Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,595,00029 Days on yellowkey MLS ID: A4687301
REDUCED by $100,000 (1.8%) on 04/16/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$25,684
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Brookside Middle
Remarks: Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Samantha Callaway (630-865-3189)
332 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,595,00030 Days on yellowkey MLS ID: A4687188
Bed: 9 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 4055 Built: 2019 Tax: $26,520 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$26,520
Tax Year: 2025
Remarks: ~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautiful home boasts 8 bedrooms + an additional bonus room = 9, plus 8 bathrooms, including 6 en-suite retreats, perfectly suited for a large primary residence or a high-performing luxury vacation rental. Ideally located and just steps from premier dining, boutique shopping, & vibrant nightlife, and only a short stroll or bike ride to the world-renowned Siesta Key Beach. This property offers the ultimate blend of convenience with the feel of a resort-style escape. Upon entering take the stairs or the convenient elevator up to the main living space. Here you will find an open chef's kitchen, large island, a beverage bar, along with the spacious living room and dining area. There are 2 bedrooms also on this level. Multiple balconies showcase great views of the village, while the home’s prime location places you moments from everything Siesta Key has to offer. It has been thoughtfully designed with high-end designer finishes and furnishings, every detail for both comfort and entertaining. The bonus room on the 4th level leads out to a spiral staircase and then up to the rooftop deck where both village and GULF VIEWS create a great backdrop for stunning SIESTA SUNSETS. Back on the 1st level, walk out to the covered patio and enjoy your private outdoor oasis with lush landscaping and the tranquil heated pool & spa designed for both relaxation and entertainment. It features an oversized sun shelf, wraparound lounge ledge and in-water bar seating. Whether you're hosting family and friends, a large group getaway or seeking a luxury investment property, this extraordinary beach house delivers unmatched living spaces throughout. It also comes beautifully turnkey furnished and ready for immediate enjoyment or rental income. THIS IS YOUR COASTAL ESCAPE...where luxury, location, and lifestyle all meet!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sabrina Ullmann (203-300-8181)
20 WHISPERING SANDS DR #1201, SARASOTA, FL 34242
$1,195,000101 Days on yellowkey MLS ID: A4678026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1282 Built: 1973Monthly Fee: $1,398 Tax: $10,552 (2025)Community: Whispering SandsCondo
Taxes:$10,552
Remarks: A truly RARE offering, this TOP floor, GULF FRONT penthouse residence crowns the northwest CORNER of the South Tower of Whispering Sands – the premiere 55+ Gulf front enclave on the idyllic westernmost point of Siesta Key where only a fortunate few enjoy world class, panoramic views of the sparkling Gulf and 800’ of PRIVATE quartz sand beach! FULL GULF views from this unit unfurl in every direction, offering a daily masterpiece of colors that shift with the rising and setting sun. Wake up to breathtaking Gulf views that seem to stretch to infinity, offering a tranquil retreat from the ordinary. In the evening, enjoy the golden hues of Florida sunsets and starlit dinners from your expansive 28’ balcony, where the Gulf breezes and soft cries of the seagulls serve as the perfect soundtrack. This penthouse is more than just a property – it’s also a canvas for your imagination. Distinctive architectural elements and premium untapped potential invite you to curate a space that reflects your own unique style and vision. Whether you envision modern sophistication, coastal charm, or timeless elegance, the untapped possibilities of this unit invite your imagination to run free as you create the ultimate sanctuary tailored to your personal vision. Whispering Sands' relaxed, informal lifestyle provides the perfect backdrop for your next chapter. Start your day with a set of vigorous laps or water aerobics in one of two beautiful, heated pools - one beachside, one clubside. You’ll never need to leave the property to get your gym workout in the main clubhouse currently undergoing a complete remodel. Plant your feet in the cool quartz sand and enjoy daily dips in the balmy Gulf. Beach loungers are set out daily for the exclusive use of owners. Enjoy an impromptu game of beachside shuffleboard followed by a picnic supper at the Tiki Hut. Whether spending time exploring the vibrant cultural offerings of Sarasota just across the North Bridge, indulging in the local arts scene, or simply relaxing on your breezy private balcony with a good book, the options this property offers are endless. Secure your private viewing of this unique residence and claim your place in this coveted coastal community!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
2534 GROVE ST, SARASOTA, FL 34239
$2,499,000251 Days on yellowkey MLS ID: A4662120
2 Days Off yellowkey (back on 4/16/2026)
Bed: 7 Bath: 7.0 Gar: 2 Liv Area Sq Ft: 4615 Built: 2025 Tax: $4,033 (2024)Community: South GateSpa: YesSingle Family
Taxes:$4,033
Elementary School: Southside Elementary
Remarks: Welcome to 2534 Grove Street, a new construction residence blending modern design with everyday livability in one of Sarasota’s most desirable neighborhoods. The open-concept main level features generous entertaining space with a gourmet kitchen, dining area, and living room that transitions seamlessly to the covered lanai and private courtyard-style backyard. The spacious first-floor primary suite provides convenience and privacy. Upstairs, a second lounge offers flexibility for media, office, or guests, along with additional ensuite bedrooms. Located in the Southside School district and just minutes from Downtown Sarasota, Siesta Key, and Lido Key. Brand new, move-in ready, and thoughtfully designed for the way you live.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Steven Moore (401-767-7180)
300 S PINEAPPLE AVE #302, SARASOTA, FL 34236
$1,649,000210 Days on yellowkey MLS ID: A4665439
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2291 Built: 2016 Tax: $19,826 (2023)Community: SansaraCondo
Taxes:$19,826
Tax Year: 2023
Middle School: Booker Middle
Remarks: Sansara Residence 302 | Boutique Downtown Luxury with Over 2,200 SF! Discover refined downtown living at Sansara, where modern design meets serene, resort-inspired luxury in the heart of Sarasota’s most walkable district. Just steps from the boutiques and cafes of Burns Court and minutes to the waterfront, Residence 302 offers an elevated retreat framed by lush greenery, sparkling pool views, and the soft glow of Sarasota’s city lights. Inside, nearly 2,300 square feet of thoughtfully curated living space unfolds with effortless elegance. Floor-to-ceiling glass filters natural light across wide-plank flooring, custom cabinetry, designer lighting, and motorized shades. The gourmet kitchen blends style and function with European soft-close cabinetry, quartz surfaces, a wine refrigerator, and premium Bosch appliances—an ideal backdrop for intimate dinners or laid-back evenings with friends. A spacious great room opens to a private terrace, inviting you to enjoy quiet morning coffee or sunset breezes above the pool deck. The split layout offers three bedrooms and three baths, each designed for comfort and privacy. The primary suite features a generous custom closet and spa-like bath with dual vanities and a walk-in shower. Two guest suites—one ideally suited as a den or office—provide flexibility for hosting or working from home. Outside your door, Sansara’s boutique amenities create a resort-worthy lifestyle: a heated saltwater pool and spa, cabanas, firepit lounge, outdoor kitchen and grill, plus a well-appointed fitness center—all secured within a private, gated setting. Some furnishings in Residence 302 are available for purchase, allowing you to move in with ease—or begin with a blank canvas and craft your bespoke dream home within one of downtown Sarasota’s most coveted boutique buildings. Experience the rare blend of sophistication, privacy, and walkability that defines life at Sansara. Welcome home to 300 S Pineapple Avenue, Residence 302.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Emmy Fitzpatrick (608-577-0053)
1350 MAIN ST #PH1600, SARASOTA, FL 34236
$1,995,000198 Days on yellowkey MLS ID: A4666660
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2165 Built: 2007 Tax: $14,766 (2025)Community: 1350 Main ResidentialCondo
Taxes:$14,766
Remarks: One or more photo(s) has been virtually staged. Rarely available penthouse on the 16th floor of sought-after 1350 Main in the heart of Downtown Sarasota! This beautiful 3-bedroom, 3-bath corner residence showcases spectacular Bay and city vistas from every room, upscale finishes and craftsmanship, and a wonderful open floor plan. Upon entry to the great room, you will enjoy the open light-filled room with 10' ceiling (only available on the top 3 floors), exquisite built-in, great space to showcase your personal art collection, and large terrace to relax and enjoy the bay breezes. The updated open-concept kitchen features stainless appliances including a high-end Thermador Professional-style gas range with 6-burner cooktop, 2 electric ovens, large center island, solid wood cabinetry, beautiful stone counters, and walk-in pantry. The split plan design boasts 3 spacious en-suite bedrooms including the primary bedroom with private terrace, custom walk-in closet and updated luxurious en-suite bath. Beautiful, engineered hardwood and ceramic tile floors throughout. 1350 Main is known for its great location, 24-hour concierge and on-site manager, secure entry, pet friendly building, and wonderful amenities including heated resort style pool and spa, recreation deck with gas grill, fire pit, herb garden, fitness center, steam rooms, guest suite, catering kitchen, social and conference/business rooms, electric car charging stations, and water softener/filtration in the entire building. The premier Downtown Sarasota address is perfect for proximity to all the cultural venues, art galleries, boutiques, Saturday farmers market, festivals, great restaurants, and proximity to the #1 Siesta Key Beach, Lido, and Longboat Keys.
Listing Agent: Lenore Treiman (941-356-9642)
3233 BENEVA RD #104, SARASOTA, FL 34232
$127,4508 Days on yellowkey MLS ID: A4690227
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 714 Built: 1978 Tax: $1,932 (2025)Community: Village Brooke Sec 3Condo
Taxes:$1,932
Elementary School: Wilkinson Elementary
Remarks: Home without the homework is yours with this condo. You'll love the beautifully groomed grounds here. You can live here affordably. Look at what the maintenance fee includes!!! All the neighbors have been so nice and helpful. Picturesque view from your lanai overlooking a picnic area and pond...or...you can bask in the sunshine poolside. Minutes to one of the best beaches in the world.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Debbie Roth (941-713-0522)
1717 ALTA VISTA ST, SARASOTA, FL 34236
$3,500,00015 Days on yellowkey MLS ID: A4689355
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3267 Built: 2023 Tax: $33,109 (2025)Community: Prime SubSpa: YesSingle Family
Taxes:$33,109
Middle School: Sarasota Middle
Remarks: Prime Location in the Hudson Bayou neighborhood. Built in 2023 this home offers 5 Bedrooms, 4.5 bathrooms and designer finishes. The interior features an open floor plan with wide plank wood flooring throughout and impact-rated windows and doors. The great room is anchored by a tray ceiling, custom built-ins, and a marble fireplace feature wall. The kitchen is designed for both everyday living and entertaining, offering Viking appliances, a dual fuel range, built-in refrigerator, custom cabinetry, quartz countertops, and a walk-in pantry. A dedicated wine room is located just off the kitchen. The primary suite is positioned on the first floor with direct access to the lanai, two custom walk-in closets, and a well-appointed bathroom with dual vanities, soaking tub, and frameless glass shower. The main level also includes a flexible office or guest suite with a full bath, along with a spacious laundry room. Outdoor living is fully integrated with a covered lanai featuring a complete outdoor kitchen with gas grill, vent hood, sink, and refrigerator, along with electric screens. The heated saltwater pool and spa are finished in PebbleTec and complemented by a gas fire feature, updated landscaping for privacy, and an outdoor shower. Upstairs includes three additional bedrooms, all with walk-in closets, two full bathrooms, and a loft space. Additional features include Sonos audio on the main level and natural gas generator. Located within the Southside Elementary school district, with a neighborhood park nearby. Downtown Sarasota, the Bayfront, Marie Selby Botanical Gardens, and Southside Village are all just minutes away, with convenient access to the Lido Key and Siesta beaches.
Listing Agent: Fred Sassen (404-408-5956)
7067 JARVIS RD, SARASOTA, FL 34241
$430,00013 Days on yellowkey MLS ID: A4687431
Bed: 4 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1608 Built: 1992 Tax: $2,406 (2025)Community: Lake SarasotaSingle Family
Taxes:$2,406
Elementary School: Lakeview Elementary
Remarks: Welcome to this spacious two-story, 4-bedroom, 2-bath home located in the desirable Lake Sarasota neighborhood—just minutes from I-75 with no HOA restrictions! Start your day on the charming screened-in front porch, the perfect spot for morning coffee or unwinding while enjoying a beautiful Florida sunset. Step inside to a bright and inviting living room and dining room combination, filled with natural light and ideal for both everyday living and entertaining. The kitchen has been recently updated with granite countertops and offers ample cabinet space, making it both stylish and functional for any home chef. Conveniently located on the main level, the primary bedroom features a walk-in closet and ensuite bathroom. Upstairs, you’ll find three additional bedrooms, including an oversized 16’ x 10’ room that offers endless possibilities—whether you envision a guest suite, home office, gym, or a space large enough to accommodate two queen beds. Step outside to a fully fenced backyard with plenty of room to add a pool and create your own private oasis. A storage shed adds extra convenience for tools and outdoor equipment. Enjoy peace of mind with recent updates including a new roof (2025) and a newer water heater. The home is located in an X flood zone, offers wind-resistant windows, and includes solar panels to help keep electric costs low. Conveniently situated near parks, schools, shopping, and recreational activities, this home offers the perfect blend of comfort, flexibility, and Florida living.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Edith Richman (941-855-0072)
7350 DEER CROSSING CT, SARASOTA, FL 34240
$549,900141 Days on yellowkey MLS ID: A4671132
0 Days Off yellowkey (back on 4/15/2026)
Bed: 4 Bath: 2.5 Gar: 3 Liv Area Sq Ft: 2210 Built: 2001Monthly Fee: $61 Tax: $3,151 (2024)Community: Meadow WalkSingle Family
Taxes:$3,151
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Welcome to Meadow Walk, where comfort and style come together in this stunning 4-bedroom, 2.5-bathroom pool home with a 3-car garage. Sitting on nearly a quarter-acre lot, this property showcases attractive curb appeal with beautifully maintained, low-maintenance landscaping. A screened front entry leads to double front doors, inviting you into a bright and spacious interior designed for both relaxation and entertaining. Inside, the foyer opens to soaring ceilings that create a grand first impression. The formal dining and living rooms are filled with natural light, and the living room features a unique two-way aquarium that connects to the kitchen, adding a touch of charm and character. The kitchen is a dream layout, offering abundant cabinetry, granite countertops, a large island, barstool seating, and a cozy breakfast nook. It seamlessly flows into the family room, highlighted by a tray ceiling and French doors that open to the lanai. The split-bedroom floorplan ensures privacy, with the owner’s suite situated on one side of the home. The oversized suite features a tray ceiling, private sliding glass door to the pool area, walk-in closet, and a spacious ensuite bathroom complete with dual sinks, a soaking tub, and a separate shower. The additional three bedrooms are generously sized, with nearby bathrooms providing convenience for family or guests. Enjoy the practicality of an indoor laundry room with ample storage, and step outside to the screened-in lanai that’s perfect for entertaining, featuring ceiling fans and plenty of lounging space around the sparkling pool. Beyond the screened area, a patio and fully fenced yard provide additional outdoor enjoyment and privacy. Ideally located near the scenic Celery Fields with beautiful walking trails, this home is close to premier shopping at UTC Mall, dining at Waterside, and within an A-rated school district including Tatum Ridge Elementary, McIntosh Middle, and Sarasota High School. This Meadow Walk gem truly has it all—schedule your private showing today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Keith Curcio (941-376-7683)
5272 BOX TURTLE CIR, SARASOTA, FL 34232
$624,99013 Days on yellowkey MLS ID: A4689433
Bed: 5 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2473 Built: 1985Monthly Fee: $50 Tax: $3,171 (2024)Community: Turtle Creek 2Spa: NoSingle Family
Taxes:$3,171
Elementary School: Fruitville Elementary
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Experience the ultimate blend of privacy, space, convenience and opportunity in this rare 1-acre estate situated in the highly sought-after community of Turtle Creek II. Positioned on a premier corner lot and enveloped by a lush canopy of majestic oaks, 5272 Box Turtle Circle features 5-bedrooms, 4-baths, including an attached 1-bedroom/ 1-bath in-law suite with a private entrance. Upon entering, you are greeted by an expansive open floor plan characterized by soaring ceilings and an abundance of natural light. The heart of the home is the beautifully updated kitchen and bright living area with French doors, featuring modern appliances, ample counter space, which flows seamlessly into the bright living and dining areas. For cozy evenings, the grand living room features a classic wood-burning fireplace, creating an inviting atmosphere for family gatherings. Opportunities galore as this second living room could also be featured as an addition to the Primary suite, offering you flexibility and versatility. The most unique and valuable feature of this property is the fully integrated in-law suite. Complete with its own private exterior entry and a dedicated kitchenette, this versatile space is perfect for multi-generational living, a long-term guest retreat, or a secluded professional home office. Market rent for the attached suite is $1,500 per month which is an opportunity to offset your mortgage or be another stream of income. The interior layout is thoughtfully designed for flexibility, offering five true bedrooms to accommodate a variety of lifestyle needs. Step through the French doors to discover your own private oasis. The oversized screened-in patio provides the perfect setting for alfresco dining or morning coffee while overlooking the massive, park-like backyard. With a full acre of land, there is limitless potential for outdoor recreation, gardening, or adding a custom resort-style pool. This property offers the rare luxury of land and privacy while maintaining a HardiPlank exterior for lasting curb appeal. Roof is only 3 years old! Located in a quiet, established neighborhood with no CDD fees and low HOA dues, you are just minutes from I-75, the UTC shopping district, and Sarasota’s world-famous beaches. This is a rare opportunity to secure a significant piece of land in one of the Gulf Coast's most convenient and desirable locations. Be sure to experience the full 3-D Interactive Walkthrough and schedule your private viewing today!
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Andrew Haddad (941-313-1218)
191 VISTA HERMOSA CIR, SARASOTA, FL 34242
$570,00077 Days on yellowkey MLS ID: A4680721
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 993 Built: 1971Monthly Fee: $1,104 Tax: $4,566 (2025)Community: Vista HermosaVilla
Taxes:$4,566
Remarks: One or more photos have been virtually staged. Welcome to your maintenance free, dream beach retreat on Siesta Key! This charming and meticulously remodeled 2-bedroom, 2-bath villa offers the perfect blend of luxury and convenience, just a short stroll from the pristine sands of Crescent Beach. Enjoy cooking in a stunning kitchen featuring brand new quartz countertops, stainless steel appliances, and stylish light fixtures. Experience comfort year-round with newly installed HVAC and energy-efficient tankless water heater. Luxury vinyl panel floors flows seamlessly throughout, offering both durability and aesthetic appeal. Relax in the attached, screened-in lanai, complete with No-See-Um screen, aluminum framing and a new Hunter, wet-rated ceiling fan, perfect for warm island evenings. Both bathrooms have been beautifully remodeled providing a fresh, contemporary feel. Located just a few steps from the Clubhouse, heated pool, outside grilling areas and laundry facility. Walking distance to shops, restaurants and entertainment. Enjoy the easy, island lifestyle with access to the free trolley service to Siesta Key Village for even more shopping and dining experiences. Ideal for a second home, rental investment, or full-time residence. Don't miss this great opportunity to own a piece of paradise! Schedule your showing today and embrace the Siesta Key lifestyle!
Listing Agent: Denise Barbato (941-400-8773)
157 VISTA HERMOSA CIR, SARASOTA, FL 34242
$569,00087 Days on yellowkey MLS ID: A4677280
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1971Monthly Fee: $1,041 Tax: $3,568 (2025)Community: Vista HermosaVilla
Taxes:$3,568
Remarks: Completely renovated in 2025, this 2 bedroom/2 bath, maintenance free villa is walking distance to the powdery sands of beautiful Crescent beach on Siesta Key. Great opportunity for a second home, vacation rental or full-time residence. 2-week minimum, 26 times a year rental policy. All kitchen upgrades include new cabinets, quartz countertop, sink and all new stainless steel appliances including, microwave, refrigerator, stovetop and dishwasher. Convenient all new washer and dryer in unit! New tile flooring throughout. Amenities include a renovated clubhouse with full kitchen, heated swimming pool and outdoor grilling areas. This well-managed island retreat is located just a short distance to restaurants, shopping, entertainment and water sports. Enjoy the stress free, beach lifestyle of Siesta Key!
185 VISTA HERMOSA CIRCLE, SARASOTA, FL 34242
$575,000196 Days on yellowkey MLS ID: A4667525
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1036 Built: 1971Monthly Fee: $1,041 Tax: $5,222 (2024)Community: Vista HermosaSpa: NoVilla
Taxes:$5,222
Remarks: Welcome to Vista Hermosa, your ultimate maintenance-free, island retreat a short stroll from the powdery sands of Crescent Beach on world renowned Siesta Key. This beautifully renovated villa is turnkey-furnished and move-in ready with brand new upgrades including luxury vinyl flooring throughout, quartz countertops in kitchen and bath, stainless steel appliances including, dishwasher, stove top and microwave and a newly installed A/C system. Amenities include a renovated club house with full kitchen, heated swimming pool and grilling areas. Vista Hermosa is located just a short distance to restaurants, shopping, entertainment and water sports. Enjoy the convenience of living close to Stickney Point bridge where you can venture off the Key and within a short drive visit Downtown Sarasota, St. Armand's Key, Longboat and Lido Keys. Great opportunity for a second home, vacation rental or full-time residence. 2-week minimum, 26 times a year rental policy allows for great income potential! Own a piece of paradise and enjoy the laid back, tropical lifestyle of Siesta Key. Schedule a showing today!
1255 E PEPPERTREE DR #201, SARASOTA, FL 34242
$499,000255 Days on yellowkey MLS ID: A4661191
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1460 Built: 1972 Tax: $5,890 (2024)Community: Peppertree Bay ISpa: NoCondo
Taxes:$5,890
Remarks: Move in ready AND priced to sell quickly! Don't miss the chance to own this beautifully updated turnkey furnished 2-bedroom condo at Peppertree Bay, available at an unbeatable price! Experience resort-style living in this bayfront and beachside community. The interior boasts an open floor plan with spacious, welcoming rooms, tile and luxury vinyl plank flooring, and a generous 29-foot lanai. Peppertree Bay offers luxurious amenities, including under building parking, private beach access, two heated swimming pools, tennis and pickleball courts, two clubhouses, a fitness center, and a fishing pier. It’s like a vacation every day! When you want a change of pace, leave your car behind and take the trolley to all the wonderful restaurants and shopping Siesta Key has to offer. With onsite management and a rental desk, this Peppertree Bay condo serves as an ideal coastal getaway or a smart investment choice. Don’t let this one get away.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
209 COSMOPOLITAN CT, SARASOTA, FL 34236
$899,00070 Days on yellowkey MLS ID: A4676613
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1680 Built: 2015Monthly Fee: $575 Tax: $10,906 (2025)Community: QSpa: NoTownhouse
Taxes:$10,906
Remarks: Amazing property and location! This Townhome is located between Osprey and Orange Avenues off of Ringling Blvd. in downtown Sarasota with 2 spacious bedrooms and 2.5 Baths. The Q is a unique enclave of 40 individually owned townhomes (not a condo). The moment you enter the front door, you will be mesmerized by the 13-foot-tall ceilings, the 8'-foot-tall solid wood Italian doors and a serene view through the foyer out the back door to historic Laurel Park. The downstairs area (11' x 10') is a great office space with large windows that could also work as a den. The second bedroom is conveniently located on the first floor and boasts both a walk-in closet and a double closet. This spacious second bedroom has an ensuite bathroom with a Lube single sink cabinet with quartz countertops and an oversized walk-in shower. Landry room is also, conveniently located on level one. On level 2, At the top of the stairs you are greeted by an amazing kitchen with Modern cabinets, quartz countertops and stainless-steel appliances. The glass tile backsplash and knee wall facing the living room are stylist and accessible, shimmering with light from the over-sized windows. The view from the upstairs living room and dining room is a scenic view of the treetops of historic Laurel Park. Step out onto the serene, private balcony where you feel like you're in the treetops. All windows are impact glass. The attached 2-car garage has spacious storage. The location is ideal. You are two blocks from the Saturday farmer's market and one block from amazing restaurants. If that's not enough, stroll to the theater, opera, or the marina. The Q is a very short ride or walk to the Legacy Trail connecting you from downtown to Venice. The free Breeze trolley runs every 30 minutes to takes you to St. Armand's Circle or out to Lido Beach. Buyers and/or Buyers Agent to verify all pertinent information, including room sizes, as they may be approximate. All Association information should be verified with Property Management Company or Association. Information deemed reliable but not guaranteed.
Listing Agent: Robert Robinson (941-587-2739)
4140 MALDEN DR, SARASOTA, FL 34241
$449,000189 Days on yellowkey MLS ID: A4668055
REDUCED by $20,000 (4.3%) on 04/07/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1964 Built: 2000 Tax: $3,655 (2024)Community: Lake SarasotaSingle Family
Taxes:$3,655
Remarks: Under contract-accepting backup offers. This is the one * 'A' RATED SCHOOL DISTRICT * NEW ROOF IN 2020 * NEW A/C IN 2020 * LOVINGLY REMODELED FAMILY HOME * A TRUE 4 BEDROOM SPLIT PLAN with 2 BATHS * This comfortable, generously-sized open floor plan features a Living Room + Dining Room + Family Room * SPACIOUS Kitchen features a breakfast bar and has newer appliances, fixtures and GORGEOUS GRANITE counters * Screened lanai with door to 2nd Bath * Private fenced yard for privacy * THE BACKYARD IS A BEAUTIFULLY LANDSCAPED OASIS * This home is perfect for entertaining or simply relaxing in your slice of paradise * You'll love living on this quiet street in the newer section of Lake Sarasota * 'A' RATED SCHOOL DISTRICT * Fantastic location - you're just minutes to parks, I-75, shopping, restaurants, Doctor's Hospital, and so much more * It's a short drive to Siesta Key Beach, downtown and even UTC Mall * One look & you'll fall in love *
Listing Agent: Glenn Brown (941-342-6464)
527 FREELING DR, SARASOTA, FL 34242
$5,825,000129 Days on yellowkey MLS ID: A4669657
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 4310 Built: 2026 Tax: $6,458 (2024)Community: Bay Island ShoresSpa: YesSingle Family
Taxes:$6,458
Remarks: Under Construction. The exterior presentation of this spectacular waterfront residence is most impressive with its blend of modern architecture and refined luxury. With superior elevation high above the water’s edge on Siesta Key’s prestigious Bay Island, this new to-be-built 4,310 sq. ft. residence is an unparalleled oasis of tranquility in a breathtaking setting. A place where architectural elegance and natural beauty converge in perfect harmony with elaborate artisanal work, functional design, and top-tier amenities. For boaters, the location is ideal with a new seawall and a private dock allowing quick access to the bay and gulf beyond. Built with intention and quality, large windows flood the space with natural light illuminating the graceful enhancements within. When entering the home through the 4-car garage, an elevator takes you to the first and second living levels. An elegant foyer entry with double-height ceiling and sleek iron-railed staircase usher you into the spacious interiors where every detail, from the fluid layout to the custom finishes, is thoughtfully curated. Adding a distinctive touch to the stunning great room are 20-foot ceilings and a two-story entertainment wall flanked by artistic display niches. A wall of glass sliders sets a dramatic tone, framing water views and uniting indoor-outdoor living. Designed for effortless entertaining and timeless family gatherings, the outdoor area overlooks the water to create a tranquil setting that feels both secluded and well-connected. With nearly 500 sq. ft. of covered lanai, an outdoor cook center and a heated pool/spa, there’s ample opportunity for hosting special gatherings or simply enjoying the quiet beauty laid before you. Lovely landscaping, lush greenery and outdoor spaces add to the home's overall aesthetic appeal. A remarkable gourmet kitchen is designed for functionality and style, equipped with high-end finishes, top-tier appliances, a large island and a butler’s pantry with additional refrigerator and dishwasher. An adjoining dining room comfortably seats 8-10 and offers wonderful water views while dining. The primary wing is remarkable with an exquisite spa bath, enlarged customized wardrobe room, and direct access to the laundry facilities. The first level also includes a den suite ideal for remote work or creative pursuits and a completely private guest bedroom with its own full bath. Upstairs, there’s an overlook to the great room below, 2 bedrooms, 2 full baths, and an amazingly-sized bonus room with private balcony. The award-winning and talented team of professionals at Allegra Homes has thoughtfully and expertly created a residence offering a secure, exclusive lifestyle in one of Sarasota's most sought-after and high-value areas. The construction quality is of the highest standard, ensuring that the home is both beautiful and built to last. Just minutes to the mainland, downtown’s cultural mecca, world-class dining and shopping venues, gorgeous area beaches and a top-ranked school system coveted by families for generations, the prized waterfront location couldn’t be better. Showcasing extraordinary craftsmanship throughout, this never-lived-in showplace is the ultimate vision for those who value the very best of coastal Florida living. There’s still time to make your own personal choices for creating the perfect custom home tailored to your family’s taste and style.
Listing is courtesy of: GRECO REAL ESTATE (941-685-0449)
Listing Agent: Karen Greco (941-504-6927)
1260 DOLPHIN BAY WAY #404, SARASOTA, FL 34242
$1,395,000142 Days on yellowkey MLS ID: A4673762
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1997 Tax: $12,793 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,793
Remarks: ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a single family home with charm and character. The kitchen was custom built by Yoder Construction, a well-known local company, highly respected for their craftsmanship. Living room and dining area are bright and spacious. The large primary bedroom has a walk-in closet and ensuite with shower and separate soaking tub. There are two other ensuite bedrooms. All three bedrooms have California Closet systems. All windows have custom plantation shutters, adding to the charm and comfort of this amazing condo. You will want to spend your day on the light filled lanai, perfect for entertaining or simply relaxing. Dolphin Bay is a highly desirable, gated, pet friendly, 50-unit complex with a fun filled community atmosphere with three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier and kayak access. Dolphin Bay is well maintained with a freshly updated exterior and new elevators in 2024 and beautifully landscaped grounds. Just a short walk to the world famous, white crystal sands of Siesta Key beach.
1939 HIGH POINT DR, SARASOTA, FL 34236
$1,335,000108 Days on yellowkey MLS ID: A4676860
REDUCED by $20,000 (1.5%) on 04/15/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2478 Built: 1954 Tax: $8,592 (2025)Community: High Point CircleSingle Family
Taxes:$8,592
Remarks: Tucked just moments from Hudson Bayou and Sarasota Bay, this gated mid-century modern compound offers a rare opportunity to own a meaningful piece of Sarasota’s architectural and artistic history while embracing a lifestyle that feels both inspired and entirely livable. Originally built in 1954 as a Ruth Richmond design and later reimagined by nationally recognized abstract artist Steve McCallum, the property blends authentic mid-century lines with bold creative character. Set behind walls and framed by lush tropical landscaping, the home unfolds as a private retreat within one of Sarasota’s most desirable cultural corridors. A paver drive leads to the striking architectural façade, clerestory windows, and modern courtyard entry. Inside, natural light pours through high transom windows and expansive sliding glass doors, highlighting the openness and warmth that define true mid-century design. The main residence offers three bedrooms and two full baths, with an open living and dining layout that flows effortlessly to the courtyard pool. Clean lines, tile flooring throughout, and thoughtful updates create a space that feels timeless yet comfortable. The private courtyard pool anchors the compound, surrounded by palms, bamboo, and multiple seating areas designed for relaxed evenings or intimate gatherings. The setting offers privacy without sacrificing proximity to downtown and the bayfront. The studio structure truly elevates the estate. Measuring approximately 56 by 32 feet with soaring 16-foot ceilings, it was purpose-built for large-scale creative work and now offers remarkable flexibility. With its own private entrance and a dedicated bathroom, the studio can function independently as a guest retreat, executive workspace, gallery-style studio, or wellness space. The space also includes a walk-in closet area that currently functions as both a walk-in closet and laundry room, adding additional convenience and functionality. An interior hallway also connects it to the main home, allowing seamless use for multigenerational living or extended guests while maintaining the option for complete privacy. For several years, the studio operated as a curated, owner-hosted guest experience, earning more than 200 five-star reviews and establishing itself among Sarasota’s earliest luxury short-term stays. That history speaks to its design appeal, comfort, and versatility. In addition to the main living spaces, the property also features an approximately 200 square foot storage room connected to the studio. This flexible area can easily function as an extension of the studio when the roll-up door is opened, creating additional usable space for creative work, storage, or studio expansion. Offering 2,478 square feet under air across both structures, this property delivers architectural authenticity, creative scale, and compound-style living just minutes from downtown dining, galleries, and Sarasota’s renowned arts scene. This is a mid-century modern lifestyle property for those who value design, flexibility, and the freedom to shape a home around how they truly want to live. **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Toni Zarghami (941-248-2147)
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