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$800,000
4 Beds ⋅ 4 Baths ⋅ Midnight Harbor Sub SubDv. ⋅ 34242 Zip Code
Under contract-accepting backup offers. Prime waterfront rebuild opportunity on Siesta Key. Tear-down structure on property. Selling for land value only. AS IS situation. Investor or builder's dream! High-equity potential in a neighborhood of multi-million dollar luxury estates. The existing home is heavily storm-damaged and is being sold strictly for lot value. While the existing structure has sustained significant damage from two recent hurricanes, the true value lies in the land, the location, and the limitless potential for a custom waterfront estate. AS IS seawall. Bring your architect, your builder, and your vision. Embrace the ultimate coastal lifestyle with this rare blank canvas on world-renowned Siesta Key. Nestled on a highly coveted bayside lot, this property offers breathtaking water views and access. All this just minutes from one of the best beaches in the world. Walk or drive to dinner and shopping. Half a mile south to the Stickney Point Bridge. Twenty minutes from beautiful downtown Sarasota.

7425 Midnight Pass Road, Sarasota
$625,000
2 Beds ⋅ 2 Baths ⋅ Aloha Kai Apts SubDv. ⋅ 34242 Zip Code
Turn-Key Furnished Villa in Aloha Kai – One of Siesta Key's Premier Beachfront Communities! Welcome to your island retreat just steps from world-famous Siesta Key Beach. This beautifully updated 2-bedroom, 1.5-bath villa offers the perfect combination of coastal living, investment potential, and resort-style amenities. Whether you're searching for a seasonal getaway, full-time residence, or income-producing property, this exceptional opportunity checks every box. Thoughtfully updated, the home features a newer metal roof (2020), impact-rated windows and front door, upgraded 200-amp electrical service, a 2023 water heater, and an updated kitchen with modern cabinetry, quality countertops, and newer appliances. Offered turn-key furnished, it's ready for immediate enjoyment or rental. The first floor experienced water intrusion during Hurricane Milton. Following the storm, the owners completed professional remediation, including a fully permitted renovation and independent mold testing with negative results. Documentation is available, providing confidence in the quality of the restoration. Nestled within the lush, tropical grounds of Aloha Kai, residents enjoy private deeded beach access to Siesta Key Beach, a heated Olympic-size swimming pool, clubhouse, shuffleboard courts, beautifully maintained landscaping, and on-site management. The community permits short-term rentals, making this an attractive opportunity for both personal enjoyment and investment income. Ideally located near Siesta Key Village, waterfront dining, shopping, boating, and all that Sarasota has to offer, this is your opportunity to own a move-in-ready beach villa in one of Florida's most desirable coastal communities. Buyer should verify all room dimensions, rental policies, and community regulations with the co-op association and management.

6020 Midnight Pass Road Unit 49, Sarasota
$986,000
1 Beds ⋅ 1 Baths ⋅ Sunset Royale SubDv. ⋅ 34242 Zip Code
**This is the One! Coastal Contemporary Beachside Living!** Fantastic price for this stunning Penthouse-level, 4th-floor residence at Sunset Royale with beautiful unobstructed Gulf-facing views! Enjoy every sunrise and sunset! Ideally positioned just across the street from world-renowned Siesta Key Beach. This truly move-in ready condo has been beautifully renovated throughout, offering a light-filled coastal interior and effortless flow. The kitchen is a true centerpiece, featuring high-end quartz countertops and backsplash, a large waterfall-edge island, solid wood custom cabinetry, and newer appliances (approximately 2 years). The open layout flows seamlessly into the living space with a fantastic accent wall and out to the balcony, where you can enjoy sweeping Beach/Gulf views. Additional highlights include an in-unit washer and dryer, a newer water heater, and a beautifully updated bathroom with a walk-in shower. A thoughtfully designed welcome area inside the unit provides a perfect arrival space with games, guides, and local information. This property also features an owner's storage unit ideal for beach chairs and gear, a designated parking space, and convenient building amenities including garbage chutes on both sides and two on-site grills available at no charge to owners and guests. Cable is included in the HOA fee, and the building features a new roof put on in 2025. Flexible ownership options allow for **7-day rentals or longer**! Rent the property yourself, bring over your preferred property manager or go with on-site management available through Prime Vacations (optional, not required). Whether for personal use or investment, this penthouse residence delivers the ultimate experience in convenience, comfort, and location in the heart of Siesta Key! A short stroll to Siesta Key village and only a few steps out to the beautiful white sandy beach! Reach out today to schedule your own private tour! **Furniture Negotiable**

711 Beach Road Unit 408, Sarasota
$630,000
2 Beds ⋅ 2 Baths ⋅ Turtle Bay SubDv. ⋅ 34242 Zip Code
SDEO

8735 Midnight Pass Road Unit 404B, Sarasota
$545,000
1 Beds ⋅ 1 Baths ⋅ Crescent Royale SubDv. ⋅ 34242 Zip Code
Prime location directly across the street from Siesta Key Public beach has a full Gulf view that enjoys gorgeous sunrises and sunsets! Unit was completely gutted and remodeled with high end finishes, paint, and furniture in 2011. Everything is in excellent condition. This third floor unit in the highly desired Crescent Royale Condominium complex has a screened lanai, assigned covered parking space and storage locker for beach gear. Complex has large heated pool, grills with picnic area, bike parking, shuffleboard, a Clubhouse with pool table, exercise room and bathrooms. One mile to the Village restaurants and shops. This unit is sold turnkey furnished and allows weekly rentals. Use excellent on-site management or DIY on VRBO and AirBNB. Start your revenue stream from day one - ask to see our stunning rental history! Great income producer - $48,622 in 2025

757 Beach Road Unit 308, Sarasota
$1,700,000
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
$1,200,000
5 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Welcome to Old World Siesta Key...this 1940s Bungalow Home was converted approx 40 years ago into a Triplex and a Cottage was added at the rear of the property. Siesta Key is World Renown for it's White Powdery Sand Beaches and is so convenient to the Mainland and all the Attractions Sarasota has to offer such as the Arts, St Armands and Unbelievable Shopping. The Property is located approximately three blocks behind Siesta Key Village, the Hub of Restaurants, Nightlife, and Shops, and there you will find this Graceful Triplex and Cottage. There are several Private Patios as well as Open Areas for Outdoor Entertainment and Relaxation both in the Front and Rear of the Triplex. There are Storage Units for Each Rental and there is a Shared Laundry Area in the middle of the Backyard. Convenience is really key for this Property as you can Walk to the Beach or the Village in 15 Minutes. Island Life is Unique, Exciting, Colorful but can also be Quiet and Slow, it's the perspective of the Offering and it's a sought after way of living. For the past 20 years the units have been long term rentals. Some of the tenants have been there for years and all four would like to stay and continue their Florida Island Lifestyle. Rents shown are the Expected rents that could be charged as the Owner currently charges less... just his way of doing business. There is one option that could change the dynamics and that would be to keep the Triplex as long term rentals and use the rear Cottage as an AirBNB and Owners Use unit. This would drastically change the income stream. The water and internet/cable is currently paid for by the Owner and the Electric is split between the Tenants based on unit size, of course all of this is subject to change based on the New Owner's intentions. This is an Amazing Opportunity to have both Income and Personal Enjoyment all wrapped up with a Special Place we call Siesta Key Living!

618 Avenida De Mayo, Sarasota
$1,550,000
5 Beds ⋅ 4 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
Set along the Grand Canal on the North End of Siesta Key, 557 Venice Lane presents a rare opportunity to own a waterfront residence that balances architectural character, boating access, and an unmistakable sense of place. Distinguished by one of the few remaining historic boathouses on Siesta Key, the property reflects a legacy of island living that is increasingly difficult to find. Designed for those who value both water and proximity to shore, the home offers direct, protected canal access. From the private dock, boaters follow the Grand Canal into Sarasota Bay, with seamless connectivity to the Intracoastal Waterway and Gulf access beyond. The route is calm, navigable, and ideal for daily use—whether launching a boat, paddleboard, kayak, or jet ski. For beach enthusiasts, Siesta Key’s renowned shoreline is only minutes away, allowing owners to move effortlessly between open water and sand. Interiors are thoughtfully composed, with generous scale and abundant natural light. The main living level is anchored by a refined family room with a marble fireplace, opening into a flexible dining and gathering space suitable for both entertaining and daily living. The expansive eat-in kitchen is complemented by an adjoining lounge area, creating a cohesive environment that feels open yet intentional. The residence includes four well-proportioned bedrooms, each featuring custom closet systems. A junior ensuite primary bedroom on the main living level offers convenience and privacy, while the third-level primary suite is positioned as a true retreat, complete with a sitting area, ensuite bath, and French doors leading to rooftop views over the surrounding neighborhood and waterways. The first floor features a bonus room, ideal for a media space, private office, fitness studio, or guest retreat—adding versatility without compromising the home’s flow. Outdoor living is discreetly private, with a screened pool and lanai framed by mature tropical landscaping. The setting encourages quiet relaxation as well as casual waterfront entertaining, with the dock and boathouse extending the living experience directly onto the canal. With immediate access to Sarasota Bay, nearby beaches, dining, and shopping, the location supports an effortless island lifestyle. The absence of deed restrictions or a neighborhood association further enhances flexibility, making the property suitable as a primary residence, second home, or investment opportunity. 557 Venice Lane stands as a refined waterfront offering, defined by heritage, access, and understated elegance—on one of Siesta Key’s most desirable canals.

557 Venice Lane, Sarasota
$718,000
2 Beds ⋅ 2 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
RARE SIESTA KEY INVESTMENT OPPORTUNITY — just one street back from the water and a 2-minute walk to the beach. This single-family 2BR/2BA rehab property sits on an OVERSIZED .28 ACRE LOT spanning over two different lots on a private dead-end street with only three homes, surrounded by dense, mature vegetation—an exceptionally rare combination of privacy, size, and location. The home has been fully gutted and is being sold AS-IS, creating a true blank slate for investors, builders, or end users seeking to add value. Hurricane damage has been remediated, and the property is ready for redevelopment or renovation. Existing structure offers an open-concept layout with two expansive common areas, ideal for reconfiguration or high-end finishes. Terrazzo floors throughout most rooms may be restored to their original shine, preserving classic Florida character. Outdoor features include a pergola-covered back porch, ample yard space, and a private irrigation well, while still serviced by city water. Opportunities like this—walkable to the beach, oversized lot, ultra-low traffic street, and significant upside—are increasingly rare on Siesta Key. Ideal for flip, rebuild, or long-term hold in one of Florida’s most desirable coastal markets.

129 Pierson Lane, Sarasota
$760,000
2 Beds ⋅ 2 Baths ⋅ Palm Bay Club SubDv. ⋅ 34242 Zip Code
Under contract-accepting backup offers. Looking for the perfect 2-bedroom, 2-bath investment beach condo on Siesta Key? This second-level residence presents a strong income-producing opportunity at the desirable, gulf-front Palm Bay Club. Ideally situated on the beach side of Midnight Pass Road, unit #158 features a comfortable coastal design with an open floor plan, beachy ambiance, and tile flooring throughout, making it move-in ready for owners, guests, and short-term renters alike. Just steps from the pristine blue waters and powder-white sands of Siesta Beach, the thoughtfully designed and tastefully furnished interior maximizes space and functionality with seamless flow from the kitchen to dining and living areas. One of the premier beach-to-bay communities on Siesta Key, Palm Bay Club offers an exceptional array of amenities including two heated swimming pools, a hot tub overlooking the bay, fitness center, lighted tennis court with two pickleball courts, BBQ grills, a fishing pier, and boat docks available for daily rental. With a rare three-night minimum rental policy on Siesta Key and onsite management, this is an outstanding opportunity for the savvy owner-investor seeking both lifestyle and income.

5968 Midnight Pass Road Unit 158, 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
$869,000
2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code
Everything is brand new in this beautifully renovated, turnkey furnished two bedroom, two bath end-unit villa offering an exceptional Siesta Key beach lifestyle just steps from the Gulf. The desirable split floor plan features spacious bedrooms, generous closets, and an open-concept living area filled with natural light, enhanced by a sun-lit Florida room. The updated kitchen is thoughtfully designed with granite countertops, a coordinating backsplash, soft-close cabinetry, and new stainless steel appliances. The primary suite offers a wall-to-wall closet, transom window, and sliding glass doors opening to the Florida room. Additional highlights include luxury vinyl plank flooring, all-new furnishings, and an attached one-car garage with washer and dryer plus ample storage for beach gear. Whether enjoyed as a private coastal retreat or a lock-and-leave rental opportunity, this residence truly offers the best of both worlds. Crystal Sands is a well-managed, financially stable beachfront community that has remained highly desirable since 1969 due to consistent upkeep and thoughtful renovations. The condominium comprises a collection of one, two, and three bedroom villas along with a Gulf-front high-rise tower, all set within beautifully maintained grounds. Residents and guests enjoy private beach access with umbrellas and loungers, two heated swimming pools, a clubhouse, on-site rental management, and night security, all just moments from Siesta Key’s renowned dining and shopping.

6300 Midnight Pass Road Unit 21, Sarasota
$995,000
3 Beds ⋅ 2 Baths ⋅ Siesta Isles SubDv. ⋅ 34242 Zip Code
Endless possibilities just two blocks from Siesta Beach! Whether you're looking to remodel the structure or build a new island retreat, opportunity awaits. A prime 12,229-square-foot property in sought-after community of Siesta Isles, just two blocks from the powdery white sands of Siesta Beach, ranked the #1 beach in the USA. This property offers a rare chance to create your dream home in one of Sarasota’s desirable beach neighborhoods. Offering a clean slate for visionary design to renovate or build new. The generous size of the property and ideal location make it ideally suited for a luxury custom home with room for a pool, tropical landscaping and seamless indoor-outdoor living. Enjoy beach access just .2 miles away, or go less than a mile to Siesta Village, where eclectic shops, lively dining and local entertainment await. From morning experiences along the shoreline to breathtaking sunsets over the Gulf, every day on Siesta Key feels like a vacation. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including the Ringling Museum, Van Wezel Performing Arts Hall, St. Armands Circle and ever-popular Sarasota Farmers Market. Unlock the potential to create a one-of-a-kind island residence just moments from world-renowned Siesta Beach.

734 Canal Road, Sarasota
$639,900
2 Beds ⋅ 2 Baths ⋅ Siesta SubDv. ⋅ 34242 Zip Code
Reduced over 60K! Excellent resort investment opportunity with a proven rental history at The Beach Club on Siesta Key, located just steps from the world-famous sugar-sand beach. This beautifully maintained residence looks and feels brand new, featuring a functional floor plan, deeded beach access, and a complete 2021 update with elegant sea-inspired décor, flat-screen TVs, free Wi-Fi, and a full kitchen with stainless steel appliances. Owners enjoy up to 120 days of personal use per year while benefiting from professional on-site management or the option to self-manage for added flexibility. TripAdvisor rates the property 4.5 stars with outstanding reviews. Resort amenities include a heated pool, hot tub, and complimentary beach chairs and umbrellas. Built in 2009 on stem walls, the building is elevated and sustained no storm damage. Ideally located mid-island just 1,000 feet south of the Stickney Point Bridge for easy mainland access, and within walking distance to popular restaurants, shops, marinas, rentals, and local favorites such as Captain Curt’s and Daiquiri Deck—making this a true turnkey beach getaway and income-producing investment. Ask your agent for the Rental History attached to the MLS listing too!

6732 Sarasea Circle Unit 104C, Sarasota
$4,995,000
6 Beds ⋅ 5 Baths ⋅ Sarasota By The Sea SubDv. ⋅ 34242 Zip Code
Repriced to the market - reduced $250,000! An exceptional opportunity to own two stunning residences in one offering, near the powdery white sands of world-renowned Crescent Beach. Beach House Residences #301 and the Penthouse together create a rare, turnkey coastal retreat where modern elegance and relaxed island living exist in harmony. Offered fully furnished and move-in ready, this one-of-a-kind, two-level residence presents exceptional flexibility to embrace the ultimate Siesta Key lifestyle. Suited as a full-time or seasonal residence, a multi-generational family retreat, or a flexible ownership opportunity with the ability to enjoy or utilize one floor while renting another, short or long-term. Spanning the top two floors, this unique offering includes six generously sized bedrooms and five full baths (a four-bedroom, three-bath residence plus a two-bedroom, two-bath penthouse), thoughtfully designed to accommodate family and guests with ease. Expansive open floor plans welcome you with immediate Gulf views, while floor-to-ceiling glass and spacious balconies offer coastal breezes and blazing sunsets. Chef’s kitchens on each level are beautifully appointed to host unforgettable gatherings or intimate dinners, blending function with refined coastal style. Each residence enjoys its own private, secured entry, access to a state-of-the-art elevator, full kitchens, laundry rooms, luxury countertops, soft-close wood cabinetry, upscale lighting and designer fixtures. Additional highlights include spa-inspired baths, plush furnishings, 10-foot ceilings, spacious closets, a secure lobby, a private two-car garage and a hot tub on the penthouse-level balcony. Chic contemporary architecture enhances the building’s coastal presence, while sweeping Gulf and sunset views create a sense of escape. A private pet run oasis adds a thoughtful touch for four-legged companions. Outdoor living is equally inviting and as a member of the community association, residents enjoy access to the pool and private beach entry, offering a seamless connection to the Gulf. Ideally within a half block of Siesta Key’s vibrant South Village, you are moments from beloved restaurants, cafés, tiki bars, boutiques, rentals and everyday conveniences. Complimentary trolley service provides easy access to Siesta Village, evoking the charm of a relaxed island-style experience, while quick access to the Stickney Point Bridge allows effortless travel on and off the island. With its prime beach-block location, thoughtful design and rare dual-residence configuration, this is a coastal offering that feels timeless and irreplaceable, an opportunity to create lasting memories on one of Florida’s celebrated shorelines.

1140 Seaside Drive Unit 301 & Penthouse, Siesta Key
$900,000
1 Beds ⋅ 1 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code
This fully updated spacious and open condominium located on Siesta Key boasts incredible views of the Gulf of America and Siesta Key Village. Enjoy them one of your three private balconies! An abundance of bright natural light flows throughout the unit. With its private beach access, pool area, common area, and close proximity to the Siesta Key Village, this unit offers an abundance of lifestyle.

5400 Ocean Boulevard Unit 8-04, Sarasota
$452,000
1 Beds ⋅ 1 Baths ⋅ Holiday Apts SubDv. ⋅ 34242 Zip Code
Welcome to Gulf Holiday Condominium—an exceptional opportunity to own one of just 18 units in this rarely available community. This beautifully updated second-floor, 1-bedroom, 1-bath residence places you just steps from the best of what Sarasota has to offer. Inside, you’ll find stainless steel appliances, quartz and granite countertops, and modern finishes throughout, creating a bright and inviting retreat ideal for personal enjoyment or vacation rental income. If rental income is a priority, you’ll appreciate that this area allows for one-week rentals—a rarity in the surrounding communities. Gulf Holiday Condominium boasts an unbeatable location with effortless access to the white quartz sands of Siesta Key Beach and the vibrant shops, dining, and entertainment of Siesta Key Village. Opportunities like this are truly seldom available—don’t miss your chance to own a piece of paradise and proudly tell your family and friends, “I live where you vacation!

73 Avenida Messina Unit 15, Sarasota
$2,395,000
3 Beds ⋅ 2 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
The Fastest Open-Water Access Available on Siesta Key Under $2.5 Million Less than 3 minutes to Sarasota Bay, 95 feet of waterfront, and a 75 x 3 of dock designed for serious boating enthusiasts. If you’ve been searching for a waterfront home that prioritizes boating convenience over lengthy canal runs, this is one of the most compelling opportunities currently available on Siesta Key. Why spend 30–45 minutes idling through canals when you can be in Sarasota Bay in under 3 minutes? Positioned on one of Siesta Key’s premier deep-water canals, this exceptional waterfront residence offers the rare combination of protected dockage and near-immediate access to open water. For boaters who value time on the water, this location is difficult to replicate at any price point. Designed with larger vessels in mind, the property features approximately 95 feet of waterfront, a 75-foot dock, 200-amp dock service, and four 50-amp shore power connections. Whether you’re heading offshore, cruising the Intracoastal, or enjoying a sunset cruise across Sarasota Bay, this home delivers a level of boating convenience that few waterfront properties can match. Boater Highlights?• Less than 3 minutes to Sarasota Bay?• Approximately 95 feet of waterfront?• 75-foot dock?• Four 50-amp shore power connections?• 200-amp dock service?• Deep-water canal location?• Protected dockage with quick open-water access Inside, the home has been thoughtfully renovated with a clean coastal-modern design featuring designer tile flooring, an open-concept floor plan, Viking gas appliances, custom cabinetry, and expansive waterfront views. The spacious living areas flow seamlessly into the kitchen and entertaining spaces, creating an ideal environment for both everyday living and hosting guests. The private primary suite serves as a luxurious retreat, complete with an oversized walk-in closet, spa-inspired bathroom, glass-enclosed shower, and direct outdoor access. An additional flexible space offers the opportunity to create a fourth bedroom, private guest suite, office, or media room. Outdoor living is centered around the waterfront lifestyle. Enjoy a saltwater pool and spa, tropical landscaping, integrated lighting, retractable awning, propane fire pit, outdoor shower, and multiple seating and entertaining areas overlooking the canal. Additional features include a 13.5 kW generator, hurricane protection, epoxy-finished garage, updated HVAC system, newer water heater with circulation system, 250-gallon propane tank, and valuable dry storage space. Originally introduced at $2,690,000 and now offered at $2,450,000, this property represents one of the strongest values currently available for buyers seeking deep-water dockage, exceptional boating access, and luxury waterfront living on Siesta Key. Luxury yacht available separately.

4508 Woodside Road, Sarasota
$989,000
3 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code
Owner Financing Available ~ Siesta Key ~ Siesta Key Beach - Private Beach Access ~ Gulf & Bay Bayside Community ~ Three Bedrooms ~ Two Bathrooms ~ Weekly Rental Property ~ Two Pools / Sauna's ~ Tennis ~ Pickleball ~ Day Dock ~ Garage (Deeded).This bright and serene two-story unit offers a welcoming second-floor entrance and is conveniently located just a short distance from the beach, making it truly move-in ready. As a weekly rental property, it is completely turn-key and situated within the desirable Gulf & Bayside Community. The residence features updates throughout and boasts an excellent layout designed for both comfort and style. Main Level Features: Upon entering, you are greeted by a light-filled kitchen equipped with a vaulted breakfast nook, stainless steel appliances, and a breakfast bar. The kitchen seamlessly flows into the dining room, which is enhanced by a wet bar and a beverage refrigerator, perfect for entertaining. The spacious living room, with its inviting vaulted ceiling, provides an ideal setting for gatherings and relaxation. The first-floor primary bedroom includes an ensuite bathroom that also serves as the guest bathroom. From here, you have access to the screened lanai, creating a seamless indoor-outdoor living experience. Tile flooring extends throughout the main level, except for the staircase leading to the upper floor. Upper Level and Additional Spaces: Upstairs, the home features a bright, multi-use loft area, as well as two luminous guest bedrooms. Each bedroom is complemented by a private Juliet balcony, and they share a bathroom with an enclosed shower. Additional conveniences include an in-unit stackable washer and dryer and a deeded, private one-car garage. Community Amenities: Residents of this community enjoy access to a variety of amenities, including private beach access, two pools, a sauna, a day dock, barbecue grills, tennis and pickleball courts, and a clubhouse. The property is beautifully showcased in photos and a drone virtual tour, inviting you to come and experience all it has to deliver. This is a weekly rental community, the management of which is at the discretion of the owner. Use the onsite management or one of your choosing. Easy to show even during active tenant stays.

1225 Siesta Bayside Drive Unit 1225B, Sarasota
$625,000
2 Beds ⋅ 2 Baths ⋅ Island House SubDv. ⋅ 34242 Zip Code
Your dream Beachside villa is here. Smartly appointed with updated bathrooms and kitchen. Turn key furnished! Carport. Weekly rental can provide income for the owner. On-site manager. Island house is a superbly maintained complex featuring two beach cabanas, a beach, rinsing station, beach, chairs, a large heated, swimming pool, shuffleboard with a view, a game room, two gas grills available to all and a beachfront courtyard where you will experience the most amazing sunsets. Ride the free trolley to Siesta Key village for Dining shopping and entertainment.

6150 Midnight Pass Road Unit 13, Sarasota
$762,000
3 Beds ⋅ 3 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
POOL HOME!! Priced To Sell!! Nestled on the peaceful tranquil island of Siesta Key, renowned for its world-class beach and romantic sunsets. JUST MINUTES FROM Siesta Beach & Village. This is the most wonderful place to embrace island-style living. This north island location on a quiet canopy street is walkable to the village, beach, and renowned Out-of-Door Academy. This 3 Bedroom and 2 & 1/2 Bathroom home is ready for your personal touches. Enjoy relaxing in your Caged Pool & Patio area. This Single family home has approximately 1834 sq.ft. +/- living area and a 2 car garage. The existing home—professionally remediated after flood damage—presents a unique opportunity for those looking to reimagine or completely rebuild. Almost 13,000 sq.ft lot with luscious natural landscaping and mature oaks. Updated roof in late 2019.

4894 Oxford Drive, Sarasota
$575,000
1 Beds ⋅ 1 Baths ⋅ Beach Club At Siesta Key SubDv. ⋅ 34242 Zip Code
Welcome to Beach Club at Siesta Key, where an unbeatable investment opportunity awaits just steps from the world-renowned Siesta Key Beach. This charming 1-bedroom, 1-bathroom first-floor condo is the ideal blend of personal escape and income-generating property, boasting a successful history in short-term rentals. As you step inside this fully furnished, turnkey unit, you’re greeted by an open living area is perfect for relaxation, featuring a TV for entertainment, while the kitchen comes equipped with stainless steel appliances. An in-unit washer and dryer add to the convenience, making longer stays comfortable and stress-free. The on-site professional management team handles all the details, from bookings to maintenance, giving owners peace of mind and ensuring that guests have a seamless experience. The property offers desirable amenities, including a heated pool, a soothing hot tub, complimentary Wi-Fi, and beach chairs and umbrellas for enjoying sun-soaked days by the ocean. Positioned mid-island and close to the Stickney Point Bridge, this condo provides easy access to all that Siesta Key has to offer. The Beach Club at Siesta Key is a hidden gem that is perfectly located within walking distance of South Siesta Village, Crescent Market, and local favorites for ice cream, coffee, dining, and more.

1020 Sun And Sea Drive Unit 102, 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
$1,996,000
3 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Pre-construction. To be built. Custom beach home opportunity! Less than a mile to the #1 Rated Beach in the Nation- Siesta Beach! Almost 1/4 acre lot in a charming neighborhood with close proximity to public beach and Village. The existing structure is a tear down, leaving a beautiful canvas to create your dream home or investment property! Optional Island Series plans by Yoder Custom Homes are available, or choose the builder of your choice, or land only. Just 6.4 mi to downtown Sarasota- known for it's Arts & Culture. Call today for more information! Land only listed in vacant land.

643 Calle De Peru, Sarasota
$775,000
4 Beds ⋅ 3 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
Exceptional redevelopment opportunity in Bay Isles on Siesta Key—where short-term rentals are permitted! The current home experienced water intrusion and damage during recent storms. This property is being sold for land value only. This generously sized parcel is two lots totaling 16,200 square feet (.37 acres), 90 ft of frontage and 181 feet deep. The lot spans the entire block from Anglin Dr to Flamingo Dr along Siesta Dr. No other residence backs up to it. This offering is an ideal canvas for a sizable custom home, pool, and pool-home. Whether you're a builder looking to create a luxury island residence or an investor eyeing short-term rental potential, this location delivers. In a quiet, established neighborhood, just a short distance from Siesta Key Beach and Siesta Village. Easy access to the mainland via the north bridge. A true strategic build site on Siesta Key.

3480 Anglin Drive, Sarasota
$1,000,000
3 Beds ⋅ 3 Baths ⋅ Harmony Sub SubDv. ⋅ 34242 Zip Code
Opportunity Awaits on this .37 of an acre (approximate dimensions 100' x 158') on Siesta Key with Western Exposure. The existing structure is ready to be removed and a new home would be best suited for this great lot. Current structure features 3BR/3BA with a pool ~ but the home did suffer severe water damage and is now being "sold as is" for lot value only. This nice, oversized lot has a great location ~ just a short bike ride to Siesta Village.

4920 Higel Avenue, Sarasota
$995,000
2 Beds ⋅ 2 Baths ⋅ Crescent Arms SubDv. ⋅ 34242 Zip Code
Coastal Luxury Villa with Thai-Inspired Elegance Now Offered at $995,000 Experience the best of Siesta Key living in this beautifully renovated two-bedroom, two-bath villa located in the highly sought-after, gated beachfront community of Crescent Arms. Now priced at $995,000, this is a compelling opportunity recently adjusted from $1,075,000 to reflect today’s market and create immediate value. This thoughtfully updated residence blends custom coastal finishes with subtle Thai-inspired design, creating a warm, serene atmosphere throughout. The open-concept layout offers seamless flow between the kitchen, dining, and living areas ideal for both everyday living and entertaining. The gourmet kitchen features quartz countertops, stainless steel appliances, and generous workspace, all opening into a bright and inviting living area. Both bathrooms have been tastefully updated with spa-like finishes, including a walk-in shower and modern fixtures. Step outside to your private patio perfect for relaxing, grilling, or enjoying the tropical surroundings just moments from the beach. Crescent Arms offers exclusive private beach access to world-famous Siesta Key Beach, along with onsite management making this an excellent option for personal use, vacation rental income, or a combination of both. This property has a proven rental history with strong year-round bookings. Whether you’re searching for a coastal retreat, investment opportunity, or both, this villa delivers location, lifestyle, and value. Sold turnkey move right in or start generating income immediately.

6308 Midnight Pass Road Unit 6, Sarasota
$975,000
3 Beds ⋅ 3 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
Price Improvement! Don’t Miss This Waterside East Gem in Siesta Key! Amazing opportunity to own a pool home with a seawall and dock—ready for your creative vision. Whether you choose to renovate and update the existing home or build a brand-new waterfront retreat, this location is unmatched. Tucked away on a peaceful cul-de-sac just off the Grand Canal, the home features: • Large circular driveway for easy access and ample parking • Open floor plan with split-bedroom layout for added privacy • Sparkling pool just resurfaced with brand-new equipment installed • Private dock with direct water access for boating and water activities While the home is in need of some updates, the potential here is incredible—whether as an investment property or your dream residence. All this, just minutes from world-class beaches, shopping, dining, and entertainment. Property is being sold As-Is—buyer to verify all information.

568 Venice Lane, Sarasota
$685,000
3 Beds ⋅ 2 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
Beautiful Siesta Key location

630 Venice Lane, Sarasota
$900,000
3 Beds ⋅ 4 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. Seller may consider buyer concessions if made in an offer | BEACH VIBES? Check, PRIME LOCATION? Check, HIGH END RENOVATIONS all completed in 2025? Check, check & check! Welcome to the ultimate in Florida living – whether you are looking to settle in full time or score an amazing SHORT TERM RENTAL/VACATION HOME, this one is a MUST SEE! Located in the heart of Siesta Key, this single story POOL HOME puts you just a 10 minute stroll to Siesta Key Village, and 5 minutes past that you are on the powdery sands of the world-famous beach. Nestled in a quiet, tree lined, no HOA community, you are living large with easy access to US-41, SR-72, and I-75. It’s the best of laid back island living with every modern convenience at your fingertips! Looking for CURB APPEAL? It’s through the ROOF (which was replaced in 2020)! With lush tropical landscaping, a circular paver driveway, covered portico, and an EV CHARGING STATION, the tone is set before you ever step inside. The covered front entry features a charming glass-inset front door that opens into an adorable foyer with immediate beach house energy. Inside you will find porcelain WOOD LOOK TILE FLOORS throughout and a living area full of personality – think vaulted TONGUE & GROOVE WOOD SLAT/BEAM CEILINGS, a cozy WOOD BURNING FIREPLACE, and CUSTOM BUILT-INS! You will appreciate the seamless flow into the light filled dining area, where sliding glass doors paired with a large window connects the interior to your outdoor oasis and includes a built-in bar and extra storage. The kitchen is a showstopper – a 2025 renovation with on trend TWO-TONE CABINETRY, stylish TILED BACKSPLASH set in a modern herringbone pattern, sleek QUARTZ COUNTERTOPS, STAINLESS STEEL APPLIANCES, and a window over the sink so you don’t miss a second of the party outside. Enjoy idyllic indoor/outdoor living with a COVERED LANAI and the recently resurfaced SALT WATER POOL, complete with ceiling fans and new screens in the enclosure for maximum comfort, and convenient outdoor/pool bath access. The fenced backyard is both low maintenance and private – perfect for soaking up the Siesta Key sunshine! Last but certainly not least, your PRIMARY SUITE is a peaceful hideaway with a huge WALK-IN CLOSET, French door access to the lanai, and a spa-like en-suite bath featuring DUAL SINKS under LIGHTED MIRRORS, and a custom tiled walk-in shower behind seamless glass. Need space for guests, a home office or additional rental potential? The PRIVATE MOTHER-IN-LAW-SUITE is a game changer - delivering its own entrance off the pool area for endless versatility with additional pavered parking close by. Also take note of the NEWER A/C, UPDATED PLUMBING & WATER HEATER (2025), partial ELECTRICAL UPDATES, IMPACT GLASS/DOUBLE PANE STORM WINDOWS (most under 5 years old), and extra storage cabinets in the garage – to sum up Saint Albans Ave… The vibe? Fresh, modern and full of character! The location? Out of this world! The lifestyle? Pure Siesta Key magic! Call today!

5108 Saint Albans Avenue, Siesta Key