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$465,000
1 Beds ⋅ 1 Baths ⋅ Gulf Holiday Apts SubDv. ⋅ 34242 Zip Code
Welcome to Gulf Holiday Condominium—an exceptional opportunity to own one of just 18 units in this rarely available community. This beautiful and recently updated first-floor, 1-bedroom, 1-bath residence places you just steps from the best of what Sarasota has to offer. Inside, you’ll find stainless steel appliances, quartz countertops, plantation shutters and modern finishes throughout, creating a bright and inviting retreat ideal for personal enjoyment or vacation rental income. If rental income is a priority, you’ll appreciate that this area allows for one-week rentals—a rarity in the surrounding communities. Gulf Holiday Condominium boasts an unbeatable location with effortless access to the white quartz sands of Siesta Key Beach and the vibrant shops, dining, and entertainment of Siesta Key Village. Opportunities like this are truly seldom available—don’t miss your chance to own a piece of paradise and proudly tell your family and friends, “I live where you vacation!

73 Avenida Messina Unit 6, Sarasota
$869,000
2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code
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.

6300 Midnight Pass Road Unit 21, Sarasota
$599,000
2 Beds ⋅ 2 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Welcome to your slice of paradise at Jamaica Royale on world famous Siesta Key Beach. This completely remodeled 2 bedroom, 2 bath condo offers the perfect blend of coastal elegance and income producing potential. The stunning kitchen features quartz countertops, custom wood cabinetry, stainless steel appliances, dining space, and a laundry closet with stackable washer and dryer, ideal for entertaining after a day on the sand. Both bathrooms have been beautifully updated with designer finishes, including marble like tile shower and sleek quartz-top vanities, creating a spa like retreat. The thoughtfully designed floor plan is comfortable, stylish, and Turn-key move-in ready. Located in a highly desirable beachfront community with one week minimum rentals, this condo is an excellent investment or vacation getaway. Enjoy a heated pool and approximately 300 ft of private beach frontage, just steps from the Gulf’s crystal clear waters and powder soft sand. Ideally situated near Siesta Key Village, you’re moments from renowned dining, boutique shopping, and vibrant night life. Whether you are seeking a personal retreat, rental income, or both, this is coastal living at it’s best!

5830 Midnight Pass Road Unit 107, Sarasota
$995,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Endless possibilities just two blocks from Siesta Beach! Whether you're looking to remodel the structure or build a new island retreat, opportunity awaits. A prime 12,229-square-foot property in sought-after community of Siesta Isles, just two blocks from the powdery white sands of Siesta Beach, ranked the #1 beach in the USA. This property offers a rare chance to create your dream home in one of Sarasota’s desirable beach neighborhoods. Offering a clean slate for visionary design to renovate or build new. The generous size of the property and ideal location make it ideally suited for a luxury custom home with room for a pool, tropical landscaping and seamless indoor-outdoor living. Enjoy beach access just .2 miles away, or go less than a mile to Siesta Village, where eclectic shops, lively dining and local entertainment await. 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. Unlock the potential to create a one-of-a-kind island residence just moments from world-renowned Siesta Beach.

734 Canal Road, Sarasota
$575,000
2 Beds ⋅ 2 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Siesta Key Beachfront Living at Jamaica Royale--Experience the best of coastal Florida in this fully renovated two-bedroom, two-bath condominium, perfectly situated on world-famous Siesta Key Beach. With 300 feet of private, powder-white quartz sand just steps away and no roads to cross, this Jamaica Royale residence delivers true beachfront living on a quiet, private lane. Step inside to a bright, open-concept layout featuring luxury flooring throughout. The gourmet kitchen shines with stainless steel appliances, quartz countertops, custom soft-close cabinetry, and stylish finishes. The spacious primary suite offers a serene retreat with a beautifully updated en-suite bath and walk-in shower, plus extra-deep double closets in both bedrooms for abundant storage. Recent upgrades include a new roof (2022), new water heater, new A/C, new appliances, updated plumbing, contemporary interior doors, and hardware—everything has been thoughtfully refreshed for move-in-ready comfort. Enjoy your morning coffee on the private patio, take advantage of convenient in-unit laundry, and park right outside your door. Resort-style amenities include three heated pools, plenty of lounge chairs, and lush tropical landscaping. Whether you’re relaxing to the rhythm of the Sunday drum circle, watching breathtaking sunsets, strolling the cool-to-the-touch white sand, or hopping on the free shuttle to Siesta Key Village for dining and shopping—this is relaxed, turnkey beach living at its finest.

5830 Midnight Pass Road Unit 94, Sarasota
$1,000,000
2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code
RARELY AVAILABLE! Crystal Sands, Gulf Side GROUND FLOOR UNIT! Just out the door of your lanai and it is just steps to the pool and crystal white sands of Siesta Beach! This 2 bedroom, 2 bath split plan offers the best in beachside living. Beautiful, newly remodeled kitchen with extended peninsula is perfect for prep and entertaining! New appliances as well. Bathrooms are both nicely appointed with updated fixtures. Primary bath features separate dressing area/vanity and new shower with glass enclosure. Both bedrooms have walk in closets plus an additional double closet in the guest bedroom for extra storage or a perfect owner's closet. In addition, there is a large utility room with your own washer and dryer that allows even more storage. The generous lanai is accessible from the living and both bedrooms. Enjoy a peek-a-boo view of the gulf while enjoying your favorite beverage! Crystal Sands is one of the most desirable communities on Siesta Key and a highly sought rental destination. (2 week minimum) Situated perfectly right in the heart of Crescent Beach! There are 2 heated pools, assigned covered parking, community grills and an onsite management office. Gated access for extra security and comfort. Now is your opportunity to own a unit in this famous building at a great price! Rentals in place. Please contact agent for showing availability. All information believed to be accurate but should be verified by buyer.

6300 Midnight Pass Road Unit 110, Sarasota
$3,330,000
4 Beds ⋅ 4 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
This is the renovation you would do for yourself…. If you’ve toured new construction homes recently and thought to yourself, did the architects just give up? Then this home might just be for you… *Elegance. Charm. Attention to detail.* Three phrases we don’t hear enough anymore, but that changes today as we step inside ‘Casa Alegre’ on Featherbed Lane. Located in the heart of Siesta Key Village and positioned at one of the most impressive intersections of waterways the Grand Canal offers, there is no more sought-after location on all of Siesta Key than right here. An 8-minute walk into the Village merges proximity with privacy in the exact way you’ve been imagining. This fully renovated Mediterranean Revival is overflowing with pride of ownership. Featuring major upgrades including a new roof, new seawall, all new hurricane windows and doors, new flooring, new electrical, and more; this is the renovation you would do for yourself, and that translates into true confidence, not just fresh finishes. Inside, the home lives bright and open, in part from its southern facing pool, and even more-so with volumes of natural light pouring in through NINE sets of brand-new sliding glass doors and a layout designed for effortless island living and entertaining. With 4 true bedrooms, 4 baths, plus an incredible bonus room ready for a billiards table or game room, a heated pool and boating lifestyle at your doorstep, this is a rare opportunity to own a home with genuine character, in a location that simply can’t be replicated. Private showings available upon request.

4833 Featherbed Lane, Sarasota
$1,224,000
3 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Virtually Staged. Welcome to this beautifully renovated ranch-style home, ideally located within minutes to the #1 beach in the United States—Siesta Key Beach! Set on an oversized lot, this property offers a private outdoor oasis with a relaxing pool surrounded by lush, mature landscaping, perfect for entertaining or unwinding after a day at the beach. Designed for effortless single-level living, this home blends modern updates with timeless coastal style, making it perfect as a full-time residence, vacation getaway, or investment opportunity. Offering 3 spacious bedrooms + den and 2.5 updated baths, the thoughtfully designed floor plan delivers both comfort and functionality. Light-filled living areas flow seamlessly throughout the home, complemented by a stylishly updated kitchen and baths featuring quality finishes. A detached garage adds valuable convenience and storage. Recent upgrades include a 2024 Tesla solar system with two Powerwall's, providing energy efficiency, backup power, and long-term savings. Additional improvements include two HVAC systems for optimal climate control and a new water heater for added peace of mind. Enjoy morning strolls to the world-renowned quartz sands of Siesta Key Beach, evenings dining at Siesta Village, and the ease of move-in-ready coastal living in one of the most sought-after locations. Expertly restored terrazzo flooring throughout the main living areas and bedrooms, giving the home a new fresh look. All information should be independently verified by buyer's and buyers agent.

5107 Saint Albans Avenue, Sarasota
$875,000
2 Beds ⋅ 2 Baths ⋅ Crescent Royale SubDv. ⋅ 34242 Zip Code
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757 Beach Road Unit 300, Sarasota
$592,500
2 Beds ⋅ 2 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code
Welcome to your Siesta Key Beach escape at 6006 Midnight Pass Rd, Unit 44! This charming, fully furnished 2-bedroom condo places you steps from the world-famous powdery white sands and turquoise waters of Siesta Key Beach. Enjoy direct private beach access, breathtaking Gulf views, and endless sunsets right from this coveted coastal community. Inside, an open and inviting layout features vaulted ceilings with exposed wood beams, a spacious living room with plush sectional seating, and a bright dining area perfect for gatherings. The well-appointed bedrooms offer comfortable accommodations—one with fun bunk beds ideal for families or guests, and a serene primary with a king bed. Community amenities elevate the lifestyle: two large heated pools surrounded by palm trees, shuffle board court, tennis court as well as a pickleball court, making this a prime beachfront location. Turnkey and rental-ready this property has proven rental appeal with weekly rentals allowed and is ideal as a vacation retreat, investment opportunity, or full-time residence. The open-concept kitchen and living area was redesigned in 2023 with the removal of a dividing wall, creating a bright and welcoming space ideal for everyday living and entertaining. The kitchen features quartz countertops, custom Showplace cabinetry, updated appliances, and durable luxury vinyl plank flooring that continues throughout the unit. Major system upgrades include fully updated plumbing with PVC sanitary piping and CPVC water lines, along with extensive electrical improvements completed in 2025, including a new 125-amp main disconnect, surge protection, arc-fault breakers, and code-compliant wiring. Impact-rated windows and doors with insulated Low-E glass were installed in 2025, enhancing safety, energy efficiency, and storm protection. Both bathrooms have been updated with custom cabinetry and quartz countertops, and a convenient half bath was added to the primary bedroom. Additional highlights include custom closet systems, a newer Bryant heat pump condenser, and a rare, grandfathered-in ventless washer/dryer unit.

6006 Midnight Pass Road Unit 44, Sarasota
$1,305,000
4 Beds ⋅ 4 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
EXCEPTIONALLY RARE Siesta Key Income Property | Zoned for DAILY Rentals — a true Siesta Key Unicorn. This rare 4-bedroom, 4-bath duplex offers a unique opportunity to acquire a short-term rental asset just a short stroll from the world-famous white sands of Siesta Key Beach, one of the most supply-constrained and consistently in-demand vacation markets in Florida. Configured as two fully renovated 2BR/2BA residences, this property delivers unmatched flexibility—ideal as a high-performing investment, 1031 replacement property, vacation home, or personal residence with income potential. Zoned for DAILY rentals—a highly limited and valuable designation on Siesta Key—the property is currently operated as a professionally managed short-term rental with future bookings in place. Designed for both guest appeal and operational efficiency, each unit features open-concept living spaces, updated kitchens, in-unit laundry, durable tile flooring throughout, and tasteful coastal furnishings. The property is being sold fully furnished and turnkey, allowing for a seamless transition of ownership with no operational downtime. Outdoor amenities further support strong occupancy and repeat bookings, including a fenced, heated pool, tropical landscaping, lounging and dining areas, and a private grilling space. Four dedicated off-street parking spaces (two per unit) add a meaningful competitive advantage in this highly desirable beach location. Professionally operated as a vacation rental since 2020, the property has achieved documented gross rental income approaching $200,000 annually. A temporary decline in late 2024 and early 2025 was event-driven rather than demand-driven, due to regional hurricane-related cancellations. Travel demand to Siesta Key is now rebounding, and bookings are steadily returning—positioning the property for revenue normalization and potential growth consistent with prior peak years. Whether you are a short-term rental investor, 1031 exchange buyer, or an owner seeking to blend lifestyle with income, this property offers a rare combination of location, zoning, resilience, and upside in one of Florida’s most desirable coastal markets. Detailed income and expense reports available upon request. Buyer to verify exchange eligibility and tax treatment with qualified advisors. Private showings by appointment only.

1123 Crescent Street Unit 1123/1125, Sarasota
$799,999
2 Beds ⋅ 2 Baths ⋅ Provintial Gardens SubDv. ⋅ 34242 Zip Code
DEEDED SIESTA BEACH ACCESS! Perfect Snowbird Getaway! Mid Siesta Key, highly sought after, free-standing villa with it’s own private courtyard front, side and rear. Maintenance Free condo lifestyle that feels like a single family home. Situated in Provincial Gardens on a lushly landscaped and tree canopied street of only 26 units offering old Florida charm. This updated, Turnkey Furnished 2 bedroom + Den, 2 bath offers 1400sf. Spacious owner’s suite features a private patio; wall of closets; and ensuite bath. The updated kitchen offers abundance of cabinets and counterspace & newer appliances. The open floor plan offers tile floors throughout; abundance of sliding glass doors opening to your surrounding private courtyard; Florida room; updated baths; Full Size washer/dryer utility closet; new hot water heater 2023; New roof 2023; & Storage Shed 10x6. The crown jewel of this community is the enormous Bay front park with spacious paver patio where owners and their guests enjoy exquisite sunrises and picturesque sunsets while watching the dolphins, manatees, birds and boaters play in the intracoastal waterway. In addition, there is a new seawall, day dock with canoe/kayak launch, and plenty of room to try your luck at fishing. In addition, owners enjoy Deeded Beach Access; beach chair usage; and jr. Olympic heated pool across the street at the Aloha Kai Community. It is also comforting to note that this community sustained no water damage from any recent hurricanes. This Beach to Bay Retreat is ready as a rental or personal winter getaway for you, your family and friends. This mid-key location is an easy Breeze Bus or Froggy Hop ride to Siesta Key Village; Tennis Courts; Public Beach; Grocery; and abundance of restaurants. Don't delay; these units are rarely available and sell fast.

6005 Midnight Pass Road Unit N4, Sarasota
$850,000
2 Beds ⋅ 2 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code
Sandy Cove – Mid-Century Modern Gulf Front Paradise: Period-preserved mid-century architecture meets breathtaking Gulf front water views in this exceptional Siesta Key residence. Located in Sandy Cove, a hidden gem and distinguished 1970s development of villas and mid-rises, this fifth-floor residence offers a panoramic vista over Big Pass to Lido, Bird Key, and downtown Sarasota—a guaranteed "wow" moment. Sandy Cove Condos was designed in 1969 by Frank Folsom Smith with James Holliday and James Durden, earning a 1970 AIA Florida Award for architectural excellence. This light-filled, architecturally preserved residence is over 1,200 square feet with two bedrooms, two bathrooms, and a thoughtful split floor plan. Upon arrival, you're greeted by a charming garden courtyard that offers a glimpse into the home. Step inside and be captivated by the spectacular living room featuring soaring vaulted ceilings that provide ample natural light and an airy, open ambiance. Enjoy breathtaking Gulf water views from your living room and kitchen sliders, which open seamlessly to your private patio. The sliders pull back to welcome Gulf breezes throughout the entire residence, connecting to several delightful porches and patios—including an additional private palm tree patio with IPE decking. A rare and highly coveted feature: this residence includes a private one-car garage. Gulf front residences in Sandy Cove rarely become available, making this a unique chance to own a piece of Siesta Key's architectural history. The home has potential to be sold furnished and is offered in as-is condition, presenting an opportunity for buyers to customize their personal vision. Ideally situated close to Siesta Key Village—just a short distance away, this truly unique location offers a natural private beach exclusive to the community, along with a fishing pier. Come see this truly "if you know, you know" treasure on Siesta Key.

35 Sandy Cove Road Unit 2A, Sarasota
$1,350,000
4 Beds ⋅ 4 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code
Experience the epitome of luxury with this stunning home that defines coastal elegance. Nestled on a quiet island street, this Florida Coastal masterpiece is set on a large 12,805 square foot lot with 75 ft of private lakefront overlooking the serene waters of Lake Norma, on our famed Siesta Key. Renovated with meticulous attention to detail, this newly updated home features an expansive, light-filled open floor plan with continuous quartzite countertops throughout. It includes two primary suites, one of which flows into its own private kitchenette overlooking the tranquil waterfront. Two lanais and a custom built hot tub and pool complete with a waterfall and color-changing lighting system ensure seamless indoor-outdoor living. Quality and craftsmanship are paramount, and every detail has been thoughtfully considered to ensure superior structural integrity, including the hurricane impact windows and elevated AC condensers. A new roof was installed in 2024, along with new mechanicals, electrical, plumbing, pool surfacing, appliances, and more. This gorgeous island paradise has been fully renovated to both preserve and highlight its architectural elegance. A prime location, this property is ideally situated minutes to the world-famous powdery sands of Siesta Key Beach, less than a mile from charming Siesta Key Village, and near the prestigious Out-of-Door Academy. A quick 5-minute drive over the North Bridge takes you to Sarasota proper and a mere 10 minutes more to the heart of dazzling downtown Sarasota and St. Armands Circle, where you can enjoy a wide selection of fine dining, shopping, and world-class cultural arts and nightlife, making it the ideal home for those seeking the ultimate Florida lifestyle. Schedule your private showing today.

4646 Gleason Avenue, Sarasota
$429,000
1 Beds ⋅ 1 Baths ⋅ Polynesian Gardens SubDv. ⋅ 34242 Zip Code
Totally renovated and updated villa with one bedroom and one full bath plus a bonus room and a large glassed-in lanai. This property is located in beautiful Polynesian Gardens close to the community pool and clubhouse. Extra-large great room and primary bedroom. Bonus room large enough for a queen size bed. Extra-large glassed-in lanai. New appliances, new kitchen cabinets, new tile floors throughout. Impact glass in entry door, PGT impact windows and plantation shutters. Too many improvements to list. List of improvements available. The free Siesta Breeze trolley stops in front of the main entrance providing quick access to the #1 Beach at Siesta Key plus Siesta Village, South Siesta Village and Turtle Beach. Fishing pier also available on Intracoastal.

1214 Moonmist Circle Unit S-01S, Sarasota
$475,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Welcome to affordable GULF FRONT living! This is currently the best priced 2 bedroom/2 bath condo on the Gulf side of Siesta Key! The seller is also willing to offer a rare, $60,000 SELLER CREDIT with an acceptable offer to offset any future improvements or assessments. This recently updated DOUBLE LANAI CORNER unit is nestled in the southwest corner of the popular Tropic View building, the Whispering Sands midrise closest to the Gulf and 800' of your own private beach. The freshly painted interior features NEW luxury vinyl plank flooring, NEW interior doors, and NEW overhead designer lighting and fans. Four sets of floor-to-ceiling sliders open from the living areas and bedrooms into TWO separate 24’ glassed and screened lanais – complete with epoxy flooring and NEW ceiling fans to capture the coastal breezes. After a full day at the beach, meal prep is easy in your partially open kitchen featuring NEW granite countertops, farmhouse style stainless sink, and NEW 2025 Whirlpool and GE stainless appliances. The spacious primary bedroom includes a nice walk-in closet and an ensuite bath, while the generous second bedroom comfortably accommodates up to two queen beds and boasts a full wall of closet space. Both updated bathrooms feature NEW cabinets, vanities, & fixtures, with glassed walk-in showers and recessed lighting. Brand NEW 2026 HVAC system and 2025 water heater. The unit also comes with its own assigned storage locker located just across the hall, ideal for storing all of your beach essentials. Conveniently located next door to the colorful shops and restaurants of Siesta Key Village, Whispering Sands is a premiere 55+ Gulf front property offering two heated pools, beachside Tiki Hut and gas grills, shuffleboard, canoe/kayak storage, and 800' of PRIVATE quartz sand beach. The clubhouse is currently undergoing complete remodeling. Upon completion in 2026, it will include a full catering kitchen, fitness rooms, large screen TV, and an elegant space for community wide or private social events. New landscaping plan for the building and throughout the entire 25-acre property is currently underway. Attractively priced below market, this unit represents a great investment. Don’t miss this opportunity to experience the ease of island living at Whispering Sands!

101 Whispering Sands Drive Unit 107, Sarasota
$1,022,000
4 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
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.

5151 Saint Albans Avenue, Sarasota
$1,200,000
4 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Back on the market! Beautiful triplex that went through a total renovation 2024. A re-roof project was completed in 2022 and is under a transferable warranty. Property can be rented as 3 separate units - Studio, One Bedroom, Three Bedroom. Property could easily be converted to a duplex (2 BR / 1 BA + 3 BR / 2 BA) in the event the owner prefers to live in one unit and rent the other. Just a few blocks from Siesta Village and an easy stroll to the beach, this is a great location to enjoy what Siesta Key has to offer! Total living Space - 2173 SF Main Unit - 3 BR / 2 BA - Approx - 1400 SF Second Unit - 1 BR / 1 BA - Approx. 600 SF Third Unit - Studio / 1 BR 1 BA - Approx - 200 SF Total living Space - 2173 SF Main Unit - 3 BR / 2 BA - Approx - 1400 SF Second Unit - 1 BR / 1 BA - Approx. 600 SF Third Unit - Studio / 1 BR 1 BA - Approx - 200 SF

604 Avenida De Mayo, Sarasota
$599,900
4 Beds ⋅ 4 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
An exceptional opportunity on coveted Siesta Key, this duplex property with two units is offered as-is, with flexibility to restore the existing structure or rebuild to suit your vision. Situated on an expansive lot just minutes from Shell Beach and Siesta Key Public Beach, the property offers convenient access to world-famous sand beaches, dining, and shopping. Whether you are a builder, investor, or owner looking to create a custom coastal retreat or income-producing duplex, this property presents outstanding potential in one of Florida’s most desirable island communities. All offers are welcomed and encouraged.

3615 Higel Avenue, Sarasota
$1,650,000
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Set along the Grand Canal in Siesta Isles, this inviting waterfront pool home offers an effortless blend of space, comfort and classic island living. Thoughtfully designed on a single level, the approximately 2,477-square-foot residence features a desirable three-way split floor plan with three private bedroom suites, three baths, a dedicated office or den, utility room and a two-car garage. Handsome double-entry doors open to a light-filled interior with high-volume ceilings and an easy, open flow, ideal for everyday living and entertaining. The great room connects seamlessly to the kitchen and breakfast area, all of which are positioned to capture long, tranquil canal views. A separate dining room with built-in cabinetry adds flexibility for hosting, while the kitchen is well-appointed with wood cabinetry, stone countertops, stainless steel appliances and a breakfast bar. French doors extend the living space outdoors to a large, screened paver lanai with covered seating, a pool and expansive water views, creating an indoor-outdoor lifestyle. A newer seawall, private dock with a kayak lift and a separate boat lift provide quick access to Sarasota Bay, the Intracoastal Waterway and the Gulf of Mexico, with open water within approximately 15 minutes. Ideally just minutes from Siesta Key’s world-famous quartz sand beaches, the shops and restaurants of Siesta Village, and cultural offerings of downtown Sarasota, this home delivers the best of waterfront living in one of the island’s sought-after neighborhoods. Whether as a full-time residence or a coastal retreat, this Siesta Isles property offers the lifestyle, location and boating access that define life on the water.

5348 Shadow Lawn Drive, Sarasota
$1,700,000
5 Beds ⋅ 3 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code
Welcome to an unparalleled sanctuary at 4534 Banan Place, a Siesta Key treasure that marries zen-like tranquility with the finest touches of luxury. This more-than-3,000-square-foot, five-bedroom, three-bath estate is a hidden gem, offering a spa-like retreat with dual living spaces, a flex room, and an atmosphere that feels like a private resort. Every inch has been exquisitely reimagined: a new standing seam black Key West–style roof (50-year lifespan) installed in 2025, High-impact resistant skylights, doors, and sliders, and curated lighting throughout create a luminous and serene interior. The heart of the home is a gourmet kitchen featuring top-of-the-line Café appliances, a double oven, a gourmet pot filler, and JARLIN custom soft-close cabinetry in all bathrooms, the kitchen, and the master closet. The centerpiece is an imported African walnut waterfall island, a stunning 7.5-foot by 4.5-foot masterpiece anchoring the space. The entire home is enhanced by the luxury of 22mm extra-long and extra-wide vinyl plank flooring, as well as 48x48 luxury tiles in a calming jade-like hue. Within this serene haven, you'll find not just one but a true dual ensuite layout, offering two primary suites—one larger than the other—both adorned with custom shelving throughout and luxurious five-panel doors. The main primary suite is a sanctuary of its own, complete with private access to the outdoors and pool. The primary bathroom is a spa-like escape, featuring a double glass-door shower with a rain head, wand, and expansive tile running up the wall. On the opposite side of the home, two additional guest bedrooms provide comfort and style. A brand-new tankless water heater ensures endless comfort, and the home also includes a front-load LG washer and dryer for modern convenience. Adding to the allure, the home includes a full wine bar with a brand-new wine fridge, perfect for entertaining in style. Outside, the newly resurfaced and rescreened pool area is surrounded by elegant travertine decking and mature landscaping with an ornamental irrigation system, creating a true private oasis. Two outdoor showers add to the resort-like experience. High-end renovations include: New standing seam roof; High-impact doors throughout the home; Durable Luxury Vinyl Plank flooring; African walnut waterfall countertops & custom wood ceiling in the kitchen; Floor to ceiling tile in main primary bathroom; New major appliances including, pool equipment, Café Appliances and water heater; and designer finishes and curated lighting throughout. Finally, immerse yourself in the lifestyle of Siesta Key: a world-renowned destination known for its pristine beaches, vibrant local culture, and a sense of community that is second to none. The home is ideally located just blocks from Roberts Bay and less than a mile from the award-winning crystal sands of Siesta Key Beach. With no HOA or deed restrictions, you have the freedom to make this oasis truly your own. **Notably, this property was appraised in December 2025 at $2.33 million—$330,000 above the list price—ensuring immediate equity for the fortunate new owner. Welcome to a life of unmatched elegance on Siesta Key.

4534 Banan Place, Siesta Key
$4,900,000
3 Beds ⋅ 2 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Set along one of Siesta Key’s most coveted bayfront streets, this exceptional property offers some of the most breathtaking views in all of Sarasota—spanning open water, the city skyline, and endlessly changing sunsets. Positioned in an enclave of multi-million-dollar homes, the location alone is extraordinary, with deep, open boating water and immediate access to Sarasota Bay. While the true value lies in the irreplaceable bayfront land, the home itself has been recently remodeled and exudes a charming Siesta Key cottage vibe—warm, inviting, and perfectly suited for relaxed coastal living. Thoughtful updates blend seamlessly with the home’s character, creating a space that feels both comfortable and refined. Outdoors, enjoy a private pool overlooking the water, ideal for entertaining or unwinding after a day on the bay. A two-car garage provides convenience and storage, while the property’s proximity to world-famous Siesta Beach, downtown Sarasota, and Sarasota Memorial Hospital offers unmatched lifestyle appeal. Whether envisioned as a serene waterfront retreat, a rental investment, or the future site of a custom estate, this bayfront opportunity combines remarkable views, premier boating, and one of the finest locations on Siesta Key.

843 Norsota Way, Sarasota
$1,000,000
3 Beds ⋅ 3 Baths ⋅ Sara Sands SubDv. ⋅ 34242 Zip Code
An exceptional opportunity on iconic Higel Avenue in Sarasota, where value is firmly rooted in land, location, and waterfront lifestyle. Situated on over 15,000 square feet, nearly half an acre, this property offers 92 feet of canal frontage and endless potential to renovate, expand, or build your dream coastal retreat.The existing residence features 3 bedrooms, 2 full bathrooms, and 1 half bath, providing immediate functionality while allowing flexibility for future plans. Whether envisioned as a personal residence, investment, or redevelopment opportunity, the setting alone is truly compelling.The location is unmatched. Just 0.6 miles to the vibrant Siesta Village, enjoy easy access to boutique shopping, acclaimed dining, and local nightlife. Beach lovers will appreciate being only 0.7 miles to the nearest beach access, with the main entrance to world-renowned Siesta Beach just over a mile away, celebrated for its powdery white sands and crystal-clear waters.This is more than a property. It is a rare chance to secure a premier canal-front parcel in one of Sarasota’s most desirable coastal corridors, offering a lifestyle defined by proximity to the water, the beach, and everything that makes Siesta Key extraordinary.

5036 Higel Avenue, Sarasota
$690,000
3 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
This beautifully reimagined, 3 bed/2 bath, detached freestanding villa with garage in the GULF FRONT property of Whispering Sands has been thoughtfully updated from top to bottom in 2025, offering 1,327 square feet of sophisticated, light-filled living space – blending modern style with effortless comfort. NEW 2025 villa roof. Elegant finishes include fresh interior paint, crown molding, textured ceilings, recessed lighting throughout, ceramic tile flooring in the main living areas, and newly carpeted bedrooms. At the heart of the home is a NEW open kitchen designed for both style and function, featuring granite countertops, breakfast bar, stainless Whirlpool appliances, abundant soft-close cabinetry, and pantry with convenient pull-out drawers. Recessed and under cabinet lighting complete this inviting space. NEW hurricane impact sliders in the living areas and bedrooms provide total peace of mind. A spacious brick paver patio creates an ideal setting for sunny relaxation, entertaining, or grilling under the stars. Both bathrooms have been tastefully updated with granite countertops, soft-close cabinetry, modern fixtures, lighting, and glassed walk-in showers. NEW full sized washer and dryer. Community enhancements include scheduled exterior pressure washing and villa painting in January 2026, with beautiful new landscaping to follow. FURNITURE minus a small exclusion list is included with the sale of the property.

204 Hourglass Way Unit V9, Sarasota
$1,795,000
3 Beds ⋅ 4 Baths ⋅ Sanderling Club SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Location, Privacy, Location, Value, Location. Welcome to the BEST non-Gulf front setting in Sanderling on Siesta Key. This fully updated home sits on a ¾-acre lot with an adjacent co-owned ¾-acre lot, giving you the benefit and privacy of over 1.5 acres on a private island in the middle of Sanderling. It is grandfathered to remain as a one-level home with no steps, allowing you to enjoy it indefinitely as your dream home or design and build a future residence on Plover. Set within the gates of the exclusive Sanderling Club on Siesta Key, this exceptional 3-bedroom, 3.5-bath residence presents a rare opportunity to own in one of the island’s most private and storied coastal communities. The Sanderling is a member-owned Gulf-to-Bay enclave celebrated for its low-density design, lush tropical landscape, iconic banyan canopy, and unparalleled access to Siesta Key’s world-famous quartz sand beach. Residents enjoy boat slips for lease, both clay and hard tennis courts, pickleball courts, clubhouse amenities, and guard-gated security. Beautifully positioned among mature tropical landscaping, the home blends timeless charm with high-quality upgrades and thoughtful improvements. Impact-rated windows and doors provide security, energy efficiency, and peace of mind. A brand-new roof was installed in 2025, and the home is insulated throughout with Isonene foam insulation for excellent climate control and quieter interiors. Inside, the home is warm, bright, and designed for relaxed coastal living. The main living spaces feature abundant natural light and tranquil garden views through large windows and sliders that connect seamlessly to the surrounding greenery. A rare feature for Siesta Key, the living room includes a fully functioning wood-burning fireplace, creating a cozy focal point for cooler winter evenings. The open living and dining areas offer flexible space for entertaining or everyday comfort, while the kitchen provides generous workspace, ample cabinetry, and excellent flow to the surrounding rooms. In addition to the three bedrooms, the home includes a comfortable office ideal for remote work or quiet reading, along with a large walk-in pantry providing exceptional storage and organization. The primary suite is privately situated and offers peaceful views, generous closet space, and an en-suite bath designed for comfort and functionality. Two additional guest suites, each with their own private bathrooms, provide excellent accommodations for family and visitors, while a convenient half bath serves the main living areas. Outdoor living is one of the home’s greatest attributes. Surrounded by mature landscaping and the Sanderling’s natural canopy, the grounds feel serene and secluded. A beautifully installed turf lawn creates a low-maintenance outdoor space ideal for pets, play, or lounging, while a dedicated fire pit area offers the perfect place to gather in the evenings and enjoy the soft Gulf breezes. As a resident of the Sanderling Club, you’ll enjoy access to a members-only beachfront, clubhouse amenities, tennis and pickleball courts, and boat access. The Sanderling Clubhouse renovation has been approved and is underway, further enhancing the community’s already exceptional amenities. This bright and inviting island home is truly a must see, offering an extraordinary combination of privacy, setting, and lifestyle in one of Siesta Key’s most cherished communities.

7221 Plovers Way, Sarasota
$1,305,000
4 Beds ⋅ 4 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
EXCEPTIONALLY RARE - A Siesta Key Unicorn! This 4-bedroom, 4-bath property offers the opportunity to use as a Personal Residence (perfect for multi-generation living), Vacation Home or Duplex. This property is zoned for DAILY rentals, making it ideal for AirBNB! Just a short stroll to the world-famous sugary white sands of Siesta Key Beach, this charming coastal gem is beautifully renovated, decorated in soft beach-inspired hues with comfortable furnishings, tropical décor, and easy-maintenance tile flooring throughout. Designed for both lifestyle and performance, the property is being sold fully furnished and turnkey. Outside, enjoy a fenced, heated pool area surrounded by lush tropical landscaping that creates a private oasis for relaxation. The pool area offers brand-new lounge chairs, a grilling area, and outdoor dining for six—perfect for entertaining guests or unwinding after a day at the beach. There are four assigned parking spaces directly in front, adding convenience for owners and guests alike. This property offers exceptional flexibility and appeal. It is currently being professionally managed as a duplex with future bookings in place and a strong rental history. Whether you are looking for a personal residence for multi-generational living, a place to live AND generate rental income, or a high-performing short-term rental investment, this is it! The property is currently managed by a professional local vacation rental company, making ownership seamless and low-stress. Located close to shopping, dining, trolley stops, South Siesta Key Village, and more, this is a prime location that continues to attract repeat visitors year after year. Call now to schedule a private showing of this must-see property.

1123 Crescent Street Unit 1123/1125, Sarasota
$900,000
1 Beds ⋅ 1 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code
This fully updated spacious and open condominium located on Siesta Key boasts incredible views of the Gulf of America and Siesta Key Village. Enjoy them one of your three private balconies! An abundance of bright natural light flows throughout the unit. With its private beach access, pool area, common area, and close proximity to the Siesta Key Village, this unit offers an abundance of lifestyle.

5400 Ocean Boulevard Unit 8-04, Sarasota
$1,481,696
4 Beds ⋅ 2 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code
Beach House Bungalows offers an exceptional opportunity to own a fully rebuilt, potential income-producing duplex in one of Siesta Key’s sought-after rental locations, just one block from world-famous Crescent Beach. With no minimum rental period, this property is ideally suited for short-term vacation rentals, seasonal stays or flexible personal use, making it a compelling investment in a high-demand coastal market. Completely rebuilt in June 2025, both bungalows have been thoughtfully reimagined to deliver modern comfort with a relaxed island aesthetic that today’s travelers seek. Each bungalow features two bedrooms with a king and queen bed, a queen sleeper sofa, and accommodations for up to six guests. New kitchens and baths, all new appliances, furnishings, televisions, and in-unit washer and dryer systems ensure a turnkey experience for owners and guests alike. Private outdoor showers, along with dedicated grilling and dining areas, enhance the laid-back beach lifestyle and add to the property’s strong rental appeal. Guests are drawn to the unbeatable go-to-everything location, with easy access to Crescent Beach’s powdery white sands, spectacular sunsets and soothing Gulf breezes. A nearby trolley stop provides convenient transportation throughout the island, connecting to the shops, restaurants and boutiques of Siesta Key Village. Favorite local spots are just steps away, while water sports, bike and kayak rentals, tiki bars and everyday conveniences are all within a single block. For outdoor and water enthusiasts, nearby Point of Rocks offers snorkeling, diving and fishing along the Gulf Coast’s only natural coral reef, adding another layer of adventure and allure for vacationers. With its recent total rebuild, prime location near the beach and flexible rental structure, Beach House Bungalows is a rare opportunity to own a high-performing Siesta Key investment property that captures the essence of island living, where guests arrive, unwind and happily repeat the experience again and again.

1136 Seaside Drive, Sarasota
$452,000
1 Beds ⋅ 1 Baths ⋅ Holiday Apts SubDv. ⋅ 34242 Zip Code
Welcome to Gulf Holiday Condominium—an exceptional opportunity to own one of just 18 units in this rarely available community. This beautifully updated second-floor, 1-bedroom, 1-bath residence places you just steps from the best of what Sarasota has to offer. Inside, you’ll find stainless steel appliances, quartz and granite countertops, and modern finishes throughout, creating a bright and inviting retreat ideal for personal enjoyment or vacation rental income. If rental income is a priority, you’ll appreciate that this area allows for one-week rentals—a rarity in the surrounding communities. Gulf Holiday Condominium boasts an unbeatable location with effortless access to the white quartz sands of Siesta Key Beach and the vibrant shops, dining, and entertainment of Siesta Key Village. Opportunities like this are truly seldom available—don’t miss your chance to own a piece of paradise and proudly tell your family and friends, “I live where you vacation!

73 Avenida Messina Unit 15, Sarasota
$4,000,000
4 Beds ⋅ 4 Baths ⋅ Bay Island Shores SubDv. ⋅ 34242 Zip Code
Coastal Elegance on the Northern tip of Siesta Key. Discover timeless luxury in this waterfront estate nestled in the exclusive Bay Island enclave on Siesta Key's coveted North end. With panoramic views of Roberts Bay and the Intracoastal Waterway, this home captures the essence of Florida lifestyle- elegant, relaxed and designed for seamless indoor/outdoor living. Step inside to find all new engineered hardwood flooring, a gourmet kitchen with all new top of the line appliances featuring a Sub-Zero refrigerator, Bosch dishwasher, a Jenn Air Oven/Microwave combination, a 5-burner gas cooktop, a warming drawer and all new custom-made wood cabinetry. It also has a double door pantry for all your kitchen supplies and a built-in desk for all your recipes or a workstation for the family. The rear of the home has a wall of sliders across the back which gives you expansive views out to the bay. This level has 3 bedrooms and 3 baths, two of them are bedroom suites and there is a large laundry room with new washer/dryer and a wall of shelving for any storage or folding needs. The second level encompasses your main bedroom suite and two expansive screened-in porches/lanais for incredible southern and northern views. The all-new main bath has a soaking tub, a walk-in shower all new cabinetry and a walk-in closet. Stepping outside embrace the outdoors with an open-air pool, and an outdoor shower. Boating enthusiasts will appreciate the three docks, featuring a 16,000-pound boat lift, a 10,000-pound lift for an accessory boat or jet ski, and mooring for a 35-foot boat. The property offers direct sailboat access to the Gulf of Mexico, making it a boater's paradise. The property features a complete newer seawall installed in 2018 with a new wall and cap. The northern tip offers the convenient access to the gulf and easy-on/off the island for shopping, restaurants and access to downtown Sarasota. Freeling Drive is renowned for its pristine waters. From your backyard, watch dolphins play and kayakers glide by. Catch fresh stone crabs and blue crabs right off your dock. You're just minutes away from Siesta Key Beach, Shell Beach, downtown Sarasota, shopping, and the arts.

878 Freeling Drive, Sarasota