Location: Sarasota
Keyword(s): Brookside Middle
Keyword(s) Middle School: Brookside Middle
Do Not Show Listings
1958 MORRIS ST, SARASOTA, FL 34239
$1,099,900161 Days on yellowkey MLS ID: A4677121
REDUCED by $95,100 (8.0%) on 05/29/2026
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2362 Built: 1957 Tax: $7,088 (2025)Community: HartsdaleSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$7,088
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Virtually Staged. Now offering buyer incentives and priced below appraised value! This exceptional single-family pool home offers the perfect blend of space, flexibility, and prime Sarasota location. Featuring 4 bedrooms and 3 full bathrooms, this residence is thoughtfully designed to accommodate a variety of living arrangements, including two primary suites, each with its own en suite bathroom—ideal for multigenerational living, extended guests, or a private home office retreat. Light-filled living spaces flow effortlessly, creating an inviting atmosphere for both everyday living and entertaining. The functional layout offers privacy where you want it and openness where it matters most, making the home equally suited for relaxed coastal living or hosting family and friends. NEW ROOF 2025. NO STORM DAMAGE. Step outside to your private fenced backyard oasis, where an oversized sparkling swimming pool takes center stage—perfect for year-round enjoyment in Florida’s sunshine. Located West of the Trail, this home places you in one of Sarasota’s most desirable areas. Enjoy the convenience of being just minutes from Downtown Sarasota, with its vibrant arts scene, dining, and waterfront attractions. The popular Morton's Market and Hillview shops and restaurants are close by for everyday errands and casual nights out, "A" rated Southside Elementary School just around the corner, Siesta Key Beach and Sarasota Memorial Hospital are only moments away, adding peace of mind and unmatched accessibility. Whether you’re searching for a full-time residence, seasonal getaway, or smart investment, this home stands out with its versatile floor plan, unbeatable location, and outstanding value. Opportunities like this in such a sought-after Sarasota setting—are rare. Schedule your private showing today and experience the lifestyle this property has to offer.
Listing is courtesy of: WAGNER REALTY (941-955-1500)
Listing Agent: Jon Patella (941-228-1613)
527 VENICE LN, SARASOTA, FL 34242
$4,950,000166 Days on yellowkey MLS ID: A4676628
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 4158 Built: 2026 Tax: $11,622 (2025)Community: Siesta BeachSpa: YesSingle Family
Taxes:$11,622
Elementary School: Phillippi Shores Elementary
Remarks: Virtually Staged. Under Construction. Be the first owner of this exceptional new construction home. Enjoy gorgeous, wide Grand Canal views with quick access to Sarasota Bay—a true boater’s dream. This home showcases high-end construction at its core, featuring a standing seam metal roof, hurricane-impact windows and sliders, elegant stone detailing, and meticulous craftsmanship throughout—no detail has been overlooked. Offering 4 bedrooms and 5 bathrooms, including a pool bath and an additional half bath, the layout is both luxurious and functional. Enter through the grand foyer with soaring ceilings, custom trim work, and striking shiplap accents. The open floor plan seamlessly connects the grand room, dining area, and bonus space, all leading to a stunning pool and patio with outdoor kitchen, perfect for entertaining. The chef’s kitchen is beautifully appointed with stone countertops, custom cabinetry, and premium finishes, complemented by matching stone counters and custom cabinetry in all bathrooms, creating a cohesive and elevated design throughout the home. Custom wood decking winds its way to the dock, enhancing the waterfront lifestyle. The home also features laundry rooms on all three floors, a spacious loft, and thoughtfully designed primary and guest bedroom suites. This is a rare opportunity to own a meticulously crafted waterfront residence designed for luxury living and boating enthusiasts alike.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Cassie Meyer (941-650-4935)
533 VENICE LN, SARASOTA, FL 34242
$4,800,000166 Days on yellowkey MLS ID: A4676632
Bed: 4 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3765 Built: 2026 Tax: $11,368 (2025)Community: Siesta BeachSpa: NoSingle Family
Taxes:$11,368
Remarks: Virtually Staged. Under Construction. New Construction. This stunning new waterfront home is perfectly positioned on Siesta Key’s Grand Canal, offering excellent boating water with quick access to Sarasota Bay. The residence features 4 bedrooms, 5 full baths (including a pool bath), and 1 half bath, along with two laundry rooms conveniently located on the first and third floors. A spacious third-floor loft provides a versatile living area just before entering the primary suite, ideal for a lounge, office, or private retreat. The open-concept family room and dining area showcase a Thermador-equipped kitchen and overlook a spectacular outdoor living space with an outdoor kitchen, pool with sun shelf, and custom deck leading directly to your private dock. Two balconies—one at the front of the home and one with sweeping waterfront views—enhance the indoor-outdoor lifestyle. Custom cabinetry throughout, quartzite countertops, and high-quality construction reflect attention to detail at every turn. Located just minutes from Siesta Key Beach, Siesta Village, and all of Sarasota’s amenities, this exceptional waterfront home is a rare opportunity—come see it for yourself.
1260 DOLPHIN BAY WAY #404, SARASOTA, FL 34242
$1,395,000197 Days on yellowkey MLS ID: A4673762
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1997 Tax: $12,793 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,793
Remarks: ENJOY SERENE INTRA-COASTAL WATER VIEWS from this this 4th floor, end unit, 3 bedroom, 3 full bath condo at Dolphin Bay. This community lives life to the fullest! Lots of social activities and friendly and caring neighborhood. Take a new look and enjoy the fresh new decor and new high impact windows and sliders, all added in 2025! Reduced condo fees. This meticulously maintained condo lives like a single family home with charm and character. The kitchen was custom built by Yoder Construction, a well-known local company, highly respected for their craftsmanship. Living room and dining area are bright and spacious. The large primary bedroom has a walk-in closet and ensuite with shower and separate soaking tub. There are two other ensuite bedrooms. All three bedrooms have California Closet systems. All windows have custom plantation shutters, adding to the charm and comfort of this amazing condo. You will want to spend your day on the light filled lanai, perfect for entertaining or simply relaxing. Dolphin Bay is a highly desirable, gated, pet friendly, 50-unit complex with a fun filled community atmosphere with three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier and kayak access. Dolphin Bay is well maintained with a freshly updated exterior and new elevators in 2024 and beautifully landscaped grounds. Just a short walk to the world famous, white crystal sands of Siesta Key beach.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Mina Johnson (941-404-9347)
5880 MIDNIGHT PASS RD #206, SARASOTA, FL 34242
$1,335,000243 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)
1240 DOLPHIN BAY WAY #401, SARASOTA, FL 34242
$1,199,000261 Days on yellowkey MLS ID: A4658380
Bed: 3 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 2200 Built: 1998 Tax: $12,546 (2025)Community: Dolphin BaySpa: YesCondo
Taxes:$12,546
Remarks: Huge Price Reduction!!! Fourth-floor end unit offering breathtaking views of the intracoastal waterway, featuring three spacious bedrooms and three full ensuite baths. Newly installed luxury vinyl plank flooring graces the entire unit. The expansive glassed lanai boasts recently replaced sliding doors, complete with accordion shutters on the inner doors and impact-resistant glass on the outer ones. The kitchen has been thoughtfully opened up and reconfigured for optimal enjoyment. The living and dining areas are bright and roomy. Dolphin Bay is a sought-after, gated, pet-friendly community with only 50 units, each having its own private underbuilding garage, and well-known for its vibrant atmosphere. Amenities include three Har-Tru tennis courts, an active clubhouse, fitness center, pool and spa, day dock, fishing pier, and kayak access. The complex is well-maintained, with a freshly updated exterior and new elevators in 2024, set amidst beautifully landscaped grounds. Just a short stroll to the world-renowned, white crystal sands of Siesta Key beach. Condo fees at Dolphin Bay are being lowered in 2026.
Listing Agent: Ethel Lovelace (941-586-7390)
1789 LOMA LINDA ST, SARASOTA, FL 34239
$1,395,000593 Days on yellowkey MLS ID: A4627340
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2560 Built: 1950 Tax: $14,382 (2023)Community: Pomelo Place ResubSpa: NoSingle Family
Taxes:$14,382
Tax Year: 2023
Remarks: The West of Trail BEST BUY!! Located between Osprey Avenue and Orange Ave, rarely will you find a 2500+ square foot cement block home on an oversized corner lot (100' x 142') with 3 bedrooms, 2 bathrooms, 2 car attached garage and pool for this price. Open floor plan with high ceilings in living areas, wood flooring, spacious living and dining areas, wine cellar, separate laundry room, screened in pool and large lanai. Automatic driveway gate for garage side entry on Osprey and circular drive on Loma Linda. Prime location just down the street from popular Southside Village shops and restaurants and in highly acclaimed schoold districts. Come see for yourself and have a very pleasant surprise. No interior storm damage in the home.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Barbara May (404-822-9264)
4819 HIGEL AVE, SARASOTA, FL 34242
$5,392,000669 Days on yellowkey MLS ID: A4620571
Bed: 4 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4220 Built: 2024Community: Siesta BeachSpa: YesSingle Family
Taxes:$0
Remarks: Virtually Staged. New Construction. Come see this coastal Siesta Key home located on the Grand Canal. The home is located on prime waterfront property with the best views of the Grand Canal, which provides easy access to the bay. A boater's dream! This three-level waterfront property offers the best in luxurious living, with four spacious bedrooms and four full baths and two half baths. Step inside the impressive front doors into the bright foyer which leads to the spacious great room, well-planned kitchen and bonus and/or dining room. Take in the beautiful wide views of the Grand Canal from your gorgeous pool, spa and travertine deck or while cooking from your outdoor kitchen. The first floor also features the primary bedroom, powder bath, and laundry room. The beauty of the home is the open concept living area which allows for natural light to flow from large windows and slider throughout the space. Located on the second floor are the second and third bedrooms each with their en suite bathroom. On the third floor, you will find another master suite where you can enjoy more waterfront views from its balcony. Enjoy your private den or office with walk in closet and mechanical storage closet. This home is situated in a prime location, just moments away from the world-famous Siesta Key Beach, known for its pristine beaches and clear waters. Close enough to famous Siesta Key Village but still out of the hustle and bustle. Also this home is in walking distance to The Out of Door Academy. Explore local dining and shopping or enjoy all the activities that Siesta Key living provides, fishing, boating, kayaking, walking, biking. You can even golf cart to the Siesta Key Village. Come see for yourself, this brand new residence and feel the Siesta Key life style. This is an exceptional custom home with well appointed extra features that will give you the best, easiest coastal living in Sarasota. Don't miss out on this home! Some photos virtually staged.
1921 MONTE CARLO DR #603, SARASOTA, FL 34231
$450,000175 Days on yellowkey MLS ID: A4676140
REDUCED by $20,000 (4.3%) on 06/01/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1706 Built: 2006 Tax: $6,676 (2025)Community: Phillippi Landings ACondo
Taxes:$6,676
High School: Riverview High
Remarks: Price Adjustment! An exceptional value for the view, location, and lifestyle—this sixth-floor, two-bedroom, two-bath residence is a rare opportunity that should not be overlooked. From the moment you enter, expansive water views command your attention, setting the tone for this open and inviting floor plan where water surrounds you in every direction. The spacious, light-filled kitchen offers abundant storage and serves as a natural gathering place for guests. Just beyond, you’ll find a convenient laundry closet, a full guest bath, and a generously sized second bedroom—ideal for visitors or a home office. The main living area easily accommodates both comfortable seating and a formal dining arrangement, flowing seamlessly into the great room and out to the oversized screened balcony. This elevated vantage point is perfect for relaxing, entertaining, and taking in sweeping waterfront views that are increasingly hard to find at this price point. The owner’s suite is thoughtfully positioned for privacy and features direct access to the lanai, allowing you to wake up to tranquil water views each morning. Two walk-in closets and a spacious en-suite bath with both a soaking tub and separate shower complete this retreat. This unit has a deeded parking space under cover in the garage. There is also a storage unit assigned to this unit for seasonal accents. Set within a beautifully maintained 10-acre waterfront community, residents enjoy resort-style amenities including a heated pool and spa, fitness center, clubhouse, and an expansive promenade along the water—ideal for sunset strolls. There is a Kayak launch access and private storage racks offer direct connection to Phillippi Creek for boating and nature lovers. The location further elevates the value: minutes from The Landings Shopping Center, Southside Village, downtown Sarasota, UTC Mall, and the white-sand beaches that define Florida’s Gulf Coast. When combined with the views, amenities, and low-maintenance lifestyle, this residence represents an outstanding opportunity—offering coastal living at a price that is increasingly rare for this setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Diane Fogo Harter (941-445-2431)
2532 FRUIT TREE DR, SARASOTA, FL 34239
$2,375,00045 Days on yellowkey MLS ID: A4692314
Bed: 6 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 3931 Built: 2025 Tax: $3,561 (2024)Community: South GateSpa: YesSingle Family
Taxes:$3,561
Tax Year: 2024
Remarks: MOTIVATED SELLER. NEW HOME IN SOUTHGATE. Built with the perfect blend of elegance, and comfort this home has so many beautiful features for today's lifestyle and modern living. The perfect blend of elegance & comfort exudes this beautiful residence. The thoughtfully designed floor plan features a first floor open living space with soaring ceilings, lots of hurricane windows and sliding doors gives this beautiful home effortless indoor-outdoor living enjoyment and fills the home with natural light. The open concept chef inspired kitchen has plenty of custom soft-close cabinet space and drawer space. All accented with under mount lighting. The large breakfast bar is perfect for casual living and entertaining. The dining area encircled with windows overlooks the lovely landscaped yard and pool/spa. Sliding doors wrap around the house from every room to the great outdoors. The master suite includes a spacious spa inspired bathroom with soaking tub and large closet space. The elegant open staircase leads to the second floor with a gathering area and outdoor balcony in the front of the house. four additional bedrooms with bathrooms and walk in closets including a family room with sliders to an outdoor veranda overlooking the yard and pool completes the home.. There is also a laundry area located on the second floor! Masterfully planned and designed with your comfort and easy living in mind. This home is impressive, beautiful and a relaxing place to call home. Located in one of the most sought after locations in Sarasota. Close to the Sarasota Memorial Hospital, Selby Gardens, Van Wezel, Oslo, Down town restaurants and shopping. Your dream Your home....
Listing is courtesy of: JOSEPH RUSSO, LICENSED R.E. BROKER (941-928-1613)
Listing Agent: Joseph Russo (941-928-1613)
2225 FLORINDA ST, SARASOTA, FL 34231
$1,500,00021 Days on yellowkey MLS ID: A4690756
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2607 Built: 2026 Tax: $1,570 (2025)Community: Tamiami TerraceSpa: YesSingle Family
Taxes:$1,570
Remarks: Virtually Staged. 2225 Florinda Street — arrival as destination. Pull into the driveway, pass the two car garage and follow a landscaped walkway to arrive at a gracious covered entry; decorative metal screening catches the Florida light accenting the french pattern travertine entry and frames an oversize full glass door. Step inside and the experience unfolds: Large format porcelain tile, 10' ceilings and abundant windows bathing the open plan in natural light. Gulfside Homes, a Sarasota Custom Home builder for over 25 years, crafted this over 2,600 sq ft Calista model showcase with thoughtful and custom upgrades you’ll notice throughout—builtin conveniences, premium appliances and finish selections that read like an owner’s wish list already checked. The main level is made for living and entertaining: an elegant dining area flows to a true gourmet kitchen with gas range, pot filler, LG stainless appliances, microwave drawer and an oversized quartz waterfall island. The family room sits beyond, flooded by light from large windows and glass doors that frame the ivory travertine pool deck and spa. Opposite the island and tucked under the stairs is a purposeful coffee bar and prep station with a deep sink (cuttingboard/dryingrack/colander), coordinated floating shelving, abundant storage and a twozone undercabinet beverage refrigerator—one of the many touches that make daily rituals effortless. Also on the first floor is a flexible, large en-suite guest room whose bath doubles as a powder room and provides direct access to the outdoors and access to the pool—perfect for visitors and carefree pool days. Upstairs the home is arranged for privacy and function: a split bedroom plan placing the primary suite apart from two large secondary bedrooms. The primary is a serene retreat with a spa caliber bath—soaking vessel tub, floor to ceiling Calacatta porcelain shower with double rain heads, dual vanities—and generous closet space. A dedicated laundry on the bedroom level adds convenience. A roomy office/den/media room opens to a covered deck for quiet moments or flexible workspace. Outside is your private Sarasota oasis: 12×24 pool with six person spa, travertine decking and glass waterline tile, pre-plumbed for heating and framed by an 8' fenced yard. Premium systems and Gulfside upgrades that other builders don’t automatically provide—impact windows, underground 500gal propane tank, Rinnai tankless water heater with recirculating system, large format porcelain tile on the main level, waterproof luxury vinyl plank upstairs, timber stairs with stainless cable railing, upgraded lighting and hardware, Ring cameras and low maintenance tropical landscaping—deliver comfort, security and low upkeep. Only blocks to The Landings shopping center with several restaurants, gym, and Publix. Minutes from the John and Mable Ringling Museum of Art, Sarasota Art Museum, Van Wezel Performing Arts Hall, Marina Jack, downtown dining, farmers’ markets, marinas and Siesta Key and gulf beaches, 2225 Florinda is a refined, turnkey Sarasota lifestyle crafted by an experienced custom builder. Schedule your private showing to experience the details in person.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Karen Sweat (941-323-6707)
1654 STICKNEY POINT RD #54-201, SARASOTA, FL 34231
$299,00050 Days on yellowkey MLS ID: A4691665
REDUCED by $11,000 (3.5%) on 06/01/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1016 Built: 1975 Tax: $3,415 (2025)Community: Castel Del MareSpa: NoCondo
Taxes:$3,415
Elementary School: Gulf Gate Elementary
Remarks: Bayfront community one block to the south bridge to Siesta Key • Turnkey furnished • 3D walkthrough available Second-floor 2-bedroom, 2-bath condo in Castel Del Mare, a waterfront community on Little Sarasota Bay at the gateway to Siesta Key. Just minutes to Siesta Key Beach at a fraction of island pricing. This 1,016 sq ft turnkey furnished residence features a partially updated kitchen, living/dining combo with ceiling fans, walk-in closet, and a screened lanai with west-facing exposure. Assigned parking included. Settle into the bayside heated pool and watch boats cruise the Intracoastal Waterway, or launch a kayak from the community dock. Castel Del Mare offers two heated pools, tennis and pickleball courts, shuffleboard, fitness center, clubhouse, bayside fishing gazebo, kayak storage with launch access, and a scenic boardwalk along Little Sarasota Bay. Rental minimum 30 days, 3 rentals per year. Near public transit with easy access to Siesta Key Beach, Siesta Village dining, and the Stickney Point Bridge. Nearby dining includes Merci Café and La Dolce Vita. Publix and Detwiler's Farm Market within 1 mile. Red Bug Slough Preserve and Gulf Gate Village nearby. Includes 3D tour for virtual viewing.
Listing Agent: Christine Pope (941-685-5565)
1751 HAWTHORNE ST, SARASOTA, FL 34239
$2,495,00067 Days on yellowkey MLS ID: A4689684
1 Days Off yellowkey (back on 6/14/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3875 Built: 2006 Tax: $33,343 (2025)Community: Hudson BayouSpa: YesSingle Family
Taxes:$33,343
Remarks: Under contract-accepting backup offers. Step into a home that feels more like a private gallery and retreat than a traditional residence—where modern design, light, and location come together in a way that’s nearly impossible to replicate in Sarasota. Located just one block from Southside Village and minutes to downtown, this West of Trail architectural residence is designed for the cosmopolitan buyer—someone who values design, art, walkability, and a lifestyle that blends indoor and outdoor living seamlessly. From the moment you enter, you’re greeted by a dramatic two-story great room with soaring ceilings, polished concrete floors, and a striking mid-century modern fireplace. A wall of glass draws your eye straight through to the sun-drenched, Palm Springs-inspired pool and lush tropical backdrop—creating that immediate “this is different” feeling. The scale and clean lines offer the perfect canvas for an art collector, with expansive walls that invite statement pieces. The kitchen is both functional and beautifully integrated—designed for someone who entertains without wanting to be separated from the experience. Custom cabinetry, a professional-grade 48" Jenn-Air gas range, double ovens, and a wet bar all open directly to the living and dining spaces, including a character-rich built-in banquet booth that feels both classic and intentional. On the main level, a guest suite with large sliders opens to a covered, screened lanai—ideal for outdoor dining or evening lounging without interruption. There’s also a dedicated office for the not-quite-retired, a bright and airy laundry room, and thoughtful storage throughout. Upstairs, the home continues to surprise. A lofted lounge creates separation for guests or quiet moments, while a spacious ensuite bedroom provides comfort and privacy. Then, a true conversation piece—the observatory, accessed via a winding staircase—offers a unique escape that feels both playful and sophisticated. The primary suite is expansive and light-filled, with generous closet space, dressing areas, and a bathroom that carries through the home’s mid-century modern aesthetic. Outdoors, the experience is equally refined. Low-maintenance designer rock beds are complemented by mature palms and lush landscaping, framing a private resort-style pool and spa. A detached 400 sq. ft. studio/guest house adds flexibility—perfect as an art studio, fitness space, guest suite, or private office with its own entrance. The garage is oversized with a two-car door but space for much more—cars, e-bikes, paddleboards, even a golf cart—supporting an active, coastal lifestyle. This is not a home for everyone—and that’s exactly the point. It’s for the buyer who has outgrown the ordinary, who appreciates architecture and design, who wants to be close to everything yet live in one of Sarasota’s most desirable residential neighborhoods. Because the reality is—homes like this rarely come available. And when they do, they don’t last. If you’ve been waiting for something that actually feels different… this is it.
Listing is courtesy of: EXP REALTY LLC (800-486-1794)
Listing Agent: Mark Coppens (941-444-0436)
3122 REGATTA CIR, SARASOTA, FL 34231
$685,000132 Days on yellowkey MLS ID: A4680447
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1642 Built: 1965 Tax: $5,399 (2025)Community: Gulf Gate WestSpa: NoSingle Family
Taxes:$5,399
Remarks: Gulf Gate transformation in this meticulously renovated 3-bedroom, 2-bathroom sanctuary. Situated on a quiet circle just minutes from the world-class sands of Siesta Beach, this home has been professionally redesigned from top to bottom with uncompromising attention to detail. Enjoy total peace of mind with a comprehensive list of 2022–2025 upgrades, including a new roof, HVAC and ductwork, PEX plumbing, and new sewer lines. The exterior features durable Hardie siding, fresh paint, and hurricane-impact windows and doors at the front, ensuring both efficiency and protection. Designer Interiors The heart of the home is a chef’s kitchen featuring Level 4 Cambria Quartz, solid wood shaker cabinetry, and a custom built-in banquet. Modern luxury vinyl flooring flows through the open living spaces, leading to a charming shiplap-accented living room with an electric fireplace. Both bathrooms have been fully redone with high-end vanities, fixtures, and custom tile. Private Backyard Oasis Step outside to a brand-new inground pool with a custom water feature, all framed by a new wood privacy fence. The grounds are completed by professional landscaping, new lighting, and a modern irrigation system. Fully permitted and ready for its next chapter, this "better-than-new" gem offers the luxury of a custom build in an established, sought-after Sarasota location.
Listing is courtesy of: VUE REALTY, LLC (941-269-8400)
Listing Agent: Deanna Boileau Gilman (860-884-7198)
9397 MIDNIGHT PASS RD #905, SARASOTA, FL 34242
$729,000241 Days on yellowkey MLS ID: A4669008
REDUCED by $20,000 (2.7%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1348 Built: 1975 Tax: $5,944 (2025)Community: Pointe On Midnight PassSpa: YesCondo
Taxes:$5,944
Remarks: Also available as a seasonal rental! Welcome to 9397 Midnight Pass Rd #905 Sarasota, FL 34242 at The Pointe on Siesta Key, a fully renovated 1,348 SF, 2-bedroom, 2-bathroom luxury condo offering breathtaking Little Sarasota Bay and Intracoastal waterway views from the 9th floor. This stunning residence underwent a complete custom renovation in 2023, setting it apart from every other unit in the building. The open-concept kitchen features quartz countertops, vaulted ceilings with a bold rock-and-metal aesthetic, and a one-of-a-kind handcrafted glass-art backsplash, with bar seating connecting seamlessly to the dining and living areas, a custom layout rarely found at The Pointe. Luxury vinyl plank flooring flows throughout every room including the lanai, while wood acoustical paneling enriches both the living space and primary suite. Additional upgrades include HD-mounted televisions, a 2023 AC system, and a new LG washer and dryer, making this unit nearly turnkey and move-in ready. Step onto your private lanai, protected by hurricane-grade sliders, and take in tranquil water views of Little Sarasota Bay, where dolphins, manatees, and sailboats pass through calm Intracoastal waters daily. As a resident of The Pointe's gated five-acre community, enjoy resort-style amenities including boat docks, kayak and canoe access, a heated pool and spa, sauna, tennis and pickleball courts, BBQ gazebos, a clubhouse, and a fitness center with panoramic Intracoastal views. Located just minutes from Turtle Beach, Siesta Key Village, waterfront dining, local marinas, and coastal cafés, this property is ideal whether you're seeking a luxury Siesta Key waterfront residence, a vacation condo, or a Sarasota investment property. Negotiable furnishings available. Schedule your private showing today.
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Emerson Robbins (941-404-0382)
2135 DATURA ST, SARASOTA, FL 34239
$1,725,00095 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)
4003 BOOTH PL, SARASOTA, FL 34231
$355,90062 Days on yellowkey MLS ID: A4690238
REDUCED by $19,100 (5.1%) on 05/02/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1306 Built: 1952 Tax: $2,979 (2025)Community: BrooksideSingle Family
Taxes:$2,979
Remarks: Welcome to this FRESH and Bright centrally located home in Sarasota! It offers 3 bedrooms, 2 bathrooms, and valuable updates that provide both comfort and peace of mind. A BRAND NEW ROOF is scheduled for installation in mid-June 2026, while the freshly painted interior (May 2026), finished in a soft/neutral white, creates a light-filled and inviting atmosphere throughout the home. The beautifully updated kitchen features newer appliances, cabinetry, white quartz countertops, and fixtures, blending style and functionality for everyday living and entertaining. The spacious primary suite is complemented by a stunning bathroom renovation completed in March 2026, showcasing modern finishes and thoughtful design. The water softener is also new. UPDATED PHOTOS WILL BE TAKEN after the new roof is completed. Step outside and enjoy the spacious screened lanai, an ideal setting for morning coffee, evening relaxation, or gathering with family and friends. The large private backyard is shaded by mature trees, offering both beauty and privacy. A one-car carport under the main roofline adds convenience and enhances the property's overall value. Located within the highly sought-after Riverview School District, this home is just minutes from Siesta Key's world-famous beaches, vibrant downtown Sarasota, premier shopping and dining, parks, and major medical facilities. Whether you're searching for a primary residence, seasonal retreat, or investment opportunity, this exceptional location offers enduring appeal. With many of the major improvements already completed—including the new roof, fresh interior paint, updated kitchen, renovated primary bathroom, and new water softener—this property presents an outstanding opportunity to enjoy the Sarasota lifestyle from day one. Combining desirable updates, a prime location, and room to make it your own, this home is ready to welcome its next owner.
Listing is courtesy of: BERKSHIRE HATHAWAY HOMESERVICE (941-907-2000)
Listing Agent: Julie Shaw (941-408-4760)
8635 MIDNIGHT PASS RD #201C, SARASOTA, FL 34242
$599,99977 Days on yellowkey MLS ID: A4688472
REDUCED by $25,000 (4.0%) on 04/24/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1160 Built: 1970 Tax: $5,913 (2025)Community: Bay Tree ClubCondo
Taxes:$5,913
Remarks: PRICE REDUCTION! This beautifully FULLY FURNISHED END-UNIT condo is a true gem, offering an abundance of natural light and a spacious, open layout. Featuring 2 bedrooms and 2 bathrooms, this home effortlessly blends comfort and style, making it the perfect space for both relaxation and entertaining. Step outside onto your private lanai and take in breathtaking views of serene Intracoastal waters—an ideal spot to unwind and embrace the peaceful surroundings. The primary bedroom features a walk-in closet and an en-suite bathroom for added convenience and comfort. The second bedroom is spacious, perfect for guests or family members alike. The kitchen boasts beautiful granite countertops, stainless steel appliances, and shaker cabinets with soft-close features, creating a sleek and functional cooking space. Located within a Gulf to Bay Community, this second-floor condo is just steps away from the pristine beach, which includes its own assigned storage cabana to stow your beach essentials, bikes, umbrellas, and chairs. Bay Tree community offers two heated pools, BBQ areas, kayak storage and fishing pier. For boating enthusiasts, the available boat slips provide easy access to the newly reopened Midnight Pass for all your water adventures. Fully furnished and with a STRONG rental history, this condo serves as an excellent income property—making it a fantastic choice for both vacation home seekers and investors alike. Equipped with HURRICANE IMPACT WINDOWS for added peace of mind and energy efficiency, this condo offers durability while maintaining a quiet, comfortable living environment. Additionally, the completed milestone inspection ensures transparency and confidence for the next homeowner. The monthly fees also cover a variety of essential services, including common area insurance, common area flood insurance, and an annual AC inspection and onsite Property Manager. Conveniently located near the free trolley stop, you’ll have easy access to explore Siesta Village’s restaurants, shops, and the world famous Siesta Key Beach with its white quartz sand. Don’t miss your chance to own a piece of paradise in one of Siesta Key’s most desirable locations. Whether you're seeking a vacation retreat, an investment property, or a coastal haven, this condo has it all! Schedule your showing today!
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Justin Piccillo (908-670-3209)
1200 SIESTA BAYSIDE DR #1200G, SARASOTA, FL 34242
$400,00092 Days on yellowkey MLS ID: A4685175
REDUCED by $25,000 (5.9%) on 06/13/2026
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 845 Built: 1988 Tax: $4,441 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$4,441
Remarks: Welcome to the world-famous Siesta Key! Now available a second-floor one-bedroom, one-bath condominium in the desirable Gulf and Bay Club Bayside. This particular condo had zero flood or storm damage. This home is just waiting for your personal touch! Enjoy direct deeded beach access just across the street to Siesta Key Beach and live a true resort-style life with wonderful amenities at your fingertips. An open floor plan greets you with tile on the diagonal, a spacious living/dining area, and a balcony overlooking the community pool. The unit is complete with a private one-car garage, indoor laundry with a brand-new stackable washer and dryer, and turnkey furnished and ready for you or your guests. Gulf and Bay Club Bayside features: Two resort-style pools Tennis and pickleball courts Newly renovated fishing dock Walking paths, boat loading zones, and four BBQ areas Clubhouse for private parties and events. This weekly-rental-friendly community also offers onsite management (directly below the unit), making it a great income opportunity for investors or those seeking a snowbird property. Location cannot be beat you just cross the road for beach access or take the free trolley to explore Siesta Key Village or South Siesta! Live the island lifestyle at Gulf and Bay Club Bayside. Tenant occupied best showing time Saturday but with enough notice we can manage a showing. Must be scheduled and approved by tenants.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Jessica Ross, Pa (941-321-9000)
3838 FLORES AVE, SARASOTA, FL 34239
$1,545,000304 Days on yellowkey MLS ID: A4661399
0 Days Off yellowkey (back on 6/13/2026)
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3033 Built: 1926 Tax: $16,879 (2025)Community: GranadaSingle Family
Taxes:$16,879
Remarks: A premier West of Trail address in Granada. A property rarely duplicated in Sarasota. Casa de Flores is a 1920s Spanish Revival compound designed for modern flexibility — multi-generational living, private guest quarters, and exceptional indoor-outdoor entertaining — all set within one of Sarasota’s most coveted neighborhoods of Granada. The main residence offers two bedrooms and two baths, anchored by a charming, well-appointed kitchen that blends character and functionality. Equipped with a 6-burner Dacor gas range, double ovens, a Sub-Zero refrigerator, and artisan tile accents, the space is intimate yet efficient — perfectly suited for everyday living or hosting close friends. Formal and informal living areas provide architectural depth, while the spacious primary suite includes a walk-in closet and a dedicated sitting area, a rare feature for a home of this era. What truly distinguishes the property are the two detached guest residences, creating a private compound atmosphere. The two-story pool house features a balcony overlooking the courtyard, with a bedroom/office and 2nd laundry access on the first level, and an additional bedroom, full kitchen, and dining area upstairs — ideal for extended family, separated living, or income potential. A separate guest casita includes a bedroom, full bath, kitchenette, and offering flexibility for in-laws, visiting guests, a private office, or creative studio. The layout allows connection when desired and privacy when needed — a rare offering West of the Trail. Original architectural details — hand-carved wood doors, arched passageways, textured plaster walls, a clawfoot tub, parquet and tile floors, and built-in bookcases — preserve the romance of Spanish Mediterranean design while thoughtful updates support modern comfort. Outdoors, the walled courtyard creates a true retreat centered around a heated pool and spa, framed by lush tropical landscaping and a trellis-covered dining area. The front patio adds another inviting gathering space, and ample parking ensures effortless hosting. Other important features are new roofs in 2021, a whole-house generator, and hurricane shutters, offering confidence for year-round or seasonal use. Minutes to Siesta Key Beach and close to Southside Village, this is a rare opportunity to own a versatile Sarasota estate property in one of the city’s most enduring and desirable neighborhoods.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Pam Charron (941-993-3388)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.