Location: Sarasota , 34242
Do Not Show Listings
1332 SIESTA BAYSIDE DR #1332C, SARASOTA, FL 34242
$699,90053 Days on yellowkey MLS ID: A4689488
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1280 Built: 1988 Tax: $7,606 (2025)Community: Gulf & Bay Club BaysideCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,606
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Turnkey furnished and beautifully updated, this ground-level 2-bedroom, 2-bath residence in Gulf & Bay Club Bayside offers an exceptional blend of comfort, convenience, and Siesta Key lifestyle. Lightly lived in and meticulously maintained, the interior features a renovated kitchen with stainless steel appliances, solid stone countertops, breakfast bar seating, recessed lighting, custom tray ceiling detail, and an open connection to the main living area that enhances both everyday living and entertaining. Large-format tile flooring runs throughout the main living spaces, while both bathrooms have been tastefully updated with stone counters and tiled shower surrounds. The spacious primary suite offers a relaxing retreat with direct access to the screened lanai, and the guest bedroom is well appointed for family and visitors. Coastal furnishings and decor create a true move-in-ready presentation. The oversized screened lanai expands the living space and provides a peaceful setting surrounded by tropical landscaping, with the community walking path just outside leading to the Intracoastal fishing area, tennis and pickleball courts, and the second pool. Ideally positioned within the community, this residence is also just a short distance to the clubhouse, fitness center, BBQ area, and main pool. Owners and guests enjoy deeded beach access through Gulf & Bay Club across the street, placing world-famous Siesta Beach just a short stroll away. Siesta Beach is currently the No. 1 beach in the U.S. in TripAdvisor's 2025 Travelers' Choice Awards, and Sarasota County provides free trolley service connecting Siesta Key Village, Siesta Beach, South Village, and Turtle Beach. The location also offers convenient access on and off the island, with nearby Siesta Key Village offering shopping, dining, and the relaxed island atmosphere that makes this area so desirable. A private garage completes the package. Whether sought as a personal retreat, seasonal escape, or investment opportunity, this updated Gulf & Bay Club Bayside residence is an outstanding opportunity on Siesta Key.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Shane Lewis (941-685-3252)
5855 MIDNIGHT PASS RD #333, SARASOTA, FL 34242
$499,90074 Days on yellowkey MLS ID: A4685733
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 835 Built: 1976 Tax: $4,433 (2025)Community: Harbor Towers Y & RSpa: YesCondo
Taxes:$4,433
Elementary School: None
High School: None
Middle School: None
Remarks: THE VIEW, THE VIEW, Location, Location. This is IT! RESORT LIVING UNDER $500,000! EVERY AMENITY AT YOUR FINGERTIPS! BEAUTIFULLY APPOINTED, IMPRESSIVE ENTRANCE WITH WATERFALL, WALK INTO THE LUXURY APPOINTED HUGE FOYER--TURN KEY INCOME GENERATING VACATION HOME! STUNNINGLY SELECTED AND DESIGNED UNIT OVERLOOKING THE POOL AND VIEW OF INTRACOASTAL WATERWAY---DESIRABLE 2 WEEK RENTAL WHEN YOURE NOT HERE, BLOCK IT OUT WHEN YOU COME TO ENJOY AND RELAX! ON SITE RENTAL OFFICE TAKES CARE OF IT ALL! Experience the ultimate in luxury coastal living within the waterfront resort community of Harbor Towers Yacht & Racquet Club, one of Siesta Key’s most desirable gated waterfront communities. This beautifully updated sunrise-facing 1 BR, 1 bath home offers breathtaking views of the intracoastal waterway, a completely upgraded oasis to provide modern comfort and elegant coastal style with a gorgeous view of the heated pool and outdoor awning for alfresco dining. Being sold turnkey furnished, this third-floor residence is decorated for immediate enjoyment as a full-time home, vacation getaway, or income-producing investment property. The stunningly renovated interior features hurricane-rated windows, a breathtaking quartz kitchen, vinyl plank wood floors and a stunning bathroom accented in gold. The open-concept living and dining area is filled with natural light, creating a bright and welcoming space ideal for relaxing or entertaining. Included is a washer and dryer, plenty of extra storage space directly across the hall and additional large washers and dryers located on each floor for larger items. Perfect for couples and extended stays, this retreat combines modern coastal finishes, large windows, and resort-style amenities just minutes from world-famous Siesta Key Beach and Siesta Key Village. For boating enthusiasts, you’ll find a beautiful marina with boat slips, as available, through the association. This property offers excellent income potential. Two-week minimum rentals are permitted, and owners may utilize the on-site property management office or manage rentals independently. Residents of Harbor Towers enjoy an exceptional collection of amenities, including: *A large marina *Gulf access (no fixed bridges) *Heated swimming pool and shallow wading pool *Three tennis courts *Fully equipped fitness center with new showers and saunas *Clubhouse with social spaces and large kitchen •Outdoor BBQ and kitchen prep area under a beautiful new awning *For boating enthusiasts, boat slips are available through the association plus an ample kayak storage area. Whether you're seeking a luxurious full-time residence, seasonal retreat, or income-generating property, Harbor Towers offers the perfect blend of resort living and coastal charm. Located near shops and restaurants and across the street from the world-famous Siesta Key Beach, don’t miss this rare opportunity to own your piece of paradise on Siesta Key.
Listing is courtesy of: JUDITH GUZZI & ASSOCIATES LLC (914-490-9032)
Listing Agent: Rosie Dipasquale (614-313-7962)
4900 OCEAN BLVD #201, SARASOTA, FL 34242
$685,000164 Days on yellowkey MLS ID: TB8456849
REDUCED by $14,000 (2.0%) on 05/17/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1978 Tax: $7,974 (2024)Community: Sandy Cove IvSpa: NoCondo
Taxes:$7,974
Tax Year: 2024
Remarks: Enjoy coastal living in this updated 2-bedroom, 2-bath Siesta Key condo, just minutes from Siesta Key Village and the beach. The second-floor residence features a fresh coastal design and a kitchen remodeled in 2020 with granite countertops, stainless-steel appliances, and a washer/dryer. Natural light fills the space through large sliders that open to two spacious lanais with peaceful water and nature views. One of the community’s true highlights is the waterfront area behind the historic Buster Brown clubhouse—perfect for sunsets, shoreline or pier fishing, and watching the Gulf and bay come together. The private pier also provides kayak and water access. Residents enjoy an elevator-accessible lobby, a pool, and a grilling area, creating a relaxed coastal feel ideal for seasonal or year-round living. Being sold fully furnished, with AC replaced in 2022.
Listing is courtesy of: PINPOINT REALTY GROUP LLC (813-805-2112)
Listing Agent: David Broecker, Llc (813-437-5550)
9000 MIDNIGHT PASS RD #5, SARASOTA, FL 34242
$1,350,00095 Days on yellowkey MLS ID: A4683685
REDUCED by $145,000 (9.7%) on 04/29/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1982 Built: 1982 Tax: $7,904 (2025)Community: Turtle CoveCondo
Taxes:$7,904
Remarks: Unique among others for sale on Siesta Key, this 3-bedroom waterfront condo, located on the quiet south end of the island, offers: • Full Views of the Gulf, Blind Pass Lagoon (which connects to the Intracoastal Waterway, the ICW) and Turtle Beach • Two screened porches facing the Gulf from different levels • An easy 5-minute walk through a park to Turtle Beach • A heated waterfront pool steps from the back door • The use of a boat slip and kayak launch directly behind the unit, with direct access to the ICW • A 10-minute boat ride from the slip to the Gulf via Midnight Pass • Living in a quiet area that feels more “residential”, but is within walking distance of 2 waterfront restaurants and only minutes by car or trolley to shopping, restaurants, and entertainment in Siesta Key Village • A back yard lawn and patio • Kayaking in the lagoon and ICW • Fishing in the lagoon from the backyard or community piers directly behind the unit • A pet-friendly environment • A wood-burning fireplace • An oversized 2-car garage with inside access to the unit • A soundproof townhome with no neighbors above or below You will be mesmerized by water views and sunsets from every level of the home and from almost every room in the home. Enjoy spotting pelicans, herons, ibis, jumping fish, and an occasional dolphin or manatee. This 7-unit community, “Turtle Cove”, features the use of 7 equal boat slips, to which lifts could be added. Mature foliage blocks the eastward views of neighboring buildings. The expansive windows and sliding doors are impact-resistant throughout. There is a large, screened, covered porch on the main floor with wall-to-wall windows and sliding doors. The eat-in kitchen is large, bright, and equipped with stainless steel appliances and a convenient pass-through to the dining room. The bedrooms are graced with cork flooring, which is beautiful, quiet, and comfortable. The primary suite faces west with a private, screened porch where you will enjoy sunsets over the Gulf and beautiful reflections on the lagoon. The primary en-suite bathroom features twin sinks, a walk-in shower, and a garden tub. All 3 bathrooms have granite countertops. The primary bedroom and second bedroom have walk-in closets. All bedroom closets are fitted with Closet-Tec fixtures. The third bedroom features 2 single Murphy beds, each complete when opened with dimmable overhead lighting and a power outlet perfect for charging devices while you sleep. The laundry closet is conveniently located near the 3 bedrooms. The downstairs is stunning, with bright light and wall-to-wall impact glass windows and sliding doors to the patio. The 2-car garage is larger than most at 22’ x 24’. A lift (elevator) could be installed in this unit. The location is ideal: a quiet, residential area just 10 minutes from the Stickney Point bridge to the mainland, within walking distance of restaurants, and adjacent to the final, southbound stop of the Siesta Key trolley, a free ride from your home to Siesta Key Village and its shopping, dining, and entertainment venues.
Listing is courtesy of: ZITELLI REALTY NETWORK LLC (813-399-9985)
Listing Agent: Eric Zitelli (813-444-3998)
5400 OCEAN BLVD #8-05, SARASOTA, FL 34242
$690,000209 Days on yellowkey MLS ID: A4670371
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 522 Built: 1970 Tax: $6,969 (2025)Community: Beach TerraceCondo
Taxes:$6,969
Remarks: BEACH TERRACE - STUDIO GULF-FRONT RESIDENCE: YOUR PERFECT SIESTA KEY PIED-À-TERRE Discover your ideal coastal escape at Beach Terrace, perfectly positioned at the end of Siesta Key Village with direct Gulf of Mexico frontage. This charming studio residence offers the perfect pied-à-terre for those seeking an effortless weekend getaway to paradise. Whether you call Sarasota or Lakewood Ranch home, imagine having your own Siesta Key retreat just moments away, a place to unwind, recharge, and embrace the coastal lifestyle whenever you need it. The private balcony frames stunning Gulf views, while the thoughtfully designed interior maximizes space and comfort. Covered parking provides convenient, weather-protected access to your beach escape, while the residence's prime location puts you steps from all the dining, shopping, and entertainment that Siesta Key Village has to offer. No need to drive once you arrive, everything is at your fingertips. Resort-style amenities elevate the experience: enjoy the elevated heated saltwater pool with its spectacular sunset views (truly the best amenity besides the unbeatable location), stay active in the fitness center, gather in the community room, and access the world-renowned Siesta Key Beach directly from the property. The powdery white sand and crystal-clear waters are quite literally your backyard. More than a weekend residence, this is your personal gateway to the Gulf-front lifestyle. Whether it's a spontaneous Friday escape or a planned coastal retreat, your Siesta Key sanctuary awaits. This is the effortless beach lifestyle you've been dreaming of, close to home, yet worlds away.
Listing Agent: Mickey Kiernan (941-402-9115)
625 BEACH RD #602, SARASOTA, FL 34242
$999,000224 Days on yellowkey MLS ID: A4669231
1 Days Off yellowkey (back on 5/17/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1144 Built: 1975 Tax: $8,966 (2024)Community: Tivoli By The SeaCondo
Taxes:$8,966
Remarks: Under contract-accepting backup offers. PRICE REDUCTION OF NEARLY $300,000!!! MOTIVATED SELLERS! DIRECT GULF VIEWS accompany this FULLY REMODELED two-bedroom, two-bath PENTHOUSE offering WEEKLY RENTALS AT TIVOLI BY THE SEA on SIESTA KEY. The residence is presented TURNKEY FURNISHED and ready for immediate occupancy or rental. Comparable units in Tivoli generate APPROXIMATELY $100,000 IN ANNUAL BOOKINGS providing an excellent opportunity to own a piece of Siesta Key while enjoying personal use and potential income. This BEACHFRONT CONDO boasts sophisticated modern design and a tranquil beachside ambiance in a prime, secluded yet connected location. A SPACIOUS 26' X 6' BALCONY OFFERS PANORAMIC GULF VIEWS ideal for enjoying sunrise coffee or sunset cocktails. The living areas feature sleek lines, a neutral palette, and abundant natural light to create an airy atmosphere. The STATE-OF-THE ART KITCHEN is equipped with PREMIUM FIXTURES, TOP-TIER STAINLESS STEEL APPLIANCES including a SUBZERO REFRIGERATOR, STONE COUNTERTOPS, and CUSTOM WOOD CABINETRY. Plush bedrooms provide comfort and serene views, with the master suite featuring direct Gulf views via sliding glass doors, a SPA -INSPIRED ENSUITE BATHROOM WITH HIGH-END FINISHES, and a large walk-in closet. For added assurance, this sixth-floor unit includes MAXIMUM HURRCANE PROTECTION WITH FULL ELECTRIC METAL ROLL-DOWN SHUTTERS. Residents enjoy access to a SWIMMING POOL, poolside cabana with billiard and ping pong tables, ROOFTOP CLUB ROOM WITH EXPANSIVE GULF VIEWS, private tennis and basketball courts, putting green, FITNESS CENTER, and PRIVATE GATED ACCESS to Siesta Key Beach. The community is within walking distance to Siesta Key Village’s restaurants, boutiques, bike rentals, and vibrant nightlife. This property exemplifies elegance, comfort, and the beauty of oceanfront living. It presents a unique lifestyle opportunity for discerning buyers seeking both luxury and investment potential. CALL FOR YOUR SHOWING TODAY!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Susanne Losso (941-928-0023)
4634 HIGEL AVE, SARASOTA, FL 34242
$6,990,00017 Days on yellowkey MLS ID: A4693756
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 3875 Built: 2024 Tax: $36,904 (2025)Community: Ocean Beach RepSpa: YesSingle Family
Taxes:$36,904
Remarks: Start living your dream lifestyle on world-famous Siesta Key in this Pham Development custom-built waterfront British West Indies–style home. Located on a quiet street on the north end of the key—close to the beach, Siesta Key Village and Out-of-Door Academy—and just minutes on and off the island, this residence offers island living at its best. Set on a corner canal-front lot, the two-story home features 5 bedrooms, 5 full bathrooms and 1 half bath, with 3,875 square feet under air, a great room floor plan, soaring 22-foot vaulted ceilings, and walls of windows and doors—including large pocket sliders—that bring in abundant natural light and seamlessly connect indoor and outdoor living. The adjacent dining area provides ample space for entertaining, while the stunning kitchen—completely open to the great room—serves as the heart of the home with a large 9-foot island with extended seating, professional stainless steel gas appliances and a walk-in butler’s pantry. The home also features a fully integrated security system, whole-home sound system and a complete Control4 smart home system. The first-floor owner’s suite offers a private retreat with a walk-in shower, freestanding tub, dual vanities, and a large custom walk-in closet. A laundry room, powder room and mudroom complete the first level, and a 3-car garage provides ample parking and storage. Upstairs you’ll find four en-suite guest bedrooms, an additional laundry area to service them, and an expansive second-level balcony to take in the views. Outdoor living includes approximately 1,502 square feet of covered lanai, an exterior wrap-around porch, and balcony space designed for enjoying the island lifestyle, complete with SunBrite outdoor TVs, and Brazilian hardwood ceilings. The privately gated driveway and fully fenced property are surrounded by lush landscaping, creating a secluded tropical setting with a large swimming pool, champagne spa and expansive pool deck perfect for relaxing or entertaining. A private well supports irrigation. With 31 linear feet of canal frontage, the property features a 31-by-12-foot electric boat lift rated for 6,500 pounds, two jet ski ramps and about a 4.5-foot draft—ideal for boating and enjoying the water, making this oasis the perfect place to enjoy the Siesta Key lifestyle.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
539 AVENIDA DEL NORTE, SARASOTA, FL 34242
$5,499,000133 Days on yellowkey MLS ID: A4679096
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4195 Built: 2026 Tax: $7,935 (2025)Community: Archibald ResubSpa: YesSingle Family
Taxes:$7,935
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. EXQUISITE NEW CONSTRUCTION ON SIESTA KEY: ISLAND LUXURY REDEFINED | Substantial progress has taken place to complete this home. | A rare opportunity to own a meticulously designed custom residence on a prime corner parcel of approximately one-quarter acre, just blocks from world-renowned Siesta Key Beach. Easily accessible from both the north and south bridges, this exceptional new build delivers the ultimate coastal lifestyle where refined interiors meet effortless outdoor living. | SIESTA Key Beach is frequently recognized as one of the best beaches in the U.S. and worldwide, celebrated for its powder quartz sand and crystal-clear waters. Its global reputation has been affirmed by TripAdvisor’s Travelers’ Choice Best of the Best Beaches and Dr. Beach’s annual rankings, making this location as iconic as it is desirable. | MOMENTS from Siesta Key Village, enjoy efficient access to boutique shopping, coffee shops, and acclaimed dining while still benefiting from an extraordinary amenity, your own private boat dock access on the canal just across the street. Spend the day boating and return home with ease, parking your vessel at your own dock, a true island luxury. | THIS thoughtfully curated residence reflects the vision of a hands-on developer deeply involved in every aspect of design, from interior finish selections to landscaping and amenities. Created for buyers who appreciate craftsmanship and fine detail, the home offers 4,195 sq ft of interior living space and an additional 3,756 sq ft of outdoor living, seamlessly blending indoor and outdoor environments. | THE chef’s kitchen is designed for both entertaining and everyday ease, complete with a “dirty kitchen” for behind-the-scenes preparation. The light-filled great room opens to a nearly 50-foot wraparound terrace, creating a spectacular setting for hosting family and friends. | TWO bedrooms are located on the main living level, ideal for guest suites or a secondary primary. Take the stairs or elevator one level up to access the private primary suite featuring a truly custom bath with bespoke tile, finishes, soaking tub and spacious shower that creates a spa-like retreat. Two additional bedrooms with a shared bath complete the upper-level.| FLEXIBLE, elegant, and intelligently executed, the suite of spaces within this home allows effortless tailoring to any family’s lifestyle from multi-generational living to a dynamic entertainer’s paradise. | IMAGINE a home where the luxuries of island beach life blend with a private, resort-style retreat: *Inground pool & spa for cooling off or casual lounging*Rooftop deck for sunset cocktails and starlit conversation*Private boating access just steps from your front door. | AND, when you’re ready for a taste of city life, Downtown Sarasota’s rich cultural tapestry with its farmers markets, arts, galleries, festivals, waterfront parks, and world-class dining is only a short drive away. |THIS is more than a home, it’s an invitation to own your piece of the new Siesta Key lifestyle: elevated, effortless, and extraordinary.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Otte (941-281-5472)
5920 MIDNIGHT PASS RD #1003, SARASOTA, FL 34242
$1,350,00088 Days on yellowkey MLS ID: A4683544
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1334 Built: 1971 Tax: $10,983 (2025)Community: Sarasota Surf & RacquetSpa: NoCondo
Taxes:$10,983
Remarks: Great Opportunity at Sarasota Surf & Racquet Club!! Beautifully turn-key furnished 2BR/2BA condo with a split bedroom floorplan for privacy in Tower 10 Unit 3 right on the beach with a gorgeous view of the Gulf and the beautiful quartz sand beach and shoreline. The onsite rental management team takes care of your investment. You use it when you want and enjoy the great revenue stream coming your way with a rare and great opportunity to take advantage of their 3 night rental minimum policy and managing all the reservations and taking care of the upkeep and cleaning of your unit. This is really exceptional beachfront living on Siesta Key with so many resort style amenities. You have direct access to private Crescent Beach, two heated swimming pools, rental options for tents, cabanas and umbrellas, beachside and poolside BBQ grills, four pickleball courts, three tennis courts (one hard court and two Har-Tru clay) – the only clay courts for a resort community on Siesta Key. There is a fitness center on the property and a recreation room where owners can come together for fun. The interior of this unit has been re-modeled with a lovely coastal look. Both bathrooms have been beautifully re-modeled. The primary bedroom features a king size bed, large walk-in closet and has its own private vanity area and a stunning tiled walk-in shower with a seat and gorgeous glass block. The second bedroom features two queen size beds and large walk-in closet. There is a lanai/room looking out to the beach and Gulf that is perfect for a quiet space for reading or computer work. Washer and Dryer located in laundry room just steps from the unit. This resort style property has it all! Catch the trolley or walk into the Siesta Key village for great shops and lots of great casual dining or more polished dining experiences. Coastal music flows out from the open air fun places for entertainment. Come enjoy Paradise!!!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Jay Mitchell Jr., Pllc (941-586-1754)
1248 NORTHPORT DR, SARASOTA, FL 34242
$2,500,000225 Days on yellowkey MLS ID: A4668459
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3250 Built: 1959Monthly Fee: $293 Tax: $13,819 (2025)Community: Royal Palm HarborSpa: NoSingle Family
Taxes:$13,819
Remarks: One or more photo(s) has been virtually staged. Siesta Key, island living at its best. Welcome to your waterside home where you’ll enjoy a carefree, tropical lifestyle all year long. This home has been nicely maintained along with an extensive addition completed in 2015. The original home included two guest bedrooms with adjoining Jack and Jill bath plus a primary suite. The 1,200-square-foot addition included an oversized en suite with double sinks and vanity area, walk-in closet, three-headed walk-in shower plus a wall of linen closets. The addition also included a flex room used as an office, plus a 22-by-20-foot pantry/laundry area. A truck-friendly spacious garage with room to accommodate four vehicles and 8-foot high garage door was also part of the expansion. New can lighting installed in living room, dining area and kitchen in 2016 along with a new generous-sized kitchen island. The entire home has low maintenance polished concrete flooring that flows seamlessly throughout. Walls of sliding glass doors surround the oversized screened-in lanai and oversized pool. It’s easy to open up the entire house to the great outdoors when entertaining friends and family. For the boating enthusiast, the home sits on a canal with direct access to the Intracoastal Waterway and offers a 27-foot dock equipped with a 10,000-pound boat lift plus a dual jet ski lift. This home exemplifies the best of island living and don’t forget, world famous Siesta Key Beach is only a short distance away.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Peg Davant (941-356-4552)
527 BEACH RD, SARASOTA, FL 34242
$3,195,000102 Days on yellowkey MLS ID: O6384340
INCREASED by $220,000 (7.4%) on 05/15/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1803 Built: 1985 Tax: $18,981 (2025)Community: Sarasota BeachApartment
Taxes:$18,981
Remarks: Discover an exceptional income-generating property in the heart of coveted Siesta Key right on Beach Road! This fully renovated raised multi-unit compound features a spacious 2-bedroom, 2-bathroom unit and a 2-bedroom, 1-bathrooom unit (side by side). An impressive gross income in 2023 and n 2024 (despite hurricane-related downtime), this turnkey investment provides immediate cash flow. Note: This property is zoned an RMF (Residential Multifamily) and is legally able to accept nightly rentals. The property boasts recent upgrades including new AC (2022), updated flooring (2025), modernized plumbing (2022), electrical (2022), and hot tubs (2022). This amazing opportunity is the best cap rate on any house on Siesta Key. Whether you're seeking a high-performing Airbnb rental portfolio or a strategic redevelopment opportunity in one of Florida's most desirable beach destinations, this property delivers both immediate income and long-term appreciation potential. Absentee owner managed; turnkey operation available at on a management fee with all staff staying in place. This house already has engineering drawings to enclose the bottom area adding 2,000 additonal square foot, that would increase rent by or more. This property could be purchased as a portfolio with 5228 Calle Menorca and 6550 Sabal Road.
Listing is courtesy of: BEYCOME OF FLORIDA LLC (804-656-5007)
Listing Agent: Steven Koleno (804-656-5007)
19 WHISPERING SANDS DR #201, SARASOTA, FL 34242
$899,000129 Days on yellowkey MLS ID: A4679748
REDUCED by $51,000 (5.4%) on 05/15/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1464 Built: 1973Monthly Fee: $1,440 Tax: $3,007 (2025)Community: Whispering SandsCondo
Taxes:$3,007
Middle School: Heron Creek Middle
Remarks: Front row FULL Gulf views—just one floor above the sand! Priced below market, this lovely 2 bed/2 bath GULF FRONT tower residence in the premiere Siesta Key property of Whispering Sands represents an opportunity to move right in, and if desired, ultimately take your time to create your own vision and make it your own - and enjoy a lifetime of memories. Don’t hesitate - this is currently the best priced Gulf front tower unit in Whispering Sands. Upon entry, you’re greeted with spectacular, unobstructed 180-degree views of the shimmering aquamarine Gulf. Along with its direct FULL GULF VIEWS, this unit is just one floor away from the sparkling beachside pool and 800’ of Whispering Sands' own private beach. This unit features a nicely remodeled kitchen and great OPEN CONCEPT floor plan, enabling easy interaction between you and your guests. The kitchen includes granite countertops & backsplash, an 8’ breakfast bar, recessed LED & under cabinet lighting, convenient built-in desk, and an abundance of cabinet storage. Experience true Florida living by opening the floor to ceiling sliders in the living room and primary bedroom and take in the fresh salt breezes and the gentle sound of the surf. Both sets of sliders include remote controlled shades. The primary bedroom includes a custom walk-in closet, large vanity area, and ensuite bath with marble countertops, glassed walk-in shower, and linen closet with pullout drawers. A set of glassed French doors with privacy shades opens into the guest bedroom, which can serve as both an office and a bedroom with a fantastic SICO wall bed, desk, and built-ins. This unit is being sold As Is. Whispering Sands is a premiere 55+ Gulf front community offering 2 heated pools, Tower Lounge, Clubhouse – both of which are undergoing remodeling with a completion date in 2026 – beachside Tiki hut and grills, shuffleboard, canoe/kayak storage, and 800’ of private beach on the Gulf. In one of the best locations on Siesta Key, Whispering Sands is right around the corner from the colorful boutiques and restaurants of Siesta Key Village. Don’t miss this opportunity!
Listing Agent: Harriet Stopher (404-316-8944)
6300 MIDNIGHT PASS RD #702, SARASOTA, FL 34242
$1,749,00032 Days on yellowkey MLS ID: A4692155
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1240 Built: 1970 Tax: $9,386 (2025)Community: Crystal Sands 2Condo
Taxes:$9,386
Remarks: Set on the 7th floor of Crystal Sands, this fully updated residence offers a front-row position to the Gulf, with sweeping views stretching south along Crescent Beach toward Point of Rocks. Located in the sought-after “2” stack, the building sits just steps from the sand, creating a rare level of proximity to the shoreline with water views from every room. The 2-bedroom, 2-bath split floor plan is both functional and well-balanced, offering privacy between suites while keeping the main living space open and connected. Wide-plank flooring runs throughout, leading into a light-filled living and dining area that opens seamlessly to the Gulf beyond. A 30+ foot lanai spans the width of the residence and is accessible from both bedrooms and the main living area, creating an easy indoor-outdoor flow and a natural extension of the living space for everyday use. The kitchen is finished with shaker-style cabinetry, quartz countertops, a center island with bar seating, and stainless appliances, designed to feel clean, current, and easy to live in. Both bedrooms are well-proportioned with direct lanai access and calming water views, while the bathrooms have been thoughtfully updated with refined finishes, frameless glass showers, and cohesive tilework that carries the modern coastal aesthetic throughout the home. Residents of Crystal Sands enjoy direct beach access, a Gulf-front pool, and a prime location just minutes from Siesta Key Village’s dining and shops. With its combination of view, proximity to the sand, and updated interiors, this is one of those residences that simply works the moment you walk in.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Curt Ware (941-587-9122)
6548 SABAL DR, SARASOTA, FL 34242
$6,295,00057 Days on yellowkey MLS ID: A4688728
Bed: 9 Bath: 9.5 Gar: 2 Liv Area Sq Ft: 4944 Built: 2024 Tax: $40,057 (2025)Community: Sabal PalmsSpa: YesSingle Family
Taxes:$40,057
Remarks: Discover the ultimate expression of luxury coastal living in the heart of Siesta Key. This extraordinary 9-bedroom, 9.5-bath property is a true architectural showpiece, offering unmatched space, style, and sophistication just moments from world-renowned beaches and vibrant island amenities. Designed with an emphasis on grand-scale living, the home features an expansive great room floor plan that blends effortless comfort with refined elegance. The chef’s kitchen is a standout centerpiece, showcasing a large center island, premium appliances, and an oversized walk-in pantry. Perfect for both everyday living and large-scale entertaining. The dining area is enhanced by custom lighting, creating an inviting ambiance for memorable gatherings. A private elevator provides seamless access to all levels, while the 3-car garage adds convenience and storage flexibility. On the third floor of the home find an additional open family living room space with a wet bar and separate outdoor patio. No detail has been missed including an incredible game room. Every inch of this turnkey furnished home is finished with high-end materials and thoughtful craftsmanship. With nine spacious en-suite bedrooms, this property is ideal for multigenerational living, hosting guests, or maximizing income potential as a luxury rental investment. Outdoor living reaches new heights with a resort-style pool and covered spa, a super fun waterslide, and a putt-putt green are all within the interior of lush tropical landscaping. There are also plenty of outdoor dining and lounging options throughout with several patios and porches including an impressive rooftop deck which offers a panoramic view of the famous Siesta sunsets. Top rated Siesta beach is just a short stroll away as well as shops, the marina and dining. Whether you’re seeking a full-time residence, a second home, or a premier investment opportunity, this Siesta Key BEACH HOUSE delivers an unparalleled blend of luxury, versatility, and island living at its finest.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sabrina Ullmann (203-300-8181)
4136 ROBERTS POINT CIR, SARASOTA, FL 34242
$4,900,000208 Days on yellowkey MLS ID: A4670896
Bed: 6 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 7099 Built: 2008 Tax: $49,708 (2024)Community: Roberts Point 2Spa: YesSingle Family
Taxes:$49,708
Remarks: Discover waterfront living on the coveted north end of Siesta Key. Set along South Coconut Bay with access to Roberts Bay and the Intracoastal Waterway, this sprawling estate offers exceptional privacy, water views, and over 7,000 square feet of refined living space. Soaring ceilings and walls of glass fill the home with natural light, while the open-concept layout and contemporary design create an ideal setting for both everyday living and entertaining. A cylindrical glass elevator serves as a subtle architectural feature within the home’s modern design. The gourmet kitchen is appointed with custom cabinetry, premium appliances, and Sub-Zero refrigeration, complemented by a built-in coffee system, 140-bottle wine cooler, and an oversized island designed for gathering. Multiple fireplaces add warmth throughout the home, while the private home theater with refreshment bar offers an elevated entertainment experience. Outdoor living includes expansive terraces, an infinity-edge pool and spa, and peaceful bayfront surroundings. The primary suite features a private waterfront terrace, fireplace, sitting area, dual walk-in closets, and morning bar. Built with reinforced concrete construction and Anderson hurricane casement windows, the home blends luxury with durability. Additional highlights include a 10-car garage, gym, office, and generously sized guest accommodations. Meticulously maintained, the home also features a freshly painted exterior. A rare opportunity on one of Siesta Key’s most sought-after streets.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Nina Bayan (941-716-5622)
1214 MOONMIST CIR #S-01S, SARASOTA, FL 34242
$429,000191 Days on yellowkey MLS ID: A4672760
REDUCED by $10,000 (2.3%) on 03/31/2026
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 952 Built: 1968 Tax: $3,480 (2024)Community: Polynesian GardensCondo
Taxes:$3,480
Remarks: Totally renovated and updated villa with one bedroom and one full bath plus a bonus room and a large glassed-in lanai. This property is located in beautiful Polynesian Gardens close to the community pool and clubhouse. Extra-large great room and primary bedroom. Bonus room large enough for a queen size bed. Extra-large glassed-in lanai. New appliances, new kitchen cabinets, new tile floors throughout. Impact glass in entry door, PGT impact windows and plantation shutters. Too many improvements to list. List of improvements available. The free Siesta Breeze trolley stops in front of the main entrance providing quick access to the #1 Beach at Siesta Key plus Siesta Village, South Siesta Village and Turtle Beach. Fishing pier also available on Intracoastal.
Listing Agent: Helene Hyland (941-685-2274)
838 NORSOTA WAY, SARASOTA, FL 34242
$4,190,00063 Days on yellowkey MLS ID: A4688144
0 Days Off yellowkey (back on 5/14/2026)
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 3001 Built: 2026 Tax: $11,779 (2025)Community: Bay IslandSingle Family
Taxes:$11,779
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Discover timeless coastal elegance in this upcoming traditional-style new construction home, perfectly situated in the highly coveted Bay Island neighborhood on Siesta Key. Designed to blend modern sophistication with classic charm, this residence offers an extraordinary lifestyle of luxury and tranquility. Set on a 13,815 sqft. homesite, this 3,001 sqft. masterpiece features 5 spacious bedrooms, 5 full bathrooms, 2 half baths, and an office. There is opportunity for a private fitness studio, and there are 3 garage spaces. Thoughtfully curated interiors showcase refined finishes, soaring ceilings, and abundant natural light that capture lush landscaping views throughout. At the heart of the home lies a gourmet chef’s kitchen—a showpiece of design and functionality. A striking quartz waterfall island anchors the open-concept layout, framed by elegant pendant lighting, custom cabinetry, and top-of-the-line stainless steel appliances. Perfectly suited for entertaining or relaxed coastal living, the adjoining living and dining areas flow seamlessly to the outdoors. Step into your private tropical retreat, where a resort-style pool with a champagne spa is surrounded by lush landscaping and swaying palms. Host the family or guests with the covered outdoor kitchen and the dinning space. The outdoor living space is designed for serenity and sophistication, offering the ideal backdrop for gatherings or quiet moments alike. Located in one of Sarasota’s most desirable neighborhoods, this remarkable new construction home offers privacy, convenience, and effortless access to world-class beaches, fine dining, and vibrant cultural attractions. A rare opportunity to own a brand-new luxury residence on Bay Island—where coastal beauty meets timeless design.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
3615 HIGEL AVE, SARASOTA, FL 34242
$699,900150 Days on yellowkey MLS ID: TB8460558
REDUCED by $100,000 (12.5%) on 05/13/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1550 Built: 1951 Tax: $19,585 (2025)Community: Siesta Rev OfApartment
Taxes:$19,585
Remarks: An exceptional opportunity on coveted Siesta Key, this duplex property with two units is offered as-is, with flexibility to restore the existing structure or rebuild to suit your vision. Situated on an expansive lot just minutes from Shell Beach and Siesta Key Public Beach, the property offers convenient access to world-famous sand beaches, dining, and shopping. Whether you are a builder, investor, or owner looking to create a custom coastal retreat or income-producing duplex, this property presents outstanding potential in one of Florida’s most desirable island communities. All offers are welcomed and encouraged.
Listing is courtesy of: GENSTONE REALTY (833-396-0092)
Listing Agent: Tammy Hall (815-791-9910)
5151 SAINT ALBANS AVE, SARASOTA, FL 34242
$1,095,000245 Days on yellowkey MLS ID: A4666929
0 Days Off yellowkey (back on 5/13/2026)
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2314 Built: 1963 Tax: $8,056 (2025)Community: Siesta BeachSpa: YesSingle Family
Taxes:$8,056
Remarks: Under contract-accepting backup offers. Charming Coastal Oasis in the Heart of Siesta Key Nestled on a serene, tree-lined property, this inviting 4-bedroom, 3.5-bath beach-style home offers the perfect blend of tranquility, charm, and central location. Step into a spacious, light-filled living area with an open kitchen layout—ideal for hosting friends and making family memories. Freshly updated with new paint, gleaming quartz countertops, and stainless steel appliances, this move-in-ready home is designed for easy, coastal living. The open floor plan includes a spacious upstairs primary suite with French doors leading to a private balcony—your own quiet retreat. Three additional guest bedrooms are thoughtfully located on the first floor, including a separate guest suite with its own private entrance, offering comfort and flexibility. Step outside into your private backyard oasis featuring a beautiful pool and spa, fully enclosed with a lovely paver deck—perfect for relaxing, entertaining, or enjoying sunny Florida days in peace and privacy. There's still plenty of yard space to garden or play. Slip on your sandals for a short stroll to the world-famous Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor, or bike to the charming Siesta Key Village with its eclectic mix of shops, restaurants, and entertainment. Don’t miss this peaceful, spacious retreat—your own slice of paradise on Siesta Key.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Dianne Anderson (941-350-3513)
6012 W PEPPERTREE WAY #227B, SARASOTA, FL 34242
$699,00087 Days on yellowkey MLS ID: A4685241
0 Days Off yellowkey (back on 3/31/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1180 Built: 1974Monthly Fee: $1,189 Tax: $6,132 (2025)Community: Peppertree Bay IvSpa: NoCondo
Taxes:$6,132
Remarks: Gulf-Side Condo on Siesta Key! Don’t miss this great opportunity to own a beautiful condo with a pool view and just steps from the beach. This spacious first-floor unit features 2 bedrooms and 2 bathrooms, high ceilings, and generously sized rooms that provide plenty of space for family and guests. The condo also includes a private garage and the convenience of an in-unit washer and dryer. Ideally located just a short walk from the pool, fitness center and the beach, this home is part of Peppertree Bay, a desirable beach-to-bay community. Residents enjoy an impressive array of amenities, including a private beach, two heated pools, two clubhouses perfect for gatherings, BBQ areas, tennis and pickleball courts, a fitness center, sauna, and a fishing pier. On-site management adds to the ease of ownership, making this an ideal full-time residence, vacation home, or investment property.
Listing is courtesy of: PEPPERTREE BAY REALTY INC (941-914-3380)
Listing Agent: Cheryl Santelli (941-924-8305)
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