Location: Sarasota , 34242
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915 SEASIDE DR #310, SARASOTA, FL 34242
$1,399,00030 Days on yellowkey MLS ID: A4686908
0 Days Off yellowkey (back on 4/20/2026)
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1900 Built: 2009 Tax: $14,651 (2025)Community: Siesta Key Beach Residences IiSpa: YesCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$14,651
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. Welcome to Unit 310 at the exclusive Hyatt Residence Club Siesta Key Beach—where elevated coastal living meets one of the most sought-after addresses on Siesta Key. Set directly on the powdery white sands of world-renowned Siesta Key Beach, this premier residence offers a rare opportunity to own within a luxury, resort-style community backed by the trusted Hyatt brand and known for its exceptional service, amenities, and strong rental demand. This beautifully updated 3-bedroom, 3-bath condominium is currently utilized as investment property and professionally managed offering a seamless, turnkey experience designed to maximize both convenience and performance. Perfectly positioned on world-famous Siesta Key Beach—consistently ranked among the top beaches in Florida, the U.S., and the world—this property benefits from steady, year-round demand for high-end vacation rentals. Whether you're seeking a dedicated income-producing asset, a future vacation retreat, or a combination of both, Unit 310 offers exceptional flexibility and long-term value. Inside, the residence features a bright, open-concept layout with three bedrooms and three full bathrooms, designed to comfortably accommodate owners and guests. Spacious living and dining areas create a welcoming environment, while the private lanai offers an additional space to relax. Residents and guests enjoy access to resort-style amenities, including a sparkling pool, fitness center, concierge services, and professional management options. With direct beach access, close proximity to Siesta Key Village, and strong, consistent rental appeal, Unit 310 presents an exceptional opportunity in the Siesta Key market. Positioned as one of the best values currently available, it is competitively priced to sell—making it an ideal choice for both investors and end users looking to capitalize on location, lifestyle, and long-term potential.
Listing is courtesy of: THE SARASOTA REAL ESTATE COMP. (941-321-5595)
Listing Agent: David Lehrman (941-321-5595)
5968 MIDNIGHT PASS RD #158, SARASOTA, FL 34242
$760,00083 Days on yellowkey MLS ID: A4681104
1 Days Off yellowkey (back on 4/20/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1134 Built: 1975 Tax: $7,449 (2025)Community: Palm Bay Club IiiCondo
Taxes:$7,449
Elementary School: None
High School: None
Middle School: None
Remarks: Under contract-accepting backup offers. Looking for the perfect 2-bedroom, 2-bath investment beach condo on Siesta Key? This second-level residence presents a strong income-producing opportunity at the desirable, gulf-front Palm Bay Club. Ideally situated on the beach side of Midnight Pass Road, unit #158 features a comfortable coastal design with an open floor plan, beachy ambiance, and tile flooring throughout, making it move-in ready for owners, guests, and short-term renters alike. Just steps from the pristine blue waters and powder-white sands of Siesta Beach, the thoughtfully designed and tastefully furnished interior maximizes space and functionality with seamless flow from the kitchen to dining and living areas. One of the premier beach-to-bay communities on Siesta Key, Palm Bay Club offers an exceptional array of amenities including two heated swimming pools, a hot tub overlooking the bay, fitness center, lighted tennis court with two pickleball courts, BBQ grills, a fishing pier, and boat docks available for daily rental. With a rare three-night minimum rental policy on Siesta Key and onsite management, this is an outstanding opportunity for the savvy owner-investor seeking both lifestyle and income.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Jonathan Abrams (941-232-2868)
7324 POINT OF ROCKS RD, SARASOTA, FL 34242
$16,000,000395 Days on yellowkey MLS ID: A4643281
Bed: 5 Bath: 5.0 Gar: 4 Liv Area Sq Ft: 5524 Built: 2025 Tax: $32,550 (2024)Community: White Beach Fruit Co PropSpa: YesSingle Family
Taxes:$32,550
Tax Year: 2024
Remarks: Under Construction. Newly completed Gulf-front coastal contemporary home on prestigious Siesta Key by Murray Homes. This 5BR/5BA/1HB residence offers approx. 5,500 sq. ft. of living space plus 2,600 sq. ft. of recreational non-conforming space. Features include a gourmet kitchen with large island, walk-in pantry, wine refrigerator, and built-in coffee system, opening to a spacious great room with fireplace. Smart home technology, high-end lighting, and whole-house generator. Outdoor living includes Gulf-front pool and spa with beach shelf, expansive deck, summer kitchen, fireplace, and lounge areas. Upstairs lounge with vaulted wood ceilings and beverage refrigerator, plus 4 en-suite bedrooms, many with Gulf views. Primary suite with soaking tub, oversized shower, and dual vanities. Private beach on a secluded street with panoramic Gulf views. 4-car garage plus golf cart/kayak garage
Listing Agent: Karen Chandler (941-544-4919)
5830 MIDNIGHT PASS RD #T22, SARASOTA, FL 34242
$1,000,00020 Days on yellowkey MLS ID: A4689210
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1194 Built: 1967 Tax: $8,543 (2025)Community: Jamaica Royale Elev AptsCondo
Taxes:$8,543
High School: Riverview High
Remarks: Rare opportunity - Jamaica Royale, Tower 1 Enjoy breathtaking Gulf views from this beautifully positioned second-floor Gulf front condo on world-famous Siesta Key Beach. This 2-bedroom,2-bathroom residence features light-filled open living and dining space. The generous areas flow effortlessly toward the Gulf creating the perfect setting for relaxed coastal living or entertaining guests. Enjoy spectacular sunsets from the expansive balcony accessible from both the living room and primary suite. Ideally located just minutes from the island's vibrant restaurants, boutique shopping and entertainment, this Jamaica Royale beauty is a MUST SEE! Whether as a primary residence, a beach retreat or an investment opportunity this condo offers the best in Gulf front living.
Listing Agent: Alana Kate Sudano (410-456-8783)
157 GARDEN LN, SARASOTA, FL 34242
$1,195,00048 Days on yellowkey MLS ID: A4685180
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2146 Built: 1958 Tax: $9,961 (2025)Community: Siesta Rev OfSingle Family
Taxes:$9,961
Remarks: Under contract-accepting backup offers. Gorgeous remodel in the heart of Siesta Key and a short walk to Shell Beach access. Located a very large corner lot on a dead end street this home has the space, size, and all the amenities for your perfect getaway. This home has character and charm in all ways. From the banyan and palm trees, to the privacy wall, brick walkway, custom gates, and lush landscaping surround your Siesta getaway. This home, BIG PASS HIDEAWAY, a very successful vacation rental in previous years has generated over 105-112k consistently at a 73% occupancy rate. Completely renovated, designer touches, this home is gorgeous. Retro terrazzo floors, Gas fireplace, wood beam ceilings, European designer cabinets, just a few of the touches that bring out the style of this home. 3 main bedrooms and a 4th room connected to the main bedroom to create a double ensuite for the main bedroom that can be used as anything you wish. Currently set up as 4th bedroom with separate access to the pool area, it could easily be a studio, workout room, a nursery, a reading lounge. It's a special feature. As far as the improvements, everything has been completely redone. All new AC's main and mini split, new duct work. All repainted, new kitchen cabinets, new appliances, bathrooms renovated with designer tile. All new wiring, house was replumbed with new stacks and lining in main drain. ALL NEW HURRICANE IMPACT DOORS AND WINDOWS. New Pebble tech pool finish. Roof is 6 years old. New irrigation pump. Low voltage lighting. Tons of outdoor spaces from the oversized pool, to the garden and grilling areas. Hangout on the screened in patio or enjoy the firepit area. Lose track of time on your Florida visits and drift down the street to Siesta Key village and enjoy all it has to offer from shops, to dining, to the best beach USA! This home is gorgeous and priced to sell. Generate income. The choice is yours. Absolutely nothing to do but move and enjoy the siesta key life. Live in it. Schedule your private showing today. ***Can be purchased turnkey fully furnished on a separate bill of sale.***
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Joseph Patoray, Llc (941-448-8971)
306 ISLAND CIR, SARASOTA, FL 34242
$1,825,00015 Days on yellowkey MLS ID: A4689514
0 Days Off yellowkey (back on 4/19/2026)
Bed: 4 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2392 Built: 1952Monthly Fee: $4 Tax: $18,781 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$18,781
Remarks: Under contract-accepting backup offers. A truly rare offering, this waterfront residence is uniquely positioned with 133 feet of water frontage on two sides, creating an unparalleled sense of privacy and serenity. Nestled on prestigious Palm Island, in the heart of Siesta Key, this property embodies the ultimate coastal lifestyle. This spacious four-bedroom, three-bathroom home is thoughtfully designed, featuring two en-suite bedrooms alongside two additional generously sized guest rooms. Expansive windows invite in natural light while framing tranquil water views throughout the home. Boating enthusiasts will appreciate the private dock and boat lift at the rear of the property, with additional capacity to add a second dock and lift along the side canal—an extraordinary advantage rarely found. Ideally located, the home offers effortless access to world-renowned Siesta Key Beach and the vibrant Siesta Key Village, placing dining, shopping, and entertainment just a leisurely stroll away. Recently renovated, the residence showcases a large resort-style pool with spa, low-maintenance tropical landscaping, and updated finishes including new appliances, cabinetry, and more—creating a move-in-ready retreat. The peaceful wrap around canal provides a private sanctuary where nature and waterfront living converge. Set on an expansive ~14,000 square foot lot, this property is also offered at a compelling value at just above land pricing, presenting a remarkable opportunity for a custom luxury estate. Building plans are available and this lot is build to suit.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jessica Hoffman (941-400-5778)
1660 SUMMERHOUSE LN #402, SARASOTA, FL 34242
$1,895,00053 Days on yellowkey MLS ID: A4684751
4 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2110 Built: 2007 Tax: $12,115 (2025)Community: Summer Cove On SiestaCondo
Taxes:$12,115
Remarks: Rarely available bayfront luxury awaits in Summer Cove on Siesta Key— offering expansive water views in a boutique, gated community of just 45 residences on 3.5 lush acres with beach access to world-famous Siesta Key Beach. Built in 2007, this beautifully renovated 4th-floor condo offers 3 bedrooms with 2.5 baths, in approximately 2,100 sq ft that truly lives like a single-family home. A private elevator lobby affords direct entry into your foyer. The open-concept interior is stunningly updated and impeccably finished, with a designer kitchen featuring quartzite countertops and backsplash, white cabinetry, stainless steel appliances, and sweeping water views. The kitchen flows seamlessly into the dining area and spacious living room, where floor-to-ceiling sliders span the entire length of the space. Open the sliders to an oversized bayfront terrace with glass railings showcasing beautiful water views —perfect for sunrise coffee, watching boats cruise the Intracoastal, and dining al fresco in the evenings. The primary suite is equally impressive, showcasing floor-to-ceiling sliders that frame beautiful bay views, plus two custom walk-in closets and a spa-inspired bath with soaking tub, dual-sink vanity, and an expansive walk-in shower with multiple shower heads, including a rain shower. A split floor-plan, two additional bedrooms are tucked down the hall—one with a large custom walk-in closet, partial Gulf views, and an en-suite bath that also opens to the hallway. Additional highlights include a laundry room with sink, bonus storage room with closet, convenient service-elevator access, and stair access to the exit. A second terrace is located off the back of the residence and offers partial Gulf views, ideal for sunset lounging. A true standout feature: enjoy sunrises over the bay from your main terrace and sunsets over the Gulf from the rear terrace - the best of both worlds. Hurricane-impact windows and sliders throughout. Two garage parking spaces are included in an adjacent garage, located on the 2nd level for added storm convenience, with a private storage locker behind the parking spaces. Summer Cove amenities include private beach access, a bayfront resort-style pool and hydraulic kayak/SUP launch, boat docks, a striking clubhouse designed by Carl Abbott of the Sarasota School of Architecture, and a recently renovated fitness center that offers the convenience of a true on-site gym just steps from home. Additional clubhouse features include gathering spaces, a full kitchen for easy catering, and a private owner locker—ideal for storing gym gear and more. A pet-friendly community, two large pets are permitted. An active social calendar with frequent clubhouse gatherings makes for a vibrant community. Beyond the gates, enjoy the best of Siesta Key and Sarasota—just minutes to Siesta Key Village for abundant restaurants, boutiques, and island nightlife, and a short drive to downtown Sarasota’s renowned arts and culture - waterfront dining, shopping, theaters, museums, opera, ballet, and symphony. A highly sought-after Siesta Key community where residences are seldom available—don’t miss this exceptional opportunity.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Robert Ruiz (941-544-3299)
6480 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,100,000195 Days on yellowkey MLS ID: C7516381
1 Days Off yellowkey (back on 4/19/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1265 Built: 1979 Tax: $9,359 (2025)Community: Siesta BreakersCondo
Taxes:$9,359
Remarks: Under contract-accepting backup offers. Fabulous Siesta Beach Condo at the Siesta Breakers #403 — Where Paradise Meets Profit Some properties are nice. This one is life-changing. Welcome to Unit #403 at Siesta Breakers — a rare, true beachfront end-unit perched directly on Crescent Beach, one of the most celebrated stretches of coastline on the planet. This isn't just a condo. It's a front-row seat to the Gulf of Mexico, every single day. Siesta Key's world-famous quartz-crystal sand stays cool even in the Florida heat — and 340 linear feet of it belongs exclusively to you and your guests. Across 5.6 lush acres, this gated community delivers a resort lifestyle that most only dream about. Inside, everything is already perfect. Bright. Open. Elevated. The open-concept living space flows effortlessly from designer interiors to a private balcony where sweeping Gulf views and legendary Siesta Key sunsets steal the show — every evening, without fail. The primary suite is a true sanctuary: a generous walk-in closet, an updated bath, and serene water views to wake up to. The guest bedroom is smartly designed for comfort, making it ideal for family or high-paying renters alike. It's offered completely turnkey — furniture, décor, and everything in between. Walk in and start living. Or start earning. Speaking of earning, the numbers speak for themselves. Unit #403 consistently generates $85,000+ annually in rental income, is already booked weekly through July 2026, and plugs directly into Siesta Breakers' highly sought-after weekly rental program. This isn't speculative income potential — the bookings are already in place. The community matches the lifestyle. Heated resort-style pool with tropical landscaping, Lighted tennis & pickleball courts, Private clubhouse, Security Gated Entrance, Secure under-building parking, Steps to island dining, boutique shopping & the free Siesta Key Breeze Trolley. Why #403 is the one: ? Prime beachfront end-unit — panoramic Gulf, pool & sunset views ? 340 ft. of private beach on world-renowned Crescent Beach ? Turnkey furnished & rental-ready from day one ? $85,000+ proven annual rental income ? Bookings already in place through July 2026 ? Low-maintenance luxury in a treasured, gated community Whether you're seeking your forever escape, a luxury vacation retreat, or a high-performing investment — this is the rare opportunity where all three align perfectly. Siesta Breakers #403 isn't just a purchase. It's a decision you'll never regret. Showings are only available on Saturdays between 2pm-4pm. Property is rented weekly thru July 2026.
Listing is courtesy of: CHARLOTTE COUNTY PROPERTIES (941-655-8804)
Listing Agent: Leo Albanes (941-626-9000)
1050 W PEPPERTREE LN #116B, SARASOTA, FL 34242
$669,00056 Days on yellowkey MLS ID: A4684958
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1974 Tax: $5,344 (2025)Community: Peppertree Bay IvSpa: NoCondo
Taxes:$5,344
Remarks: Turnkey coastal living on Siesta Key. Beautifully renovated first-floor Gulf-side garden condominium in the highly sought-after Peppertree Bay Gulf-to-Bay community. This exceptional two-bedroom, two-bath residence has been thoughtfully updated throughout and is offered fully turnkey furnished, creating an effortless opportunity to arrive and immediately enjoy the island lifestyle. The bright end-unit layout features a rare windowed kitchen that fills the living space with natural light, a feature seldom found in comparable garden units. The residence has been extensively improved with brand-new hurricane-impact windows, new flooring throughout, and numerous major system upgrades, including a recently replaced HVAC system, hot water heater, and dishwasher, providing peace of mind and reducing future maintenance expenses for the next owner. In addition, there is expanded square footage, enhancing the overall functionality of the home. The enclosed lanai area overlooks a tranquil lagoon and fountain, offering a peaceful setting for morning coffee or evening relaxation. Additional conveniences include a private in-unit washer and dryer, a dedicated exterior storage room, and assigned parking just steps from the entrance. Peppertree Bay is one of Siesta Key’s most desirable waterfront communities, uniquely positioned Gulf-to-Bay and offering a full suite of resort-style amenities that support a true full-service coastal lifestyle. Residents enjoy private beach access with chairs, two heated swimming pools, tennis courts, pickleball courts, a fitness center, fishing pier, newly updated clubhouse, gas grills, and on-site management with rental services. Ideally located just minutes from Siesta Key Village’s restaurants, shopping, and the world-renowned quartz sand beaches, this beautifully updated residence offers a rare combination of turnkey convenience, meaningful capital improvements, expanded living space, and premier coastal location. While the current owners have chosen not to rent the property, Peppertree Bay’s on-site rental management and strong seasonal demand provide an excellent opportunity for owners who wish to generate rental income.
Listing Agent: Renee Nadiv (941-299-4242)
4046 HIGEL AVE, SARASOTA, FL 34242
$15,500,00079 Days on yellowkey MLS ID: A4682070
0 Days Off yellowkey (back on 2/11/2026)
Bed: 6 Bath: 7.0 Gar: 3 Liv Area Sq Ft: 6468 Built: 1983 Tax: $32,602 (2025)Community: SiestaSpa: YesSingle Family
Taxes:$32,602
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. Experience private beachfront coastal luxury at this one-of-one Siesta Key home, thoughtfully curated for comfort, style, and entertainment - by Pham Development. Perfectly positioned off the Gulf, with gorgeous ocean views throughout the rooms - you can watch a world-class sunset view from your master bedroom. Spanning over 6,468 square feet under air and 9,080 total square feet, this exquisite residence captures the essence of resort-style waterfront living on more than half an acre of pristine Gulf-front land. Be at ease with a surrounding elevated riprap shoreline and the imported rocks, offering both protection and privacy. Pull into the property through the gated entry, with a paved driveway for ample parking. The ground level offers a 3-car garage, spacious private fitness studio with AC, large flex space/storage room, and huge game room that leads out to the truly special backyard - with premium turf, silica sand and a putting area. Host a sunset dinner with the full outdoor kitchen, including a freezer, wet bar, beverage center, ice machine, and 6-burner grill. Have a drink while sitting in the pool facing the ocean, relax in the champagne spa hot tub, or tan on the sun shelf. Put your toes in the sand area of the backyard, or take the paver steps down to the private beach and swim in the ocean - the ultimate paradise. Wake up to the panoramic views of the Gulf of America and Sarasota Bay, that create a daily masterpiece of color and light, and have a coffee on the master bedroom's private balcony. With 6 bedrooms, 5 full bathrooms, and 2 half baths, you can host more family and guests - along with the second living room/media room. All of the bedrooms have custom built-in closets, and the spacious ocean-view master bathroom leads to two spacious walk-in closets. The home features high-ceilings, beautiful hardwood flooring throughout, and cypress beams. The living and dining room area have a fireplace, and the open-floor plan leads out to another large balcony overlooking the ocean. Enjoy the gourmet custom kitchen with Thermador gas appliances, a walk-in pantry, and an extra large quartz island with seating. An elevator connects the 3-level home through the grand living spaces that flow seamlessly toward the water, blending indoor sophistication with the beauty of the coast. The lush tropical landscaping evokes the serenity of a private resort. Located just minutes from Siesta Beach, the Village, and the North Siesta Bridge, this rare coastal jewel offers the ultimate combination of elegance, exclusivity, and Gulf-front tranquility—a move-in ready residence truly without equal on Siesta Key.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
5880 MIDNIGHT PASS RD #206, SARASOTA, FL 34242
$1,335,000195 Days on yellowkey MLS ID: A4668223
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1642 Built: 1982 Tax: $10,871 (2025)Community: CasarinaCondo
Taxes:$10,871
Remarks: Find your beach get-away in this remodeled three-bedroom Casarina condo located on Siesta Key’s famous Crescent Beach. This stunning TURNKEY FURNISHED and updated unit includes an open concept kitchen with high-end custom soft-close cabinetry, designer hardware and granite countertops. The great room was extended to incorporate the balcony into the living space creating an open and airy feeling to this home. A wall mounted television with Sonos audio provides family entertainment. The spacious primary bedroom with a Closet Tech designed walk-in closet opens to a large bathroom with custom cabinets, dual sinks and large walk-in shower. A third bedroom was created during the recent remodel and includes a built-in under window desk. The full-sized laundry room allows for plenty of storage. Luxury vinyl flooring was installed in 2020 in all public rooms. Impact windows were added in 2016. Electric blinds can close off the sliding glass doors to the outside view while all other windows have custom designed plantation shutters. Crown molding and solid wood doors are found throughout the unit. Casarina is an 89-unit condominium complex that sits on 200 feet of private beach and encompasses 7 acres of tropical landscaping. The complex has a clubhouse with kitchen. Spend your days enjoying the beachside pool and spa, play a game of pickleball on one of the two lighted tennis courts, or relax on the island’s famous crystal sand beach. Hop on the free trolley to enjoy the dining, shopping and entertainment at Siesta Key Village. CASARINA ALLOWS OWNERS ONE SMALL PET.
Listing Agent: Suki Scollo (941-587-2289)
5880 MIDNIGHT PASS RD #306, SARASOTA, FL 34242
$1,285,000221 Days on yellowkey MLS ID: A4665591
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1498 Built: 1982 Tax: $8,594 (2025)Community: CasarinaCondo
Taxes:$8,594
Remarks: Welcome to Your Siesta Key Sanctuary. Step into paradise with this turnkey furnished condo in the highly sought-after Casarina complex, offering 200 feet of private beach access on the world-renowned Crescent Beach. Nestled on a lush 7-acre property, Casarina features beautifully landscaped gardens, tennis and pickleball courts, a beachside pool and spa, an elevated beach deck, and a welcoming clubhouse—all just steps from the famous crystal sands of Siesta Key Beach. Located on the third floor, this residence boasts a newly updated kitchen, luxury vinyl flooring, an updated guest bath, and a new AC unit. Enjoy serene garden views from your 17-foot screened balcony, with a peek-a-boo view of the Gulf and pool areas. Need extra space? The flexible 8’ x 8’ breakfast nook can easily be transformed into a home office or additional sleeping area. Casarina is a well-maintained 89-unit complex with fully funded reserves and recent complex renovations. Owners can bring one small pet, and enjoy the convenience of a covered carport and access to the free Siesta Key Trolley for dining, shopping, and entertainment. Whether you're paddle boarding, kayaking, biking, or simply relaxing on the beach, this condo offers the perfect blend of island lifestyle and resort-style amenities.
1169 W PEPPERTREE DR #118A, SARASOTA, FL 34242
$649,00058 Days on yellowkey MLS ID: A4683913
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1083 Built: 1974 Tax: $4,521 (2025)Community: Peppertree Bay IiiCondo
Taxes:$4,521
Remarks: Discover this impeccable, light-filled second-floor End unit in Peppertree Bay, offering serene views of the tranquil pond. Meticulously remodeled and lovingly maintained over 20 years, this residence exudes pride of ownership. Featuring two bedrooms and two bathrooms, the unit is complete with impact windows throughout, ensuring safety and comfort. Every square inch of this home has been tastefully enhanced, and the furnishings are included for your convenience. Enjoy the added convenience of an in-unit washer and dryer. Residents of Peppertree Bay benefit from a wealth of resort-style amenities, including a private beach with lounge chairs, two heated swimming pools, a fitness center, saunas, tennis and pickleball courts, barbecue grills, a fishing pier, and dedicated on-site management. Ideally located just a short stroll from Siesta Village’s shops and dining, and a quick drive to Sarasota’s cultural attractions, this property embodies coastal living at its best. Whether you’re seeking a full-time residence, a winter retreat, or an investment opportunity with rental income potential, this exceptional beachfront property meets all your needs. Don’t miss your chance to embrace the Siesta Key lifestyle—where every day feels like a vacation.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Brian Ward (941-650-7721)
1166 W PEPPERTREE DR #112D, SARASOTA, FL 34242
$725,000105 Days on yellowkey MLS ID: A4678257
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1120 Built: 1974 Tax: $5,936 (2025)Community: Peppertree Bay IiiCondo
Taxes:$5,936
Remarks: Located on Siesta Key, this updated first-floor 2-bedroom, 2-bath condo at 1166 W Peppertree Drive offers an excellent combination of coastal living and rental potential. This home is offered TURN KEY! Just steps from the world-famous Siesta Key Beach, residents enjoy easy access to the island’s renowned white-sand shoreline, along with nearby shopping, dining, and local restaurants. The well-maintained open floor plan features an updated kitchen with granite countertops, custom cabinetry, and stainless-steel appliances. An enclosed lanai provides additional living space with a built-in quartz workspace and owner storage. Both bathrooms offer granite countertops and walk-in showers. Additional features include wood plank tile flooring throughout, updated windows, in-unit washer and dryer, and a remodeled kitchen. Peppertree is a Beach-to-Bay community with resort-style amenities, on-site management, optional rental program, and security, making this property ideal as a primary residence, seasonal retreat, or investment opportunity. Conveniently located near marinas, golf, Siesta village, and downtown Sarasota.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Mike Aveni (941-961-8730)
5169 OXFORD DR, SARASOTA, FL 34242
$1,498,80012 Days on yellowkey MLS ID: V4948468
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1658 Built: 1994 Tax: $15,228 (2024)Community: Siesta BeachSpa: NoSingle Family
Taxes:$15,228
Remarks: WATERFRONT PARADISE!! Welcome to 5169 Oxford Drive, where this elevated, turnkey-furnished home is perfectly positioned on a stunning canal, offering the ideal opportunity for personal enjoyment or rental income. This beautifully maintained property features 3 bedrooms and 3 bathrooms, along with quick access to open water, making it a dream for boating enthusiasts. Start your mornings with a relaxing cup of coffee or tea in your backyard oasis by the private swimming pool. As the day unfolds, gather with family and friends in the warm, inviting living room while enjoying tranquil canal views. The open-concept layout is designed for effortless living, seamlessly connecting to a chef-inspired kitchen just steps away. Upstairs, you’ll find a spacious bedroom and full bathroom, perfect for guests or added privacy. Downstairs features two en-suite bedrooms, providing comfort and convenience for everyone. Step outside to your own private retreat—ideal for entertaining or unwinding. Spend evenings by the pool, fire up the barbecue, or fish right from your private dock and pier. For adventure, grab your paddleboard and head straight out to the Gulf from your backyard. This home showcases exceptional features and thoughtful upgrades throughout, including: • Durable steel roof • Updated flooring • Indoor laundry • Outdoor grilling area • Private swimming pool • Boat slip • Private fishing pier Located just moments from Siesta Beach, you can easily hop on your golf cart or enjoy a scenic walk to one of Florida’s most beautiful shorelines. This is more than just a home—it’s a lifestyle. Seller is offering a one-year home warranty with a full-price contract. Schedule your private showing today and experience this exceptional property and neighborhood firsthand.
Listing is courtesy of: THE C SMITH REAL ESTATE GROUP LLC (407-705-7797)
Listing Agent: John Chalkias (614-284-2560)
5600 BEACH WAY DR #210, SARASOTA, FL 34242
$595,00058 Days on yellowkey MLS ID: A4684669
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1182 Built: 1970Monthly Fee: $1,467 Tax: $4,857 (2025)Community: Beachway AptsSpa: NoCondo
Taxes:$4,857
Remarks: This newly listed condominium presents a distinguished opportunity to own a fully furnished residence directly across the street from the number one ranked beach in the world. Situated across the street from Siesta Key public beach, this property offers an exceptional blend of coastal elegance and investment potential. The two-bedroom, two-bathroom split floor plan provides both privacy and functionality, complemented by easy-to-maintain tile flooring throughout. The screened lanai serves as the true centerpiece, offering breathtaking westerly sunset views over the beach and the heated community pool below, maintained at a comfortable eighty-five degrees for year-round enjoyment. For those seeking rental income, this property is ideally positioned within an established monthly rental program. Its remarkable proximity to the beach, dining, and shopping in both the North and South Siesta Villages makes it a consistently sought-after destination for vacationers throughout the year. The surrounding environment is nothing short of extraordinary. A short stroll leads to the pavilion and the warm, crystal-clear waters of the Gulf of Mexico. Nearby Phillippi Estate Park offers additional green space, while Morton's Siesta Market provides convenient grocery access just minutes away. Community amenities further elevate the ownership experience, including a full kitchen in the community room for entertaining, saunas in the common areas, gas grills in the pool area, and one covered assigned parking space. This meticulously maintained complex reflects genuine pride of ownership at every turn. Whether envisioned as a personal beach retreat or a productive investment property, this residence warrants your immediate attention. Schedule a private showing today.
Listing is courtesy of: SARABAY REAL ESTATE INC (941-355-7696)
Listing Agent: Dion Souza (941-302-3881)
35 SANDY COVE RD #2A, SARASOTA, FL 34242
$975,000212 Days on yellowkey MLS ID: A4653716
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1254 Built: 1970 Tax: $7,373 (2025)Community: Sandy CoveCondo
Taxes:$7,373
Remarks: Sandy Cove – Mid-Century Modern Gulf Front Paradise: Period-preserved mid-century architecture meets breathtaking Gulf front water views in this exceptional Siesta Key residence. Located in Sandy Cove, a hidden gem and distinguished 1970s development of villas and mid-rises, this fifth-floor residence offers a panoramic vista over Big Pass to Lido, Bird Key, and downtown Sarasota—a guaranteed "wow" moment. Sandy Cove Condos was designed in 1969 by Frank Folsom Smith with James Holliday and James Durden, earning a 1970 AIA Florida Award for architectural excellence. This light-filled, architecturally preserved residence is over 1,200 square feet with two bedrooms, two bathrooms, and a thoughtful split floor plan. Upon arrival, you're greeted by a charming garden courtyard that offers a glimpse into the home. Step inside and be captivated by the spectacular living room featuring soaring vaulted ceilings that provide ample natural light and an airy, open ambiance. Enjoy breathtaking Gulf water views from your living room and kitchen sliders, which open seamlessly to your private patio. The sliders pull back to welcome Gulf breezes throughout the entire residence, connecting to several delightful porches and patios—including an additional private palm tree patio with IPE decking. A rare and highly coveted feature: this residence includes a private one-car garage. Gulf front residences in Sandy Cove rarely become available, making this a unique chance to own a piece of Siesta Key's architectural history. The home has potential to be sold furnished and is offered in as-is condition, presenting an opportunity for buyers to customize their personal vision. Ideally situated close to Siesta Key Village—just a short distance away, this truly unique location offers a natural private beach exclusive to the community, along with a fishing pier. Come see this truly "if you know, you know" treasure on Siesta Key.
Listing Agent: Mickey Kiernan (941-402-9115)
1055 W PEPPERTREE DR #102AA, SARASOTA, FL 34242
$850,000107 Days on yellowkey MLS ID: A4677695
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1163 Built: 1974 Tax: $4,365 (2025)Community: Peppertree Bay IvSpa: YesCondo
Taxes:$4,365
Remarks: 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.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Tanya Stutzman (941-504-8785)
4034 ROBERTS POINT RD, SARASOTA, FL 34242
$10,000,00020 Days on yellowkey MLS ID: A4689062
Bed: 5 Bath: 4.5 Gar: 6 Liv Area Sq Ft: 5458 Built: 1990 Tax: $25,533 (2025)Community: Elliot M Prop Siesta KeySpa: YesSingle Family
Taxes:$25,533
Remarks: A rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompassing 5,458 square feet with five bedrooms, four full bathrooms, and one half bath. Showcasing water frontage on both the front and rear with direct, no-bridge access to Sarasota Bay, the home is set on a private 0.64-acre homesite. The property features a brand-new seawall and two exclusive dock settings, including a 16,000 lb boat lift and jet ski lift, along with a private waterfront seating area designed for effortless enjoyment of the serene surroundings. Underground utilities preserve uninterrupted water views, while soaring ceilings and a signature eagle’s nest vantage point elevate the home’s architectural presence and capture breathtaking vistas. Inside, the residence has been masterfully transformed with a refined open-concept design, anchored by a fully redesigned chef’s kitchen featuring Sub-Zero refrigeration, a gas range, new appliances and countertops, and exceptional craftsmanship throughout. Custom millwork, designer lighting, shiplap detailing, and elegant new railings define the home’s modern coastal aesthetic. The thoughtfully designed floor plan offers three distinct kitchen spaces—including a main kitchen, outdoor kitchen, and private guest suite kitchen—along with a private-entry guest residence and a versatile ground-floor loft with dual Murphy beds, providing exceptional flexibility for both everyday living and elevated entertaining. A private elevator services the home, while a new glass front entry door—currently being installed—further enhances its modern coastal presentation. Curated for both comfort and performance, the home is equipped with three new AC systems, a new well, enhanced irrigation and landscaping, a whole-home Generac generator, reverse osmosis and Kinetico water systems, and full smart home integration through Control4 automation, Sonos audio, and a high-end AV infrastructure. Outdoors, a resort-style pool and spa with both gas and electric heating and full app-based control ensure year-round enjoyment. Additional features include a six-car garage with epoxy floors, a bespoke outdoor bar and kitchen, screened enclosure, kayak storage, and a private sand area—culminating in a truly turnkey, design-forward waterfront estate in one of Sarasota’s most coveted locations.
6140 MIDNIGHT PASS RD #101, SARASOTA, FL 34242
$875,00075 Days on yellowkey MLS ID: A4682618
REDUCED by $24,998 (2.8%) on 04/15/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 1041 Built: 1967 Tax: $8,899 (2025)Community: Horizons WestCondo
Taxes:$8,899
Remarks: Experience the ultimate Siesta Key beach get-away in your TURNKEY FURNISHED, west-facing condo at Horizons West and just steps from your private beach with plenty of beach chairs and five sun cabanas. Enjoy the crystal sands of Crescent Beach where the sand is always cool and you’ll never miss a sunset. This spacious 1-bedroom retreat boasts over 1,000 sq. ft. and has tiered ceilings up to 9 ½ feet. The west facing wall of oversized 6-foot-high impact windows frame breathtaking panoramic Gulf, beach, resort pool and sunsets sunset views, including dolphin sightings. Perched above the lobby and mezzanine, use the elevator to enter this bright and cheerful end-unit with west and south facing windows in the living room. Enjoy an open, airy floor plan with a designer kitchen featuring stone countertops, stainless appliances, and a breakfast bar. The generously sized bedroom has south and east facing windows and an en-suite bathroom with a beautifully tiled walk-in shower. Resort-style amenities abound: 300 ft. of private beach, two pools, spa, cabanas, grills, and a bayside park with day dock. This unit comes with 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 the #1 Beach in the USA and #4 in the world—your piece of paradise awaits!
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