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9226 Midnight Pass Road Unit 4A, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Castaway Cove SubDv. ⋅ 34242 Zip Code
Welcome to your boutique waterfront condominium community, Castaway Cove at the south end of Siesta Key. This is one of only eight condominiums, an end unit with a community boat slip and dock on a saltwater canal with quick access to the Gulf. Open floor plan with two bedrooms, two baths, great room and dining room views as well as a screened rear porch overlooking the canal and the Gulf. Enjoy sunsets watching the waves crashing on the beach and the manatees and dolphins splashing in your backyard. Grab a kayak and go for a perfect paddle through the mangrove tunnels or out Midnight Pass into the Gulf. Utilize the available kayak storage. New seawall and new roof on the building. The trolley is nearby and will take you right up the road to Siesta Beach or the Village. Yes, you can have it all on Siesta Key!

9226 Midnight Pass Road Unit 4A, Sarasota
7676 Midnight Pass Road, Sarasota
$800,000
Siesta Key SubDv. ⋅ 34242 Zip Code
An extraordinary opportunity awaits to create your own private waterfront oasis on world-renowned Siesta Key. Located at 7676 Midnight Pass Road, this expansive 0.43-acre cleared and level lot offers the ideal canvas for a custom coastal retreat that embodies tranquility, luxury, and the essence of island living. Positioned along the serene waters of Heron Lagoon, the property features approximately 111 feet of peaceful, protected waterfront—perfect for designing your own dock for kayaking, paddleboarding, or simply enjoying the beautiful views of the lagoon. The setting is quiet, secluded, and immersed in natural beauty, delivering a true sense of sanctuary. All just moments away from the dazzling white sands of Siesta Key Beach, consistently ranked the #1 beach in the United States for its powder-soft quartz sand, vibrant turquoise waters, and breathtaking sunsets. Here, you are close enough to stroll or bike to the shoreline yet tucked away in your own world of serene waterfront living. The lot is cleared, spacious, and ready to build, with utilities already available—offering a seamless start to designing your dream coastal estate without the delays of demolition or site preparation. This is truly a rare chance to craft your own slice of paradise on one of Florida’s most coveted barrier islands. Do not miss the opportunity to transform this exceptional property into the Siesta Key retreat you’ve always imagined.

7676 Midnight Pass Road, Sarasota
6300 Midnight Pass Road Unit 2, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Crystal Sands SubDv. ⋅ 34242 Zip Code
Experience the ultimate Siesta Key lifestyle in this beautifully renovated two-bedroom, two-bath end-unit villa just short distance from private Gulf and beach access. Offered turnkey furnished with stylish new décor, this 1,296-square-foot residence blends luxury and comfort with an open-concept layout, sun-drenched Florida room, and updated kitchen featuring quartz countertops, matching backsplash, soft-close cabinetry and stainless steel appliances. The spacious primary suite boasts a custom accent wall, wall-to-wall closet with designer glass doors, and a spa-inspired en-suite bath. The second bedroom is equally impressive, featuring an accent wall with slat wood acoustic panels and sliding closet doors with obscure glass inserts. Enjoy coastal living with new luxury vinyl plank flooring, blackout window shades, modern lighting, front-loading washer and dryer, attached one-car garage with epoxy floor, and guest parking. Crystal Sands is a well-maintained community with two pools, including one beachfront pool—and an on-site rental management company with weekly rentals permitted June through September and two-week minimum rentals October through May. This villa also includes exterior maintenance-free living, cable, internet, water, sewer and trash provided by the condominium association. Park the car and hop on the free Siesta Key trolley—just near your door—with service stretching from Turtle Beach to downtown Sarasota.

6300 Midnight Pass Road Unit 2, Sarasota
8779 Midnight Pass Road Unit 406H, Sarasota
$800,000
2 Beds ⋅ 3 Baths ⋅ Island Reef SubDv. ⋅ 34242 Zip Code
BEACH! BAY! ENJOY THE BAY VIEWS FROM THIS UPDATED REESIDENCE! IMPACT WINDOWS!! Kitchen with Granite countertop, stainless appliance, beverage refrigerator, two spacious bedrooms with private baths and walk-in closets. Powder room off foyer. Laundry in Residence. Turkey 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 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 406H, Sarasota
105 Island Circle, Sarasota
$800,000
Sarasota Beach SubDv. ⋅ 34242 Zip Code
This land is a RARE BEAUTY, are you dreaming of building your home where you and your family enjoy a lifestyle uniquely created for yourselves? IMAGINE a majestic home with a standalone guest house, alluring pool and gardens privately nestled among the palm trees. This property offers 2 lots, 0.45 acres / 19,456 sf. Palm Island is a community with only 298 homes where the residents enjoy gatherings in their Elsie Blair Park area. The main home had water intrusion from hurricane Helene which has been mitigated and could be rebuilt or torn down, consult your contractor for construction specifics. There is a Studio Unit/guest suite 576 hsf fully equipped with a full bath, kitchenette, sliding doors out to a large 120 sf wood deck above the detached 2 car garage. This would make a fabulous art studio, home office or in-law suite. The garage is a legal non-conforming space. Studio/Garage is block, consult your contractor for details. Take a stroll only 2 blocks to Siesta Key Beach and sink your toes into the luxurious quartz sand and sparkling water. The Village is minutes away where you will find fabulous restaurants, live music, specialty shops, night life, Sunday Farmers Market, art festivals and more. Take the Siesta Trolly to tour the island and beaches. You can also enjoy fishing, boating, parasailing, kayaking, swimming and snorkeling nearby. You are very close to downtown Sarasota, St. Armands Circle and Lido Beach are just across the Ringling Causeway Bridge. The Sarasota Airport, Asolo Repertoire Theater and Ringling Museum are all within minutes of your unique estate homesite. What a wonderful place to live and call home! Life is good at the Beach!!!

105 Island Circle, Sarasota
1235 Dockside Place Unit 108, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Harbour Towne SubDv. ⋅ 34242 Zip Code
“Living the Siesta Key Life” is waiting for you. BOAT DOCK AND DEEP- WATER BASIN.( 13,000 lb lift) Private single car garage too! This first floor 2-bedroom condo is totally updated, with a new kitchen, quartz countertops and breakfast bar, spacious bathrooms, custom doors and new beautiful easy-care tile throughout. This unit is selling totally furnished. Open floor plan for entertaining family and friends. The master has water views with sliding glass door for lots of light. The second bedroom enjoys a private tropical garden view. This community offers an amazing clubhouse, grills, large swimming pool, spa, tennis, pickleball courts and fishing pier. Walk to the crystal white sands and blue water of world-famous Siesta Key Beach and enjoy swimming, walking, sunning and reading in paradise. Walk or take the trolley to lively Siesta Key Village for dining in casual and formal restaurants, enjoy listening to live music.

1235 Dockside Place Unit 108, Sarasota
5250 Calle De Rio, Sarasota
$800,000
2 Beds ⋅ 2 Baths ⋅ Sarasota Beach SubDv. ⋅ 34242 Zip Code
Just a short two-block stroll from Siesta Key's vibrant village, you'll find yourself surrounded by a delightful array of casual and fine dining restaurants, lively shops, and bars with nightly live music. Yet, this charming home is nestled in a peaceful, quiet neighborhood; offering the perfect blend of convenience and tranquility. Enjoy the best of both worlds with a short walk or bike ride to the renowned Siesta Key Beach, and directly across from the Canal, where you can add your own private dock and launch your boat, kayaks, or paddleboards. Glide out to the Intracoastal and experience the water from your own yard! This home is spacious and inviting, with plenty of updates to enhance its charm! Upstairs, you'll find 2 bedrooms and 2 baths, including a recently remodeled kitchen with bright shaker-style cabinets and sleek quartz countertops. Skylights and large windows allow abundant natural light to pour in, making the entire home feel airy and bright. Cozy up by the real wood-burning fireplace in the open living and dining area, where the space flows seamlessly to the outdoors. Step out onto the large composite wood deck with modern aluminum railings, where you can enjoy tree-top views of the yard and canal—perfect for entertaining or relaxing. Off the kitchen, a second porch offers a peaceful retreat to sip your morning coffee while enjoying the sounds of birds singing. Downstairs you'll find your laundry room with a new washer and dryer, a new tankless water heater, and a large storage room. The additional bonus room would make an ideal place for a gym, game room, or media center. The beautiful, low-maintenance epoxy flooring keeps the downstairs bright and inviting. The large corner lot offers plenty of room to create your dream backyard, with ample space for a pool if you choose. The yard is perfect for hosting BBQs, oyster roasts, and making memories with friends and family. There’s also an extra storage shed beneath the second-story deck, keeping your lawn equipment out of sight and neatly organized. A concrete patio underneath adds even more entertaining space. Experience the relaxed, resort-style living you’ve always dreamed of—right in the heart of Siesta Key. Every day feels like a vacation in this coastal gem!

5250 Calle De Rio, Sarasota
1500 Cove Ii Place Unit 524, Sarasota
$796,000
3 Beds ⋅ 3 Baths ⋅ Midnight Cove Ii SubDv. ⋅ 34242 Zip Code
RARE OPPORTUNITY TO OWN A 3 BEDROOM ON SIESTA KEY! With Deeded beach access and one-week rentals! Maximize your investment while enjoying this fantastic 2 level townhouse in Midnight Cove II. Enjoy the views from your screened lanai or open air balcony on the second level. This unit offers space! Great sized living and dining areas, nice large, bright kitchen with updated appliances, powder room on the main level plus 2 more full baths upstairs. In unit laundry, deeded covered parking and offering a great rental history! Ideally located for quick deeded access to Crescent Beach just across the street! Midnight Cove II is a highly desirable community offering a marina with slips available and direct access to the intracoastal. Other amenities include tennis, pickleball, basketball court, fitness center and large heated pool. In addition, there is a grill and picnic area, car wash, pet walk, canoe storage and more! The property features beautiful mature landscaping with frontage on the intracoastal with paths and seating throughout the property. Midnight Cove II offers fully funded reserves, onsite rentals and management, and a rental friendly environment to maximize your income. Milestone Report is complete. Roof was replaced in fall of 2025 as well. Offered turnkey furnished with a small list of exceptions. Great opportunity - don't miss it!

1500 Cove Ii Place Unit 524, Sarasota
1087 Lake House Circle Unit C104, Sarasota
$795,000
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
See this Fabulous Beach Retreat w/Rental Income Opportunity Located Directly Across the Street from the #1 Ranked Beach in the USA! This incredible 2020 Fully Remodeled and Newly Furnished Condo is Steps Away from the Famous Siesta Key White Crystal Sandy Beaches and Turquoise Gulf Waters! UNIT FEATURES: 2 Large Bedrooms, 2 Fully Remodeled Baths, Great Split Level Floor Plan, Main Level includes the Living Room and Master Suite both with Long Lake Views and Balconies to Enjoy the Gulf Breezes and Beautiful Sunsets, Living Room and Master Suite have Vaulted Ceilings, Master Suite has a Fabulous Updated Master Bath w/Dual Shaker-Style Cabinets and Granite Counters, Walk-in Shower w/Beach Pebble Shower Floor, Spacious Dressing Area w/Built-in Closets; Upper Level includes Large Dining Room Overlooking the Living Room to the Lake Views, Elegantly Remodeled 2020 Light Bright Kitchen w/White Shaker-Style Cabinetry, Granite Counter Tops, Stainless Steel Appliances, Eat-in Kitchen Area, Pantry Closet, Laundry Closet plus a Slider to Balcony w/Sunset Views of the Tennis Courts; Split Plan Guest Bedroom Suite also includes a Balcony w/Views of the Tennis Courts, Remodeled Guest Bath w/Designer Tile, Granite Counter Tops and Combo Tub/Shower, 10' Ceilings, Brand New 2025 Tile Flooring on Main Level, One Car Garage on Ground Street Level w/Tons of Storage for Beach Chairs, TURNKEY FURNISHED w/Brand New Coastal Furniture, Home Sleeps 6 w/Sleeper Sofa, Paid in Full $60,000 for Brand New Impact Sliders, Impact Windows and Impact Garage Door to be installed in Spring of 2026, One Small Dog is Permitted for Owners. CONDO includes: Resort Style Amenities, Heated Pool, Tennis and Pickle Ball Courts and BBQ Pavilion. RENTAL FACTS: On-Site Rental Management Office Conveniently Available to take Advantage of the (52) Weekly Rental Program or Choose Your Own Airbnb Program. Owner Currently Books Rentals via Full Service Management through iTrip. Unit Income is approx $60,000 per year. COMMUNITY includes: Public Beach Access Across the Street w/Sand Volley Ball, Tennis & Pickle Ball Courts and Drum Circle. Siesta Key Trolly Transportation to Siesta Key Village is nearby to plenty of Restaurants, Bars, Ice Cream Shops and Boutiques. No Flood Damage to Unit.

1087 Lake House Circle Unit C104, Sarasota
1135 Lake House Circle Unit C115, Sarasota
$790,000
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
Welcome to your Siesta Key beach retreat! Perfectly positioned directly across from world-famous Siesta Key Beach, this immaculate, beautifully renovated 2-bedroom, 2-bath condominium offers the ideal combination of coastal luxury and exceptional investment potential. Completely renovated in 2019, this turnkey residence features recently installed hurricane-impact windows and sliding glass doors, a beautifully updated kitchen with stone countertops and stainless-steel appliances, a remodeled master suite, updated bathrooms, all-new PVC plumbing throughout, in-unit laundry, and a bright, open floor plan designed for easy beach living. Relax on your private lanai overlooking the tranquil lake or take a short walk to the powder-soft sands and crystal-clear waters of Siesta Key Beach. A rare attached private garage with epoxy floors provides additional convenience and storage. Residents and guests enjoy outstanding community amenities, including a pavilion with grills, an outdoor shower, a heated pool, tennis and pickleball courts, and beautifully maintained tropical grounds. Investors will appreciate the short-term rental flexibility, with both on-site professional property management and self-management options available, allowing owners to maximize rental income while maintaining complete flexibility. Whether you’re searching for a full-time residence, vacation getaway, or income-producing property, this condominium checks every box. Most furnishings are negotiable, offering the opportunity to purchase a fully furnished, turnkey property and begin enjoying or renting it immediately. Located just minutes from Siesta Key Village’s popular restaurants, boutique shopping, and entertainment, this is a rare opportunity to own a move-in-ready property in one of Florida’s most sought-after beach communities.

1135 Lake House Circle Unit C115, Sarasota
6236 Midnight Pass Road Unit 304, Sarasota
$790,000
2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code
Imagine the perfect Siesta Key getaway or income producing property - this is your opportunity to own at the exclusive Siesta Dunes Condominium. This turnkey furnished, updated two bedroom, two bath unit boasts an open floor plan and lovely views of the Gulf of Mexico. The kitchen is complete with high-end cabinetry, granite countertops and stainless-steel appliances. Relax in the large owner's suite, complete with a renovated bath, a large walk-in closet and access to the screened terrace. The second bedroom is generous in size and is the perfect place to host visiting guests. Set back from the walkway, this unit offers maximum privacy and easy access to the elevator. When you are not enjoying the beach chairs and lounges on the famous white sand beaches, luxuriate in the Gulf front circular pool that is the centerpiece of the property. This complex also is host to the beach side and garden BBQ grills, the beach deck and the pavilion, and the tennis/pickleball court. Utilizing the on-site property management company makes renting the property easy and carefree. Excellent rental history and income projections are available upon request. Don't miss this opportunity to own a move-in ready condominium in the heart of Siesta Key, centrally located near the shops and restaurants of Siesta Key Village.

6236 Midnight Pass Road Unit 304, Sarasota
6236 Midnight Pass Road Unit 1-307, Sarasota
$789,000
2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code
Welcome to Residence #307 at Siesta Dunes, a beautifully remodeled two-bedroom, two-bath condominium located directly on world-famous Siesta Key Beach with views of the Gulf from the lanai and the primary bedroom. Offering 1,250 square feet of comfortable coastal living on the third floor, this turnkey furnished residence is ready to enjoy from day one — whether as a personal beach retreat, full-time residence, or investment property. Inside, the home has been thoughtfully decorated with a relaxed, sophisticated coastal feel. Crown molding adds a finished touch throughout, while the remodeled kitchen features granite countertops, stainless steel appliances, glass tile backsplash and a clean, functional design that makes everyday living and entertaining easy. The spacious living area opens to an enclosed lanai surrounded by lush garden views, creating a peaceful place to enjoy morning coffee, read, or unwind after a day at the beach. The lanai is enclosed with hurricane-resistant sliders, and the primary suite features hurricane-resistant windows for added peace of mind. The primary bedroom also includes a walk-in closet, and views of the Gulf. The convenience of an in-unit stackable washer and dryer hook up makes this residence especially easy to live in and enjoy. Additional features include an assigned covered carport located close to the building, private storage closet, ample guest parking, and access to the building elevator. Siesta Dunes is a gated beachfront community known for its resort-style amenities and beautifully maintained grounds. Residents and guests enjoy a heated pool and spa, beachside deck, pavilion, clubhouse, tennis courts, and direct access to one of the most celebrated beaches in the country. The on-site property management company also helps make renting the property simple and convenient. With strong rental-income potential, two-week minimum rentals from January 15 through the end of April, and one-week minimum rentals the rest of the year, this condominium offers a compelling combination of lifestyle and investment opportunity. Enjoy it for your own vacations, create a family beach tradition, and rent it when you are not using it. Perfectly positioned on Siesta Key, this location makes it easy to enjoy Sarasota’s exceptional dining, shopping, arts, and entertainment, while coming home to the powdery white sand, clear Gulf waters, and unforgettable sunsets that make Siesta Beach so special. Whether you are looking for a vacation getaway, income-producing property, or a place to build lasting memories, Residence #307 at Siesta Dunes offers the best of beachside living.

6236 Midnight Pass Road Unit 1-307, Sarasota
6063 E Peppertree Way Unit 111, Sarasota
$785,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
First-Floor Bayfront | No Stairs | Full Bay Views | Outdoor Patio. Enjoy effortless coastal living in this like-new, fully rebuilt residence (from the studs in), featuring all-new electrical, plumbing, HVAC, insulation, interior wall soundproofing, hurricane-impact windows, and five-year warranties on major appliances. HOA includes building and structural insurance, and internet/cable. Home has one assigned parking spot directly in front, and plenty of guest parking. Offered fully furnished and professionally styled—including electric shades, artwork, and accessories—this 2-bedroom, 2-bath home is truly turnkey and rental-ready with linens, kitchenware and more. Ideally positioned on the Intracoastal Bayfront, enjoy sweeping water views, passing boats, stunning sunsets, and fishing from the dock—or just enjoy your outdoor patio. Inside, the light-filled open layout showcases high-end finishes and a seamless flow between kitchen, living, and dining spaces. Spacious bedrooms provide private retreats, including a serene primary suite with a spa-like bath. Resort-style amenities include two heated pools, pickleball/tennis courts, fitness center, and two clubhouses with on-site rental capabilities. Private beach access is just an 8-minute walk to Siesta Key’s world-famous sands—offering the best of bayfront tranquility and Gulf access. Ideal as a full-time residence, vacation home, or income-producing property. Never been slept in, be the first to enjoy. No pending special assessments.

6063 E Peppertree Way Unit 111, Sarasota
1201 E Peppertree Drive Unit 234, Sarasota
$775,000
3 Beds ⋅ 3 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Private end-unit residence at Peppertree Bay with outdoor patio space, lush tropical landscaping, and an easy stroll to the bayside community pool from the back door. Inside, you’ll find extensive renovations and updates throughout, including new flooring, doors, fans and fixtures, walls, baseboards, and cabinetry. Major system improvements have also been completed, including waste lines, A/C, appliances and washer, dryer. Both the primary and guest baths have been updated along with a major enhancement to the kitchen. The 1st and 2nd floor lanai windows have been recently replaced—bringing in light while providing enhancing comfort and extended living space. A rare combination of privacy, thoughtful upgrades, and that classic Peppertree Bay lifestyle on Siesta Key. Must see and easy to show.

1201 E Peppertree Drive Unit 234, Sarasota
1200 E Peppertree Lane Unit 601, Sarasota
$775,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Experience elevated coastal living in this stunning penthouse residence at 1200 E Peppertree Drive, Unit 601. Perched atop the building, this exceptional unit offers breathtaking panoramic views of the Intracoastal Waterway and downtown skyline, creating a spectacular backdrop from sunrise to sunset. Completely renovated with impeccable attention to detail, the residence features custom built-ins, high-end finishes, and a thoughtfully designed layout that blends style and functionality. The open living spaces are bathed in natural light, maximizing the views and enhancing the penthouse feel throughout. Located in the highly desirable Peppertree Bay, a rare gulf-to-bay community with deeded beach access, residents enjoy resort-style pools on both the Gulf and Bay sides, lush tropical grounds, and exceptional amenities. Just steps from world-famous Siesta Key Beach and minutes to dining, shopping, and entertainment, this is a rare opportunity to own a move-in-ready penthouse offering luxury, views, and the ultimate island lifestyle.

1200 E Peppertree Lane Unit 601, Sarasota
6236 Midnight Pass Road Unit 300, Sarasota
$771,250
2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code
Experience coastal living at its finest in residence #300 at Siesta Dunes, ideally on renowned Siesta Key Beach. This meticulously remodeled two-bedroom, two-bath condominium offers 1,150 square feet of luxurious living space on the third floor, providing a tranquil ambiance and a sense of escape. Crown molding accents the professionally decorated interior, creating a sophisticated atmosphere. Sold turnkey furnished, this residence offers a seamless transition into upscale beachside living. Go inside to find chiseled travertine tile flooring throughout, adding natural coastal charm. The chef’s kitchen is equipped with granite countertops, stainless steel appliances and maple cabinetry, blending style and functionality. French glass doors open to a private lanai terrace surrounded by lush garden views. The lanai is enclosed with hurricane-resistant sliders, while the primary suite features hurricane-resistant windows for added peace of mind. The primary suite also includes a custom-organized walk-in closet, enhancing storage and convenience. A convenient stackable washer and dryer are in the unit. Additional features include an assigned covered carport, a private storage closet, ample guest parking and access to the building elevator. Siesta Dunes is a gated community offering a wealth of resort-style amenities, including a heated pool and spa for year-round enjoyment, a beachside deck, pavilion, clubhouse, and tennis and pickleball courts. Utilizing the on-site property management company makes renting the property easy and carefree. With excellent rental potential, two-week minimum stays from January 15 through the end of April and one-week minimums the rest of the year, this condominium is a compelling investment opportunity as well as a personal retreat. Siesta Dunes is in a good location, making it easy to explore Sarasota’s world-class dining, shopping and entertainment. Siesta Key Beach is just a short distance away, recently named the No. 1 beach in America by TripAdvisor. Renowned for its powdery white sand, clear waters and stunning sunsets, it’s no wonder Siesta Beach is considered the pinnacle of coastal living. Whether you seek a full-time residence, a luxurious vacation retreat or a high-value investment, this extraordinary property exemplifies the best of gulf-front living.

6236 Midnight Pass Road Unit 300, Sarasota
1055 W Peppertree Drive Unit 102AA, Sarasota
$770,000
2 Beds ⋅ 2 Baths ⋅ Peppertree Bay SubDv. ⋅ 34242 Zip Code
Rare opportunity to own one of the most resilient and desirable residences on Siesta Key! This 2-bedroom, 2-bath condominium offers 1,163 square feet of living space (1,462 gross square feet) and is ideally positioned on the west side of the building on an elevated first floor, approximately 15 feet above sea level. It is also the closest high-rise condominium to the beach, offering exceptional proximity to the Gulf. One of only six residences in the building with an expansive deck, this sought-after middle-unit location provides a truly rare outdoor living experience. The oversized deck offers ample space for dining, entertaining, or simply relaxing while enjoying coastal breezes and sunsets. The residence has demonstrated remarkable storm resilience, sustaining no damage through three major hurricanes. This is attributed to its elevated positioning, protected west-side exposure, and six hurricane-rated doors installed in 2021. Recent interior upgrades enhance both style and comfort, including luxury vinyl flooring and freshly painted walls completed in 2025. The refrigerator, washer, dryer, and garbage disposal were also replaced in 2025. A dedicated parking space conveys with the unit. Owned by the same family since 1976, the home reflects decades of pride of ownership and thoughtful care. The community features two pools and two clubhouses on both the Gulfside and Bayside, along with a Gulfside fitness center. A well-managed rental program offers flexibility for owners while preserving a relaxed residential atmosphere. Located in one of Florida’s most coveted coastal settings, this exceptional residence offers a rare blend of scarcity, storm resilience, expansive outdoor living, and resort-style amenities—making it an outstanding lifestyle choice and investment opportunity.

1055 W Peppertree Drive Unit 102AA, Sarasota
6236 Midnight Pass Road Unit 305, Sarasota
$770,000
2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code
Rarely for sale TURNKEY FURNISHED beach condo at Siesta Dunes, where living the Siesta Key lifestyle comes naturally. Enjoy true convenience with DIRECT BEACH ACCESS to powdery white sand and the sparkling Gulf- no streets to cross, just a short, breezy walk to the beach, pool, hot tub, or tennis court right within the community. With onsite management available and WEEKLY RENTALS allowed, owning and renting is refreshingly simple. Whether you're strolling to dinner, biking to the Village, or simply putting your toes in the sand, every moment here feels effortless. Lovingly maintained by the same owner for 40 years, this residence shines with thoughtful updates, brand-new IMPACT WINDOWS for added peace of mind, and even a gorgeous blue Gulf VIEW from your primary bedroom. Whether you're looking for a smart investment or a sunny place to call home, this Siesta Dunes gem is ready to welcome you!

6236 Midnight Pass Road Unit 305, Sarasota
108 Whispering Sands Drive Unit V26, Sarasota
$762,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
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108 Whispering Sands Drive Unit V26, Sarasota
4894 Oxford Drive, Sarasota
$762,000
3 Beds ⋅ 3 Baths ⋅ Siesta Bayside SubDv. ⋅ 34242 Zip Code
POOL HOME!! Priced To Sell!! Nestled on the peaceful tranquil island of Siesta Key, renowned for its world-class beach and romantic sunsets. JUST MINUTES FROM Siesta Beach & Village. This is the most wonderful place to embrace island-style living. This north island location on a quiet canopy street is walkable to the village, beach, and renowned Out-of-Door Academy. This 3 Bedroom and 2 & 1/2 Bathroom home is ready for your personal touches. Enjoy relaxing in your Caged Pool & Patio area. This Single family home has approximately 1834 sq.ft. +/- living area and a 2 car garage. The existing home—professionally remediated after flood damage—presents a unique opportunity for those looking to reimagine or completely rebuild. Almost 13,000 sq.ft lot with luscious natural landscaping and mature oaks. Updated roof in late 2019.

4894 Oxford Drive, Sarasota
5144 Oxford Drive, Sarasota
$750,000
2 Beds ⋅ 2 Baths ⋅ Siesta Beach SubDv. ⋅ 34242 Zip Code
Build New or Major Redevelopment Near Siesta Beach. Large lot located just minutes from Siesta Beach in a well-established Sarasota neighborhood close to Siesta Key, shopping, and dining. County records indicate the property includes two platted lots of record (Lots 9 and 10). The existing structure has sustained significant damage; renovation may be possible, but is not likely. The property is best suited for new construction or substantial redevelopment, with value primarily in the land and location. Property is being sold as-is.

5144 Oxford Drive, Sarasota
1325 S Portofino Drive Unit 310, Sarasota
$750,000
2 Beds ⋅ 2 Baths ⋅ Siesta Harbor SubDv. ⋅ 34242 Zip Code
Welcome to the exclusive Pompano building, a well-maintained non?55+ community set within the highly sought after Siesta Harbor.. This 2 bed 2 bath, completely remodeled end unit has a wrap around balcony that provides endless views of the ocean and the Intracoastal waterway. Custom kitchen with quartz countertops wood cabinetry with glass inserts, and 2 beautifully renovated bathrooms. Significant amount of storage. 2 month rentals, no pets, washer and dry is common and is located in the corridor right outside your front door. Association fees includes Cable, Water, Trash, Sewer, Internet, Common area taxes, Community Pool, Fitness center, Escrow Reserves Fund, Insurance, Maintenance Exterior, Maintenance Grounds, Manager, Pool Maintenance, Trash.

1325 S Portofino Drive Unit 310, Sarasota
4822 Ocean Boulevard Unit 2A, Sarasota
$750,000
2 Beds ⋅ 2 Baths ⋅ Siesta Towers SubDv. ⋅ 34242 Zip Code
Price Improvement! Your Coastal Paradise Awaits! Step into a world of elegance and tranquility in this stunning condominium, perfectly situated along the breathtaking coastline of Siesta Key. Featuring two lavish ensuite bedrooms, this residence offers you the ultimate in coastal living. The primary bedroom boasts full panoramic views of the crystal blue waters of the Gulf, complete with a beautifully remodeled bathroom and an expansive walk-in closet designed for the modern lifestyle. Embrace a split floor plan that promotes privacy and relaxation, all within a breezy coastal open-concept design that floods the space with an abundance of natural light. Indulge in the outdoors from two covered balconies, ideal for outdoor dining or savoring a glass of rosé as you watch the sun dip below the horizon in a stunning display of colors. Enter the building through a well-appointed lobby that exudes sophistication and class. Residents enjoy a host of resort-style amenities that include a beautifully remodeled community center for exclusive use, a newly refurbished workout facility, and a gulf-front pool to soak in the sun. The outdoor BBQ area is perfect for gathering with friends and family, while storage for beach accessories and bikes adds to the convenience of a coastal lifestyle. Enjoy the peace of mind that comes with covered parking. Perfectly located, this luxury community allows you to walk, bike, or cruise your golf cart to local restaurants, boutique shopping, live music venues, and the vibrant farmers market, all within minutes from your doorstep. Of course, the soft, white sands of Siesta Key Beach are just a short stroll away, ready to fulfill your beach daydreams. Don't miss your chance to experience luxury coastal living at its finest. Schedule your private tour today and discover your new home in paradise!

4822 Ocean Boulevard Unit 2A, Sarasota
19 Whispering Sands Drive Unit 203, Sarasota
$750,000
2 Beds ⋅ 2 Baths ⋅ Whispering Sands SubDv. ⋅ 34242 Zip Code
Opportunity Awaits with a Million-Dollar View! Imagine starting with a blank canvas and creating your very own slice of paradise—complete with private beach access and unobstructed Gulf views. Welcome to this light-filled 2 bed / 2 bath residence in the coveted North Tower of Whispering Sands, a premier 55+ Gulf-front community. Perfectly perched on the 2nd floor, this home captures sweeping vistas of shimmering turquoise waters, sugar-white sands, endless sky, and lush tropical greenery. Step onto your private balcony—accessible from both the living room and primary suite—and be mesmerized by the soothing rhythm of the surf and the kaleidoscope of Florida sunsets that paint the horizon each evening. This is your front-row seat to the Gulf Coast lifestyle. Dream away!

19 Whispering Sands Drive Unit 203, Sarasota
6140 Midnight Pass Road Unit 103, Sarasota
$750,000
1 Beds ⋅ 1 Baths ⋅ Horizons West SubDv. ⋅ 34242 Zip Code
Experience the ultimate island lifestyle in this TURNKEY FURNISHED, west-facing condo at Horizons West—just steps from your private Siesta Key beach! This spacious 1-bedroom retreat boasts over 1,000 sq. ft., soaring ceilings, and a wall of oversized windows framing breathtaking panoramic Gulf, beach, resort pool and sunsets sunset views, including dolphin sightings. Enjoy an open, airy floorplan with a designer kitchen featuring stone countertops, stainless appliances, and a breakfast bar. Relax in the king-sized bedroom with custom California Closets, or host family and friends on the living room sleeper sofa. Recent upgrades include impact windows/doors, 2020 AC, and 2021 water heater. Resort-style amenities abound: 300 ft. of private beach, two pools, spa, cabanas, grills, and a bayside park with day dock. Plus, private carport storage for all your beach toys! Hop on the free Siesta Key trolley for world-class dining and shopping. Come see why Siesta Key is ranked #1 Beach in the USA and #4 in the world—your piece of paradise awaits! View the Video: https://youtu.be/5NK5aBPx5vM

6140 Midnight Pass Road Unit 103, Sarasota
266 Ogden Street, Sarasota
$740,000
3 Beds ⋅ 2 Baths ⋅ Siesta Rev SubDv. ⋅ 34242 Zip Code
Investor Opportunity on North Siesta Key! Located within City of Sarasota city limits! This hurricane-impacted property presents a rare chance to acquire a premium piece of real estate in one of Sarasota’s most sought-after coastal markets. Situated on a generous 0.31-acre corner lot on the quiet residential north end of Siesta Key, this 3-bedroom pool home offers exceptional potential for renovation, redevelopment, or a custom luxury rebuild. With strong underlying value driven by location, investors and builders will appreciate the property's proximity to Siesta Key Beach, Siesta Village, waterfront dining, and shopping, while still enjoying the privacy and charm of an established island neighborhood. Large corner lots in this area are increasingly difficult to find, making this an attractive opportunity for those seeking long-term appreciation or resale potential. Whether your vision is a high-end coastal residence, a profitable renovation project, or a complete redevelopment, the possibilities are significant. Opportunities to purchase on North Siesta Key at a value-add price point are becoming increasingly rare. Bring your contractor, architect, and imagination—this is your chance to capitalize on one of Florida’s most desirable barrier island locations.

266 Ogden Street, Sarasota
1055 Beach Road Road Unit B204, Sarasota
$735,000
2 Beds ⋅ 2 Baths ⋅ Our House At The Bch SubDv. ⋅ 34242 Zip Code
Welcome to Our House on the Beach, one of Siesta Key’s most desirable communities located directly across from world-famous Siesta Key Public Beach. This well-maintained 2-bedroom, 2-bath weekly rental residence features a spacious layout with two oversized private patios overlooking the heated community pool and spectacular west-facing sunsets. Thoughtfully cared for over the years, this condo is move-in ready and offers an ideal opportunity for light updating to make it your own coastal retreat. A major upgrade is already underway—brand-new, storm-rated impact windows and sliding doors are being installed in the coming days, and are fully paid for by the seller, offering peace of mind, energy efficiency, and improved storm protection for years to come. Additional highlights include updated bathrooms and a rare covered parking space conveniently located and protected from the elements—a highly sought-after feature on Siesta Key. Residents enjoy resort-style amenities including a heated pool, two tennis courts, golf cart parking, elevators, and bike storage. Located on Siesta Key, known for its world-famous quartz sand beach, vibrant Village, outdoor recreation, and relaxed Gulf Coast lifestyle, this condo is centrally positioned on the island and just moments to Siesta Key Village, and a short drive to mainland shopping, groceries, healthcare, and the arts and dining scene of downtown Sarasota. A prime island location, strong community amenities, and outstanding value—this is the Siesta Key lifestyle you've been waiting for.

1055 Beach Road Road Unit B204, Sarasota
6204 Midnight Pass Road Unit 201, Sarasota
$735,000
2 Beds ⋅ 2 Baths ⋅ Siesta Dunes Beach SubDv. ⋅ 34242 Zip Code
Virtually staged to showcase the full potential of this beautiful Siesta Key condo! Just steps from the powdery sands of Siesta Key Beach, this turnkey 2-bedroom, 2-bath unit offers the perfect blend of comfort, style, and value. The unit features vaulted ceilings that create a spacious feel, along with a covered parking space and private storage area. New hurricane-impact windows and doors have already been purchased and are scheduled for installation, providing added peace of mind for future owners. A new roof is also coming soon. This unit has no history of flood damage during current ownership and delivered strong rental income in 2023, generating $62,000 net in just 9 months as the owners reserved 3 months for personal use. Residents and guests enjoy access to resort-style amenities including a clubhouse, sparkling pool, tennis courts, and 24-hour security. Owners also benefit from maximum rental flexibility with the option of short-term rentals through Airbnb, VRBO, or the on-site rental office. Plus, you are just moments from Siesta Key’s top restaurants, bars, and boutique shops. Whether you are seeking a stress-free getaway or a high-performing property, this condo checks every box: location, lifestyle, and long-term value.

6204 Midnight Pass Road Unit 201, Sarasota
717 Treasure Boat Way, Sarasota
$735,000
2 Beds ⋅ 2 Baths ⋅ Siestas Bayside Waterside SubDv. ⋅ 34242 Zip Code
Looking for the perfect slice of Siesta Key paradise to make your own? This 2 bed/2 bath home is situated on just over ¼ acre lot with majestic trees offering shade, privacy and tons of character. The newly carpeted living room opens up to the Florida Room for the perfect marriage of indoor/outdoor living. An oversized screened patio just off the kitchen provides the perfect opportunity for alfresco dining. Both bedrooms are ensuite with fresh new carpeting while the primary has the added benefits of a walk-in closet, dual sinks with a vanity and maximum privacy due to the split floor plan. There is a dedicated laundry room with cabinetry and a desk if office space is needed. The circular driveway and 2 car garage provide plenty of parking. For families the highly rated Out-Of-Door Academy is just a few blocks away for Pre-K through Grade 5. The #1 Siesta Key Beach is located approximately 1 mile from the front doorstep. And the popular Siesta Village with a variety of dining and shopping options is even closer!

717 Treasure Boat Way, Sarasota
5600 Beach Way Drive Unit 315, Sarasota
$730,000
2 Beds ⋅ 2 Baths ⋅ Beachway Apts SubDv. ⋅ 34242 Zip Code
Your Florida beach escape awaits — and with a motivated seller, this is an opportunity you won't want to miss.... take a look at this condo that is steps away from the quartz crystal white powdery sands and warm Gulf waters of the award-winning Siesta Key Beach? This wonderfully located turn-key, furnished end unit condo is oh so unique on the top floor with views of the beautiful white sandy beach and sparkling blue Gulf waters, a rare, remodeled find on the spectacular Gulf coasts of Florida! The rental income is excellent! This recently, completely remodeled from ceiling to floor, wall to wall, unit has 2 bedrooms, 2 bathrooms, hard flooring throughout, a sprawling island, quartz countertops, impact windows and sliders, AND has a spacious balcony, ready for you to relax and enjoy. This unit transfers with $50,000 in furnishings and furniture. This is a perfect place for you to have your dream of a beach life come to reality, with the potential of using it to generate income with monthly rentals. This amazing mid-rise condominium community offers a heated community pool, outside grills, a clubroom with a kitchen, plenty of guest parking and a laundry room on each floor. Recent improvements include newer roofs 2020, a newer elevator 2019, re-plumbed stacks 2018, refreshed landscaping 2020, and new vinyl fencing 2021. The quarterly fee includes access to the heated community pool, basic cable, water/sewer, pest control, weekend on-site maintenance person, and community insurance. Enjoy convenient access to Siesta Key Beach and to Siesta Key Village shops and restaurants with the free trolley service that stops right in front of the Beach Way community, or, walk, orrrrr take a bike cruise to many nearby shops and restaurants… You are not only buying a beach property, you are buying a lifestyle in the beautiful Southwest Florida Sun. This unit can be your own sanctuary escape and your retirement investment... Come see, come sigh and make this Siesta Key lifestyle in the Sun your own.

5600 Beach Way Drive Unit 315, Sarasota