Location: Sarasota , 34242
Do Not Show Listings
604 NORSOTA WAY, SARASOTA, FL 34242
$4,490,00034 Days on yellowkey MLS ID: A4698055
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 4536 Built: 1926 Tax: $31,312 (2025)Community: Bay IslandSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$31,312
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Currently under renovation. Welcome to an exceptional newly updated residence on he highly coveted Bay Island neighborhood on north Siesta Key, where timeless coastal architecture and modern luxury come together in one of Siesta Key’s most desirable locations. Situated on an expansive 0.48-acre homesite, this beautifully designed home offers 4,536 square feet of refined living space with a total of 5 bedrooms, 5 full bathrooms, and 1 half bath. Thoughtfully enhanced with new finishes, designer upgrades, and premium appliances throughout, the home also enjoys glimpses of the ocean water that complement its tranquil coastal setting. A private gated driveway leads to a detached 4-car garage, and guest suite with 2 bedrooms and 2 bathrooms, providing both privacy and convenience. At the center of the residence is a stunning chef’s kitchen designed for both everyday living and entertaining, complete with premium Sub-Zero refrigeration, professional-grade gas appliances, custom cabinetry, elegant stone surfaces, and a spacious center island. The adjoining great room and dining area seamlessly connect to the outdoor living spaces, while the luxurious primary suite provides a private retreat with a spa-inspired bathroom, generous walk-in closets, and peaceful views of the surrounding tropical landscape. Step outside to your own private coastal oasis, where a screened pool and expansive pool deck create the perfect setting for relaxation and entertaining year-round. Beautifully landscaped grounds and thoughtfully designed outdoor living areas enhance the home's resort-style atmosphere. Located just moments from Siesta Key’s world-renowned beaches, waterfront dining, boutique shopping, and Sarasota’s vibrant cultural amenities, this exceptional residence offers an unparalleled blend of privacy, sophistication, and convenience. A rare opportunity to own a luxury home on Norsota Way, where exceptional craftsmanship and the coveted island lifestyle come together. Photos and renderings may include virtual staging and virtual enhancements intended to illustrate the property's anticipated completion and design.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
225 HOURGLASS WAY #103, SARASOTA, FL 34242
$500,000315 Days on yellowkey MLS ID: A4664460
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969 Tax: $3,529 (2024)Community: Whispering SandsCondo
Taxes:$3,529
Tax Year: 2024
Remarks: Virtually Staged. GREAT PRICE IMPROVEMENT! Welcome to this RARE, 2 bed/2 bath, double lanai corner residence with peaceful lagoon views in the premiere Gulf front property of Whispering Sands! Nestled in the desirable Sunset House building, this freshly painted, updated unit offers a quiet, private setting, with serene views of lush landscaping and the shimmering lagoon with its abundant fish, turtles, and aquatic life. A wonderful entry hall leads into a spacious OPEN CONCEPT floor plan, where the kitchen, living and dining areas flow together to create a wonderful, flexible gathering space. The living space has been extended into what was originally an enclosed 24' x 7' lanai, resulting in the creation of additional valuable interior living space under air, flanked on all sides with floor to ceiling sliders. Sliders open into a private, sunny brick paver patio, perfect for grilling, gardening, or simply relaxing in the surrounding natural beauty. You'll enjoy hosting friends and family in your NEW 2025 kitchen featuring granite countertops, LG stainless appliances, soft-close cabinetry, tile backsplash, breakfast bar, & tray ceiling. The primary and guest bedrooms each include a set of charming French doors that open into the tiled, screened and glassed lanai with direct views into the lagoon. Updated in 2024, both bathrooms include new granite countertops, soft close vanities & fixtures, and recessed lighting. All of the sliders in this unit are Miami Dade hurricane impact rated. 2024 HVAC system. 2025 water heater. Whispering Sands is a 55+ Gulf front community ideally situated just steps to the colorful shops & restaurants of Siesta Key Village offering two heated pools, clubhouse with catering kitchen and fitness rooms currently undergoing complete remodeling, canoe/kayak storage, beachside Tiki Hut & grills, and 800’ of its own beach access on the Gulf! Thoughtfully updated, inviting, and perfectly private, this peaceful corner retreat offers the perfect blend of indoor/outdoor living on beautiful Siesta Key.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
5026 CALLE MINORGA, SARASOTA, FL 34242
$875,000103 Days on yellowkey MLS ID: A4690532
REDUCED by $24,000 (2.7%) on 06/25/2026
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1240 Built: 1954 Tax: $11,005 (2025)Community: Mira Mar ExitSingle Family
Taxes:$11,005
Remarks: This property in the heart of Siesta Key Village is zoned OPI — Office, Professional, and Institutional — making it one of a very small number of properties in the Village where a business can legally operate. Buyer to verify intended use with the county. The structure is a furnished 3-bedroom, 1-bath cottage with a full kitchen, Florida room, and laundry. The metal roof is approximately 8 years old. Interior paint is fresh. A shell driveway provides on-site parking — genuinely rare in the Village, where street parking is limited and pedestrian traffic is constant. The location positions it within blocks or a trolley ride to Siesta Key Beach, boutique retail, and a concentration of restaurants and services that draw consistent year-round foot traffic. The property has been used residentially and is configured for either continued residential occupancy or professional office conversion. This is a niche offering suited to professionals, investors, or operators looking for a permanent presence in Siesta Key Village. There is no HOA. Lease minimum: 1 month. Financing: cash or conventional.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Kim Donahue (941-724-2587)
925 BEACH RD #310, SARASOTA, FL 34242
$575,000331 Days on yellowkey MLS ID: TB8422646
REDUCED by $24,000 (4.0%) on 06/24/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 753 Built: 1972Monthly Fee: $908 Tax: $5,378 (2024)Community: La SiestaCondo
Taxes:$5,378
Elementary School: None
High School: None
Middle School: None
Remarks: Siesta Key 2BR/1BA condo updated in 2021 with sweeping Gulf views from a private balcony. Bright, open living area flows to the outdoors. Prime island location close to dining and shops. A standout coastal retreat or investment. Come enjoy the Siesta Key lifestyle!
Listing is courtesy of: BRICK STREET REALTY (727-512-6615)
Listing Agent: Colin Mooney (727-512-6615)
225 HOURGLASS WAY #106, SARASOTA, FL 34242
$500,000160 Days on yellowkey MLS ID: A4683200
REDUCED by $75,000 (13.0%) on 05/08/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $3,860 (2025)Community: Whispering SandsCondo
Taxes:$3,860
Remarks: Step into your own island retreat with this rare END unit in the highly sought after GULF FRONT property of Whispering Sands! Perfectly positioned with a full length screened & glassed lanai overlooking the picturesque lagoon and lush tropical landscaping, this residence captures a peaceful, serene setting with a touch of everyday luxury. Thoughtfully updated and designed for effortless living, the OPEN CONCEPT floor plan features non-slip porcelain tile placed on the diagonal, skip trowel ceiling, and a spacious light-filled living space with an additional, sunny, west facing window. The nicely RENOVATED kitchen is a standout, offering granite countertops, colorful tile backsplash, a 9’ breakfast bar, white soft-close cabinetry, and a suite of GE, Whirlpool, Frigidaire, and LG appliances, all enhanced by overhead recessed, dimmable LED lighting. The cabinetry and granite extend into the entire length of the dining area, creating additional storage and an elegant serving space ideal for entertaining. The original interior living room sliders have been removed to seamlessly incorporate the lanai, transforming it into a sun-drenched sunroom that expands your cooled living space and invites the outdoors in. Just outside, a small brick paver patio off the sunroom offers the perfect spot for grilling, sunning, or unwinding after a day at the beach. Both bathrooms in this unit have been tastefully updated with NEW vanities, fixtures, and cabinetry. Additional highlights include a complete set of 2016 hurricane impact sunroom sliders and 2025 water heater. At Whispering Sands, every day feels like a vacation—with 800’ of PRIVATE beach, two heated pools with new travertine tile decks, clubhouse – currently undergoing a complete remodel which will include a catering kitchen and fitness rooms – beachside Tiki Hut, grills, and canoe/kayak—all just a short stroll to the vibrant shops and dining options of Siesta Key Village. Your island getaway awaits!
618 AVENIDA DE MAYO, SARASOTA, FL 34242
$1,200,00089 Days on yellowkey MLS ID: A4692001
Bed: 5 Bath: 4.0 Liv Area Sq Ft: 2961 Built: 1948 Tax: $8,283 (2025)Community: Sarasota BeachSingle Family
Taxes:$8,283
Remarks: This Charming Old 1948 Bungalow located just 3 Blocks behind Siesta Key Village and 4 Blocks to Siesta Key Beach!! It is quite the Interesting Property! It was converted into a Triplex many moons ago. It can easily be converted back to a single family residence. Currently, there are 2 Beds and 2 Baths downstairs and 2 Beds 1 Bath upstairs. There are 3 Kitchens, 3 Liv Areas 2 down, 1 up and there is a Bonus Rm down as well as a Screened in Patio on the front West side of the Home, an Open Patio on the East Side and a Closed in Upstairs. And, there's more... At the Rear of the Property is a Cottage, perfect for a Mother In Law Suite or Rental. It is a 1/1 with a full Kitchen and Liv Area. The grounds are Etherical, as there are private little Sitting Areas for each sector and in the center of the Backyard there is a Wash House for Laundry as well as an attached Storage Shed for Gardening. There are additional Outside Storage Units for each of the apartments, again, really a cool old school house with so much to offer. Make it back into a single family or keep it the way it is and rent the house and utilize the cottage for a personal vacay spot! Questions, call me!!
Listing is courtesy of: BLAKELEY & ASSOCIATES REALTY (941-567-3100)
Listing Agent: Lisa Blakeley (941-809-1647)
$1,200,000182 Days on yellowkey MLS ID: A4680244
Bed: 5 Bath: 0.0 Liv Area Sq Ft: 2961 Built: 1948 Tax: $8,283 (2025)Community: Sarasota BeachApartment
Remarks: Welcome to Old World Siesta Key...this 1940s Bungalow Home was converted approx 40 years ago into a Triplex and a Cottage was added at the rear of the property. Siesta Key is World Renown for it's White Powdery Sand Beaches and is so convenient to the Mainland and all the Attractions Sarasota has to offer such as the Arts, St Armands and Unbelievable Shopping. The Property is located approximately three blocks behind Siesta Key Village, the Hub of Restaurants, Nightlife, and Shops, and there you will find this Graceful Triplex and Cottage. There are several Private Patios as well as Open Areas for Outdoor Entertainment and Relaxation both in the Front and Rear of the Triplex. There are Storage Units for Each Rental and there is a Shared Laundry Area in the middle of the Backyard. Convenience is really key for this Property as you can Walk to the Beach or the Village in 15 Minutes. Island Life is Unique, Exciting, Colorful but can also be Quiet and Slow, it's the perspective of the Offering and it's a sought after way of living. For the past 20 years the units have been long term rentals. Some of the tenants have been there for years and all four would like to stay and continue their Florida Island Lifestyle. Rents shown are the Expected rents that could be charged as the Owner currently charges less... just his way of doing business. There is one option that could change the dynamics and that would be to keep the Triplex as long term rentals and use the rear Cottage as an AirBNB and Owners Use unit. This would drastically change the income stream. The water and internet/cable is currently paid for by the Owner and the Electric is split between the Tenants based on unit size, of course all of this is subject to change based on the New Owner's intentions. This is an Amazing Opportunity to have both Income and Personal Enjoyment all wrapped up with a Special Place we call Siesta Key Living!
617 SIESTA DR, SARASOTA, FL 34242
$949,90036 Days on yellowkey MLS ID: A4697947
Bed: 4 Bath: 4.0 Liv Area Sq Ft: 2709 Built: 1939 Tax: $32,740 (2024)Community: Bay IslandSingle Family
Taxes:$32,740
Remarks: BANK OWNED... Located in Highly desirable Bay Island Subdivision The Gateway to Siesta Key... This 4 Bedroom 4 Bath is located within the City limits Sarasota with allow short term rentals. Upgrades include a Metal roof with solar panels, Crown Molding and Brick paver Driveway. This property sustained damage from the 2024 hurricanes. Great Location to just drive to World famous Siesta Key Beach and Downtown Sarasota. A Great Place to spend the season or a lifetime. Property is being sold as-is . Build your own Equity. WELCOME HOME!!!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Gary Hoskins (941-809-7709)
546 FREELING DR, SARASOTA, FL 34242
$12,500,00036 Days on yellowkey MLS ID: A4694822
Bed: 5 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 4353 Built: 2027 Tax: $17,536 (2025)Community: Bay IslandSpa: YesSingle Family
Taxes:$17,536
Remarks: Pre-Construction. To be built. Discover an extraordinary opportunity to own an expansive double lot of 0.52 acres on North Siesta Key with this single-story, new construction transitional modern-style luxury home by Pham Development. Offering 170 feet of deep-water canal frontage, the residence features 4,353 square feet under air and 15,453 square feet under roof. With 5 bedrooms, 5 full bathrooms, 2 half baths, and a designated private office, the home showcases soaring 17.5-foot vaulted ceilings and a striking glass wine wall, complemented by designer finishes that fill the interiors with natural light and tranquil water views. Across the canal, lush landscaping provides a serene and private backdrop, with flexibility to customize finishes and style. Designed for both comfort and entertaining, the open-concept living spaces flow seamlessly to a resort-style outdoor retreat. The expansive back patio is equipped with remote-controlled electric mosquito screens, allowing you to enclose the space at the touch of a button for year-round enjoyment. Enjoy a spectacular pool with a champagne hot tub spa, a generous patio, and a fully equipped outdoor kitchen perfect for alfresco dining. A scenic path leads to your private dock with a state-of-the-art electric system and space for a boat up to 37 feet, offering smooth access to the bay and Gulf. The primary suite is a private sanctuary with spa-inspired amenities and dedicated quarters. A chef’s kitchen anchors the heart of the home with premium appliances and refined finishes. An elegant circular driveway creates a grand entrance, while the expansive ground level offers room for up to 10 cars, complemented by an impressive 10-car garage—ideal for collectors or additional storage. This exceptional waterfront residence delivers effortless luxury and refined coastal living.
3750 BAYOU LOUISE LN, SARASOTA, FL 34242
$12,900,000134 Days on yellowkey MLS ID: A4686535
Bed: 5 Bath: 6.5 Gar: 4 Liv Area Sq Ft: 5273 Built: 1997 Tax: $61,016 (2025)Community: Siesta Rev OfSpa: YesSingle Family
Taxes:$61,016
Remarks: Tucked on the coveted north end of Siesta Key, this extraordinary double-lot point estate is positioned at the tip of a protected peninsula, offering panoramic water views and unforgettable sunsets. Surrounded by water and set directly across from protected parkland, the setting feels like your own private island. The property features three separate structures: a main residence, a guest house, and a separate waterfront cabana with bath. In total, the compound offers six bedrooms and six bathrooms, with gourmet kitchens in both the main house and guest house — each outfitted with high-end appliances throughout — ideal for multigenerational living, guest accommodations, or an exceptional private retreat. Throughout both residences, the finish detail is exceptional. Designer-selected materials create a cohesive and elevated aesthetic carried seamlessly across the entire compound. Custom wood flooring with intricate stone inlays, handcrafted stairwells featuring wood and stone risers, extensive crown molding, and refined architectural millwork highlight the level of craftsmanship invested in every space. Specialty stonework and thoughtfully curated finishes blend warmth with sophistication, creating interiors that feel timeless, substantial, and unmistakably high-end. Outdoor living is nothing short of spectacular. A dramatic infinity-edge pool with swim-assist system overlooks the water, enhanced by a striking waterfall feature that spills elegantly into the pool. New pool equipment (2025) supports the system. Natural rock waterfront frontage and a sculptural rock formation lead down to the shoreline, creating a one-of-a-kind coastal backdrop. Two docks serve the property — one with a double lift — offering outstanding boating access and rare protection on both sides of the point, with additional lift capacity for multiple watercraft. An outdoor shower provides added convenience after boating or swimming. Perched at the edge of the peninsula, the waterfront cabana and adjacent hot tub create a private, spa-like retreat suspended over the water — an unforgettable setting to take in sweeping sunset views. The residences were renovated separately: main house (2009) and guest house (2012). All A/C units have been renewed recently, along with the electric unit, and a new transformer (2024) services both properties. Sonos surround sound extends throughout all structures. Located on the highly desirable north end of Siesta Key, the estate offers convenient on-and-off island access while remaining just minutes from Southside Village and downtown Sarasota.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Nora Johnson (941-809-1700)
1203 SIESTA BAYSIDE DR #1203-D, SARASOTA, FL 34242
$498,000100 Days on yellowkey MLS ID: A4690769
0 Days Off yellowkey (back on 6/23/2026)
REDUCED by $27,000 (5.1%) on 04/27/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 959 Built: 1988 Tax: $5,340 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$5,340
Remarks: Under contract-accepting backup offers. Sellers Are Highly Motivated! Welcome to your slice of paradise on world famous Siesta Key, just steps from the powdery white sands of Siesta Beach, recently ranked the number one beach in the United States. This beautifully updated one bedroom, one bathroom residence is the perfect blend of comfort, style, and location, ideal as a primary home, vacation retreat, or income producing investment with weekly rentals allowed. From the moment you enter the gated community of Gulf and Bay Club Bayside, you are surrounded by lush tropical landscaping and a sense of pride in ownership that truly sets this community apart. This impeccably maintained residence offers easy single level living with a bright and open layout, finished in a warm neutral palette. The living and dining areas are enhanced with charming details such as wainscoting, while the updated kitchen features stainless steel appliances, beautiful countertops, and well-appointed cabinetry, all flowing seamlessly into the main living space. The oversized primary bedroom offers a peaceful retreat with a large walk-in closet, while the upgraded bathroom features a stunning tile shower, dual sinks with quartz countertops, and excellent storage. A private laundry area adds convenience, and with no carpet throughout, the home is clean, modern, and move in ready. The AC and water heater were both replaced in 2022. Enjoy your morning coffee in the adorable dining nook or unwind in the bright and airy lanai, the perfect place to relax at the end of the day. This residence also includes a rare one car garage and private driveway, making island living effortless. Gulf and Bay Club Bayside offers an exceptional array of resort style amenities including two heated pools, a clubhouse, fitness center, saunas, pickleball and tennis courts, BBQ areas, walking paths, scenic ponds with fountains, and a fishing pier on the Intracoastal Waterway where you can enjoy sunsets, dolphins, and passing boats. Private deeded beach access just across the street makes it easy to enjoy the turquoise waters and world-famous quartz sand whenever you choose. Ideally located between Siesta Key Village and Stickney Point Road, you are moments from top rated dining, boutique shopping, live entertainment, and water activities. The Siesta Key Trolley provides easy access across the island, making every day feel like a vacation. Offered furnished and thoughtfully updated, this residence truly lives larger than expected and is ready for immediate enjoyment. Whether you are looking to relax, entertain, or invest, this is an incredible opportunity to own in one of the most desirable communities on Siesta Key. Schedule your private showing today and experience the coastal lifestyle you have been dreaming of.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Rachelle Golden (941-538-8998)
4660 OCEAN BLVD #Q1, SARASOTA, FL 34242
$525,000342 Days on yellowkey MLS ID: A4659204
3 Days Off yellowkey (back on 6/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1971 Tax: $7,101 (2024)Community: Sea VillageCondo
Taxes:$7,101
Remarks: Under contract-accepting backup offers. PRICED TO SELL! NEW impact-rated sliding glass doors were installed in June 2026, providing enhanced storm protection and complementing the home’s existing hurricane-impact windows. 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 additional protection 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 is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Halie Monde (941-735-4707)
1035 SEASIDE DR #308, SARASOTA, FL 34242
$2,550,00085 Days on yellowkey MLS ID: A4692379
REDUCED by $50,000 (1.9%) on 06/23/2026
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1646 Built: 2023 Tax: $21,387 (2025)Community: Ten35 SeasideSpa: YesCondo
Taxes:$21,387
Middle School: Sarasota Middle
Remarks: Gulf-Front Luxury with Investment Appeal Experience elevated beachfront living at Ten35 Seaside, a boutique Gulf-front community on the quiet southern end of Siesta Key. This beautifully designed 2-bedroom, 2.5-bath residence offers private beach access, resort-style amenities, and strong luxury rental potential. The open-concept layout features Wolf and Sub-Zero appliances, custom cabinetry, sleek coastal finishes, and spacious living areas filled with natural light. Sliding glass doors open to a private terrace perfect for enjoying Gulf breezes and sunset skies. The primary suite offers a spa-style bath and walk-in closet, while the guest suite includes built-in bunk beds for added flexibility and rental appeal. Residents enjoy a beachfront pool and spa, private cabanas, fitness center, and direct access to Siesta Key’s world-famous beaches — all just minutes from Siesta Key Village and downtown Sarasota. Ideal as a luxury beachfront retreat, full-time residence, or income-producing coastal investment property. Buyer to verify rental policies, restrictions, and all room dimensions.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Rex Glasson (941-587-6135)
3440 GULFMEAD DR, SARASOTA, FL 34242
$12,900,000188 Days on yellowkey MLS ID: A4679384
REDUCED by $1,050,000 (7.5%) on 06/23/2026
Bed: 5 Bath: 5.0 Gar: 6 Liv Area Sq Ft: 6596 Built: 2008 Tax: $58,421 (2025)Community: Gulfmead EstatesSpa: NoSingle Family
Taxes:$58,421
Remarks: Discover a rare opportunity to enjoy pristine Gulf views, aquamarine waters, and a deep-water dock on the very North end of Siesta Key, just minutes to downtown Sarasota. One of Siesta Key’s most stunning and secluded waterfront sites — a residence offering a rare combination of historic significance, panoramic views of Big Pass, and exceptional structural integrity. Located approximately 200 feet south of civic leader Henry Higel’s early 20th-century Higelhurst Hotel, the pioneering developer’s beloved coastal breezes still beckon family and friends to enjoy swimming, water sports, boating, fishing, shoreline picnics, and direct, no-bridge access to the sparkling Gulf. Multiple covered porches and expansive windows provide front-row views of vivid sunsets and frolicking dolphins. Named for its pineapple stair finials symbolizing welcome, the Pineapple House was built in 2008 with an engineer-homeowner’s meticulous eye for detail. Constructed on pilings and grade beams, the home is set on a 31,293-square-foot lot and encompasses 6,596 square feet under air, with more than 13,000 total square feet. Designed by Diane Weinman with a refined Boca Grande aesthetic and built by ML Collingwood, the dwelling projects enduring quality, thoughtful engineering, and elevated coastal living. Enter through the impressive double doors to a sensual treat of symmetry and light. Main-level windows crowned with transoms frame views of the tropical blue sky. Walnut engineered flooring, Jerusalem stone, eight-foot doors, custom millwork, and generous closets enhance both functionality and beauty throughout. Scaled to feel both warm and elegant, the interiors are enriched with refined finishes and thoughtful architectural detailing. Living spaces encompass a formal dining room with butler’s pantry, living room, bookcase-lined library or sitting room, private office with built-in desk and cabinetry, dedicated home gym, and a flexible gathering room. A second primary or guest suite on the main level offers a private sitting area, breakfast bar, screened porch, and picture-perfect water views. An elevator conveniently serves all three floors. The chef’s kitchen anchors the main living areas with honed granite countertops, Sub-Zero appliances, custom Campbell cabinetry, and a walk-in pantry, opening to casual dining spaces and sun-filled outdoor porches. Upstairs, the primary suite is a tranquil retreat featuring a spa-inspired bath, oversized walk-in closet, shaded terrace, and outdoor shower. The expansive dock features two boat lifts: one 22,000-pound lift suitable for a 32- to 36-foot vessel and a second 10,000-pound lift. A humidity-controlled four-car tandem garage and a separate two-car garage accommodate up to six vehicles along with extensive marine and recreational gear. Solar panels and a 30kW generator underscore the home’s focus on energy efficiency and resilience. Outdoor living is highlighted by a 20,000-gallon heated saltwater lap pool surrounded by Shellcrete patios and Ipe decking. A perched beach with fire pit and swings welcomes gatherings overlooking Big Pass, while a 75-foot rear setback ensures privacy within a lushly landscaped yard. Rich in history, resilient and luxurious, intimate and refined, this is Sarasota waterfront living at its most authentic and coveted. Photos 1 and 2 reflect the new colors that the home is being painted.
Listing Agent: Jennifer Linehan (941-266-7555)
1001 POINT OF ROCKS RD #208, SARASOTA, FL 34242
$1,195,00037 Days on yellowkey MLS ID: A4697514
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1200 Built: 1988 Tax: $10,536 (2025)Community: Siesta Sands ResortCondo
Taxes:$10,536
Remarks: Gulf view condominium at the Siesta Sands Resort, at the southern tip of world-famous Crescent Beach on Siesta Key. This second-floor end unit, featuring two bedrooms, two baths and two private balconies, has been completely renovated, tastefully decorated and furnished, with in-unit laundry, a reserved parking space and a nice view of the blue waters of the Gulf, as well as a good view of one of the resort’s pools. The resort-style condominium is on a beautiful private beach featuring what has been rated as the whitest sand, consisting of 99 percent pure quartz, which stays cool under your feet. Residents of Siesta Sands enjoy an impressive array of resort-style amenities, including beach service for lounge chairs and umbrellas, two heated pools, community Wi-Fi, a poolside gazebo, gas grills, an exercise room and serene bamboo lounge. This boutique beachfront community offers a secluded, gated retreat with only 31 units and exclusive private beach access to Crescent Beach. The unbeatable location places you near Siesta Key's South Village. Siesta Sands allows weekly rentals and has an excellent on-site rental office to keep the condominium rented when not being utilized for personal use. The Point of Rocks is an area known for its coral formations and marine life, ideal for fishing or snorkeling. This resort condominium is offered turnkey furnished with solid rental history and further bookings in place. This is must-see. Don’t miss out.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Ziad Sleit (941-928-5493)
5830 MIDNIGHT PASS RD #3, SARASOTA, FL 34242
$649,00037 Days on yellowkey MLS ID: A4697756
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1960 Tax: $3,964 (2025)Community: Jamaica RoyaleVilla
Taxes:$3,964
Remarks: Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. This completely updated, open floor plan. Upgrades galore!! Fantastic rental history! The HOA installed a new roof on the property in 2023, too! Jamaica Royale allows short term rentals so this could be a great investment property or keep it for your own second home. This is the closest gulf side weekly rental property to the main public beach offering 3 swimming pools, grilling stations and shuffle board. Make this great property yours today at a value!
Listing is courtesy of: TIDELINE REAL ESTATE BROKERS (941-587-1669)
Listing Agent: Steve Cavanaugh (941-587-1669)
6140 MIDNIGHT PASS RD #606, SARASOTA, FL 34242
$1,279,00066 Days on yellowkey MLS ID: A4694184
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1521 Built: 1967Monthly Fee: $1,354 Tax: $13,588 (2025)Community: Horizons WestSpa: YesCondo
Taxes:$13,588
Remarks: Nestled on the renowned shores of Siesta Key, Horizons West offers a truly exceptional waterfront living experience where breathtaking panoramic views and unforgettable sunsets become part of everyday life. This meticulously cared-for two-bedroom, two-bathroom residence, elevated on the sixth floor, delivers unparalleled luxury and privacy in a home that has never been in a rental program, resulting in exceptionally minimal wear and tear. Following a comprehensive top-to-bottom renovation that stripped the unit to its concrete box, every inch of this residence reflects the pride of true ownership with timeless, sophisticated design. The gourmet kitchen and bathrooms feature custom Harlan solid wood cabinetry sourced from Indiana, sleek granite countertops, and a premium suite of KitchenAid stainless steel appliances. Modern infrastructure is seamlessly integrated throughout, including Cat 6 data outlets, a commercial-grade PakEdge Wi-Fi router, and a whole-home surge protector. Comfort is guaranteed with a brand-new HVAC system installed in July 2025, complete with an air scrubber for active air purification. The home is an audiophile’s dream with a built-in multi-zone sound system featuring Vienna Acoustics speakers and a Marantz receiver. Elegant touches abound, from recessed LED and runway lighting to motorized Hunter Douglas window treatments and custom California Closets. Offered turnkey and fully furnished, the residence includes high-end pieces like an American Leather sofa and Westin Heavenly Bed® mattresses, along with the rare convenience of a roughed-in space for an in-unit washer and dryer. Horizons West spans 11 acres with over 300 feet of deeded beach access, a beachside pool and spa, and a serene bay-side park with a day dock. This is a rare opportunity to own a residence finished to the highest standard on the world-renowned shores of Siesta Key. Welcome home.
Listing is courtesy of: ENGEL + VOELKERS SARASOTA (941-388-9800)
Listing Agent: Brian Partie, Jr, Pa (941-544-8298)
19 WHISPERING SANDS DR #204, SARASOTA, FL 34242
$995,000172 Days on yellowkey MLS ID: A4681694
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,440 Tax: $8,669 (2025)Community: Whispering SandsCondo
Taxes:$8,669
Remarks: Embrace the rare opportunity to own a GULF FRONT residence in the coveted Siesta Key community of Whispering Sands – where breathtaking FULL GULF views, an unbeatable location, and endless potential come together. This 2 bed/2 bath 2nd floor tower unit showcases panoramic vistas of the shimmering Gulf, on 800’ of your own PRIVATE quartz sand beach, and the nightly spectacle of vibrant symphonies of colorful sunsets from your expansive 24’ open-air balcony. Offered in largely original condition, this residence is a true blank canvas—an exceptional value in today’s buyer’s market and the perfect chance to design and remodel from top to bottom in your own personal style. Create the coastal retreat you’ve always envisioned while investing in a premier Gulf front address known for its timeless appeal and strong long-term desirability. Reputable contractor names are available to help bring your vision to life. Life in the sought after 55+ community of Whispering Sands is peaceful and resort inspired. Enjoy two heated, fenced pools with new travertine decks, beach loungers for the exclusive use of owners and their guests, beachside Tiki Hut, gas grills, shuffleboard, canoe/kayak storage, and a beautifully soon to be remodeled clubhouse and Tower Lounge—the latter of which is reserved for the exclusive use of tower residents outside community events, and conveniently located on your floor. You’re also just an elevator ride down to the sparkling Gulf side pool and powder soft sand. Ideally positioned just moments from Siesta Key Village, you can leave your car behind and stroll to charming boutiques, live music, and an array of dining options. End each day with your toes in the sand or on your private balcony, savoring the tranquil rhythm of the waves and the company of friends as the sun melts into the horizon. This is more than a condo—it’s a lifestyle, a legacy of memories in the making, and a chance to secure your own piece of world class Gulf front paradise.
5830 MIDNIGHT PASS RD #51, SARASOTA, FL 34242
$549,00043 Days on yellowkey MLS ID: A4697244
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 728 Built: 1963 Tax: $3,460 (2025)Community: Jamaica RoyaleCondo
Taxes:$3,460
Remarks: Wonderful gulf side attached villa in an all ground level association, so no milestone inspections required. Fantastic opportunity to own your own slice of paradise. This 1 bed, 1 bath villa located at Jamaica Royale is ready for immediate occupancy. This beachfront complex is the perfect place to relax and unwind. Featuring 3 pools, beachfront lounge chairs, grills, shuffleboard, and other recreactional activites, there is something for everyone. Enjoy the pool views from your ground level unit with no stairs to navigate! With a weekly rental restriction, this unit could generate excellent rental income, especialy with current bookings already in the pipeline. Don't miss this great villa at this exceptional price. Schedule your showing today.
3508 LA PALOMA AVE, SARASOTA, FL 34242
$2,200,000127 Days on yellowkey MLS ID: A4686192
REDUCED by $50,000 (2.2%) on 06/22/2026
Bed: 5 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3195 Built: 2004 Tax: $24,862 (2025)Community: Siesta Rev OfSpa: NoSingle Family
Taxes:$24,862
Remarks: Price Reduced! Spacious island living, strong weekly rental income, and a prime north Siesta Key location come together in this beautifully maintained 5-bedroom, 3-bath furnished home just steps from beach access No. 1 at Shell Road on Big Pass. Built above base flood elevation of 11 feet, this property offers a valuable advantage on Siesta Key, along with the comfort, privacy, and usability today’s buyers are looking for. Fully gated and walled, the home sits on a generous lot surrounded by lush tropical landscaping, with an oversized 3-car garage and large paver driveway providing ample space for vehicles, beach gear, and a golf cart. Inside, the home offers large, open living spaces ideal for gathering and entertaining, featuring 12-foot ceilings, crown molding, arched openings, travertine flooring, and a spacious living room with gas fireplace. The kitchen includes stainless steel appliances, oak cabinetry, a breakfast nook overlooking the backyard oasis, and easy flow to the separate dining area and main living spaces. French doors open to a large terrace overlooking the tropical backyard, while an additional side terrace offers a private place to relax. The main-floor primary suite is a standout, offering direct terrace access, an oversized bedroom, two walk-in closets, and a luxurious en-suite bath with dual vanities, soaking tub, walk-in shower, and floor-to-ceiling travertine. Two additional bedrooms and a full bath are also located on the first floor, creating a functional and flexible layout. Upstairs, two generous guest bedrooms, a full bath, and a wet bar with beverage fridge provide an ideal retreat for visitors, with one bedroom opening to a private terrace overlooking the backyard. Designed for indoor-outdoor island living, the backyard is a true tropical oasis with mature landscaping, a heated saltwater pool with fountain, paver deck, large turf area, outdoor shower, and an exceptional tiki hut bar and outdoor kitchen complete with a built-in gas grill, two bar fridges, and porcelain countertops. An additional fenced side yard offers extra space for pets or outdoor enjoyment. Offered turn-key furnished, with a five-bedroom layout, generous lot size, multiple terraces, abundant storage, central vacuum, and expected 2026 rental income of $190,000. This home is an outstanding opportunity for those seeking a private Siesta Key retreat, income-producing investment, or both. Ideally located near world-renowned Siesta Key Beach and just a short drive to downtown Sarasota’s restaurants, shopping, and cultural attractions, this property offers the best of island living with convenience, comfort, and flexibility.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Robert Ruiz (941-544-3299)
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