Beachfront, Classic Coastal Modern extensively renovated 2/2 condo has your Dream View! Unobstructed Beach View of 400’ of private beach on 7 acres. Offering total building area for unit is 1568 sq ft. Modern appointed living area is 1316sq ft with additional 252 sq ft Modern Private Lanai. High demand all year Monthly (12) rentals for Investor, 2nd Home or Primary Home. There are No assessments. Passed Structural Integrity. Strong, Fully Funded Reserves. Replaced cast iron to New “PVC” drains in entire building, New building roof, New clubhouse roof lowered insurance master policy. Stilted Building, Designated Parking underneath offers weather protection to lobby/elevator. Condo has Brand New HVAC 2026 with R454B gov. required cooling & New Water Tank. Designed by Owner, Floor to Ceiling integrating a cohesive Classic Modern Art Gallery feel throughout. Enjoy your “private outdoor living” new screened 31’x8’ Beach Lanai (no houses/buildings in line of sight) Modern flooring, locking storage Door. Unit is insulated & extremely “Quiet” w/updated PGT impact Sliders and Windows. Solar Shades are see-through when down on sliders but front windows have see-through Solar Shades & Privacy Shades. The Front has Quiet Solid Core impact Door same as lanai. Stunning Modern Polished Porcelain, Large Rectified 24” Tile for entire condo & closets. Modern Frosted Glass Framed Solid Wood 4 Interior Doors. Frosted Glass Framed Solid Wood Interior Bifolds for all 7 closets. Continuing the clean line design, 8” Solid Wood, Mitered Baseboards throughout. For the Art of Lighting, all LED lighting has dimmers throughout & walk-in closets. All Closets designed w/Solid Wood Shelving & fitted w/thick satin nickel Rods and Brackets to All Studs for Heavy organization needs. Both Bathrooms have Moreno Gloss Floating Soft Close Drawer Vanities w/satin nickel Series Pfister Kenzo Waterfall Faucets/Shower Handel & 4 piece Towel bar set. Kohler Skirted “Chair-Height” Toilets for both. Main bath is Designed w/24” Italian Carrera Marble Tile, full size Bench & tall Niche. Guest bathroom Designed w/24” Ivory Glass Tile & Tall Abalone Tile Niche. With owners not being a chef/cook, kitchen is gently used in immaculate condition. ALL "SMART Wi-Fi" Stainless Appliance Suite, Largest Size features; “Double Oven” 5 burner w/Warming Drawer. Refrigerator “Showcase” Triple French Door, ice/water, Middle Flex Drawer, Bottom Freezer Double Drawer. Stainless “Triple Storm” Dishwasher. Kohler 36” Large Stainless Steel Apron Sink w/Kohler Pull down stainless Faucet. Matching to Suite are Over Size Stainless "Wi-Fi" Front Load Washing Machine & Front Load Dryer on Stainless Pedestals in “walk-in” Laundry Room, dimming LED lights, solid wood shelving w/nickel stainless rod/brackets designed for Heavy storage needs. Owner has variety remodeled Product in front closet. This beachfront condo has been gently lived in and all the Design Aspects/Appliances are in Immaculate Condition. Clubhouse with 25‘x40‘ Heated Swimming Pool, Tennis & Pickleball Courts, updated Fitness room, bathrooms, your private locked Storage Room. Private Beach gate to Boardwalk w/ picnic area, 2 grills & birdwatching benches. Pet friendly with designated large pet park with bench. “Private ISLAND Style Living” A truly Rare opportunity awaits you- private unobstructive full length lanai beach front view, 6 floor, 7 acre property, 400’ beachfront Property is available for Same Day Showings.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Constantine Stratos (941-232-5251)
6144 MIDNIGHT PASS RD #3N, SARASOTA, FL 34242
$1,385,0001 Day on yellowkey MLS ID: A4696434
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1376 Built: 1967 Tax: $16,658 (2025)Community: Island HouseCondo
Taxes:$16,658
Remarks: Island House Dream Condo on Siesta Key! Experience the best of beachfront living at Island House on world-famous Siesta Key, where breathtaking Gulf views, unbeatable location, and effortless island living come together. Perfectly positioned in one of the most desirable beachfront buildings in the community, this second-floor condo offers truly unobstructed beach and water views with no other condo or building standing in your way. From the moment you arrive, the view takes center stage. Enjoy stunning beach views from all living areas, including the living room, guest bedroom, and master bedroom. New hurricane-impact windows and expansive glass bring the beauty of Siesta Key inside, creating a bright, open, coastal retreat from every angle. This is as close to the sand as it gets—literally beachfront and just steps from the world-famous powdery sand and warm Gulf waters. The elevated second-floor setting gives you the privacy and peace of mind you want, with no past water intrusion or storm damage to the unit, while still offering easy access to the beach and a convenient ramp for luggage. Inside, the condo is move-in ready and designed for easy beach living, featuring tile flooring throughout, an updated kitchen with solid-surface/granite counters, and beautifully updated bathrooms with elegant tiled showers. Whether you are looking for your own Siesta Key escape or an income-producing investment, the flexible 3-night minimum rental policy makes this an outstanding opportunity. Island House offers everything you need for the perfect beach lifestyle, including on-site management, refreshed landscaping, outdoor dining and game areas, beach chairs, chaise lounges, shaded beach cabanas, shuffleboard, cornhole, a heated community pool, and a clubhouse with billiards, foosball, board games, and puzzles. When you are ready to explore, hop on the free trolley or local ride-share vans to Siesta Key Village for shopping, dining, and nightlife, or venture to Turtle Beach, downtown Sarasota, restaurants, boating, fishing charters, performing arts, museums, parks, and the Legacy Trail. This is more than a condo—it is your front-row seat to Siesta Key’s legendary beach lifestyle. Bring your toothbrush, swimsuit, and love for sunsets, because this one is ready to enjoy!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Christine Walker (941-779-4342)
1250 N PORTOFINO DR #202, SARASOTA, FL 34242
$469,90013 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
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)
20 WHISPERING SANDS DR #1201, SARASOTA, FL 34242
$1,195,000150 Days on yellowkey MLS ID: A4678026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,398 Tax: $10,552 (2025)Community: Whispering SandsCondo
Taxes:$10,552
Middle School: Brookside Middle
Remarks: A truly RARE offering, this TOP floor, GULF FRONT penthouse residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL GULF views from this unit unfurl in every direction, offering a daily masterpiece of colors that shift with the rising and setting sun. Wake up to breathtaking Gulf views that seem to stretch to infinity, offering a tranquil retreat from the ordinary. In the evening, enjoy the golden hues of Florida sunsets and starlit dinners from your expansive 28’ balcony, where the Gulf breezes and soft cries of the seagulls serve as the perfect soundtrack. This penthouse is more than just a property – it’s also a canvas for your imagination. Distinctive architectural elements and premium untapped potential invite you to curate a space that reflects your own unique style and vision. Whether you envision modern sophistication, coastal charm, or timeless elegance, the untapped possibilities of this unit invite your imagination to run free as you create the ultimate sanctuary tailored to your personal vision. Whispering Sands' relaxed, informal lifestyle provides the perfect backdrop for your next chapter. Start your day with a set of vigorous laps or water aerobics in one of two beautiful, heated pools - one beachside, one clubside. You’ll never need to leave the property to get your gym workout in the main clubhouse currently undergoing a complete remodel. Plant your feet in the cool quartz sand and enjoy daily dips in the balmy Gulf. Beach loungers are set out daily for the exclusive use of owners. Enjoy an impromptu game of beachside shuffleboard followed by a picnic supper at the Tiki Hut. Whether spending time exploring the vibrant cultural offerings of Sarasota just across the North Bridge, indulging in the local arts scene, or simply relaxing on your breezy private balcony with a good book, the options this property offers are endless. Secure your private viewing of this unique residence and claim your place in this coveted coastal community!
Listing Agent: Harriet Stopher (404-316-8944)
5830 MIDNIGHT PASS RD #T22, SARASOTA, FL 34242
$1,000,00062 Days on yellowkey MLS ID: A4689210
1 Days Off yellowkey (back on 4/20/2026)
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)
1320 MOONMIST DR #B-11, SARASOTA, FL 34242
$1,200,000139 Days on yellowkey MLS ID: A4679270
REDUCED by $100,000 (7.7%) on 04/13/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1790 Built: 1968 Tax: $5,819 (2025)Community: Polynesian GardensCondo
Taxes:$5,819
Remarks: Rarely available direct bayfront 2/2 maintenance free villa in Polynesian Gardens. Magnificent views of the Intracoastal/Little Sarasota Bay. Watch the manatees and boats go by from your paved patio directly on the water. Spacious 2 bedrooms/2 full baths with very large great room. Updated kitchen and baths with new cabinetry, granite and stainless-steel appliances. Plenty of closet space. Garage with plenty of storage plus an extra driveway allows for 2 parking spaces. Newer washer/dryer in garage. Beautiful landscaping. Community has a heated pool, clubhouse and fishing pier. Close to shops, dining and America's #1 Beach - Siesta Key. Free trolley stops directly in the front of the community on Midnight Pass Road. Two pets allowed any size.
Listing Agent: Helene Hyland (941-685-2274)
1800 COVE II PL #213, SARASOTA, FL 34242
$595,00010 Days on yellowkey MLS ID: A4695562
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 860 Built: 1979 Tax: $5,863 (2025)Community: Midnight Cove IiCondo
Taxes:$5,863
Remarks: Fully Funded Reserves & Passed SIRS Inspections! 2 Bedroom, 2 Bath First-Floor Condo with Screened Lanai on fabulous Siesta Key Across from Crescent Beach – Just Steps from Siesta Key Beach! This turnkey furnished, beautifully maintained 2-bedroom, 2-bathroom condo is located on the first floor and offers the perfect blend of comfort and convenience. Enjoy stunning views of the Intracoastal Waterway right from your screened lanai. The property is fully funded for reserves and has passed the required SIRS inspections, providing peace of mind for the new owner. Key Features: Turnkey Furnished: Move-in ready with everything you need. Location: Prime location on Siesta Key, just across the street from Crescent Beach and an easy walk to world-renowned Siesta Key Beach. Views: Enjoy picturesque views of the Intracoastal Waterway from your lanai. Community Amenities: Marina with dock space available for rent or purchase. Fitness center and basketball court for active living. Heated pool for year-round enjoyment. Rental Opportunities: Midnight Cove II allows 1-week rentals, offering great potential for short-term rental income. The on-site office is optionally available to handle rentals on your behalf, making it a hassle-free investment. This property is an excellent opportunity for investors or those seeking a relaxing retreat in one of Florida’s most desirable locations. Schedule your private showing today!
Listing is courtesy of: EXCEPTIONS REALTY (941-536-8378)
Listing Agent: Peter Lev (941-536-8378)
5740 MIDNIGHT PASS RD #104F, SARASOTA, FL 34242
$1,375,000138 Days on yellowkey MLS ID: A4679012
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $9,698 (2025)Community: Gulf & Bay Club Ph6Spa: YesCondo
Taxes:$9,698
Remarks: Incredible Gulf-front first-floor residence (10’ elevation) within the amenity-rich 32-acre campus of the Gulf & Bay community on Siesta Key. This 2-bedroom, 2-bath furnished condominium is ideally positioned in the highly desirable F Building and offers direct walk-out access to the beach with unobstructed views of 800 feet of private shoreline and the expansive Gulf of Mexico. Just steps from the sand, this exceptional location delivers the ultimate Gulf & Bay lifestyle—blending convenience, privacy, and breathtaking coastal scenery. This unit did not flood during recent storms. The remodeled kitchen features abundant cabinetry, a beverage cooler, and a comfortable eat-in area with a built-in desk. The primary suite captures beautiful Gulf views and includes a walk-in closet plus an additional wall closet. The en-suite bath has been tastefully remodeled with a frameless travertine shower, dual vanities, and a dedicated makeup area. The spacious guest bedroom offers two full Murphy beds, providing flexible sleeping accommodations. Additional highlights include a new A/C system (2025), 20" x 20" tile throughout the main living areas, and smooth ceilings—no popcorn. Gulf & Bay is truly one of the best resort complexes on Siesta key featuring: 2 clubhouses, 3 heated pools, pickleball courts, tennis courts (1 HarTru), well equipped fitness center, hot tub, multiple grill areas all leading out to World Famous, gorgeous Siesta Key Beach!
Listing is courtesy of: ANDREWS & ASSOCIATES REALTY (941-921-5999)
Listing Agent: Tony Andrews (941-921-5999)
5179 HIDDEN HARBOR RD, SARASOTA, FL 34242
$7,950,000234 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
Tax Year: 2024
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.
137 AVENIDA MESSINA #3, SARASOTA, FL 34242
$625,000134 Days on yellowkey MLS ID: A4680216
REDUCED by $15,000 (2.3%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1966 Tax: $5,716 (2024)Community: Villa NavarraCondo
Taxes:$5,716
Remarks: Discover this beautiful upstairs furnished condo in a highly desirable complex that is ideally situated in the Mira Mar neighborhood adjacent to the Siesta Key Village! Just a short stroll to the beach and mere moments from top dining, shopping, and nightlife, this unit is the ultimate coastal escape. Enjoy worry-free living with impact windows and sliding doors, a 2024 washer/dryer in the unit, and a 2022 water heater. NEW ROOF, no assessments, and no flooding concerns make this an exceptional find! Both the bathrooms and the kitchen have been tastefully renovated with sleek quartz countertops. The entire unit features neutral ceramic plank-tile flooring and a cohesive neutral palette throughout. Unwind on your screened in lanai, enveloped by lush palms and tropical greenery. Leave your car at home and soak in the beauty of Siesta Key Beach—ranked the #1 beach in the U.S. You are just 2/10 of a mile away from Sunset Pier where pristine white quartz sand, crystal-clear waters, and breathtaking sunsets await. Whether you're seeking a primary residence or the perfect island getaway, this beautifully maintained boutique community of just 16 condos offers an unbeatable location. Don’t miss this rare opportunity!
Listing Agent: Jackie De Manio Eberley (201-233-1959)
5155 HIDDEN HARBOR RD, SARASOTA, FL 34242
$1,995,000139 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)
5103 WINDWARD AVE, SARASOTA, FL 34242
$3,539,000159 Days on yellowkey MLS ID: A4676707
REDUCED by $10,000 (0.3%) on 06/10/2026
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!
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
6140 MIDNIGHT PASS RD #501, SARASOTA, FL 34242
$1,795,00064 Days on yellowkey MLS ID: A4688820
REDUCED by $100,000 (5.3%) on 06/08/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1798 Built: 1967 Tax: $16,236 (2025)Community: Horizons WestCondo
Taxes:$16,236
Remarks: Spacious and inviting, this TRUE 3-bedroom, 5th-floor end-unit condominium is located directly on Siesta Key’s world-renowned quartz crystal sand beach and offers sweeping west-facing Gulf and Crescent Beach views from Point of Rocks to northern Siesta Key. Enjoy water views from every room in this updated, move-in-ready residence that comes fully turnkey furnished—just bring your suitcase and start enjoying the beachfront lifestyle. Featuring IMPACT windows and doors for peace of mind, this coastal retreat is nestled within the desirable Horizons West, a Gulf-to-Bay resort set on over 7 beautifully landscaped acres. Amenities include 300 feet of deeded beach access with cabanas, a beachside pool and spa, grilling areas, a second pool by the clubhouse, and a private Intracoastal Waterway park with day dock ideal for fishing, picnicking, or watching boats pass by. Launch kayaks and paddleboards from the bayside to explore the mangroves, or hop on the free Siesta Key trolley to experience the island’s exceptional dining, shopping, and entertainment.
Listing Agent: Suki Scollo (941-587-2289)
4660 OCEAN BLVD #Q2, SARASOTA, FL 34242
$624,90041 Days on yellowkey MLS ID: A4692194
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971 Tax: $6,131 (2025)Community: Sea VillageSpa: NoCondo
Taxes:$6,131
Remarks: Stunning Sunset Views ~ Sea Village on Siesta Key. Wake up to breathtaking water views and enjoy legendary Siesta Key sunsets from this beautifully maintained 2-bed, 2-bath, perfectly positioned condo in a charming Gulf front community. Floor-to-ceiling glass sliders flood the open living area with natural light, leading to your private screened lanai, where uninterrupted Gulf views are yours to behold. The primary bedroom features sliding doors that open to the patio, ample closet space, and an ensuite bath with separate vanity. The well-appointed kitchen has upgraded appliances and a pass-through to the living area, and the second bedroom is perfect for guests and family. With 1,200 ft² of living space, this second-floor residence has a brand-new A/C (2025) and offers an in-unit washer/dryer, as well as a free community laundry room and storage. This exceptional unit has had just one owner and has been in the family since the complex was built. Sea Village is a small, pet-friendly community located exactly 1 mile north of Siesta Key Village and 1 mile to the #1 Beach in America. Amenities include not one, but TWO heated waterfront pools, a newly constructed fishing pier, and designated covered parking. Renowned for its vibrant coastal lifestyle, Siesta Key Village is bustling with restaurants, cafes, shops and miles of crystalline beaches. Downtown Sarasota’s Bayfront, with its world-class shopping, dining, & cultural events is 5 miles away. Nature lovers, sports enthusiasts, and patrons of the arts have the best of Sarasota at their fingertips with outdoor activities that include waterfront dining, boating, biking, golfing, hiking & fishing nearby. With easy access to state-of-the-art medical facilities, Sarasota International Airport, and the I-75, the location of this property offers the perfect blend of serenity & convenience and offers an extraordinary opportunity to live your best life, whether it be used as a private retreat for your own personal enjoyment, or a seasonal or annual rental, with excellent income potential. Monthly HOA covers Community Pool, Escrow Reserves, Insurance, Exterior Maintenance (including the roof), Maintenance of the Grounds, as well as Water, Sewer and Trash. A complete beautification project of the community is slated to be completed in June, to include all new landscaping and brand new carports. PLEASE NOTE: Some of the aerial photos in this listing were taken previously.
Listing Agent: Robin Leonardi (941-685-6270)
6285 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$643,000399 Days on yellowkey MLS ID: A4651246
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1981 Tax: $6,349 (2024)Community: Excelsior Beach To Bay 5Spa: YesCondo
Taxes:$6,349
Remarks: Tremendous value for this 4th-floor condo at the Excelsior Beach to Bay complex on Siesta Key. Coveted for its soaring ceilings and the opportunity to add a bona fide upper-level third bedroom, this bayside penthouse offers exciting potential to create a luxurious full-time residence or home away from home. It is lovely as-is,with some thoughtful updates over the years including granite countertops, stainless appliances, updated flooring and carpeting, plus a 2025 AC system and water heater. A pre-listing home inspection has been completed and is available for review. This south-facing unit is filled with natural light and enhanced by clerestory windows. Owned by the same family since construction, the condo has been smoke-free, pet-free, and extremely well maintained. The screened lanai overlooks the grounds and could easily be enclosed if desired. Each condo includes a locked storage unit, and one assigned underbuilding parking spot with additional open/carport parking available for owners with a second car. Excelsior is rich with amenities, including two large heated swimming pools, poolside restrooms, hot-water showers, two hot tubs, tennis courts, pickleball courts, fitness center, gulf-side sun deck, beach lounge chairs, outdoor grills, Intracoastal fishing pier, community room with seassonal events, library, and catering kitchen. Walk to shopping, dining, bike rentals, and boat rentals. This ideal location offers direct deeded beach access to Siesta Beach renowned for its quartz sand that stays cool in the summer and feels like talcum underfoot. Enjoy easy on-and-off island access at the south Stickney Point Bridge, with the increasingly popular Gulf Gate neighborhood just over the bridge offering eclectic restaurants, grocers, pubs, and shops. Units here have a two week minimum an onsite Rental Manager. Absolutely one of the best values and opportunities at Excelsior, and perhaps on Siesta Key itself. A remarkable offering with these features and at this price which does not come along often.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Joan Winters (941-536-1714)
813 IDLEWILD WAY, SARASOTA, FL 34242
$3,795,0008 Days on yellowkey MLS ID: A4694937
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 4161 Built: 1969Monthly Fee: $17 Tax: $22,147 (2025)Community: Siesta Isles Unit 5Spa: YesSingle Family
Taxes:$22,147
Remarks: Tucked away near the end of a quiet cul-de-sac on an oversized, private waterfront lot in Siesta Isles with 109 feet of frontage on Siesta Key's Grand Canal, this exceptional 4,161-square-foot residence offers a rare combination of privacy, expansive living spaces, extensive upgrades, and breathtaking water views. Positioned at the canal's coveted "Big Bend," the home enjoys panoramic open-water vistas enhanced by neighboring county-owned green space, creating a lush natural backdrop and a remarkable sense of seclusion. Designed for both grand entertaining and everyday comfort, the light-filled floor plan features four bedrooms+bonus room, three full baths, multiple living areas, and rich wood flooring throughout. At the heart of the home is a gourmet chef's kitchen appointed with premium appliances, seamlessly connecting to an expansive great room where floor-to-ceiling glass frames stunning waterfront views. A separate entertaining bar features illuminated cabinetry, a wine refrigerator, sink, second Bosch dishwasher, and pass-through window to the lanai, making indoor-outdoor hosting effortless. The great room easily accommodates a dining table for ten while offering multiple gathering spaces to relax and enjoy the ever-changing waterfront scenery. The spacious primary suite serves as a private retreat, featuring a newly replaced waterfront deck and captivating water views from nearly every angle. Extensively upgraded with an emphasis on durability and peace of mind, the home features impact-rated windows and doors, recently replaced metal and flat roofs, two elevated HVAC systems, an elevated whole-house generator, mini-split air conditioning in the garage, two water heaters, extensive electrical upgrades, and all cast-iron sewer lines replaced with PVC. Outside, the resort-style living experience continues with expansive travertine patios, a heated saltwater pool and spa, multiple covered and open-air seating areas, and exceptional boating amenities including a new dock, 10,000-pound boat lift, and additional double jet ski/kayak lift. Professionally designed landscaping and architectural lighting enhance the home's tropical setting, creating a beautiful ambiance both day and night. With quick access to Roberts Bay and the Intracoastal Waterway, this property is perfectly suited for boating enthusiasts. Located just one mile from world-famous Siesta Key Beach and minutes from Sarasota's renowned dining, shopping, and cultural attractions, this extraordinary waterfront retreat offers the perfect blend of luxury, comfort, boating lifestyle, and privacy. This is truly A HOME FOR JOYFUL GATHERINGS!
Listing is courtesy of: MANGROVE REALTY ASSOCIATES (941-957-0080)
Listing Agent: Lori Madden (941-780-8443)
5855 MIDNIGHT PASS RD #327, SARASOTA, FL 34242
$659,000153 Days on yellowkey MLS ID: A4677414
0 Days Off yellowkey (back on 6/4/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1165 Built: 1976Monthly Fee: $735 Tax: $4,570 (2025)Community: Harbor Towers Y & RCondo
Taxes:$4,570
Remarks: Experience the ultimate in coastal living at Harbor Towers Yacht & Racquet Club-- a resort-style waterfront community on Siesta Key. This two-bedroom, two-bathroom west-facing condo offers breathtaking Gulf views and has been thoughtfully upgraded for modern comfort and style. Being sold turnkey furnished. Recently, the community completed a $13 million structural and hurricane upgrade program (2024), ensuring compliance with the latest safety standards for wind and storm protection. Featuring new hurricane-rated windows and doors, a beautifully appointed quartz kitchen with under-cabinet lighting, and updated baths with granite countertops and walk-in showers designed for ease of use. The open-concept living and dining area is bathed in natural light, creating a bright and welcoming space to relax and entertain. Harbor Towers is in a class of its own, offering an exceptional array of resort-style amenities, including: • A large marina with a fishing area and direct Gulf access (no fixed bridges) • Two heated pools for year-round enjoyment • Three Har-Tru tennis courts • Fully equipped fitness center & sauna • Clubhouse with social spaces • Outdoor BBQ and kitchen prep area • Serene waterfront seating areas to watch boats and marine life For boating enthusiasts, rental slips for personal watercraft are available through the association. Looking for an investment opportunity? This unit allows for two-week minimum rentals, with the option to utilize the on-site property management office or manage rentals independently. Whether you’re seeking a luxurious full-time residence, a vacation retreat, or an income-generating property, this vibrant, welcoming community is ready to embrace you. Don’t miss this rare opportunity to own a piece of paradise on Siesta Key!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Kelli Eggen (941-376-9844)
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