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742 Edgemere, Siesta Key
$1,525,000
3 Beds ⋅ 2 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code
Build or Renovate Discover an exceptional waterfront opportunity in the coveted Siesta Isles neighborhood on Siesta Key. Situated on an oversized lot at the intersection of two canals, this property offers 118 feet of seawall, wide water views, and direct boating access to the Intracoastal Waterway and the Gulf of Mexico. Experience prime Grand Canal waterfront, featuring a private dock and boat/jet ski lift. The existing 3BR/2BA 1960s home features a split-bedroom layout, water views from the main living areas and primary suite, a two-car garage, interior laundry, Italian tile flooring, and a spacious screened lanai overlooking the expansive backyard—providing excellent space for a future pool. Mature tropical landscaping and a canopied street enhance the property’s appeal. Important: The home experienced water intrusion during Hurricane Helene (Sept 2024) and is being sold AS-IS. This is a prime opportunity for renovators, investors, or anyone looking to build a custom waterfront estate in one of Siesta Key’s canal-front locations. Ideally located minutes from Siesta Key Village’s dining and shopping, and the world-famous powder-white sands of Siesta Beach. Downtown Sarasota is only a 15-minute drive. No HOA A rare oversized waterfront parcel on the Grand Canal—renovate, rebuild, and create your ideal Siesta Key retreat.

742 Edgemere, Siesta Key

749 Tropical Circle, Sarasota
$1,510,000
4 Beds ⋅ 3 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
A private tropical haven in the heart of Siesta Key, beautifully reimagined coastal retreat tucked away on nearly half an acre in one of Siesta Key’s most coveted neighborhoods. This stunning four-bedroom, two-and-a-half-bath pool home lives effortlessly, blending relaxed island living with thoughtful modern design, all just minutes from world-renowned Siesta Beach and the vibrant energy of Siesta Village. Completely transformed in 2023 by the former contractor-owner for his family, the residence showcases quality craftsmanship, contemporary finishes, and a warm, inviting aesthetic. Sunlight pours through impact-rated windows, highlighting open living spaces that flow seamlessly toward the outdoors. The expansive great room anchors the home and connects naturally to the newly staged interiors, creating an ideal environment for everyday living and entertaining. At the heart of the home, the chef’s kitchen is an absolute showpiece, featuring a striking reclaimed-oak island, open oak shelving, handmade tile, quartz surfaces, premium appliances, and exceptional storage including a full-height pantry wall. The design balances beauty and function with ease. The spacious primary suite offers serenity and privacy with a spa-inspired bath, while three additional bedrooms provide flexibility for guests, family, a home office, or creative space. A full interior laundry room, half-bath, and oversized two-car garage add convenience. Step outside to your own tropical oasis. A large, screened lanai opens to lush gardens, a newly renovated pool with updated equipment, and an expansive paver deck; perfect for relaxing in the sun or hosting gatherings under the palms. This exceptional property offers peace of mind with solid concrete block construction, no flood or hurricane damage, and a long list of upgrades, including new kitchen, baths, plumbing updates, air conditioning and ductwork, water heater, pool equipment, paver driveway, and more. Move-in ready, beautifully staged and ideally located, this is coastal living at its best. Enjoy quick access to Siesta Beach, the Village, boat launches, dining, and all that Sarasota offers.

749 Tropical Circle, Sarasota

7320 Melaleuca Way, Siesta Key
$1,500,000
4 Beds ⋅ 4 Baths ⋅ Sanderling Club SubDv. ⋅ 34242 Zip Code
Welcome to the Sanderling Club, one of Siesta Key’s exclusive and sought-after neighborhoods, offering luxury living in the heart of paradise. As the island’s only gated single-family home community with 24-hour staffed security, Sanderling Club is renowned for its breathtaking beachfront properties, lush landscapes and outstanding amenities. This unique property offers two separate residences, with new roofs and exterior paint, and includes a combined four bedrooms, four bathrooms and 3,766 square feet of refined living space, including additional non-conforming living areas. Among grand live oaks and overlooking the waters of the Heron Lagoon with a combined nearly 50 acres of tranquil waters — a kayak enthusiast’s dream — the home is designed to embrace natural beauty that surrounds it. The main residence was originally built in 1960 and completely remodeled in 2010, featuring beautiful, polished travertine floors, soaring vaulted ceilings with skylights that illuminate the main living areas, and custom built-ins throughout. A modern chef’s kitchen showcases rich-toned cabinetry, stone countertops, a five-burner gas cooktop, built-in stainless steel ovens and refrigerator, a spacious pantry, and a large laundry room with built-in desk and ample storage. This home also features an open-concept den with built-ins. The dining room, wrapped in a wall of impact glass windows with lanai access, creates an ideal space for casual living and elegant entertaining. The private owner’s/primary suite occupies the entire upper level, offering an en-suite bath, private viewing deck, custom built-in bamboo cabinetry and convenient access to the guest house/in-law suite. The ground level includes a bedroom, bath, flex room with kitchenette, and an air-conditioned one-car garage with new epoxy-coated floors and 13-by-21-foot loft storage space. The guest house, with elevator access, was built in 2008 and features a combined living room and kitchen space, two bedrooms, a full bath, laundry facilities, two-car garage with additional storage and expansive decks overlooking the tropical landscaped backyard and Heron Lagoon waters — the ideal retreat for guests or extended family. The expansive backyard offers space to create your tropical oasis, with room for a pool and spa. Sanderling Club’s premier amenities include new Har-Tru tennis courts, pickleball, playground and a newly remodeled clubhouse (coming soon). Boat slips, when available, offer direct access to Sarasota Bay, the Intracoastal Waterway and the Gulf. All of this is just minutes from Siesta Key’s world-famous crystal quartz sand beaches and the charming shops and restaurants of Siesta Village. Plus, downtown Sarasota’s vibrant arts and culture scene — with its theaters, ballet, opera, museums, galleries and shopping — is just a short drive away. Don’t miss this rare opportunity to experience the best of coastal luxury living on Siesta Key.

7320 Melaleuca Way, Siesta Key

1038 Contento Street, Sarasota
$1,500,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Siesta Key Canal Front Home with 175’ of sea wall on the Grand Canal in the desirable and quaint neighborhood of Siesta Isles. Ride your bike to the Village or the world-famous Siesta Key Beach rated #1 in USA. This beautifully well-kept 3 bedroom, 2 bath Rutenberg built home is located on a quiet cul-de-sac that is a perennial favorite with lush tropical landscaping and great privacy. The home sits high up on almost a 1/3 of an acre. This home was not affected by hurricane damage. Enter thru the charming Spanish style courtyard with its new landscaping, double front doors and wide foyer. Boasting a flowing floor plan with tile floors and crown molding, the living room & dining room open to the custom gourmet kitchen, featuring handsome wood cabinets, granite counters, & tumbled stone backsplash, perfect for entertaining while overlooking the Grand Canal from any window. The master bedroom ensuite with private sitting area is nice to enjoy. A new lanai cage installed July 2025. The lanai area faces southeast . There is a paver sundeck & outdoor dining area along with a covered lanai with rectangular pool, boat lift, dock, and cement seawall. Relax while you enjoy the serene water views and fabulous Florida wildlife, manatee, native birds and many types of fish. You may also enjoy fishing or kayaking from your backyard! Tropical mature foliage in park-like yard. Minutes to the open bay by boat and near Siesta Key Village where you can enjoy shops and restaurants. This truly is Paradise! Isn't this the lifestyle you've been planning? Selling Turn Key! Great Rental Income!

1038 Contento Street, Sarasota

1136 Seaside Drive, 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

4822 Ocean Boulevard Unit 8C, Sarasota
$1,475,000
3 Beds ⋅ 3 Baths ⋅ Siesta Towers SubDv. ⋅ 34242 Zip Code
Perched high above the shoreline, Residence 8C at Siesta Towers delivers nearly 360-degree views spanning the Gulf, Big Pass, Sarasota Bay, and the twinkling downtown skyline. From glowing sunsets to sparkling city lights, this vantage point is among the most extraordinary on Siesta Key. Rarely available, this three-bedroom, three-bath residence has just undergone a complete, top-to-bottom remodel. Every detail was thoughtfully curated with today’s luxury buyer in mind—offering the ease of brand-new finishes within an iconic Siesta Key location. Designed with a sleek, modern aesthetic, the open floor plan showcases impact-rated windows and sliding glass doors, wide-plank luxury flooring, custom recessed lighting, and a seamless indoor-outdoor flow. The all-new designer kitchen is appointed with quartz countertops, custom soft-close cabinetry, premium stainless-steel smart appliances, and a striking island ideal for entertaining. Each of the three en-suite bathrooms has been fully redesigned with spa-level finishes, frameless glass showers, elegant tilework, and contemporary fixtures. The spacious primary suite is a retreat in itself, featuring a tranquil en-suite bath and panoramic water views. Siesta Towers is a secure, well-managed waterfront community offering an enviable lifestyle. Building amenities include secure access-controlled entry, 24/7 security, a remodeled club room, fitness room, heated waterfront pool, BBQ grills, fishing dock, social dock, bike storage, and more. Just beyond your door, Siesta Village’s restaurants, shops, and nightlife are a short stroll away, with the powdery sands of world-renowned Siesta Beach minutes from home. This residence combines the rarity of a three-bedroom layout with a brand-new, complete remodel and nearly all-around views—an exceptional opportunity to own one of Siesta Key’s most striking vantage points.

4822 Ocean Boulevard Unit 8C, Sarasota

4108 Roberts Point Road, Sarasota
$1,450,000
3 Beds ⋅ 3 Baths ⋅ Roberts Point SubDv. ⋅ 34242 Zip Code
PRICE REDUCED $100,000 — FULLY FURNISHED* Whether you are looking for the IDEAL SECOND HOME that's furnished, has a pool and low maintenance grounds, or a PERFECTLY APPOINTED, remodeled with DESIGNER LIGHTING, 3 bedroom home, this fits the bill. Welcome to Roberts Point Road, one of the most desirable streets on Siesta Key—just steps to Shell Beach and minutes to the North Bridge for easy mainland access. This coastal residence blends island charm with smart, modern updates and is offered fully furnished for immediate, effortless enjoyment. Enter through a tranquil, private courtyard—perfect for quiet mornings or intimate evenings—into a dramatic, sunlit interior with soaring 22' ceilings and grand windows. The open-concept living area is anchored by a beautifully appointed, REMODELED KITCHEN with a center island, high-end fixtures, and dining space. Seamless indoor-outdoor living extends to a front courtyard patio with a HEATED POOL and a conveniently fenced, turfed backyard space that’s both low-maintenance but perfect for a dog run. The first-floor primary suite offers direct access to the courtyard balcony, dual walk-in closets, and a REMODELED dual vanity LUXURIOUS BATH. Enjoy two laundry rooms for ultimate convenience—one downstairs adjacent to the primary suite and a second laundry upstairs. The upper level provides two flexible bonus areas—ideal for a MEDIA LOFT and a DEDICATED OFFICE SPACE with built-in cabinetry. Signature updates include: NEW 2024 ROOF (big-ticket item complete), NEW POOL HEATER, NEW PAVER DRIVER and NEW PRIVACY LANDSCAPING—all enhancing comfort, curb appeal, and peace of mind. Bike to Siesta Key Beach, or head to Siesta Key Village, Southside Village, and downtown in minutes. CALL TODAY TO VIEW this the perfect, fully-furnished* island home—freshly updated, beautifully appointed, and ready now. (*staged items n/a).

4108 Roberts Point Road, Sarasota

704 Tropical Circle, Sarasota
$1,425,000
3 Beds ⋅ 2 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Nestled in one of Siesta Key’s most sought-after neighborhoods, this beautifully updated tropical retreat offers the perfect blend of coastal charm, modern comfort, and an active waterfront lifestyle. Whether you’re searching for a full-time residence or a private vacation escape, this home delivers an exceptional opportunity in an unbeatable location—just under a mile from the world-renowned white quartz sands of Siesta Key Beach. Set on a tropically landscaped low maintenance lot, the home has been thoughtfully updated to create a light, inviting interior centered around a modernized kitchen. A generously sized island anchors the space, serving as the heart of the home, ideal for entertaining family and friends. The open dining area overlooks the newer heated saltwater pool and screened enclosure, creating a seamless indoor-outdoor flow for relaxed coastal living. Evenings here are unforgettable, whether enjoying dinner al fresco or taking a moonlit swim beneath the warm tropical sky. The residence offers three spacious bedrooms, including a flexible guest room with a Murphy bed, allowing for both everyday comfort and effortless hosting. An additional office space off the pool area also features a Murphy bed, providing even more versatility for guests or extended stays.What truly sets this property apart is its connection to nature and the water. A charming boardwalk travels through lush mangroves, leading to your private dock perfect for launching kayaks and exploring the serene waters of the Bayside Club estuary. From here, you’ll enjoy quick access to the Intracoastal Waterway and beyond, opening the door to endless days of coastal adventure. All of this natural beauty comes with the assurance that this home had no damage nor flooding from previous storms. Offered with timely occupancy, this is a rare opportunity to secure your place in one of Siesta Key’s most desirable enclaves and begin enjoying the best of island living without delay for this summer.

704 Tropical Circle, Sarasota

324 Siesta Drive, Sarasota
$1,400,000
5 Beds ⋅ 4 Baths ⋅ Siesta Rev Of SubDv. ⋅ 34242 Zip Code
Virtually Staged. Welcome to the #1 beach in the US and top 50 in the world- Siesta Key, FL. Whether you're seeking a primary residence or a high-performing Airbnb investment, this fully renovated 5-bedroom, 4-bathroom coastal contemporary pool home offers the best of both worlds! Ideally situated on an oversized corner lot on Siesta Key and located within city limits, this MOVE-IN READY gem legally qualifies for 7-day minimum rentals, making it a prime opportunity for full-time living, or a lucrative short-term vacation rental. Nestled behind a grand privacy wall, this unique masterpiece provides a true tropical retreat for you and your guests. From the moment you step inside, you'll be captivated by the soaring 12-foot ceilings on both levels, the open concept floor plan, and elegant travertine marble flooring throughout. The primary suite is conveniently located on the first floor, offering both comfort and privacy with French doors that lead to your outdoor private patio. Custom hurricane-impact French doors wrap the entire main living area, seamlessly blending indoor and outdoor spaces, creating a dramatic view of your tropical oasis. Enjoy peace of mind with HURRICANE-IMPACT WINDOWS and DOORS installed throughout the home. Ample on-site parking for up to 4 vehicles adds exceptional convenience for both owners and guests. The chef’s kitchen is fully equipped with high-end finishes, including a gourmet gas range and hood, custom wood cabinetry, quartz countertops, an oversized BLANCO sink, and wine cooler, perfect for hosting and entertaining. Some of the recent upgrades include two brand-new HVAC systems (one for each level), new hot water heater, all new appliances, fresh interior and exterior paint, new landscaping and irrigation, and plumbing complete with a convenient manifold in the garage for your shut off valves. The newly resurfaced pool, paired with new pool equipment, invites you to relax in total serenity. Surrounded by lush, tropical landscaping, the spacious outdoor area offers plenty of room to entertain guests or simply soak in the Florida sunshine in total privacy. This residence is located just four blocks from the nearest beach access at N. Shell Rd, and near the North bridge for convenient access to and from the Key. Take a short ride to the world-famous Siesta Key Beach and Village, where you'll enjoy fine dining, boutique shopping, and vibrant island living. Known for its powder-soft quartz sand, Siesta Key consistently ranks among the top beaches in the United States, making this a premier location for homeowners and investors alike. Call today to schedule your private showing!

324 Siesta Drive, Sarasota

5215 Cape Leyte Drive, Sarasota
$1,400,000
3 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
JUST REDUCED!! SIESTA ISLES Waterfront Gem. Experience the best of Siesta Key living in this well maintained 3-bedroom + den, 3-bath pool home with 135+ feet of frontage on the Grand Canal. Situated on an oversized 15,269 sq ft /.35-acre lot, this residence offers the perfect blend of privacy, upgrades, and waterfront lifestyle. Situated well back from the street, the home opens with a welcoming foyer and expansive great room featuring vaulted ceilings, impact windows and impact sliding glass doors flooding the space with natural light while framing serene garden and waterway views. Two bedrooms feature en-suite baths and direct access to the back yard, while the primary suite’s bath connects conveniently to the pool area. Enjoy the privacy of this tropical retreat, swim in the sparkling pool, rinse off in the outdoor shower, or launch kayaks and paddleboards from the floating dock. With space to add a full dock or lift, boaters will love the water access via one fixed bridge to the Intracoastal Waterway. Practical updates bring peace of mind, including a durable metal roof and maintenance contracts for irrigation, AC, pest control, and alarm systems. The home has county water and sewer and there's a shared irrigation well that sustains the mature landscaping. The home experienced NO WATER INTRUSTION during last year’s storms and is truly move-in ready. A winding walkway through lush landscaping leads to the waterfront patio, while an extended brick paver driveway offers ample guest parking. Just minutes from Siesta Key’s world-famous beaches and The Village’s varied dining and shopping options, this home is ideal as a full-time residence or lucrative rental investment. Don’t miss your chance to own a slice of paradise on the Grand Canal—schedule your private showing today!

5215 Cape Leyte Drive, Sarasota

2 Island Circle, Sarasota
$1,400,000
5 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
*2 BUILDABLE WATERFRONT LOTS* Palm Island IS the "Heart of Siesta Key". Don't miss this rare opportunity to live in Siesta Key's most sought-after neighborhood and experience the quiet, friendly, yet close to everything community of Palm Island. Build your tropical dream home on one lot and sell the other, or go "all in" and create your ideal island estate on the 17,883 sq ft lot. If restoration is more your style, this home was built using the Lamolithic poured in place construction method developed by John Lambie Jr and was a key design element in the Sarasota School of Architecture. As a result, most of the primary structure and walls are made of 12 inch poured concrete, providing unsurpassed strength and durability. This spacious property located in one of the finest and friendliest communities on Siesta Key is situated a mere 600 feet from arguably the best beach on the planet. Situated on the Grand Canal, it is minutes by boat to the Intercoastal Waterway and a short walk or bike ride to Siesta Key Village. This sought after Palm Island address sits on two county approved building lots and is a rare opportunity for all interests. Maximize your Island experience and treat yourself to this rare, peaceful island escape limited only by your imagination. *House Plans and Budget available for both lots

2 Island Circle, Sarasota

915 Seaside Drive Unit 604, Sarasota
$1,400,000
3 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Live in it, rent it or enjoy the best of both worlds. Welcome to Hyatt Residence Club Sarasota – Siesta Key Beach, where effortless ownership meets elevated coastal living. Residence 604 at 915 Seaside Drive offers a rare opportunity to own a fully furnished 3-bedroom, 3-bath luxury condominium with sweeping city and skyline views, just steps from the world-famous quartz sands of Siesta Key Beach. This thoughtfully designed residence features an open-concept layout ideal for both everyday living and entertaining. Floor-to-ceiling windows fill the space with natural light, while the gourmet kitchen showcases high-end appliances, custom cabinetry, and premium finishes. The private terrace provides a front-row seat to vibrant city sunrises, and the spa-inspired bathrooms complete the experience of refined comfort. Ownership at the Hyatt Residence Club is truly turnkey. Enjoy a seamless lifestyle with resort-style amenities, including a beachfront pool and spa, state-of-the-art fitness center, private cabanas, and beautifully appointed lounges. Owners and guests benefit from on-site concierge services, housekeeping, a 24-hour staffed front desk, secure access, and reserved owner parking, all within a boutique luxury setting. Perfectly positioned near Siesta Key Village, you’re moments from renowned dining, shopping, nightlife, and endless outdoor activities—from kayaking the mangroves to sunset strolls along the beach. Whether you’re seeking a low-maintenance second home, an income-producing property, or a flexible coastal retreat, this residence delivers unmatched convenience and lifestyle in one of Florida’s most iconic destinations. Turnkey. Timeless. Siesta Key living at its finest.

915 Seaside Drive Unit 604, Sarasota

1001 Point Of Rocks Road Unit 312, Sarasota
$1,398,000
2 Beds ⋅ 2 Baths ⋅ Siesta Sands Resort SubDv. ⋅ 34242 Zip Code
This spacious and well-appointed direct beachfront condo, located at the southern end of Crescent Beach in one of Siesta Key's most desirable boutique resort communities, offers an exceptional coastal living experience. Unit 312, situated on the 3rd floor, features 2 bedrooms, 2 bathrooms, and two private balconies overlooking the beach, where you can enjoy sweeping Gulf views, refreshing tropical breezes, and unforgettable sunsets year-round. A private parking space, in-unit laundry, and private storage add everyday convenience. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service for lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room, and the serene bamboo lounge. This boutique beachfront community offers a secluded, gated retreat with only 31 units and exclusive private beach access to Crescent Beach. The unbeatable location places you just steps from Siesta Key's South Village.

1001 Point Of Rocks Road Unit 312, Sarasota

3446 Anglin Drive, 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

353 Avenida Leona, Sarasota
$1,385,000
3 Beds ⋅ 2 Baths ⋅ Siesta Manor SubDv. ⋅ 34242 Zip Code
Positioned along a quiet residential canal just moments from shops and restaurants of Siesta Village and a short distance to world-famous Siesta Beach, this extensively renovated coastal retreat offers the ideal blend of island charm, modern updates and exceptional value. Built in 1971 and thoughtfully reimagined in 2025, this three-bedroom, two-bath residence spans 1,730 square feet and showcases timeless finishes designed for effortless Florida living. From the moment you arrive, tropical landscaping and a welcoming entry set the tone. Natural light fills the expansive living space, where pocket sliding glass doors fully open to the screened lanai, creating seamless indoor-outdoor flow and picturesque views of the pool and canal beyond. The open dining area blends beautifully into the exquisitely updated kitchen, anchored by a striking 9-foot center island with counter-height seating, soft-close cabinetry, undercabinet lighting, terrazzo-inspired recycled glass countertops, designer tile backsplash and stainless-steel appliances. The serene primary suite opens directly to the lanai and features a custom walk-in closet and an elegantly appointed en-suite bath with granite-topped vanity and beautifully tiled walk-in shower. Two additional bedrooms offer walk-in closets, while the guest bath has been thoughtfully updated with quartz vanity and sleek tile finishes. Outdoor living is equally impressive, with a heated pool featuring a seating ledge and newer heater, all set within a fully fenced backyard overlooking the tranquil canal. The covered lanai includes a motorized screen, enhancing comfort and year-round enjoyment. Notable improvements include impact-rated windows and doors, luxury vinyl plank flooring throughout, updated baths, house replumbed in 2025, attic ductwork and insulation replaced, and a completely replaced and repoured seawall in 2020. An attached one-car garage with epoxy flooring and integrated storage adds functionality. Whether you’re seeking a refined island retreat, a smart investment opportunity or a boating-friendly lifestyle just minutes from the Gulf, this move-in-ready Siesta Key home presents a compelling opportunity in one of Sarasota’s desirable coastal communities. Schedule your private showing today.

353 Avenida Leona, Sarasota

6144 Midnight Pass Road Unit 3N, Sarasota
$1,377,500
2 Beds ⋅ 2 Baths ⋅ Island House SubDv. ⋅ 34242 Zip Code
Island House Dream Condo on Siesta Key! Experience the best of beachfront living at Island House on world-famous Siesta Key, where breathtaking Gulf views, unbeatable location, and effortless island living come together. Perfectly positioned in one of the most desirable beachfront buildings in the community, this second-floor condo offers truly unobstructed beach and water views with no other condo or building standing in your way. From the moment you arrive, the view takes center stage. Enjoy stunning beach views from all living areas, including the living room, guest bedroom, and master bedroom. New hurricane-impact windows and expansive glass bring the beauty of Siesta Key inside, creating a bright, open, coastal retreat from every angle. This is as close to the sand as it gets—literally beachfront and just steps from the world-famous powdery sand and warm Gulf waters. The elevated second-floor setting gives you the privacy and peace of mind you want, with no past water intrusion or storm damage to the unit, while still offering easy access to the beach and a convenient ramp for luggage. Inside, the condo is move-in ready and designed for easy beach living, featuring tile flooring throughout, an updated kitchen with solid-surface/granite counters, and beautifully updated bathrooms with elegant tiled showers. Whether you are looking for your own Siesta Key escape or an income-producing investment, the flexible 3-night minimum rental policy makes this an outstanding opportunity. Island House offers everything you need for the perfect beach lifestyle, including on-site management, refreshed landscaping, outdoor dining and game areas, beach chairs, chaise lounges, shaded beach cabanas, shuffleboard, cornhole, a heated community pool, and a clubhouse with billiards, foosball, board games, and puzzles. When you are ready to explore, hop on the free trolley or local ride-share vans to Siesta Key Village for shopping, dining, and nightlife, or venture to Turtle Beach, downtown Sarasota, restaurants, boating, fishing charters, performing arts, museums, parks, and the Legacy Trail. This is more than a condo—it is your front-row seat to Siesta Key’s legendary beach lifestyle. Bring your toothbrush, swimsuit, and love for sunsets, because this one is ready to enjoy!

6144 Midnight Pass Road Unit 3N, Sarasota

5169 Oxford Drive, Sarasota
$1,375,000
3 Beds ⋅ 3 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code
WATERFRONT PARADISE!! Welcome to 5169 Oxford Drive, where this elevated, turnkey-furnished home is perfectly positioned on a stunning canal, offering the ideal opportunity for personal enjoyment or rental income. This beautifully maintained property features 3 bedrooms and 3 bathrooms, along with quick access to open water, making it a dream for boating enthusiasts. Start your mornings with a relaxing cup of coffee or tea in your backyard oasis by the private swimming pool. As the day unfolds, gather with family and friends in the warm, inviting living room while enjoying tranquil canal views. The open-concept layout is designed for effortless living, seamlessly connecting to a chef-inspired kitchen just steps away. Upstairs, you’ll find a spacious bedroom and full bathroom, perfect for guests or added privacy. Downstairs features two en-suite bedrooms, providing comfort and convenience for everyone. Step outside to your own private retreat—ideal for entertaining or unwinding. Spend evenings by the pool, fire up the barbecue, or fish right from your private dock and pier. For adventure, grab your paddleboard and head straight out to the Gulf from your backyard. This home showcases exceptional features and thoughtful upgrades throughout, including:     •    Durable steel roof     •    Updated flooring     •    Indoor laundry     •    Outdoor grilling area     •    Private swimming pool     •    Boat slip     •    Private fishing pier Located just moments from Siesta Beach, you can easily hop on your golf cart or enjoy a scenic walk to one of Florida’s most beautiful shorelines. This is more than just a home—it’s a lifestyle. Seller is offering a one-year home warranty with a full-price contract. Schedule your private showing today and experience this exceptional property and neighborhood firsthand.

5169 Oxford Drive, Sarasota

114 Island Circle, Sarasota
$1,375,000
Sarasota Beach SubDv. ⋅ 34242 Zip Code
A rare opportunity to secure a true waterfront estate-sized homesite in the highly sought-after Palm Island enclave of Siesta Key. Located at the end of a quiet loop on Island Circle, this oversized 15,500 square foot pie-shaped double lot offers an exceptional 180+ feet of water frontage, creating a private, expansive setting rarely found this close to the beach. Surrounded by lush natural mangroves and multimillion-dollar residences, this property delivers the perfect balance of privacy, exclusivity, and direct boating access. A standout feature of the property is the grandfathered in 20x24 dock, significantly larger than what current regulations allow. Paired with a 14,000-pound boat lift and existing water and electric connections, for boating enthusiasts, this is not just a convenience, it’s a major asset that cannot be replicated today. This homesite offers a strong foundation for new construction and the opportunity to design and build a custom waterfront estate tailored to your vision. The lot’s unique shape and size allow for a larger footprint, creative architectural design, and maximization of water views. Palm Island is one of Siesta Key’s best kept secrets, an intimate community of fewer than 140 homes known for its quiet streets, limited traffic, and strong sense of privacy and community. The property is ideally positioned across from a small community green space and just minutes from the world-renowned Siesta Key Beach, consistently ranked among the top beaches in the United States. Whether you are looking to build a full-time residence, a seasonal retreat, or a long-term investment property, this lot presents a rare combination of size, location, waterfront access, and redevelopment potential that is becoming increasingly difficult to find on Siesta Key. Opportunities like this are limited, especially with irreplaceable features like this dock and water frontage.

114 Island Circle, Sarasota

306 Beach Road Unit 306, Sarasota
$1,350,000
3 Beds ⋅ 3 Baths ⋅ Shells On Siesta Key SubDv. ⋅ 34242 Zip Code
EXCEPTIONAL WEEKLY RENTAL TOWNHOME JUST STEPS FROM SIESTA KEY VILLAGE! An exceptional opportunity to enjoy a turnkey-furnished, three-bedroom townhome in a highly desirable location on the beach side of the road, just steps from the vibrant atmosphere of Siesta Key Village. With weekly rentals, pet-friendly accommodations, a two-car garage, and gated access to world-renowned Siesta Key Beach, this property offers the perfect combination of personal enjoyment and rental potential. Renters consistently give this residence five-star reviews, praising its convenience, cleanliness, and comfortable accommodations. Summer 2026 rentals have been exceptionally strong, further highlighting the appeal and income potential of this sought after location. The home has been thoughtfully updated, including a newer roof (2020), whole-home re-pipe (2023), hurricane-impact windows (2019), renovated kitchen and baths (2018– 2019), and updated systems and major appliances (2018–2019). Just a couple of blocks away, Siesta Key Village offers an irresistible mix of casual and fine dining, live entertainment, shopping, and the fun-filled island lifestyle that makes Siesta Key so special. Imagine enjoying your own piece of paradise where white crystal-sand beaches, rolling waves, spectacular sunsets, and the energy of the Village are all part of everyday life. Whether you're looking for a vacation retreat, an income-producing investment, or both, this exceptional Siesta Key townhome is truly a dream come true.

306 Beach Road Unit 306, Sarasota

522 Commonwealth Lane, Sarasota
$1,350,000
3 Beds ⋅ 3 Baths ⋅ Siestas Bayside Waterside SubDv. ⋅ 34242 Zip Code
Rare Grand Canal redevelopment opportunity on Siesta Key, offered at land value. This estate-sale homesite delivers approximately 168 feet of water frontage, among the most generous on the Grand Canal, along one of the canal's widest, most open stretches, with long water views and exceptional ease of egress. Boaters enjoy quick passage to the Intracoastal Waterway and on to the Gulf, with the bridge just minutes away. On a peaceful cul-de-sac, the site pairs privacy with proximity, with a short bike ride to the powdery white sand of top-rated Siesta Key Beach. Build anew and capture full water views or renovate to your vision. While the primary value is the exceptional lot, according to the seller, water has not intruded the interior of the existing home. Sold at land value, buyer to perform all due diligence. Opportunities of this width, frontage and location on the Grand Canal are exceedingly rare.

522 Commonwealth Lane, Sarasota

4939 Commonwealth Drive, Sarasota
$1,350,000
3 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
You can bike to the beach from this fully renovated coastal contemporary home in a highly desirable Siesta Key community just minutes from world-famous Siesta Key Beach. Ideal as a primary residence, second home, rental investment, or multigenerational property with private in-law suite. Upstairs offers 2BR/2BA with soaring ceilings, abundant natural light, and open-concept living. Downstairs features a private 1BR/1BA suite with living area, kitchenette, as well as a separate laundry closet—perfect for guests or income potential. Designer finishes throughout, LVT flooring, and a chef’s kitchen with 10’ quartzite waterfall island, custom cabinetry, and premium stainless appliances including Fisher & Paykel refrigerator and GE Profile induction range. The Spacious primary suite with deck/pool access offers a custom walk-in closet and spa-style bath featuring dual vanities, freestanding tub, and separate shower. Updated secondary bath, stacked washer/dryer, and generous storage. Outdoor living shines with Trex-decked patios, oversized screened pool enclosure, travertine pavers, covered lanai, and heated resort-style pool as well as new hot tub. The Custom Siesta Key Mural adds a little fun to the space as well! Fully fenced yard with tropical landscaping for added privacy. Extensive updates include newer roof, electrical, plumbing, AC, pool heater, appliances, Hardie board siding, interior/exterior paint, LED lighting, epoxy-finished garage and paver driveway. Minutes to Siesta Key Village dining, shopping, and beaches. Do not miss your chance to have your Move-in ready coastal retreat -meticulously maintained and designed for effortless Siesta Key living. All measurements are estimates and are approximate. Buyer and/or Buyer agent confirm all info - seller nor agent makes no guarantees

4939 Commonwealth Drive, Sarasota

5341 Siesta Court, Sarasota
$1,350,000
3 Beds ⋅ 2 Baths ⋅ Siesta Cove Sub SubDv. ⋅ 34242 Zip Code
Beautifully updated in 2020 and ideally situated in the coveted Siesta Cove neighborhood, this 3-bedroom, 2-bath pool home captures the essence of relaxed island living with a modern coastal touch. No flood water intrusion or damage during the historic 2024 hurricane season, with all improvements completed by the current owners prior to Hurricanes Helene and Milton. The open, split-bedroom floor plan offers two inviting living spaces filled with natural light and a seamless flow ideal for both entertaining and everyday comfort. The chef’s kitchen, open to the family room, features a spacious island with seating, sleek modern cabinetry, quartz countertops, and designer appliances. The primary suite is generously sized with a walk-in closet, updated bath, and direct access to the screened-in pool and patio—creating a true indoor-outdoor retreat. Outside, the large caged pool and expansive private backyard provide the perfect setting for lounging, dining, and soaking in the Siesta Key lifestyle. Recent updates add peace of mind, including a new roof (2025), impact windows and doors (2025), PVC sewer lines (2021), and a new pool pump (2022). Just minutes from the world-famous Siesta Key Beach and the shops and restaurants of the village. Book your private showing today.

5341 Siesta Court, Sarasota

5880 Midnight Pass Road Unit 403, Sarasota
$1,350,000
2 Beds ⋅ 2 Baths ⋅ Casarina SubDv. ⋅ 34242 Zip Code
Welcome to your Siesta Key retreat, where every day feels like a vacation. Perched above the powdery white sands of Siesta Beach, this beautifully renovated home strikes the perfect balance of comfort, style and convenience. You are bound to be impressed by the impeccable attention to detail throughout this open-concept design which includes porcelain plank flooring, custom doors, plantation shutters, architectural ceiling moldings, recessed lighting, and Restoration Hardware fixtures and hardware. The kitchen is a dream with quartz countertops, a 7 ft. island flanked by waterfall edges, an abundance of white cabinetry, stainless appliances, a wine fridge, a pantry and plenty of closet storage. The breakfast bar has ample room for bar stools and extends into the dining area, creating a perfect environment for casual meals or hosting friends. The beachfront experience continues into the living room and onto the balcony overlooking the pool, beach and gulf. The master suite offers endless gulf views and an exquisite bath that feels like a personal spa featuring floating vanities, under cabinet lighting, designer shower fixtures and separate water closet with a linen closet. The guest bedroom and bath will have your guests planning their next visit before they even leave. And there’s even a laundry room with full size washer and dryer providing the utmost convenience. Casarina is nestled within seven acres of newly planted tropical landscaping and 200 feet of private beach. Spend your days swimming in the heated pool, soaking in the spa, playing a round of tennis, pickleball, basketball, or simply enjoying the quiet beauty of the #1 Siesta Key Beach. With covered parking, a secure lobby, and an on-site manager, everything you need is right here. Plus, you’re close to the shops and restaurants of Siesta Village and only minutes from downtown Sarasota’s arts, dining, and entertainment. Whether full-time or a seasonal escape, this home invites you to live the Siesta Key lifestyle you’ve been dreaming of.

5880 Midnight Pass Road Unit 403, Sarasota

5740 Midnight Pass Road Unit 405, Sarasota
$1,350,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Welcome to Unit 405 in the highly sought-after Building F at Gulf & Bay Club, where breathtaking Gulf views and refined upgrades set the stage for an exceptional Siesta Key lifestyle. This spacious 2-bedroom, 2-bath residence showcases sweeping panoramas of the Gulf of Mexico, perfectly framed by hurricane-impact windows and sliding glass doors that fill the living spaces with natural light and coastal beauty. Inside, you’ll find thoughtful updates throughout, including a recently renovated primary bathroom and elegant porcelain tile floors that flow seamlessly from room to room. The large kitchen is a standout feature, designed for both functionality and entertaining. It boasts granite countertops, abundant cabinet storage with custom drawers, a wine fridge, a double Dacor oven, two sinks, and a charming breakfast nook where you can enjoy your morning coffee. Just outside, Building F features its own clubhouse and a sparkling pool only steps from your door, offering both convenience and a touch of exclusivity to everyday living. As a resident of Gulf & Bay Club, you’ll enjoy an unparalleled array of resort-style amenities on 32 acres of pristine, beautifully landscaped grounds. Spend your days lounging on 800 feet of private, powdery white sand, or take advantage of three heated pools, six tennis courts, six pickleball courts, a basketball court, a racquetball court, and a state-of-the-art fitness center complete with a yoga studio and dry saunas. Two clubhouses provide inviting spaces to gather, with lounges, a library, billiards, and Wi-Fi. Barbecue areas, picnic spots by freshwater lakes, and free EV charging stations make it easy to entertain and unwind. Just beyond the gates, you’re moments away from Siesta Key’s vibrant dining, shopping, and the iconic Sunday Drum Circle. Combining spectacular views, meticulous upgrades, and the unmatched amenities of Gulf & Bay Club, Unit 405 offers a rare opportunity to embrace the very best of coastal living. This is more than a home—it’s a lifestyle you’ll treasure every day.

5740 Midnight Pass Road Unit 405, Sarasota

Ocean Boulevard, Sarasota
$1,350,000
Harmony Sub SubDv. ⋅ 34242 Zip Code
Future Land Use: Residential. Now positioned at market for immediate sale - build your dream home on this waterfront estate homesite. PRICED TO SELL! Recently reduced by $550,000, this 0.58-acre Siesta Key homesite with canal frontage now represents one of the most compelling values on the market! Cleared - .58 acre homesite. Rare Canal-Front Opportunity on Siesta Key – Last Available Raw Land Parcels. Don’t miss the final canal-front parcels on Siesta Key, exclusively offered as a package to one buyer. These gorgeous lots can be kept as individual ¼+ acre parcels or combined into a single ½-acre estate. Build your dream home on the serene, tree-lined canal-front lot and develop the front lot as a revenue-generating rental, guest house, or second home. With separate parcel IDs, the front lot qualifies for a fully independent second home - a rare advantage. Key Features - Two Pre-Reviewed Blueprints: One set of architectural plans for each lot. Prime Location: Just a short walk to Siesta Key’s world-renowned beaches and vibrant Siesta Key Village. Enjoy fine dining, shopping, and entertainment steps away. Boating Paradise: Approximately 2.2 miles (20-minute boat ride) from your private dock to Sarasota Bay. Scenic Views: Lush tree-lined canal views along the east and south property lines create a tranquil backdrop. These lots are priced below market value as a package deal. Siesta Key Lifestyle: Live the Florida dream with boating access to Sarasota Bay’s fine dining and leisure, a stroll to pristine beaches, or a short walk to Siesta Key Village’s restaurants and shops. Conveniently located near Sarasota Bradenton International Airport, St. Armands Circle, Sarasota Memorial Hospital, theaters, and more. Don’t miss this rare opportunity to craft your perfect waterfront estate in one of Sarasota’s most coveted locations. Welcome to paradise on Siesta Key!

Ocean Boulevard, Sarasota

5560 Shadow Lawn Drive, Sarasota
$1,350,000
4 Beds ⋅ 3 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
One of the lowest priced homes on Siesta Key's deep boating water and only 3 blocks to the white quartz sand and aqua Gulf waters! An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this well-maintained residence is ideally positioned just minutes from the powdery white sands of world-famous Siesta Beach and the turquoise waters of the Gulf. Set on an oversized 14,000-square-foot corner lot, this four-bedroom, three-bath home blends comfortable coastal living with everyday functionality in a highly desirable island setting. Designed for effortless entertaining and easy living, the open-concept floor plan centers on a spacious island kitchen with generous seating, a breakfast bar, and abundant workspace, flowing seamlessly into the dining and living areas for gatherings both large and small. A thoughtful split-bedroom layout offers privacy for owners and guests alike. The primary suite enjoys peaceful views of the pool and canal, while a secondary bath doubles conveniently as a pool bath—ideal for indoor-outdoor living. Step outside to the covered, screened lanai and unwind beside the sparkling pool, framed by tranquil water views and gentle coastal breezes. Tucked along a quiet harbor just off the Grand Canal, the setting is ideal for kayaking, paddleboarding, or boating, with frequent sightings of manatees and coastal birds adding to the natural charm. Evenings bring glowing “mango sunsets” nearby, while mornings begin with soft sunrises reflected on the water. Additional highlights include an oversized two-car garage and a concrete tile roof. Ideally located near the shops, dining, and energy of Siesta Village—and just 15 minutes from downtown Sarasota’s vibrant arts and cultural scene—this home presents a compelling opportunity to enjoy the best of island living, whether as a full-time residence or a serene coastal retreat.

5560 Shadow Lawn Drive, Sarasota