Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
3424 OLD OAK DR, SARASOTA, FL 34239
$1,195,00014 Days on yellowkey MLS ID: A4688216
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1368 Built: 1953 Tax: $10,828 (2025)Community: Shoreland WoodsSpa: NoSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$10,828
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Craving a low-maintenance, island-inspired lifestyle just moments from sparkling open water, world-famous beaches, and Sarasota’s most coveted destinations? This quaint Florida bungalow located in west of trail delivers the perfect blend of charm, location, and effortless living—just minutes to Siesta Key and steps from the coastal lifestyle you’ve been dreaming of. Tucked away in one of Sarasota’s most desirable “West of the Trail” neighborhoods, 3424 Old Oak Dr has been thoughtfully redesigned to preserve its original character while introducing timeless, modern updates. From the moment you arrive, the lush tropical landscaping, winding garden paths, and private courtyard-style entry create a warm, inviting ambiance that feels like your own hidden oasis. Inside, the home showcases a light-filled, airy design highlighted by vaulted wood-beam ceilings, soft coastal tones, and an open-concept layout that seamlessly blends comfort and style. The beautifully updated kitchen features granite countertops, open shelving, stainless steel appliances, and designer finishes, creating a space that is both functional and visually stunning. The living area centers around a charming wood-burning fireplace, adding warmth and character, while French doors invite natural light and connect indoor and outdoor living spaces effortlessly. The home offers flexible living spaces ideal for a primary residence, seasonal retreat, or income-producing property. Each room reflects a curated, coastal aesthetic with tasteful updates while maintaining the home’s unique bungalow charm. Step outside to your private backyard sanctuary, where a screened-in heated pool is surrounded by mature tropical landscaping, creating a serene and secluded environment perfect for relaxing or entertaining. An outdoor shower adds to the coastal lifestyle experience, while multiple seating areas and garden spaces enhance the home’s tranquil, resort-like feel. Located just minutes from Siesta Key Beach, Southside Village, downtown Sarasota, Sarasota Memorial Hospital, and top-rated dining and shopping, this home offers unmatched convenience paired with a laid-back coastal lifestyle. Rarely does a property combine location, charm, income potential, and lifestyle so seamlessly. This is your opportunity to own a truly special Sarasota bungalow where every day feels like a vacation.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Adnan Dedic (941-726-2917)
7253 MEADOWSHADE CT, SARASOTA, FL 34241
$774,99068 Days on yellowkey MLS ID: TB8473144
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2697 Built: 2026Monthly Fee: $160 Tax: $8,259 (2026)Community: Lakeview CrossingSingle Family
Taxes:$8,259
Elementary School: Lakeview Elementary
Tax Year: 2026
Middle School: Sarasota Middle
Remarks: Under Construction. Welcome home to The Wagoner, by David Weekley homes, in the brand-new, suburban lifestyle community of Lakeview Crossing in Sarasota. This single-story home sits peacefully on a pond where you can imagine coming home to serene views with sightlines of the pond from the moment you walk in the front door. Once inside, you’ll notice the thoughtfully designed open concept, flooded with natural light and a designer kitchen that will make hosting gatherings a must. The coastal interior design selections make you feel like you're just steps away from the beach. The owner’s retreat is situated off the back of the home, split from the other bedrooms, so you will have your own private oasis to wind down in. In addition to the 4 bedrooms, there is a dedicated den with French doors giving you flexible options with how to use the extra space. The 3-car tandem garage gives you plenty of storage and space to park all your vehicles, and the dedicated indoor utility room allows you to never break a sweat when doing laundry. Enjoy your morning coffee or evening glass of wine out back on your extended lanai or even on the spacious front porch where you can watch the kids play. Also, you are conveniently located close to downtown Sarasota (10 miles), UTC shopping center (9.4 miles), Siesta Key Beach (12 miles) & SQR airport (15 miles). Enjoy peace of mind knowing your home is constructed by the award winning builder of David Weekley Homes with energy efficiency in mind.
Listing is courtesy of: WEEKLEY HOMES REALTY COMPANY (866-493-3553)
Listing Agent: Robert St. Pierre
6821 CHLOE CT, SARASOTA, FL 34241
$664,99032 Days on yellowkey MLS ID: TB8486434
REDUCED by $35,000 (5.0%) on 04/09/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2627 Built: 2026Monthly Fee: $160 Tax: $6,217 (2026)Community: Lakeview CrossingSingle Family
Taxes:$6,217
Remarks: Under Construction. You’ll be delighted by the attention to detail and expert design of The Hemphill, 2-story floor plan by David Weekley Homes in the brand new, suburban lifestyle community of Lakeview Crossing in Sarasota. Open-concept family and dining spaces showcase our LifeDesign? refinements that grant this floor plan exceptional style and livability. This home offers 3 bedrooms, 2 full baths, 1 half bath, a study, upstairs retreat and a 3-car tandem garage. Prepare, present and enjoy your culinary masterpieces on the designer kitchen center island overlooking the open gathering spaces. Pamper yourself in the spa-inspired Owner’s Bath and explore the wardrobe potential of the large walk-in closet before retiring to the lovely first floor Owner’s Retreat. Also on the first level, you'll find the office with french doors as well as a convenient powder room and indoor laundry. Make your way upstairs to privacy and personality, making each extra bedroom and the retreat a great place to thrive. In the fully gated community of Lakeview Crossing, you are conveniently located close to downtown Sarasota (10 miles), UTC shopping center (9.4 miles), Siesta Key Beach (12 miles) & SQR airport (15 miles). Come see what quality construction and thoughtful design looks like for yourself and make this David Weekly Home yours today.
7758 SILVER BELL DR, SARASOTA, FL 34241
$895,000Listed 04/14/2026 11:53AM MLS ID: A4689138
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3012 Built: 1989Monthly Fee: $147 Tax: $5,381 (2025)Community: Bent Tree VillageSingle Family
Taxes:$5,381
Remarks: Don't let this one get away! * LOCATION, LOCATION, LOCATION * Rarely available in the GATED community of The Woodlands of Bent Tree * This EXQUISITE EXECUTIVE FAMILY HOME BOASTS A VERY PRIVATE SETTING ON ALMOST 3/4 ACRE, BACKING TO A WOODED GREENBELT * Quiet cul de sac location which means no through traffic * Side-load OVERSIZED 2 Car Garage * Quality Built by Arthur Rutenberg Homes and IMPECCABLY MAINTAINED BY THE ORIGINAL OWNERS, you will not find a home with this QUALITY & PRIDE OF OWNERSHIP * 4 Bedrooms & 3 Full Baths * 2 Bedrooms are En-suites * Formal Living Room & Formal Dining Room * The THOUGHTFULLY REIMAGINED Chef's Kitchen is open to the Family Room with a Wood-burning Fireplace * The generously-sized Owners' Suite showcases a Spa-style Bath with Walk-in Closet, Dual Sinks, Shower and a Garden Tub * All of this wraps your PRIVATE OUTDOOR OASIS with a CAGED POOL & SPACIOUS COVERED LANAI * This is the perfect home to entertain family & friends or for just relaxing in your slice of paradise * 'A' RATED SCHOOL DISTRICT * Short 15 minute drive to World Famous Siesta Key Beach as well as UTC Mall * You are close to all of Sarasota's fabulous amenities * One look & you'll fall in love! *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Ryan Brown (941-330-7774)
6829 CHLOE CT, SARASOTA, FL 34241
$699,99029 Days on yellowkey MLS ID: TB8487039
REDUCED by $30,000 (4.1%) on 04/09/2026
Bed: 5 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2908 Built: 2026Monthly Fee: $160 Tax: $6,217 (2026)Community: Lakeview CrossingSingle Family
Remarks: Under Construction. Imagine your future with the timeless comforts and top-quality construction you’ll experience in The Messner floor plan by David Weekley Homes brand new, suburban lifestyle community of Lakeview Crossing in Sarasota. There’s a room for everyone in this 5 bedroom, 3.5 bath, 2 car garage luxury home. Expertly placed energy-efficient windows help the family and dining spaces shine with natural light. The streamlined designer kitchen creates an easy culinary layout for the resident chef while granting an open view of the adjacent living spaces. Head up stairs to find the Owner’s retreat, an en suite Owner’s Bath and sizable walk-in closet to contribute to the everyday getaway. You’ll also find a multipurpose loft for a family movie theater or game night HQ as well as 3 additional bedrooms, 1 full bath and your indoor laundry room conveniently located on the second floor. Finishing out the first floor is your guest bedroom with en-suite bath so your visitors have their own getaway, as well as a study and powder room. The generous back yard boasts plenty of room to build your outdoor, pool inspired oasis. How do you imagine your #LivingWeekley experience with this new home in Lakeview Crossing? You are conveniently located close to downtown Sarasota (10 miles), UTC shopping center (9.4 miles), Siesta Key Beach (12 miles) & SQR airport (15 miles) in the fully gated community of Lakeview Crossing.
5316 ALTOONA ST, SARASOTA, FL 34232
$499,900187 Days on yellowkey MLS ID: O6349173
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1842 Built: 2025 Tax: $901 (2024)Community: BroadwaySingle Family
Taxes:$901
Elementary School: Fruitville Elementary
Tax Year: 2024
Middle School: McIntosh Middle
Remarks: One of the most impressive homes in the neighborhood, built by Endura Construction, this home features impact-resistant windows and doors, a storm-ready structure built to current codes, and a builder’s warranty, providing superior protection and peace of mind. Inside, you’ll find three spacious bedrooms and two elegantly designed bathrooms, including a bright and sophisticated primary suite with a large walk-in closet. The open-concept layout connects the kitchen, dining, and living areas, offering a stylish and functional setting for everyday living or entertaining. Sliding glass doors lead to a generous covered lanai, perfect for enjoying Florida’s indoor-outdoor lifestyle. A rare perk: no HOA. This means no monthly dues, no surprise assessments, more predictable costs, and no evolving community rules that could impact your lifestyle—a level of freedom that many buyers value highly. Ideally situated just minutes from University Town Center (UTC Mall), Nathan Benderson Park, Whole Foods, SRQ Airport, and an array of upscale dining and shopping, this home offers unmatched convenience in a premier Sarasota location. Closing cost assistance is available with the preferred lender. Don’t miss your chance to own this stunning, storm-ready modern home in the heart of Sarasota’s most vibrant area. Schedule your private tour today.
Listing is courtesy of: NOBSKA REAL ESTATE LLC (689-276-1593)
Listing Agent: Laura Teixeira, Pa (941-962-2413)
5215 HIDDEN HARBOR RD, SARASOTA, FL 34242
$7,900,000145 Days on yellowkey MLS ID: A4669367
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 4863 Built: 2025Monthly Fee: $247 Tax: $22,047 (2024)Community: Hidden HarborSpa: YesSingle Family
Taxes:$22,047
Elementary School: Phillippi Shores Elementary
Remarks: One or more photo(s) has been virtually staged. Under Construction. This brand-new waterfront estate is being brought to life by Dynan Construction, Sarasota’s premier local luxury builder celebrated for impeccable craftsmanship, architectural integrity, and enduring coastal design. Built to the Fortified Gold Standard, the residence is engineered for long-term resilience against Florida’s coastal elements while embodying the artistry and refinement that define Dynan’s signature builds. Interiors are curated by acclaimed designer Annalise O’Brien, ensuring every space reflects elevated taste and timeless sophistication. This 5-bedroom estate features 5 full baths plus a dedicated pool bath and powder bath, offering a rare combination of durability, modern design, and everyday luxury. An attached guest quarters is the perfect setup for multigenerational living, extended guests, or a private studio/workspace. Located in the exclusive Hidden Harbor community—an enclave known for its mature landscaping and lush tropical canopy streets—this property sits on a deep-water canal with direct access to Sarasota Bay and the Gulf of Mexico. Designed for effortless coastal living, the home is equipped with smart-house lighting controls and is prewired for security, cameras, and full indoor/outdoor surround sound. The home is also prepared for a future whole-house generator installation, offering peace of mind for year-round living. Expansive 10-foot sliders frame the waterfront views and create a seamless flow between the interior and exterior spaces. Outside, the resort-style pool and spa, integrated pergola, and fully equipped outdoor kitchen provide an exceptional extension of daily living and entertaining. Inside, each room showcases curated designer selections, elevated finishes, and thoughtful details throughout. A spacious 3-car garage offers ample room for vehicles, storage, and recreational equipment. Just A short bike ride from the world-renowned Siesta Key —this home captures the essence of Sarasota’s coastal lifestyle with unmatched convenience to beaches, dining, and local amenities.
Listing is courtesy of: COASTAL RESERVE (941-586-7736)
Listing Agent: Cassandra Miller (941-586-7736)
111 S PINEAPPLE AVE #806, SARASOTA, FL 34236
$1,845,00018 Days on yellowkey MLS ID: A4687850
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1891 Built: 2019 Tax: $12,679 (2025)Community: Mark Sarasota CondoCondo
Taxes:$12,679
Middle School: Booker Middle
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)
111 S PINEAPPLE AVE #1021, SARASOTA, FL 34236
$1,299,0006 Days on yellowkey MLS ID: A4688715
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1575 Built: 2019 Tax: $18,357 (2025)Community: Mark Sarasota CondoSpa: YesCondo
Taxes:$18,357
Remarks: Experience refined urban living in this beautifully updated residence, complete with two dedicated parking spaces, featuring two bedrooms, 2.5 baths, and a versatile bonus room. Thoughtfully designed with an open concept layout, the home seamlessly blends modern style and everyday functionality, enhanced by high end builder finishes and custom upgrades throughout. The flexible den, ideal as a library, media room, or home office, offers endless possibilities. At the heart of the home, the gourmet kitchen impresses with an induction cooktop, quartz countertops, custom backsplash, and under cabinet lighting, perfect for both everyday living and entertaining. The spacious owner’s suite serves as a private retreat, featuring direct terrace access, a large walk in closet, additional custom storage, and a spa inspired bathroom with dual vanities, an oversized countertop, and a glass enclosed walk in shower with a rain showerhead. Each bedroom includes its own en suite bath, and the additional half bath is both stylish and convenient for guests. Storage is thoughtfully maximized with custom built closets, cabinetry, and shelving throughout. Luxury upgrades include porcelain flooring, designer light fixtures, premium wireless ceiling fans, an Ecobee smart thermostat, and remote controlled Hunter Douglas window treatments. Residents also benefit from community EV charging stations. The expansive terrace offers ample room for outdoor dining and lounging, with sweeping views of downtown Sarasota and the bay, perfect for taking in stunning sunsets. Residents of The Mark enjoy exceptional amenities, including a stylish club room and lounge, a state of the art fitness center, and an outdoor entertaining area with grilling stations, fire pit, and a 65 foot heated saltwater pool and spa. Located in the heart of downtown Sarasota’s vibrant arts and dining district, the building offers 24 hour security and on site management. Built in 2019, The Mark is known for its sleek contemporary design and premier location just steps from Main Street’s boutiques, restaurants, and popular farmers market. Schedule your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Mairead Smialek (847-334-4848)
656 TROPICAL CIR, SARASOTA, FL 34242
$4,195,000130 Days on yellowkey MLS ID: A4674326
Bed: 4 Bath: 5.0 Gar: 3 Liv Area Sq Ft: 5238 Built: 2025Monthly Fee: $54 Tax: $8,623 (2024)Community: Siesta BeachSpa: YesSingle Family
Taxes:$8,623
Remarks: Perfectly positioned in Siesta Beach—just moments from the shoreline—this newly completed 2025 coastal residence delivers a rare combination of striking design, thoughtful functionality, and luxurious indoor-outdoor living. Spanning more than 5,200 square feet of air-conditioned space across two levels, this contemporary home has been professionally staged with high-end furnishings included in the sale, making it truly move-in ready. The elevated architectural facade creates a commanding first impression. Step inside to an expansive great room with wood flooring, soaring coffered ceilings, crown molding, and a dramatic wood-paneled accent wall that anchors the living and dining spaces. Walls of pocketing impact-rated sliders dissolve the boundaries between indoors and out, opening to a resort-style entertaining area. A built-in wet bar with wine cooler enhances the home’s hospitality appeal. The gourmet chef’s kitchen sits at the heart of the first floor, designed to showcase the outdoor views. Outfitted with quartz countertops, sleek shaker cabinetry, hidden appliances, a gas Wolf stove with dual ovens, walk-in pantry, and an oversized island, the kitchen is ideal for everyday use and large-scale gatherings. Adjacent formal dining space is framed by oversized windows, creating a sun-lit setting for memorable meals. Outdoor living unfolds on a spacious covered patio featuring a tongue-and-groove ceiling treatment, summer kitchen with built-in gas grill, lounge and dining areas, and a heated pool and spa surrounded by beautifully landscaped grounds. The primary suite—secluded on the main level—offers vaulted ceilings, dual walk-in closets, and a spa-inspired bath finished with quartz surfaces, stone-clad shower, and refined detailing. A dedicated office, first-floor laundry room, and a pre-planned shaft for a future elevator provide convenience and flexibility. Upstairs, three additional bedroom suites each feature walk-in closets and en-suite baths. A study with generous storage, a media room, a bonus room, and a secondary laundry room complete the second level. A 45-foot balcony connects multiple rooms and overlooks the pool and tropical landscaping. The split three-car garage provides ample storage for vehicles, recreation gear, and coastal living essentials. Situated in the coveted Siesta Beach neighborhood, the home offers a quiet residential setting just minutes from award-winning Siesta Key Beach, world-renowned for its quartz-sand shoreline and turquoise water. Explore Siesta Village for dining and boutique shopping, enjoy boating and kayaking along the Intracoastal Waterway, or venture over the bridge to Sarasota’s vibrant cultural scene—The Bay Park, Ringling Museum, Van Wezel Performing Arts Hall, Marina Jack, Selby Gardens, and the city’s acclaimed restaurants and galleries. This newly constructed coastal estate delivers the perfect blend of design excellence, modern comfort, and proximity to everything that defines the Siesta Key lifestyle.
Listing Agent: Roger Pettingell (941-387-1840)
3300 BENEVA #214, SARASOTA, FL 34232
$199,99974 Days on yellowkey MLS ID: O6371947
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1084 Built: 1980 Tax: $2,279 (2025)Community: Fairways & GreensCondo
Taxes:$2,279
Elementary School: Wilkinson Elementary
Remarks: Incredible investment to own 2-bedroom, 2-bath condominium located in the highly desirable Fairways & Greens Condo community. Situated on the first floor, this residence welcomes you with an open and functional floor plan designed for comfortable everyday living and easy entertaining. The well-sized kitchen features stainless steel appliances and flows seamlessly into the dining and living areas, creating a bright and inviting space. The primary bedroom offers direct access to the enclosed patio, where you can enjoy peaceful views of the community pool and beautifully landscaped surroundings. A generously sized second bedroom provides ample natural light, ideal for guests, a home office, or flexible living arrangements. The home also includes a second full bathroom and a convenient laundry closet with washer and dryer. Unit 214 includes one assigned covered parking space, along with ample guest parking. Enjoy a prime central Sarasota location, just 0.2 miles from Publix, 3 miles from Sarasota Memorial Hospital, and only 5.5 miles from the world-renowned Siesta Key Beach. Nearby attractions include Arlington Park (2.5 miles), Downtown Sarasota (4 miles), Legacy Trail access (2.2 miles), Walmart Neighborhood Market (0.9 miles), Starbucks (1.2 miles), and Westfield Siesta Key (2.5 miles). Commuting is effortless with US-41 just 2 miles away and I-75 only 3.8 miles away. Whether you’re seeking a primary residence, seasonal retreat, or investment opportunity, this home offers comfort, convenience, and an unbeatable Sarasota lifestyle. Schedule your private showing today and experience it for yourself.
1444 HARBOR DR, SARASOTA, FL 34239
$6,999,95060 Days on yellowkey MLS ID: O6375298
REDUCED by $500,050 (6.7%) on 04/14/2026
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 5001 Built: 2002 Tax: $33,037 (2025)Community: Harbor Acres Sec 2Spa: YesSingle Family
Taxes:$33,037
Remarks: Location, Location, Location. Welcome to an exceptional waterfront residence in the heart of Harbor Acres, where refined design meets the ultimate Florida lifestyle. This expansive 5,000+ square foot estate offers breathtaking sunset views over a private waterfront basin with direct access to Sarasota Bay—an idyllic setting for both everyday living and elegant entertaining. A private waterfront retreat, this five-bedroom, five full and two half bath home is thoughtfully designed to maximize comfort and flexibility. Enjoy a heated in-ground pool and spa, deep-water dock with boat lift, and ample space for a large vessel—perfect for boating enthusiasts seeking seamless access to Sarasota’s pristine waterways. The home features two primary suites, one on each level. The first-floor suite offers private garage access and is ideal for in-law accommodations, guests, or multigenerational living. Additional bedrooms can easily adapt to home offices, a fitness studio, or creative spaces to suit modern lifestyles. Multiple electric fireplaces enhance the ambiance in the primary suites, living room, and family room. An interior elevator provides effortless access between floors. The gourmet kitchen is designed for entertaining, showcasing granite and quartz countertops, a wet bar, a wine cooler, and a generous breakfast bar that opens seamlessly to the family room. The outdoor living spaces feature covered lanais on both levels overlooking the pool and bay, surrounded by tropical landscaping. A covered outdoor dining area includes a summer sink and dedicated pool bath, creating an ideal setting for entertaining or relaxing in total privacy. Move-in ready. This meticulously maintained home offers peace of mind and modern efficiency. Three new AC and HVAC systems (2024), two new gas water heaters, a variable-speed Jandy pool pump, new seawall cap, 22KW Generac generator, over $50,000 in recent upgrades. Prime Location, ideally located to Southside Village, residents enjoy easy access to acclaimed dining, boutique shopping, and Morton’s Gourmet Market. Hospitals, medical offices, banks, and essential services are all conveniently nearby—delivering both luxury and everyday convenience. This remarkable residence offers an unparalleled combination of waterfront luxury, thoughtful design, and walkable convenience. A rare opportunity to experience the best of Sarasota living.
Listing is courtesy of: HOUWZER INC (267-765-2080)
Listing Agent: Daniel Robinson (407-907-5501)
8911 MIDNIGHT PASS RD #208, SARASOTA, FL 34242
$635,00096 Days on yellowkey MLS ID: A4677015
1 Days Off yellowkey (back on 3/13/2026)
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1415 Built: 1973 Tax: $6,230 (2025)Community: Sunrise Cove Sec 2Condo
Taxes:$6,230
Remarks: Welcome to Sunrise Cove and the coveted and quiet south end of Siesta Key. This DIRECT BAYFRONT condo is a 3 BEDROOM CONDO and is directly across the road from TURTLE BEACH with plenty of PUBLIC BEACH ACCESS. This condo unit was re-configured and now has three full bedrooms and two full bathrooms. Features include new interior paint, opened and central kitchen, split bedroom floor plan, washer/dryer inside unit, and it comes completely furnished. The open kitchen features a solid beadboard cabinetry, pantry, and plenty of storage. This is an end unit with end unit windows in two of the bedrooms for added light. Relax and look directly out onto Little Sarasota Bay and enjoy wildlife, dolphins, and manatees as well as beautiful sunrises! This condo is super clean and ready to go! There is a storage closet down the hall for beach items and monthly rentals are allowed plus one brand-new carport is included! SUNRISE COVE features 49 boat slips with vacancies, two heated swimming pools, pickleball, tennis, clubhouse with clubroom, fitness room, billiards/ping pong, kayak storage, BBQ grill with gazebo, and public beach access directly across the street! This is a super well-run and manicured complex and is very near to two delicious restaurants. This south end of Siesta Key is very quiet. Come see this beautiful beach and waterfront condo today!
Listing Agent: Joe Cleary (941-650-8485)
0 ROBERTS POINT CIR #LOT 17, SARASOTA, FL 34242
$3,400,000170 Days on yellowkey MLS ID: A4669772
Bed: 5 Bath: 5.5 Gar: 4 Liv Area Sq Ft: 3200 Built: 2027 Tax: $5,916 (2024)Community: Roberts Point 2Spa: YesSingle Family
Taxes:$5,916
Remarks: Pre-Construction. To be built. Brought to you by Noah Thomas Builders, this newly constructed coastal residence inspired by classic West Indies architecture and situated in the exclusive Roberts Point neighborhood on Siesta Key. This thoughtfully designed home pairs timeless island style with modern coastal construction, offering refined living in a highly desirable island setting. Built to meet today’s highest coastal standards, the residence will feature solid concrete block construction, elevated foundation systems, hurricane-impact windows and doors, metal roofing, and other structural elements designed for durability and long-term peace of mind in a waterfront-adjacent environment. The interior layout emphasizes open, airy living spaces with high ceilings with abundant natural light that create an effortless connection to the outdoors. The kitchen is designed as both a functional workspace and gathering area, featuring premium appliances, custom cabinetry, and a generous island ideal for entertaining and everyday living. The primary suite serves as a private retreat with a spa-inspired bathroom, including a freestanding soaking tub, dual vanities, and a spacious walk-in shower. Additional bedrooms offer en-suite baths and refined finishes, while a flexible bonus space allows for a home office, fitness room, or lounge. Outdoor living is a focal point of the design, with covered entertaining areas, an outdoor kitchen, and a resort-style pool and spa—perfect for enjoying Siesta Key’s year-round sunshine and relaxed island atmosphere. Located on the quiet north end of Siesta Key, Roberts Point is known for its privacy, natural surroundings, and convenient proximity to Siesta Beach, Siesta Village, and downtown Sarasota. This new construction home presents a rare opportunity to experience elevated coastal living by Noah Thomas Builders in one of Sarasota’s most coveted island communities. All images, renderings, and descriptions are for illustrative purposes and represent the intended design and style by Noah Thomas Builders. Finishes, materials, and specifications are subject to change during construction. Pricing, availability, and final details may be modified prior to completion.
Listing is courtesy of: 1ST CLASS REAL ESTATE SUNCOAST (386-882-6644)
Listing Agent: Holly Wikfors, Llc (239-777-8075)
1647 SIESTA DR, SARASOTA, FL 34239
$1,690,000Listed 04/14/2026 10:41AM MLS ID: A4689949
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3032 Built: 2025 Tax: $17,778 (2025)Community: BayviewSpa: YesSingle Family
Taxes:$17,778
Remarks: Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms with modification add-on with the builder. From the moment you enter, you'll be captivated by the open floor plan, pool view, and fantastic design. This dazzling property, boasts an open floor plan that features high ceilings, natural light, and high-quality finishes throughout. The home features a modern and elegant kitchen with top-of-the-line Cafe' appliances, quartz countertops, and custom cabinetry. The primary bedroom located on the upper level can be accessed by elevator is a true sanctuary, offering a plush and peaceful retreat. It boasts vaulted ceilings, en-suite bathroom that includes a soaking tub and a separate shower that's great for unwinding after a long day. The room also features a generously sized walk-in closet with abundant space for storage and organization as well as a private terrace. On the second floor you will find three vast bedrooms, with plenty of closet space for added convenience and comfort. One of the most notable features of the second floor is the sizable sundeck and balcony, which are attached to both bedrooms. The laundry room is conveniently located on the second floor as well. The spacious bonus room offers endless possibilities, from an office, den, playroom, media center, or a home gym. This home has two patios with an outdoor area with a large pool and hot tub that seamlessly blend the indoor and outdoor living with meticulously planned landscaping. Situated between Siesta Key and Downtown Sarasota, you will have easy access to some of the best beaches, restaurants, and shopping in the area. Whether you are looking for a day at the beach, a night out on the town, or a quiet evening at home, this home has everything you need.
Listing is courtesy of: THE STUTZMAN REALTY GROUP, LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
4922 COMMONWEALTH DR, SARASOTA, FL 34242
$1,795,000200 Days on yellowkey MLS ID: A4666313
4 Days Off yellowkey (back on 4/14/2026)
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2767 Built: 1995 Tax: $6,523 (2025)Community: Siesta BeachSpa: NoSingle Family
Taxes:$6,523
Remarks: Welcome your Siesta Key dream home Commonwealth Drive, a stunning custom residence located directly on the Grand Canal. This four bedroom, four bathroom home exudes island style and warmth from the moment you see it. The Key West style build has a concrete base level, hardy plank cement siding, and a standing seam metal roof. The main living areas all give way to sunny and palm-lined views of pool deck with saltwater canal in the background. The open living areas on the main level feature hardwood flooring, a gas built-in fireplace, built-in shelving, and lots of windows to enjoy the view. The primary suite features lots of space, dual walk-in and an upper level balcony with incredible views. There’s a second larger suite with sitting area to make guests feel at home, and two more bedrooms for the ultimate in flexibility. This home is truly all about the location- want to go paddleboarding or out on your kayaks? Right in the back yard. The beach is just a few blocks away and the northern Siesta Key location gives easy access to downtown Sarasota and beyond. If you’re looking for the perfect combination of space, privacy, convenience, and of course a little sand between your toes- this may be the perfect home for you. Boaters will also love this Grand Canal location, with only one large fixed bridge and easy access to Sarasota Bay. Don’t hesitate, schedule your showing of this fine home today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Drew Russell (941-993-3739)
5880 MIDNIGHT PASS RD #206, SARASOTA, FL 34242
$1,335,000179 Days on yellowkey MLS ID: A4668223
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1642 Built: 1982 Tax: $10,871 (2025)Community: CasarinaCondo
Taxes:$10,871
Remarks: Find your beach get-away in this remodeled three-bedroom Casarina condo located on Siesta Key’s famous Crescent Beach. This stunning TURNKEY FURNISHED and updated unit includes an open concept kitchen with high-end custom soft-close cabinetry, designer hardware and granite countertops. The great room was extended to incorporate the balcony into the living space creating an open and airy feeling to this home. A wall mounted television with Sonos audio provides family entertainment. The spacious primary bedroom with a Closet Tech designed walk-in closet opens to a large bathroom with custom cabinets, dual sinks and large walk-in shower. A third bedroom was created during the recent remodel and includes a built-in under window desk. The full-sized laundry room allows for plenty of storage. Luxury vinyl flooring was installed in 2020 in all public rooms. Impact windows were added in 2016. Electric blinds can close off the sliding glass doors to the outside view while all other windows have custom designed plantation shutters. Crown molding and solid wood doors are found throughout the unit. Casarina is an 89-unit condominium complex that sits on 200 feet of private beach and encompasses 7 acres of tropical landscaping. The complex has a clubhouse with kitchen. Spend your days enjoying the beachside pool and spa, play a game of pickleball on one of the two lighted tennis courts, or relax on the island’s famous crystal sand beach. Hop on the free trolley to enjoy the dining, shopping and entertainment at Siesta Key Village. CASARINA ALLOWS OWNERS ONE SMALL PET.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Suki Scollo (941-587-2289)
5047 VINSON WAY, SARASOTA, FL 34232
$549,000Listed 04/14/2026 10:56AM MLS ID: A4689767
Bed: 4 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 1980 Tax: $4,521 (2025)Community: Brentwood EstatesSpa: YesApartment
Taxes:$4,521
Elementary School: Brentwood Elementary
Remarks: High-performing income property delivering a 9.8% cap rate in a prime Sarasota location—this is the type of asset investors actively seek. 5047 Vinson Way is a fully operational, income-generating property configured into three distinct units, offering immediate cash flow and maximum flexibility. The layout includes a 2-bedroom, 1-bath primary residence, plus two additional rental units—a studio and a one-bedroom—both currently utilized for short-term rental income. This is a true turnkey investment—all furniture is included in the sale, allowing a seamless transition for the next owner to continue operating without interruption or additional setup costs. The property is optimized for performance. Live in the main unit while the other units generate income, or maximize returns by operating all three as short-term rentals. Strong rental demand in the area supports consistent occupancy and revenue potential. A standout feature is the brand-new pool and spa, enhancing guest appeal and driving higher nightly rates—an essential component in maximizing ROI. Ideally located near Sarasota’s top attractions, dining, shopping, and world-renowned beaches, this property offers the perfect balance of lifestyle and income. Turnkey, furnished, income-producing, and delivering strong returns—this is not just a property, it’s a high-performing asset.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Mariele Hoffman (941-225-0800)
800 HUDSON AVE #106, SARASOTA, FL 34236
$625,000127 Days on yellowkey MLS ID: A4673881
REDUCED by $25,000 (3.8%) on 04/14/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1562 Built: 1984 Tax: $3,605 (2024)Community: Hudson HarbourCondo
Taxes:$3,605
Remarks: Unbeatable value and location in downtown Sarasota. This 3-bedroom,3 full bath residence lives more like a townhome than a condo. No elevators, park right in front of your front door and walk out to the pool. Ideally located across from Selby Gardens and only one block from Sarasota Bay. Hudson Harbour is not in the AE flood zone, has covered parking and is pet-friendly, allowing one small dog and multiple cats. The three versatile bedrooms in this residence provide exceptional flexibility. The first-floor bedroom & bath can serve as a convenient primary suite, while the second-floor option offers additional privacy—ideal for guests, family, hobbies, or a home office. Enjoy two private balcony lanais overlooking a lush tropical garden and tranquil fountain, creating the perfect setting for morning coffee or relaxing evenings. Inside, the home features light soft neutral tones complemented by neutral tile flooring and elegant crown molding throughout. The thoughtfully designed kitchen includes a spacious eat-in dining area and breakfast bar that opens seamlessly to the living and dining spaces—perfect for everyday living and entertaining. Numerous updates have been completed over the years, including: Brand-new AC (2024), New windows and sliding glass doors, renovated bathrooms, updated kitchen appliances, New washer and dryer, Water heater replacement and fresh interior paint. Hudson Harbour offers a private downtown, intimate tropical setting with only 18 units centered around a heated community pool. Living here places you within walking distance to the Sarasota Bayfront Park for nightly sunsets, a boat cruise or waterfront dining and of course all of Sarasota’s downtown restaurant and theater options. Outdoor lovers will appreciate easy access to Legacy Trail, Payne Park and Lido Beach. Take the free downtown trolley to St. Armands Circle and Lido Beach. Schedule a showing and don’t miss this best priced Downtown Sarasota residence on the market today !
Listing Agent: Maureen Doherty (941-993-3159)
$549,000Listed 04/14/2026 10:57AM MLS ID: A4689764
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 1960 Built: 1980 Tax: $4,521 (2025)Community: Brentwood EstatesSpa: YesSingle Family
Remarks: Exceptional income-producing turnkey opportunity in the heart of Sarasota with a 9.8% cap rate! This versatile property at 5047 Vinson Way is ideal for both investors and owner-occupants looking to maximize returns while enjoying a primary residence. The property is thoughtfully configured into three separate units: a spacious 2-bedroom, 1-bath main residence perfect for an owner, plus two additional income-generating units—a studio and a one-bedroom—both currently operating as successful short-term rentals. The outdoor space is a true standout, featuring a brand-new pool and spa, creating a resort-style experience that significantly enhances rental appeal and guest satisfaction. Each unit offers privacy and functionality, making it ideal for Airbnb or extended stays. Whether you’re house hacking or running a full investment property, this setup delivers immediate income potential and strong cash flow. Located in a desirable Sarasota area close to shopping, dining, and world-famous beaches, this property blends lifestyle and performance seamlessly. Live in one unit, rent the others, and capitalize on a high-performing asset—opportunities like this are rare.
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