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$450,000
1 Beds ⋅ 1 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code
This freshly updated turnkey furnished 1 bed + loft pet-friendly condo is ready for its new owner! The unit sits high and dry on the second floor and has a small loft with a queen-sized bed, a wood-burning fireplace, a main bedroom with a separate mini split AC unit, and ensuite bathroom with shower. Plenty of natural light and a large, newly refinished balcony overlooking the spring-fed lake. Updates include refinished kitchen cabinetry, quartz countertops, cooktop, moveable island with genuine butcher-block top, built-in trash and recycling cabinet, and a breakfast bar with seating for 4, and hard-wearing luxury vinyl plank floors throughout the main living/bedroom area. This unit also benefits from a brand-new standing seam metal roof. Sandy Cove is a highly sought-after old Florida-style community located just north of Siesta Key Village. Relax and enjoy the pristine white quartz sand 350 ft. stretch of private Gulf-front beach in a natural Old Florida setting. Enjoy the morning sun from your balcony. Come experience the true experience of old Florida with the Sandy Cove community, designed by the renowned Sarasota School of Architecture master Frank Folsom Smith. You will have a covered parking space with a storage closet for beach chairs and bikes, and there is kayak storage on site. Impact windows and sliders. Stack washer and dryer in unit. Just bring your beach towel and move right in!

24 Sandy Cove Road Unit A6-D, Sarasota
$1,395,000
4 Beds ⋅ 3 Baths ⋅ Bay Island Park SubDv. ⋅ 34242 Zip Code
A Rare Weekly Rental Opportunity on Siesta Key! Attention second homeowners and investors: opportunities like this are exceptionally rare on Siesta Key. Located in coveted Bay Isle, this private pool home is legally zoned for seven-day minimum rentals - a major advantage on an island where most properties require 30-day stays. The result? Strong income potential in one of America’s most in-demand vacation destinations, with average daily rental rates of $613 since 2022. Offered turnkey furnished, this three-story coastal retreat is ideal as a personal escape, income-producing vacation home, or a blend of both. Just a short golf cart ride to Siesta Key Village and the world-famous Siesta Key Beach—voted #1 in the U.S., the home is tucked behind lush, professionally landscaped tropical foliage, creating a true sense of privacy and serenity. A brick-paver driveway winds through the greenery to an oversized two-car garage, providing plenty of room for beach gear, bikes, and toys. Inside, the home is thoughtfully designed with bedrooms and bathrooms spread across three levels, offering exceptional privacy for guests and groups. The first floor addition (2011) includes a fourth bedroom, third bathroom, and sitting area—expanding the home’s capacity to comfortably accommodate up to 10 guests. The dining area flows seamlessly to a screened porch, perfect for alfresco meals surrounded by palms and tropical breezes. The entire third floor is dedicated to the owner’s suite, a private sanctuary featuring an en-suite bath and direct access to a secluded sun deck—ideal for morning coffee, sunbathing, or unwinding as the sun sets over Siesta Key. Outdoor living shines with recent upgrades, including a new putting green, expansive two-story deck with screened enclosure and paneled ceiling (2024), and a 2024 six-passenger street-legal golf cart—included. Additional improvements include a metal roof (2021), new 50-gallon water heater, and updated AC and heat pump. Whether you’re looking to generate immediate rental income, enjoy a personal island retreat, or both, this property delivers on every level. With its rare weekly rental eligibility, upscale amenities, private tropical setting, and prime Siesta Key location, this is a truly exceptional Gulf Coast opportunity.

3446 Anglin Drive, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code
If you're seeking a spacious condo on Siesta Key with incredible gulf front views, look no further. This exceptional residence is located in Sandy Cove, a hidden gem of Siesta Key and a distinguished mid-century modern development designed by locally renowned architect Frank Folsom Smith. Ideally situated close to Siesta Key Village—just a short walk away—the community features its own private beach and fishing pier. This 2-bedroom, 2-bathroom residence offers a unique and thoughtfully designed floor plan. Upon arrival, you're greeted by a charming garden courtyard that offers a glimpse into the home through floor-to-ceiling glass. Step inside this beautifully preserved period residence and prepare to be captivated by soaring vaulted ceilings and breathtaking gulf front views. The home also includes an additional seating area and a front patio, perfect for savoring some of Siesta Key's most spectacular vistas. A rare and highly coveted feature: the residence comes with a 1-car garage—a true amenity in this sought-after community

37 Sandy Cove Road Unit 3B, Sarasota
$2,299,000
3 Beds ⋅ 3 Baths ⋅ Windward Passage SubDv. ⋅ 34242 Zip Code
Under contract-accepting backup offers. Experience refined coastal living in North Siesta Key at 4708 Ocean Boulevard, a fully renovated 2025 corner residence ideally positioned on the Gulf of Mexico at Big Pass. This exceptional 3-bedroom, 3-bath condominium offers unobstructed panoramic views of the Gulf, Sarasota Bay, and distant vistas of Lido Key and downtown Sarasota. Encompassing 2,277 square feet with miles of Gulf-front views, the residence has been thoughtfully redesigned with wide-plank European engineered oak flooring, impact-rated windows and doors, and integrated smart-home technology throughout. The chef’s kitchen is a statement in both form and function, featuring custom cabinetry, Milano Dolomite countertops, a striking Macaubas Quartzite island, and premium GE Café appliances—perfect for entertaining against a backdrop of endless blue water. The primary suite is a private retreat with direct access to a Gulf-front balcony and a spa-inspired bath complete with dual vanities, rainfall shower, and bidet. Two additional guest suites provide comfort and privacy, each finished with designer details. Additional highlights include a two-car tandem garage with hurricane-rated door, new HVAC systems, electric hurricane shutters, and an integrated sound and entertainment system. Amenities include a heated pool, guest parking, and direct walking access to the sugar-white sands and vibrant Village of Siesta Key. This residence blends timeless coastal elegance with modern luxury—an extraordinary Gulf-front retreat on one of Siesta Key’s most coveted stretches of shoreline.

4708 Ocean Boulevard Unit E7, Sarasota
$570,000
2 Beds ⋅ 2 Baths ⋅ Vista Hermosa SubDv. ⋅ 34242 Zip Code
One or more photos have been virtually staged. Welcome to your maintenance free, dream beach retreat on Siesta Key! This charming and meticulously remodeled 2-bedroom, 2-bath villa offers the perfect blend of luxury and convenience, just a short stroll from the pristine sands of Crescent Beach. Enjoy cooking in a stunning kitchen featuring brand new quartz countertops, stainless steel appliances, and stylish light fixtures. Experience comfort year-round with newly installed HVAC and energy-efficient tankless water heater. Luxury vinyl panel floors flows seamlessly throughout, offering both durability and aesthetic appeal. Relax in the attached, screened-in lanai, complete with No-See-Um screen, aluminum framing and a new Hunter, wet-rated ceiling fan, perfect for warm island evenings. Both bathrooms have been beautifully remodeled providing a fresh, contemporary feel. Located just a few steps from the Clubhouse, heated pool, outside grilling areas and laundry facility. Walking distance to shops, restaurants and entertainment. Enjoy the easy, island lifestyle with access to the free trolley service to Siesta Key Village for even more shopping and dining experiences. Ideal for a second home, rental investment, or full-time residence. Don't miss this great opportunity to own a piece of paradise! Schedule your showing today and embrace the Siesta Key lifestyle!

191 Vista Hermosa Circle, Sarasota
$640,000
2 Beds ⋅ 2 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code
Location Location Location! Beautifully updated and fully furnished 2-bedroom, 2-bath condo with a great rental history, ideal as a beach retreat, primary residence, or income-producing property. Located in the highly desirable beachfront Tortuga community, this residence is just steps from the sand and offers the perfect blend of coastal lifestyle and everyday comfort. Professionally designed, the open-concept living area features modern finishes throughout. The kitchen offers sleek appliances, attractive cabinetry, and ample counter space, perfect for entertaining or daily living. The bright lanai provides peaceful Gulf views, ideal for relaxing and enjoying coastal breezes. Windows throughout the condo feature plantation shutters, providing elegance, privacy, and light control, while HURRICANE IMPACT-RESISTANT windows add comfort and peace of mind. The spacious primary suite includes an en-suite bath with tasteful designer details. Laundry connections are conveniently located in the second bedroom closet. Tortuga is a well-maintained, boutique community of just 77 residences, offering resort-style amenities including secure keyless entry, heated indoor/outdoor pool, sauna, sundeck with grills, private beach access, clubhouse with full kitchen and dining area, tennis and pickleball courts, boat docks (first-come, first-served), under-building garage parking with a designated space, and additional storage. Tortuga has taken meaningful steps toward future storm preparedness. The association has invested in flood mitigation measures, including portable flood dams and water rerouting systems, which would be deployed in the event of an approaching hurricane. Onsite manager; trash, water, basic cable, and internet included. The community has completed its Milestone Inspection, and NEW ELEVATOR, NEW ROOF, NEW gutters, NEW fire pump, building generator, pool pump, and pool heater have all been installed as part of major capital improvements, providing added peace of mind for new owners. Just steps from the trolley stop, with easy access to Siesta Key public beach and Siesta Key Village, where you can enjoy a variety of restaurants, shops, and live entertainment. Schedule your showing today!

8710 Midnight Pass Road Unit 501b, Sarasota
$815,000
2 Beds ⋅ 2 Baths ⋅ Excelsior Beach To Bay SubDv. ⋅ 34242 Zip Code
Fall in love with the natural light and tranquil views of the Intracoastal Waterway that define everyday living in this beautiful updated residence. Featuring soaring cathedral ceilings and expansive windows, this home is filled with sunlight while perfectly framing the stunning waterfront scenery. The open, airy layout creates an effortless flow ideal for both relaxing and entertaining. Enjoy gentle coastal breezes and the serenity of a quiet community, complete with your own deeded access to world famous Siesta Key Beach, known for its soft quartz sand and breathtaking sunsets. Surrounded by lush tropical landscaping, this home offers a peaceful and private setting while still delivering the vibrant coastal lifestyle Siesta Key is celebrated for. Whether you're seeking a full-time residence, a vacation getaway, or an investment opportunity, this property offers the perfect blend of luxury, comfort, and island charm. Resort style amenities include two pools, two hot tubs, tennis courts, pickleball, a fitness center, shuffleboard, a community room with kitchen, and a library with your next great read waiting for you. Best of all, this lovely unit is a Penthouse and End Unit so very peaceful and walking distance to shops and restaurants. Unit is turnkey furnished. Please watch Video 2 as it captures the lifestyle at Excelsior Beach to Bay and Siesta Key. Don’t miss out on this one, call today for your private showing.

6285 Midnight Pass Road Unit 307, Sarasota
$1,180,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Ideally located on Palm Island in the heart of Siesta Key, this elevated block-construction home offers the ultimate blend of style and resilience. Situated on nearly a quarter-acre, this 2-bedroom, 2-bathroom residence includes a generously-sized office currently utilized as a 3rd bedroom. Elevated over 10 feet, the home features a metal roof (2019), hurricane impact windows (2019), newer HVAC (2022) and new exterior paint (2026). The interior shines with fresh paint, designer lighting, and a custom statement banquette. An updated kitchen with marble countertops is open to the ample living and dining space, perfect for entertaining. The oversized owner’s suite boasts a walk-in closet and an ensuite bath with dual sinks, and double doors opening to the deck and pool area. Outside, enjoy the newly installed heated pool and paver deck overlooking a tranquil saltwater pond, which provides additional privacy. Just blocks from the world-famous Siesta Key Beach and less than a mile from the Village, this is island living at its finest.

421 Island Circle, Sarasota
$2,950,000
5 Beds ⋅ 6 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Rare opportunity on North Siesta Key’s Bay Island—one of the area’s most sought-after waterfront enclaves. Offered as-is, this 4,536-square-foot residence provides an exceptional opportunity to renovate, redesign, or completely reimagine to suit your vision for the home, while enjoying serene water views and an unbeatable island location. Surrounded by luxury homes and tropical landscapes, the property offers the relaxed coastal lifestyle Siesta Key is known for, with bayside scenery, gentle breezes, and incredible upside. The home’s generous size allows for flexible design possibilities, making it ideal for customization in one of the island’s most premium, high-demand neighborhoods. This is a phenomenal opportunity for an investor or end user seeking a large home on Siesta Key to transform however they choose. With significant potential to add value through renovation or redevelopment, this property represents a strong future investment opportunity in a market known for long-term appreciation. Whether planning a strategic update or a full-scale redesign, the upside is substantial. An exceptional value for buyers looking to create something truly special.

604 Norsota Way, Sarasota
$1,200,000
4 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
WELCOME to one of Siesta Key's hidden gems. From this Key West style home, you can walk or bike ride to the soft, quartz sands of Siesta Beach or the quaint Siesta Village in minutes. This exceptional home offers high end finishes throughout. The native yard features beach sunflowers and other native plants and shrubs. The front door entrance invites you into the main level with an easy flow between the living room and the dining room. The gourmet kitchen features wood cabinets, granite countertops, stainless steel appliances and French Door refrigerator. The guest bath, laundry room and bonus room complete the downstairs. The backyard is a fenced, private oasis with a pool surrounded by stone pavers with room for lounge chairs, grill and an outdoor table setting. Mature royal palm trees and smaller palms create a beautiful habitat for birds and other wildlife. The second floor has two comfortable bedrooms, one with a private balcony. A full bath completes this level. The top level offers a spacious Primary Bedroom and En Suite Bathroom retreat with exceptional amenities, a large bathroom with granite countertops, wrap-around walk-in shower, and separate garden tub, with a screened-in balcony overlooking the pool area. The top level is completed by an additional Bedroom with an en suite Bathroom with walk-in shower, linen closet, and granite countertops. Additional features include solar panels (paid in full), a security system, stone paved driveway and walkway, along with an oversized 2 car garage. This open, sunny home is located in a quiet neighborhood at the end of the street and has so many quality features. It is definitely worth a visit.

5201 Avenida Del Mare, Sarasota
$2,500,000
4 Beds ⋅ 5 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code
Gated Siesta Key Estate with Guest House & Boating Access. Experience the best of Siesta Key living, where award-winning white quartz sand beaches meet a relaxed island lifestyle, just minutes from Sarasota’s vibrant arts, dining, and cultural attractions. Don’t be deceived by the 1977 construction date. A 2003 addition doubled the size of this home. Metal roof installed in 2017. Pool and deck renewed in 2022. Brand new elevated sea wall and dock in 2023. 2 new A/C systems in 2026. And these are just some of the highlights. Tucked inside its own gated enclave, this exceptional waterfront estate with a detached guest house is surrounded by lush tropical landscaping, creating a secluded oasis. The thoughtfully designed open floor plan offers many possibilities. The kitchen serves as the heart of this home, opening seamlessly to a casual living area and dining space, while the expansive living room beyond features a fireplace and picture windows framing tranquil water and tropical views. A versatile flex room at the front of the home easily adapts to your lifestyle — ideal as a home office, formal dining room, or playroom. Additional conveniences include a half bath and an oversized laundry room with access to a spacious two-car garage with abundant storage. French doors at the rear of the home lead to the outdoor living area, where a heated saltwater pool and spa overlook peaceful canal views wrapping along the rear and side of the property. Upstairs, the impressive primary suite offers a true retreat, complete with its own fireplace and a luxuriously appointed spa-style bathroom. A generous second bedroom features an ensuite bathroom, while two additional bedrooms share a third bathroom. Wood flooring, marble tile, high-end finishes, and distinctive architectural details are showcased throughout. Adding flexibility, the detached guest suite includes a private entrance, studio, bathroom, kitchenette, and private courtyard — perfect for guests, multigenerational living, live-in staff, home office space, or fitness studio. Boating enthusiasts will appreciate immediate access to the waterfront lifestyle with a private dock, 7,000-pound boat lift, plus an included 18-foot boat with trailer and two kayaks — ready for adventure from day one. Ideally located in the heart of Siesta Key, the home is just steps from the Out-of-Door Academy school, and a walk or bike ride to Siesta Beach and Siesta Village. Convenient access to the north bridge makes reaching downtown Sarasota easy. Offered turnkey furnished, this extraordinary property is move-in ready and perfectly suited as a primary residence, seasonal retreat, vacation home, or rental investment opportunity.

4712 Higel Avenue, Sarasota
$1,299,900
2 Beds ⋅ 2 Baths ⋅ Dolphin Bay-Siesta Key SubDv. ⋅ 34242 Zip Code
Experience coastal luxury in this beautifully updated 2BR/2BA condo in the gated, waterfront community of Dolphin Bay on Siesta Key. This exceptional 4th floor residence blends modern sophistication with breathtaking Intracoastal Waterway views, creating a serene yet elevated island lifestyle. A charming front porch welcomes you—perfect for relaxing with a favorite beverage while grilling and enjoying city views. Inside, the spacious open-concept floor plan is thoughtfully designed for both comfort and style. Extensive kitchen and bath renovations completed in 2020 showcase contemporary finishes and high-end fixtures throughout. The chef’s kitchen features shaker-style cabinetry, quartz countertops, reverse osmosis system, and a built-in desk area with additional storage—both functional and elegant. The adjoining den, filled with natural light from sliding glass doors, offers a peaceful spot to read or work while taking in tranquil outdoor views. Immaculate hardwood floors flow through the living areas, adding warmth and timeless appeal. The dining room is enhanced by a custom built-in dry bar, ideal for entertaining. Expansive windows and sliding glass doors frame stunning southern views of the Intracoastal Waterway, where boats pass by, dolphins play, and coastal breezes set the mood. The enclosed, tiled lanai extends the living space and provides a perfect setting for gathering with friends and family while enjoying the scenery. The primary suite is a private retreat with its own lanai access, a spacious walk-in closet, and a luxurious en-suite bath featuring a soaking tub and tiled walk-in shower. The guest bedroom offers a private entrance to the front patio, generous storage with two closets (including a walk-in), and direct access to the guest bathroom. Additional features include an interior utility room with cabinetry, a newer hot water heater (2024), newer HVAC system (2018), and washer and dryer (2019)—making this a truly move-in-ready home. Private under-building garage parking and additional storage provide convenience and peace of mind. Dolphin Bay is a pet-friendly community offering resort-style amenities, including a pool & spa, fitness center, clubhouse, three Har-Tru tennis courts, fishing pier, and scenic walking paths. Enjoy an easy stroll or trolley ride to world-famous Siesta Key Beach, renowned for its powdery white sand, Pickleball courts, and laid-back island vibe. Schedule your private showing today and discover the best of Siesta Key living—no hurricane damage from any storms.

1260 Dolphin Bay Way Unit 403, Sarasota
$1,200,000
2 Beds ⋅ 2 Baths ⋅ Polynesian Gardens SubDv. ⋅ 34242 Zip Code
Rarely available direct bayfront 2/2 maintenance free villa in Polynesian Gardens. Magnificent views of the Intracoastal/Little Sarasota Bay. Watch the manatees and boats go by from your paved patio directly on the water. Spacious 2 bedrooms/2 full baths with very large great room. Updated kitchen and baths with new cabinetry, granite and stainless-steel appliances. Plenty of closet space. Garage with plenty of storage plus an extra driveway allows for 2 parking spaces. Newer washer/dryer in garage. Beautiful landscaping. Community has a heated pool, clubhouse and fishing pier. Close to shops, dining and America's #1 Beach - Siesta Key. Free trolley stops directly in the front of the community on Midnight Pass Road. Two pets allowed any size.

1320 Moonmist Drive Unit B-11, Sarasota
$3,900,000
5 Beds ⋅ 6 Baths ⋅ Siesta Cove Sub SubDv. ⋅ 34242 Zip Code
An extraordinary statement of modern coastal elegance, this custom waterfront residence built in 2018 is a masterclass in refined living, where architectural detail, craftsmanship, and setting converge in the coveted enclave of Siesta Cove. Framed by sweeping water views and constructed with hurricane-rated windows and doors, the residence offers both elevated design and enduring peace of mind. Spanning five bedrooms and six full bathrooms, the home is thoughtfully curated for effortless luxury. The primary en-suite retreat on the main level provides a private sanctuary, while light-filled interiors and tranquil water vistas create a seamless connection to the outdoors from nearly every room. The great room commands attention with intricate ceiling artistry, custom built-in shelving, and a sleek electric fireplace—an inviting yet dramatic centerpiece for both intimate evenings and grand entertaining. A temperature-controlled walk-in wine cellar and elegant wet bar elevate the experience further. At the heart of the home, the kitchen is a vision of light and sophistication, featuring new designer Cambria countertops (Wolf & Subzero appliances) including double ovens, built-in refrigerated drawer and a built-in freezer drawer, a generous walk-in pantry, and a welcoming eat-in layout complemented by an adjacent breakfast bar. Plantation shutters and discreet electric blinds throughout the home enhance the ambiance with effortless control of light and privacy. A richly appointed den or office behind French doors offers quiet refinement, while a sweeping staircase ascends to an upper level designed for both comfort and indulgence. Here, a spacious bonus room opens to a private screened balcony, ideal for sunrise reflections or sunset cocktails. Four additional bedrooms include three luxurious en-suite accommodations and a fourth with a dedicated full bath just beyond. One suite is distinguished by its own wet bar with refrigeration for morning coffee or evening refreshment, along with custom built-in closet drawers—an unexpected touch of indulgence. The outdoor living experience is nothing short of resort-caliber. A sparkling pool and spa, enhanced by a new electric pool heater, are complemented by an outdoor shower, built-in grill, and beverage cooler—creating a private oasis for entertaining under the stars. Boaters will appreciate the 39-foot private dock with water, electric, and lift, just moments (only 3 properties away) from the Intracoastal Waterway. Additional features include an elevator servicing all levels from the oversized three-car garage, abundant storage, a fully fenced yard, and lush, mature landscaping that envelops the property in privacy and beauty. Perfectly positioned near world-class beaches, upscale shopping, and fine dining, this exceptional Siesta Cove residence is more than a home—it is a lifestyle defined by grace, comfort, and uncompromising waterfront luxury.

5326 Siesta Cove Drive, Sarasota
$429,000
1 Beds ⋅ 1 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code
Come live the dream in this great "fully furnished" residence on the south end of Siesta Key. Share amenities with Turtle Bay across the street like tennis, pickleball, and boat slips. Directly on the gulf, enjoy beach and sun year round. Secure, under building covered parking. Washer/dryer combo in unit! This unit is clean and in fabulous condition and comes fully furnished. Situated at the southern end of Siesta Key, it offers a more remote feel. Take the trolley into the village for dinner and shopping. This unit shows excellent and is priced right!

8750 Midnight Pass Road Unit 302, Sarasota
$1,650,000
3 Beds ⋅ 4 Baths ⋅ Siesta Villa SubDv. ⋅ 34242 Zip Code
Superb Location. Big Family Retreat. Excellent Investment. Quiet Beach Days. The search for your ultimate beach retreat ends at 436 Canal Road. This 3-bedroom, 3 ½ bath home has all the extras you’re looking for. Your home is located just steps to world famous Siesta Key Beach. You are an easy walk, bike ride, or golf cart drive to Siesta Key Village where you will experience great food, entertainment and eclectic shopping. Enjoy fishing or dropping your kayak or paddleboard off your private community dock to explore Siesta Key by water. Or relax by the west-facing pool shared by only 4 units. At home, use your interior elevator to take you to all four floors. The oversized garage comes with a new garage door, a mini-split AC unit and plenty of room for your golf cart and beach toys. The first floor of living space has an open-plan kitchen with stainless steel appliances, a dining area and living room. There is also a balcony, laundry and half-bath on this floor. The next floor contains 3 spacious bedrooms and 2 baths. The Primary bedroom has an en-suite with dual sinks, both a garden tub and shower, and two walk-in closets. The top level had a surprise flex space that opens to the large roof top terrace with stunning views of the gulf. The flex space currently has 2 twin beds, a wet bar with under-counter sink, and a full bath with shower. Your home has a 2026 Roof, 2-AC units (2025 and 2022), and new Garage Door (2025). The property is currently being utilized as a WEEKLY rental and sleeps 8. The community is pet-friendly (owners only). Seller is grossing $100k using VRBO. Projections of $167,000+ with property manager. Come visit paradise on Siesta Key.

436 Canal Road Unit A, Sarasota
$649,000
2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code
Live your dream in this light and bright 6th-floor 2-bedroom, 2-bath condo with spectacular views of both the Gulf and the Bay! This unit is the perfect place to watch a sunrise or a sunset and soak in the beauty of Neville Preserve, Little Sarasota Bay, and the Gulf! Gorgeous bay views are showcased along the back of the unit through floor-to-ceiling sliders that span the entire space. The open kitchen features quartz countertops, white cabinetry, stainless steel appliances, and full Gulf views. The large master bedroom overlooks the Bay and features abundant closet space and an en-suite bath. A second bedroom and hall bath are ideal for family and/or guests. Additional conveniences include a washer/dryer in a closeted utility area and a ground level storage unit—perfect for beach and golf gear. An assigned covered parking space is conveniently located near the building entrance. Furnished and move-in ready!. The Pointe, a unique community located at the southernmost end of Siesta Key, is surrounded by water on three sides. Just south of The Pointe, recently reopened Midnight Pass connects the Bay and Intracoastal Waterway to the Gulf - enhancing boating, estuaries, marine life, and real estate values! A gated property, The Pointe is beautifully landscaped and features every amenity: a heated pool and spa, lighted tennis and pickle ball courts, private boat docks, kayak and paddleboard racks and launch, exercise rooms, men's and women's saunas, a beautiful club house with a fireplace and a full kitchen, a private island with gazebo and grills, and on site management and maintenance. This five plus acre property is conveniently located just a few minute's walk from Turtle Beach and three restaurants. Come live at the less traveled, more tranquil end of the Key and enjoy the walking and bike paths under tree-lined Midnight Pass Road. Boat docks are available!!

9393 Midnight Pass Road Unit 606, Sarasota
$640,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
Welcome to refined coastal living in this beautiful freestanding villa with a one-car garage, located in the premier Gulf-front community of Whispering Sands on Siesta Key Beach. Thoughtfully updated throughout in 2025, this light-filled residence offers three bedrooms and two bathrooms within approximately 1,400 square feet of refined living space, blending modern coastal style with everyday comfort. The brand-new kitchen is both stylish and functional, featuring quartz countertops, soft-close white cabinetry with pull-out drawers, a mosaic tile backsplash, Frigidaire stainless steel appliances, and a pantry for additional storage. The fully updated bathrooms showcase quartz countertops, soft-close white cabinetry, updated lighting, and glass-enclosed walk-in showers. Additional upgrades include fresh interior and exterior paint, new crown molding and baseboards, textured ceilings, recessed lighting, ceramic tile flooring throughout, and built-in closet organizers. All three bedrooms are generously sized, offering flexible space for seating or a workspace. The spacious living room accommodates multiple seating areas and features large glass sliders that flood the home with natural light and create seamless indoor-outdoor living. Sliding glass doors from the kitchen and dining area open to a large brick paver patio, ideal for relaxing or entertaining, with fencing between villas for added privacy. Further highlights include a new roof (2025), new AC unit, new hot water heater, new landscaping, a new full-size washer and dryer. Whispering Sands is a 55+ Gulf-front community offering resort-style amenities, including 800 feet of private deeded beach access, two clubhouses for social gatherings, two heated swimming pools, a fitness center, library, tiki hut picnic area with gas BBQ grills, shuffleboard courts, kayak and canoe storage, an active social calendar, and onsite rental management. The community is just steps from dining, shopping, and the vibrant atmosphere of Siesta Key Village. This move-in-ready villa offers resort-style, low-maintenance island living at its finest.

237 Hourglass Way Unit V6, Sarasota
$3,450,000
4 Beds ⋅ 4 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code
Welcome to a residence where inspired design meets the effortless elegance of Island living. Tucked away on the tranquil side of the Siesta Key Village, this extraordinary home places you at the heart of it all while having it all. With World-renowned beaches and the charming village just steps away… you truly can not beat the location. This 4 bedroom, 3100 sq.ft. home boasts a private boat dock, tropical backyard oasis and terraces with sunset views that never fail to inspire. The primary construction of this home was completed in 2018, with a full designer remodel in 2025. This home offers the confidence of modern construction throughout. Levels one through three are concrete block, with a two-by-six wood-frame fourth level and all exterior glass is hurricane impact rated. The home also boasts a standing-seam metal roof, a six-foot privacy wall with keypad-secured metal entry gates. A three-stop elevator services every floor, alongside a striking free-floating steel staircase framed by floor-to-ceiling glass, maintaining open sight-lines across the living spaces. Private bedrooms with en-suite bathrooms are thoughtfully positioned on levels two and four. Each floor opens to a generous covered balcony. Crowning the home is its most captivating feature: a spiral staircase leading from the fourth-floor balcony to a rooftop terrace with sweeping views of Siesta Village, Siesta Beach, Downtown Sarasota, and front-row vantage point to nightly stunning sunsets over the ocean. A comprehensive renovation brings a fresh, sophisticated vision to this home. The updates include new luxury hardwood flooring throughout, designer kitchen complete with dry-bar and a luxurious primary bathroom update. The second level serves as the home’s central gathering space, featuring an open-concept living room, dining area, and kitchen designed for both entertaining and everyday luxury. The kitchen has been elevated with brand-new custom floor to ceiling cabinetry complete with specialty lighting, premium Cambria countertops, as well as new appliances. The space is complimented by a beautifully designed dry bar and pantry for a refined, luxury finish.The high end finishes are complimented by designer furnishings and decor that convey with the sale of the home. At ground level, a two-car garage is complemented by a substantial 440-square-foot covered lanai overlooking a refreshing heated outdoor pool. The addition of an outdoor kitchen and upgraded, easily maintained, turf and stone landscape create seamless indoor-outdoor living and entertainment. Privacy is not an issue as this home boasts lush landscape and an impressive block wall enclosed yard. With Siesta’s gorgeous white sand beaches just a short walk from the home and a private boat dock just across the street enjoying the Ocean is a breeze from this property. The boat dock includes a 10,000-pound lift and space for a second lift, allowing for effortless access to the ocean via a canal. Siesta Key Village is a cherished walkable community rich with dining, boutiques, and local small businesses, including a Market, that evoke feelings of nostalgia. Yet the greatest luxury remains the timeless evening sunset strolls on the soft white sandy beaches. The Island’s effortless serenity reaffirms why Siesta Key is not merely a destination, but an exceptional place to call home.

5263 Avenida De Cortez, Sarasota
$1,050,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
New price! Beautifully remodeled and ideally just minutes from world-renowned white sands of Siesta Beach, this chic island pool home offers an exceptional blend of style, comfort, and storm-ready peace of mind. Designed for effortless coastal living, the open main living area is highlighted by a vaulted ceiling, transom windows, and abundant natural light, with French doors opening seamlessly to the private outdoor entertaining space. Porcelain flooring flows throughout the home, complemented by solid wood cabinetry, quartz countertops, and a thoughtfully designed kitchen featuring KitchenAid appliances, an electric range with exhaust hood, and clean, timeless finishes. The interior is further enhanced by solid wood interior doors, custom lighting, and new Minka ceiling fans, creating a polished yet inviting atmosphere. Significant recent upgrades add substantial value and confidence for today’s buyers, including hurricane-impact windows, a new impact front door and rear French doors (2024), a new HVAC system (2024), a shingle roof (2021), and a hurricane-rated garage door. The primary suite features a custom closet system and a separate owner’s closet, ideal for part-time use or rental flexibility. Outdoors, enjoy a resort-style heated saltwater pool and spa, enhanced by a new pool heater (2025) and pool filter (2024), surrounded by mature tropical vegetation that provides exceptional privacy. Manicured front landscaping with lush plantings, an irrigation system, a paver driveway, and a Trex front walkway complete the home’s inviting curb appeal. Additional features include epoxy-finished garage floors and a Ring doorbell with exterior security cameras. Adjacent to Glebe Park and close to Siesta Key Village, this residence offers easy access to dining, shopping, entertainment, and the beach. 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 Ringling Museum, Van Wezel Performing Arts Hall, St. Armands Circle and ever-popular Sarasota Farmers Market. Equally suited as a full-time residence, seasonal retreat or potential income-producing investment, this home delivers refined island living in one of Siesta Key’s desirable neighborhoods.

1002 Glebe Lane, Sarasota
$1,350,000
2 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
An unusual price for an unusual seaside residence. Completely renovated with stunning views from every window. Enjoy your morning coffee on the lanai and relish the downtown skyline as well as the Gulf of Mexico and Siesta Beach. Renovations include completely repainted, impact resistance windows, new interior doors, closet organizers and new front door. Casarina amenities include heated pool/spa, pickle ball/tennis courts, exercise room, gas grills, etc. This is worth a visit to see everything you can bring into your life.

5880 Midnight Pass Road Unit 804, Sarasota
$680,000
2 Beds ⋅ 2 Baths ⋅ Boca Siesta SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Private deeded 32 foot boat dock. Private beach access to Siesta Key Beach. Waterfront community on Sarasota Bay. Updated in 2019. Set on the bay side of Siesta Key, this beautifully renovated two bedroom two bath residence at Boca Siesta offers a lifestyle that feels both rare and natural. Located within a waterfront community on Sarasota Bay, the residence includes a private deeded 32 foot boat dock and private access to Siesta Key Beach, creating an exceptional balance of boating, beach access, and bayfront living. Located in the understated bayfront enclave of Boca Siesta, this residence enjoys peaceful bay views and a quieter sense of retreat, while Siesta Key Beach sits just across the street, known for its expansive shoreline and world famous quartz crystal sand. Updated in 2019, the residence features a more open and inviting floor plan with solid wood cabinetry offering generous storage, granite countertops, plantation shutters, crown molding, impact windows, new ceiling fans, and fresh interior paint. The open kitchen and great room combine living and dining areas oriented toward the bay and flow seamlessly into a screened private patio with impact windows overlooking Sarasota Bay. The primary suite offers calming bay views and a spacious ensuite bath with a jetted soaking tub, large walk in shower with rain shower head, dual vanities, and a generous walk in closet. The second bedroom and bath provide flexibility for guests, a home office, or additional living needs. Boating enthusiasts will appreciate the private deeded 32 foot boat dock that accommodates a larger vessel and provides direct access to Sarasota Bay. Additional conveniences include covered carport parking, private storage under the building, and an in unit full size washer and dryer located in a large utility room. Community amenities include a heated bayfront pool, tennis and pickleball courts, fishing pier, kayak launch, grilling areas, and a bayside clubhouse overlooking the bay with kitchen, bar, sauna, and fitness area. Private beach access is provided through the association, with access just across the street through Sarasota Surf & Racquet Club. From this location, Siesta Village, South Village dining, and downtown Sarasota are easily accessible by bike, free ride services, or the Siesta Key trolley. For those who choose Siesta Key for the water as much as the beach, Boca Siesta offers an effortless boating lifestyle where Sarasota Bay and Siesta Key Beach are part of everyday life. Experience life at Boca Siesta. To view a 360 walk through go to: https://funkypalmproductions.hd.pics/5911-Midnight-Pass-Rd-unit-206/idx

5911 Midnight Pass Road Unit 206, Sarasota
$500,500
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Discover the potential of this 2-bedroom, 2-bath condominium in the highly sought-after Peppertree Bay community on Siesta Key. Located on the Gulf side with deeded beach access, this residence offers easy, direct access to Siesta Key’s world-famous quartz sand beach, making it highly attractive to both owners and renters. The condo provides a great opportunity to personalize and add value to suit your style. Monthly rentals are permitted up to four times per year, offering strong income potential in a consistently high-demand vacation market. All new windows are scheduled to be installed in 2026 at no cost to the owner with no assessment required, enhancing long-term value and appeal. Peppertree Bay is a well-established, amenity-rich community featuring a resort-style pool, fitness center, tennis courts, and beautifully maintained grounds, all of which are highly desirable to owners and renters. Whether you’re seeking a personal beach retreat with income potential or a strategic investment on Siesta Key’s Gulf side, this property offers a rare combination of location, rental flexibility, and upside potential.

1125 W Peppertree Drive Unit 302, Sarasota
$875,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
LOCATION, LOCATION, LOCATION! Nestled within the highly desirable Peppertree Bay community, this exceptional first-floor island retreat offers breathtaking views and a serene coastal atmosphere. Designed with elevated ceilings and a well-appointed floor plan, this 2-bedroom, 2-bath residence lives more like a private home than a condominium. Great elevation with NO HURRICANE DAMAGE and NEW IMPACT WINDOWS providing additional protection and peace of mind. Upon entry, you are immediately welcomed by floor-to-ceiling windows that flood the space with natural light and showcase stunning views throughout the main living areas. The spacious open concept layout seamlessly connects the living area to the Florida Room, where sliding doors open to a paved patio, just perfect for entertaining, relaxing with friends, or enjoying a quiet evening cocktail. A defined dining area continues to enjoy picturesque views, while the custom kitchen will delight any home chef with abundant cabinetry, generous workspace, granite countertops, mosaic tile backsplash, and stainless-steel appliances. The spacious primary suite features multiple closets and a private en-suite bath, while a well-appointed guest bedroom and second full bath provide comfort and privacy for visiting family and friends. A PRIVATE GARAGE, an exceptional and highly sought-after feature on Siesta Key, adds tremendous value and convenience. Peppertree Bay is an amenity-rich community offering two heated pools, a fishing pier, BBQ and picnic areas, tennis courts, a fitness center, and two clubhouses with fully equipped kitchens and regular social events. Enjoy the closeness of Siesta Key Village for live music, shopping, and dining, or take advantage of easy on-and-off island access to all that Sarasota has to offer. Offered turnkey furnished and move-in ready, this stunning residence is ideal as a full-time home or a luxurious vacation retreat. Just bring your toothbrush and start living the Florida dream.

6047 E Peppertree Way Unit 224, Sarasota
$625,000
2 Beds ⋅ 2 Baths ⋅ Villa Navarra SubDv. ⋅ 34242 Zip Code
Discover this beautiful upstairs furnished condo in a highly desirable complex that is ideally situated in the Mira Mar neighborhood adjacent to the Siesta Key Village! Just a short stroll to the beach and mere moments from top dining, shopping, and nightlife, this unit is the ultimate coastal escape. Enjoy worry-free living with impact windows and sliding doors, a 2024 washer/dryer in the unit, and a 2022 water heater. NEW ROOF, no assessments, and no flooding concerns make this an exceptional find! Both the bathrooms and the kitchen have been tastefully renovated with sleek quartz countertops. The entire unit features neutral ceramic plank-tile flooring and a cohesive neutral palette throughout. Unwind on your screened in lanai, enveloped by lush palms and tropical greenery. Leave your car at home and soak in the beauty of Siesta Key Beach—ranked the #1 beach in the U.S. You are just 2/10 of a mile away from Sunset Pier where pristine white quartz sand, crystal-clear waters, and breathtaking sunsets await. Whether you're seeking a primary residence or the perfect island getaway, this beautifully maintained boutique community of just 16 condos offers an unbeatable location. Don’t miss this rare opportunity!

137 Avenida Messina Unit 3, Sarasota
$425,000
1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code
Beachside Living at Its Best - Casa Mar on Siesta Key Welcome to Casa Mar, a sought-after beachfront community offering the perfect combination of island charm and modern convenience. This 1-bedroom, 1-bathroom furnished unit is a rare opportunity to create your very own coastal getaway or capitalize on a high-demand vacation rental investment. Located just a 1-minute walk from world-renowned Siesta Beach, this bright and inviting unit overlooks the community pool and is ideally situated for effortless access to the Gulf. Recent updates include new laminate flooring in the bedroom , updated kitchen and new living room furniture. This unit also comes with a covered 1-car carport, offering protection from the elements and added convenience for beach living. Casa Mar is a true resort-style community, offering two swimming pools, tennis court, shuffleboard court, outdoor gas grills, and private beach access. With lush landscaping, tropical ambiance, and a friendly atmosphere, it’s the ideal place to relax, unwind, and enjoy the Florida lifestyle. Don’t miss the chance to own a piece of paradise, close to dining, shopping, and all the charm of Siesta Key Village, while also benefiting from strong income potential when not in personal use. This is your opportunity to live the beach life and make it truly your own.

6006 Midnight Pass Road Unit 4, Sarasota
$775,000
3 Beds ⋅ 3 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Private end-unit residence at Peppertree Bay with outdoor patio space, lush tropical landscaping, and an easy stroll to the bayside community pool from the back door. Inside, you’ll find extensive renovations and updates throughout, including new flooring, doors, fans and fixtures, walls, baseboards, and cabinetry. Major system improvements have also been completed, including waste lines, A/C, appliances and washer, dryer. Both the primary and guest baths have been updated along with a major enhancement to the kitchen. The 1st and 2nd floor lanai windows have been recently replaced—bringing in light while providing enhancing comfort and extended living space. A rare combination of privacy, thoughtful upgrades, and that classic Peppertree Bay lifestyle on Siesta Key. Must see and easy to show.

1201 E Peppertree Drive Unit 234, Sarasota
$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
$990,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Experience Luxury Living on Siesta Key! Welcome to the Gulf & Bay Club Condominium perfectly situated on the pristine shores of Siesta Key. This stunning Gulf-front property offers unparalleled beach living, making it the ultimate coastal retreat. This unit is offered turnkey furnished, ready for immediate enjoyment. 2-bedroom, 2-bathroom residence presents an expansive floor plan highlighted with a new kitchen featuring new appliances, granite countertops,new cabinets, and refined accents. The kitchen seamlessly transitions into a spacious living area with enclosed lanai adding additional space in your living area. Offered turnkey furnished with a sophisticated beach ambiance. Master bath featuring dual sinks, quartz countertops and large walk-in shower. The additional bedroom for your guests includes an ensuite bath which offers ample space. Door lock, gate, building, and beach access. Plus an owner’s storage closets for rental convenience. This property serves as a tranquil retreat in an exceptional location whether you're seeking a permanent residence, a vacation getaway, or a profitable rental property. The building boasts an array of amenities designed to elevate everyday living, including onsite management for added convenience. Two electric vehicle charging stations that are available, 3 Large heated pools w/wifi including 1 lap pool, 800ft Private soft white sandy beach, 6 Tennis courts including 1 Har-Tru court, 6 Pickleball courts, Basketball/Racquetball/Pickleball courts, Shuffleboard court, Organized seasonal golf for men and women, State of the art fitness center, including free weights and yoga room, 6 Dry saunas, hot tub, 2 Clubhouses – library with books, bar, pool table and TV’s, Numerous social activities during season, World famous Siesta Key Beach – #1 by TripAdvisor, Directly on the beautiful Gulf of Mexico, Spectacular sunrises and sunsets

5780 Midnight Pass Road Unit 207, Sarasota
$2,550,000
6 Beds ⋅ 4 Baths ⋅ Point Of Rocks Terrace SubDv. ⋅ 34242 Zip Code
Exceptional four-unit boutique coastal hospitality investment ideally positioned directly across from PB13 public beach access on legendary Siesta Key. This distinguished property represents one of the island’s most compelling income-producing opportunities, offering immediate access to Siesta Beach, ranked the #1 Beach in America and #4 worldwide by TripAdvisor’s 2025 Travelers’ Choice Awards. Renowned for its 99% pure quartz crystal sand and vibrant turquoise Gulf waters, this iconic destination delivers an unparalleled coastal experience that drives year-round demand. The intimate complex features a desirable mix of one and two bedroom residences and is professionally managed and offered fully turnkey, with all systems, furnishings, and operational components optimized for short-term rental performance. This established, high-performing hospitality asset demonstrates strong guest appeal, repeat bookings, and the ability to command premium nightly rates, allowing a new owner to seamlessly step into a stabilized operation from day one. Guests are consistently drawn to the unbeatable across-the-street beach access, eliminating parking hassles and enhancing walkability, an increasingly rare and highly sought-after advantage that supports rate premiums throughout the year. The property’s boutique scale and coastal charm deliver the personalized, resort-style experience today’s travelers prefer, further strengthening occupancy and guest loyalty. No rental restrictions provide a critical competitive edge, offering complete flexibility to optimize booking strategies, pricing models, and minimum stays without regulatory limitations. Strong financials underscore the property’s exceptional performance. With limited comparable inventory, enduring demand for high-quality coastal accommodations, and an irreplaceable location on Siesta Key, this offering represents a rare opportunity to acquire a trophy boutique hospitality asset in one of Florida’s most coveted beach markets. The Point of Rocks location further elevates market performance, placing guests within walking distance of Crescent Village’s restaurants, shops, and boutiques, while maintaining direct proximity to one of the world’s most celebrated beaches. This is a truly exceptional acquisition for investors seeking immediate cash flow, long-term appreciation, and a premier presence in an iconic coastal destination.

6905 Point Of Rocks Road, Sarasota