Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
5273 HERON WAY #202, SARASOTA, FL 34231
$489,500207 Days on yellowkey MLS ID: A4670409
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1775 Built: 1986 Tax: $5,616 (2025)Community: Landings South 3Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,616
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Newly installed HURRICANE IMPACT WINDOWS and a 2024 AC with transferable warranty make this second-floor coach home a low-maintenance, move-in ready choice. Enjoy expansive water views and a prime location just a short walk to the Racquet Club and pool in the highly sought-after Landings community. Inside, a bright, open layout features vaulted ceilings and consistent flooring with no step-down, creating a seamless living space. The updated kitchen offers granite countertops, a breakfast bar, and stainless steel appliances, flowing into the main living area with water views. The primary suite also overlooks the water and provides generous space for a sitting or work area, along with a large bathroom and walk-in closet. Two additional bedrooms share a full bath, while plantation shutters add a timeless finish throughout. Additional features include a separate laundry room and a newer roof and gutters installed in 2023. Residents enjoy access to the Landings Racquet Club with eight Har-Tru tennis courts, fitness center, pro shop, heated lap pool and spa, and an active year-round social calendar. A private nature trail leads to a covered dock, fishing pier, and kayak and paddleboard storage. Ideally located west of the Trail, The Landings is minutes from Siesta Key, Southside Village, and Downtown Sarasota, offering excellent dining, shopping, and convenience.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Yvette Sellyn (941-730-7756)
1516 FOX CREEK DR, SARASOTA, FL 34240
$1,899,50080 Days on yellowkey MLS ID: A4683593
REDUCED by $100,000 (5.0%) on 05/02/2026
Bed: 6 Bath: 5.5 Gar: 8 Liv Area Sq Ft: 4277 Built: 1973 Tax: $14,746 (2025)Community: Fox Creek AcresSingle Family
Taxes:$14,746
Elementary School: Southside Elementary
Remarks: One or more photo(s) has been virtually staged. 3 HOMES for the Price of One! MULTI-HOUSING/INCOME PRODUCING OPPORTUNITY Two separate 3BR/2BA Homes + an additional 2BR/2BA Apartment. Each of the homes enjoys its own private entrance, separate driveway and its own garage, allowing households to live side by side while maintaining independence. And that's not all....the Workshop features a Full Bath and Laundry Room. In addition, there is another Barn which could accommodate 4+ Cars. This is truly a Quintessential Multi-Generational Compound on five-plus acres in Sarasota county, located adjacent to Waterside at Lakewood Ranch! Whether accommodating extended family, long-term guests or providing a private residence for caregivers, the thoughtful layout offers exceptional versatility. At the heart of the property, a beautiful pool and expansive screened lanai create an inviting backdrop for a Florida indoor/outdoor lifestyle. This outdoor retreat is positioned so both residences could enjoy easy access, making it a natural gathering place for family and guests alike. A dedicated pool bath adds convenience for swimmers and guests, keeping the indoor living areas pristine while enhancing seamless flow between indoor comfort and outdoor enjoyment. Expanding the living possibilities, perhaps you might want to consider using part or all of this property as Airbnb. The second-level apartment offers privacy with a light and airy vibe featuring an open plan and full kitchen. The unique adjoining sunroom spanning the length of the unit would be ideal for a yoga studio, game room or added entertainment space. Unlock the potential of this versatile apartment as a guest retreat, income-producing rental, inspiring studio or private office suite. This five-plus acre homesite with NO HOA, NO CDD's, and NO DEED RESTRICTIONS gives you the freedom to tailor the property to your personality. The large detached pole barn adds tremendous utility, providing ample space for farm animals, boats, RVs, equipment, hobbies or workshop use, ideal for those who need room to store, build or play. Buy with confidence knowing this home has a whole house generator, updated plumbing with no cast iron or copper piping. The cast iron sewer pipes have been replaced with PVC and the copper potable water pipes have been replaced with CPVC. The 4Point Inspection and Wind Mit has been completed. Homeowner's Insurance only $6700 per year! Experience the balance of peaceful country living with an unbeatable location. Within minutes of restaurants, boutiques, farmers markets, parks, and year-round events at the vibrant waterfront district at Waterside Place in Lakewood Ranch and only a short drive to the stunning beaches and renowned dining and cultural attractions of dynamic Sarasota. The home is positioned in one of the areas most dynamic growth corridors, just minutes to the newest Lakewood Ranch developments along Fruitville Rd corridor ~ where premier shopping, exceptional dining and modern conveniences continue to flourish! Whether you envision a private family compound, a multi-generational retreat, an income-producing opportunity or a flexible live-work estate, this remarkable property offers the rare combination of space, freedom and location. Schedule your private showing today and experience the endless possibilities for yourself. Welcome home to 1516 Fox Creek Drive! Tour it, Love it, Own it Today!
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-907-9541)
Listing Agent: Trish Chandler (941-306-9533)
2415 PELICAN DR, SARASOTA, FL 34237
$480,000291 Days on yellowkey MLS ID: A4659633
REDUCED by $39,000 (7.5%) on 05/18/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1494 Built: 1950 Tax: $4,460 (2024)Community: Terrace GardensSingle Family
Taxes:$4,460
Elementary School: Alta Vista Elementary
Tax Year: 2024
Middle School: Booker Middle
Remarks: Charming 1950s Florida Ranch-Style Home with Separate One-Bedroom Apartment in Sought-After Terrace Gardens! Don’t miss this rare opportunity to own a classic mid-century Florida ranch home in the desirable Terrace Gardens community. Situated on an expansive corner lot, this single-family residence offers exceptional flexibility, income potential, and future development possibilities. The main home features 2 bedrooms and 1 bath, showcasing original wood floors in the bedrooms, generously sized closets, and a delightful lanai-style sitting room perfect for relaxing. A beautifully carved-out one-bedroom, one-bath apartment provides a private space ideal for guests, extended family, or rental income—both units are currently rented. Whether you're looking to generate income immediately or envision building your dream home in a neighborhood filled with new construction, this property offers endless possibilities. Enjoy the unbeatable location: bike the nearby Legacy Trail, explore downtown’s vibrant restaurants and cultural scene, play at Payne Park, or spend the day at the beach—all just minutes away.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Ingrid Caruso (941-539-6233)
$480,000395 Days on yellowkey MLS ID: A4650716
Bed: 3 Bath: 0.0 Liv Area Sq Ft: 1494 Built: 1950 Tax: $4,460 (2024)Community: Terrace GardensApartment
Remarks: Charming 1950s Florida Ranch-Style Duplex in Sought-After Terrace Gardens! Don't miss this rare opportunity to own a classic mid-century Florida ranch home, smartly divided into two separate units in the desirable Terrace Gardens community. Situated on an expansive corner lot, this property offers flexibility, income potential, and future development possibilities. Unit 2415 features 2 bedrooms and 1 bath, while Unit 2417 offers 1 bedroom and 1 bath—both currently rented. Inside, you'll find original wood floors in the bedrooms, generously sized closets, and a delightful lanai-style sitting room perfect for relaxing. Whether you're looking to generate rental income right away or dreaming of building your own custom home in a growing neighborhood filled with new construction, this property offers many options. Enjoy the lifestyle that comes with this prime location: bike the nearby Legacy Trail, explore downtown’s vibrant restaurants and cultural scene, play at Payne Park, or spend the day at the beach—all just minutes away.
2461 RINGLING BLVD, SARASOTA, FL 34237
$499,000319 Days on yellowkey MLS ID: A4658766
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1487 Built: 1955 Tax: $4,739 (2024)Community: Ringling Blvd SubSingle Family
Taxes:$4,739
Remarks: Unlock the potential of this ideally situated property on Ringling Boulevard—just minutes from downtown Sarasota, the Marina, and Gulf beaches. Whether you're planning a full-scale renovation or a complete teardown for new development, this 2-bedroom, 2-bath home offers solid value in a rapidly evolving corridor. Featuring an open floor plan, carport, workshop area, and a sunlit Florida room, the existing structure provides flexibility for updates. Yet, the true opportunity lies in the land, positioned along the prominent Ringling Blvd. with redevelopment momentum.
4103 CENTER GATE BLVD #2, SARASOTA, FL 34233
$269,90067 Days on yellowkey MLS ID: A4687187
REDUCED by $10,000 (3.6%) on 05/08/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1601 Built: 1979 Tax: $2,106 (2025)Community: Center Gate VillageVilla
Taxes:$2,106
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: Price Improvement – Sellers Motivated to Sell. Welcome to this spacious Villa in the desirable Center Gate Village community. Offering over 1,600 square feet of comfortable living space, this 2-bedroom, 2-bath villa features a thoughtfully designed floor plan perfect for both everyday living and entertaining. Enjoy the community pool and creek views right in your backyard. The expansive living and dining areas are filled with natural light, creating a warm and inviting atmosphere. The well-appointed kitchen provides ample cabinetry and workspace, with easy flow into the main living areas. The generous primary suite offers privacy and comfort, complete with a walk-in closet and en-suite bath. A second bedroom and full guest bathroom make this home ideal for visitors or a home office setup. Additional highlights include an attached garage for convenient parking and extra storage, new LVP flooring, interior laundry space, and abundant closet space throughout. Residents enjoy low-maintenance living with HOA-covered exterior maintenance and beautifully maintained grounds, along with access to a community pool. Ideally located in central Sarasota, you're just minutes from shopping, dining, medical facilities/Doctors Hospital, I-75, downtown Sarasota, and the world-renowned beaches of Siesta Key!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Blair Schrock (970-666-1240)
1160 WAGON WHEEL DR, SARASOTA, FL 34240
$1,525,000176 Days on yellowkey MLS ID: A4673997
REDUCED by $75,000 (4.7%) on 05/18/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2467 Built: 1976 Tax: $5,221 (2024)Community: Fox Creek AcresSingle Family
Taxes:$5,221
Remarks: Welcome to a private 5 acre luxury estate, a rare multi residence retreat in the heart of Sarasota. Tucked behind a picturesque canopy of mature oaks and white ranch fencing, this exceptional property offers unmatched space, serenity, and versatility, featuring a beautifully maintained main residence, a fully equipped two story barn home with both upstairs and downstairs living accommodations, a sparkling saltwater pool, and acres of cleared usable land. The main home offers 3 bedrooms plus a large game room with a full closet that can serve as a fourth bedroom, office, or flex space depending on the buyer’s needs, along with multiple living areas and wide open spaces filled with natural light and peaceful views of the pool and surrounding acreage. Meaningful updates include appliances replaced in 2024, a whole house water softener system in 2024 including the apartment, septic pumped in 2024 with a new leech bed installed for both the home and apartment, a saltwater pool pump replaced in 2024, AC replaced in 2020, water heater replaced in 2019, and a durable metal roof from 2008. The expansive kitchen opens to the pool and living areas, complemented by a beautiful stone fireplace and a large bonus room perfect for a billiards room, playroom, gym, or hobby space. Outdoor living shines with a fenced saltwater pool and paver deck, ideal for sunny afternoons and relaxed evenings under the mature oak trees. The two story barn home is divided into two separate units, offering incredible flexibility for multigenerational living or rental income. The upstairs unit features 2 bedrooms and 1 and a half bathrooms, along with 2015 appliances and a private screened balcony overlooking the property. The downstairs unit includes 1 bedroom and 1 bathroom, updated flooring, granite counters, a 2020 stove and dishwasher, and a 2022 refrigerator. The barn also features a metal roof from 2006 and benefits from the recent septic upgrades. The full 5 acres are fully fenced and usable, perfect for horses, gardens, recreational vehicles, or future expansion, all accessed by a beautiful winding paved driveway and an oversized three car garage. This property offers peaceful privacy while still being close to shopping, dining, medical facilities, parks, I 75, and just a short drive to Siesta Key, Lido Key, and the world renowned Gulf Coast beaches.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Katie Cobb (913-744-0248)
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,395,00066 Days on yellowkey MLS ID: A4687301
REDUCED by $200,000 (3.6%) on 05/18/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$25,684
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)
630 VENICE LN, SARASOTA, FL 34242
$975,000214 Days on yellowkey MLS ID: A4669940
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1859 Built: 1971 Tax: $8,446 (2024)Community: Siestas Bayside Waterside EastSpa: NoSingle Family
Taxes:$8,446
Remarks: One or more photo(s) has been virtually staged. Nestled near the gentle waters of Roberts Bay, this enchanting Siesta Key home rests on a quiet cul de sac street where the only sounds are the whisper of palms and the laughter of neighbors walking by. T location captures the essence of island life — peaceful, private, and just moments from where the sun dips into the Gulf. A short stroll or quick bike or golf cart ride has you in the center of vibrant Siesta Key. This home is dependable and offers new hurricane impact-rated windows, garage door and sliders; re-lined plumbing lines as well as new pex water supply lines throughout; and a new HVAC system and water heater. Step inside, and you’ll feel the warmth of a home that’s been lovingly renewed. Every detail reflects care and comfort — from the four inviting bedrooms and two full baths to the light-filled kitchen adorned with stainless steel appliances and a captivating blue glass tile backsplash reminiscent of the Gulf waters just moments from your front door. The dining area invites long, easy meals, while two separate living spaces offer versatility for gathering, relaxing, or simply enjoying the rhythm of coastal living. Life is low maintenance and carefree with durable lvp flooring that looks modern and will compliment your coastal décor. Beyond the back door lies a spacious, fenced yard — a blank canvas waiting for your imagination. Picture a pool glimmering under the afternoon sun, a lush garden framed with tropical blooms, or a firepit where evenings stretch into starlit conversations. Here, you aren’t confined to someone else’s vision — you have the freedom to create your own perfect oasis suited to your tastes and dreamy outdoor vibe. The charming front porch welcomes your guests — a cheerful prelude to the life that awaits within. New hurricane-rated windows offer confidence and calm, while the spacious two-car garage with smart epoxy flooring and the generous, indoor laundry room offers convience. This is more than a house; it’s a fresh beginning on Siesta Key — a place where your coastal dream can take root.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
915 SEASIDE DR #412, SARASOTA, FL 34242
$1,799,000110 Days on yellowkey MLS ID: A4681675
REDUCED by $200,000 (10.0%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1750 Built: 2009 Tax: $16,278 (2025)Community: Siesta Key Beach Residences IiSpa: YesCondo
Taxes:$16,278
Remarks: Welcome to a premier Siesta Key Beach condo that delivers the ultimate combination of luxury coastal living and high-performing rental income potential. This beautifully updated 3-bedroom, 2-bath condominium is professionally managed through an established onsite program, offering owners a seamless, turnkey experience with the ability to enjoy the home personally while also participating in a proven, income-producing rental program. Located directly on world-famous Siesta Key Beach, consistently ranked among the top beaches in Florida, the U.S., and the world, this property benefits from strong year-round demand for high-end vacation rentals. Whether you’re looking for a beachfront vacation home, a short-term rental investment, or the ideal blend of both, this residence is positioned to deliver outstanding lifestyle value and long-term upside. The current owner has successfully utilized the rental program while still enjoying substantial personal use, making this an exceptional opportunity for buyers seeking a condo with documented rental history and the flexibility to reserve premium seasonal time for themselves. Inside, the condo features a bright, open layout with spacious living areas and finishes that appeal to both owners and guests. Enjoy partial Gulf of Mexico views and Siesta Key Beach scenery from the primary suite, living room, and private lanai—capturing the coastal lifestyle today’s vacation renters are looking for. Owners and guests enjoy access to desirable resort-style amenities, including a sparkling pool, fitness center, concierge services, and professional onsite management. With unbeatable beach access, nearby attractions, and a consistent track record of rental demand, this is one of the most compelling income-producing condos on Siesta Key. Schedule your private showing today and discover the value of owning a luxury Siesta Key vacation rental property.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Kelly Mooney (941-587-8430)
8750 MIDNIGHT PASS RD #302, SARASOTA, FL 34242
$429,000117 Days on yellowkey MLS ID: A4680093
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 800 Built: 1980 Tax: $4,916 (2025)Community: TortugaCondo
Taxes:$4,916
Remarks: Come live the dream in this great "fully furnished" residence on the south end of Siesta Key. Share amenities with Turtle Bay across the street like tennis, pickleball, and boat slips. Directly on the gulf, enjoy beach and sun year round. Secure, under building covered parking. Washer/dryer combo in unit! This unit is clean and in fabulous condition and comes fully furnished. Situated at the southern end of Siesta Key, it offers a more remote feel. Take the trolley into the village for dinner and shopping. This unit shows excellent and is priced right!
Listing is courtesy of: HOUSEMAX REALTY LLC (941-315-1990)
Listing Agent: Paul Defelice (941-315-1990)
111 S PINEAPPLE AVE #806, SARASOTA, FL 34236
$1,745,00064 Days on yellowkey MLS ID: A4687850
REDUCED by $50,000 (2.8%) on 05/18/2026
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1891 Built: 2019 Tax: $12,679 (2025)Community: Mark Sarasota CondoCondo
Taxes:$12,679
Remarks: Experience refined downtown living at Sarasota’s premier address, The Mark. This 8th-floor end unit offers 2 bedrooms plus a den, 2.5 bathrooms, and abundant natural light with a desirable south-facing terrace and additional east and west views. The thoughtfully designed floor plan features two private terraces, including a unique triangular terrace off the main living area and a second terrace off the primary suite. Interior highlights include porcelain tile and engineered hardwood flooring, a spacious walk-in closet with custom built-ins in the primary bedroom, custom built-ins in the guest bedroom, and remote-controlled shades throughout. The kitchen showcases a modern European design with glossy white upper cabinetry, wood-grain lower cabinets, a full-height backsplash, and top-of-the-line appliances. Enjoy unmatched walkability with shops, restaurants, and galleries just steps from your door, offering the ultimate downtown Sarasota lifestyle.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Amber Watson (229-392-8892)
95 S BRIGGS AVE, SARASOTA, FL 34237
$449,000133 Days on yellowkey MLS ID: A4678771
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1512 Built: 1974 Tax: $5,229 (2024)Community: Golfview SubSingle Family
Taxes:$5,229
Remarks: Discover a rare opportunity to own a move in ready home in the highly desirable Ringling Park neighborhood, right in the heart of Sarasota. Situated on an oversized corner lot beneath beautiful mature oak trees, this property offers exceptional outdoor space, privacy, and timeless curb appeal that is hard to find this close to downtown. Inside, the well maintained home features wood cabinetry, granite countertops, stainless steel appliances, and a flexible bonus room ideal for a home office, den, or additional living space. The single car garage, fully fenced yard, and easy care landscaping add both convenience and functionality. Enjoy an unbeatable location just blocks from downtown Sarasota and only 4 miles to St. Armands Circle, placing world class shopping, dining, entertainment, and beaches within easy reach. With no deed restrictions and a large corner lot, this property offers a rare combination of flexibility, charm, and location in one of Sarasota’s most convenient neighborhoods.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Seth Westerberg (941-342-7653)
3210 HIGEL AVE, SARASOTA, FL 34242
$11,950,000157 Days on yellowkey MLS ID: A4676047
Bed: 4 Bath: 4.5 Gar: 3 Liv Area Sq Ft: 3884 Built: 2026 Tax: $26,394 (2025)Community: Siesta Rev OfSpa: YesSingle Family
Taxes:$26,394
Elementary School: None
Remarks: Under Construction. Perfectly positioned on the highly coveted north end of Siesta Key, this exceptional property overlooks the aquamarine waters of Big Pass and the Gulf of Mexico where dolphins frolic in your backyard. To be custom built by renowned builders - Trend Homes, the residence is thoughtfully designed to capture the very best of island living. The home will feature exquisite custom kitchen cabinetry paired with top-of-the-line appliances, along with elegant stonework and refined millwork throughout. The spacious primary suite offers generous walk-in closets, while expansive windows provide breathtaking water views from nearly every room. Additional highlights include a 3-car garage, and an open, light-filled floor plan ideal for both everyday living and entertaining. Offering over 4,500 square feet of living space, the home includes four bedrooms and four and half bathrooms. Outdoor amenities are equally impressive, featuring a beautiful swimming pool, private boat dock, and seawall. Located just minutes from premier shopping and dining, and close to Siesta Key’s world-famous white-sand beaches, this is a rare opportunity to own a custom waterfront retreat in one of Sarasota’s most desirable locations. There’s still time for the buyer to personalize this to-be-built home by selecting certain design finishes and features to match their style.
Listing Agent: Kim Ogilvie (941-951-6660)
2417 PARSON LN, SARASOTA, FL 34239
$395,000162 Days on yellowkey MLS ID: A4675748
3 Days Off yellowkey (back on 5/18/2026)
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1316 Built: 1957Monthly Fee: $17 Tax: $5,426 (2025)Community: South GateSingle Family
Taxes:$5,426
Remarks: Don’t miss this adorable SOUTHSIDE ELEMENTARY-zoned gem in hip South Gate! The location could not be more convenient – walk to the Crossings at Siesta Key Mall and less than a mile to the north bridge to Siesta Key itself! For those with school-age children, the close proximity to Brookside Middle School and Southside Elementary zoning are great perks. Completely updated inside with an elegant kitchen (granite, pretty backsplash, stainless appliances), chic wood-look flooring throughout, a charming fireplace, and recently renovated baths, it is move-in ready! Ideally positioned for ultimate convenience to the many amenities of Sarasota, with wonderful possibilities from a full-time or seasonal abode to a prime investment opportunity. The space inside is used really well, with nice spacious bedrooms and a split-bedroom plan, and outside you’ll enjoy a covered screened patio and HUGE fully fenced backyard! There is currently a fun fire pit and open land, so the large yard can be a blank canvas for your outdoor Florida dreams. There is plenty of space for a pool, if that is your desire, or maybe you prefer to plant an edible garden? The choice is yours and this lot can accommodate it all! An oversized 1-car garage with separated extra storage space and laundry completes the package. Easy to show, schedule your visit today!
Listing Agent: Allison Werner (941-961-3212)
4471 TRAILS DR, SARASOTA, FL 34232
$550,00092 Days on yellowkey MLS ID: A4683777
REDUCED by $25,000 (4.3%) on 05/18/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1721 Built: 1987Monthly Fee: $193 Tax: $3,485 (2025)Community: TimberlakesSpa: NoSingle Family
Taxes:$3,485
Elementary School: Brentwood Elementary
Middle School: McIntosh Middle
Remarks: Fresh new price, same incredible lifestyle. Welcome to this beautifully maintained 3-bedroom, 2-bath single-family home in The Lakes, a sought-after community in the heart of Sarasota. Offering 1,721 square feet of comfortable living space, this residence features a thoughtfully designed split-bedroom floor plan that balances privacy with everyday functionality. Enjoy added peace of mind with a 2023 roof and hurricane protection, including impact windows and/or shutters, providing both security and energy efficiency. The spacious living and dining areas flow seamlessly to a screened porch — the perfect spot for morning coffee or relaxing evenings overlooking the private, tree-lined backyard. The serene outdoor setting creates a peaceful retreat with plenty of room to entertain, garden, or simply unwind. Residents of The Lakes enjoy an impressive array of amenities, including one clubhouse and two community pools, tennis and basketball courts, a fitness center, and scenic walking trails. Ideally located in central Sarasota, you’re just minutes from world-class beaches, exceptional dining, premier shopping, and the area’s vibrant cultural attractions.
Listing Agent: Mary Pat Phillips Radford (941-587-9905)
324 SIESTA DR, SARASOTA, FL 34242
$1,400,00019 Days on yellowkey MLS ID: A4692790
0 Days Off yellowkey (back on 5/17/2026)
Bed: 5 Bath: 4.0 Gar: 1 Liv Area Sq Ft: 2510 Built: 1950 Tax: $12,328 (2025)Community: Siesta Rev OfSpa: YesSingle Family
Taxes:$12,328
Remarks: Under contract-accepting backup offers. One or more photo(s) has been virtually staged. Welcome to the #1 beach in the US and top 50 in the world- Siesta Key, FL. Whether you're seeking a primary residence or a high-performing Airbnb investment, this fully renovated 5-bedroom, 4-bathroom coastal contemporary pool home offers the best of both worlds! Ideally situated on an oversized corner lot on Siesta Key and located within city limits, this MOVE-IN READY gem legally qualifies for 7-day minimum rentals, making it a prime opportunity for full-time living, or a lucrative short-term vacation rental. Nestled behind a grand privacy wall, this unique masterpiece provides a true tropical retreat for you and your guests. From the moment you step inside, you'll be captivated by the soaring 12-foot ceilings on both levels, the open concept floor plan, and elegant travertine marble flooring throughout. The primary suite is conveniently located on the first floor, offering both comfort and privacy with French doors that lead to your outdoor private patio. Custom hurricane-impact French doors wrap the entire main living area, seamlessly blending indoor and outdoor spaces, creating a dramatic view of your tropical oasis. Enjoy peace of mind with HURRICANE-IMPACT WINDOWS and DOORS installed throughout the home. Ample on-site parking for up to 4 vehicles adds exceptional convenience for both owners and guests. The chef’s kitchen is fully equipped with high-end finishes, including a gourmet gas range and hood, custom wood cabinetry, quartz countertops, an oversized BLANCO sink, and wine cooler, perfect for hosting and entertaining. Some of the recent upgrades include two brand-new HVAC systems (one for each level), new hot water heater, all new appliances, fresh interior and exterior paint, new landscaping and irrigation, and plumbing complete with a convenient manifold in the garage for your shut off valves. The newly resurfaced pool, paired with new pool equipment, invites you to relax in total serenity. Surrounded by lush, tropical landscaping, the spacious outdoor area offers plenty of room to entertain guests or simply soak in the Florida sunshine in total privacy. This residence is located just four blocks from the nearest beach access at N. Shell Rd, and near the North bridge for convenient access to and from the Key. Take a short ride to the world-famous Siesta Key Beach and Village, where you'll enjoy fine dining, boutique shopping, and vibrant island living. Known for its powder-soft quartz sand, Siesta Key consistently ranks among the top beaches in the United States, making this a premier location for homeowners and investors alike. Call today to schedule your private showing!
Listing Agent: Angela Lista (941-544-6255)
4538 CITATION LN #D, SARASOTA, FL 34233
$269,90089 Days on yellowkey MLS ID: A4684506
REDUCED by $18,000 (6.3%) on 04/28/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1505 Built: 1992 Tax: $3,330 (2025)Community: Calumet At Centergate 1Condo
Taxes:$3,330
Remarks: Under contract-accepting backup offers. This light-filled residence lives like a single-family home and offers soaring vaulted ceilings in every room, creating an open and airy feel throughout. The spacious living, dining, and kitchen areas flow seamlessly together, making everyday living and entertaining effortless. Consistent tile flooring runs throughout the entire home for a clean, cohesive look and easy maintenance. A large, bright, temperature-controlled sunroom overlooks a peaceful garden setting and brings in abundant natural light — the perfect space for morning coffee, reading, or additional living area. Both bedrooms are spaciously sized and feature walk-in closets and private en-suite bathrooms, offering comfort and privacy for owners and guests alike. An attached garage plus additional driveway space provide convenient parking and storage. Set among mature oak trees that canopy the community and frame the front yard, this home offers charm, shade, and a true neighborhood feel. Located just one minute from the Bee Ridge/I-75 corridor, you’ll enjoy quick access to shopping, dining, and daily conveniences, with a straight shot west to the world-renowned Siesta Key beaches and north to UTC. Low-maintenance living, an open layout, and an unbeatable central Sarasota location — this is one you don’t want to miss.
Listing is courtesy of: HARTMAN REAL ESTATE & COMPANY (941-500-4547)
Listing Agent: Zain Hartman (941-735-6415)
225 HOURGLASS WAY #202, SARASOTA, FL 34242
$510,00051 Days on yellowkey MLS ID: A4689015
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1271 Built: 1969Monthly Fee: $1,566 Tax: $5,016 (2025)Community: Whispering SandsCondo
Taxes:$5,016
Remarks: Discover elevated, light-filled coastal living in this beautifully updated 2nd floor residence in the premiere Gulf front property of Whispering Sands! Offered completely TURNKEY FURNISHED. The wonderful OPEN CONCEPT layout flows seamlessly from the kitchen, living and dining spaces into your own private, 34’ south facing lanai—perfect for enjoying sunny mornings, gentle breezes, and relaxed indoor-outdoor living year round. As a bonus, this is a highly desirable end unit, with a wonderful extra window in the living space that invites in abundant natural light, enhancing the open, airy feel throughout. Designed for both style and function, the beautifully REMODELED, kitchen features sleek stone countertops, soothing neutral tile backsplash, an 8’ breakfast bar with seating for 4, stainless Frigidaire and Samsung appliances, soft close cabinetry, and wonderful overhead recessed lighting. Both bathrooms have been tastefully updated with stone counters, while the primary suite offers a private ensuite bath and a walk-in closet for comfortable everyday living. Equally spacious, the guest bedroom is large enough to accommodate two queen beds. Nestled on the westernmost point of Siesta Key, Whispering Sands is a highly desirable 55+ Gulf front community offering resort style living – all ideally just moments away from the colorful boutiques, dining options, and charm of world famous Siesta Key Village. The complex offers 800’ of PRIVATE quartz sand beach on the sparkling Gulf, 2 heated pools, new beachside grills and Tiki Hut, shuffleboard, and canoe/kayak storage, The main clubhouse – just steps from this unit - is currently undergoing complete remodeling and upon completion will include fitness rooms, a full catering kitchen, large screen TV, and an elegant, comfortable space for social events or private entertaining. Effortless island living starts here. Don’t miss this opportunity to own this move-in ready, coastal escape in an exceptional island setting!
Listing Agent: Harriet Stopher (404-316-8944)
4034 ROBERTS POINT RD, SARASOTA, FL 34242
$8,500,00018 Days on yellowkey MLS ID: A4693305
Bed: 5 Bath: 4.5 Gar: 6 Liv Area Sq Ft: 5458 Built: 1990 Tax: $52,899 (2025)Community: Elliot M Prop Siesta KeySpa: YesSingle Family
Taxes:$52,899
Remarks: A rare offering on the exclusive enclave of Roberts Point Road, this fully remodeled in 2023 waterfront estate embodies refined coastal luxury, encompassing 5,458 square feet with 5 bedrooms, 4 full bathrooms, and 1 half bath. Showcasing water frontage on both the front and rear with direct, no-bridge access to Sarasota Bay, the home is set on a private 0.64-acre homesite. The property features a brand-new seawall and two exclusive dock settings, including a 16,000 lb boat lift and jet ski lift, along with a private waterfront seating area designed for effortless enjoyment of the serene surroundings. Underground utilities preserve uninterrupted water views, while soaring ceilings and a signature eagle’s nest vantage point elevate the home’s architectural presence and capture breathtaking vistas. Inside, the residence has been masterfully transformed with a refined open-concept design, anchored by a fully redesigned chef’s kitchen featuring Sub-Zero refrigeration, a gas range, new appliances and countertops, and exceptional craftsmanship throughout. Custom millwork, designer lighting, shiplap detailing, and elegant new railings define the home’s modern coastal aesthetic. The thoughtfully designed floor plan offers three distinct kitchen spaces—including a main kitchen, outdoor kitchen, and private guest suite kitchen—along with a private-entry guest residence and a versatile ground-floor loft with dual Murphy beds, providing exceptional flexibility for both everyday living and elevated entertaining. A private elevator services the home, while a new glass front entry door—currently being installed—further enhances its modern coastal presentation. Curated for both comfort and performance, the home is equipped with three new AC systems, a new well, enhanced irrigation and landscaping, a whole-home Generac generator, reverse osmosis and Kinetico water systems, and full smart home integration through Control4 automation, Sonos audio, and a high-end AV infrastructure. Outdoors, a resort-style pool and spa with both gas and electric heating and full app-based control ensure year-round enjoyment. Additional features include a six-car garage with epoxy floors, a bespoke outdoor bar and kitchen, screened enclosure, kayak storage, and a private sand area—culminating in a truly turnkey, design-forward waterfront estate in one of Sarasota’s most coveted locations.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
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