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$460,000
2 Beds ⋅ 2 Baths ⋅ Anchorage SubDv. ⋅ 34242 Zip Code
***PROJECTED GROSS REVENUE UPWARDS OF 45,000 PER YEAR***Experience the best of Siesta Key living in this light-filled, south-facing 2-bedroom, 2-bath condo at The Anchorage on Siesta Key. This spacious unit features a large, private balcony with tranquil views of the canal and Intracoastal Waterway, buffered by lush mangroves for added privacy. Enjoy balcony access directly from the main bedroom a perfect spot for morning coffee or evening sunsets. The second bedroom also features an ensuite bathroom, offering comfort and privacy for guests or family. Offered fully turnkey furnished just bring your suitcase and move right in! Stylish new furniture from 2024 complements the open layout, while recent updates include fresh interior paint and durable life-proof flooring in the primary bedroom. Additional upgrades such as a newer water heater installed in 2020. Originally remodeled in 2010, the condo seamlessly blends modern convenience with timeless coastal charm. Enjoy deeded private beach access to the world-renowned #1-rated Siesta Key Beach, just a short stroll across the street. The Anchorage is a highly desirable waterfront community offering resort-style amenities: a heated Olympic-size pool, fitness center, his-and-hers saunas, lighted tennis court, two pickleball courts, BBQ grills, shuffleboard, and beautifully maintained gardens along the water. Boating enthusiasts will appreciate the first-come, first-served boat slips with direct Intracoastal access, available to owners for just $10/month. Perfect for both personal use and investment, this property allows weekly rentals year-round (1-week minimum), offering excellent income potential. The on-site professional management team makes ownership and guest rentals effortless. Additional features include an elevator in the building, ample parking, and a secure, welcoming community environment. Ideally located near the Stickney Point Bridge for easy access to the mainland, and just minutes from shops, restaurants, Siesta Key Village, and downtown Sarasota’s vibrant arts and culture scene. Whether you're seeking a full-time residence, seasonal retreat, or high-performing rental property, this condo delivers the best of coastal living on Siesta Key.

6415 Midnight Pass Road Unit 205, Sarasota
$1,450,000
3 Beds ⋅ 3 Baths ⋅ Shells On Siesta Key SubDv. ⋅ 34242 Zip Code
The stunning three-bedroom, two-bathroom Spanish-style villa stands as a testament to resilience and quality. Experience peace of mind knowing this beautiful home endured no storm damage, standing high and dry with top-notch construction that allowed for zero impact from recent storms. Purchase with confidence, as this beachside sanctuary continues to shine. Nestled on a serene, private lane just off Beach Road, this enchanting villa offers unparalleled access to Sista Key Beach, with no roads to cross before your toes touch the soft, white sands and tranquil Gulf waters. Recent updates include a newer roof and air conditioning system, ensuring modern comfort for years to come. With its elegant Mediterranean charm and modern touches, the home invites you through a private gate and features luxurious glazed Spanish tile flooring, beautiful curved archways, and timeless bathroom accents. The villa boasts a a spacious layout with natural light flowing through every room, creating a warm and welcoming atmosphere. The thoughtful design includes an elevator for easy access across the levels and a charming open air terrace off the dining room, perfect for enjoying Florida's gentle breezes. A garden entry provides additional character, while partial Gulf views from the bedroom allow you to wake up to serene, coastal views every day. Parking is convenient with a spacious garage for tandem parking, complementing the vill's many desirable features. The low HOA fees (just $125 per month) and the flexibility of using the villa as a private residence or a desirable rental make this property a rare find. Plus, access to a pool is available if managed by Beachside Management. Don't miss the opportunity to own this elegant Mediterranean villa, perfectly positioned for beachside living on Siesta Key. Whether as a primary residence or investment, this property promises a life of luxury, tranquility, and unmatched Gulf-side beauty.

221 Tenacity Lane, Sarasota
$2,590,000
4 Beds ⋅ 4 Baths ⋅ Bay Island SubDv. ⋅ 34242 Zip Code
A Rare Opportunity on North Siesta Key with exceptional weekly income, prime location 350 Feet of Waterfront! Discover this unique multi-family income producing single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—with easy fast access to the bay and Big Pass it is truly a boater’s and fisherman’s paradise. Just a few steps to Shell Beach and its breathtaking sunsets, minutes from the world famous Siesta Beach, Siesta Village with restaurants, shopping, nightlife, quick access to downtown, and St. Armands Circle. You have it all! The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom guest house. Whether you choose to renovate, rebuild, or divide the lot (buyers to verify with the City), the possibilities are endless with this property!

300 Garden Lane, Sarasota
$1,100,000
2 Beds ⋅ 2 Baths ⋅ Terrace SubDv. ⋅ 34242 Zip Code
Virtually Staged. Virtually Staged. MAJOR PRICE REDUCTION! The lowest-priced 2-bedroom residence at Beach Terrace in over 8 years—this is the opportunity of the decade! Welcome to one of Siesta Key's most desirable addresses. This exceptional corner residence offers direct Gulf of Mexico frontage, perfectly positioned at the end of the village where luxury meets convenience. Prepare to be captivated by panoramic vistas from your three spacious private balconies. Enjoy unobstructed views of pristine white sand beaches, sparkling aqua Gulf waters, downtown Sarasota's skyline, and even Longboat Key on clear days. Watch the twinkling lights of Siesta Key Village create an unforgettable backdrop as the sun sets—easily among the best views on Siesta Key. Enter through an inviting foyer with elegant tiled flooring leading into a beautifully updated kitchen featuring granite countertops & modern cabinetry. The spacious living area showcases dual sliding glass doors framing stunning Gulf views. The generous dining area provides ample space for entertaining. The primary bedroom features a private Gulf-view balcony with two full-size beds and an elegant ensuite bath with updated tile, modern cabinetry, and granite countertops. The guest bedroom offers a full bed and private sliding door to dazzling Gulf views, plus an updated full bathroom with modern finishes and tile shower. Elevated heated saltwater pool with sunset views, modern fitness center, community room, covered parking, and gated security with onsite management. Private beach access puts you steps from world-renowned Siesta Key Beach. Nestled at the end of the village, enjoy tranquility and convenient access to Siesta Key Village shops and restaurants—no car needed once you arrive. Beach Terrace represents the pinnacle of Gulf-front living. With the lowest pricing for a 2-bedroom in over 8 years, this move-in ready split-floor plan residence is your once-in-a-decade opportunity to own paradise where stunning views, luxury amenities, and coastal elegance unite.

5400 Ocean Boulevard Unit 6-4, Sarasota
$474,000
1 Beds ⋅ 1 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code
Elevated Living on the 4th Floor! Discover this well appointed 1-bedroom, 1-bath condo just minutes from the world-renowned Siesta Key Beach. This TURN KEY residence offers the ideal blend of relaxed Florida living and exceptional value. Step into a bright and airy space where natural light pours into the east-facing screened balcony, overlooking lush tropical landscaping. The interior features ceramic tile flooring throughout the kitchen, dining, and living areas, creating a clean and cohesive look. The kitchen is equipped with stainless steel appliances, including a range and dishwasher, and boasts a generous walk-in pantry for all your storage needs. A separate large closet provides ample space for beach and pool gear. Residents and guests enjoy access to a host of amenities including a community pool, tennis courts, social room, and fishing pier. Recent updates include a brand-new water heater and a newer A/C system for added peace of mind. Best of all, this gem allows for weekly rentals, offering a fantastic opportunity to offset ownership costs. Gross rental income ranging from $30,000 to $40,000 annually. Great place to vacation when you can...and rent when you can't! The unit includes one assigned covered parking space, plus plenty of guest parking. Don’t miss out—schedule your showing today!

6157 Midnight Pass Road Unit E24, Sarasota
$2,075,000
4 Beds ⋅ 4 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
This newer construction home is perfect for year-round living or as a beach retreat. Additionally, it has made nearly $100,000.00 in rental income. Its design and amenities are exceptional as is it’s versatility! The elevator extends from the street level 3+ car garages to the main living floor and the upper floor. You are greeted on the main floor with a large living room opening to a main dining room. The dining room extends to the large chef’s kitchen and its breakfast bar which easily seats 6 for casual dining. This floor also contains one of the 2 primary suites toward the rear of the home with views of the backyard pool area. The main level also has a large ½ bath and an additional family/entertainment room. The primary suite is furnished with a king-size bed, a primary bath with dual vanities, water closet and extra-large shower. Closet space was not spared and there is abundant storage as well. The kitchen has a large walk-in pantry, upgraded appliances, soft close drawers and doors and plenty of storage. The upper, 3rd level, has a large family room, a breakfast bar, mini fridge, microwave and plenty of counterspace and storage for long lazy nights in front of the tv or with a good book. The laundry area is on this floor along with another primary suite, primary bath with a beautiful soaking tub, separate shower, water closet and walk-in closet as well as 2 additional large guest bedrooms and a full bath. All this is wrapped with beautiful outdoor space, private balconies and porches on all living levels and a covered sitting area beside the sparkling heated pool. If you prefer the beach, Siesta Key beach is a short 3 block walk, and the village is filled with wonderful restaurants, shops and all beach life’s necessities are all close at hand. The Seller’s preference is to sell the home turnkey but if that isn’t your desire, they will accommodate the needs of the buyer.

5365 Calle Florida, Sarasota
$1,300,000
2 Beds ⋅ 2 Baths ⋅ Gulf & Bay Club SubDv. ⋅ 34242 Zip Code
Knock, knock your slice of paradise is calling! There’s no place like this home or home away from home! A gorgeous view in an exquisitely updated condo on the world’s finest beach! What more could you ask for?!! HURRICANE WINDOWS, Quartz countertops EVERYWHERE (even in the laundry room!), wine refrigerator, Kitchen Aid appliances, new cabinetry (including in the bathrooms), closet built-ins, luxury vinyl plank flooring, tasteful, coastal furniture, electronic remote control Hunter Douglas shades on windows, ample storage, full size utility room, enclosed balcony professionally done so it truly feels like part of the home. Being sold furnished with everything you need to get started living the good life! The Gulf & Bay community is packed with amenities and spacious grounds, located mid-key with easy access to the north or south bridge, with a guarded gate and on-site property management, you will not be disappointed! 4 Tennis (3 Plexi cushion, 1 clay), 6 pickleball courts, and 2 racquetball courts, shuffleboard, a fitness room and clubhouse with a library, computer and meeting/event room and card room. The common area and multiple pools are lushly landscaped and manicured, giving you that true resort feel. The parking lot is pavered and carports, with deeded parking spaces, are included with units as well as ample guest spaces. There is also a carwash area and there are electric vehicle charging stations. Building E has the advantage of being closer to the water and therefore a more up-close view of the Gulf. Click your heels together and power up that hot air balloon (or whatever mode of transport you prefer) and hurry over to follow your heart and mind and gather the courage to grab your slice of paradise before it’s gone! This is not a dream, it’s a dream come true!

5750 Midnight Pass Road Unit 508 E, Sarasota
$650,000
2 Beds ⋅ 2 Baths ⋅ Palm Bay Club SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. OPPORTUNITY AWAITS! This first-floor end-unit condo is one of only a few Gulf-to-Bay properties on Siesta Key, offering unmatched lifestyle and investment potential. Featuring 2 bedrooms and 2 bathrooms, it can serve as your primary residence, vacation retreat, or an income-producing rental, generating $40K–$60K in just 9 months with both weekly and seasonal leasing opportunities. The welcoming foyer includes a large storage closet, while the spacious great room opens to an enclosed lanai with sliding glass doors—perfect for enjoying refreshing Gulf breezes. The primary suite boasts an oversized walk-in closet, private lanai access, and a bath with a step-in shower and glass doors. Recent updates include a new hot water heater and an HVAC system less than 2 years old, ensuring comfort and peace of mind. Covered carport parking is conveniently located just outside your unit. Owners enjoy private access to world-famous Siesta Key Beach and resort-style amenities such as two pools, a spa, tennis courts, and a fully equipped fitness center. For boaters, slips are available on a first-come, first-served basis along the Intracoastal Waterway. With on-site Palm Bay rental management and concierge services, ownership here is truly worry-free and enjoyable.

5964 Midnight Pass Road Unit N-16 (AKA # 135), Sarasota
$575,000
2 Beds ⋅ 1 Baths ⋅ La Siesta SubDv. ⋅ 34242 Zip Code
Siesta Key 2BR/1BA condo updated in 2021 with sweeping Gulf views from a private balcony. Bright, open living area flows to the outdoors. Prime island location close to dining and shops. A standout coastal retreat or investment. Come enjoy the Siesta Key lifestyle!

925 Beach Road Unit 310, 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
$700,000
3 Beds ⋅ 2 Baths ⋅ Ocean Beach SubDv. ⋅ 34242 Zip Code
Selling the LOT for this price - Motivated Seller - Bring All Offers - Build Your Dream Home! .3 Acres with 96' of frontage on Lake Norma, 105' on Ocean Blvd., Awesome Location, Location, Location!!! 1 Mile to Siesta Key Beach, 25 Homes to The Village, 6 Homes to Out of Door Academy, 5 Homes to Siesta Key Chapel Make your offer today & Build Your Dream Home Tomorrow!!!

4637 Ocean Boulevard, Sarasota
$4,250,000
5 Beds ⋅ 5 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Pre-Construction. To be built. Welcome to Your Dream Coastal Retreat Steps from Siesta Beach! This custom three-story home on Siesta Key’s coveted north end features five bedrooms, 4 full and 1 half bathrooms and combines elegant design, elevated construction, and thoughtful luxury finishes. The light-filled, open-concept floor plan seamlessly connects the great room, dining space, and a gourmet chef’s kitchen, which features a quartz waterfall island, custom cabinetry, and high-end appliances. **Expansive sliding glass doors open to over 1,200 square feet of covered outdoor living space, framing views of lush tropical landscaping and a resort-style pool with a sun shelf. The primary suite is a true sanctuary, complete with a free-standing soaking tub and an oversized walk-in shower. The outdoor living experience is unrivaled. Multiple covered lanais and balconies provide perfect spaces for entertaining, relaxing with morning coffee, or enjoying Sarasota’s sunsets. **Additional features include an elevator servicing all three levels, additional guest suites, flexible bonus spaces, a two-car garage, and storm-rated windows and doors for elevated construction. Stylish coastal architecture with Hardie board siding and a metal roof completes the package. **Located just steps from Siesta Key’s world-famous beaches and minutes from the vibrant shops and restaurants of Siesta Village, this location offers the perfect blend of luxury and island lifestyle. **Short-term rentals are permitted, providing a flexible investment opportunity. **This property is also conveniently located in close proximity to Downtown Sarasota, Southside Village, and top hospitals, restaurants, and entertainment. This is your chance to build a custom masterpiece in a truly unparalleled location. Build your dream home with us, or purchase the lot and plans separately. Use our trusted general contractor or bring your own builder. Are you ready to turn your vision into a reality?

160 Garden Lane, Sarasota
$1,075,000
2 Beds ⋅ 2 Baths ⋅ Horizons West SubDv. ⋅ 34242 Zip Code
Rare Opportunity to acquire an upper floor end unit with full western Gulf and Crescent Beach views extending from Point of Rocks to northern Siesta Key. This 6th floor condo has beach views from all rooms – even the bathrooms. Make this the perfect owner-occupied or second home retreat as the possibilities are endless: Remove the NON-load bearing wall between the living room and 30-foot balcony to add a wall of glass and expand the already amazing water views. Create your dream kitchen by removing walls and expanding the area. Enlarge the primary bathroom to create a sumptuous en-suite. Add a laundry room with washer and dryer. With 1,552 interior square feet and over 200 feet of enclosed balcony, you can even add an office or den. This home comes with IMPACT WINDOWS and DOORS. This fabulous find is located in Horizons West, a gulf-to-bay community consisting of over 7-acres, all being newly landscaped. The gulf side has 300 feet of deeded beach access, beach cabanas, a beachside pool and spa, and beachside grilling areas. There is a second pool adjacent to the community clubhouse. Explore the grounds and private intracoastal waterway park with day dock that is perfect for picnicking, fishing or just watching boats cruise by. Bayside is the perfect place to launch your kayaks and paddle boards to explore the mangroves. Use Siesta Key’s free trolley to partake in the Key’s exceptional dining, entertainment, and shopping.

6140 Midnight Pass Road Unit 601, Sarasota
$334,900
1 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
Welcome to Siesta Harbor, a highly desirable 55+ waterfront community on world-famous Siesta Key, where spectacular canal and Intracoastal Waterway views create the perfect backdrop for relaxed coastal living. Located directly across the street from deeded beach access, you'll enjoy the best of both worlds—boating from your backyard and one of America's top-rated beaches just steps away. This beautifully renovated one-bedroom, two-full-bath residence has been thoughtfully redesigned from top to bottom with exceptional attention to detail. Features include impact windows throughout, a stunning contemporary kitchen with floating cabinetry, quartz countertops, new stainless appliances, designer lighting, updated bathrooms with floating vanities, illuminated mirrors, a beautifully remodeled shower, new hot water heater, updated electrical outlets and switches, new interior doors, hardware and baseboards, smooth textured ceilings with the popcorn removed, and an HVAC system that's approximately two years old. The intelligently designed floor plan offers an abundance of storage rarely found in a one-bedroom condominium, including two bedroom closets with a walk-in closet, linen closet, hallway coat closet, pantry, and a private exterior storage room perfect for bicycles, beach chairs, fishing gear, and other coastal essentials. Boaters will appreciate the opportunity to dock a vessel up to 30 feet for approximately $1,000 annually (subject to availability and community guidelines), making it easy to explore Sarasota Bay and the Intracoastal Waterway right from home. Residents enjoy an outstanding collection of amenities including a heated waterfront pool, fishing and boat-watching pier, tandem boat docks, fitness center, recreation clubhouse, shuffleboard courts, outdoor grilling area, beautifully maintained grounds, and complimentary laundry facilities conveniently located on multiple floors. Exclusive FOB beach access through Crescent Arms makes trips to the powdery white sands of Siesta Beach effortless. The property also includes a covered carport parking space (#537) along with ample guest parking. Siesta Harbor is rental-friendly and welcomes service animals in accordance with applicable regulations. Offered at just $334,900—below competing renovated waterfront properties—this exceptional residence presents an outstanding opportunity to own a move-in-ready waterfront condominium with beach access, boating, and the incomparable Siesta Key lifestyle.

1350 N Portofino Drive Unit 107, 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
$349,000
1 Beds ⋅ 1 Baths ⋅ White Sands Village SubDv. ⋅ 34242 Zip Code
PRICE IMPROVEMENT. Exceptional Value on Siesta Key Rarely available and beautifully updated, this second-floor 1-bedroom, 1-bathroom residence in White Sands Village offers the perfect blend of coastal living and investment opportunity. Ideally located just across the street from Siesta Key Beach, the condo also enjoys a coveted view of the lush interior courtyard, providing a peaceful and serene setting. This turnkey furnished unit is move-in ready and features a bright, open floor plan with tasteful coastal updates throughout. The enclosed lanai adds valuable additional living space, ideal for relaxing or entertaining. The A/C system is serviced annually and is in excellent working condition, offering added peace of mind. White Sands Village is a hidden gem, known for its affordability, strong amenities, and rental flexibility. Residents enjoy a heated community pool, a newly renovated clubhouse with kitchen and gathering spaces, beautifully maintained grounds with paver roadways, and covered carports. Community boat docks are available on a first-come basis for a nominal fee. Small pets are welcome for both owners and tenants—an increasingly rare benefit on Siesta Key. With a two-week minimum rental policy and an on-site rental agent, this community supports steady income potential, making it equally attractive as a personal retreat or investment property. The nearby free Siesta Key trolley provides easy access to Siesta Key Village, dining, shopping, and downtown Sarasota’s cultural and dining scene. This price improvement enhances an already compelling opportunity to own in one of Siesta Key’s most desirable communities—where comfort, location, and income potential come together seamlessly.

5641 Midnight Pass Road Unit 904, Sarasota
$495,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
One or more photo(s) has been virtually staged. BEST PRICED UPDATED VILLA WITH GARAGE ON SIESTA KEY! Don't miss this opportunity to own this lovely REMODELED VILLA just steps from the sand! This 2 bed/2 bath villa nestled in the premier GULF FRONT property of Whispering Sands is the perfect island getaway. Remodeled in 2025, this villa features all NEW vinyl plank flooring, paint, baseboards, trim, molding, and all interior doors. The bright NEW galley kitchen is a true highlight, offering stylish soft close cabinetry, granite countertops, stainless Whirlpool appliances, a side by side fridge with icemaker/dispenser, stainless farmhouse sink, and recessed and under-cabinet lighting. Both bathrooms have been refreshed with new granite counters, cabinets, vanities, and fixtures for a clean, contemporary feel. You’ll enjoy the ease of indoor-outdoor living with a tiled screened lanai – perfect for your morning coffee or evening relaxation. It could be further enclosed with windows or sliders and turned into a sunroom. This villa also features a nice skip trowel ceiling finish and plantation shutters. One car garage with NEW 2026 epoxy floor. NEW 2025 full sized Maytag WASHER & DRYER. NEW 2025 VILLA ROOF. 2025 HVAC system and 2025 water heater. Ideally located just around the corner from Whispering Sands’ two sparkling heated pools, clubhouse (currently in the beginning stages of being remodeled and which will include a fitness center and catering kitchen), NEW beachside Tiki Hut, shuffleboard, and 800' of your own private beach on the Gulf — perfect for enjoying Siesta Key’s world famous quartz sand and spectacular sunsets! When you're not luxuriating in the pool or going for a dip in the Gulf, step out of your front door and walk to shopping and dinner! Whispering Sands is situated right around the corner from the colorful boutiques and fine restaurants of Siesta Key Village. Embrace the island lifestyle! Whether as a year-round residence or a vacation retreat, this maintenance free Gulfside villa combines ease, style, comfort - and a great investment - in one of Siesta Key’s finest Gulf front properties.

119 Whispering Sands Circle Unit V36, Sarasota
$399,000
2 Beds ⋅ 2 Baths ⋅ Siesta Plat SubDv. ⋅ 34242 Zip Code
BAY OAKS on WORLD FAMOUS SIESTA KEY! This 3rd floor unit is Perfectly positioned with pool view and great rental location! Watch your family swim in the pool directly from your balcony! Priced for immediate sale and ready to rent!! Now is the time to make this 2-bedroom, 2-bath condo your island paradise. With WEEKLY RENTALS allowed, this condo is perfect for a vacation getaway, short-term rentals, your personal island retreat, or full-time Florida living. Fully furnished and BRAND NEW CARPETS IN BEDROOMS making it rental ready. Enjoy poolside views from your screened porch, low HOA fees, and resort-style amenities including a heated pool, tennis courts, waterfront BBQ area, community room with pool table, and a fishing dock set in a lush, park-like setting along the bay. Centrally located on Siesta Key, you’re minutes from North and South Village shops, restaurants, and the free island trolley.

6157 Midnight Pass Road Unit E63, 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
$525,000
2 Beds ⋅ 2 Baths ⋅ Sea Village SubDv. ⋅ 34242 Zip Code
Under contract-accepting backup offers. PRICED TO SELL! NEW impact-rated sliding glass doors were installed in June 2026, providing enhanced storm protection and complementing the home’s existing hurricane-impact windows. Experience million-dollar, direct Gulf views from this ground floor condominium in the sought-after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring throughout, and plantation shutters. Hurricane-impact windows provide additional protection and lasting value. Additional features and upgrades include a 2021 water heater, 2022 HVAC, 2023 electrical panel, in-unit washer and dryer, designated parking, storage shed, and bike storage. Sea Village offers residents a true coastal lifestyle with a heated waterfront pool, tropical grounds, and easy access to dining, shopping, and Siesta Key’s vibrant village. Covered parking and generous guest parking make entertaining convenient. Perfect as a primary residence or seasonal retreat, this home blends unmatched views with modern upgrades in one of Sarasota’s most desirable island communities.

4660 Ocean Boulevard Unit Q1, Sarasota
$650,000
2 Beds ⋅ 2 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan unit has porcelain tile throughout, new appliances, hot water heater, interior washer and dryer, all new plumbing (Pex), hurricane impact front door and sliders, new closet doors, bathrooms, and more. Fantastic rental history! The HOA installed a new roof on the property in 2023, too! Jamaica Royale allows short term rentals so this could be a great investment property or keep it for your own second home. This is the closest gulf side weekly rental property to the main public beach offering 3 swimming pools, grilling stations and shuffle board. Make this great property yours today at a value!

5830 Midnight Pass Road Unit 89, Sarasota
$869,000
4 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Welcome to your slice of paradise on Siesta Key. This beautifully updated 4-bedroom home offers the perfect blend of coastal charm and modern comfort, nestled on a peaceful, tree-lined street in one of the island’s most sought-after neighborhoods. Step inside to discover a bright, airy interior filled with natural light, where spacious living areas flow effortlessly into a large open-air pool, ideal for relaxing afternoons or entertaining under the sun. The heart of the home is designed for easy Florida living, with a thoughtful layout that invites connection and calm. The primary suite features a generous walk-in closet and a calming, private ambiance, perfect for unwinding after a day in the sun. Recent upgrades include a new roof installed in 2021 and a high-efficiency HVAC system from 2020, offering peace of mind and year-round comfort. Outside, the hardscaped, low-maintenance yard adds tropical appeal without the upkeep, while the paver driveway enhances curb appeal with a touch of elegance. Whether you're hosting poolside gatherings or enjoying quiet mornings with coffee and birdsong, this home delivers the kind of lifestyle that feels like vacation every day. And with Siesta Beach just minutes away, you’ll have world-class sand and surf practically at your doorstep. Move-in ready and lovingly maintained, this property is more than a home, it’s a serene escape in the heart of paradise. Did not flood during 2024 storms.

795 Plymouth Street, Sarasota
$929,500
2 Beds ⋅ 2 Baths ⋅ House Of The Sun (Was Known As Haleakala) SubDv. ⋅ 34242 Zip Code
Own a piece of Siesta Key’s shoreline—where Gulf views meet unmatched rental income potential. This turnkey furnished 2 bedroom, 2 bath residence puts you just steps from the powdery white sands of world-famous Siesta Key Beach. Inside, you’ll find a bright, open layout with a spacious master suite, private bath, and a kitchen featuring granite countertops. With rare weekly rentals permitted and a professional in-house rental manager, you can enjoy strong cash flow while still keeping your own beach escape. The community offers everything you need for beach living: a rooftop lounge for the ultimate unforgettable sunsets, beachside pool and tennis courts, fitness center, and outdoor grilling/bar and firepit areas for relaxed evenings right on Siesta Key Beach. Perfectly located near vibrant shops, dining, and nightlife, this property blends luxury, convenienceand income potential into one unbeatable coastal package.

6518 Midnight Pass Road Unit 307, Sarasota
$522,500
1 Beds ⋅ 1 Baths ⋅ Jamaica Royale SubDv. ⋅ 34242 Zip Code
Now pending—accepting backup offers. Turnkey furnished 1 bedroom, 1 bathroom condo at Jamaica Royale on Siesta Key, offering a true hands-off investment opportunity with onsite rental office and future bookings already in place for 2026. This fully renovated condo features high-end finishes and thoughtful upgrades throughout, making it ideal as a vacation rental, second home, or full-time residence. The updated kitchen showcases quartz countertops, a coastal-inspired backsplash, soft-close cabinetry, brand-new stainless steel appliances, and a spacious island—perfect for entertaining. Luxury waterproof vinyl plank (LVP) flooring flows throughout the living area, which is furnished with all-new high-end furniture. The large bedroom is furnished with two queen beds, offering comfort and flexibility for guests. The spa-inspired bathroom features a walk-in shower with built-in bench, porcelain tile, and a sleek backlit mirror. Thoughtful storage, including an expanded hallway closet, enhances functionality and makes this condo truly move-in ready. Jamaica Royale is a well-maintained beachfront community known for its private deeded beach and resort-style amenities, including three pools (one beachfront), newly renovated beachside restrooms and changing facilities, and an outdoor kitchen with grills and seating. With onsite rental management, this condo provides an easy, low-maintenance investment opportunity. Whether you’re searching for a turnkey vacation rental, income-producing investment property, or coastal retreat, this Jamaica Royale condo offers location, luxury, and convenience.

5830 Midnight Pass Road Unit 25, Sarasota
$1,649,000
5 Beds ⋅ 3 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Situated in the sought-after Bay Isle community on Siesta Key, this exceptional three-level pool home combines the best of upscale coastal living with impressive rental performance. Designed to host gatherings of all sizes, it is perfectly suited as a primary residence, vacation escape, or income-producing property. In 2024, it brought in $132,419 in gross rental income, with 2025 projections at $120,681, showcasing its strong investment appeal. Just a short stroll to Shell Beach and minutes from Siesta Key Village and the world-renowned Siesta Key Beach, the home offers unmatched access to award-winning white sand, vibrant dining, and boutique shopping. A complete renovation in 2019 transformed the property with a new metal roof, hurricane-impact windows, patio and garage doors, upgraded AC systems, and an oversized resurfaced lap pool with all-new equipment, including a heat pump. Over 50 Areca palms frame the lush tropical landscaping, providing beauty and privacy while remaining easy to maintain. The outdoor living space rivals a private resort, featuring a sparkling pool, spacious patio, and tranquil surroundings ideal for lounging or entertaining. Inside, natural light fills the open floor plan, creating seamless flow to the outdoor areas and making it a true entertainer’s haven. Impeccably maintained and move-in ready, this Bay Isle residence offers a rare opportunity to enjoy the island lifestyle while benefiting from consistent rental income.

156 Siesta Drive, Sarasota
$7,200,000
5 Beds ⋅ 6 Baths ⋅ Cocoanut Bayou SubDv. ⋅ 34242 Zip Code
A truly exceptional waterfront retreat in one of Sarasota’s most coveted enclaves—Cedar Park Circle on North Siesta Key—this gated and private estate offers over 220 feet of prime bayfront with panoramic views of Cocoanut Bayou and Roberts Bay. Residents enjoy unrivaled boating access to the Gulf of Mexico and exclusive private deeded beach access. Spanning over 10,600 total square feet, including 6,500 square feet under air, this architectural masterpiece features 5 bedrooms, 5.5 bathrooms, and thoughtfully designed spaces across multiple expansive levels with an optional elevator if desired. Soaring ceilings, timeless finishes, and seamless indoor-outdoor living define the home’s coastal elegance. From the welcoming arbored front patio to the impressive wood-and-iron entry, every detail invites you in. Inside, the main living areas are designed for both comfort and grandeur. The foyer/sitting room opens to sweeping pool and bay views, while the massive great room impresses with an oversized stone gas fireplace, beamed ceilings, chandeliers, French doors, and a spacious dining area with custom built-ins. Around the corner, the newly renovated gourmet kitchen and den provide the perfect blend of everyday luxury and effortless entertaining. Here, you’ll find white-on-white custom cabinetry, quartz countertops, an 8-burner Wolf gas cooktop, dual SubZero refrigerator/freezers, a built-in Miele coffee system, and discreetly integrated conveniences like a second dishwasher and refrigerator. The adjoining den and breakfast nook boast tranquil water views, making this space an ideal private retreat. For the boating enthusiast, the property offers 150 feet of dockage, a 20,000-lb boat lift, two jet ski lifts, and a deep-water cut-in dock accommodating a 50’ vessel. After a day on the water, unwind on the expansive travertine-tiled back terrace with its teak summer kitchen, fire pit, multiple lounging and dining areas, and a saltwater infinity pool—all overlooking the bay. Hurricane-impact windows and doors, along with a new Dam Easy flood barrier, provide peace of mind. Private quarters are equally impressive. The luxurious master wing features his-and-her baths and closets, a dedicated exercise room or home office, and an outdoor tiled balcony—combining convenience, privacy, and resort-like amenities. On the opposite side of the home, three spacious guest suites each offer private balconies and baths. The ground floor grotto/media room with a full bar, wine room, steam bath, fifth bedroom, and two outdoor patios creates the ultimate guest haven. Additional features include dual laundry rooms (one on each wing), an oversized two-car garage with built-in storage, additional parking within the compound, and under-house storage. Designer landscape lighting, a four-zone heating/cooling system, and meticulous craftsmanship throughout ensure this residence is as functional as it is beautiful. This is a once-in-a-lifetime opportunity to own a one-of-a-kind sanctuary where private beach access, world-class boating, and timeless coastal luxury come together seamlessly at Cocoanut Bayou’s exclusive waterfront enclave.

265 Cedar Park Circle, Sarasota
$480,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Move in ready AND priced to sell quickly! Don't miss the chance to own this beautifully updated turnkey furnished 2-bedroom condo at Peppertree Bay, available at an unbeatable price! Experience resort-style living in this bayfront and beachside community. The interior boasts an open floor plan with spacious, welcoming rooms, tile and luxury vinyl plank flooring, and a generous 29-foot lanai. Peppertree Bay offers luxurious amenities, including under building parking, private beach access, two heated swimming pools, tennis and pickleball courts, two clubhouses, a fitness center, and a fishing pier. It’s like a vacation every day! When you want a change of pace, leave your car behind and take the trolley to all the wonderful restaurants and shopping Siesta Key has to offer. With onsite management and a rental desk, this Peppertree Bay condo serves as an ideal coastal getaway or a smart investment choice. Don’t let this one get away.

1255 E Peppertree Drive Unit 201, Sarasota
$1,595,000
3 Beds ⋅ 3 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Just minutes from the powdery white sands of Siesta Beach and the vibrant energy of Siesta Key Village, yet tucked away on a quiet, oak-shaded street, 5121 Oxford Drive is a 3-bedroom, 3-bath waterfront pool home. Located on the coveted Grand Canal, with 50 feet of deep-water frontage, you’ll be on the bay in just minutes. A brand-new dock and 10,000 lb. lift (2025) are ready for your boat, and the property is golf cart–friendly, allowing you to cruise easily to the Village or beach. For the right buyer, furnishings, the golf cart, and even the boat are negotiable, creating a truly turnkey opportunity. Every major upgrade has been completed so you can enjoy the home from day one. Impact-rated low-e sliders and exterior doors (2025) fill the space with natural light and security. The durable metal roof is built to last, while all-new HVAC systems (2025), a whole-home dehumidifier (2025), and a tankless water heater (2023) ensure modern comfort. The garage features hurricane-rated insulated doors (2020), a mini-split A/C (2025), and epoxy flooring (2025)—perfect for keeping your toys protected in style. The gourmet kitchen, fully renovated in 2023, boasts quartz counters, high-end stainless steel appliances, custom solid wood cabinetry and a sleek coastal design. The master bath (2024) feels like a spa retreat, and even the fireplace area was refreshed in 2021, adding a warm focal point to the living space. The living area flows onto wraparound balconies made from Cumaru Brazilian teak, overlooking the sparkling new saltwater pool (2024) with electric heater, marble travertine pavers, and all-new equipment. This property is made for the lifestyle you’ve been dreaming about - morning coffee as boats glide by, afternoons on the water, and evenings walking or taking the golf cart to dinner in the Village. Whether you’re seeking a full-time residence, a vacation getaway, or a high-demand rental, 5121 Oxford Drive delivers it all - turnkey option, fully upgraded, and ready for you to enjoy.

5121 Oxford Drive, Sarasota
$595,000
2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
ENJOY THE BAY VIEWS FROM THIS UPDATED HOME! Kitchen with Granite countertop, Laundry in Residence, office space off foyer. Partially Furnished! Carport! Island Reef is a serene waterfront community, one of the few Gulf to Bay community that offers many desirable amenities including: Beach, Boat Docks (lifts allowed) two lit tennis courts, pickleball, 2 fitness rooms, Kayak Storage, Library, Billiards, game room, clubhouse, two heated pools and Gas Grills, PET FRIENDLY! Tropical Gardens add to the appeal of Island Reef and this wonderful community is close to two of Siesta Key’s popular restaurants. Complimentary trolley to Siesta Beach, Siesta Village for dining, shopping, ice cream, mini donuts, cute brunch spots and dancing and live music every night of the week!

8779 Midnight Pass Road Unit 401H, Sarasota
$1,050,000
2 Beds ⋅ 2 Baths ⋅ Spindrift SubDv. ⋅ 34242 Zip Code
This beach front opportunity in spindrift does not come around often! With a prime Siesta beachfront unit within a three building, six unit complex that is only a five minute walk from Siesta key village. If you're looking for your own quiet place away from tourist crowds and large associations, then this unit is for you. This unit overlooks the pool with the stunning backdrop of your own piece of Siesta Beach. The unit is on the second floor. The two over-sized bedrooms that pair with two bathrooms just need a little updating. The nice sized kitchen needs a little renovation and paint color of your choosing to create your perfect home. The open floor plan boasts a lot of space for a family gathering nestled around the wood burning fireplace; leaving enough room for a large dining area. The A/C is 2021. New vinyl wood flooring and brand new roof installed 2025. New hardy board siding is set to be installed as well as a new window to be installed upon permitting. Two sliding glass doors that lead to a wrap-around balcony for a panoramic view of the neighborhood and beach front. Around the corner you have Siesta Village full of your shopping desires, Beach bars to fulfil your thirst, and your favorite local restaurants that ties in your perfect beach vibe. (From HOA Management: Rental restrictions are not enforced, so can be less than 30 day rental)

460 Beach Road Unit B2, Sarasota