Location: Sarasota , 34242
Do Not Show Listings
8635 MIDNIGHT PASS RD #201C, SARASOTA, FL 34242
$624,999Listed 04/01/2026 2:59PM MLS ID: A4688472
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1160 Built: 1970 Tax: $5,913 (2025)Community: Bay Tree ClubCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,913
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: This beautifully furnished END-UNIT condo is a true gem, offering an abundance of natural light and a spacious, open layout. Featuring 2 bedrooms and 2 bathrooms, this home effortlessly blends comfort and style, making it the perfect space for both relaxation and entertaining. Step outside onto your private lanai and take in breathtaking views of serene Intracoastal waters—an ideal spot to unwind and embrace the peaceful surroundings. The primary bedroom features a walk-in closet and an en-suite bathroom for added convenience and comfort. The second bedroom is spacious, perfect for guests or family members alike. The kitchen boasts beautiful granite countertops, stainless steel appliances, and shaker cabinets with soft-close features, creating a sleek and functional cooking space. Located within a Gulf to Bay Community, this second-floor condo is just steps away from the pristine beach, which includes its own assigned storage cabana to stow your beach essentials, bikes, umbrellas, and chairs. Bay Tree community offers two heated pools, BBQ areas, kayak storage and fishing pier. For boating enthusiasts, the available boat slips provide easy access to the newly reopened Midnight Pass for all your water adventures. Fully furnished and with a STRONG rental history, this condo serves as an excellent income property—making it a fantastic choice for both vacation home seekers and investors alike. Equipped with HURRICANE IMPACT WINDOWS for added peace of mind and energy efficiency, this condo offers durability while maintaining a quiet, comfortable living environment. Additionally, the completed milestone inspection ensures transparency and confidence for the next homeowner. The monthly fees also cover a variety of essential services, including common area insurance, common area flood insurance, and an annual AC inspection and onsite Property Manager. Conveniently located near the free trolley stop, you’ll have easy access to explore Siesta Village’s restaurants, shops, and the world famous Siesta Key Beach with its white quartz sand. Don’t miss your chance to own a piece of paradise in one of Siesta Key’s most desirable locations. Whether you're seeking a vacation retreat, an investment property, or a coastal haven, this condo has it all! Schedule your showing today!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Justin Piccillo (908-670-3209)
9397 MIDNIGHT PASS RD #901, SARASOTA, FL 34242
$896,50035 Days on yellowkey MLS ID: A4683506
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1630 Built: 1975Monthly Fee: $1,433 Tax: $7,721 (2025)Community: Pointe On Midnight PassCondo
Taxes:$7,721
Middle School: Booker Middle
Remarks: Absolutely stunning, furnished, and truly one-of-a-kind THREE-BEDROOM residence at The Pointe at Midnight Pass — the only 3-bedroom currently available in this highly sought-after community. Positioned on the 9th floor at the southern tip of Siesta Key, this impeccably renovated corner unit sits at a rare coastal convergence where the Gulf, Little Sarasota Bay, and Blind Pass Lagoon meet. Enjoy panoramic sunrise views across the Intracoastal waters, glowing Gulf sunsets, and protected preserve vistas — all from one extraordinary setting. High-end finishes define the interior, including solid wood cabinetry, granite countertops, stainless appliances, and thoughtfully curated details throughout. The spacious primary suite features a beautifully updated en-suite bath with a jetted shower and a custom walk-in closet designed for optimal storage. Two additional bedrooms function seamlessly as guest suites, office, or den. The Gulf side bedroom is equipped with a custom Murphy bed and built-ins, offering flexibility without sacrificing style. The second bath features a Jacuzzi tub for relaxed coastal living. The expansive, air-conditioned lanai invites year-round enjoyment, offering a serene vantage point overlooking the Jim Neville Preserve and surrounding waterways. A pass-through utility room with washer, dryer, laundry sink, and folding counter adds everyday practicality. New hurricane-impact windows and sliding glass doors, along with an energy-efficient HVAC system, provide comfort and peace of mind. A rare double parking space under the building further distinguishes this offering. The Pointe is a gated, pet-friendly, five-acre waterfront community featuring boat and kayak docks, resort-style pool, tennis and pickleball courts, fitness center, saunas, clubhouse amenities, and a private island gazebo. More than a condominium, this is a private waterfront retreat positioned in one of Siesta Key’s most iconic locations.
Listing is courtesy of: CAPITAL REAL ESTATE ENTERPRISE (941-921-1000)
Listing Agent: Andrea Eck (941-704-7222)
1257 S PORTOFINO DR #203, SARASOTA, FL 34242
$370,0006 Days on yellowkey MLS ID: A4687158
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 929 Built: 1968 Tax: $2,351 (2025)Community: Siesta HarborCondo
Taxes:$2,351
Middle School: Sarasota Middle
Remarks: Experience the best of Siesta Key living in this 55+ waterfront community at Siesta Harbor, featuring DEEDED BEACH ACCESS, beautiful WATER VIEWS and BOATING ACCESS with available slips. This well-maintained 2-bedroom, 2-bath condo overlooks a deep-water canal along the Intracoastal Waterway, with tranquil views from the living room, primary suite, and screened lanai. Offering one of the lowest-priced condos in the community, this residence presents a fantastic INVESTMENT OPPORTUNITY—enjoy it as-is or update to your personal style over time. Siesta Harbor is known for its active lifestyle and amenities, including a heated pool, spa, clubhouse, shuffleboard, barbecue area, and fishing dock. Boating enthusiasts will appreciate the option for boat slips accommodating up to approximately 30 feet (subject to availability and nominal fees). Ideally located with easy on/off island access, plus trolley and SCAT transportation nearby, and close to dining, shopping, and all that Siesta Key has to offer—this is coastal living made simple. Just steps away, enjoy Siesta Key Beach—consistently ranked among the top beaches in the world for its powdery white quartz sand and crystal-clear Gulf waters. And at the end of your day, take the convenient and free trolley to explore the nearby Siesta Key Village, filled with charming boutiques, casual and fine dining, and lively island atmosphere that perfectly captures the spirit of coastal living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Melissa Gissinger (941-404-2722)
6703 MIDNIGHT PASS RD #217, SARASOTA, FL 34242
$349,000108 Days on yellowkey MLS ID: A4675087
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 702 Built: 1974 Tax: $4,017 (2024)Community: Sea WindsCondo
Taxes:$4,017
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Whether you're looking for a vacation home, rental investment property, or year-round residence, this Sea Winds condo offers excellent value in one of Florida's most beloved beach destinations. Embrace island living in this charming 1 bed room, 1 bath second floor highly rentable condo located in the desirable Sea Winds community on Siesta Key. This condo offers the ability to be rented every two weeks with HOA approval needed for longer rentals, making this an investors dream. Just a short stroll from access 12 leading to the world-famous sands of Siesta Beach, shopping and wonderful restaurants await. This inviting residence fully furnished and including a brand new Tempur Pedic King size bed, combines a relaxed coastal vibe with everyday comfort and convenience. There is on-site laundry and a sparkling swimming pool. The community is well-maintained with tropical landscaping. Current assessments included new roof, pool resurfacing and parking lot repaving. Major upgrades to the building complete. No hurricane damage was sustained in this second floor unit. The living area offers a bright and airy layout with a large 50 inch TV. The pull out couch accommodates more sleeping space for your guests. The kitchen offers ample counter space and a dining area perfect for entertaining or casual meals. The spacious bedroom provides a peaceful retreat with generous closet space, while the full bath is tastefully finished in a breezy coastal style. Don't miss this Sea Winds gem. Current owner has intermittent rentals booked through early April and is happy to transfer bookings with closing.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jessica Fabre (973-259-8205)
5855 MIDNIGHT PASS RD #227, SARASOTA, FL 34242
$499,00076 Days on yellowkey MLS ID: TB8463933
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1056 Built: 1976 Tax: $4,947 (2025)Community: Harbor Towers Y & RCondo
Taxes:$4,947
Remarks: 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!
Listing is courtesy of: REDFIN CORPORATION (617-458-2883)
Listing Agent: Steven Weiss (845-242-5473)
6140 MIDNIGHT PASS RD #A10, SARASOTA, FL 34242
$849,900139 Days on yellowkey MLS ID: A4671897
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1068 Built: 1967 Tax: $7,853 (2024)Community: Horizons WestVilla
Taxes:$7,853
Remarks: Are you looking for new? Welcome to your fully renovated, turnkey Siesta Key villa, where everything is new from top to bottom! On the Gulf side with direct beach access, this stunning two-bedroom, two-bath coastal retreat has been beautifully transformed into a modern beachside haven. Every detail has been redone with quality and style, such as new kitchen, furnishings and décor, ready for you to move right in and start living your best island life. In the sought-after Horizons West community, this villa offers the ideal blend of comfort and convenience. Enjoy two community pools (one right on the sand and one near your door), along with beach access. Whether you’re seeking a personal getaway or a high-performing investment property, this villa checks every box, and it’s part of a rental program with flexible leasing options and an on-site manager. Experience the ultimate Siesta Key lifestyle, close to Siesta Key Village, where you’ll find vibrant restaurants, boutique shops and nightly entertainment. Or head just minutes away to downtown Sarasota for arts, dining and culture. Own your piece of paradise today, new, beautiful and next to the #1 beach in the world.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Jaci Krawtschenko (941-284-3789)
208 HOURGLASS WAY #V11, SARASOTA, FL 34242
$475,000Listed 04/01/2026 12:27PM MLS ID: A4688135
0 Days Off yellowkey (back on 4/1/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1432 Built: 1968Monthly Fee: $1,793 Tax: $3,258 (2025)Community: Whispering SandsVilla
Taxes:$3,258
Remarks: 3 bedroom/2 bath freestanding villa with fenced patio. Remediation from 2024 hurricane damage completed. Property has yet to be rebuilt.
Listing Agent: Harriet Stopher (404-316-8944)
5968 MIDNIGHT PASS RD #158, SARASOTA, FL 34242
$760,00055 Days on yellowkey MLS ID: A4681104
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1134 Built: 1975 Tax: $7,449 (2025)Community: Palm Bay Club IiiCondo
Taxes:$7,449
Remarks: 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)
7233 PINE NEEDLE RD, SARASOTA, FL 34242
$4,300,000Listed 04/01/2026 1:07PM MLS ID: A4688394
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4294 Built: 1950Monthly Fee: $450 Tax: $9,991 (2025)Community: Siesta Properties IncSingle Family
Taxes:$9,991
Remarks: Pre-Construction. To be built. MLS remarks: A rare and compelling opportunity to create a custom coastal estate within the prestigious Sanderling Club on Siesta Key, one of the island’s most private and sought-after enclaves. Set on an expansive .70-acre homesite, this future residence will feature a thoughtfully designed footprint spanning 4,294 square feet under air and over 6,400 total square feet, offering a refined blend of scale, comfort, and architectural presence. Positioned to capture desirable southern exposure, the property enjoys a serene natural backdrop, creating a setting rich in privacy, wildlife, and unobstructed beauty. The home will be delivered with the structural framework and layout in place, while allowing the future owner to curate finishes, materials, and design details to their exact vision, resulting in a truly personalized luxury residence. The Sanderling Club is renowned for its understated elegance and unmatched seclusion, offering 24-hour guard-gated security and a lifestyle centered around privacy and connection to nature. Residents enjoy access to tennis and pickleball courts, a private marina, and a historic beachfront clubhouse with exclusive access to the powdery white sands of Siesta Key Beach. Quiet, secure, and distinctly refined, this is an extraordinary chance to bring your vision to life within one of Sarasota’s most coveted coastal communities—where luxury is defined not only by design, but by space, serenity, and discretion.
Listing Agent: Rudy Dudon (941-234-3991)
7647 SANDERLING RD, SARASOTA, FL 34242
$3,999,00017 Days on yellowkey MLS ID: TB8486392
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4006 Built: 1961Monthly Fee: $450 Tax: $23,004 (2025)Community: Sanderling ClubSingle Family
Taxes:$23,004
Remarks: Introducing The Ness House, a rare architectural offering designed by renowned Sarasota School architect Tim Seibert where timeless design meets the natural beauty of Siesta Key. Privately set within the sought-after Sanderling Club, this residence reflects a philosophy of simplicity, light, and connection to nature. Clean lines, expansive glass, and thoughtful proportions create a living experience that feels both intentional and serene. Natural light fills the interiors, while walls of glass frame lush tropical surroundings, blurring the line between indoors and out. Every space has been designed to capture the essence of coastal living quiet, refined, and effortlessly elegant. A truly rare feature of this property is its private rear entrance with a 10-minute walk directly to Siesta Key Beach, offering a seamless connection to one of the most celebrated beaches in the world while maintaining privacy and tranquility at home. The outdoor areas provide a peaceful retreat, ideal for relaxing or entertaining, surrounded by mature landscaping and the calming presence of nature. Whether enjoying morning light or evening breezes, the setting invites you to slow down and fully experience the moment. For those who appreciate architectural significance, The Ness House represents more than a home, it is a legacy property rooted in one of Sarasota’s most influential design movements. Located within a private, gated community and just moments from dining and coastal attractions, this is a rare opportunity to own a piece of architectural history with both privacy and proximity to the Gulf. Timeless design. Private access. A lifestyle that feels both elevated and effortlessly coastal.
Listing is courtesy of: PREMIER SOTHEBY'S INTL REALTY (727-595-1604)
Listing Agent: Janet Moore (813-892-0998)
5201 AVENIDA DEL MARE, SARASOTA, FL 34242
$1,495,00057 Days on yellowkey MLS ID: A4680975
REDUCED by $65,000 (4.2%) on 04/01/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2802 Built: 2008 Tax: $6,145 (2025)Community: Sarasota BeachSingle Family
Taxes:$6,145
Remarks: WELCOME to one of Siesta Key's hidden gems. From this Key West style home, you can walk or bike ride to the soft, quartz sands of Siesta Beach or the quaint Siesta Village in minutes. This exceptional home offers high end finishes throughout. The native yard features beach sunflowers and other native plants and shrubs. The front door entrance invites you into the main level with an easy flow between the living room and the dining room. The gourmet kitchen features wood cabinets, granite countertops, stainless steel appliances and French Door refrigerator. The guest bath, laundry room and bonus room complete the downstairs. The backyard is a fenced, private oasis with a pool surrounded by stone pavers with room for lounge chairs, grill and an outdoor table setting. Mature royal palm trees and smaller palms create a beautiful habitat for birds and other wildlife. The second floor has two comfortable bedrooms, one with a private balcony. A full bath completes this level. The top level offers a spacious Primary Bedroom and En Suite Bathroom retreat with exceptional amenities, a large bathroom with granite countertops, wrap-around walk-in shower, and separate garden tub, with a screened-in balcony overlooking the pool area. The top level is completed by an additional Bedroom with an en suite Bathroom with walk-in shower, linen closet, and granite countertops. Additional features include solar panels (paid in full), a security system, stone paved driveway and walkway, along with an oversized 2 car garage. This open, sunny home is located in a quiet neighborhood at the end of the street and has so many quality features. It is definitely worth a visit.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Mary Kassen (941-900-9776)
757 BEACH RD #308, SARASOTA, FL 34242
$595,5003 Days on yellowkey MLS ID: TB8492005
REDUCED by $33,500 (5.3%) on 04/01/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 816 Built: 1970 Tax: $5,582 (2025)Community: Crescent RoyaleCondo
Taxes:$5,582
High School: Riverview High
Remarks: Prime location directly across the street from Siesta Key Public beach has a full Gulf view that enjoys gorgeous sunrises and sunsets! Unit was completely gutted and remodeled with high end finishes, paint, and furniture in 2011. Everything is in excellent condition. This third floor unit in the highly desired Crescent Royale Condominium complex has a screened lanai, assigned covered parking space and storage locker for beach gear. Complex has large heated pool, grills with picnic area, bike parking, shuffleboard, a Clubhouse with pool table, exercise room and bathrooms. One mile to the Village restaurants and shops. This unit is sold turnkey furnished and allows weekly rentals. Use excellent on-site management or DIY on VRBO and AirBNB. Start your revenue stream from day one - ask to see our stunning rental history!
Listing is courtesy of: COMMUNITY REALTY ASSOCIATES (561-852-1341)
Listing Agent: Douglas Addeo (561-251-3408)
4660 OCEAN BLVD #Q1, SARASOTA, FL 34242
$525,000224 Days on yellowkey MLS ID: A4659204
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971 Tax: $7,101 (2024)Community: Sea VillageCondo
Taxes:$7,101
Remarks: PRICED TO SELL! New hurricane-impact sliders have been ordered and will be installed prior to closing. Experience million-dollar, direct Gulf views from this ground floor condominium in the sought after community of Sea Village on Siesta Key. Enjoy sunsets every evening from your private lanai, just steps from the shoreline and minutes from one of the world’s top beaches. This 2-bedroom, 2-bath residence has been thoughtfully updated with a fully remodeled kitchen, tile flooring throughout, and plantation shutters. Hurricane-impact windows provide peace of mind and lasting value. Additional features and upgrades include a 2021 water heater, 2022 HVAC, 2023 electrical panel, in-unit washer and dryer, designated parking, storage shed, and bike storage. Sea Village offers residents a true coastal lifestyle with a heated waterfront pool, tropical grounds, and easy access to dining, shopping, and Siesta Key’s vibrant village. Covered parking and generous guest parking make entertaining convenient. Perfect as a primary residence or seasonal retreat, this home blends unmatched views with modern upgrades in one of Sarasota’s most desirable island communities.
Listing Agent: Halie Monde (941-735-4707)
9265 BLIND PASS RD, SARASOTA, FL 34242
$3,000,00066 Days on yellowkey MLS ID: A4676249
1 Days Off yellowkey (back on 2/22/2026)
Bed: 4 Bath: 3.0 Liv Area Sq Ft: 3186 Built: 1998 Tax: $13,081 (2025)Community: Acreage & UnrecSingle Family
Taxes:$13,081
Remarks: Under contract-accepting backup offers. Gulf-to-Bay elegance meets relaxed coastal sophistication in this elevated, sailboat-access waterfront retreat, ideally positioned within one of Siesta Key’s most exclusive gated enclaves. Set in a rare peninsula neighborhood offering true Gulf-to-Bay living, this Caribbean-inspired residence delivers exceptional privacy, sweeping water views, and direct boating access with no bridges to the Intracoastal Waterway. With the newly reopened Midnight Pass just minutes away, access to the Gulf is effortless, making this an extraordinary opportunity for boaters and beach lovers alike. Surrounded by mature tropical landscaping and located on a quiet dead-end street, the home enjoys both Gulf views and a tranquil basin setting with a private dock. Inside, a vaulted-ceiling great room anchors the main living level, filled with natural light and framed by sliding glass doors that open to expansive covered terraces on both the east and west sides—perfect for sunrise mornings and sunset evenings overlooking the water. The open-concept kitchen is designed for entertaining and everyday living, featuring premium appliances including a Sub-Zero refrigerator and generous workspace. The primary suite is located on the main living level, offering terrace access and serene water views, while additional guest accommodations provide flexibility for family and friends. Above, a rooftop observation deck—accessible via spiral staircase—offers breathtaking 360-degree vistas spanning the Gulf, bay, and coastline, creating a truly unforgettable vantage point. Thoughtfully constructed on pilings with storm-conscious design, the home blends timeless island style with peace of mind. The ground level provides covered parking for multiple vehicles, abundant storage, and space for kayaks, paddleboards, and beach gear. An elevator shaft is already in place for future installation, and pool plans are available. With deeded beach access just steps away and a private dock at your back door, this is one of the few properties on Siesta Key where you can enjoy the beach in front and your boat behind. Beach, boating, privacy, and views converge in this exceptional offering—capturing the essence of Gulf-to-Bay living on Siesta Key. From morning experiences along the shoreline to breathtaking sunsets over the Gulf, every day on Siesta Key feels like a vacation. And when you're ready to explore beyond the island, downtown Sarasota is just a short drive away, offering world-class dining, arts and culture, including the Ringling Museum, Van Wezel Performing Arts Hall, and St. Armands Circle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
5661 MIDNIGHT PASS RD #401, SARASOTA, FL 34242
$475,00070 Days on yellowkey MLS ID: A4678954
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1012 Built: 1975 Tax: $4,629 (2025)Community: White Sands VillageCondo
Taxes:$4,629
Remarks: Welcome to coastal living at its best in White Sands Village, a desirable waterfront community ideally located in the middle of Siesta Key and 1 mile from The Village. This charming 2-bedroom, 2-bath end-unit condominium (no flood damage), offering added peace of mind and ease of ownership. The community is surrounded by lush tropical landscaping and features a clubhouse and sparkling community pool, creating a relaxed island atmosphere. White Sands Village offers water access with Gulf-front amenities and boat slips available via waitlist, perfect for boating enthusiasts. This property may be used as a rental or income-producing investment with a minimum 2-week rental period, making it an excellent option for seasonal use or short-term rental opportunities. Ideally located across the street from world-famous Siesta Key Beach, along with nearby restaurants, shopping, and entertainment, plus convenient on-and-off island access. Whether you’re looking for a full-time residence, vacation retreat, or rental investment, this property delivers the best of the Siesta Key lifestyle.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lisa Blakeney (616-795-6545)
4839 GIVENS CT, SARASOTA, FL 34242
$2,750,00031 Days on yellowkey MLS ID: A4683309
Bed: 5 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3524 Built: 1994 Tax: $25,564 (2025)Community: Siesta HammockSingle Family
Taxes:$25,564
Remarks: Private Estate Compound/ Siesta Key Family Estate. Multi-generational Buyers MUST SEE. Picture yourself living and entertaining friends and family at your Key West-style home, wrapped around a sparkling saltwater pool with a separate guest house and studio apartment- all nestled in lush native landscaping on the world-renowned barrier island of Siesta Key. The main house welcomes you with a large covered front porch and double wooden plantation doors. Enter a huge sun-filled and vaulted living room with Caribbean Rosewood floors, with a view through French doors to the terrace, an open pool deck, and a wooded lot. Off the corners of the living room are three large private en suite bedrooms. The airy owner’s suite features a private library- a cozy spot to enjoy the private deck, pool, and view beyond. The kitchen is well-appointed with stainless-steel KitchenAid appliances, cherry cabinetry, and a Blue Macauba quartz island, complemented by designer touches. The kitchen opens onto the terrace and a spacious dining and family room with a fireplace. A large (27x22) Guest Suite/Bonus Room with a Full Bath is located above the 2-car garage. Tucked under the oaks is a stone patio leading into a Studio with a Full Bath. Gardens and raised garden beds are ready for you to grow your favorite foods and flowers. A private well provides irrigation. The grounds have plenty of room to run and play outdoors and can easily accommodate building expansion or additional amenities. Motivated Seller!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Caroline Amory (941-524-0463)
3941 HAMILTON CLUB CIR #9, SARASOTA, FL 34242
$2,390,00020 Days on yellowkey MLS ID: A4685652
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2856 Built: 1989Monthly Fee: $1,400 Tax: $15,416 (2025)Community: Hamilton ClubSingle Family
Taxes:$15,416
Remarks: Located in the highly sought-after Hamilton Club community on Siesta Key, this beautifully updated 3-bedroom, 3.5-bath residence offers the ideal blend of coastal comfort, boating convenience, and island living. A large screened-in porch overlooking the water provides a peaceful setting to enjoy morning coffee and gentle coastal breezes. Designed for both everyday living and entertaining, the home features a new private elevator, impact windows and doors, and your own private 10,000-lb boat lift with quick access to the water, making it easy to enjoy boating and the surrounding waterways. Each well-appointed bedroom offers its own private en-suite bathroom, providing exceptional privacy for family and guests. The residence has been thoughtfully upgraded with kitchen updates completed in 2023, updated lighting throughout (2023), fully renovated bathrooms (2022–2023), and new wood flooring, creating a fresh, modern aesthetic with timeless coastal appeal. Additional improvements include a new water softener and water pressure pump installed in 2025, enhancing everyday comfort and functionality. The home is offered furnished or unfurnished, allowing buyers the flexibility to move right in or personalize the space to their style. Hamilton Club residents will also enjoy new community landscaping scheduled for this summer, with exterior building painting planned for 2027, both covered within HOA dues for added peace of mind. Ideally located just minutes from Siesta Key’s world-famous beaches, dining, and shopping, this residence offers an exceptional combination of water views, private boating access, modern upgrades, and relaxed island living.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
5507 CONTENTO DR, SARASOTA, FL 34242
$1,775,00041 Days on yellowkey MLS ID: A4683288
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1788 Built: 1969 Tax: $15,484 (2025)Community: Siesta IslesSingle Family
Taxes:$15,484
Remarks: A BOATER'S DREAM! Welcome to your Siesta Key waterfront dream home on a third of an acre lot! Private dock with a 7,000lb boat lift on a wide part of the Grand Canal! Move right in and start enjoying the island lifestyle! This home features great water view on the widest part of the canal! Brand new landscaping and freshly painted exterior. Sold furnished with a few exceptions. The heated pool and panoramic pool cage create a serene setting. Mostly Hurricane rated windows, new dishwasher and refrigerator, wine refrigerator, custom wood cabinets, granite counters and breakfast bar. Tile floors and engineered wood, built-out closets, open floor plan, 2 car garage, circular driveway, outdoor shower. 3 bedrooms and 3 full bathrooms plus laundry room. A few blocks from world famous SIESTA BEACH, short drive to downtown Sarasota, St Armand's, Lido and much more. ***THIS HOME HAS NOT HAD ANY STORM DAMAGE AND NO FLOODING.****BASE ELEVATION 10 Ft***SELLER MOTIVATED***
Listing Agent: Livya Hament (941-735-1227)
300 GARDEN LN, SARASOTA, FL 34242
$2,999,000209 Days on yellowkey MLS ID: A4662830
REDUCED by $200,000 (6.3%) on 04/01/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3256 Built: 1975Monthly Fee: $10 Tax: $12,545 (2024)Community: Siesta Rev OfSingle Family
Taxes:$12,545
Remarks: A Rare Opportunity on North Siesta Key – 350 Feet of Waterfront! Discover this unique single-story property on Bay Island, offering both beauty and potential. High and dry, the home remained unaffected by recent storms, with 4–5 feet of elevation to spare. Set on a tranquil, tropical lot, this historic location on Garden Lane—once home to the Siesta Key Fish Market—is truly a boater’s and fisherman’s paradise, just steps from Shell Beach and its breathtaking sunsets. The property features a classic Florida ranch-style 4-bedroom, 2-bathroom home with a pool, large deck, and lush backyard designed for entertaining, plus a detached 2-bedroom, 2-bathroom guest house. Whether you choose to renovate, rebuild, or divide the lot (buyers to verify with the City), the possibilities are endless. All this just minutes from world-famous Siesta Key Beach, The Village shopping, dining, and nightlife, and vibrant downtown Sarasota.
Listing Agent: Holly Parry (941-809-8050)
915 SEASIDE DR #310, SARASOTA, FL 34242
$1,399,0001 Day on yellowkey MLS ID: A4686908
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1900 Built: 2009 Tax: $14,651 (2025)Community: Siesta Key Beach Residences IiCondo
Taxes:$14,651
Remarks: 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)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.