Location: Sarasota , 34242
Do Not Show Listings
814 PARADISE WAY, SARASOTA, FL 34242
$1,995,00056 Days on yellowkey MLS ID: TB8483961
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1996 Built: 1962Monthly Fee: $17 Tax: $14,830 (2025)Community: Siesta IslesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,830
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Exceptional Siesta Key waterfront residence offering a rare opportunity to own a turn-key, move-in-ready 4 bedrooms and 2 bathrooms home in one of the island’s most desirable and tranquil locations. Situated on a quiet cul-de-sac along a grand canal, the property provides privacy, scenic water views, and easy boating access to the Bay with only one higher bridge to navigate. A standout feature is the expansive Florida room, a light-filled living space designed for year-round comfort with floor-to-ceiling windows and seamless views of the water and surrounding greenery—ideal for relaxing or entertaining. The home has been thoughtfully maintained and is in excellent condition, allowing for immediate occupancy or rental income potential. Additional highlights include a heated pool, open and functional layout, and spacious living areas. Located just minutes from Siesta Key Beach and Siesta Key Village, this property combines prime location, generous living space, and waterfront charm, making it ideal as a primary residence, vacation home, or investment property. The house did not get flooded from the recent 2024 storms, a new roof was replaced in 2024, A/C was replaced in 2023, a pool heat pump was installed in 2023, re-piped and remodeled in 2022.
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
700 TROPICAL CIR, SARASOTA, FL 34242
$1,699,00059 Days on yellowkey MLS ID: A4684757
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2341 Built: 1977Monthly Fee: $54 Tax: $5,315 (2025)Community: Siesta BeachSingle Family
Taxes:$5,315
Elementary School: None
High School: None
Middle School: None
Remarks: Welcome to your private waterfront oasis, a meticulously renovated home set on a super private .41-acre lot defined by lush, mature greenery in one of Siesta Key’s most sought-after neighborhoods. The residence sits at a 9 foot elevation!! The interior features two primary bedroom suites, including a main retreat with a custom-built in closet. The open-concept layout has wide-plank light oak flooring and a kitchen with Italian cabinetry, waterfall quartz countertops, and a custom floor-to-ceiling built in cabinet pantry. Extensive structural and functional UPGRADES include a NEW ROOF, NEW STORM RATED WINDOWS AND SLIDERS, NEW DRAIN PIPES, and NEW PVC water lines. Transition through impact-rated glass sliders to a sun-drenched lanai and a new paver deck featuring a pool with all-new pool equipment. The backyard is a secluded tropical retreat bordered by a thick mangrove canopy for total privacy, offering direct water access for kayaking. Beyond the property, you are just minutes from the world-famous white sands of Siesta Key Beach, the vibrant dining and boutique shopping of Siesta Key Village, and a short drive to the cultural heart of Downtown Sarasota. From the designer finishes to the total structural renewal, this home offers security and luxury in a premier, verdant location. Call to set up a showing ~
Listing is courtesy of: CHIC PROPERTIES II LLC (941-302-0134)
Listing Agent: Ilona Davidovich (941-302-0134)
8534 HERON LAGOON CIR, SARASOTA, FL 34242
$1,299,00036 Days on yellowkey MLS ID: A4687653
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1153 Built: 1949Monthly Fee: $75 Tax: $5,695 (2025)Community: Heron Lagoon LodgesSingle Family
Taxes:$5,695
Remarks: A 2-minute walk across your private footbridge to secluded beach access, this 12,684-square-foot property in Heron Lagoon presents a rare opportunity to own in one of Siesta Key’s most intimate waterfront communities. The existing residence offers the potential to renovate or personalize, all while enjoying a tranquil lagoon setting. The property features a resort-style pool already in place which will need rehabbed, creating a strong foundation for an upgraded outdoor living space. With thoughtful improvements, this home can be transformed into a private coastal retreat that embraces indoor-outdoor living. Set within an exclusive enclave of just 13 homes — while this is 1 of 6 located on the water — residents enjoy a quiet, low-HOA community with direct access to kayaking, paddleboarding, fishing, and birdwatching. Private bridge access leads to a short stroll to Siesta Key’s world-renowned quartz-crystal beaches. Conveniently located just minutes from Siesta Key Village’s shops and dining, this property offers a unique opportunity to create your own island getaway. 3D renderings are available upon request for those seeking design inspiration.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Karlenn Peluso (941-356-5345)
1700 COVE II PL #324, SARASOTA, FL 34242
$849,90042 Days on yellowkey MLS ID: A4686403
Bed: 3 Bath: 3.5 Liv Area Sq Ft: 1720 Built: 1979 Tax: $7,965 (2025)Community: Midnight Cove IiTownhouse
Taxes:$7,965
Remarks: 3 BEDROOMS ON SIESTA KEY! ONE WEEK RENTALS! DEEDED BEACH ACCESS! WATER VIEWS! DOCKS AVAILABLE! Fantastic 3 bedroom townhouse at Midnight Cove II. 2nd and 3rd floor with lovely views and deeded beach access. Plenty of room for family and friends. Large sized living, dining and kitchen area. Perfect for family gatherings! Midnight Cove II offers deeded beach access directly across the street, marina with slips available, beautiful grounds, grilling area, tennis, pickleball, basketball court, fitness center and a large, heated pool. And bring the large pup too! Great association with onsite rental and management office. Fully funded reserves, milestone inspections complete! Turnkey furnished too! Walk to nearby dining, shopping, water sports and more. See this unit today!
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Kim Sheridan (941-313-0262)
1374 MOONMIST DR #B1, SARASOTA, FL 34242
$1,000,000400 Days on yellowkey MLS ID: A4642845
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1996 Built: 1968 Tax: $2,989 (2025)Community: Polynesian GardensVilla
Taxes:$2,989
Middle School: Sarasota Middle
Remarks: A $500K price reduction - don't wait! A rarely available bayfront opportunity to create your dream retreat on Siesta Key. Experience the allure of waterfront living in this detached bayfront villa, poised for a fresh vision in the desirable Polynesian Gardens community on Siesta Key. One of only 11 exclusive bayfront residences, this end-unit villa offers sweeping, unobstructed views of the Intracoastal Waterway from nearly every room, where sunrises paint the sky in breathtaking hues. Go outside to your expansive private waterfront deck, where you can unwind to the sights of boats gliding by, playful dolphins in the distance, and the peaceful rhythm of the bay. A natural beachfront at your doorstep invites you to dip your toes in the water and embrace the tranquil coastal lifestyle. Professionally remediated following Hurricane Helene, this residence is a blank canvas, ready for transformation. With a spacious two-bedroom, two-bath layout that exceeds the size of many three-bedroom villas in the community, the potential for a luxurious, customized retreat is limitless. Enjoy the privacy and convenience of your own garage and private entrance, delivering the feel of a single-family home, yet with the ease of villa living. The location is unbeatable, just minutes from the world-famous Siesta Beach, renowned for its soft quartz sands and mesmerizing Gulf waters, where mango-hued sunsets cap off each day. Centrally located on the island, you're moments from the vibrant dining, boutique shopping, and lively atmosphere of Siesta Key Village and South Siesta Village, and just a short drive to downtown Sarasota’s cultural arts scene, theaters, and fabulous dining. This is a rare opportunity to reimagine and create your custom bayfront sanctuary in one of Siesta Key’s sought-after communities. Don’t let this one-of-a-kind coastal gem slip away.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
225 HOURGLASS WAY #303, SARASOTA, FL 34242
$499,00036 Days on yellowkey MLS ID: TB8489788
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $5,476 (2025)Community: Whispering Sands Sec 2Condo
Taxes:$5,476
Remarks: 3RD FLOOR FLOODPROOF CORNER UNIT TOP FLOOR PENTHOUSE PRIVATE BEACH RESORT APPROX.1,665 sf. The Treehouse at Beautiful Whispering Sands Siesta Key the World's Finest White Sand Beach. This is a unique opportunity to own a rare corner unit on the green belt Not a Parking Lot View, double Lanai flood proof no damage from Hurricanes. The breeze you get going through this condo is incredible, also there is brand new AC unit for the hotter months this is a must see condo. 800 ft of PRIVATE BEACH two private heated pools Clubhouse workout facility and more.
Listing is courtesy of: HOMECOIN.COM (888-400-2513)
Listing Agent: Jonathan Minerick (888-400-2513)
3799 FLAMINGO AVE, SARASOTA, FL 34242
$18,500,000343 Days on yellowkey MLS ID: A4653658
Bed: 4 Bath: 5.0 Liv Area Sq Ft: 8138 Built: 2016 Tax: $109,657 (2024)Community: Siesta Key / Bay IslandSingle Family
Taxes:$109,657
Tax Year: 2024
Remarks: Relax and take in the positive energy of Lotus-style living in this one-of-a-kind Balinese-inspired resort compound on north end of the world-famous Siesta Key. Nothing is needed to begin your Zen journey as the property comes completely furnished down to dishes, silverware and a Buddha living wall. The coexistence of indoor and outdoor space blends over 8,000 square feet of indoor space with thousands of square feet of patio and pool area. An outdoor oasis offering an infinity-edge pool with a swim-up bar, a sunken fire pit lounge within the pool, a spa, an outdoor kitchen, a dining pavilion with a living plant wall and an open-air living room with a fireplace. A koi pond with stunning built-in footbridges stretches nearly the entire length of the home, enhancing the serene ambiance of the outdoor space. Spanning over an acre with more than 700 feet of waterfront, the property is a masterpiece of luxury, designed for effortless relaxed living or island-style entertaining. A custom-designed driveway welcomes you to a breathtaking entrance, where waterfalls and fire features set the tone for the experience that awaits inside. Expansive walls of glass, seamless indoor-outdoor transitions, and rich wood and stone flooring throughout create a striking, cohesive aesthetic. The thoughtfully designed interior boasts multiple living spaces, including a game room, home theater, fitness room, meditation space and an impressive 8-plus-car garage. For the waterfront enthusiast, a well-equipped boat dock, a separate waterfront garage, and a paddleboard/canoe launch provide unparalleled access to pristine waters. This exceptional residence also features a newer seawall, full-house generator, Crestron home automation, a three-stop elevator and a whole-house reverse-osmosis water filtration system, ensuring convenience and peace of mind. An island paradise, this estate offers unmatched privacy while remaining just moments from Sarasota’s vibrant shopping, dining and world-renowned cultural attractions. Don’t miss this rare opportunity to own a move-in-ready masterpiece on Siesta Key – home to the #1 beach in the USA (Tripadvisor).
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
3460 FLAMINGO AVE, SARASOTA, FL 34242
$7,749,00063 Days on yellowkey MLS ID: A4683051
3 Days Off yellowkey (back on 3/30/2026)
Bed: 5 Bath: 6.5 Liv Area Sq Ft: 6030 Built: 2026 Tax: $30,144 (2025)Community: Bay IslandSingle Family
Taxes:$30,144
Remarks: Under Construction. An extraordinary opportunity awaits on the coveted north end of Siesta Key. Currently under construction and scheduled for completion in late 2026, this magnificent waterfront estate offers the rare chance to personalize finishes and create a truly bespoke coastal masterpiece—without the years-long process of designing, permitting, and building. Set on a remarkable and rarely available 1.25-acre estate-sized lot with direct sailboat water frontage, the property provides unobstructed access to Sarasota Bay and the open waters of the Gulf of Mexico. Boating enthusiasts will appreciate the deep-water access with no bridges to the bay, offering seamless days on the water from your own backyard. The custom-designed residence encompasses over 6,000 square feet of refined living space, thoughtfully planned to blend grand scale with effortless coastal elegance. Expansive indoor-outdoor living areas, soaring ceilings, and walls of glass are designed to capture tranquil water views and Gulf breezes. Buyers have the exclusive opportunity to select interior finishes, fixtures, and design elements—tailoring the home to their personal vision while benefiting from the expertise and timeline already in place. Complementing the main residence is a private guest house, ideal for hosting family and friends in comfort and style. The true estate setting is further enhanced by a full-sized tennis court, lush grounds with room for additional amenities, and the privacy rarely found on waterfront properties. This is a once-in-a-generation opportunity to own a newly built waterfront compound in one of the Gulf Coast’s most sought-after locations—where luxury, space, convenience and converge. These images are architectural renderings created for illustrative purposes only and are based on preliminary plans and design concepts. Renderings are intended to convey the overall vision, layout, and design intent but are not exact representations of the final constructed residence. Actual materials, finishes, dimensions, landscaping, fixtures, furnishings, ceiling details, lighting, views, and architectural elements may vary. All features, specifications, and details are subject to change without notice.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Jennifer Linehan (941-266-7555)
1054 SUN N SEA DR #106, SARASOTA, FL 34242
$660,00053 Days on yellowkey MLS ID: A4685194
0 Days Off yellowkey (back on 3/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 800 Built: 2009 Tax: $6,023 (2025)Community: Beach Club At Siesta KeyCondo
Taxes:$6,023
Remarks: Under contract-accepting backup offers. Siesta Key investment property and nightly rental opportunity at Beach Club at Siesta Key, approved for true nightly vacation rentals near world famous Siesta Key Beach. Historical rental income approaches $83,000 annually, with modeled revenue potential exceeding $103,000 if owner use nights were made available for rental. Historical bookings show approximately 209 reserved nights annually with average nightly rates between $397 and $450, creating a strong income producing profile relative to the $660,000 list price. Detailed rental history, booking records, and revenue analysis are available for review. Few properties on Siesta Key combine true nightly rental eligibility, documented rental performance approaching $83,000 annually, modeled revenue potential exceeding $103,000, extensive renovation, and resort style amenities within this price range. Unit 106D is the largest floor plan in the community and is positioned as a private corner residence overlooking the heated resort style pool with minimal foot traffic. Built in 2009 with elevated construction, the building sustained no storm related damage. This Unit has been recently and extensively renovated beyond prior community finishes. While some online rental marketing may reflect earlier interiors, the unit now features luxury vinyl plank flooring throughout, matching quartz countertops in the kitchen and bathrooms, updated cabinetry, stainless steel appliances, modern fixtures, and renovated kitchen and bath spaces. A full size washer and dryer supports guest convenience and longer stays. From entry, the space presents more like a boutique resort suite than a typical beach rental. Upgrades were selected for both visual appeal and rental durability. Offered fully furnished and turnkey, the property is positioned for immediate continuation of nightly rental operations. A detailed 3D virtual tour is included with the listing to allow buyers to explore the residence remotely. Due to consistent guest bookings, showing availability may require advance coordination. Ownership allows up to 120 days of personal use annually while maximizing income through nightly rentals. Professional on site management handles reservations, guest communication, cleaning, and maintenance. Community amenities include a heated pool, hot tub, grilling areas, shared patio spaces, complimentary beach chairs and umbrellas, on site office support, and gated beach access to Siesta Key Beach. Located near the South Bridge with Crescent Market and the restaurants, bars, and shops of Siesta Key’s South Village just around the corner. Recent interior updates and the residence’s desirable pool view location create additional opportunity for increased booking activity and nightly rates as updated photography and marketing are introduced. Historical booking data demonstrates consistent guest demand and strong occupancy, while analysis of owner use nights indicates additional revenue potential depending on preferred usage strategy. Properties offering true nightly rental flexibility with Siesta Key Beach access, documented rental performance approaching $83,000 annually, modeled revenue potential exceeding $103,000, and extensive renovation rarely become available within this price range on Siesta Key. Detailed rental history, booking records, and full revenue analysis are available upon request.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Josie Cline (941-266-6661)
6285 MIDNIGHT PASS RD #406, SARASOTA, FL 34242
$799,000183 Days on yellowkey MLS ID: A4670228
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1456 Built: 1981 Tax: $3,221 (2024)Community: Excelsior Beach To Bay 5Condo
Taxes:$3,221
Remarks: Welcome to this beautiful Penthouse end unit at the highly desirable Excelsior Beach to Bay community. Perfectly positioned on the Bay side, this 2 bedroom, 2.5 bath condo offers an open, airy layout enhanced by vaulted ceilings, abundant natural light, and impact windows throughout for peace of mind and energy efficiency. The living and dining areas flow seamlessly together, creating an ideal setting for entertaining or relaxing. The dining area features a mirrored accent wall, a built-in cabinet under the stairs, and another built-in at the end of the room for elegant storage and display. A wood staircase leads to the loft, a rare feature in this complex. The spacious loft includes a half bath, and 2 generous closets, offering flexibility as a guest retreat, office, or media room. The loft expands your living options beautifully. The kitchen is both functional and stylish, featuring wood cabinetry, Cambria quartz countertops, marble floors, a tray ceiling and a built-in eat-in area/desk. A window over the sink provides a charming peek of the Bay. The Primary Bedroom impresses with soaring vaulted ceilings, custom built-in furniture, and a bright, open feel, while the Primary Bath offers two separate sink areas with granite counters, built-in cabinetry, and a wall of closets-providing abundant storage and space. Pella sliding glass doors lead to the Florida room/lanai, enclosed in glass and framed by vaulted ceilings invites you to relax and enjoy tranquil views year-round. Residents of Excelsior enjoy private beach access, along with two heated pools, fitness center, tennis and pickleball courts, and clubhouse. Whether you’re seeking a full-time residence, vacation getaway, or investment opportunity, this Penthouse condo offers a rare blend of comfort, style, and location.
Listing Agent: Stacy Liljeberg (941-544-6103)
5569 CAPE LEYTE DR, SARASOTA, FL 34242
$4,495,00050 Days on yellowkey MLS ID: A4685577
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 3654 Built: 2016 Tax: $32,419 (2025)Community: Siesta IslesSingle Family
Taxes:$32,419
Remarks: LOCATION, LOCATION, LOCATION !!! One Block to the Crystal Sands of Siesta Key Beach the #1 Beach in the USA! Or spend the day on the Aqua waters with two boats on lifts out back, and 119' of frontage on the Grand Canal leading to the ICW (only one bridge with about 15’ clearance to the Gulf). Oversized 16,163 sf Lot, elevated concrete block home and spectacular pool in your view from most every room! Not just the best location, but this custom-built in 2016 West Indies style home is a fortress all on one level, including the pool, and is well above the FEMA flood zone. High and dry through the "storms of the century" in 2024. Beautiful, engineered hardwood floors, custom cabinetry throughout by Elite Woodworking in the Kitchen, all Bathrooms and Great Room. The entire house has been freshly painted inside & out. Three large en-suite bedrooms. Additional rooms currently utilized as office with Murphy Bed as well as very large Bonus Room could be utilized as additional bedrooms #4 & 5, if desired. Even the powder bath has a shower for guest convenience. Large walls of sliding glass doors in all waterfront rooms extend living spaces to a huge, screened Lanai which adds over 500 sf to living space under roof, and much more in the screened Lanai area.. All hurricane rated extra heavy duty PGT doors and windows. The total A/C space is 3,654 sf, with a overall total of 5,075 under roof. The oversized 3-car garage with an Epoxy floor has a very high ceiling which allows 2 more cars to be added on lifts for a total of 5 vehicles for the enthusiast. Isonene insulated and floored attic storage space is available above the garage. New in the past year: A/C Condenser & Air Handler system in 1 (of 2) zones, water heater, refrigerator, ice maker, boat lift control boxes on both Lifts. The large free form pool and spa have new (wifi) Pentair pool pump & heater & auto chlorinator. Both boats as well as professional decorator staged furniture, decor and pictures may be available for separate purchase for "Turn-Key" possession. DEFINITELY check out the Virtual Tour, since it provides “3D walk through any direction” photos which can really give you the flow of the house as you manipulate your way around.
Listing Agent: Steve Hagan (941-900-4126)
4822 OCEAN BLVD #2A, SARASOTA, FL 34242
$839,000197 Days on yellowkey MLS ID: A4668724
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1435 Built: 1973 Tax: $7,588 (2023)Community: Siesta TowersCondo
Taxes:$7,588
Tax Year: 2023
Remarks: Price Improvement! Your Coastal Paradise Awaits! Step into a world of elegance and tranquility in this stunning condominium, perfectly situated along the breathtaking coastline of Siesta Key. Featuring two lavish ensuite bedrooms, this residence offers you the ultimate in coastal living. The primary bedroom boasts full panoramic views of the crystal blue waters of the Gulf, complete with a beautifully remodeled bathroom and an expansive walk-in closet designed for the modern lifestyle. Embrace a split floor plan that promotes privacy and relaxation, all within a breezy coastal open-concept design that floods the space with an abundance of natural light. Indulge in the outdoors from two covered balconies, ideal for outdoor dining or savoring a glass of rosé as you watch the sun dip below the horizon in a stunning display of colors. Enter the building through a well-appointed lobby that exudes sophistication and class. Residents enjoy a host of resort-style amenities that include a beautifully remodeled community center for exclusive use, a newly refurbished workout facility, and a gulf-front pool to soak in the sun. The outdoor BBQ area is perfect for gathering with friends and family, while storage for beach accessories and bikes adds to the convenience of a coastal lifestyle. Enjoy the peace of mind that comes with covered parking. Perfectly located, this luxury community allows you to walk, bike, or cruise your golf cart to local restaurants, boutique shopping, live music venues, and the vibrant farmers market, all within minutes from your doorstep. Of course, the soft, white sands of Siesta Key Beach are just a short stroll away, ready to fulfill your beach daydreams. Don't miss your chance to experience luxury coastal living at its finest. Schedule your private tour today and discover your new home in paradise!
Listing is courtesy of: ASCENDIA REAL ESTATE (941-306-4242)
Listing Agent: Beth Dilley (941-400-1322)
9011 MIDNIGHT PASS RD #426, SARASOTA, FL 34242
$569,000197 Days on yellowkey MLS ID: A4668084
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1093 Built: 1974 Tax: $5,686 (2024)Community: Sunrise Cove Sec 4Condo
Taxes:$5,686
Remarks: Location! Location! Location! Great Investment Property, Rent 12 times a year with a 30 day minimum and an onsite management company! Experience true waterfront living with spectacular views all day long of the Intracoastal Waterway from your Condo and breathtaking sunrises every morning! The grounds are absolutely Stunning! This TURNKEY furnished 2-bedroom, 2-bath condo on the 4th floor of Sunrise Cove offers comfort, style, and convenience. The spacious living room features beautiful Hard wood floors and sliding glass doors that open to a screened-in lanai with remote-controlled blinds, and a spectacular views of the Intercoastal Waterway perfect for relaxing and enjoying the panoramic views. The primary bedroom included Hardwood flooring a walk-in closet, and an en-suite bath with a large walk-in shower. The second bedroom also features wood floors, a walk-in closet, and views of the Gulf of Mexico and beach across the street. The hall bath offers a walk-in shower and tile flooring. The kitchen opens to the dining and living areas, creating an inviting open-concept layout ideal for entertaining. Additional updates include a brand-new air conditioning unit (2025) and new water heater (2025) and Brand new Roof (2025) Community Highlights: Two heated swimming pools, including an Olympic-size pool with restrooms and a covered lounge area Pickleball and tennis courts State-of-the-art fitness center and game room On-site management with 30-day minimum rentals, offering great income potential Turtle Beach is just across the street, and the free Siesta Key Breeze trolley stops nearby every 15 minutes Two popular waterfront restaurants, Turtles on the Bay and Ophelia’s on the Bay, are right next door Extra storage closet conveniently located near the elevators in the laundry room Recent community updates: new roofs, new docks, and nearly completed new carports Enjoy the best of Siesta Key living—whether as a vacation home, income-producing property, or full-time residence, this fabulous waterfront condo offers it all!
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Sheryl O'Keefe (941-376-2112)
5560 SHADOW LAWN DR, SARASOTA, FL 34242
$1,549,000464 Days on yellowkey MLS ID: A4636955
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 2124 Built: 1970Monthly Fee: $17 Tax: $8,052 (2025)Community: Siesta IslesSingle Family
Taxes:$8,052
Remarks: Siesta Key Waterfront Living—Priced to Embrace the Island Lifestyle An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this beautifully maintained residence is ideally positioned just moments from the powdery white sands of Siesta Beach and the turquoise waters of the Gulf. Set on an oversized 14,000-square-foot corner lot, this four-bedroom, three-bath home blends comfortable coastal living with everyday functionality in a highly desirable island setting. Designed for effortless entertaining and easy living, the open-concept floor plan centers around a spacious island kitchen with generous seating, breakfast bar, and abundant workspace—flowing seamlessly into the dining and living areas for gatherings both large and small. A thoughtful split-bedroom layout offers privacy for owners and guests alike. The primary suite enjoys peaceful views of the pool and canal, while a secondary bath doubles conveniently as a pool bath—ideal for indoor-outdoor living. Step outside to the covered, screened lanai and unwind beside the sparkling pool, framed by tranquil water views and gentle coastal breezes. Tucked along a quiet harbor just off the Grand Canal, the setting is ideal for kayaking, paddleboarding, or boating, with frequent sightings of manatees and coastal birds adding to the natural charm. Evenings bring glowing “mango sunsets” nearby, while mornings begin with soft sunrises reflected on the water. Additional highlights include an oversized two-car garage and a durable concrete tile roof. Ideally located near the shops, dining, and energy of Siesta Village—and just 15 minutes from downtown Sarasota’s vibrant arts and cultural scene—this home presents a compelling opportunity to enjoy the best of island living, whether as a full-time residence or a serene coastal retreat.
4050 HIGEL AVE, SARASOTA, FL 34242
$25,000,000114 Days on yellowkey MLS ID: A4677328
0 Days Off yellowkey (back on 3/28/2026)
Bed: 5 Bath: 6.5 Liv Area Sq Ft: 6301 Built: 2027 Tax: $41,628 (2025)Community: Siesta Rev OfSingle Family
Taxes:$41,628
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. One or more photos was virtually staged. An unmatched LUXURY BEACH estate, this Gulf-front upcoming masterpiece offers sweeping ocean views and a private stretch of sand on Siesta Key. Currently in development for New Construction by Pham Development, the iconic Mid-Century Modern style residence is privately gated and designed to deliver resort-level living on one of Florida’s most coveted coastlines on the Gulf of America and Sarasota Bay. Spanning 14,543 sq. ft. under roof, with 6,301 sq. ft. of air-conditioned interiors, the home features 5 bedrooms, 6 full baths, and 1 half baths. Engineered for longevity, it rests on a fortified foundation with a riprap seawall installation, ensuring enduring protection for the estate, luxe pool with hot tub, and land. Lifestyle amenities rival the finest resorts: a rooftop with ocean views, and a full personal fitness center with yoga studio. Entertainment spaces abound with opportunity for a movie theater room, an ocean-view office, gun and jewelry safe room, and an up to 16-car enclosed garage. Paddleboard and kayak access lead directly to the Gulf, with options for a beach volleyball or pickleball court. The grand master suite has an expansive Gulf-facing terrace, his-and-hers walk-in closets, and spa-inspired baths. Multiple terraces, an outdoor kitchen, a chef’s kitchen, and butler’s pantry add to the all-inclusive luxury lifestyle of this home. More than a residence, this estate is a legacy home—crafted for generations, with an indoor-outdoor footprint tailored for both grand entertaining and intimate coastal living. Private showings are available upon request.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
5151 SAINT ALBANS AVE, SARASOTA, FL 34242
$1,095,000213 Days on yellowkey MLS ID: A4666929
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2314 Built: 1963 Tax: $8,056 (2025)Community: Siesta BeachSingle Family
Taxes:$8,056
Remarks: Charming Coastal Oasis in the Heart of Siesta Key Nestled on a serene, tree-lined property, this inviting 4-bedroom, 3.5-bath beach-style home offers the perfect blend of tranquility, charm, and central location. Step into a spacious, light-filled living area with an open kitchen layout—ideal for hosting friends and making family memories. Freshly updated with new paint, gleaming quartz countertops, and stainless steel appliances, this move-in-ready home is designed for easy, coastal living. The open floor plan includes a spacious upstairs primary suite with French doors leading to a private balcony—your own quiet retreat. Three additional guest bedrooms are thoughtfully located on the first floor, including a separate guest suite with its own private entrance, offering comfort and flexibility. Step outside into your private backyard oasis featuring a beautiful pool and spa, fully enclosed with a lovely paver deck—perfect for relaxing, entertaining, or enjoying sunny Florida days in peace and privacy. There's still plenty of yard space to garden or play. Slip on your sandals for a short stroll to the world-famous Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor, or bike to the charming Siesta Key Village with its eclectic mix of shops, restaurants, and entertainment. Don’t miss this peaceful, spacious retreat—your own slice of paradise on Siesta Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
113 WHISPERING SANDS DR #V47, SARASOTA, FL 34242
$615,00064 Days on yellowkey MLS ID: A4683156
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1344 Built: 1968Monthly Fee: $1,351 Tax: $5,993 (2025)Community: Whispering Sands Sec 5Villa
Taxes:$5,993
Remarks: One or more photo(s) has been virtually staged. NEW PRICE! Discover the ease of island living in this newly REMODELED 3BR/2BA villa with garage in the premier GULF FRONT property of Whispering Sands! As a rare freestanding villa, this residence offers the privacy of no shared walls and lives like a single family residence. Every detail has been thoughtfully curated, from the reimagined open galley kitchen with its sophisticated soft grey tones and granite countertops, stainless appliances, and soft close cabinetry and drawers – flowing seamlessly into the main living areas – to the beautifully updated bathrooms and elegant tile flooring. Textured ceilings and recessed lighting create a warm, contemporary ambience. The small private patio invites relaxed al fresco dining, while the rare 1-car garage—complete with an epoxy floor, full sized W/D hookup, and its own A/C system—adds exceptional convenience and storage. Behind the scenes, extensive upgrades provide total peace of mind. All windows and sliders are 2022 hurricane impact rated. The plumbing supply and drain lines in this villa were updated from cast iron to PVC in 2022. Further enhancing the home’s value are a NEW concrete tile villa roof and a 2023/2024 garage roof. 2022 HVAC system. Ideally located just steps from the clubhouse, 2 heated pools, and 800’ of Whispering Sands’ own PRIVATE beach on the Gulf, this residence also enjoys a prime setting next to the dining, shopping, and vibrant atmosphere of Siesta Key Village. Imagine starting your day with a morning dip in the Gulf followed by a peaceful stroll along the private shoreline. Spend the afternoon unwinding poolside or swimming invigorating laps in one of two heated pools. Stroll to the Village for a delicious, cozy supper and end the day gathered with friends as the Gulf sky ignites in breathtaking sunset color. Whether you’re seeking a full-time residence or the perfect coastal retreat, this move-in-ready villa offers the best of maintenance free, resort style living in an exceptional island location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
5961 MIDNIGHT PASS RD #319, SARASOTA, FL 34242
$685,000281 Days on yellowkey MLS ID: A4659759
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1000 Built: 1974 Tax: $6,449 (2024)Community: Palm Bay Club IiCondo
Taxes:$6,449
Remarks: Looking for the perfect balance of location, lifestyle and income potential? This one delivers all three. Welcome to your slice of paradise on world-renowned Siesta Key! This spacious 2-bedroom, 2-bath condo is located in the highly sought-after Palm Bay Club, offering the perfect blend of coastal living and resort-style amenities. Located on the second floor, step inside to an open-concept living and dining area filled with natural light. A bright, white kitchen with updated recessed lighting has a smart pass through, so your culinary creations flow to the dining room as easily as your conversation. The dining area, with seating for 6, as well as the living room are turnkey furnished with attractive, neutral décor. Large windows and hurricane rated sliding glass doors lead to a private balcony, creating a seamless indoor-outdoor flow that’s perfect for enjoying the saltwater breeze. Both bedrooms are generously sized, with the primary suite offering an en-suite bath and walk-in closet. The second bedroom is equally comfortable and en-suite as well, making it perfect for guests or family with plenty of privacy for all. The Palm Bay Club is a beach-to-bay community that boasts top-tier amenities, including two heated pools, tennis courts, a fitness center, and private access to the powdery white sands of Crescent Beach. Boat docks, fishing areas, and a bayside barbecue pavilion complete the resort-like experience. This condo offers the ultimate in beachside convenience—minutes from Siesta Key Village, shopping, dining, and entertainment. With its unbeatable location and flexible rental policy, it’s a fantastic opportunity for both personal use and income potential. Don’t miss your chance to own a piece of the Siesta Key lifestyle at The Palm Bay Club. This condo is ready for you to make it your own coastal escape!
Listing Agent: Rudy Dudon (941-234-3991)
605 AVENIDA DE MAYO, SARASOTA, FL 34242
$2,195,00083 Days on yellowkey MLS ID: A4681389
0 Days Off yellowkey (back on 3/26/2026)
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 4210 Built: 2003Community: Sarasota BeachSingle Family
Taxes:
Tax Year:
Remarks: Under contract-accepting backup offers. Live the Siesta Key lifestyle at its best in this exceptional, elevated waterfront residence, positioned just one block from Siesta Village and only three blocks to Sunset Pier and world-famous white quartz sands and aqua waters of Siesta Beach. Whether you’re seeking a primary residence, vacation retreat or potential income-producing investment, this home offers the location, boating access and peace of mind today’s buyers value most. Custom-designed and built by the engineer-owner, this striking Key West–inspired, three-story home offers approximately 4,210 square feet of air-conditioned living space, thoughtfully engineered for energy efficiency, durability and low maintenance. The main living level begins at approximately 19 feet above base flood elevation, a significant advantage that helps reduce flood risk and insurance costs. Built in compliance with FEMA and Florida building codes, the home earned Florida Power & Light’s Build Smart designation, verified to be 40% more energy-efficient than required by Florida energy standards. Designed for everyday living and entertaining, the expansive open-concept main level features soaring tray ceilings, glass block accents, porcelain tile with marble inlays and abundant natural light. The chef’s kitchen offers extensive custom cabinetry, abundant quartz countertop workspace, an oversized island and stainless-steel appliances, seamlessly flowing into an expansive formal dining room ideal for hosting family and friends. The home offers five bedrooms and five baths, including a spacious owner’s suite with vaulted ceilings, spa-style bath and an oversized bonus room opening to multiple balconies with tranquil water views. A large recreation room, workshop, and generous storage add flexibility for full-time living or guest accommodations. Additional features include impact windows, wind-rated low-maintenance exterior siding, zoned HVAC with UV filtration, central vacuum, oversized four-car garage, additional driveway parking and landscaped, maintenance-free grounds. Outdoor living is a highlight, featuring a saltwater pool with titanium heat pump and hydraulic cover, expansive paver deck, outdoor kitchen with a seven-foot stainless steel grill, wet bar, pergola, gazebo and ambient LED lighting, ideal for relaxed island entertaining. Boaters will appreciate the canal-front setting with a 7,000-pound boat lift, providing easy access to Sarasota Bay and downtown by water. From morning experiences along the shoreline to breathtaking sunsets over the Gulf, every day on Siesta Key feels like a vacation. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including the Ringling Museum, Van Wezel Performing Arts Hall, St. Armands Circle and ever-popular Sarasota Farmers Market. Offering exceptional value as one of the lowest price-per-square-foot elevated waterfront homes on Siesta Key, this residence combines location, construction quality, efficiency and lifestyle, an outstanding opportunity to own in the heart of Siesta Key.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
8767 MIDNIGHT PASS RD #403F, SARASOTA, FL 34242
$590,000160 Days on yellowkey MLS ID: A4673053
1 Days Off yellowkey (back on 3/26/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1303 Built: 1979Community: Island Reef Ii Ph 1 2 & 3Condo
Remarks: Under contract-accepting backup offers. Rare Gulf-to-Bay community with a large private Gulf beach and Bay-side boat docks where owners may install boat lifts in their slips. The community is financially sound with NO assessments, making this a worry-free coastal investment. Move-in ready. Turnkey furnished. What truly sets Island Reef apart is income potential: 1-month rentals are allowed—a rare policy on Siesta Key. That means you can enjoy your own slice of paradise and still generate excellent rental income when you’re not in residence. This flexibility makes the condo ideal for both personal use and a smart, self-funding getaway. This high-and-dry 4th-floor unit is beautifully renovated, offered furnished, and move-in ready. Natural light is a standout feature—sunshine pours through the screened/enclosed balcony from morning through mid-day, filling the living areas with a bright, breezy coastal feel. Enjoy peaceful views of Little Sarasota Bay and the Intracoastal Waterway from your enclosed lanai with sliding windows—perfect for coffee, cocktails, and quiet sunsets. The modern kitchen features granite countertops, crisp white cabinetry, and an integrated washer/dryer. The spacious owner’s suite includes a large walk-in closet, while the guest bedroom offers an extra-large closet plus a separate owner’s lock-away closet for personal items when guests arrive. Island Reef lives like a resort: two heated pools, tennis and pickleball courts, fitness center, clubhouse, grilling patios, shuffleboard, game room, library, and an active social calendar. You’re a short walk to restaurants, a full-service marina with rentals and storage, and Turtle Beach. And the free Siesta Key trolley stops right in front of the community, taking you to Siesta Village, shopping, dining, and more beaches along Midnight Pass Road. Beach-to-Bay lifestyle + rare 1-month rental flexibility = a standout Siesta Key value. Schedule your private showing today.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: John Brink (941-928-5555)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.