Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
6157 MIDNIGHT PASS RD #E23, SARASOTA, FL 34242
$445,000170 Days on yellowkey MLS ID: A4675237
Bed: 1 Bath: 1.0 Liv Area Sq Ft: 748 Built: 1974 Tax: $4,175 (2023)Community: Bay OaksCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$4,175
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2023
Middle School: Brookside Middle
Remarks: **** BIG PRICE REDUCTION *** MOTIVATED SELLER ****Live the Siesta Key lifestyle — right across the street from world-famous SIESTA BEACH—with the added bonus of SHORT-TERM rental / AIRBNB use for maximum flexibility and income potential 1-week rentals allowed and a rental program already in place). This RENOVATED condo is offered FULLY FURNISHED and turnkey, making it easy to enjoy immediately or start generating rental revenue from day one. Located on the 3rd floor makes it very unlikely to get flooded. Inside, you’ll find a bright, coastal feel with LUXURY VINYL FLOORING, fresh coastal paint, modern fixtures/fans, contemporary furnishings & décor, and smart TVs. The kitchen features stone countertops and stainless appliances, and the A/C and water heater are newer. A true standout on Siesta Key—especially in this community—is the IN-UNIT stackable WASHER & DRYER (many units do not offer private laundry). Step outside to the screened patio/porch with a serene setting among cascading oaks and peek-a-boo views of the community pool. Bay Oaks is located on the INTRACOASTAL side of SIESTA KEY and offers amenities owners and guests love, including a heated pool, tennis courts, two convenient elevators in Building E, a walkout pier/dock on the Intracoastal, abundant visitor parking, and a private covered parking spot. Sunrise over the Intracoastal, sunset on Siesta’s sugar-sand beach—this is the life.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Kathy Vandorne (941-275-3934)
435 S GULFSTREAM AVE #206, SARASOTA, FL 34236
$449,000Listed 06/01/2026 9:55PM MLS ID: A4694462
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1304 Built: 1972Monthly Fee: $1,393 Tax: $2,909 (2025)Community: Regency HouseSpa: NoCondo
Taxes:$2,909
Elementary School: Southside Elementary
Tax Year: 2025
Middle School: Booker Middle
Remarks: The Regency House is in the ideal downtown location because it feels like a neighborhood with parkland and the cities bayfront Park to the West as well as Palm Avenue's Tree lined side walked street to the East. The neighbors use the sidewalks and are friendly and active. This building is just far enough from Main Street and all the fun and cultural venues, but just far enough away that it is more peaceful when activities are going on there. Walk the farmer's market and art shows on Saturday mornings and too the Opera and Theaters in the evenings. Many excellent restaurants and entertainment venues line the downtown streets. Walk to Whole foods or Marina Jack's and O'Leary's Cabana bar restaurant less than a half block away as well as stroll the art district walk a block away on your way to Main Street. Hard to beat this location and it is surrounded by some of the most luxurious condominiums in all of downtown but at the most reasonable price level anywhere in the area. With a new resort style pool being installed this summer to replace the dated pool, it will be a relaxing place to enjoy your time or get your exercise doing laps in the extended pool. There are new sunshades and BBQ areas to enjoy as well. We have an exercise area, a party/meeting room with small kitchen for events. The lobby has three convenient entrances and a full-time concierge and manager monitoring the properties security cameras and taking care of the residence owner's requests and needs. Everyone has a nice carport with insulated roofs and some guest spots plus parking on either side of the building on Gulfstream and Palm Avenues. The property is wide and not as crowded together like others in the downtown areas. This is a roomy two bedroom, two-bathroom unit with a nice sized living and dining room as well as the sunny and bright space with opening patio doors to enjoy the morning sunrises or evening moonlight. Attractive and warm wood floors in all the living areas and bedrooms add to the comfortable feel. Bright galley kitchen is easy to prepare your meals or walk five minutes to dine downtown or the neighborhoods quaint cafes, movie theater in the Burns Court area. Hard to beat the convenience to everything including medical services and hospital at short 5 minutes' drive. Airport is less than 15 minutes to pick up your guests, and our airport is quick and easy to get to your gate if you plan to travel. Fine dining on St. Armand's Circle and prime shopping on Lido Key as well as our clean quartz sand beaches like Siesta, Lido and Longboat Keys which are rated consistently among the best in the world! How can you beat all you get at this price level and the lifestyle this condominium will give you? Come take a look and live, the Sarasota Florida Lifestyle!
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: David Butler Jr (941-350-9503)
5654 AARON CT, SARASOTA, FL 34232
$539,900Listed 06/01/2026 1:08PM MLS ID: O6412415
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2805 Built: 2010Monthly Fee: $71 Tax: $5,673 (2025)Community: Oak VistasSingle Family
Taxes:$5,673
Elementary School: Brentwood Elementary
Middle School: McIntosh Middle
Remarks: One or more photo(s) has been virtually staged. Located in a well-established Sarasota neighborhood, this inviting home offers a comfortable and functional layout with warm living spaces that can easily adapt to a variety of lifestyles. The interior features a practical flow that supports both everyday living and entertaining, with plenty of potential to personalize and truly make it your own. Enjoy a convenient location close to shopping, dining, parks, schools, and major roadways, placing you just minutes from everything Sarasota has to offer. Whether you’re looking for a primary residence, seasonal getaway, or investment opportunity, this property delivers an excellent combination of location, comfort, and potential.
Listing is courtesy of: MAINSTAY BROKERAGE LLC (800-583-2914)
Listing Agent: Michael Mcgee (678-846-2807)
4576 BLISS RD, SARASOTA, FL 34233
$395,00076 Days on yellowkey MLS ID: A4685762
REDUCED by $15,000 (3.7%) on 04/17/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1475 Built: 1978 Tax: $3,533 (2025)Community: Sarasota HighlandsSpa: NoSingle Family
Taxes:$3,533
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: Welcome to 4576 Bliss Road a beautifully updated home blending classic Sarasota charm with modern comforts. This inviting 3-bedroom, 2-bathroom residence features a smart split floor plan that offers both privacy and an open flow. Step inside to discover brand new plumbing and stunning luxury vinyl plank flooring throughout, providing durability and style. The bathrooms have been thoughtfully remodeled, combining elegance and functionality to create a spa-like retreat. Outside, enjoy the privacy and security of a fully fenced yard, perfect for outdoor living, entertaining, or play. This home is a wonderful opportunity to experience the timeless character of old Sarasota with contemporary updates that meet today's lifestyle needs. Don't miss out on making 4576 Bliss Road your new sanctuary!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Robert Krasow (941-363-6507)
5880 MIDNIGHT PASS RD #302, SARASOTA, FL 34242
$1,450,000182 Days on yellowkey MLS ID: A4673074
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1642 Built: 1982 Tax: $6,734 (2024)Community: CasarinaCondo
Taxes:$6,734
Tax Year: 2024
Remarks: $50,000 Seller Credit Offered for the Right Offer • Rarely Available Deeded Garage Space • Direct Private Access to Crescent Beach • Updated Interior • 7+ Acres of Lush Landscaped Grounds • Resort-Style Amenities. Welcome to an exceptional opportunity at Casarina where coastal elegance meets resort-style living. For the right offer, the seller is offering a $50,000 credit toward furnishings, customization, or closing-related expenses, creating a unique opportunity for buyers seeking both value and flexibility on Siesta Key. This updated residence also features a rarely available deeded garage space paired with direct private access to Crescent Beach, an increasingly difficult combination to find in today’s market. Positioned on 7+ acres of lush, beautifully landscaped grounds, the community offers an elevated coastal lifestyle with onsite property management, glass elevator access, tennis and pickleball courts, fitness center, beachfront deck, heated pool, spa, and outdoor gathering spaces. Whether you are seeking a full-time residence, seasonal retreat, or investment opportunity with flexible monthly rental potential, this residence offers exceptional value in one of Siesta Key’s most desirable beachfront communities.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Julia Montei (941-702-3098)
7647 SANDERLING RD, SARASOTA, FL 34242
$2,998,00077 Days on yellowkey MLS ID: TB8486392
0 Days Off yellowkey (back on 6/1/2026)
REDUCED by $302,000 (9.2%) on 05/13/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 4006 Built: 1961Monthly Fee: $450 Tax: $23,004 (2025)Community: Sanderling ClubSpa: YesSingle Family
Taxes:$23,004
Remarks: Under contract-accepting backup offers. Accepting Back Up. The Ness House | A Rare Architectural Offering in Sanderling A rare opportunity has emerged on Siesta Key. The Ness House, masterfully designed by renowned architect Tim Seibert, is a timeless expression of the Sarasota School of Architecture — where clean lines, natural light, and a seamless connection to the outdoors define every moment. Privately nestled within the gated enclave of Sanderling, this architecturally significant residence embodies understated luxury, privacy, and intentional design. Expansive walls of glass blur the boundary between indoors and out, inviting sunlight to pour through the interiors while framing tranquil natural surroundings. Thoughtfully designed to capture coastal breezes and effortless livability, the home offers a serene experience that feels both grounded and elevated. Just moments away, the powder-soft quartz sands and turquoise waters of Siesta Key create one of the most celebrated beach lifestyles in the world perfect for morning walks, sunset evenings, and the kind of everyday beauty most only dream of. Now thoughtfully repositioned, The Ness House presents an increasingly rare opportunity to acquire a home of architectural pedigree, location, and lasting design significance at exceptional value. As properties of this caliber become more difficult to find, this offering stands apart for buyers who appreciate authenticity, vision, and timeless architecture. For the buyer who understands design and recognizes true long-term value, this is a moment worth paying attention to. Private showings available by appointment.
Listing is courtesy of: PREMIER SOTHEBY'S INTL REALTY (727-595-1604)
Listing Agent: Janet Moore (813-892-0998)
2442 WOOD ST, SARASOTA, FL 34237
$449,000137 Days on yellowkey MLS ID: A4678152
REDUCED by $23,000 (4.9%) on 05/28/2026
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1279 Built: 1951 Tax: $5,715 (2025)Community: Hudson ParkSingle Family
Taxes:$5,715
Elementary School: Alta Vista Elementary
Remarks: Live in one of Sarasota’s most desirable neighborhoods! Priced to sell. This charming home offers two generously sized bedrooms plus a versatile third space that can serve as a sunroom, office, or private in-law suite/studio. This additional area includes its own bathroom, kitchenette, closet, and separate rear entrance—perfect for guests or rental potential. Inside, you’ll find a cozy layout with a welcoming kitchen nook and comfortable living area, ideal for relaxing and unwinding. The home has been thoughtfully updated with a remodeled kitchen, a newer roof (2018), granite vanity top and sink with brushed nickel fixtures (2020), a brand-new water heater (2025), upgraded lighting (2025), and numerous additional improvements throughout. Enjoy your morning coffee on the inviting front porch or entertain and relax on the back patio. The backyard features a two-car carport, storage sheds, and a newly completed, eye-catching stone fence that adds both ambiance and privacy. Conveniently located just minutes from downtown Sarasota, shopping, dining, and the world-famous Siesta Key Beach, as well as other nearby beaches, this home offers both comfort and accessibility. Additional highlights include RV parking and multi-family zoning, providing excellent flexibility and investment potential. Schedule your private showing today and experience everything this beautiful home has to offer!
Listing is courtesy of: CHROME REALTY LLC (941-363-6300)
Listing Agent: Marni Hayden (941-809-5044)
7732 DONALD ROSS RD W, SARASOTA, FL 34240
$2,250,00030 Days on yellowkey MLS ID: A4692026
REDUCED by $250,000 (10.0%) on 06/01/2026
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3686 Built: 1993Monthly Fee: $369 Tax: $15,084 (2025)Community: Laurel Oak Estates Sec 05Spa: NoSingle Family
Taxes:$15,084
Elementary School: Tatum Ridge Elementary
Remarks: Don’t miss this unique opportunity to own an "outstanding" 4-bedroom, 3.5-bath residence located within the gates of Laurel Oak. This home is ideally positioned on a ½ acre plus premium lake lot with exceptional "natural" privacy, serene water and preserve views from your picture framed lanai. Every home has a story, and this one began in 2020 when it was taken down to the studs and thoughtfully reimagined through a custom renovation—blending timeless design with modern functionality, and delivering a move-in ready experience with lasting peace of mind. The architectural details include crown molding, tray and volume ceilings that highlight the sense of openness and elegance throughout the living spaces. The kitchen has been meticulously designed with expansive counter space and custom cabinetry, creating a natural balance between everyday comfort and functionality. It’s a space that supports daily living with ease while also accommodating those moments that call for gathering and celebration, it is open, practical, and tailored to the flow of everyday life. The transition from the interior living spaces to the exterior spaces creates a true indoor-outdoor lifestyle: inviting, open, and designed for everyday living. Multiple access points from room to room including the Primary & Secondary en-suites extend the living space outward, connecting naturally to the expansive under-cover lanai and pool area showcasing postcard-worthy views with peaceful sightlines. It’s a layout that offers flexibility. Schedule your private showing today to experience this rare Laurel Oak Estates property. Residents have the option to join Laurel Oak Country Club, offering two 18-hole championship golf courses, 12 Har-Tru tennis courts, six pickleball courts, and an active social calendar. Ownership includes moving to the top of the waitlist and (next spot) priority placement on the country club waiting list. Beyond the gates, the location places you near shopping, dining, entertainment, medical facilities, major roadways, and Sarasota’s renowned beaches.
Listing is courtesy of: THE REAL ESTATE STORE (941-685-4224)
Listing Agent: William Kelly (941-685-4224)
8635 MIDNIGHT PASS RD #201C, SARASOTA, FL 34242
$599,99961 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)
117 TUCKER AVE, SARASOTA, FL 34232
$470,00024 Days on yellowkey MLS ID: A4692983
REDUCED by $29,000 (5.8%) on 06/01/2026
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2102 Built: 1930 Tax: $4,991 (2025)Community: Tuckers SubSingle Family
Taxes:$4,991
Elementary School: Fruitville Elementary
Remarks: Step into Sarasota charm with this 1930s character-filled home, where vintage appeal meets everyday flexibility...and no HOA restrictions. This unique 3-bedroom, 3-bath property offers the freedom to truly live your lifestyle: bring your boat, RV, and all your toys with plenty of space to park and play. As you enter, you're welcomed by a screened front porch, leading into a warm and inviting living room featuring a centerpiece fireplace and stunning exposed wood beams. The flexible floor plan includes two bedrooms, a bath, and a loft area upstairs, giving you the option to choose your primary suite on either the first or second floor. The kitchen opens to a backyard deck where a blooming jasmine canopy creates a beautiful setting for morning sunrises. The partially fenced yard offers ample space to create your own private retreat, complete with a garden area, fire pit for cozy evenings, and an additional shed for storage, hobbies, or a workshop. Tucked away on a quiet street, this home feels like a peaceful escape while being just minutes from downtown Sarasota, world-class beaches, and with easy access to I-75. Blending timeless 1930s character with functional living space, this home offers flexibility for guests, multi-generational living, or even rental potential. If you’ve been searching for a property with personality, space, and freedom—this is it.
Listing Agent: Nikki Weiss (941-468-9551)
4536 WEBBER ST, SARASOTA, FL 34232
$324,9503 Days on yellowkey MLS ID: A4695314
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1500 Built: 1979 Tax: $4,006 (2025)Community: Sarasota SpgsSingle Family
Taxes:$4,006
Remarks: Under contract-accepting backup offers. Opportunity, location, and potential all come together at 4536 Webber Street. Offering 3 bedrooms and an attractive entry point into the Sarasota market, this home is perfect for buyers looking to personalize a property while already benefiting from major upgrades like a metal roof installed in 2021, hurricane impact windows, and an expanded paver driveway. Inside, the home offers a clean canvas with original character and endless possibilities to update at your own pace. Whether you're a first-time buyer, seasonal resident, investor, or someone looking to create their ideal Florida home, the layout and location make this a standout opportunity. In this location of Sarasota, you'll enjoy convenient access to downtown dining and entertainment, Sarasota Memorial Hospital, shopping, parks, golf courses, and some of the area's most beautiful Gulf Coast beaches. Spend your weekends exploring, enjoying local restaurants, visiting farmers markets, or taking in Sarasota's vibrant arts and cultural scene. Homes at this price point with major exterior improvements already completed are becoming increasingly difficult to find. Move in now, update over time, and enjoy the flexibility to create a space that fits your vision while investing in one of Sarasota's most desirable areas.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Vincent Diorides (941-720-5717)
2609 DARWIN AVE, SARASOTA, FL 34239
$488,5004 Days on yellowkey MLS ID: A4695205
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1718 Built: 1962 Tax: $1,922 (2025)Community: South GateSingle Family
Taxes:$1,922
Elementary School: Wilkinson Elementary
Remarks: Under contract-accepting backup offers. Experience elevated Sarasota living at 2609 Darwin Ave., Sarasota in this exquisitely updated 3-bedroom, 2-bath pool home with a 1-car garage, ideally located just minutes from renowned Siesta Key Beach, upscale dining, boutique shopping, and vibrant entertainment. Thoughtfully designed for both luxurious everyday living and effortless entertaining, this exceptional residence showcases an expansive open-concept layout with seamless indoor-outdoor flow to a private resort-style setting featuring a sparkling pool with Travertine Pavers, screened patio and elegant firepit lounge area. The designer gourmet kitchen is beautifully appointed with custom cabinetry, luxurious quartz countertops, a farmhouse sink, and newer stainless steel appliances. High-end improvements include a newer roof, newer AC system, hurricane windows and fully owned solar panels providing remarkable energy efficiency with electric costing $46 monthly regardless of usage. The spacious family room with beamed ceiling and hurricane proof skylights overlooking the outdoor oasis, creates the perfect backdrop for relaxing or entertaining guests. Combining modern upgrades, exceptional comfort, and an unbeatable Sarasota location, this move-in-ready residence embodies the finest in Florida luxury living. Don't Miss The Awesome Video.
Listing is courtesy of: BRIGHT REALTY (941-552-6036)
Listing Agent: Geri Scheckner (941-356-0652)
5721 CASA DEL SOL BLVD #3223, SARASOTA, FL 34233
$267,50075 Days on yellowkey MLS ID: A4686344
REDUCED by $7,500 (2.7%) on 04/28/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1313 Built: 1989 Tax: $1,774 (2025)Community: Casa Del Sol Sec IiVilla
Taxes:$1,774
Remarks: RARELY AVAILABLE END-UNIT VILLA WITH PRESERVE VIEWS, OVERSIZED COURTYARD, AND TRUE 2-CAR GARAGE IN HIGHLY DESIRABLE CASA DEL SOL! Positioned in one of the MOST PRIVATE AND SOUGHT-AFTER locations within Casa Del Sol, this exceptional end-unit villa immediately stands apart with tranquil PRESERVE VIEWS, additional green space, and a setting that offers both privacy and serenity. Unlike many homes in the community that overlook neighboring properties, this residence enjoys a peaceful natural backdrop that creates a far more desirable living experience. Inside, the bright and open floor plan offers multiple living spaces designed for both comfort and flexibility. An additional sitting room with WOOD FLOORING and a SKYLIGHT fills the home with natural light and opens directly to the patio, seamlessly blending indoor and outdoor living. The layout features an open living and dining area, kitchen with breakfast bar, and a MAIN-LEVEL PRIMARY SUITE complete with walk-in closet and en-suite bath. This villa also benefits from EXTRA OUTDOOR SPACE rarely found in neighboring units, enhancing both privacy and functionality. The OVERSIZED PRIVATE COURTYARD is ideal for entertaining, relaxing, or enjoying the Florida lifestyle—with no A/C equipment taking up valuable outdoor space. Additional highlights include a TRUE 2-CAR GARAGE, minimal traffic due to its location at the far end of the community, only ONE SHARED WALL, and the added natural light and openness that come with end-unit living. From a long-term ownership perspective, this property delivers exceptional value. Casa Del Sol has actually LOWERED HOA DUES for certain sections in 2026, including this one—an uncommon advantage that reflects strong financial and community management. The A/C is a Rheem and under warranty until 11/15/2028 and the ROOFS were proactively replaced by the HOA approximately 10 years ago for added peace of mind .Hot water heater: Rheem, installed 5/2023>Dishwasher: Frigidaire installed 2023>Hurricane shutters: Mostly metal, some plastic to allow for light into the home. All Screws have been drilled in exterior walls. Upgraded whole-house plumbing system to flow guard gold pipe and fittings. Sunroom was remodeled 2005 with Wood flooring. Residents enjoy access to a community featuring a CLUBHOUSE, FITNESS CENTER, POOL, and TENNIS COURTS, all within a beautifully maintained setting. LOCATION IS EVERYTHING—and this home places you minutes from Sarasota’s most desirable destinations. Conveniently located off Cattlemen Road between US-41 and I-75, you are close to Downtown Sarasota, Siesta Key Beach, Lido Beach, Legacy Trail, Payne Park, Sarasota Art Museum, Colonial Oaks Park, YMCA, Yoder’s Fresh Market, Big Olaf Ice Cream, and more. OPPORTUNITIES LIKE THIS RARELY COME AVAILABLE IN CASA DEL SOL. Plus a 1 year home warranty offered by Seller! Schedule your private showing today and experience the privacy, views and lifestyle this exceptional villa has to offer before it’s gone!
Listing Agent: Rachel Tritschler (941-993-5892)
5830 MIDNIGHT PASS RD #32, SARASOTA, FL 34242
$499,9005 Days on yellowkey MLS ID: A4694962
Bed: 0 Bath: 1.0 Liv Area Sq Ft: 392 Built: 1962 Tax: $2,441 (2025)Community: Jamaica RoyaleSpa: NoCondo
Taxes:$2,441
Remarks: Welcome to Jamaica Royale, a Gulf-side development on Siesta Key, with its award-winning, crystal powder soft sandy beach, just nearby. This studio offers a main-floor villa that has been renovated for comfort and durability. Enjoy the new kitchen with new stainless steel appliances, quartz counters throughout and a new bath. All furnishings have been tastefully replaced with a focus on quality and functionality. The water heater is new, freshly painted, and waiting for its new owner. The location of the rear patio is conveniently near one of three pools. An on-site office offers an optional rental program, so you may generate potential income when not in residence. While you go out your rear patio to the beach, you will pass Jamaica Royale's additional pools, beach cabana and white sands of Siesta Key. The clubhouse offers a full kitchen, a meeting room, on-site association services and rental management. Outside offers barbecue grills, a table and chairs, a lounging area and shuffleboard, a great area to gather with family and friends. Siesta Key offers public transportation to many of the area's local coastal attractions, restaurants, shopping and Sarasota, with all that it offers.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Dennis Girard (941-809-0041)
6204 MIDNIGHT PASS RD #205, SARASOTA, FL 34242
$775,000143 Days on yellowkey MLS ID: A4676979
REDUCED by $4,000 (0.5%) on 04/12/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1173 Built: 1979Monthly Fee: $1,243 Tax: $6,173 (2025)Community: Siesta Dunes BeachCondo
Taxes:$6,173
Remarks: Welcome to your slice of paradise at Siesta Dunes Beach Community. This beautifully maintained 2-bedroom, 2-bath end-unit is located on the second floor and is offered turnkey furnished, making it ideal as a vacation getaway, investment property, or full-time residence. Being an end unit, the condo is filled with extra natural light and offers a charming peek-a-boo ocean view to remind you just how close you are to the beach. Enjoy peace of mind with recent upgrades, including a newer AC, newer roof, and brand-new impact windows (2025). The unit includes a covered parking space and the community provides private beach access and beach chairs, so you’re ready to enjoy the Siesta Key lifestyle from day one. With weekly rentals allowed, this property offers excellent rental potential in a highly desirable beachfront community. Whether you’re relaxing on the sand or generating income, this Siesta Dunes condo checks all the boxes for coastal living which will not disappoint.
Listing Agent: Christine Green (941-914-2463)
1100 BENJAMIN FRANKLIN DR #305, SARASOTA, FL 34236
$550,000Listed 06/01/2026 1:35PM MLS ID: A4695506
Bed: 1 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 918 Built: 1976 Tax: $5,481 (2025)Community: Lido Surf & SandCondo
Taxes:$5,481
Elementary School: Pine View School
Remarks: Rare private open-air courtyard patio with breathtaking Gulf and beach views! One of only a select handful of residences within Lido Surf & Sand to offer this highly sought-after outdoor living space, this furnished 1-bedroom, 1.5-bath beachfront condominium delivers a lifestyle opportunity rarely available on Lido Key. Whether enjoying your morning coffee while watching the waves roll in or relaxing at sunset with the sound of the Gulf in the background, the expansive patio creates an outdoor experience that few condominium residences can match. Inside, the residence features a bright and inviting floor plan with updated flooring, spacious living and dining areas, abundant natural light, and beautiful water views. Offered furnished, the condo is ready to enjoy immediately as a primary residence, seasonal retreat, or investment property. Offered furnished and with a history of seasonal rental demand, the property also presents an attractive opportunity for buyers seeking a beachside investment, seasonal residence, or personal coastal retreat. Lido Surf & Sand is a premier Gulf-front community offering residents an exceptional collection of amenities, including private beach access, a beachfront heated pool and spa overlooking the Gulf, fitness center, covered parking, private storage, bicycle storage, elevators, grilling areas, shuffleboard courts, beautifully maintained walking paths and sidewalks, multiple gathering and entertaining spaces, on-site property management, and secure building access. The location is equally impressive. Situated just moments from world-famous St. Armands Circle, residents enjoy convenient access to an incredible selection of restaurants, boutique shopping, cafes, galleries, and year-round events. Downtown Sarasota, Marina Jack, cultural attractions, and Sarasota-Bradenton International Airport are all within easy reach. Opportunities to own one of the community's rare patio residences are exceptionally limited. Combining beachfront living, spectacular Gulf views, resort-style amenities, strong rental appeal, and an unbeatable location near St. Armands Circle, this is coastal Florida living at its finest.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Dillon Hegarty (443-534-1666)
5108 SANDY SHORE AVE, SARASOTA, FL 34242
$1,050,00010 Days on yellowkey MLS ID: A4694309
1 Days Off yellowkey (back on 5/26/2026)
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1681 Built: 1960 Tax: $4,305 (2025)Community: Sara SandsSpa: NoSingle Family
Taxes:$4,305
Remarks: Capturing the essence of “location, location, location,” this canal-front pool home is ideally situated on a quiet cul-de-sac street on the desirable north end of Siesta Key. Offering 2 bedrooms & 2 bathrooms, the well-maintained, albeit dated, residence presents an exceptional opportunity to update or build the custom waterfront estate of your dreams. Set in a premier location where the true value lies in the land and lifestyle, the property has not experienced flooding and offers the rare combination of tranquility, boating access, and proximity to the beach. Just 1.1 miles away are the world-renowned white quartz sand beaches of Siesta Beach, with Beach Access #5 conveniently located at the west end of Siesta Key Village. The Village is known for its vibrant island atmosphere, featuring an eclectic mix of restaurants, boutiques, nightlife, and entertainment. For boating enthusiasts, the home offers an 18 minute +/- boat ride via the Grand Canal to Sarasota Bay, with direct access to Big Pass and the Gulf of Mexico. Whether you envision relaxing poolside, spending carefree days at the beach, enjoying boating adventures, or embracing the vibrant island lifestyle, this property offers endless possibilities in one of Sarasota’s most coveted waterfront locations.
Listing Agent: Angela Adams (941-809-9760)
3424 TANGLEWOOD DR, SARASOTA, FL 34239
$899,00010 Days on yellowkey MLS ID: A4694194
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3147 Built: 1962Monthly Fee: $17 Tax: $8,708 (2025)Community: South GateSingle Family
Taxes:$8,708
Remarks: Welcome to this lakefront retreat with a private guest suite with direct access to Phillippi Creek located in Southgate! This is a rare opportunity to own private waterfront with access to scenic Phillippi Creek and the Intracoastal Waterway. This exceptional property combines timeless design, modern upgrades and Florida indoor-outdoor living, all with no history of hurricane water intrusion, according to the owner. From the moment you arrive, the home’s curb appeal impresses with a circular driveway, paver walkways, an additional paver parking pad, mango and avocado trees and a fully fenced setting surrounded by lush, mature landscape. Enter through stunning French doors with stained glass into a bright, tropical-inspired entry. Inside, the open-concept living space is expansive and inviting, anchored by a gas fireplace and enhanced by updated windows that fill the home with natural light. The chef’s kitchen is functional and stylish, featuring a curved stone countertop and bistro-height seating, Murano glass pendants and recessed lighting, a six-burner natural gas cooktop and stainless-steel appliances, including a Bosch dishwasher. Designed for entertaining, the outdoor living area is exceptional. Enjoy an expansive paver patio with a tranquil wall-mounted fountain and a summer kitchen with a gas grill, refrigerator, sink, single gas burner and an exterior-vented commercial-grade hood. The backyard overlooks serene views of Lake Seclusion and the dock. Watch the ducks, herons, egrets, cormorants and leaping fish. The primary suite is a private sanctuary, spacious, light-filled and surrounded by glass sliders opening to the patio with peaceful water views. Features include dual oversized walk-through closets, an elegant en suite bath with split vanities, granite countertops, a jetted soaking tub on an elevated platform and a walk-in shower with glass block detail and water closet. Further highlights in this wing are two more large bedrooms with a shared bath, walk-in shower and pedestal sink. Another standout feature of this home is the fully equipped multigenerational living suite/home office/artist studio complete with a private entrance and courtyard, separate air-conditioning system and kitchen with appliances. The suite has a living room/bedroom combo and a full bath with a new tile shower and linen closet. Connecting the guest suite with the three bedrooms and two baths is a spacious butler's pantry with a full-size refrigerator and wine chiller as well as a washer, dryer, utility sink and extensive storage. The oversized attached garage has an updated automatic door opener motor, cabinets and shelving. In the backyard are the Rinnai tankless gas water heater, a well-fed irrigation system, exterior lighting, a private outdoor shower and a small storage shed. The roof was replaced in 2022 and one of two AC units was replaced the same year. This is more than a home; it’s a private retreat offering flexibility, functionality and exceptional waterfront living plus the option of income production. It is minutes from downtown, the beach and shopping without the inconvenience of bridges or seasonal traffic. The desirable neighborhood is quiet and stable with mature trees lining the gently curving street. Remarkably, this house has had only three owners, a sign of how special it is to live there.
Listing Agent: Cindy Taliaferro (941-894-7269)
1750 BENJAMIN FRANKLIN DR #10G, SARASOTA, FL 34236
$1,175,000119 Days on yellowkey MLS ID: A4680259
REDUCED by $25,000 (2.1%) on 04/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1548 Built: 1970 Tax: $9,085 (2025)Community: Key Tower SouthCondo
Taxes:$9,085
Remarks: ****There is nothing left to do. Nothing to imagine. Completed in 2022, everything has been upgraded and transformed into the most modern luxury. This high-floor corner residence on Lido Beach in the Key South Tower building has been completely transformed—from ceilings to floors—into a home where every high-end creature comfort is already in place and water views unfold from every window. The building is so modern, so perfectly updated and completed that it even has its own hurricane/surge protection system surrounding the building-- unique and impressive. You must see this condo's extraordinary views in day and at night!!! ****Panoramic vistas stretch across the Gulf of Mexico, Sarasota Bay, the Ringling Bridge, and downtown Sarasota, creating a constantly shifting backdrop of light, water, and skyline. Set within a Lido Beach building that has already been elevated to the highest modern building standards, this residence offers peace of mind. The HOA’s abundant reserves reinforce the sense of security -- owners love living here. Inside, porcelain tile flows throughout, complemented by all-new ceilings and modern lighting that set a sophisticated, contemporary tone. ****The kitchen is both elegant and functional, featuring abundant new wood cabinetry, quartz countertops, and new appliances—designed for everything from casual mornings to elevated entertaining. The primary suite is a private sanctuary, framed by water views and finished with the finest luxury tile. It offers a walk-in closet, an ensuite bath with a walk-in shower, and thoughtful storage. The guest suite is equally impressive, with new tile, a walk-in closet, and beautiful views of the Intracoastal Waterway and downtown Sarasota. Spacious enough for a king bed, it also features its own walk-in shower, making it ideal for guests who appreciate comfort and privacy. ****Beyond the residence, Key Tower South has been fully reimagined, with the lobby and common areas completely renovated in 2025. Residents enjoy 220 feet of private Gulf frontage, a heated beachfront pool, expansive sundeck, direct beach access, saunas, a fitness room, library, bike storage, and on-site management—resort-level amenities without the crowds. ****This is not simply a condo. It is a fully realized beachfront lifestyle—elegant, effortless, and complete. Call now for a private showing. Prefer to experience it from afar? Drone footage and immersive fly-throughs are available.
Listing is courtesy of: COLDWELL BANKER REALTY (941-907-1033)
Listing Agent: Meredith Van Vaals (612-716-4784)
2531 WISTERIA ST, SARASOTA, FL 34239
$2,497,0004 Days on yellowkey MLS ID: A4694903
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 3203 Built: 2026 Tax: $4,502 (2025)Community: South GateSpa: YesSingle Family
Taxes:$4,502
Remarks: Perfectly positioned in the heart of the highly sought-after South Gate neighborhood, this exceptional new construction residence by Park Residences LLC masterfully blends timeless architecture, designer-curated finishes, and state-of-the-art functionality to create an extraordinary family retreat. Offering 5 bedrooms, 5 bathrooms, and an uncompromising level of craftsmanship throughout, every detail of this luxury home has been thoughtfully designed for elevated everyday living. From the moment you enter, you are welcomed by refined interiors highlighted by 7 1/4-inch white oak engineered hardwood flooring flowing throughout, complemented by level 4 drywall finishes, custom feature walls, and stunning Visual Comfort lighting and ceiling fans, hand-selected by our interior designer. A dramatic living area showcases a sleek horizontal fireplace flanked by custom shelving creating a warm yet elegant focal point ideal for entertaining or relaxing with family. The gourmet chef’s kitchen is both elegant and functional, featuring custom white oak soft-close cabinetry, exquisite quartzite surfaces, a custom-built pantry, and a premium suite of luxury appliances. Culinary enthusiasts will appreciate the Thermador 48-inch built-in smart French door refrigerator/freezer with integrated custom paneling, Thermador dishwasher with custom cabinetry front, Fisher & Paykel 48-inch induction range with convection oven, and Sharp smart microwave drawer. Every element has been selected to combine beauty, innovation, and performance seamlessly. A custom staircase with 1 1/4-inch solid wood stair treads, beautifully stained and brushed, adds architectural character while leading to spacious secondary living areas and bedrooms. Custom closets throughout the home provide exceptional organization and storage, while pre-wiring for sound allows for effortless integration of modern smart-home living. Built with superior quality and efficiency in mind, the residence features PGT impact windows and Thermatru doors, spray foam insulation in the roof deck, garage, and lanai ceilings, and a durable steel tile roof with a lifetime warranty. Two Daikin 15 Seer heat pump air conditioning systems with Nest thermostats provide year-round comfort, while two water heating systems — including a tankless instant hot water heater and a 55-gallon Rheem Gladiator with leak detection — ensure convenience and peace of mind. Outdoor living is equally impressive with a resort-inspired heated saltwater pool and spa featuring a gunite finish, elegant waterline tile, sun shelf, autofill system, and expansive marble pool decking. A 6ft fully fenced creates a private oasis perfect for entertaining, pets, or family gatherings. Combining luxury finishes, advanced construction quality, and impeccable design in one of the area’s most desirable family neighborhoods, this remarkable South Gate residence offers a rare opportunity to own a truly remarkable new construction home where sophistication, comfort, and functionality come together effortlessly.
Listing is courtesy of: SARASOTA TRUST REALTY COMPANY (941-366-1619)
Listing Agent: Renee Preininger (941-400-4235)
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