Location: Sarasota , 34242
Do Not Show Listings
316 BEACH RD, SARASOTA, FL 34242
$5,249,0005 Days on yellowkey MLS ID: A4697531
Bed: 8 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 4681 Built: 1996 Tax: $37,822 (2025)Community: Sarasota BeachSpa: YesApartment
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$37,822
Elementary School: None
High School: None
Tax Year: 2025
Middle School: None
Remarks: Completely renovated in 2021, this property offers the appeal and functionality of newer construction while delivering a proven track record as a high-performing short-term rental. Generating approximately $400,000 to $500,000 in annual rental revenue, the home has been thoughtfully designed to accommodate large groups with eight bedroom suites, expansive gathering spaces, and a seamless blend of indoor and outdoor living. Guests are drawn to the experience this property provides—from mornings spent taking in Gulf views from the balconies to afternoons by the private pool and spa, and evenings gathering around the outdoor kitchen or enjoying time with family and friends throughout the home's multiple entertainment areas. Its spacious layout, private elevator, and proximity to both beach access and Siesta Key Village continue to make it a sought-after destination for vacationers. Combining strong rental performance with luxury coastal living, this property presents a rare opportunity to own an established income-producing asset in one of Siesta Key's most desirable locations.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
1400 COVE II PL #631, SARASOTA, FL 34242
$549,900134 Days on yellowkey MLS ID: A4681753
REDUCED by $25,100 (4.4%) on 06/14/2026
Bed: 2 Bath: 1.5 Liv Area Sq Ft: 860 Built: 1979 Tax: $5,509 (2025)Community: Midnight Cove IiCondo
Taxes:$5,509
Remarks: Welcome to the most adorable condo on world famous SIESTA KEY. Start enjoying the island lifestyle in this TURNKEY condo with GREAT WATER VIEWS and pool views! ***WEEKLY RENTALS***Very comfortable open floor plan with balcony to sip your cocktails and relax. The PRIVATE DEEDED BEACH ACCESS to the quartz sand Siesta beach in priceless. Midnight Cove offers tennis, pickleball, barbecue areas, fitness, pool, on site management, boat docks and more. Very importantly, there was no storm damage. Take the free trolley to Siesta Village or walk to the south village restaurants and shops. Downtown Sarasota and St Armand's Circle just a short drive away. An excellent opportunity for your vacation getaway or investment property. *** $110,000 PRICE REDUCTION SHOWS SELLER SERIOUS MOTIVATION***Seller's loss-your gain.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Livya Hament (941-735-1227)
62 SANDY HOOK RD S, SARASOTA, FL 34242
$2,995,000246 Days on yellowkey MLS ID: A4667491
Bed: 5 Bath: 3.0 Liv Area Sq Ft: 2658 Built: 1964Monthly Fee: $161 Tax: $8,811 (2024)Community: Sandy HookSingle Family
Taxes:$8,811
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: In the coveted Sandy Hook Gulf Beach enclave of only 42 homes, this unique Mid-Century Modern home is now offered for purchase for the first time since 1983. The one-of-a-kind mid-century modern retreat rests on 1.6 acres of serene lakefront adjacent to where Big Sarasota Pass meets the Gulf of Mexico. Created by Frank Folsom Smith, a noted member of the Sarasota School of Architecture, this passively designed treasure was crafted from local cypress, oak, terra cotta and Ocala block and sits harmoniously within a lush Florida-native landscape alive with palms, cedars, and blooming wild flora. Nature lovers will delight in the lake along the southern edge of the property, home to a vibrant array of wildlife. The main residence, built in 1964 and lovingly preserved by its current owner since 1983, features timeless modernist design and abundant natural light through true north and south facing 10-foot glass sliders that welcome daylight. Meanwhile the interiors are shielded from direct sun for restful living. The guest house, added in 1987, also designed by the firm, complements the main home, together offering 5 bedrooms, 3 full bathrooms, 2 expansive great rooms, and a rare wood-burning fireplace, perfect for cozy winter evenings. Outdoors, all residents can enjoy their choice of sun-dappled terraces or shaded garden hideaways beneath more than 120 mature palms and cedars. Thoughtful upgrades ensure comfort and ease in this home's remodeled kitchen with all new appliances, new Trane HVAC systems covered by 10-year warranties, a 2025 deep-well irrigation system, and low-voltage outdoor lighting synchronized by the integrated atomic clock for effortless ambiance. Just a 150-meter stroll west through the trees leads you to Sandy Hook’s exclusive residents-only Gulf beach, a secluded paradise of sugarwhite quartz sand where sea turtles hatch annually and dolphins and manatees play offshore and sunsets paint the sky in vivid color. Conveniently located near Siesta Village’s boutiques and restaurants, and within easy reach of top-rated Sarasota County schools, The Out-of-Door Academy, and Sarasota Memorial Hospital, ranked among America’s top 50, this home offers the perfect blend of mid-century authenticity, privacy, and coastal lifestyle. This truly rare architectural offering is where Siesta Key’s natural beauty and Sarasota’s cultural soul meet the timeless artistry of mid-century design.
Listing is courtesy of: CAPITAL REAL ESTATE ENTERPRISE (941-921-1000)
Listing Agent: Fred Beles (941-921-1000)
611 TREMONT ST, SARASOTA, FL 34242
$3,399,000159 Days on yellowkey MLS ID: A4678455
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 4194 Built: 2005 Tax: $21,457 (2025)Community: Siestas BaysideSpa: YesSingle Family
Taxes:$21,457
Remarks: A spectacular offering on one of Siesta Key’s most coveted streets, this stunning canal-front residence on Tremont Street represents a truly special opportunity to own a home that seamlessly blends boating, timeless island charm, and refined coastal living. Tucked beneath mature trees in a quiet, established enclave known for its old Siesta character, the property offers private canal frontage with a lift and a short, easy boat ride to the Intracoastal Waterway, all just minutes from Siesta Village and the world-renowned white sands of Siesta Beach. Homes of this caliber and setting are seldom available and must be experienced in person to be fully appreciated. Offering 4,194 square feet under air, the thoughtfully designed floor plan is both impressive and highly livable, ideal for full time residents and seasonal owners alike. Soaring ceilings, abundant natural light, and quality craftsmanship define the interior. The main floor primary suite is complemented by additional bedrooms on the main level, providing the ease of one level living, while the second floor offers a spacious guest suite and bonus room with peaceful views of the pool and canal. Exceptional indoor-outdoor living is at the heart of the home. Multiple pocketing sliding glass doors open wide to an expansive covered and fully screened lanai, creating a seamless connection between interior and exterior spaces. The outdoor living area is generous in scale and designed for entertaining, featuring a heated pool and spa, summer kitchen, gas fireplace, and multiple areas for dining and relaxation. The large screened layout allows you to comfortably enjoy outdoor living year round, regardless of the weather. Lush tropical landscaping enhances privacy and creates a tranquil island setting, while boating enthusiasts will appreciate the private lift and convenient access to open water. Impact-rated windows and doors, a generator, and a three-car garage provide peace of mind and everyday practicality. 611 Tremont Street combines location, boating, and lifestyle in a way few homes can. If you have been waiting for an exceptional Siesta Key property in one of the island’s most desirable neighborhoods, this is one you should see in person before it sells.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Mike Warm, Llc (941-525-2740)
5400 OCEAN BLVD #6-4, SARASOTA, FL 34242
$1,250,000294 Days on yellowkey MLS ID: A4663880
1 Days Off yellowkey (back on 5/26/2026)
REDUCED by $50,000 (3.8%) on 04/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1187 Built: 1970 Tax: $10,071 (2025)Community: TerraceCondo
Taxes:$10,071
Elementary School: Southside Elementary
Remarks: One or more photo(s) has been virtually staged. Virtually Staged. MAJOR PRICE REDUCTION! The lowest-priced 2-bedroom residence at Beach Terrace in over 8 years—this is the opportunity of the decade! Welcome to one of Siesta Key's most desirable addresses. This exceptional corner residence offers direct Gulf of Mexico frontage, perfectly positioned at the end of the village where luxury meets convenience. Prepare to be captivated by panoramic vistas from your three spacious private balconies. Enjoy unobstructed views of pristine white sand beaches, sparkling aqua Gulf waters, downtown Sarasota's skyline, and even Longboat Key on clear days. Watch the twinkling lights of Siesta Key Village create an unforgettable backdrop as the sun sets—easily among the best views on Siesta Key. Enter through an inviting foyer with elegant tiled flooring leading into a beautifully updated kitchen featuring granite countertops & modern cabinetry. The spacious living area showcases dual sliding glass doors framing stunning Gulf views. The generous dining area provides ample space for entertaining. The primary bedroom features a private Gulf-view balcony with two full-size beds and an elegant ensuite bath with updated tile, modern cabinetry, and granite countertops. The guest bedroom offers a full bed and private sliding door to dazzling Gulf views, plus an updated full bathroom with modern finishes and tile shower. Elevated heated saltwater pool with sunset views, modern fitness center, community room, covered parking, and gated security with onsite management. Private beach access puts you steps from world-renowned Siesta Key Beach. Nestled at the end of the village, enjoy tranquility and convenient access to Siesta Key Village shops and restaurants—no car needed once you arrive. Beach Terrace represents the pinnacle of Gulf-front living. With the lowest pricing for a 2-bedroom in over 8 years, this move-in ready split-floor plan residence is your once-in-a-decade opportunity to own paradise where stunning views, luxury amenities, and coastal elegance unite.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mickey Kiernan (941-402-9115)
420 BEACH RD #203, SARASOTA, FL 34242
$1,249,000553 Days on yellowkey MLS ID: A4631493
0 Days Off yellowkey (back on 6/18/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1980 Tax: $10,693 (2025)Community: Siesta Gulf ViewCondo
Taxes:$10,693
Remarks: Under contract-accepting backup offers. Paradise Found on Siesta Key! Wake up to Gulf breezes and end each day with a sunset over the water from this direct beachfront condo at Siesta Gulf View. This 2-bedroom, 2-bath residence offers a full west-facing panorama of Siesta Beach and the Gulf from its expansive 31-foot screened and glass-enclosed balcony, accessible from the living room, kitchen, and primary suite. From here you can enjoy both the beauty of the shoreline and the natural dune vegetation that makes this second-floor perspective feel close and connected to the beach. This floor level offers an ideal balance of easy access and elevated views: take the stairs for quick trips to the beach, pool, or parking garage, or use the elevator if preferred. No long waits, no hassle, just effortless access to every amenity. The TURNKEY FURNISHED layout includes a light-filled open kitchen with eat-in nook (perfect as a dinette or office), two spacious walk-in closets, separate laundry room, and generous storage throughout. Recent community updates give peace of mind: milestone inspections complete, all cast iron plumbing replaced in 2024, and new clubhouse roof and landscaping nearing completion, with no special assessments. Siesta Gulf View is a sought-after, gated, 59-unit community offering private boardwalk access to the quartz sands of Siesta Key Beach, plus resort-style amenities: a 25’x40’ heated pool, tennis and pickleball courts, fitness room, grilling areas, and clubhouse. Assigned under-building parking, ample guest parking, first-floor storage, and an on-site management office add convenience. Pet lovers will appreciate that up to two small pets are welcome. Best of all, you’re just blocks from vibrant Siesta Key Village: restaurants, shops, and live music are a short stroll away. Whether you’re seeking a vacation retreat, investment property (one-month minimum rentals allowed up to 12 times/year), or full-time Gulf-front living, this condo delivers the ultimate island lifestyle. Don’t miss this opportunity to claim your piece of paradise.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jennifer Russo (212-683-1173)
7233 PINE NEEDLE RD, SARASOTA, FL 34242
$4,300,00083 Days on yellowkey 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 IncSpa: YesSingle Family
Taxes:$9,991
Remarks: Pre-Construction. To be built. 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)
1280 DOLPHIN BAY WAY #402, SARASOTA, FL 34242
$1,599,000123 Days on yellowkey MLS ID: A4682864
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2042 Built: 1997 Tax: $14,580 (2024)Community: Dolphin Bay-Siesta Key Sec ACondo
Taxes:$14,580
Remarks: VIEWS! VIEWS! VIEWS!---You will be WOWED! by the Incredible WATER VIEWS in this Well-Appointed/Upgraded & Furnished SIESTA KEY residence with a Highly Desired and "Rare" TWO (2) CAR CLIMATE CONTROLLED PRIVATE GARAGE with STORAGE!.....Located in Dophin Bay, a Boutique Gated Dog-Friendly Resort Style Waterfront Community where residents have access to Pool, Tennis Courts, Fitness Center and "across the street" proximity to TOP RATED Siesta Key Beach. This 2000+ sq ft with NINE FOOT Ceilings is a Bright & Spacious Open Floorplan that features: Quartz Countertops, Thermador Appliances, Sumptuous Bathrooms, Hurricane Impact Sliders; Generously Sized Ensuite Bedrooms with Over-sized Walk-in Closets; In-Unit Washer/Dryer, Electric Shades, Built-ins Throughout & 2 outdoor living spaces--perfect for morning coffees and cocktails with evening sunsets. Take the Siesta Key Trolley to the Main Village for Dining, Shopping and all the Joys of Island Living!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Veronica Murphy (203-415-5581)
8555 HERON LAGOON CIR, SARASOTA, FL 34242
$2,725,000449 Days on yellowkey MLS ID: A4646820
INCREASED by $1,350,000 (98.2%) on 04/06/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2568 Built: 1951Monthly Fee: $75 Tax: $12,703 (2024)Community: Heron Lagoon LodgesSingle Family
Taxes:$12,703
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Rare Opportunity on Siesta Key – Expansive Corner Lot with Private Beach Access + Custom Coastal Estate by SeaSafe Homes. A truly rare opportunity to build your dream home on one of the largest privately owned parcels on Siesta Key. Situated on an expansive over ¾-acre corner lot with nearly 37,000 square feet, this exceptional homesite offers private beach access via an exclusive pedestrian bridge leading directly to your own slice of Siesta Key’s sugar-sand shoreline. Located within an intimate enclave of only 13 homes along Heron Lagoon, this hidden gem offers unmatched privacy, serenity, and exclusivity on the south end of the island, while remaining just minutes from Siesta Key Village Featured here is the Wave Crest Model by SeaSafe Homes, thoughtfully designed for elevated coastal living. Built for luxury and resilience, this home features a superior 2x12 floor system and 2x6 wall construction, engineered to withstand winds up to 180 MPH, exceeding typical coastal building standards and providing peace of mind. With advanced off-site construction methods, build time can be reduced by up to 75%, minimizing weather-related construction delays and allowing you to enjoy your new home sooner. The thoughtfully designed floor plan offers 4 bedrooms, 3.5 bathrooms, and an open-concept layout ideal for full-time living, seasonal enjoyment, or luxury rental potential. The spacious kitchen flows seamlessly into the living and dining areas and includes a large walk-in pantry and extended island, perfect for entertaining. The primary suite features direct porch access, a spa-inspired bath and walk-in closet. A secondary en-suite bedroom with optional private exterior entrance offers ideal flexibility for guests or lockout rental use. Every SeaSafe home also includes energy-efficient sealed systems and upgraded insulation as standard, combining strength, efficiency, and thoughtful design. Whether you envision a legacy family estate, luxury island getaway, or investment opportunity, this extraordinary homesite paired with a premier coastal build offers a once-in-a-lifetime chance to own something truly special on Siesta Key. Private tours, lot walks, and builder consultations available upon request.
Listing Agent: Conner Ashley (941-374-1024)
3941 HAMILTON CLUB CIR #9, SARASOTA, FL 34242
$2,290,000102 Days on yellowkey MLS ID: A4685652
REDUCED by $100,000 (4.2%) on 04/02/2026
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: Welcome to coastal luxury living in the exclusive Hamilton Club community on Siesta Key. This beautifully updated 3-bedroom, 3.5-bath waterfront residence offers an exceptional blend of elegance, comfort, and boating convenience in one of the island’s most desirable locations. Designed for effortless everyday living and entertaining, the home features a private elevator, impact-rated windows and doors, and a private 10,000-lb boat lift with quick access to Sarasota’s waterways and the Gulf beyond. A spacious screened lanai overlooking the water provides the perfect setting for morning coffee, evening cocktails, and year-round enjoyment of peaceful coastal breezes. Each spacious bedroom includes its own en-suite bath, offering privacy and comfort for both residents and guests. Thoughtfully updated throughout, the residence showcases renovated bathrooms completed in 2022–2023, kitchen enhancements in 2023, updated lighting, and beautiful new wood flooring, all contributing to a refined coastal aesthetic. Additional improvements include a new water softener and water pressure pump installed in 2025 for added functionality and peace of mind. Offered furnished or unfurnished, the home provides flexibility for immediate enjoyment or personalization to suit your style. Hamilton Club residents will also benefit from upcoming community landscaping improvements this summer and exterior building painting scheduled for 2027, both covered by HOA dues. Ideally located just minutes from Siesta Key’s world-renowned beaches, dining, shopping, and entertainment, this exceptional waterfront residence delivers the ultimate combination of modern upgrades, private boating access, and relaxed island living.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
548A BEACH RD, SARASOTA, FL 34242
$1,725,00053 Days on yellowkey MLS ID: A4691951
Bed: 3 Bath: 3.5 Gar: 1 Liv Area Sq Ft: 2080 Built: 1981Monthly Fee: $1,500 Tax: $16,762 (2025)Community: Tiffany SandsTownhouse
Taxes:$16,762
Remarks: Beautifully renovated Tiffany Sands townhome offering the perfect combination of coastal elegance, spacious living, and an exceptional Siesta Key location with tranquil beach views. This 3-bedroom, 3.5-bath residence features an open, light-filled floor plan designed for effortless island living. Each generously sized bedroom includes a walk-in closet, providing ample comfort and storage. A versatile first-floor bonus room with a full bath and private entrance offers endless possibilities as a guest suite, home office, media room, or additional living space. The home also features a one-car garage with extra storage, multiple expansive decks, and a private patio ideal for enjoying Gulf breezes and picturesque views of Siesta Key's turquoise waters. Just steps away, deeded beach access leads to the world-famous quartz sand beaches of Siesta Key. Ideally situated near Siesta Key Village, residents enjoy convenient access to boutique shopping, acclaimed restaurants, entertainment, and everyday conveniences. Move-in ready and impeccably updated, this is a rare opportunity to own a stylish coastal retreat in one of Siesta Key's most desirable beachfront communities.
5830 MIDNIGHT PASS RD #63, SARASOTA, FL 34242
$598,000214 Days on yellowkey MLS ID: A4672897
0 Days Off yellowkey (back on 5/21/2026)
Bed: 1 Bath: 1.5 Liv Area Sq Ft: 728 Built: 1963Monthly Fee: $1,232 Tax: $6,113 (2024)Community: Jamaica RoyaleCondo
Taxes:$6,113
High School: Riverview High
Remarks: Under contract-accepting backup offers. Experience the best of Gulf-side living in this beautifully renovated 1-bed, 1.5-bath condo on Siesta Key — just steps from the world-famous quartz-sand beaches of Siesta Key. Completely updated from top to bottom, this turnkey coastal retreat features brand-new designer furniture and appliances, making it move-in or rental-ready from the moment you arrive. The spacious layout includes a highly desirable extra half bath—a rare and valuable upgrade that enhances comfort for both owners and guests. Inside, you’ll find premium ceramic tile flooring with a warm, wood-inspired finish, European-imported cabinets and interior doors, and modern quartz countertops. The renovated kitchen blends clean lines with elegant finishes, creating a stylish space for cooking, gathering, or entertaining. Other recent upgrades include a new AC and water heater installed in October 2024, providing year-round comfort and peace of mind. Outside your door, you’ll enjoy direct private beach access to Siesta Key’s legendary shoreline—perfect for daily walks, sunset lounging, or soaking up the Gulf breeze. The community also offers three resort-style pools, giving you multiple options for relaxation, swimming, or enjoying the Florida sunshine in a beautifully maintained setting. Whether you're seeking a personal island getaway, a high-demand investment property, or both, this impeccably finished condo delivers the ultimate Siesta Key lifestyle—modern, effortless, and just moments from the Gulf.
Listing Agent: Noelle Vihrachoff (570-262-4594)
7333 POINT OF ROCKS RD, SARASOTA, FL 34242
$3,495,000416 Days on yellowkey MLS ID: A4651061
0 Days Off yellowkey (back on 6/5/2026)
Bed: 4 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 4566 Built: 2014 Tax: $1,151 (2025)Community: White Beach Fruit Companys SuSpa: YesSingle Family
Taxes:$1,151
Remarks: Repositioned to the market - $500,000 Price Adjustment. Exquisite custom estate in one of Siesta Key’s exclusive neighborhoods. Positioned just across from Gulf-front homes in a private enclave on Siesta Key, this exceptional residence offers the ultimate in island luxury. Masterfully built by Perrone Construction and designed by acclaimed architect Rick Oswald, this custom home is a testament to craftsmanship, quality, and elegant coastal living. Sited on a nearly 22,000-square-foot homesite, the home makes a striking first impression with its stately paver driveway and welcoming entry. Inside, wide-plank engineered hardwood floors and rich architectural detailing define the refined interiors, while soaring beam-and-plank ceilings elevate the spacious great room. The heart of the home is the gourmet kitchen, featuring a Thermador six-burner gas range, custom cabinetry, stone countertops, a generous island and breakfast bar, and an adjacent grilling deck for entertaining. The dining room opens seamlessly to the expansive covered lanai, where you’ll enjoy views of the lushly landscaped backyard oasis. A luxurious main-floor primary suite offers a private retreat with exquisite finishes and spa-style comforts, designed for relaxation and ease. Two upper-level guest suites provide privacy for family or visitors and are easily accessed by either the elegant staircase or a private elevator serving all levels. On the main level, a versatile game room doubles as a fourth bedroom with an adjacent half bath, ideal for guests, hobbies or additional living space. Designed with luxury and peace of mind, this home is built with solid concrete-and-steel frame construction and includes a generator, impact-rated doors and windows, lightning protection, Lutron lighting on the main level, tankless water heaters, central vacuum, and a refreshing outdoor shower. The showstopper? One of the largest residential pools on Siesta Key—nearly 44 feet long—designed for swimmers and hydrophiles alike. You'll find multiple places to relax in the sun or shade, surrounded by lush, tropical foliage and an expansive, fenced yard. Car enthusiasts will appreciate the dual two-car twin garages, while the lower-level non-conforming space offers flexibility for an exercise room, pool cabana or additional recreation space. Though built in 2014, this home rivals new construction in design and condition, with a freshly painted exterior and timeless appeal. Just moments from the world-renowned sands of Siesta Beach and Turtle Beach, with easy access to Turtle Beach Marina, island dining, boutique shopping and downtown Sarasota’s vibrant cultural scene, this residence offers a rare opportunity to own a home that blends location, luxury and lifestyle.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
Listing Agent: Judie Berger (941-928-3424)
5569 SHADOW LAWN DR, SARASOTA, FL 34242
$1,250,00058 Days on yellowkey MLS ID: A4691399
0 Days Off yellowkey (back on 5/31/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2074 Built: 1966Monthly Fee: $17 Tax: $7,312 (2025)Community: Siesta IslesSingle Family
Taxes:$7,312
Remarks: Under contract-accepting backup offers. NEW SOD AND LANDSCAPING JUST INSTALLED, and a brand-new irrigation system was installed as well to keep everything to paradise standards! Welcome to the heart of world-renowned Siesta Key, where coastal living meets modern luxury. This fully renovated, solidly constructed home offers exceptional quality and thoughtful upgrades throughout, including PGT hurricane-impact windows, multiple triple-panel sliding impact glass doors, and a 2019 tile roof. Step inside through beautifully etched, Florida-themed French doors into an open-concept floor plan filled with natural light streaming from the screened lanai. The spacious living and dining areas seamlessly connect to a chef-inspired kitchen, complete with an induction range, griddle, and premium finishes—perfect for entertaining. The home features wood-grain luxury vinyl flooring throughout and tastefully updated bathrooms. The private primary suite is situated on one side of the home and includes an attached office, offering a quiet retreat. Just beyond, you’ll find a generously sized laundry room with a brand-new stackable washer and dryer. The opposite side of the home hosts additional bedrooms and a guest bathroom, providing comfort and privacy for family or visitors. Outdoors, enjoy your own private oasis with a saltwater pool and a brand-new, state-of-the-art pump system. Located in the highly desirable Siesta Isles community, this property is ideally positioned for strong rental potential, offering opportunities for annual, monthly, or seasonal income. Enjoy the convenience of being just a 10-minute walk or 5-minute bike ride to Siesta Key Beach—without the need to access main roads. Move-in ready and perfectly situated, this exceptional home offers the ultimate in coastal living. Schedule your private showing today.
Listing is courtesy of: IRONGATE REALTY INC (941-720-1003)
Listing Agent: Brittany Mccord (941-720-2640)
6157 MIDNIGHT PASS RD #G11, SARASOTA, FL 34242
$449,000725 Days on yellowkey MLS ID: A4615451
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 690 Built: 1974 Tax: $3,758 (2023)Community: Bay OaksCondo
Taxes:$3,758
Tax Year: 2023
Remarks: SOLID CONSTRUCTION & STRATEGIC LOCATION...Discover peace of mind in this resilient first floor condo at Bay Oaks. Convenient carport right outside your door means no waiting for elevators, making it effortless to come and go. The versatile layout of this one-bedroom unit with den provides flexibility for guests and family. Ceramic tile throughout the living and dining room. Lovely outdoor patio surrounded by trees allows back door access to the resort style amenities. Residents and guests enjoy tennis courts, a fishing dock, social room, outdoor grills and a heated pool. This residence rents as a two bedroom as the den has been converted. Catch the free trolley in front of the community to Siesta Beach & the Village. Bay Oaks allows one week rentals and this residence is quite popular! Unit comes TURN-KEY furnished and ready for guests. Freshly painted throughout and brand new water heater.
Listing Agent: Ingrid Caruso (941-539-6233)
5740 MIDNIGHT PASS RD #307, SARASOTA, FL 34242
$1,399,000142 Days on yellowkey MLS ID: A4680695
REDUCED by $71,000 (4.8%) on 05/22/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1466 Built: 1986 Tax: $9,646 (2024)Community: Gulf & Bay Club Ph 6Condo
Taxes:$9,646
Remarks: This Gulf-front, resort-style third-floor end unit offers breathtaking beach and Gulf views, abundant natural light, and an open-concept floor plan within an exclusive 24-hour guard-gated community. Luxurious yet inviting, this beautifully updated 2-bedroom, 2-bath condominium is the perfect coastal retreat. Elegant porcelain flooring flows throughout the residence, enhancing the bright, airy ambiance and reflecting the stunning natural light. The spacious designer kitchen is truly a showpiece, featuring custom wood cabinetry, gorgeous granite countertops, and top-of-the-line appliances. Both bathrooms provide a spa-like experience with stylish finishes and fixtures, including a relaxing jetted tub in one bathroom. Designed for effortless resort living, the oversized laundry room offers additional storage and a deep utility sink for convenience. Every window and sliding glass door has been upgraded to impact-rated standards, while the entire interior has been meticulously renovated with timeless coastal elegance. Enjoy spectacular beach views from the comfort of your living room while watching beach volleyball below. Perfectly positioned close to the activity, yet offering exceptional privacy, the expansive impact-rated sliders invite in refreshing Gulf breezes along with panoramic views of the turquoise water, white sand beach, and endless blue sky. Few properties can offer both direct Siesta Key Beach access and true Gulf-front views just steps from your door. Gulf & Bay Club is situated on 32 beautifully landscaped tropical acres along world-famous Siesta Beach and offers an unmatched resort lifestyle with 800 feet of private beach frontage. Residents enjoy an impressive array of amenities, including: Three swimming pools, including one overlooking the beach State-of-the-art fitness center with cardio, strength training, and yoga facilities Eight tennis courts, including a Har-Tru court Pickleball, basketball, racquetball, and shuffleboard courts Six dry saunas and a hot tub Two freshwater lakes Six BBQ areas and a private picnic island Complimentary Wi-Fi at the clubhouse On-site management Electric vehicle charging stations and car wash area This unit also includes a designated covered parking space, expansive grounds to explore, and endless opportunities to stroll the world-renowned white sand shoreline before falling asleep to the soothing sound of rolling waves. Owners also have access to a private guest suite that can be reserved for visiting family and friends. Located just minutes from the charming shops and restaurants of Siesta Village, this exceptional property is ideal as a full-time residence, luxurious vacation getaway, or outstanding investment opportunity. Experience unforgettable sunsets and embrace the ultimate beachfront lifestyle. This rare slice of paradise on Siesta Beach truly has it all.
Listing is courtesy of: WATERSIDE REALTY LLC (941-346-7454)
Listing Agent: Cindy Furtado (808-937-2376)
145 AVENIDA MESSINA #3, SARASOTA, FL 34242
$630,000264 Days on yellowkey MLS ID: A4667146
2 Days Off yellowkey (back on 3/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1025 Built: 1966 Tax: $5,561 (2024)Community: Villa NavarraCondo
Taxes:$5,561
Remarks: Welcome to this wonderful condominium complex directly on the edge of the Siesta Key Village! This UPSTAIRS unit has been completely remodeled from top to bottom and is absolutely stunning! The opened kitchen features stainless steel appliances, handsome quartz counters, and a tan tiger-look cabinetry. There is all new lighting, fans, receptacles and switches, and a neutral plank-like ceramic tile flooring throughout. The guest bath was completely remodeled along with the primary bathroom that has been expanded for a little extra elbow room. This has a new water heater and HVAC system, new roof in 2025, all new doors, impact windows, ceiling texture and it doesn't stop there. This comes very tastefully turnkey furnished in a warm coastal theme! Relax on your screened patio and look out to palms and foliage and take in the gulf breezes. The pristine beach is 2/10 of a mile away and the SK Village is about 100 feet away with a large selection of restaurants, shopping, grocery, nightlife, and so much more! Don't miss this beautiful condo in the heart of all that Siesta Key has to offer in a very well-run complex.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Joe Cleary (941-650-8485)
4185 ROBERTS POINT CIR #LOT 19, SARASOTA, FL 34242
$3,400,000240 Days on yellowkey MLS ID: A4669769
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3200 Built: 2026Community: Roberts Point 2Spa: YesSingle Family
Taxes:$0
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, masterfully designed in timeless West Indies coastal style and located in the exclusive Roberts Point enclave on Siesta Key. This exquisite residence blends architectural elegance with modern coastal engineering, offering both refined beauty and peace of mind in one of Sarasota’s most desirable island settings. Constructed to the highest coastal standards, this home exemplifies Noah Thomas Builders’ commitment to craftsmanship and durability. With solid concrete block construction, hurricane-rated impact windows and doors, metal roofing, and elevated foundation systems, it’s designed to withstand Florida’s most demanding coastal conditions while maintaining unmatched elegance. The interior features open-concept design, soaring ceilings, and expansive glass sliders that invite natural light and connect seamlessly to the outdoor living spaces. The chef’s kitchen is a showpiece with premium appliances, custom cabinetry, and a large center island ideal for entertaining. The primary suite offers a spa-like retreat with a luxurious bath with freestanding soaking tub, dual vanities, and a spacious walk-in shower. Additional guest suites each feature designer finishes and en-suite baths, while a flexible bonus room provides space for an office, gym, or media retreat. Designed for year-round enjoyment, the outdoor living area includes a fully equipped kitchen, outdoor dining terrace and a resort-style pool and spa. Every space has been designed to take full advantage of Siesta Key’s gentle breezes and year-round sunshine — creating a true outdoor sanctuary that’s both private and unforgettable. The rooftop deck, however, defines this residence. This elevated sanctuary invites you to experience Siesta Key from a completely new perspective. Imagine sunrise yoga sessions with bay breezes, afternoon lounging under a canopy, or unforgettable sunset gatherings framed by fiery Gulf skies. The rooftop deck creates a one-of-a-kind open-air retreat that feels both private and cinematic. Whether hosting guests or escaping for solitude, this rooftop oasis is where the rhythm of island life meets the art of design. Situated on the quiet north end of Siesta Key, Roberts Point is prized for its natural beauty, privacy, and proximity to Siesta Beach, Siesta Village, and downtown Sarasota. Experience West Indies coastal luxury at its finest — where superior design, outdoor living, and hurricane-rated craftsmanship unite in this extraordinary new home by Noah Thomas Builders. All images, renderings, and descriptions illustrate the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications may change during the build process. Pricing, availability, and final details subject to adjustment prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
749 SIESTA DR, SARASOTA, FL 34242
$750,00065 Days on yellowkey MLS ID: O6399340
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1978 Built: 1952 Tax: $11,062 (2025)Community: Bay IslandSingle Family
Taxes:$11,062
Remarks: Investor Special!!Welcome to your next amazing project! Known damage with full or partial rehab. Excellent renovation opportunity on an oversized lot in a highly desirable Siesta Key area. Sold AS-IS with significant upside potential.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Yisbel Bera Damiron (239-265-5102)
8977 MIDNIGHT PASS RD #519, SARASOTA, FL 34242
$585,90020 Days on yellowkey MLS ID: A4694054
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1233 Built: 1974 Tax: $6,490 (2025)Community: Sunrise Cove Sec 3Spa: NoCondo
Taxes:$6,490
Remarks: Wake Up Above Sarasota Bay — Penthouse Views, Coastal Living, and Endless Horizons! Imagine beginning each day from your top-floor residence with breathtaking panoramic views of Sarasota Bay and glimpses of the Gulf of Mexico beyond. From morning coffee to spectacular sunsets reflecting across the water, this exceptional 2-bedroom, 2-bath condominium offers a front-row seat to Sarasota's coastal beauty. Perched on the top level, this light-filled residence showcases expansive water views, abundant natural light, and an inviting floor plan designed for comfortable living and effortless entertaining. Watch sailboats glide across the bay, spot dolphins at play, and enjoy the ever-changing scenery from the comfort of your own home. Whether you're searching for a year-round residence, seasonal retreat, or investment in one of Sarasota's most desirable locations, this residence offers the perfect blend of luxury, convenience, and waterfront charm. Ideally located near world-renowned beaches, vibrant downtown Sarasota, exceptional dining, shopping, arts, and cultural attractions, you'll enjoy the very best of Florida's Gulf Coast lifestyle. Top Floor opportunities with sweeping bay views and Gulf vistas are rare. Experience elevated living where every day begins and ends with unforgettable views. If it can't get any better than this, January and Feburary are rented bringing immediate income to future owner!
Listing Agent: Amy Disalvo (941-780-8080)
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