Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
2417 PARSON LN, SARASOTA, FL 34239
$395,000166 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
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,426
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
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 is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Allison Werner (941-961-3212)
5936 DRIFTWOOD AVE #16, SARASOTA, FL 34231
$239,00030 Days on yellowkey MLS ID: A4692206
4 Days Off yellowkey (back on 5/18/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1155 Built: 1973 Tax: $2,387 (2025)Community: Baywood Colony Sec 1Villa
Taxes:$2,387
Elementary School: Phillippi Shores Elementary
High School: Riverview High
Remarks: Ideally positioned just minutes from the world-renowned shores of Siesta Key, this beautifully updated, turnkey-furnished villa offers an exceptional opportunity to own a low-maintenance coastal retreat at an approachable price point. Nestled within the waterfront community of Baywood Colony, this residence combines the ease of condominium/villa living with the privacy of a single-family home, perfect for seasonal enjoyment or effortless year-round escapes. Inside, the thoughtfully upgraded interior features luxury vinyl flooring, updated impact windows, updated kitchen with Quartz counter-tops, and a newer HVAC system (2023), creating a comfortable and move-in-ready environment. The spacious layout extends to an air-conditioned lanai and a private courtyard, ideal for relaxing after a day at the beach or entertaining guests in your own secluded outdoor space. Residents enjoy access to a serene waterfront park along Sarasota Bay, where sunset views, fishing, and coastal breezes become part of your daily routine, along with a community pool, clubhouse, and fitness amenities. With HOA coverage that includes flood and hurricane insurance, lawn maintenance, and your cable and water bills, ownership is truly carefree. Located approximately 2 miles from Siesta Key Beach and close to dining, shopping, and cultural attractions, this property presents a rare chance to secure an affordable slice of the Sarasota lifestyle, whether as a personal getaway, seasonal residence, or income-producing investment.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-966-8000)
Listing Agent: Adrian Mociran (941-302-8603)
1473 LANDINGS CIR #44, SARASOTA, FL 34231
$448,888287 Days on yellowkey MLS ID: A4662144
REDUCED by $20,000 (4.3%) on 05/13/2026
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2040 Built: 1981 Tax: $6,233 (2024)Community: Landings TreehouseCondo
Taxes:$6,233
Tax Year: 2024
Remarks: Welcome to The Landings Treehouse, one of Sarasota’s most sought-after gated communities. This spacious 3-bedroom, 2.5-bath residence offers over 2,000 sq. ft. of living space with a thoughtfully designed open floor plan that balances comfort and style. The main level features a bright living and dining area with soaring ceilings, skylights, a cozy fireplace, and access to a private lanai surrounded by lush tropical landscaping. The updated kitchen boasts granite counters, a center island, breakfast bar, solid wood cabinetry, and stainless-steel appliances—perfect for both everyday living and entertaining. Upstairs, the primary suite offers a walk-in closet, high ceilings, and a spa-inspired bathroom with skylights that fill the space with natural light. Two additional bedrooms provide plenty of room for guests, one with its own en suite bath. Throughout the home, you’ll find luxury vinyl and tile flooring, designer finishes, and built-in features that enhance functionality. Set among mature trees and serene nature, The Landings Treehouse community is known for its exclusive amenities, including a heated community pool, tennis courts, walking trails, and private access to the Intracoastal Waterway through the Landings Racquet Club (membership optional). This desirable location places you just minutes from Siesta Key Beach, Downtown Sarasota, St. Armands Circle, and a variety of shopping, dining, and cultural attractions. With its generous floor plan, resort-style amenities, and unbeatable location, this home is the perfect opportunity to enjoy the relaxed yet vibrant Sarasota lifestyle. The quarterly fee includes flood insurance, roof, outdoor maintenance and landscaping, gutter cleaning, pest control, Treehouse community pool, kayak launch, cable, internet. No additional assessments.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Lisa Michel (941-702-3889)
2037 and 2039 JO AN DR, SARASOTA, FL 34231
$629,00032 Days on yellowkey MLS ID: A4692288
REDUCED by $20,000 (3.1%) on 05/17/2026
Bed: 4 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 1988 Built: 1955 Tax: $5,534 (2024)Community: High AcresSpa: YesHalf Duplex
Taxes:$5,534
Remarks: Live the Florida Dream for Free – Premier Sarasota Duplex with Income Potential Why choose between a luxury home and a smart investment? At 2037 & 2039 Jo An Drive, you can have both. This meticulously maintained side-by-side duplex offers a rare opportunity to occupy a beautiful 2BR/2BA residence while the identical neighboring unit generates significant rental income to offset your costs. The Lifestyle: Enjoy your own private oasis featuring a luxurious swim spa and a massive, deep-bay garage perfect for boat storage—all just 3 miles from the world-famous Siesta Key Public Beach. The Income: With RMF-1 zoning, this property is a turnkey powerhouse. Whether you prefer stable long-term tenants or want to capitalize on the high-demand short-term rental market, the numbers work in your favor. The Location: Tucked away on a quiet street but only minutes from Southside Village, premier dining, and top-rated schools. Ideal for: The "House Hacker": Live in one side and let the other pay your mortgage. The Seasonal Resident: Live here in the winter and rent both units during the peak vacation season. The Savvy Investor: Maximize your ROI with two updated units in a prime coastal location. Don’t just buy a home—buy an asset. Contact us today for a private tour and a full rental income projection.
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Marcus Mumm (920-960-0413)
225 HOURGLASS WAY #202, SARASOTA, FL 34242
$510,00055 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 is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Harriet Stopher (404-316-8944)
4034 ROBERTS POINT RD, SARASOTA, FL 34242
$8,500,00022 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)
5649 WESTWIND LN, SARASOTA, FL 34231
$299,00022 Days on yellowkey MLS ID: A4693241
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1169 Built: 1980Monthly Fee: $560 Tax: $2,641 (2025)Community: Villa GardensVilla
Taxes:$2,641
Elementary School: Gulf Gate Elementary
Remarks: Welcome to your hidden gem in the heart of Sarasota ? This charming Westwind Lane home invites you in with a bright, open layout and tasteful updates that make it feel warm and move-in ready from day one. Step outside to your own private space—perfect for unwinding after a long day or hosting friends and family while enjoying the Florida lifestyle. Just minutes from Siesta Key and close to great shopping, dining, and daily conveniences, the location truly speaks for itself. It’s the kind of place you dream about when you think of living in Sarasota. Come see it for yourself—schedule your private showing today before it’s gone!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Marina Paige (941-263-9545)
1885 CLEMATIS ST, SARASOTA, FL 34239
$2,599,99034 Days on yellowkey MLS ID: A4691671
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 3215 Built: 2011 Tax: $18,357 (2025)Community: Desota ParkSpa: YesSingle Family
Taxes:$18,357
Remarks: Perfectly positioned on one of Sarasota's most coveted West of Trail locations - the "Flower" streets - this custom built residence delivers a lifestyle that's walkable, central and effortlessly connected to everything Sarasota. Just three blocks to Hillview's shopping, dining and Sarasota Memorial Hospital, a short stroll to top-rated Southside Elementary and only minutes to downtown Sarasota and world-renowned Siesta Key Beach - this is the epitome of "Location. Location. Location." Built in 2011 by Paradise Homes, the home offers over 3,200 square feet of thoughtfully designed one-story living with 4 bedrooms and 3 baths. A bright, open-concept layout creates a natural flow for entertaining, while the split floor plan provides ideal privacy for guests or family. High-end finishes and custom details are found throughout—from tray ceilings and built-ins to designer closets and a warm gas fireplace anchoring the main living space. The chef’s kitchen is both functional and refined, featuring stainless Viking appliances, granite countertops, custom cabinetry with glass accents, a walk-in pantry, and a reverse osmosis system with instant hot water—perfect for everyday living and hosting alike. Step outside to your pocketing sliding doors to a shaded, private Florida retreat - where a saltwater PebbleTec pool and spa, pavered pool deck, and fire pit set the tone for relaxed coastal living. The fully equipped outdoor kitchen—complete with grill, sink, and refrigerator—makes entertaining a breeze, all complemented by a charming side garden for added privacy and ambiance. Constructed with concrete block and outfitted with all impact-rated windows and doors plus electronic shutters - the home offers exceptional peace of mind. Modern conveniences include a Control4 smart home system and a new (2025) tankless water heater. An oversized three-car garage with epoxy flooring, irrigation well, and meticulous attention to detail complete the offering.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Monica Verinder (941-704-4040)
1884 SOUTHPOINTE DR, SARASOTA, FL 34231
$999,90041 Days on yellowkey MLS ID: A4690446
Bed: 6 Bath: 0.0 Liv Area Sq Ft: 2808 Built: 1972 Tax: $9,540 (2025)Community: Southpointe ShoresSpa: NoApartment
Taxes:$9,540
Remarks: A rare West of the Trail gem in Southpointe Shores, this beautifully updated 2,808 sq. ft. duplex captures the very best of Sarasota living, sun-soaked, private, and filled with opportunity. Whether you’re an investor seeking strong income potential, a homeowner looking to live in one side while the other helps offset the mortgage, or someone envisioning a future single-family coastal retreat, this exceptional property offers endless flexibility and long-term value. Each residence has been thoughtfully designed for comfort, privacy, and effortless modern living. With two private entrances, separate fenced backyards, and charming brick-paver patios, the layout creates the perfect blend of independence and connection, ideal for enjoying morning coffee beneath the palms or hosting intimate evenings under the stars. The left side, unit 1886, spans 1,639 sq. ft. and features 4 bedrooms, 3 bathrooms, a screened lanai, gas range, stainless steel appliances, luxury quartz countertops, elegant tray ceilings, and a versatile floor plan perfectly suited for families, guests, or long-term rental income. The right side, unit 1884, offers 1,087 sq. ft. with 2 bedrooms, 2 bathrooms, a light-filled sunroom, stainless steel appliances, quartz countertops, tray ceilings, and its own private fenced backyard, delivering warm coastal charm and easy everyday living. Both units include private indoor laundry rooms, backyards, and hurricane-impact windows, making this property truly move-in or rent-ready from day one. Beyond the home, Southpointe Shores welcomes you with quiet, tree-lined streets and optional HOA access to a private boat ramp and kayak launch perfect for sunset cruises, paddleboarding, or spontaneous days exploring Sarasota Bay. Just minutes away, enjoy the world-renowned shores of Siesta Key, the vibrant arts, dining, and culture of Downtown Sarasota, plus the boutique shopping and neighborhood charm of The Landings and Gulf Gate Village. More than a duplex, this is a lifestyle investment where location, versatility, and coastal elegance come together. Live beautifully. Earn effortlessly. Expand when the time is right. Own your piece of Sarasota magic in Southpointe Shores.
Listing Agent: Mark Klecka (941-348-9400)
2303 LOMA LINDA ST, SARASOTA, FL 34239
$1,899,000156 Days on yellowkey MLS ID: A4676235
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2708 Built: 2025 Tax: $4,955 (2025)Community: Loma Linda ParkSpa: NoSingle Family
Taxes:$4,955
Elementary School: Alta Vista Elementary
Remarks: Fantastic $100,000 price reduction!!! In the well-established Loma Linda Park neighborhood in Sarasota, this new construction, Divald Homes custom-built two-story home offers a blend of modern design and traditional elements. The home is ideally near downtown Sarasota, Siesta Key and Sarasota Memorial Hospital, with no deed restrictions or HOA fees. The home features four bedrooms and three baths, including a spacious primary suite on the main floor. The open-concept floor plan featuring a 24-by-48-inch modern floor tile throughout, hurricane impact sliding doors and windows offers a light-filled welcoming space ideal for entertaining. The main floor includes a gourmet kitchen, dining area, living room, private den/bedroom 4, primary suite with an ensuite bath and a dedicated laundry room. The chef’s kitchen is a centerpiece, showcasing Bosch appliances, an oversized island with waterfall quartz countertop, and custom floor-to-ceiling full-overlay cabinetry in a beautiful honey-stained wood tone. The living room is highlighted by a striking tile accent wall with custom wood shelving and modern designed 42-inch linear electric fireplace. The living room opens seamlessly to the lanai, complete with an outdoor kitchen, including a gas grill, refrigerator and sink. You will also enjoy the pool with sundeck, oversized outdoor patio and a beautiful backyard with lush native plantings. A convenient pool bath offers direct access from the lanai and the private den. The dining area is elegant and inviting, featuring a statement iron chandelier and a wall of windows overlooking the backyard. Just off the kitchen, the main-floor primary suite serves as a private retreat with a luxurious en-suite bath featuring a marble stone accent wall, a large walk-in shower with seamless glass enclosure, a sculptural slipper tub, double vanity with quartz countertops, natural wood cabinetry, LED mirrors and a spacious walk-in closet with custom built-ins. The laundry room is conveniently near the oversized two-car garage with 12-foot ceilings, large windows for natural light and direct access to the side yard. Upstairs, an ornate wrought-iron and hardwood staircase leads to two additional bedrooms, a beautifully finished guest bath and a versatile flex room ideal for a game room, study or guest accommodations. This thoughtfully designed home offers refined finishes, flexible living spaces and an exceptional location, ideal for enjoying the Sarasota lifestyle.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Robert Sherman (941-313-1301)
8101 GABANNA DR, SARASOTA, FL 34231
$849,000182 Days on yellowkey MLS ID: A4673093
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2106 Built: 2016Monthly Fee: $570 Tax: $6,729 (2025)Community: Esplanade By Siesta KeySingle Family
Taxes:$6,729
Remarks: One or more photo(s) has been virtually staged. Welcome to the ideally located and coveted Esplanade by Siesta Key—where convenience meets luxury living. Located just minutes from the crystal-sand beaches of Siesta Key, this comfortable, maintenance-free home sits on a large lot at the end of a quiet cul-de-sac. The Taylor Morrison–built Farnese model offers a practical and inviting layout, featuring two en-suite bedrooms, and a den that can easily serve as a third bedroom. The gourmet kitchen is a highlight, boasting a large granite island, solid wood cabinetry, a gas cooktop, and a bright breakfast nook. The spacious primary suite has bay windows overlooking the serene pond, while the primary bathroom includes neutral countertops, double sinks, and a generous walk-in shower. The den provides an ideal office, reading room, or guest retreat. From the great room, sliding glass doors lead to the expansive lanai, where you can enjoy peaceful mornings taking in pond views and local wildlife. Additional features include an outdoor kitchen, tray ceilings, a large laundry room with cabinetry, a half bath, and a two-car garage. Notable upgrades—impact windows and sliders plus a whole-house Generac generator—provide peace of mind during hurricane season. The community’s exceptional amenity center offers a state-of-the-art fitness facility, on site manager, social spaces, a resort-style pool and spa, tennis court, pickleball courts, bocce ball, and a Paw Park. Whether you prefer an active lifestyle or relaxing with friends and neighbors, Esplanade has something for everyone. Centrally located, the community offers convenient access to downtown Sarasota, shopping, dining, and the world-famous Siesta Key. This home delivers the perfect blend of comfort, convenience, and luxury—enhanced by tranquil pond views, abundant recreation, and effortless access to everything the area provides.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Tina Von Kessel (941-266-2848)
1347 LANDINGS DR #6, SARASOTA, FL 34231
$685,000351 Days on yellowkey MLS ID: A4656077
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 2564 Built: 1981Monthly Fee: $167 Tax: $8,028 (2024)Community: Landings TreehouseSpa: NoCondo
Taxes:$8,028
Remarks: Nestled among lush tropical foliage in the highly sought-after Landings community, this one-of-a-kind treehouse retreat offers the perfect blend of nature, light, and waterfront living. Ideally positioned along the scenic boardwalk near Sarasota Bay, this spacious residence is filled with sunshine and tranquil views from nearly every room. The first floor is wrapped in walls of glass, creating an airy indoor-outdoor feel and showcasing peaceful water and garden vistas. A versatile flex space offers endless possibilities as a large home office, family room, fitness studio, or creative retreat. The open kitchen features a generous dining area surrounded by windows, making every meal feel connected to the beauty of nature. Generously sized rooms throughout the home, including all bedrooms, provide comfort and flexibility for everyday living and entertaining. Just steps away, enjoy the community pool or stroll along the winding nature path through mature tropical landscaping to the bayfront gazebo — the perfect setting for spectacular sunsets and watching dolphins play in the water. Residents enjoy easy access to downtown Sarasota, world-famous beaches, exceptional dining, and shopping. Optional membership to the Landings Racquet Club offers resort-style amenities including a super sized pool, tennis and pickleball courts, fitness center, library, and welcoming social spaces to connect with neighbors and friends.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Kristina Rain (941-320-2639)
3524 S SCHOOL AVE, SARASOTA, FL 34239
$925,00019 Days on yellowkey MLS ID: A4693494
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 3037 Built: 1957 Tax: $9,338 (2025)Community: South GateSingle Family
Taxes:$9,338
Remarks: From the moment you arrive, you’ll fall in love with the charm, warmth, and unbeatable location of this tropical Mediterranean retreat in Sarasota’s highly desirable South Gate neighborhood, located within the coveted Southside School District. Perfectly situated in the heart of it all, this home places you just minutes from the world-renowned Siesta Key Beach while also being steps away from your favorite restaurants, boutique shopping, grocery stores, gyms, movie theater, and everyday conveniences. This is the rare opportunity to enjoy a true walkable lifestyle while still having the privacy and comfort of a spacious family home. Light-filled and inviting, this beautifully maintained single-story residence offers an open and airy floor plan designed for both relaxing and entertaining. With four spacious bedrooms, two remodeled bathrooms, multiple living and dining areas, a breakfast nook, sunroom, and dedicated home theater room, there is space for everyone to gather while still enjoying privacy and comfort. Large sliding glass doors, solar tubes, and gorgeous porcelain marble-look flooring fill the home with natural light and create a bright, welcoming atmosphere throughout. Step outside and discover your own private backyard paradise. The newly added heated pool with paver deck, lush tropical landscaping, fenced yard, and multiple entertaining spaces create the perfect setting for enjoying Florida living year-round. Whether you’re unwinding by the electric fireplace, soaking in the jetted tub, hosting friends and family, or biking to Siesta Key for sunset, this home offers the lifestyle buyers dream about. Thoughtful updates include a 2022 roof, newer flooring throughout, updated bathrooms, and a new water heater. The oversized two-car garage with space for a workshop, spacious laundry room, circular paver driveway, and sprinkler system on well water add both convenience and value. Currently operating as a successful vacation rental with weekly rentals allowed within city limits, the property also presents exceptional income-producing potential or flexibility for a future in-law suite. Offering one of the lowest costs per square foot in South Gate, this exceptional property combines location, lifestyle, and versatility in one unforgettable home buyers will instantly fall in love with.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Seth Westerberg (941-342-7653)
7464 CASS CIR, SARASOTA, FL 34231
$480,00033 Days on yellowkey MLS ID: A4692133
REDUCED by $29,000 (5.7%) on 05/09/2026
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1608 Built: 1969 Tax: $4,220 (2025)Community: Siesta Heights ManorSpa: NoSingle Family
Taxes:$4,220
Remarks: Welcome to this beautifully renovated 3 bedroom, 2 bath pool home with a one car garage, perfectly located just about 10 minute drive to Siesta Key, world renowned for its powdery white quartz sand, turquoise waters, and vibrant beach lifestyle. This move in ready home showcases extensive upgrades throughout, including new luxury porcelain tile flooring and baseboards, fresh interior paint, and updated lighting and ceiling fans. The kitchen offers a clean feel with new ceiling lights, a stylish subway tile backsplash, and improved plumbing, while both bathrooms have been fully remodeled with new tile, fixtures, shower systems, glass doors, vanities, mirrors, and lighting for a spa like experience. Major system improvements include full repiping of hot and cold water lines, updated electrical, and a newer hot water heater for peace of mind. Step outside to your private backyard retreat featuring a resurfaced pool with new tile, updated pump and filter, a refreshed and painted pool deck, and a rescreened enclosure, perfect for entertaining or relaxing after a day at the beach. Additional upgrades include a newer roof, enhanced attic insulation, a solar attic fan, and reflective roof coating to improve energy efficiency and keep the home cool year round. This property offers the ideal blend of location, lifestyle, and major upgrades, making it a standout opportunity near one of Florida’s most sought after coastal destinations.
Listing is courtesy of: MACHADO PROPERTY PROS (941-587-7488)
Listing Agent: Ana Machado (941-587-7488)
1332 SIESTA BAYSIDE DR #1332C, SARASOTA, FL 34242
$699,90054 Days on yellowkey MLS ID: A4689488
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1280 Built: 1988 Tax: $7,606 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$7,606
Remarks: Turnkey furnished and beautifully updated, this ground-level 2-bedroom, 2-bath residence in Gulf & Bay Club Bayside offers an exceptional blend of comfort, convenience, and Siesta Key lifestyle. Lightly lived in and meticulously maintained, the interior features a renovated kitchen with stainless steel appliances, solid stone countertops, breakfast bar seating, recessed lighting, custom tray ceiling detail, and an open connection to the main living area that enhances both everyday living and entertaining. Large-format tile flooring runs throughout the main living spaces, while both bathrooms have been tastefully updated with stone counters and tiled shower surrounds. The spacious primary suite offers a relaxing retreat with direct access to the screened lanai, and the guest bedroom is well appointed for family and visitors. Coastal furnishings and decor create a true move-in-ready presentation. The oversized screened lanai expands the living space and provides a peaceful setting surrounded by tropical landscaping, with the community walking path just outside leading to the Intracoastal fishing area, tennis and pickleball courts, and the second pool. Ideally positioned within the community, this residence is also just a short distance to the clubhouse, fitness center, BBQ area, and main pool. Owners and guests enjoy deeded beach access through Gulf & Bay Club across the street, placing world-famous Siesta Beach just a short stroll away. Siesta Beach is currently the No. 1 beach in the U.S. in TripAdvisor's 2025 Travelers' Choice Awards, and Sarasota County provides free trolley service connecting Siesta Key Village, Siesta Beach, South Village, and Turtle Beach. The location also offers convenient access on and off the island, with nearby Siesta Key Village offering shopping, dining, and the relaxed island atmosphere that makes this area so desirable. A private garage completes the package. Whether sought as a personal retreat, seasonal escape, or investment opportunity, this updated Gulf & Bay Club Bayside residence is an outstanding opportunity on Siesta Key.
Listing Agent: Shane Lewis (941-685-3252)
2135 DATURA ST, SARASOTA, FL 34239
$1,725,00081 Days on yellowkey MLS ID: A4685791
REDUCED by $75,000 (4.2%) on 05/08/2026
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2539 Built: 2021 Tax: $7,357 (2025)Community: Grove Lawn RepSingle Family
Taxes:$7,357
Remarks: This beautifully crafted custom home combines modern farmhouse style with exceptional craftsmanship and designer finishes throughout. Featuring 3 bedrooms, 2.5 baths, and an open-concept floor plan, the residence offers a perfect balance of comfort, style, and functionality. Eye-catching curb appeal begins with a cypress wood garage door, cypress porch accents, and a dramatic glass entryway that sets the tone for the thoughtfully designed interior. Filled with natural light, the two-story home showcases European oak flooring, recessed lighting, and a warm, inviting atmosphere throughout. The spacious great room features soaring 12-foot vaulted ceilings accented by a decorative cypress beam and a sleek electric fireplace, creating a stunning focal point ideal for everyday living and entertaining. The chef’s kitchen is both stylish and functional, featuring a Fulgor Milano dual-fuel range, Silestone quartz countertops, custom soft-close wood cabinetry, a large waterfall-edge island, floating cypress shelves, brass fixtures, and a generous walk-in pantry. The primary suite offers a peaceful retreat with a spacious bedroom, custom walk-in closet, and a spa-inspired bath complete with dual showers, double vanities, and custom cypress shelving. Additional highlights include beautiful wood staircases with wrought iron railings leading to a second-story bonus room, along with a spacious laundry and mudroom combination offering extensive storage and workspace. Step outside to a large private backyard with plenty of room for a future pool, surrounded by a six-foot cypress shadowbox fence ideal for pets, entertaining, and outdoor living. Ideally located east of the Trail in Sarasota, this exceptional home is just moments from Sarasota Memorial Hospital, Southside Village, and Southside Elementary School, while downtown Sarasota’s dining, arts, culture, and world-famous Gulf beaches are only a short drive away.
Listing is courtesy of: WILLIAM RAVEIS REAL ESTATE (941-867-3901)
Listing Agent: Jennifer Thompson, Pa (941-928-0790)
6215 RODGERS AVE, SARASOTA, FL 34231
$449,999154 Days on yellowkey MLS ID: A4676446
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1548 Built: 1958 Tax: $3,656 (2025)Community: Denham AcresSpa: NoSingle Family
Taxes:$3,656
Remarks: Hard to find combination: no HOA, no deed restrictions, and just minutes to Siesta Key's world-famous beaches. This 3BR/2BA home is a proven Airbnb performer, turnkey furnished and ready for continued STR income or owner occupancy. Walk to Gulf Gate's popular dining and coffee spots, including Tralia and Clever Cup. Major updates include hurricane impact windows (2020), roof (2017), and whole-home water filtration system (2024). Oversized 25x20 screened lanai features an insulated roof for year-round comfort. Fully fenced backyard with complete privacy, 20x10 storage building, and space for boat or RV parking. Updated kitchen offers granite countertops, wood cabinetry, Whirlpool appliances, and large breakfast bar. Spacious bonus room ideal for dining or entertaining. Third bedroom features two large closets. Inside laundry. Whether you're looking for a cash-flowing investment or a well-maintained home in a walkable neighborhood this close to the beach, this property delivers on both.
Listing is courtesy of: REAL BROKER, LLC (855-450-0442)
Listing Agent: Dan Mackinnon (941-323-9800)
5400 OCEAN BLVD #8-05, SARASOTA, FL 34242
$690,000210 Days on yellowkey MLS ID: A4670371
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 522 Built: 1970 Tax: $6,969 (2025)Community: Beach TerraceCondo
Taxes:$6,969
Remarks: BEACH TERRACE - STUDIO GULF-FRONT RESIDENCE: YOUR PERFECT SIESTA KEY PIED-À-TERRE Discover your ideal coastal escape at Beach Terrace, perfectly positioned at the end of Siesta Key Village with direct Gulf of Mexico frontage. This charming studio residence offers the perfect pied-à-terre for those seeking an effortless weekend getaway to paradise. Whether you call Sarasota or Lakewood Ranch home, imagine having your own Siesta Key retreat just moments away, a place to unwind, recharge, and embrace the coastal lifestyle whenever you need it. The private balcony frames stunning Gulf views, while the thoughtfully designed interior maximizes space and comfort. Covered parking provides convenient, weather-protected access to your beach escape, while the residence's prime location puts you steps from all the dining, shopping, and entertainment that Siesta Key Village has to offer. No need to drive once you arrive, everything is at your fingertips. Resort-style amenities elevate the experience: enjoy the elevated heated saltwater pool with its spectacular sunset views (truly the best amenity besides the unbeatable location), stay active in the fitness center, gather in the community room, and access the world-renowned Siesta Key Beach directly from the property. The powdery white sand and crystal-clear waters are quite literally your backyard. More than a weekend residence, this is your personal gateway to the Gulf-front lifestyle. Whether it's a spontaneous Friday escape or a planned coastal retreat, your Siesta Key sanctuary awaits. This is the effortless beach lifestyle you've been dreaming of, close to home, yet worlds away.
Listing Agent: Mickey Kiernan (941-402-9115)
625 BEACH RD #602, SARASOTA, FL 34242
$999,000225 Days on yellowkey MLS ID: A4669231
1 Days Off yellowkey (back on 5/17/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1144 Built: 1975 Tax: $8,966 (2024)Community: Tivoli By The SeaCondo
Taxes:$8,966
Remarks: Under contract-accepting backup offers. PRICE REDUCTION OF NEARLY $300,000!!! MOTIVATED SELLERS! DIRECT GULF VIEWS accompany this FULLY REMODELED two-bedroom, two-bath PENTHOUSE offering WEEKLY RENTALS AT TIVOLI BY THE SEA on SIESTA KEY. The residence is presented TURNKEY FURNISHED and ready for immediate occupancy or rental. Comparable units in Tivoli generate APPROXIMATELY $100,000 IN ANNUAL BOOKINGS providing an excellent opportunity to own a piece of Siesta Key while enjoying personal use and potential income. This BEACHFRONT CONDO boasts sophisticated modern design and a tranquil beachside ambiance in a prime, secluded yet connected location. A SPACIOUS 26' X 6' BALCONY OFFERS PANORAMIC GULF VIEWS ideal for enjoying sunrise coffee or sunset cocktails. The living areas feature sleek lines, a neutral palette, and abundant natural light to create an airy atmosphere. The STATE-OF-THE ART KITCHEN is equipped with PREMIUM FIXTURES, TOP-TIER STAINLESS STEEL APPLIANCES including a SUBZERO REFRIGERATOR, STONE COUNTERTOPS, and CUSTOM WOOD CABINETRY. Plush bedrooms provide comfort and serene views, with the master suite featuring direct Gulf views via sliding glass doors, a SPA -INSPIRED ENSUITE BATHROOM WITH HIGH-END FINISHES, and a large walk-in closet. For added assurance, this sixth-floor unit includes MAXIMUM HURRCANE PROTECTION WITH FULL ELECTRIC METAL ROLL-DOWN SHUTTERS. Residents enjoy access to a SWIMMING POOL, poolside cabana with billiard and ping pong tables, ROOFTOP CLUB ROOM WITH EXPANSIVE GULF VIEWS, private tennis and basketball courts, putting green, FITNESS CENTER, and PRIVATE GATED ACCESS to Siesta Key Beach. The community is within walking distance to Siesta Key Village’s restaurants, boutiques, bike rentals, and vibrant nightlife. This property exemplifies elegance, comfort, and the beauty of oceanfront living. It presents a unique lifestyle opportunity for discerning buyers seeking both luxury and investment potential. CALL FOR YOUR SHOWING TODAY!
Listing Agent: Susanne Losso (941-928-0023)
3167 IRVING ST, SARASOTA, FL 34237
$475,00018 Days on yellowkey MLS ID: A4693818
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 2006 Built: 1956 Tax: $3,940 (2025)Community: Bellevue Terrace Rev Blk BSingle Family
Taxes:$3,940
Remarks: Stop searching, this is the one. Welcome to this renovated charming 2000 sf, 3 bedroom, 2 bath home designed for comfort and flexibility. The bright, open floor plan feathers a dedicated den/office perfect for a home office, playroom or quiet hobby space. The kitchen flows seamlessly into the living area and large family room with built-in fireplace and pizza over making it ideal for entertaining. Step outside to your private backyard oasis, complete with sturdy, spacious shed (Perfect for a workshop, extra storage or garden tools!). Don't miss this chance to own this versatile gem in a highly desired neighborhood with easy access to the legacy trail an all of Sarasota's beaches, shopping and dining.
Listing is courtesy of: GULFSIDE REALTY OF SARASOTA, INC (941-309-5169)
Listing Agent: Brent Karweck (941-757-9600)
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