Between $400,000 - $500,000 Siesta Key FL Real Estate, Homes, Condos for Sale - Ed Grabowski

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

Welcome to your own piece of paradise on world renowned Siesta Key! This beautifully updated and freshly painted 2 bedroom, 2 bathroom residence in the highly desirable Siesta Harbor 55+ community is clean, bright, inviting, and ready for its next owner. Just steps from the soft, powdery sands of Siesta Beach, this is the perfect opportunity to enjoy the laid back island lifestyle you've been dreaming about. From the moment you walk in, you'll appreciate the fresh, coastal feel and thoughtful updates throughout. The residence features beautiful luxury vinyl flooring, a renovated kitchen, updated bathrooms, a brand new vanity in the guest bath, and new and newer appliances. The open and comfortable floor plan is filled with natural light and designed for easy everyday living. One of the true highlights is the spacious all seasons lanai, where you can sit back, relax, and take in the fantastic waterfront views. Watch boats cruise along the shimmering saltwater canal as you enjoy your morning coffee or unwind with a glass of wine in the evening. The canal leads directly to the Intracoastal Waterway and Gulf of Mexico, creating a beautiful backdrop and a constant reminder that you are living on Siesta Key. Siesta Harbor is an active and welcoming 55+ community with an incredible selection of amenities and activities. Enjoy the heated pool and spa, fitness center, sauna, clubhouse, shuffleboard courts, private Intracoastal pier, and a wonderful social calendar filled with community events and activities. Fishing enthusiasts will love the private waterfront pier, while boaters have the opportunity to lease dock space on a first come, first served basis. Residents also enjoy deeded beach access through Crescent Arms, beautifully maintained tropical grounds, on site management, private storage, and same floor laundry. With the free trolley stop conveniently located just outside the community, Siesta Key Village, local shops, restaurants, and entertainment are all easily accessible. The South Bridge provides convenient access to mainland Sarasota, downtown, and the area's many cultural attractions. Whether you're looking for a full time home, a seasonal escape, or your own island retreat, this residence offers an incredible combination of location, updates, waterfront views, amenities, and lifestyle. Clean, freshly painted, beautifully updated, and ready to enjoy, this is a fantastic opportunity to own a little piece of paradise on Siesta Key. Come see why life is better on the Key!

1300 N Portofino Drive Unit 103, Sarasota

$467,000

1 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

STUNNING TURNKEY ONE-BEDROOM, TWO-BATH CONDO AT SIESTA HARBOR! Welcome to your own slice of paradise on Siesta Key! This spacious, turnkey one-bedroom, two-full-bath condo features a bright, open floor plan and a fabulous private lanai overlooking the canal, with beautiful views toward the Intracoastal Waterway. Enjoy resort-style amenities including a heated pool, outdoor spa, poolside shower, shuffleboard, barbecue area, and clubhouse. The clubhouse offers a full kitchen, fitness room, sauna, and library. Boat slips are also available for rent through the Harbor Master. Located directly on the main Intracoastal Waterway, the complex and fishing pier provide the perfect setting for relaxing evenings, entertaining, and watching dolphins and manatees pass by. Best of all, beach access is directly across the street through Crescent Arms, making it easy to enjoy the world-famous Siesta Key beaches. The trolley and SCAT bus stop right outside the complex, while restaurants, shops, and other conveniences are just a short walk away. With easy access on and off the Key, this is the perfect beach retreat, vacation home, or investment opportunity. Come experience the Siesta Key lifestyle—you deserve paradise!

1300 N Portofino Drive Unit 305, Sarasota

$500,000

1 Beds ⋅ 1 Baths ⋅ Beach Club At Siesta Key SubDv. ⋅ 34242 Zip Code

Lender paid 1-0 Buydown Interest Rate by using our preferred lender! Welcome to your own slice of paradise at the Beach Club at Siesta Key! This beautifully furnished 1-bedroom, 1-bathroom condo offers a chic, modern resort-style retreat just steps from the world-famous white-sand beaches of Siesta Key. Located in Building B, this turnkey residence features a full kitchen with stainless steel appliances and stylish stainless-accented cabinetry, a spacious living area, in-unit laundry, and a beautifully updated bathroom with a walk-in glass shower. Freshly painted in 2025 and offered fully furnished, this condo is ready to enjoy as a personal beach getaway, investment property, or both. Step outside and enjoy the community’s heated pool, hot tub, shared patio, and grilling area, with convenient gated beach access through a private walkway shared with surrounding properties. Siesta Key Public Beach is approximately 2 miles away and offers tennis courts, a playground, picnic and grilling areas, concessions, and the island’s famous weekly drum circle. When you’re ready for more island fun, Siesta Key Village is nearby with restaurants, boutiques, live entertainment, and tropical cocktails. Built in 2009 on stem walls, the building is elevated and sustained no storm damage. The Beach Club at Siesta Key has fully recovered from the 2024 hurricanes, with total cash, operating funds, and reserves exceeding $300,000. Recent community improvements include new landscaping in 2026 and new pool heaters and pumps in 2025. The roof is inspected annually, the most recent reserve study was completed in 2024, and a new reserve study is currently in progress. Owners are not required to use the onsite rental office and may rent the unit independently; the onsite RVA office is available for guests who book through RVA. The condo fee includes cable, water, sewer, trash, internet, beach access, pool, spa, and grill. Whether you’re looking for a relaxing island escape or a flexible rental opportunity, this is an exceptional way to enjoy the laid-back luxury and year-round lifestyle of Siesta Key.

1020 Sun N Sea Drive Unit 102, Sarasota

$435,000

2 Beds ⋅ 1 Baths ⋅ Contntls Sea Club SubDv. ⋅ 34242 Zip Code

Under contract-accepting backup offers. Community Beach access to Siesta Key's Beach. Community Dock and Fishing Pier. Community Marina. Large Community Heated Pool. Community BBQs. Poolside Tiki Cabana, Bathrooms and showers, Community laundry machines on first floor. Gated and community building at entrance. 1–7-day rentals grandfather in so great rental income or come enjoy it as your family beach/bay condo! Great option for local owners that want beach access and fun waterfront use for family and guests yet can own a home off the key and have the best of both worlds. Cute unit and coastal charming community! Turn-key furnished so ready to enjoy or rent to cover you expenses while enjoying when it is vacant!

5955 Midnight Pass Road Unit 20E, Sarasota

$479,000

1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code

Beautifully Updated One-Bedroom Condo on Siesta Key Enjoy the best of island living in this beautifully updated one-bedroom, one-bath condominium on Siesta Key. This inviting unit has been completely updated and features all-new appliances and a new water heater, offering a fresh, move-in-ready interior. The community offers an impressive selection of on-site amenities, including: • Two swimming pools • Tennis courts • Four shuffleboard courts • Beach access Located on beautiful Siesta Key, this condo offers the perfect combination of comfort, convenience, and the relaxed Florida lifestyle. Whether you’re looking for a full-time residence, seasonal getaway, or investment opportunity, this property provides an excellent opportunity to own a piece of paradise just steps from the beach.

6006 Midnight Pass Road Unit 60, Sarasota

$395,000

1 Beds ⋅ 1 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code

Virtually Staged. COASTAL RESORT LIVING JUST MINUTES FROM SIESTA KEY BEACH! Enjoy the best of Siesta Key living in this beautifully updated and move-in-ready condominium at Harbor Towers, one of the island's most sought-after waterfront communities. Located just a short distance from the world-renowned Siesta Key Beach, this large one-bedroom, one-bath residence offers beautiful bay and intracoastal water views, exceptional amenities, and outstanding ownership value. **Recent Upgrades & Improvements:** New vinyl flooring going in week 0f 6/22/26 • NEW luxury vinyl flooring throughout • NEW air conditioning system (2026) • NEW hot water heater (2026) • Fresh interior paint • NEW window • NEW bathroom plumbing, sink and toilet • NEW main electrical panel • NEW screened lanai door • Keypad entry system • All special assessments paid • HOA fees paid through 2026 • No outstanding assessments or fees The spacious floor plan features an oversized bedroom with room for multiple sleeping arrangements, generous closet space, a full-size kitchen with refrigerator and dishwasher, keypad entry, and abundant natural light. Harbor Towers offers an impressive collection of resort-style amenities, including a heated pool and spa, fitness center, marina, fishing pier, boat slips available for lease, tennis courts, clubhouse, walking paths, grilling areas, and secured gated access. A deeded covered parking space is conveniently located near the building entrance. Ideal as a primary residence, vacation getaway, or investment opportunity. Historical rental activity reflects gross rental income of approximately $34,000 annually; future rental income may vary. Ideally situated near Siesta Key Village, residents enjoy convenient access to restaurants, shopping, entertainment, and beach access, with trolley and transportation options nearby. Experience the convenience, amenities, and coastal lifestyle that make Harbor Towers one of Siesta Key's most desirable waterfront communities. With elevator access, a practical layout, convenient amenities, and low-maintenance living, this residence offers comfort and ease of ownership. Some photos virtually staged

5855 Midnight Pass Road Unit 514, Sarasota

$480,000

3 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

This rare, freestanding 3-bedroom, 2-bath villa presents an exceptional opportunity to create the coastal home you've always envisioned in the premier Gulf front community of Whispering Sands. With its highly desirable floor plan, attached 2-car garage, and private fenced patio, this residence offers the perfect foundation for a truly personalized retreat. Professionally remediated following Hurricane Helene, this villa is being offered in its current condition. Featuring concrete floors, partial drywall, and no kitchen or bathroom fixtures, this residence offers a true blank canvas – inviting you to select every finish, fixture, and detail to create a home that reflects your own style and vision. Washer and dryer hookup is located in the garage. Important exterior improvements have already been completed, including NEW 2025 villa and garage roofs and fresh exterior paint, while a comprehensive two-year community landscaping enhancement plan is in the planning stages. Life at Whispering Sands is about far more than just your residence. Enjoy 800 feet of PRIVATE quartz sand beach, two heated pools, clubhouse (currently undergoing complete remodeling that will also include a catering kitchen and fitness rooms), beachside Tiki Hut, shuffleboard courts, canoe/kayak storage, and professionally maintained grounds, all just a short stroll from the shops, restaurants, and vibrant charm of Siesta Key Village. The comprehensive HOA fee includes cable, high speed internet, recreational amenities, landscaping, reserves escrow, HOA insurance, on-site management & maintenance team, security, water and sewer – allowing you to spend more time enjoying the island lifestyle. Freestanding villas in Whispering Sands are exceptionally rare. This is a unique opportunity to create a home that reflects your personal taste while enjoying maintenance-free living in one of Siesta Key's most desirable 55+ Gulf front communities.

208 Hourglass Way Unit V11, Sarasota

$499,000

2 Beds ⋅ 2 Baths ⋅ Bay Oaks Estates SubDv. ⋅ 34242 Zip Code

New Listing Photos now attached! Weekly rentals, prime Siesta Key location, and immediate income potential—this is the beach investment opportunity buyers wait for. Welcome to Bay Oaks, where island living meets exceptional rental flexibility in one of the most desirable communities on Siesta Key. This beautifully updated 2-bedroom, 2-bath condo is being offered fully turn-key furnished, making ownership effortless from day one. Even better, future rental bookings are already in place, allowing you to start generating income immediately—no waiting, no setup, no downtime. Just close and collect. Since its last listing, the home has been enhanced with a newly renovated kitchen, featuring stylish modern finishes that elevate both form and function. The bright, open-concept layout creates an inviting coastal feel, with seamless flow between the kitchen, dining, and living spaces—perfect for relaxing after a day at the beach or entertaining guests. Enjoy peaceful mornings on your private balcony surrounded by lush tropical landscaping, while both spacious bedrooms provide comfortable retreats filled with natural light. Bay Oaks is beloved for its unbeatable location and resort-style amenities. Situated on the bayside of Siesta Key and just moments from the powdery sands of world-famous Siesta Key Beach, residents and guests enjoy access to a sparkling pool, private fishing pier, tennis courts, shuffleboard, and beautifully maintained grounds. Hop on the free trolley for quick access to the restaurants, boutiques, and nightlife of Siesta Key Village. For investors, the biggest advantage is Bay Oaks’ highly desirable weekly rental policy—a rare and valuable feature on Siesta Key that opens the door to strong vacation rental demand and attractive income potential. Whether you're searching for a personal beach getaway, a savvy investment property, or the perfect combination of both, this Bay Oaks condo delivers. Flip-flops encouraged. **Updated Listing Photos Now Attached!**

6157 Midnight Pass Road Unit E12, Sarasota

$400,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

Opportunity awaits in one of Siesta Key's most desirable GULF FRONT communities! Perfectly positioned on the 3rd floor of the popular Tropic View building just steps from the sugar white sands and turquoise waters of the Gulf, this 2 bedroom/2 bath Whispering Sands residence offers exceptional potential for the buyer with vision. The sellers are willing to offer a $30,000 SELLER CREDIT with an acceptable contract, to offset any future improvements or assessments. Ready for renovation and priced accordingly, this property serves as a blank canvas for updates and customization to suit your style. The spacious floor plan is complemented by a 34' screened and glass enclosed lanai that spans the entire length of the unit, providing additional valuable living space and a comfortable setting in which to relax or entertain year round. The primary bedroom includes a walk-in closet and ensuite bath with glassed shower. Equally spacious, the guest bedroom is large enough to accommodate two queen beds. Furnishings are negotiable. This unit also comes with an assigned storage locker on the same floor for all of your beach essentials. Whether you're seeking a seasonal escape, year round residence, or an opportunity to create a personalized coastal retreat, this property offers the prefect foundation in an exceptional location. Bring your imagination and discover the possibilities that await just moments from the Gulf!

101 Whispering Sands Drive Unit 301, Sarasota

$469,900

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

This second floor 2-bedroom, 2 bath condo is located in the Marlin House in the 55+ community of wonderful Siesta Harbor! This unit offers an open floor plan with plenty of light. Step out onto one of the balcony’s to view the peaceful water, boats going by and you may see dolphins playing while you are enjoying your morning beverage. This community offers more than just serene water views. Included in the many amenities are a heated pool, shuffleboard, library and a fitness area. Feel free to participate in movie night, Tai Chi and Happy Hour along with many other activities offered at the clubhouse. Are you a boater? Siesta Harbor is one of the few condos on Siesta Key that offers a boat dock with deep water, for those interested in this bonus extra. If you wish to walk to the beautiful Siesta Key beach, voted best beach in the USA and the world, private access right across the street through a deeded access. Siesta Harbor keeps its grounds and buildings well maintained, recently updated with new roofs and updated common areas. This unit is a must have, with the deep water of the Intracoastal Waterway right in your backyard, the peaceful and serene atmosphere of the area, the beautiful beach just a shore walk away and it can be an income producer should that be something you want to consider.

1250 N Portofino Drive Unit 202, Sarasota

$429,900

1 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

Bring your boat and dock steps from your back door.. Turnkey living in Siesta Harbor, a 55+ waterfront community, with beautiful canal water views and private beach access. This fully renovated 1-bedroom, 2-bath condo offers an open floor plan, updated kitchen and bathrooms, newer impact sliding doors, and a newer HVAC system (2021). Enjoy peaceful water views from the enclosed lanai as boats pass by. Boat slips are available for vessels up to 30’, with dockage approximately $1,000 annually (buyer to verify with Harbor Master). This property is also investment-friendly, allowing monthly rentals, and has a strong rental history (buyer to verify current rental restrictions and income). Community amenities include a heated waterfront pool, fishing pier, fitness center, clubhouse, shuffleboard, and busy social calendar. Additional features include assigned covered parking and private storage. Located just steps to beach access through Crescent Arms and close to dining, shopping, and the Siesta Key trolley. Ideal as a full-time residence, seasonal retreat, or income-producing property.

1257 S Portofino Drive Unit 104, Sarasota

$424,900

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

Escape the winter chill and step into your endless summer at this meticulously maintained, fully turn-key furnished 2-bedroom, 2-bathroom condo in the desirable Siesta Harbor community on Siesta Key. This 4th-floor gem has been lovingly cared for by the owners and offers charming peek-a-boo ocean views along with direct canal frontage — perfect for morning coffee with a waterfront breeze or romantic sunset dinner. This active 55+ community delivers the true Siesta Key lifestyle with outstanding amenities: deeded beach access via Crescent Arms, a fishing pier on the Intracoastal Waterway, a heated community pool, boat docks, onsite management, and a vibrant calendar of social activities. You’re just minutes from downtown Sarasota’s top restaurants, shops, and cultural attractions.Enjoy low HOA fees, worry-free maintenance, and peace of mind knowing the property has sustained no storm damage. This turn-key condo is your opportunity to own a slice of the laid-back tropical dream on Siesta Key.

1215 S Portofino Drive Unit 406, Sarasota

$500,000

2 Beds ⋅ 2 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code

Turnkey Furnished residence at Island Reef with two bedrooms and two baths. Laundry in residence. 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.

8773 Midnight Pass Road Unit 302G, Sarasota

$429,000

1 Beds ⋅ 1 Baths ⋅ Inlet Apts SubDv. ⋅ 34242 Zip Code

Introducing Inlet Apartments - Siesta Key, a charming, quaint coastal retreat for a tropical vacation or a beach getaway. This second-floor, one-bedroom, one-bath is quiet and peaceful on the Blind Pass Lagoon at far south end of Siesta Key and just beyond your sliding glass doors. You will be instantly captivated by views of paddleboarders and kayaks going by, plus a heated swimming pool and a partial view of the Gulf. With 906 square feet, this residence is sold turnkey furnished, blending modern sophistication with relaxed coastal living. Contemporary new kitchen with new appliances, white quartz countertops, an oversized island, and crafted for effortless everyday living. The open-concept layout flows through the dining room, with a queen-size Murphy bed for extra guests, and living spaces, enhanced by luxury vinyl wood flooring and modern compact ceiling fans that adjust with touch of a button. Wake up to enchanting lagoon views in the tranquil primary suite, and beautifully updated bath. Go outside to a spectacular 200-square-foot screened lanai with pull-down shades for privacy, ideal for morning espresso, sunset cocktails or simply soaking in Siesta Key’s year-round beauty. There are convenient elevators, laundry facilities and assigned parking for each unit. HVAC in 2021, water heater in 2022. Life at Inlet boating amenities included private boat dockage for sailboats and powerboats up to 26 feet (first-come, first-serve basis). The Blind Pass Lagoon leads into Sarasota Bay and onto the Gulf. There are fishing, kayak storage and launch, waterfront pool, all just minutes from Turtle Beach and a short trolley ride to Crescent Key Village. This is more than a condominium at the beach, it’s a one-of-kind opportunity to own a piece of Siesta Key.

9200 Midnight Pass Road Unit 25, Sarasota

$385,000

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

WATERFRONT SIESTA HARBOR!DIRECT VIEWS OF THE CANAL, walk right out to the canal from your Lanai! BEACH ACCESS ACROSS THE STREET! Turn-Key Furnished with a Canal View! Move in ready, enclosed lanai with all furniture and furnishings included! Highly Sought after remodeled Unit on the Canal in the Dolphin Building! Close to the Resort-style Heated Swimming Pool and Spa on the wide part of the canal. This Charming condo is adorned with large windows, bathing the dwelling in warm, natural light. Combining dining and living space, this turn-key furnished condo is Spacious, light and airy with a Gorgeous updated kitchen with granite countertops! Just move right in or rent until you retire! It's ready for your enjoyment! Active 55+ community, close to the pool, clubhouse, beach access, SCAT, the trolley right outside your door! Beautifully done, tile through out, great coastal feel! TURNKEY FURNISHED! This is a great community lots of activities, fitness room, saunas, outdoor spa, heated pool, on site free laundry, pier on the main intracoastal waterway to relax and fish each day, plus boat slips as available, for a reasonable fee through the Association. The location is wonderful, easy on and off the key, walk to shops, restaurants, mini-donuts! Elevate your living experience in this ready-to-move-in, fully furnished home, and enjoy all the benefits and convenience it offers. Don't miss this chance to reside in one of the best locations in Sarasota; your new home awaits!

1215 S Portofino Drive Unit 107, Sarasota

$499,000

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

WATER VIEWS FROM EVERY ROOM! WATERFRONT HEATED POOL, HOT TUB, SHUFFLEBOARD,GATHERING AREA,BOAT SLIP,BEACH ACCES- LIVE IN PARADISE EVERYDAY IN this STUNNING RENOVATED CANAL-FRONT condo designer 2 bedroom, 2 bathroom condo nestled within the coveted Siesta Harbor community, offering private beach access to world-famous Siesta Key Beach just across the street. Situated on the fourth floor with picturesque water views, this beautifully updated unit features gorgeous quartz countertops, gray shaker cabinetry, stainless steel appliances, and brand new ceramic tile flooring throughout. Enjoy peace of mind with the glass-enclosed lanai with sliding glass windows that provides a serene retreat year-round. The open-concept layout flows seamlessly from the modernized kitchen into a bright and welcoming living space, perfect for entertaining or relaxing. Both bathrooms have been tastefully renovated, including a fully remodeled primary and guest bath, and the entire unit was freshly painted. Additional features include a private storage closet, updated lighting, and high-speed fiber optic internet. Siesta Harbor is a vibrant 55+ waterfront community along the Intracoastal Waterway, offering a heated pool, spa, clubhouse, fitness center, shuffleboard, fishing dock, sauna, BBQ area, and boat slips for up to 30’ vessels. Whether enjoying your morning walk to the beach, walking to lunch just minutes away, catching the free trolley to Siesta Key Village, or heading over the nearby bridge to explore downtown Sarasota’s dining, shopping, and cultural scene, this location offers the ultimate in coastal convenience and lifestyle. With monthly rentals allowed 12 times a year, it’s ideal as a personal escape or investment property.

1300 N Portofino Drive Unit 406, Sarasota

$440,000

1 Beds ⋅ 1 Baths ⋅ Gulf & Bay Club Bayside SubDv. ⋅ 34242 Zip Code

Sellers Are Highly Motivated! Welcome to your slice of paradise on world famous Siesta Key, just steps from the powdery white sands of Siesta Beach, recently ranked the number one beach in the United States. This beautifully updated one bedroom, one bathroom residence is the perfect blend of comfort, style, and location, ideal as a primary home, vacation retreat, or income producing investment with weekly rentals allowed. From the moment you enter the gated community of Gulf and Bay Club Bayside, you are surrounded by lush tropical landscaping and a sense of pride in ownership that truly sets this community apart. This impeccably maintained residence offers easy single level living with a bright and open layout, finished in a warm neutral palette. The living and dining areas are enhanced with charming details such as wainscoting, while the updated kitchen features stainless steel appliances, beautiful countertops, and well-appointed cabinetry, all flowing seamlessly into the main living space. The oversized primary bedroom offers a peaceful retreat with a large walk-in closet, while the upgraded bathroom features a stunning tile shower, dual sinks with quartz countertops, and excellent storage. A private laundry area adds convenience, and with no carpet throughout, the home is clean, modern, and move in ready. The AC and water heater were both replaced in 2022. Enjoy your morning coffee in the adorable dining nook or unwind in the bright and airy lanai, the perfect place to relax at the end of the day. This residence also includes a rare one car garage and private driveway, making island living effortless. Gulf and Bay Club Bayside offers an exceptional array of resort style amenities including two heated pools, a clubhouse, fitness center, saunas, pickleball and tennis courts, BBQ areas, walking paths, scenic ponds with fountains, and a fishing pier on the Intracoastal Waterway where you can enjoy sunsets, dolphins, and passing boats. Private deeded beach access just across the street makes it easy to enjoy the turquoise waters and world-famous quartz sand whenever you choose. Ideally located between Siesta Key Village and Stickney Point Road, you are moments from top rated dining, boutique shopping, live entertainment, and water activities. The Siesta Key Trolley provides easy access across the island, making every day feel like a vacation. Offered furnished and thoughtfully updated, this residence truly lives larger than expected and is ready for immediate enjoyment. Whether you are looking to relax, entertain, or invest, this is an incredible opportunity to own in one of the most desirable communities on Siesta Key. Schedule your private showing today and experience the coastal lifestyle you have been dreaming of.

1203 Siesta Bayside Drive Unit 1203-D, Sarasota

$500,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

Step into your own island retreat with this rare END unit in the highly sought after GULF FRONT property of Whispering Sands! Perfectly positioned with a full length screened & glassed lanai overlooking the picturesque lagoon and lush tropical landscaping, this residence captures a peaceful, serene setting with a touch of everyday luxury. Thoughtfully updated and designed for effortless living, the OPEN CONCEPT floor plan features non-slip porcelain tile placed on the diagonal, skip trowel ceiling, and a spacious light-filled living space with an additional, sunny, west facing window. The nicely RENOVATED kitchen is a standout, offering granite countertops, colorful tile backsplash, a 9’ breakfast bar, white soft-close cabinetry, and a suite of GE, Whirlpool, Frigidaire, and LG appliances, all enhanced by overhead recessed, dimmable LED lighting. The cabinetry and granite extend into the entire length of the dining area, creating additional storage and an elegant serving space ideal for entertaining. The original interior living room sliders have been removed to seamlessly incorporate the lanai, transforming it into a sun-drenched sunroom that expands your cooled living space and invites the outdoors in. Just outside, a small brick paver patio off the sunroom offers the perfect spot for grilling, sunning, or unwinding after a day at the beach. Both bathrooms in this unit have been tastefully updated with NEW vanities, fixtures, and cabinetry. Additional highlights include a complete set of 2016 hurricane impact sunroom sliders and 2025 water heater. At Whispering Sands, every day feels like a vacation—with 800’ of PRIVATE beach, two heated pools with new travertine tile decks, clubhouse – currently undergoing a complete remodel which will include a catering kitchen and fitness rooms – beachside Tiki Hut, grills, and canoe/kayak storage - all just a short stroll to the vibrant shops and dining options of Siesta Key Village. Your island getaway awaits!

225 Hourglass Way Unit 106, Sarasota

$425,000

3 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

3 bedroom/2 bath freestanding villa with fenced patio. Remediation from 2024 hurricane damage partially completed. Property has yet to be rebuilt.

208 Hourglass Way Unit V11, Sarasota

$499,900

1 Beds ⋅ 1 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code

THE VIEW, THE VIEW, Location, Location. This is IT! RESORT LIVING UNDER $500,000! EVERY AMENITY AT YOUR FINGERTIPS! BEAUTIFULLY APPOINTED, IMPRESSIVE ENTRANCE WITH WATERFALL, WALK INTO THE LUXURY APPOINTED HUGE FOYER--TURN KEY INCOME GENERATING VACATION HOME! STUNNINGLY SELECTED AND DESIGNED UNIT OVERLOOKING THE POOL AND VIEW OF INTRACOASTAL WATERWAY---DESIRABLE 2 WEEK RENTAL WHEN YOURE NOT HERE, BLOCK IT OUT WHEN YOU COME TO ENJOY AND RELAX! ON SITE RENTAL OFFICE TAKES CARE OF IT ALL! Experience the ultimate in luxury coastal living within the waterfront resort community of Harbor Towers Yacht & Racquet Club, one of Siesta Key’s most desirable gated waterfront communities. This beautifully updated sunrise-facing 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded oasis to provide modern comfort and elegant coastal style with a gorgeous view of the heated pool and outdoor awning for alfresco dining. Being sold turnkey furnished, this third-floor residence is decorated for immediate enjoyment as a full-time home, vacation getaway, or income-producing investment property. The stunningly renovated interior features hurricane-rated windows, a breathtaking quartz kitchen, vinyl plank wood floors and a stunning bathroom accented in gold. The open-concept living and dining area is filled with natural light, creating a bright and welcoming space ideal for relaxing or entertaining. Included is a washer and dryer, plenty of extra storage space directly across the hall and additional large washers and dryers located on each floor for larger items. Perfect for couples and extended stays, this retreat combines modern coastal finishes, large windows, and resort-style amenities just minutes from world-famous Siesta Key Beach and Siesta Key Village. For boating enthusiasts, you’ll find a beautiful marina with boat slips, as available, through the association. This property offers excellent income potential. Two-week minimum rentals are permitted, and owners may utilize the on-site property management office or manage rentals independently. Residents of Harbor Towers enjoy an exceptional collection of amenities, including: *A large marina *Gulf access (no fixed bridges) *Heated swimming pool and shallow wading pool *Three tennis courts *Fully equipped fitness center with new showers and saunas *Clubhouse with social spaces and large kitchen •Outdoor BBQ and kitchen prep area under a beautiful new awning *For boating enthusiasts, boat slips are available through the association plus an ample kayak storage area. Whether you're seeking a luxurious full-time residence, seasonal retreat, or income-generating property, Harbor Towers offers the perfect blend of resort living and coastal charm. Located near shops and restaurants and across the street from the world-famous Siesta Key Beach, don’t miss this rare opportunity to own your piece of paradise on Siesta Key.

5855 Midnight Pass Road Unit 333, Sarasota

$410,000

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

Experience the best of waterfront living in this beautifully updated and fully furnished second-floor condo in the highly sought-after Siesta Harbor community. This TURNKEY 2-bedroom, 2-bath residence offers stunning canal and marina views and a prime location just steps from direct beach access across the street through Crescent Arms. Immaculately maintained and move-in ready, the condo features an enclosed lanai with horizontal sliding windows, tasteful furnishings, and thoughtful updates throughout for comfort and relaxation. The spacious open-concept living and dining areas flow seamlessly into a modern kitchen showcasing white cabinetry, quartz countertops, stainless steel appliances, and ample storage. The primary suite includes a walk-in closet and a stand-up shower, while the enclosed lanai provides the perfect spot to enjoy morning coffee or evening cocktails year-round, with dolphins frequently seen playing in the marina. Siesta Harbor is a vibrant 55+ waterfront boating community situated on its own canal and the main waterway of the Intracoastal Waterway. Boat slips may be available for vessels up to 30' (check with the office for availability). Residents enjoy resort-style activities, and amenities including a heated pool, outdoor jacuzzi and shower, indoor sauna, fitness room, shuffleboard court, fishing pier with seating on the ICW, and a beautifully renovated clubhouse with full kitchen, outstanding library, barbecue area with grills, and a full calendar of social activities. Additional highlights include FOB-accessed private beach access, FREE laundry on the 2nd, 3rd, and 4th floors, one designated covered carport parking space, ample guest parking, covered parking, an on-site manager, lush tropical landscaping, and a new roof (2025). Ideally located near the South Bridge, this community offers easy on-and-off access to the Key, is within short distance to restaurants and shops, and has the free Siesta Key trolley stopping right in front of the complex for easy access to Siesta Key Public Beach and Siesta Key Village. Whether you're watching boats drift by on the Intracoastal, crossing the street for unforgettable sunsets, or enjoying the active social lifestyle, this property is perfect as a vacation retreat, full-time residence, or investment opportunity. You deserve paradise!

1300 N Portofino Drive Unit S206, Sarasota

$462,500

2 Beds ⋅ 2 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code

Island living as it was meant to be. Rarely available two-bedroom, two bath, turnkey furnished second floor residence in a private Gulf front community. Enjoy the charm of an Old Florida setting paired with the ease of true condominium living, where neighbors know one another and weekly rentals are not part of the landscape. This light filled “tree top” condo features its own private exterior entrance, cathedral ceilings, and an open plan design that opens to a private balcony. The updated kitchen was thoughtfully expanded and features solid wood cabinetry, stone countertops, and a breakfast bar designed for casual dining and entertaining. The living room has high ceilings and two sets of sliders. The unit has been fully updated and is decorated in a relaxed beachy style - just move right in! There are essentially two primary suites - one on the main level with an updated bathroom and sliding doors to a private balcony and laundry closet. Upstairs, the second bedroom functions as its own private suite with a full bath and the flexibility to remain open to the living space below or be closed off with shutters for added privacy. Additional highlights include blackout blinds, large storage beneath the stairs, hurricane rated sliding doors and windows, and a separate assigned storage unit. The community provides direct access to the Gulf of Mexico, one of the best fishing piers and waterfront areas on the Key, kayak and paddleboard storage, and a sweeping Gulf front lawn dotted with chairs and umbrellas, the perfect setting to watch dolphins play and boats glide by. The clubhouse is currently not in use and is planned for revitalization. Pet friendly and ideally located on the north end of the island, just a short walk or bike ride to the shops and restaurants of the Village.

208 Pass Key Road Unit 208, Sarasota

$480,000

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

Fabulous End Unit in Albacore! Redone with pride of ownership! walk out to your board dock, close to the Pool, outdoor hot tub, fitness room, shuffleboard, very active clubhouse, lots of activities

1257 S Portofino Drive Unit 101, Sarasota

$402,000

1 Beds ⋅ 1 Baths ⋅ Contntls Sea Club SubDv. ⋅ 34242 Zip Code

*Seller Financing Available* An exceptional opportunity awaits in Sea Club II, one of the limited Siesta Key communities permitting nightly rentals—positioning this residence as a prime option for short-term revenue potential. This ground-level one-bedroom, one-bath condo comes fully furnished and has a proven record of performance, grossing over $50,000 annually in rental income. Designed for effortless use by owners and guests alike, the unit is ready for immediate occupancy or continued income production. Sea Club II offers a resort-style setting along the Intracoastal Waterway. Residents and guests enjoy a recently updated pool area accented by brick pavers, a tiki-style pavilion, and grilling stations, creating an inviting space for leisure and gatherings. Boating and fishing enthusiasts will appreciate the community fishing pier added in 2021 and convenient access to the community boat basin. What truly distinguishes this property is its deeded beach access just a short walk away—delivering the rare advantage of Intracoastal waterfront living paired with direct access to the world-famous sands of Siesta Key Beach. Whether used as a personal island retreat or a high-demand vacation rental, this condo offers flexibility, location, and income potential in one compelling package.

5955 Midnight Pass Road Unit 4E, Sarasota

$450,000

1 Beds ⋅ 1 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code

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

24 Sandy Cove Road Unit A6-D, Sarasota

$470,000

1 Beds ⋅ 1 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code

Move Right Into this VERY SPECIAL SIESTA KEY RESIDENCE & Experience the Best in "Old-School" Island Lifestyle.....Sandy Cove is Truly a Hidden Mid-Century Inspired Oasis where the Lucky Few Residences are just Steps to Lounging, Fishing and Enjoying Sunsets in the PRIVATE GULF-FRONT Recreational Area with Historic Clubhouse & then a Short Stroll to Siesta Key Village.....Designed by renowned architect, Frank Folsom Smith, this COMPLETELY UPDATED & TURNKEY FURNISHED residence in Pet Friendly Sandy Cove III (up to TWO LARGE DOGS!) features Stunning Coastal Contemporary Finishes & Furnishings, including: Hurricane Impact Windows & Sliders, Luxury Vinyl Plank Flooring Throughout; Quartz Countertops, Glazed Ceramic Tile Backsplash, In-Unit Laundry and Custom Closets & Built-ins!. Indulge in Morning Coffee or Evening Cocktails on Multiple Lanai's--the Ultimate in INDOOR/OUTDOOR Living. Monthly Rentals Allowed.....Ideal as Vacation, Investment or Year-Round Residence.

116 Pass Key Road Unit 116, Sarasota

$419,900

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

WATERFRONT RENOVATED 2 bedroom 2 bath condo is Siesta Harbor! WATERFRONT HEATED POOL, HOT TUB, SHUFFLEBOARD,, GATHERING AREA...So many upgrades, granite counters, stainless appliances, ceramic tile, impact sliders, turnkey Furnished! Water views from the living room, main bedroom and lanai, screened in lanai, great active clubhouse, heated pool, outdoor spa, out door shower, shuffleboard, barbecue area and outdoor shower. Private Beach access directly across the street. Siesta Harbor is located on the deepest point of the main intracoastal. Deep canal, boat slip up to 30' boat (check for availability, reasonable annual pricing.) Stunning Dock for fishing or relaxing ..... walk to all, restaurants, shops, easy on and off the key, the Trolley and scat right outside your door! One of the best parts being on the intracoastal with Beach Access! This has it all, just bring your toothbrush and be in paradise! Or rent it out, its a 30 day rental 12 times a year!!

1257 S Portofino Drive Unit 307, Sarasota

$425,000

1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code

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

6006 Midnight Pass Road Unit 4, Sarasota

$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

$410,000

1 Beds ⋅ 1 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code

Have you ever dreamed of living on the beach??? Your chance has arrived! Step into coastal paradise at this turnkey-furnished Siesta Key residence, perfectly situated on the tranquil southern end of the island in the coveted Tortuga community. Residents enjoy a wide range of resort-style amenities, including a heated indoor/outdoor pool, sauna, tennis and pickleball, shuffleboard, and a fishing pier. And, the laundry room is just outside the front door! The community has recently completed major improvements, including a new roof, freshly painted buildings, and a refreshed pool, with all assessments fully paid. The updated clubhouse features a full kitchen and dining area and may be reserved for private gatherings. Impact-resistant windows and doors offer peace of mind. With direct deeded beach access, resort-style amenities, and optional boat slip access ($300/year when available) on the Intracoastal Waterway just across the street, this is island living at its finest. This 800-square-foot condo boasts an open, light-filled floor plan with wood-like tile flooring, crown molding, and a spacious living and dining area that flows effortlessly onto a screened balcony overlooking lush tropical landscaping—perfect for morning coffee or sunset cocktails. The kitchen is a showstopper, featuring quartz countertops, a breakfast bar, and modern appliances, creating a seamless space for entertaining friends and family. The primary suite is a true retreat, complete with a walk-in closet and an en suite bath with dual sinks and granite surfaces. Located on the second floor with elevator access, convenience is key, including nearby shared laundry facilities. Whether you’re seeking a year-round home or seasonal escape, this residence embodies the relaxed sophistication of island life while keeping you just minutes from the world-famous quartz sands of Siesta Beach, the charming boutiques and dining of Siesta Key Village, and the vibrant arts and culture of downtown Sarasota. Coastal living doesn’t get any better than this—your slice of paradise is waiting!

8730 Midnight Pass Road Unit 202A, Sarasota

$440,000

2 Beds ⋅ 3 Baths ⋅ Bay Oaks SubDv. ⋅ 34242 Zip Code

Virtually Staged. Waterfront Siesta Key condo with breathtaking Sarasota Bay intracoastal views and weekly rentals allowed. This rare 2BR/2.5BA Bay Oaks residence is a remarkable opportunity for a buyer with vision to transform a diamond in the rough into a spectacular waterfront getaway, full-time residence, or investment property. Positioned directly on the water, this two-level condo offers the kind of panoramic bay views that are hard to find and impossible to forget. The first floor includes the living room, dining area, kitchen, in-unit laundry, and guest half bath. Upstairs, both bedrooms feature ensuite baths and walk-in closets, including one suite with a private covered balcony overlooking the bay. Bay Oaks residents enjoy a heated waterfront pool, fishing pier, tennis, pickleball, clubhouse, picnic and grill areas, covered parking, bike storage, guest parking, onsite management, and 24-hour video surveillance. Just 1 mile to Siesta Key Beach, with trolley access directly outside the community, this location combines waterfront serenity with easy access to dining, recreation, and the best of Siesta Key.

6157 Midnight Pass Road Unit B12, Sarasota

$480,000

2 Beds ⋅ 2 Baths ⋅ Harbor Towers Y & R SubDv. ⋅ 34242 Zip Code

Have you been searching for your own slice of tropical paradise on Siesta Key? Look no further than this pet-friendly, 2-bedroom, 2-bathroom residence in the perfectly located Harbor Towers Yacht & Racquet Club. This updated home feels fresh and inviting with new luxury vinyl wood-plank style flooring and brand-new hurricane impact-resistant windows for total peace of mind. Harbor Towers is a well-established community situated right in the heart of "The Key," just across the way from the world-famous Siesta Key Beach and a short distance from vibrant shopping and dining. Life here feels like a permanent vacation with access to a resort-style swimming pool, an oversized hot tub, three Har-Tru tennis courts, a fitness center, and a social room with a catering kitchen. Boaters will especially love the on-site marina, where boat slips are available on a first-come, first-served basis for a nominal monthly hook-up fee. Whether you are looking for a primary residence, a seasonal getaway, or a smart investment with a documented rental history, this hidden gem is ready for you. Come and see what makes this such a special place to live!

5855 Midnight Pass Road Unit 227, Sarasota

$425,000

1 Beds ⋅ 1 Baths ⋅ Tortuga SubDv. ⋅ 34242 Zip Code

Siesta Key dream condo located directly on the Gulf of Mexico, offering deeded beach access and boat slip availability on the Intracoastal Waterway just across the street. This inviting one-bedroom residence features quartzite countertops in both the kitchen and bath, along with a new kitchen backsplash that adds a fresh coastal feel. A highly desirable in-unit washer and dryer—an upgrade not found in all units—provides added convenience. Residents enjoy a wide range of resort-style amenities, including a heated indoor/outdoor pool, sauna, tennis and pickleball courts, shuffleboard, and a fishing pier. The community has recently completed major improvements, including a new roof, freshly painted buildings, and a refreshed pool, with all assessments fully paid. The updated clubhouse features a full kitchen and dining area and may be reserved for private gatherings. Impact-resistant windows and doors offer peace of mind, and beautiful Mexican tile throughout means no carpet. The unit is being sold turnkey furnished, excluding select personal items, and offers ample storage along with an assigned covered parking space and plenty of guest parking. Located just one floor up, access is easy via elevator or stairs, placing you moments from the world-famous quartz sands of South Siesta Key. Enjoy a trolley ride to Siesta Key Village or a bike ride to charming shops and restaurants. Conveniently located near cultural attractions and Sarasota International Airport. Rentals are permitted with a one-month minimum, up to three times per year. No pets allowed. Relax and enjoy the effortless coastal lifestyle this private Siesta Key retreat offers.

8750 Midnight Pass Road Unit 102, Sarasota

$450,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

One or more photo(s) has been virtually staged. Welcome to affordable GULF FRONT living! This is currently the best priced 2 bedroom/2 bath condo on the Gulf side of Siesta Key! The seller is also willing to offer a $10,000 SELLER CREDIT with an acceptable offer to offset any future improvements or assessments. This recently updated DOUBLE LANAI CORNER unit is nestled in the southwest corner of the popular Tropic View building, the Whispering Sands midrise closest to the Gulf and 800' of your own private beach. The freshly painted interior features NEW luxury vinyl plank flooring, NEW interior doors, and NEW overhead designer lighting and fans. Four sets of floor-to-ceiling sliders open from the living areas and bedrooms into TWO separate 24’ glassed and screened lanais – complete with epoxy flooring and NEW ceiling fans to capture the coastal breezes. After a full day at the beach, meal prep is easy in your partially open kitchen featuring NEW granite countertops, farmhouse style stainless sink, and NEW 2025 Whirlpool and GE stainless appliances. The spacious primary bedroom includes a nice walk-in closet and an ensuite bath, while the generous second bedroom comfortably accommodates up to two queen beds and boasts a full wall of closet space. Both updated bathrooms feature NEW cabinets, vanities, & fixtures, with glassed walk-in showers and recessed lighting. Brand NEW 2026 HVAC system and 2025 water heater. The unit also comes with its own assigned storage locker located just across the hall, ideal for storing all of your beach essentials. Conveniently located next door to the colorful shops and restaurants of Siesta Key Village, Whispering Sands is a premiere 55+ Gulf front property offering two heated pools, beachside Tiki Hut and gas grills, shuffleboard, canoe/kayak storage, and 800' of PRIVATE quartz sand beach. The clubhouse is currently undergoing complete remodeling. Upon completion in 2026, it will include a full catering kitchen, fitness rooms, large screen TV, and an elegant space for community wide or private social events. New landscaping plan for the building and throughout the entire 25-acre property is currently underway. Attractively priced below market, this unit represents a great investment. Don’t miss this opportunity to experience the ease of island living at Whispering Sands!

101 Whispering Sands Drive Unit 107, Sarasota

$432,500

2 Beds ⋅ 2 Baths ⋅ Inlet Apts SubDv. ⋅ 34242 Zip Code

Discover the true Siesta Key lifestyle in this beautifully updated two-bedroom, two-bathroom condo—an inviting coastal retreat that makes island living surprisingly attainable. Located on the peaceful southern end of the island, this well-maintained second-floor residence offers the perfect blend of comfort, style, and laid-back luxury. The thoughtfully updated kitchen features custom cabinetry, quartz countertops, a spacious island, and stainless-steel appliances, while high-end luxury vinyl plank flooring flows seamlessly throughout. Evenings are best spent on the air-conditioned lanai, where breathtaking sunsets and tranquil surroundings make every day feel like a vacation. Offered turnkey furnished, this move-in-ready condo includes a new A/C system (2024) and new hot water heater (2024)—just bring your swimsuit and sunscreen and start enjoying island life immediately. Step outside to daily sightings of manatees and dolphins in your backyard, or launch your kayak to explore scenic mangrove tunnels before paddling through Midnight Pass into the sparkling Gulf waters. Boaters will love the community boat slips, offering direct access to Sarasota Bay and the Gulf beyond. At the end of the day when it’s time to relax, unwind in the recently updated, heated community pool, or take a short stroll to Turtle Beach, just around the corner. The Inlet community has been exceptionally maintained, featuring a new roof (2024), fresh exterior paint, and a new seawall and dock. Community amenities include, elevator, heated swimming pool, boat slips, kayak storage, bike racks, laundry, and a convenient grilling area. With a Siesta Key trolley stop nearby, enjoying Siesta Key Beach, the Village’s dining, shopping, and nightlife is effortless and no car required. This is your opportunity to own an affordable island escape. Come experience the charm, beauty, and relaxed coastal lifestyle that make Siesta Key so special.

9200 Midnight Pass Road Unit 28, 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

$475,000

2 Beds ⋅ 2 Baths ⋅ Sunrise Cove SubDv. ⋅ 34242 Zip Code

Siesta Key Waterfront Opportunity – Unmatched full bay views from your lanai, Gulf views from your front balcony — this 2 bed, 2 bath condo offers the best of coastal living on Siesta Key. Spacious and ready for your personal touch, this condo is ideal for those looking to renovate and build equity. The community offers two bayfront pools, pickleball and tennis courts, fitness center, kayak racks, and some of the most affordable boat docks around (first come, first served). No flooding in this complex! Reserved carport next to the elevator. Turtle Beach access just across the street. Trolley stop nearby for easy island exploring. Monthly rentals allowed 12x per year with onsite management. Whether you're searching for a relaxing island escape or an income-producing property, this is your chance to own in one of Siesta Key’s most desirable waterfront communities.

8911 Midnight Pass Road Unit 410, Sarasota

$415,000

1 Beds ⋅ 1 Baths ⋅ Casa Mar SubDv. ⋅ 34242 Zip Code

Nestled in the beachfront community of Casa Mar, this charming 1-bedroom, 1-bath condo offers the perfect blend of vintage character and island convenience. Featuring 600 sqft of living space + 108 sqft screened lanai, this light-filled unit is just steps from Siesta Key’s world-renowned white sand beaches. Inside, the open living area feels bright and airy with vaulted wood-beamed ceilings, natural light streaming through the sliding glass doors and multiple windows, a large storage closet, and timeless terrazzo flooring throughout. The cozy kitchen with solid surface counters opens seamlessly to the living space and located just off the lanai—perfect for enjoying morning coffee with a tropical view. The spacious bedroom provides ample storage, and the bathroom features a walk-in shower with clean finishes. Recent updates include a new A/C (2025), new building roof (2024), partial impact windows, and a new water heater in 2021. You’ll love the convenience of the assigned covered carport, located directly outside the entrance—no stairs, no hassle! Casa Mar features 200 feet of private deeded beach frontage with two covered pavilions, 2 community pools, a tennis & pickleball court, basketball hoop, and a clubhouse, 4 BBQ grilling areas with picnic tables, and laundry facilities. Amenities included in your condo fee: cable TV, internet, water/sewer, building insurance, and grounds maintenance. Short-term rentals (1-week minimum) are permitted—ideal for investment or personal use! And don't forget the Siesta Key Trolley stop right at the community entrance for convenient free rides on Siesta Key! Whether you’re seeking a personal getaway, seasonal escape, or income-producing vacation rental, this cozy Casa Mar condo offers endless possibilities—just steps from the Gulf of Mexico!

6006 Midnight Pass Road Unit 11, Sarasota

$420,000

2 Beds ⋅ 2 Baths ⋅ Midnight Cove Bayside SubDv. ⋅ 34242 Zip Code

If you're searching for deeded beach access and resort-style living on beautiful Siesta Key, this 2-bedroom, 1.5-bath condo could be your perfect match. Enjoy peaceful canal views and lush, mature landscaping in a community that remained untouched by flooding during recent hurricanes. The condo is in original condition and ready for your personal touch to transform it into your coastal retreat. Midnight Cove II offers deeded beach access and an impressive array of resort-style amenities, including a heated pool, tennis courts with pickleball nets, a basketball hoop, car wash station, barbecue grills, fitness center, and covered carport parking. Private docks are also available for your boat. Ideally located on Siesta Key, you'll be just steps from the pristine white sands of Crescent Beach and minutes from world-famous Siesta Beach. A quick ride brings you to Siesta Key Village, where you'll find lively restaurants, shops, and entertainment. Or take a short five-minute stroll to nearby dining and conveniences. Relax and embrace the Siesta Key lifestyle where every day feels like a vacation.

6350 Midnight Cove Road Unit 710, Sarasota

$450,000

1 Beds ⋅ 1 Baths ⋅ Aloha Kai Apts SubDv. ⋅ 34242 Zip Code

Siesta Key Aloha Kai One-story villa, just like new! Welcome to your slice of paradise on world-famous Siesta Key Beach! This stunning one-bedroom, one-bath villa offers the ultimate in coastal living with direct beach access. Enter into a fully remodeled interior, professionally remediated and redesigned from top to bottom, including stylish furnishings, so you can move right in or start renting immediately. Featuring luxury vinyl floors, private patio, barbecue grill, screened front lanai, new roof and turnkey furnished this condominium offers peace of mind and modern convenience. Short-term rentals allowed. On Siesta Key on Florida’s West Coast in Sarasota, this is a gated beachfront community on one of the top-rated beaches in the United States. Aloha Kai is a laid-back, friendly vacation community with a large swimming pool and direct access to the most spectacular beach on Florida’s Gulf Coast. A beach vacation destination with a laid-back vibe and plenty of places to relax or have an active getaway.

6020 Midnight Pass Road Unit 42, Sarasota

$440,000

2 Beds ⋅ 2 Baths ⋅ Sandy Cove SubDv. ⋅ 34242 Zip Code

Sold Data Only.

11 Sandy Cove Road Unit 8F, Sarasota

$464,000

2 Beds ⋅ 2 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code

Welcome to your slice of paradise on Siesta Key! This turnkey furnished 2 bedroom, 1.5 bathroom condo offers stunning canal views surrounded by mature tropical landscaping. With weekly rentals allowed and convenient in-house property management, it’s an ideal opportunity for both personal enjoyment and investment income. On-site property management provides professional oversight and streamlined rental operations. Positioned just steps from Siesta Key Beach, ranked the #1 beach in America, this property offers the ultimate coastal lifestyle in one of Sarasota’s most desirable locations. The unit is high and dry, and did not sustain flooding from recent hurricanes. Midnight Cove II conveniently features deeded beach access for effortless days in the sun. Resort-style amenities include a heated pool, tennis courts w/ pickleball nets, basketball hoop, car wash station, barbecue grills, fitness center, and covered carport parking. Enjoy the ultimate island lifestyle with Captain Curt’s, Daiquiri Deck, Anna’s Deli, and more right across the street, and Siesta Key Village is just minutes away for dining, shopping, and entertainment. With easy access to the mainland, downtown Sarasota’s vibrant arts, dining, and cultural scene is only minutes away. Rental income history is available upon request. Live on the #1 beach in the USA while your investment works for you - this is Siesta Key living at its finest.

1300 Cove Ii Place Unit 710, Sarasota

$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

$465,000

2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code

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. Whether as a year-round residence or a vacation retreat, this maintenance free villa on the Gulf side of Siesta Key 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

$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

$482,000

2 Beds ⋅ 2 Baths ⋅ Pointe On Midnight Pass SubDv. ⋅ 34242 Zip Code

Now available at the lowest price per square foot with a full bay view on South Siesta Key! Behind the gates to the southernmost tip of Siesta Key lies The Pointe, a quiet community that, by it’s own words, supports and enriches it’s owners quality of life. This fourth-floor unit offers the largest footprint available with engaging amenities. Start your day with a gaze over glimmering waters as the sun rises or soak up warm Florida sunsets as day fades to dusk. A clean, bright space, this beautiful space will accept your most personal aesthetic. A large kitchen with white cabinets and stainless appliances is where you can craft your creative cuisine. Abundant windows provide views from every room while allowing cheerful Florida sunshine to fill the generous, open concept living and dining room. Your primary suite is spacious with en-suite bath and access to the adjacent screened lanai. A second bedroom will comfortably accommodate your family or guests with a second bath that will nicely suit their needs. The lanai serves as a perch to drink in the view while considering your upcoming day or relaxing and counting your blessings after sunny Siesta Key adventures. An oversized laundry room is beyond convenient, as well as the premier parking spot for this unit just steps from the front of the building. Situated on over 5 acres of premier and gated Siesta Key property, find yourself immersed in an elevated lifestyle featuring exceptional amenities including a heated lap pool & spa, clubhouse, tennis & pickleball courts, fitness center, BBQ grills, boat docks and kayak storage, as well as onsite management. Every Siesta Key day offers local adventures including Turtle Beach, Crescent Beach, the lively Siesta Key public beach & park, the vibrant Siesta Key village, along with a plethora of shops and eateries. Venture a bit further and experience the lively cultural scene of downtown Sarasota, any number of barrier islands and their beaches, historical Venice, or one of the many gorgeous golf courses in and around the area. The quintessential Florida lifestyle can be yours here at The Pointe!

9397 Midnight Pass Road Unit 404, Sarasota

$460,000

2 Beds ⋅ 2 Baths ⋅ White Sands Village SubDv. ⋅ 34242 Zip Code

Make sure to see to this slice of paradise across the road from the beautiful ranked #1 Siesta Key Beach. This is being sold turnkey furnished all you need to do is bring your tooth brush. This condo has been updated and all of the appliances are within the last few years. The A/C has just recently been replaced. This complex did not have any flooding at all during the hurricanes and this unit is on the second floor. There is a wonderful screened lanai off the living room that looks over a lovely garden. This unit is nicely furnished with everything you would need at your new Beach condominium. Covered parking for one car and guest parking for other cars. The community amenities are wonderful they consist of an active clubhouse, a library, large swimming pool, extra laundry machines on property for your large items, BBQ grills and picnic areas and first come first serve boat docks and fishing area in a cove of the intercoastal. Having the Beach across the street offers, playgrounds, picnic areas, concession booths, volleyball, tennis and pickleball along with the lifeguard protected beach and swimming area. This is a pet friendly association as long as the pet is no larger than 25 pounds. The rental period is a minimum of 2 weeks all the way to year round. There is a management team on property to help with rentals and maintenance of the property. It is a well managed and well cared for complex.

5649 Midnight Pass Road Unit 804, Sarasota

$462,500

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

Second Floor CORNER END UNIT ON THE CANAL! This is the One You've Been Waiting For on Siesta Key, 2 bedroom 2 bathroom condo next to the Heated Pool and an easy walk across the street to our Private Beach Access through Crescent Arms! Welcome to this delightful, ready to move in 2-bedroom, 2-bath canal front condominium, ideally situated near the Stickney Point Bridge on Siesta Key. Easy on and off the island. Gorgeous granite countertops with a large open kitchen area including bar seating. Absolutely Stunning Porcelain floors throughout the kitchen, living area, bedrooms, hallway and entry. Gorgeous completely renovated bathrooms with Granite countertops in light brown tones and stunning showers. This condo has everything that you will need to move right in. If you are looking for a vacation home with a water view or retiring to a warm climate with a breeze - This is it! Dock your boat at our Harbor for a reasonable fee, clean your fish at one of the many Fishing Stations at our Harbor and enjoy the Deep Water Canal leading directly to the Sailboat Water of the Intracoastal Waterway. Have your morning coffee on the lanai and enjoy the breeze or close the Impact windows and work from your lanai with no distractions, just a breathtaking water view. You'll love how conveniently located you are to exceptional restaurants, Siesta Key Village and the natural beauty of Siesta Key Beach – an easy walk directly across the street. This condo boasts a spacious open floor plan adorned with extra windows since it is an end unit, bathing the dwelling in warm, natural light. The contemporary new flooring adds a classic touch to the layout. Among its foremost features, this unit comes with Impact Windows, a new Air Conditioner, a dedicated carport parking spot, outside storage space and enjoys amenities like a community pool, fitness center, and laundry on the second, third and fourth floors. Elevate your living experience in this beach home, and enjoy all the benefits and convenience it offers. Don't miss this chance to reside in one of the best locations in Sarasota! Active community with lots of activities in season, private beach access directly across the street. The location is wonderful, scat and trolley right outside your door, easy on and off the key, this is an over 55 community! Close to the Heated pool, clubhouse, Grills, outdoor spa, saunas, fishing pier on the Intracoastal Waterway with a great seating area, Exercise Room, Library and Shuffleboard Courts! This is a great community. You Deserve Paradise!

1250 N Portofino Drive Unit 208, Sarasota

$400,000

2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code

Live the Florida dream in this fully furnished, designer-finished 2 bedroom, 2 bathroom condo nestled within the coveted Siesta Harbor community, offering deeded beach access to world-famous Siesta Key Beach just across the street. Situated on the third floor with picturesque water views, this beautifully updated unit features granite countertops, white shaker cabinetry, stainless steel appliances, and newer laminate flooring throughout. Enjoy peace of mind with impact windows and custom plantation shutters, while the enclosed lanai with sliding glass windows provides a serene retreat year-round. The open-concept layout flows seamlessly from the modernized kitchen into a bright and welcoming living space, perfect for entertaining or relaxing. Both bathrooms have been tastefully renovated, including a fully remodeled guest bath, and the entire unit was freshly painted in 2025. Additional features include a private storage closet, updated lighting, and high-speed fiber optic internet. Siesta Harbor is a vibrant 55+ waterfront community along the Intracoastal Waterway, offering a heated pool, spa, clubhouse, fitness center, shuffleboard, fishing dock, kayak launch, BBQ area, and boat slips for up to 30’ vessels. Whether enjoying your morning walk to the beach, catching the free trolley to Siesta Key Village, or heading over the nearby bridge to explore downtown Sarasota’s dining, shopping, and cultural scene, this location offers the ultimate in coastal convenience and lifestyle. With monthly rentals allowed 12 times per year, it’s ideal as a personal escape or investment property. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**

1257 S Portofino Drive Unit 306, Sarasota

$370,000

2 Beds ⋅ 2 Baths ⋅ Inlet Apts SubDv. ⋅ 34242 Zip Code

Million Dollar Views at Half the Price.. Two Bedroom, Two Bathroom Corner End Unit... Discover the ultimate coastal retreat on the serene southern end of Siesta Key. This top-floor end-unit condo offers gorgeous partial Gulf views with coveted western exposure—perfect for soaking in breathtaking sunsets over the water. Just a short stroll to Turtle Beach and nestled along the picturesque Blind Pass saltwater canal, this hidden gem presents a rare opportunity to create your dream getaway. Though this unit is a fixer-upper, its unmatched location and incredible potential make it one of the best values on Siesta Key. Whether you’re seeking a personal sanctuary, a year-round residence, or a smart investment property, this condo offers the ideal foundation to bring your vision to life. Community Highlights: Boat-Friendly Living: Rentable boat slips available to owners and tenants on a 30-day rotation. Water Access: Dedicated kayak and paddleboard launch with secure storage. Peace of Mind: New seawall installed in 2022—proven resilient through the 2024 hurricane season. Resort-Style Pool: Recently resurfaced with new furniture, pump, and equipment. Outdoor Living: Brand-new community grill area, perfect for entertaining. Updated Exterior: Freshly painted in 2023 with a new roof added in 2024. Step into the laid-back charm of island living. Enjoy white-sand beaches and calm Gulf waters just minutes away. Explore local favorites in Siesta Village—home to vibrant restaurants, casual bars, and charming boutiques—all within walking or biking distance. Don’t miss this opportunity to own a slice of paradise. You can renovate the space to your taste, but this spectacular location is truly one-of-a-kind. Schedule your private showing today and start envisioning your future on Siesta Key!

9200 Midnight Pass Road Unit 30, Sarasota

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