Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
222 MORNINGSIDE DR, SARASOTA, FL 34236
$7,500,000142 Days on yellowkey MLS ID: A4675254
REDUCED by $495,000 (6.2%) on 05/25/2026
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 4284 Built: 2015Monthly Fee: $42 Tax: $34,055 (2025)Community: Lido CSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$34,055
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Booker Middle
Remarks: An extraordinary expression of modern waterfront living, this custom-designed Sarasota residence seamlessly blends architectural distinction, refined interiors and a tranquil Bayou setting flowing directly into the Gulf of Mexico, creating a home that is visually striking and effortlessly livable. Thoughtfully conceived by the owners, this exceptional five-bedroom, three full-bath and one half-bath waterfront residence is on approximately .37 acres and was designed to honor its surroundings while embracing contemporary form, function and natural light. Offering 4,284 square feet under air and 6,416 total square feet, the home makes a striking yet calming first impression. A circular brick-paver driveway, decorative architectural elements, trellises accents, curated landscaping, and subtle exterior lighting establish a refined sense of arrival and architectural presence. Inside, a dramatic open-concept floor plan unfolds with intention and volume. The great room features ceilings approaching 20 feet, custom wire railings and expansive glass frame serene water views from every room. Natural materials, most notably warm cedar accents carried seamlessly from interior to exterior, create a cohesive modern design language. Beechwood flooring, refined finishes, automatic solar window treatments, imported European light fixtures, and integrated LED lighting enhance comfort and contemporary appeal. The gourmet kitchen is designed for everyday living and entertaining, featuring Porcelanosa Design cabinetry, a side-by-side paneled Sub-Zero refrigerator, Asko dishwasher, Wolf built-ins including wall oven, warming drawer, microwave, a U-Line under-counter wine cooler, illuminated onyx island, quartz countertops, seamless under-cabinet lighting and a walk-in pantry. A new Whirlpool top-load washer complements the Whirlpool Cabrio Platinum dryer, completing the home’s functional amenities. The residence offers exceptional flexibility with two private primary suites on the main and upper levels, each providing direct terrace access and tranquil water views. Spa-inspired baths, one features a steam shower and walk-in closets, creating serene retreats. Additional guest suites, office, a waterfront gym or flexible living space, and these multiple en-suite accommodations support a variety of lifestyles. Outdoor living is equally compelling. A saltwater infinity-edge pool with spa and planter waterfall feature anchors the waterfront setting, complemented by covered and enclosable lanais with automatic window and terrace screens. Existing posts for the hammock overlook the Bayou. The outdoor pavilion provides space for an outdoor kitchen, with room to add a built-in grill, ice maker or under-counter refrigerator with existing gas hookup and water supply. A private illuminated dock provides direct Bayou access leading into the Gulf of Mexico, enhancing the home’s connection to nature and offering multiple gathering spaces ideal for entertaining and cherished memories. Modern construction, impact-rated openings and integrated smart-home technology contribute to peace of mind and long-term value. In one of Sarasota’s desirable waterfront neighborhoods, with optional deeded Lido Shores beach access and proximity to downtown Sarasota, St. Armands Circle and Longboat Key, this residence offers privacy, elevation, serenity and refined expression of luxury coastal living, designed to be admired and lived in.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Moriah Taliaferro (941-504-9910)
3310 MINEOLA DR, SARASOTA, FL 34239
$665,000149 Days on yellowkey MLS ID: A4676490
0 Days Off yellowkey (back on 5/25/2026)
REDUCED by $10,000 (1.5%) on 05/08/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1818 Built: 1958Monthly Fee: $17 Tax: $3,383 (2025)Community: South GateSpa: YesSingle Family
Taxes:$3,383
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. How will you keep cool this Summer? With a pool of course! Waterfront pool home for those who love nature and will enjoy overlooking the Jaffa Canal. Manatees will visit your backyard when dredging is complete. Connected to Phillippi Creek, you will have access out to Little Sarasota Bay, the Intercoastal Waterway & Gulf Waters! County dredging project underway of creek and canal behind this home! Discover Paradise in this home built on 1/3 acre on an island & private cul-de-sac. It is ideal for a full-time homestead or seasonal residence, located in the highly desirable South Gate neighborhood & Southside Elementary school district! Relax in your own outdoor oasis with 31'x14' & 8’ deep with aerating fountains and a 7’x7’ built in heated Spa! The open floor plan of this home makes it flexible for your needs with 2 larger bedrooms and 3rd used as a den with built-ins in closet. Master suite has custom walk-in closet and Travertine updated bath, glass-enclosed shower, large vanity & cabinet w/pull-outs. The French doors open to beautiful palm trees giving privacy to the outdoor spa area! The flex/family room also opens up to the 59’x24’ screened pool area, covered lanai and pool deck! Use the flex room as a den, art studio/craft room, informal dining & family room. Entry hall closet also has built-in shelving/drawers. French doors can be open or closed to afford privacy to the great room and adjacent updated kitchen with granite counters, wood cabinets & stainless steel appliances *New Refrigerator 2025 *New Air Conditioner 2025 *Shingle Roof 2019 *Sewer Connect 2015 **Pool added in 1999 ~ Re-marcited in 2013, Pool/Spa Heat pump 2015, Pool Motor 2019 *Two Water heaters (on each end of home age 3 & 5) *Many additional updates since original build include electrical switches/outlets, 5" baseboards, wood casing detail, doors, hardware, windows & underground utilities *Well for irrigation of lush tropical, low-maintenance Florida friendly landscaped yard on this 13,000 sq. ft. lot. with seawall. The 460 sq. ft. 2 car garage has built in work bench & additional laundry room w/storage closet. Located just minutes to Sarasota Memorial Hospital, Downtown Sarasota, Shopping, Southside Village, St. Armand's Circle, World-famous Siesta Key and Lido Beaches! *HOA is optional only $200/year ~ Schedule your visit today!
Listing is courtesy of: LPT REALTY LLC (813-359-8990)
Listing Agent: Solveiga Spalvins (941-320-6860)
137 AVENIDA MESSINA #1, SARASOTA, FL 34242
$600,000202 Days on yellowkey MLS ID: A4671658
REDUCED by $20,000 (3.2%) on 05/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 900 Built: 1966 Tax: $6,247 (2024)Community: Villa NavarraCondo
Taxes:$6,247
Elementary School: Phillippi Shores Elementary
Tax Year: 2024
Remarks: Centrally located and fully furnished! Located within the boutique condominium community of Villa Navarra on Siesta Key, this fully updated, turnkey-furnished ground-floor residence offers an exceptional blend of quality, comfort, and convenience. The property is ideally situated one block from Siesta Key Village and approximately two blocks from Siesta Beach, providing easy access to the island’s most popular destinations. Ideal for full time, snow birds or people looking to lease this condo out to renter's for the two month minimum. The residence features two bedrooms and two full bathrooms arranged in an open, functional layout. The spacious living and dining areas flow seamlessly into a thoughtfully renovated kitchen appointed with solid-surface countertops, modern cabinetry, and stainless-steel appliances. Finishes and flooring throughout the home have been carefully selected to create a clean, contemporary aesthetic that complements its coastal setting. The primary suite includes an en-suite bath and generous closet space, while the guest bedroom is conveniently located near the second full bath. The ground-floor design allows direct access to the assigned parking space for added ease. With extensive updates and attention to detail, this residence is move-in ready and designed for practical, comfortable living. Villa Navarra is a well-maintained, low maintenance community of just sixteen units surrounded by tropical landscaping and a relaxed island atmosphere. Residents enjoy convenient access to the free Siesta Key trolley and can easily walk to Siesta Key Village, offering a wide variety of local dining, shopping, and entertainment options. The renowned quartz sands and turquoise waters of Siesta Beach are only a short stroll away. This property is well-suited for a full-time residence, seasonal getaway, or long-term rental investment. Its location, quality, and turnkey condition make it a rare opportunity to enjoy the Siesta Key lifestyle within a private and beautifully maintained setting.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jeffrey Bray, Pllc (941-718-1213)
2576 HUNTINGTON AVE, SARASOTA, FL 34232
$359,90020 Days on yellowkey MLS ID: A4693286
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1296 Built: 1980 Tax: $3,693 (2025)Community: Orange Grove ParkSpa: NoSingle Family
Taxes:$3,693
Elementary School: Wilkinson Elementary
Remarks: Under contract-accepting backup offers. Welcome to this beautiful Sarasota gem nestled on a quiet, tree-lined street in the desirable Orange Grove Park community. Offering 2 bedrooms, 2 full bathrooms, and 1,296 square feet of thoughtfully designed living space, this charming single-story home blends timeless character with modern comfort and Florida lifestyle appeal. Step inside to discover an inviting open floor plan featuring sleek tile flooring, a soft contemporary color palette, abundant natural light, and stylish upgrades throughout. The spacious living and dining areas flow seamlessly into the well-appointed kitchen, creating the perfect space for entertaining or everyday living. French doors lead to a bright glass-enclosed Florida room, ideal for a home office, reading nook, fitness space, or year-round relaxation. The private primary suite offers a peaceful retreat complete with an updated en suite bath featuring a granite-topped vanity and vessel sink. Outside, enjoy your own tropical oasis with an elevated deck, tiled patio, privacy fencing, and lush mature landscaping that creates a serene backyard setting perfect for morning coffee or evening gatherings. Enjoy peace of mind with move-in ready condition, low-maintenance living, and the added freedom of no HOA restrictions. Perfectly located just minutes from Downtown Sarasota, UTC shopping and dining, SRQ Airport, world renowned Gulf beaches including Siesta Key and Lido Key, parks, golf courses, and everyday conveniences. With easy access to I-75 and nearby arts, dining, and entertainment, this home offers the ideal combination of charm, location, and Florida lifestyle living. Don’t miss this opportunity to own a beautifully maintained Sarasota home in a prime central location!
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Breanne Frank (941-299-3092)
819 PARADISE WAY, SARASOTA, FL 34242
$2,295,00019 Days on yellowkey MLS ID: A4693282
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2505 Built: 1996Monthly Fee: $17 Tax: $18,581 (2025)Community: Siesta IslesSpa: YesSingle Family
Taxes:$18,581
Remarks: Set on a beautiful street on Siesta Key near the world-renowned white quartz sands of Siesta Beach and the shops and dining of Siesta Key Village, this exceptional waterfront residence captures the essence of relaxed coastal living with deep boating water along the Grand Canal and direct access to Sarasota Bay and the Intracoastal Waterway. Beautifully landscaped on a nearly 14,000-square-foot homesite, the property welcomes with a circular paver drive, tile roof and timeless curb appeal. Thoughtfully above base flood elevation, the residence blends the beauty of waterfront living with the added comfort of elevated construction. Inside, volume ceilings and an open floor plan create a light-filled atmosphere designed for comfortable everyday living and effortless entertaining. Rich Le Château engineered wood flooring flows throughout the living spaces, complemented by refined finishes and thoughtfully selected details. The beautifully designed island kitchen is elegant and functional, featuring fine stone countertops, a gas cooktop, stainless steel appliances, custom cabinetry and a generous workspace for gathering and entertaining. The spacious floor plan offers three bedrooms, two-and-a-half baths, a private office, formal and casual living and dining areas, a split-bedroom layout and an interior laundry room. The primary suite is complemented by a spacious ensuite bath with dual vanities, a soaking tub and a separate walk-in shower, creating a private retreat within the home. Walls of glass open to an expansive 35-by-35-foot screened lanai with a freeform pool and spa overlooking the waterway, creating a seamless transition between indoor and outdoor living. A magnificent up-lit oak tree brings warmth and character to the backyard, enhancing the property’s tranquil setting. For boating enthusiasts, the Grand Canal provides easy access to Sarasota Bay and the Intracoastal Waterway with only one bridge to the bay and a mean tide clearance of approximately 13 to 14 feet. The seawall, dock and pilings for a future boat lift accommodating up to 14,000 pounds were all installed in 2020, creating an exceptional setting for enjoying life on the water. A rare opportunity to experience refined waterfront living in one of Siesta Key’s desirable locations.
Listing Agent: Judie Berger (941-928-3424)
6285 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$643,000391 Days on yellowkey MLS ID: A4651246
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1981 Tax: $6,349 (2024)Community: Excelsior Beach To Bay 5Spa: YesCondo
Taxes:$6,349
Remarks: Tremendous value for this 4th floor condo for sale at the Excelsior Beach to Bay Complex! Coveted for its soaring ceilings and the opportunity to add a bona fide 3rd bedroom, you can redesign this bayside penthouse into a luxurious home/home away from home. Take your time as there have been updates, it's in great condition and quite lovely as is. This particular unit faces south and is filled with lots of natural light plus the added benefit of clerestory windows. AC and water heater replaced in 2025. A pre-listing home inspection was conducted for your peace of mind and is available for review. There have been some compelling upgrades over the years including granite countertops, stainless appliances flooring, carpeting and so forth. The condo has not only been owned by the same family since construction if is also smoke free, pet free, never rented, and has been extremely well maintained. The screened in lanai overlooks the grounds however could be enclosed if you like. Each condo comes with assigned underbuilding parking as well as an additional parking for one other car under the carports. There is also a locked storage locker for your toys and seasonals. Absolutely the best value and opportunity at the Excelsior and perhaps on Siesta Key itself. The Excelsior is rich with amenities: Two Large Heated Swimming Pools, Poolside Restrooms / Hot Water Showers, Two Hot tubs, Tennis Courts, Pickle Ball Courts, Fitness Center, Gulf side Sun Deck, Beach Lounge Chairs, Outdoor Grills, Intercoastal Fishing Pier, Community Room and monthly community events, Library, and catering kitchen. Walk to Shopping, Dining, Bike & Boat Rentals This ideal location has direct and deeded beach access to Siesta Beach, renowned for its quartz sand known for staying cool in the summer and feeling like talcum underfoot. Easy on and off the key access at the south Stickney Point Bridge. The increasingly popular Gulf Gate neighborhood is just over the bridge offering a wide variety of eclectic restaurants, grocers, pubs, and shops. A remarkable opportunity with these features and at this price which doesn't come around very often.
Listing is courtesy of: EXIT KING REALTY (941-497-6060)
Listing Agent: Joan Winters (941-536-1714)
915 SEASIDE DR #312, Weeks 16-17, SARASOTA, FL 34242
$48,00031 Days on yellowkey MLS ID: A4692319
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1750 Built: 2009 Tax: $321 (2026)Community: Siesta Key Beach ResidencesSpa: YesCondo
Taxes:$321
Tax Year: 2026
Remarks: Fractional Ownership. Experience luxury beachfront living with this Winter Fractional Package offering a 1/16th share of ownership at The Residences on Siesta Key Beach. This is a rare opportunity to own a piece of paradise on one of America’s top-rated beaches while enjoying the comfort, convenience, and services of a luxury resort. This expansive residence features a primary suite, junior primary suite, and guest bedroom, along with beautifully updated custom furnishings valued at more than $150,000. The fully equipped kitchen includes premium Wolf, Sub-Zero, and Fisher & Paykel appliances, complemented by imported linens and thoughtful details throughout. Owners enjoy legendary Hyatt Vacation Club hospitality services, including daily complimentary continental breakfast, beach service, recreation and front desk staff, assistance with local activities, valet parking, and 24-hour security. Enjoy everything you would expect from a luxury Siesta Key beachfront condominium with resort-style amenities and services, all at a fraction of the cost.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Kelly Mooney (941-587-8430)
139 S WASHINGTON DR, SARASOTA, FL 34236
$14,950,000296 Days on yellowkey MLS ID: A4661401
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 7817 Built: 1936 Tax: $158,866 (2025)Community: Saint Armands Div John Ringling EstatesSpa: YesSingle Family
Taxes:$158,866
Remarks: Timeless Elegance, Effortless Living where HISTORY Meets MODERN LUXURY @ "Casa del Carnevale," an exquisite waterfront estate, situated in the prestigious St. Armands Key, the neighborhood of John Ringling Estates. This home seamlessly blends history with modern luxury, offering views of the Sarasota Waterway and Bay with a historic designation. Casa del Carnevale presents a rare opportunity to own an esteemed historical property. Offered for only the fifth time in its storied history, this exceptional estate combines Old World architectural charm with contemporary opulence. The home underwent an extensive renovation, with meticulous attention to detail and craftsmanship, utilizing top-tier materials and artisanship. Expanded from 4,000 to nearly 10,000 sq. ft. under roof, and featuring over 7,800 sq. f.t of air-conditioned space, Casa del Carnevale preserves its original charm while offering a reimagined layout that exceeds modern luxury standards. Set on three sprawling lots, 30,000+ square feet, the estate boasts 171 feet of waterfrontage, a private dock lift, a floating lift for jet skis and kayaks, and breathtaking views of Sarasota Waterway. The lush, meticulously designed tropical landscaping creates a private oasis that feels like you are walking in Selby Gardens on St. Armands. The residence includes five bedrooms and six and a half baths across two spacious levels with an elevator. Multiple terraces provide perfect outdoor retreats and entertaining areas, all complemented by stunning garden water vistas, a central courtyard, and an elegant 65' saltwater pool and spa with arched spraying fountains and iridescent glass tiles. Other luxury features include a three-car garage, elevator, nanny’s quarters, walk-in wine room, billiards room, office, and custom impact-glass arched windows designed to maximize unobstructed views. The chef’s kitchen boasts premium finishes, top-of-the-line appliances, a 5-Star La Cornue range and hood from France, featuring gas or electric ovens (kitchen art). Sub-Zero refrigerators, a Bosch dishwasher, a Miele microwave, a Miele built-in coffee machine, a stand-alone beverage refrigerator, and a stand-alone ice maker. Throughout the home, exposed beams, warm wood tones, natural stone, custom ironwork, Pecky Cypress wood throughout, and curated artwork create an inviting, sophisticated atmosphere. Offering furniture (negotiable under separate contract), and instant enjoyment to create everlasting memories, Casa del Carnevale is a rare and exquisite blend of history, elegance, and modern comfort on one of Sarasota’s most coveted waterfront estates. EASY TO SHOW. CASA DEL CARNEVALE IS A MUST-SEE IN PERSON TO FULLY APPRECIATE.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
111 S PINEAPPLE AVE #1204, SARASOTA, FL 34236
$2,950,000300 Days on yellowkey MLS ID: A4660919
2 Days Off yellowkey (back on 5/25/2026)
Bed: 3 Bath: 3.5 Gar: 4 Liv Area Sq Ft: 2845 Built: 2019 Tax: $26,938 (2024)Community: Mark SarasotaSpa: YesCondo
Taxes:$26,938
Remarks: Rare penthouse offering at Mark Sarasota. 111 S Pineapple Ave. #1204 is a one-of-a-kind 12th-floor residence and the largest home in the building, offering 2,845 square feet under air and over 3,600 square feet of total living space including a spacious wraparound covered terrace with uninterrupted views of Sarasota Bay. From the moment you go inside, you’re greeted by 11-foot ceilings, double 8-foot entry doors, and expansive 10-foot impact-rated sliding glass doors that blur the line between indoors and out. Gleaming 24-inch white polished porcelain tile floors run throughout the open-concept interior, where a thoughtfully designed layout integrates the living, dining, and family spaces with a chef-caliber kitchen—complete with high-gloss European cabinetry, quartz countertops, and a suite of premium Jenn-Air stainless steel appliances including a 42-inch built-in refrigerator, convection wall oven, and 36-inch induction cooktop. The primary suite is a private oasis, offering panoramic views, dual walk-in closets by California Closets, and a spa-inspired en-suite bath with double vanities, an oversized walk-in shower, deep soaking tub and sleek Grohe fixtures. Two generous guest suites, each with private baths, custom closets and blackout shades, provide comfort and privacy for visitors or family. Additional interior highlights include a convenient and spacious family room/den, automated roller shades throughout with blackout shades in all bedrooms, a full laundry room with custom cabinetry and Whirlpool HE washer and dryer, water filtration and softener systems for the entire residence, and four deeded garage parking spaces plus a same-floor oversized private storage unit. The wraparound covered terrace is an entertainer’s dream with commanding views of the water and city skyline. Enjoy alfresco dining at the built-in outdoor kitchen, equipped with an electric grill, under-counter refrigerator, stone countertops, and durable exterior cabinetry. Residents of The Mark enjoy exceptional lifestyle amenities including 24-hour concierge service, a resort-style heated saltwater pool and spa, state-of-the-art fitness center with a dedicated spin room, a club room with catering kitchen, fireplace and billiards, as well as outdoor lounging areas with fire pits, grills, and dining spaces—all just steps from Whole Foods, Bayfront Park, shopping, dining, galleries and Sarasota’s renowned cultural venues. This rare penthouse opportunity places you in the heart of downtown Sarasota’s most desirable address, where convenience, comfort and coastal elegance converge.
Listing Agent: Mike Warm, Llc (941-525-2740)
5560 SHADOW LAWN DR, SARASOTA, FL 34242
$1,399,000497 Days on yellowkey MLS ID: A4636955
REDUCED by $100,000 (6.7%) on 05/25/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2124 Built: 1970Monthly Fee: $17 Tax: $8,052 (2025)Community: Siesta IslesSpa: NoSingle Family
Taxes:$8,052
Remarks: One of the lowest priced homes on Siesta Key's deep boating water and only 3 blocks to the white quartz sand and aqua Gulf waters! An inviting opportunity to enjoy relaxed waterfront living on Siesta Key, this well-maintained residence is ideally positioned just minutes from the powdery white sands of world-famous Siesta Beach and the turquoise waters of the Gulf. Set on an oversized 14,000-square-foot corner lot, this four-bedroom, three-bath home blends comfortable coastal living with everyday functionality in a highly desirable island setting. Designed for effortless entertaining and easy living, the open-concept floor plan centers on a spacious island kitchen with generous seating, a breakfast bar, and abundant workspace, flowing seamlessly into the dining and living areas for gatherings both large and small. A thoughtful split-bedroom layout offers privacy for owners and guests alike. The primary suite enjoys peaceful views of the pool and canal, while a secondary bath doubles conveniently as a pool bath—ideal for indoor-outdoor living. Step outside to the covered, screened lanai and unwind beside the sparkling pool, framed by tranquil water views and gentle coastal breezes. Tucked along a quiet harbor just off the Grand Canal, the setting is ideal for kayaking, paddleboarding, or boating, with frequent sightings of manatees and coastal birds adding to the natural charm. Evenings bring glowing “mango sunsets” nearby, while mornings begin with soft sunrises reflected on the water. Additional highlights include an oversized two-car garage and a concrete tile roof. Ideally located near the shops, dining, and energy of Siesta Village—and just 15 minutes from downtown Sarasota’s vibrant arts and cultural scene—this home presents a compelling opportunity to enjoy the best of island living, whether as a full-time residence or a serene coastal retreat.
Listing is courtesy of: PREMIER SOTHEBYS INTL REALTY (941-364-4000)
113 WHISPERING SANDS DR #V47, SARASOTA, FL 34242
$615,00097 Days on yellowkey MLS ID: A4683156
0 Days Off yellowkey (back on 5/24/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1344 Built: 1968Monthly Fee: $1,351 Tax: $5,993 (2025)Community: Whispering Sands Sec 5Villa
Taxes:$5,993
Remarks: One or more photo(s) has been virtually staged. NEW PRICE! Discover the ease of island living in this newly REMODELED 3BR/2BA villa with garage in the premier GULF FRONT property of Whispering Sands! As a rare freestanding villa, this residence offers the privacy of no shared walls and lives like a single family residence. Every detail has been thoughtfully curated, from the reimagined open galley kitchen with its sophisticated soft grey tones and granite countertops, stainless appliances, and soft close cabinetry and drawers – flowing seamlessly into the main living areas – to the beautifully updated bathrooms and elegant tile flooring. Textured ceilings and recessed lighting create a warm, contemporary ambience. The small private patio invites relaxed al fresco dining, while the rare 1-car garage—complete with an epoxy floor, full sized W/D hookup, and its own A/C system—adds exceptional convenience and storage. Behind the scenes, extensive upgrades provide total peace of mind. All windows and sliders are 2022 hurricane impact rated. The plumbing supply and drain lines in this villa were updated from cast iron to PVC in 2022. Further enhancing the home’s value are a NEW concrete tile villa roof and a 2023/2024 garage roof. 2022 HVAC system. Ideally located just steps from the clubhouse, 2 heated pools, and 800’ of Whispering Sands’ own PRIVATE beach on the Gulf, this residence also enjoys a prime setting next to the dining, shopping, and vibrant atmosphere of Siesta Key Village. Imagine starting your day with a morning dip in the Gulf followed by a peaceful stroll along the private shoreline. Spend the afternoon unwinding poolside or swimming invigorating laps in one of two heated pools. Stroll to the Village for a delicious, cozy supper and end the day gathered with friends as the Gulf sky ignites in breathtaking sunset color. Whether you’re seeking a full-time residence or the perfect coastal retreat, this move-in-ready villa offers the best of maintenance free, resort style living in an exceptional island location.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
1751 HAWTHORNE ST, SARASOTA, FL 34239
$2,495,00053 Days on yellowkey MLS ID: A4689684
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3875 Built: 2006 Tax: $33,343 (2025)Community: Hudson BayouSpa: YesSingle Family
Taxes:$33,343
Remarks: Step into a home that feels more like a private gallery and retreat than a traditional residence—where modern design, light, and location come together in a way that’s nearly impossible to replicate in Sarasota. Located just one block from Southside Village and minutes to downtown, this West of Trail architectural residence is designed for the cosmopolitan buyer—someone who values design, art, walkability, and a lifestyle that blends indoor and outdoor living seamlessly. From the moment you enter, you’re greeted by a dramatic two-story great room with soaring ceilings, polished concrete floors, and a striking mid-century modern fireplace. A wall of glass draws your eye straight through to the sun-drenched, Palm Springs-inspired pool and lush tropical backdrop—creating that immediate “this is different” feeling. The scale and clean lines offer the perfect canvas for an art collector, with expansive walls that invite statement pieces. The kitchen is both functional and beautifully integrated—designed for someone who entertains without wanting to be separated from the experience. Custom cabinetry, a professional-grade 48" Jenn-Air gas range, double ovens, and a wet bar all open directly to the living and dining spaces, including a character-rich built-in banquet booth that feels both classic and intentional. On the main level, a guest suite with large sliders opens to a covered, screened lanai—ideal for outdoor dining or evening lounging without interruption. There’s also a dedicated office for the not-quite-retired, a bright and airy laundry room, and thoughtful storage throughout. Upstairs, the home continues to surprise. A lofted lounge creates separation for guests or quiet moments, while a spacious ensuite bedroom provides comfort and privacy. Then, a true conversation piece—the observatory, accessed via a winding staircase—offers a unique escape that feels both playful and sophisticated. The primary suite is expansive and light-filled, with generous closet space, dressing areas, and a bathroom that carries through the home’s mid-century modern aesthetic. Outdoors, the experience is equally refined. Low-maintenance designer rock beds are complemented by mature palms and lush landscaping, framing a private resort-style pool and spa. A detached 400 sq. ft. studio/guest house adds flexibility—perfect as an art studio, fitness space, guest suite, or private office with its own entrance. The garage is oversized with a two-car door but space for much more—cars, e-bikes, paddleboards, even a golf cart—supporting an active, coastal lifestyle. This is not a home for everyone—and that’s exactly the point. It’s for the buyer who has outgrown the ordinary, who appreciates architecture and design, who wants to be close to everything yet live in one of Sarasota’s most desirable residential neighborhoods. Because the reality is—homes like this rarely come available. And when they do, they don’t last. If you’ve been waiting for something that actually feels different… this is it.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Mark Coppens (941-444-0436)
223 GOLDEN GATE PT #302, SARASOTA, FL 34236
$2,950,000110 Days on yellowkey MLS ID: A4682563
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2400 Built: 2025Monthly Fee: $2,390Community: Peninsula SarasotaSpa: YesCondo
Taxes:$0
Middle School: Sarasota Middle
Remarks: Newly completed, Peninsula Sarasota is ideally positioned in the coveted Golden Gate Point neighborhood, offering a peaceful residential retreat just moments from the vibrancy of downtown Sarasota. Designed by Blu Interiors, each residence showcases contemporary modern elegance with calming, sophisticated palettes, soaring ceilings, and expansive wraparound terraces that seamlessly blend indoor and outdoor living. Every element reflects a thoughtful commitment to refined luxury. State-of-the-art kitchens feature sleek European cabinetry, gas cooktops, and quartz countertops, complemented by premium Wolf and Sub-Zero appliances. Additional highlights include hardwood flooring throughout, floor-to-ceiling windows that flood the home with natural light, and a private terrace equipped with a gas grill—perfect for effortless entertaining. The spacious owner’s retreat serves as a true sanctuary, complete with a generous walk-in closet, dual vanities, a soaking tub, and an oversized walk-in shower for spa-like relaxation. Residents enjoy on-site concierge services and secure, access-controlled underground parking for two vehicles, including an EV charging station. A private foyer and dedicated elevator provide direct access to exceptional amenities such as a resort-style pool and state-of-the-art fitness center, while the elegant owner’s club room offers private wine storage for each residence. The communal rooftop terrace sets the stage for unforgettable gatherings, boasting sweeping panoramic and sunset views. Peninsula Sarasota delivers a truly elevated lifestyle within a lush, tropical setting—just minutes from Sarasota’s celebrated arts, culture, dining, and award-winning beaches. A rare opportunity to experience sophisticated coastal living. Schedule your tour today!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Georgia Salaverri (954-661-8968)
3512 CAMINO REAL, SARASOTA, FL 34239
$2,650,000208 Days on yellowkey MLS ID: A4671290
REDUCED by $95,000 (3.5%) on 04/21/2026
Bed: 5 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3810 Built: 2025 Tax: $6,583 (2025)Community: GranadaSpa: YesSingle Family
Taxes:$6,583
Remarks: 3512 Camino Real represents a rare opportunity to acquire a newly constructed luxury residence strategically positioned for high-performing short-term rental income in one of Sarasota’s most supply-constrained residential corridors. Located inside the City of Sarasota and approximately 10 minutes to Siesta Key Beach, Siesta Key Village, and Downtown Sarasota, this property is purpose-built to operate under a weekly rental model that aligns with current city regulations while attracting higher-quality, longer-stay guests. Unlike many coastal investment properties that rely on nightly rental volatility or regulatory gray areas, this home offers a compliant, predictable income profile paired with strong long-term appreciation fundamentals. Completed in 2025 by award-winning Heritage Builders, the British West Indies–inspired residence spans 3,810 square feet on an oversized .27-acre corner double lot, offering 5 bedrooms, 4.5 bathrooms, a dedicated office, a game room, and a 3-car garage. The layout comfortably sleeps up to 12 guests, supporting premium weekly rates and strong demand across multiple seasons. The home’s interior and exterior amenities are intentionally aligned with today’s luxury short-term rental market: a private heated resort-style pool and spa, expansive covered lanai with outdoor kitchen, open-concept living areas, high ceilings, impact-rated windows, concrete block construction, and elevated hurricane standards. These features enhance guest experience while also reducing operational risk, insurance exposure, and long-term maintenance costs—key considerations for investor underwriting. From an operational standpoint, a weekly rental strategy delivers meaningful advantages: fewer guest turnovers, lower housekeeping and wear-and-tear costs, improved booking stability, and reduced party risk. The surrounding Granada neighborhood further strengthens the investment thesis, offering oak-lined sidewalks, walkable parks, proximity to boating access, Southside Village dining, and Downtown Sarasota’s cultural and marina district—all while remaining above the flood zone, a critical differentiator for long-term ownership and asset resilience. Beyond income potential, 3512 Camino Real offers multiple exit strategies. Its new-construction pedigree, desirable residential setting, and luxury finish level support future resale to primary residents, second-home buyers, or continued investor ownership. Limited supply of large, newly built homes with pools inside Sarasota city limits underpins long-term value appreciation and broad buyer appeal across market cycles. A comprehensive Short-Term Rental Investor Report, including projected revenue, operating assumptions, conservative and upside scenarios, and long-term investment analysis, is available upon request and is attached in the MLS for qualified buyers.
1055 W PEPPERTREE DR #102AA, SARASOTA, FL 34242
$850,000141 Days on yellowkey MLS ID: A4677695
1 Days Off yellowkey (back on 5/23/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1163 Built: 1974 Tax: $4,365 (2025)Community: Peppertree Bay IvSpa: YesCondo
Taxes:$4,365
Remarks: Under contract-accepting backup offers. Rare opportunity to own one of the most resilient and desirable residences on Siesta Key! This 2-bedroom, 2-bath condominium offers 1,163 square feet of living space (1,462 gross square feet) and is ideally positioned on the west side of the building on an elevated first floor, approximately 15 feet above sea level. It is also the closest high-rise condominium to the beach, offering exceptional proximity to the Gulf. One of only six residences in the building with an expansive deck, this sought-after middle-unit location provides a truly rare outdoor living experience. The oversized deck offers ample space for dining, entertaining, or simply relaxing while enjoying coastal breezes and sunsets. The residence has demonstrated remarkable storm resilience, sustaining no damage through three major hurricanes. This is attributed to its elevated positioning, protected west-side exposure, and six hurricane-rated doors installed in 2021. Recent interior upgrades enhance both style and comfort, including luxury vinyl flooring and freshly painted walls completed in 2025. The refrigerator, washer, dryer, and garbage disposal were also replaced in 2025. A dedicated parking space conveys with the unit. Owned by the same family since 1976, the home reflects decades of pride of ownership and thoughtful care. The community features two pools and two clubhouses on both the Gulfside and Bayside, along with a Gulfside fitness center. A well-managed rental program offers flexibility for owners while preserving a relaxed residential atmosphere. Located in one of Florida’s most coveted coastal settings, this exceptional residence offers a rare blend of scarcity, storm resilience, expansive outdoor living, and resort-style amenities—making it an outstanding lifestyle choice and investment opportunity.
Listing is courtesy of: REALTY HUB (407-900-1001)
Listing Agent: Tanya Stutzman (941-504-8785)
4243 MIRIANA WAY, SARASOTA, FL 34233
$529,90088 Days on yellowkey MLS ID: A4685208
REDUCED by $10,000 (1.9%) on 05/22/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2149 Built: 2003Monthly Fee: $312 Tax: $4,049 (2025)Community: Villa RosaSingle Family
Taxes:$4,049
Elementary School: Ashton Elementary
Remarks: Welcome to this beautifully maintained 3-bedroom, 2-bathroom plus den home, located in the gated community of Villa Rosa — a hidden gem of maintenance-free single-family homes in the heart of Sarasota. Sitting high and dry in the desirable Flood Zone X (no flood insurance required), this residence is perfectly positioned on a serene lake with views of a lovely magnolia tree and fountain. The oversized screened patio—featuring all new screens and stainless steel screws (2025)—is ideal for relaxing, dining al fresco, or soaking up the sun with a great book. Enjoy complete peace of mind with a NEW tile roof (2022), NEW air conditioning system (December 2024), hurricane shutters throughout, and a hurricane-impact garage door. Additional upgrades include whole-house gutters with new gutter guards (2025), a brick paver driveway and walkway in classic herringbone design, landscape curbing, plantation shutters, custom Hunter Douglas blinds, and professionally installed surround sound for your AV equipment and entertainment needs. Step inside this one-owner, meticulously cared-for home with an open and thoughtfully designed floor plan—offering the open living concept you desire while maintaining the privacy everyone appreciates. A versatile den at the front of the home features French doors with custom blinds, wood flooring, and a charming bay window, making it an ideal home office, reading room, or bonus space. The two guest bedrooms and guest bath featuring a TOTO comfort height toilet are tucked away in their own private hallway and provide comfort for family or visitors. The primary suite is situated in its own wing, showcasing peaceful pond views, one walk-in closet plus a second spacious closet, and an ensuite bath with dual sink vanities, a large soaking tub, shower with grab bars, a private water closet, and an upgraded TOTO comfort-height toilet. At the heart of the home, the great room, with trey ceiling, kitchen with island and bar seating, and the eat-in dining area all open to the screened lanai overlooking the water—offering tranquil views from every angle. The kitchen boasts Silestone countertops, an abundance of cabinetry, a generous pantry, and a pocket door separating the kitchen and formal dining room. High ceilings, crown molding, extra closets, and abundant natural light flow throughout. The laundry room with pocket door and extra large closet includes a newer LG washer and dryer (2022) and the two-car garage is upgraded with high ceilings, built-in cabinetry, and an epoxy-surfaced floor. Living is easy within the gates of Villa Rosa, where lawn maintenance and cable TV are included and residents enjoy access to a heated community pool, spa, fitness and club room. You’ll love connecting with neighbors through the many community events. From your front door, take a leisurely stroll to Urfer Family Park’s scenic walking trails. This peaceful yet central location puts you close to shopping, hospitals, doctors’ offices, and only 8 miles from world-renowned Siesta Key Beach. Indulge in Sarasota’s vibrant arts and dining scene with the nearby ballet, opera, restaurants, and Saint Armands just minutes away. Perfect as a year-round residence or a seasonal retreat, this Villa Rosa home offers the best of Sarasota living—comfort, convenience, and community. Furnishings available on a separate contract
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Laura Way (941-321-6449)
2440 VALENCIA DR, SARASOTA, FL 34239
$559,00043 Days on yellowkey MLS ID: A4690679
REDUCED by $40,000 (6.7%) on 05/21/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1330 Built: 1956 Tax: $3,188 (2025)Community: South GateSpa: NoSingle Family
Taxes:$3,188
Remarks: Charming Sarasota home for sale with 2 bedrooms, 2 baths, over 1,300 square feet, a one-car garage, and a fully fenced backyard. Located in the highly sought-after Southside Elementary school district, this residence offers the perfect blend of charm, comfort, and convenience. Inside, beautiful terrazzo floors, integrated built-ins, and a light-filled Florida room create an inviting atmosphere with flexible space for relaxing, entertaining, or working from home. This home’s midcentury appeal and classic Florida style make it especially inviting. Ideally located near downtown Sarasota, Southside Village, Sarasota Memorial Hospital, restaurants, shopping, parks, and the beaches, this is an excellent opportunity for buyers seeking a primary residence, seasonal retreat, or investment property in Sarasota real estate, with its character, ease of living, and optimal location.
5740 MIDNIGHT PASS RD #403, SARASOTA, FL 34242
$1,950,00047 Days on yellowkey MLS ID: A4686166
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1449 Built: 1986 Tax: $12,418 (2025)Community: Gulf & Bay Club Ph 6Spa: YesCondo
Taxes:$12,418
Remarks: A rare and exceptional offering within Building F at Gulf & Bay Club on Siesta Key, Unit 403 presents a truly one-of-a-kind coastal retreat. Completely taken down to the studs and reimagined in 2023, this residence showcases a meticulous, high-end renovation where no detail was overlooked. From the moment you enter, you’re welcomed by a light-filled, open-concept design with sweeping direct Gulf views that immediately set the tone. The chef’s kitchen is the centerpiece of the home, anchored by a stunning 12-foot oversized island with seating for six. Featuring eco-friendly PaperStone countertops and backsplash, a full suite of premium Thermador appliances, and seamless custom finishes, the space is as functional as it is striking—all complemented by breathtaking water views as you cook and entertain. Offered turnkey furnished, the interiors are thoughtfully curated with pieces from Arhaus, Restoration Hardware, and other luxury brands, creating a cohesive and sophisticated aesthetic. The open layout flows effortlessly from kitchen to dining to living, enhanced by custom built-ins that provide both style and smart storage, including a paneled wine refrigerator. Wake up to the Gulf from your private primary suite, a serene retreat designed for both comfort and elegance. This space features a dedicated vanity area, custom walk-in closet, and a beautifully appointed en-suite bath, offering a spa-like experience within your own home. Additional highlights include engineered hardwood flooring throughout, hurricane-impact windows and sliders, solid-core doors, and extensive custom storage solutions—all contributing to the home’s elevated design and livability. This two-bedroom, two-bath residence is set within the highly sought-after Gulf & Bay Club, where residents enjoy an unmatched, resort-style lifestyle across 32 acres of lush, manicured grounds. Indulge in 800 feet of private, powdery white sand beach, three heated pools, tennis and pickleball courts, a state-of-the-art fitness center with yoga studio and saunas, and multiple clubhouses featuring lounges, billiards, and social spaces. Additional amenities include barbecue and picnic areas, freshwater lakes, and EV charging stations. Ideally located just moments from the dining, shopping, and vibrant energy of Siesta Key Village—including the iconic Sunday Drum Circle—this residence offers the perfect blend of privacy, luxury, and convenience. Unit 403 is more than a home—it’s a rare opportunity to experience the very best of Gulf-front living on Siesta Key.
Listing Agent: Drew Jacobsen (941-253-6309)
4504 CITATION LN #C, SARASOTA, FL 34233
$299,90068 Days on yellowkey MLS ID: A4686138
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1385 Built: 1991Monthly Fee: $650 Tax: $2,900 (2025)Community: Calumet At Centergate 1Villa
Taxes:$2,900
Remarks: LUXURY PLUS LIFESTYLE RETREAT VILLA - Beautiful interior finishes and positioned on a premium corner lot in an intimate maintenance-free enclave community of only 66 homes. This elegant yet warm and inviting villa offers 2 bedrooms plus a den, 2.5 baths, and an oversized 2-car garage with two new garage door openers (2024). The home is thoughtfully updated with new appliances (2025), new A/C (2024), plush carpeting (2023), new window screens (2024), and finished with deluxe window shades. The floor plan has spacious rooms and an abundance of storage closets and garage storage space as well. A vaulted, screened lanai creates seamless indoor-outdoor living, filled with natural light throughout the day, while a cozy fireplace in the living room adds warmth and charm — creating a true Florida sanctuary. The main level includes a private primary suite, a versatile office/den, and a convenient half bath. The beautifully designed slate-gray kitchen opens to the expansive dining and living areas, ideal for both everyday living and entertaining. Upstairs, a second bedroom with en suite bath and walk-in closet provides comfort and privacy for guests. Just steps away, enjoy the community’s heated pool overlooking a tranquil pond, a clubhouse with full kitchen, and a fitness room. Ideally located with easy access to I-75 and just minutes from shopping, dining, parks, The Legacy Trail, Home Depot, hospitals and award-winning Siesta Beach! The HOA COVERS ROOF MAINTENANCE AND EXTERIOR PAINTING, along with weekly landscaping services including mowing, edging, and trimming. It also includes hedge and tree trimming, irrigation and sprinkler systems, outdoor pest control, and leaf removal. Residents have access to the community center, which features a meeting room, kitchen, restrooms, fitness center, and pool, as well as private use of clubhouse facilities. ADDITIONAL SERVICES include pool maintenance, mailbox upkeep, street lighting, and maintenance of all common areas such as the lake, entrance, signage, community spaces, visitor parking, exterior walls, and landscaping. VERY EASY TO SHOW AS WELL!
Listing Agent: Kathryn Cooper, Pa (941-320-8075)
1685 LAUREL ST #3, SARASOTA, FL 34236
$849,500153 Days on yellowkey MLS ID: A4676566
REDUCED by $25,490 (2.9%) on 05/13/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1667 Built: 2005Monthly Fee: $850 Tax: $7,785 (2025)Community: The Villas On LaurelTownhouse
Taxes:$7,785
Remarks: One or more photo(s) has been virtually staged. Just one block from Burns Court and 2 more blocks to Main Street, this beautifully updated three-bedroom, three-bath townhome with loft offers a rare combination of privacy, sophistication, and truly walkable downtown living. Thoughtfully positioned within an intimate community of 9 units, this residence enjoys views of the pool and lush greenery through tall impact casement windows from nearly every room—creating a far more private and serene setting than typically found in downtown living. Spanning two thoughtfully designed levels, the home blends architectural character with modern comfort and functionality. Recent improvements include new luxury vinyl flooring, fresh interior and exterior paint, a new HVAC system, and a new roof, offering both style and peace of mind. The kitchen is designed for everyday ease and entertaining alike, featuring a gas range and complemented by the efficiency of a tankless water heater. The first floor features a private guest bedroom with a full bath just across the hall—ideal for visitors, a home office, or flexible living needs. Upstairs, the spacious primary suite and additional guest suite each offer ensuite baths, while the loft provides the perfect flex space for a media room, office, fitness area, or reading retreat. Located within a pet-friendly community, residents enjoy effortless access to acclaimed restaurants, boutiques, galleries, theaters, waterfront parks, marinas and directly adjacent to Laurel Community Park. The association has recently completed an extensive capital improvement program, significantly enhancing the long-term value and stability of the community while maintaining comparatively low HOA dues. Major completed projects include roof replacement, exterior painting, pool resurfacing with pebble quartz finish, asphalt paving, updated landscaping and irrigation systems, outdoor lighting improvements, garbage enclosure replacement, and continued preventative maintenance. A comprehensive property assessment completed in 2025 confirmed the property’s well-maintained condition and long-life asset profile, with most major systems recently renewed or significantly extended through capital investment. Additional conveniences include two dedicated parking spaces, access to a community storage room ideal for beach gear and bicycles, and shared outdoor space with room for grilling and entertaining. Elegant yet comfortable, private yet connected, this impeccably maintained residence captures the essence of refined downtown living in one of Sarasota’s most desirable neighborhoods, Historic Laurel Park.
Listing is courtesy of: MAPP REALTY & INVESTMENT CO (941-379-2448)
Listing Agent: Mandy Mapp (941-650-6009)
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