Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
8977 MIDNIGHT PASS RD #222, SARASOTA, FL 34242
$589,900117 Days on yellowkey MLS ID: A4676582
58 Days Off yellowkey (back on 4/17/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1093 Built: 1974 Tax: $5,552 (2025)Community: Sunrise Cove Sec 3Condo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,552
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Under contract-accepting backup offers. Luxury Waterfront Living Spectacular Views, Resort-Style Amenities Wake to breathtaking sunrises over Little Sarasota Bay and the Intracoastal Waterway. This fully remodeled and furnished 2-bedroom, 2-bath condo offers 1,093 square feet of refined coastal living where the views are the true centerpiece. The Residence Thoughtfully renovated in 2024, this residence blends the modern finishes with timeless coastal elegance. The open living and dining areas are bathed in natural light and perfectly positioned to capture sweeping water views, creating an inviting space for both everyday living and entertaining. Features include: 2 Bedrooms, 2 Bathrooms 1,093 Square Feet Panoramic Bay & Intracoastal Views Luxury Vinyl Flooring (2024) New Stainless-Steel Appliances (2024) New Hot Water Heater (2024) New A/C System (2025) Quartz Countertops Offered Fully Furnished with Upscale Furnishings & Accessories Move-In Ready Resort-Style Waterfront Community Enjoy an amenity-rich lifestyle designed for relaxation, wellness, and recreation: Tennis & Pickleball Courts Two Heated Pools-Including an Olympic-Size Pool with Lap Lanes Clubhouse with Pool Table and Ping Pong Fitness Center with Weight & Exercise Equipment Boat Docks Available for Lease Waterfront Setting with Direct Intracoastal Access An Unmatched Coastal Location Turtle Beach directly across the road Shuttle stop providing easy access to Siesta Beach and Siesta Village World-class beaches, boating, dining, and shopping just minutes away The Lifestyle This home is all about the views- sparkling water, passing boats, and unforgettable sunrises enjoyed from the comfort of your living space. Whether as a primary residence, seasonal retreat, or investment property, this condo delivers a luxury waterfront lifestyle with effortless ease.
Listing is courtesy of: PETER D DONAHUE LICENSED REAL ESTATE BROKER (239-206-0740)
Listing Agent: Peter Donahue (239-206-0740)
2344 BAY ST W, SARASOTA, FL 34237
$1,350,000176 Days on yellowkey MLS ID: A4671233
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1930 Built: 2026 Tax: $3,809 (2023)Community: Poms Park 3Spa: NoSingle Family
Taxes:$3,809
Elementary School: Alta Vista Elementary
Tax Year: 2023
Remarks: Pre-Construction. To be built. Discover exceptional value in this brand-new, single-story 3-bedroom, 2.5-bath modern home located within Sarasota city limits, allowing for weekly rentals, perfect as a full-time residence, vacation retreat or income-producing property. Step inside to find imported Italian cabinetry, flooring and fixtures, hurricane impact windows and sleek contemporary finishes that define understated elegance and lasting quality. The open-concept layout offers seamless flow between living spaces, ideal for entertaining and everyday living. Your private outdoor oasis awaits with an in-ground pool, outdoor shower and spacious patio for relaxing or hosting guests under the Florida sun. Perfectly positioned just steps from The Legacy Trail and only minutes to downtown Sarasota, parks, shopping, dining and the area’s world-renowned beaches, this home offers the best of modern design and unbeatable convenience. Sarasota living at its finest, whether you’re investing, vacationing or settling in, this opportunity won’t last!
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Rinat Sikdar (941-993-9292)
5302 LAS ROSAS, SARASOTA, FL 34242
$725,000275 Days on yellowkey MLS ID: A4659614
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1184 Built: 1962Monthly Fee: $4 Tax: $3,190 (2024)Community: Sarasota BeachSingle Family
Taxes:$3,190
Tax Year: 2024
Remarks: Welcome to Palm Island, the Heart of Siesta Key!! Palm Island is an Island on an Island, located a short walk to World Famous Sugery Sands of Siesta Key Beach (Beach Access 10) and Siesta Village. With only one small humpback bridge on & off, this beachy neighborhood is a quiet oasis that is close the beach, restaurants and nightlife that makes this area so desirable. Great opportunity to build your dream home or use the current home as an investment or just enjoy the Island lifestyle. Current home has 2 bedrooms, 2 baths and a 2-car garage. Terrazzo floors throughout. The fenced back yard is a Tropical Paradise for taking in the soothing Gulf Breeze.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Dan Miller (941-376-7442)
1647 SIESTA DR, SARASOTA, FL 34239
$1,690,00031 Days on yellowkey MLS ID: A4684901
Bed: 5 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 3032 Built: 2025 Tax: $17,778 (2025)Community: BayviewSpa: YesSingle Family
Taxes:$17,778
Elementary School: Southside Elementary
Remarks: Welcome to this stunning coastal home with elevator, featuring 5 bedrooms, 2.5 bathrooms, and 3,023 square feet of living space. Additional opportunity to add bathrooms with modification add-on with the builder. From the moment you enter, you'll be captivated by the open floor plan, pool view, and fantastic design. This dazzling property, boasts an open floor plan that features high ceilings, natural light, and high-quality finishes throughout. The home features a modern and elegant kitchen with top-of-the-line Cafe' appliances, quartz countertops, and custom cabinetry. The primary bedroom located on the upper level can be accessed by elevator is a true sanctuary, offering a plush and peaceful retreat. It boasts vaulted ceilings, en-suite bathroom that includes a soaking tub and a separate shower that's great for unwinding after a long day. The room also features a generously sized walk-in closet with abundant space for storage and organization as well as a private terrace. On the second floor you will find three vast bedrooms, with plenty of closet space for added convenience and comfort. One of the most notable features of the second floor is the sizable sundeck and balcony, which are attached to both bedrooms. The laundry room is conveniently located on the second floor as well. The spacious bonus room offers endless possibilities, from an office, den, playroom, media center or a home gym. This home has two patios with an outdoor area with a large pool and hot tub that seamlessly blend the indoor and outdoor living with meticulously planned landscaping. Situated between Siesta Key and Downtown Sarasota, you will have easy access to some of the best beaches, restaurants, and shopping in the area. Whether you are looking for a day at the beach, a night out on the town, or a quiet evening at home, this home has everything you need.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
1365 HARBOR DR, SARASOTA, FL 34239
$5,495,000151 Days on yellowkey MLS ID: A4672827
REDUCED by $490,000 (8.2%) on 04/11/2026
Bed: 4 Bath: 4.5 Gar: 6 Liv Area Sq Ft: 4978 Built: 2018 Tax: $34,839 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$34,839
Remarks: A striking triumph of modern architecture and engineering, this three-story contemporary estate in Harbor Acres—Sarasota’s most coveted neighborhood—stands as a bold statement of design, innovation, and uncompromising luxury. Designed by renowned architect Mark Sultana of DSDG Associates, the residence is a masterwork where precision and artistry converge. From the moment of entry, soaring ceilings, expansive walls of glass, and a dramatic Italian floating staircase set the tone. Natural light fills the interiors, enhancing a layout designed for both impact and livability. The main level is anchored by an open-concept great room and a chef’s kitchen of exceptional caliber. A full suite of Miele appliances—including induction cooktop, built-in espresso maker, warming drawers, dual microwaves, and a full-height wine tower—is paired with Dekton countertops and custom Westwood cabinetry. A concealed butler’s pantry with Sub-Zero refrigeration enhances functionality. Living and dining areas flow seamlessly to a covered terrace with a summer kitchen and thermally modified wood ceiling overlooking the private grounds. The north wing is dedicated to a dual-owner’s suite—two private retreats connected by a spa bath with floating vanities, dual rain showers, soaking tub, heated towel racks, and custom Italian closets. One suite is currently configured as a refined office. The second living level offers a library/media room that can convert to a two-room guest suite, an additional bedroom suite, and two full baths for comfort and privacy. Outdoors, a resort-style setting unfolds with a dramatic 50-foot heated pool and spa, covered lounge areas, and lush bamboo for privacy. A separate one-bedroom guest house with full bath, coffee bar, and mini refrigerator provides independent accommodations. The rooftop terrace captures sweeping panoramic views of Sarasota Bay, the Ringling Bridge, Longboat Key, Siesta Key, and the downtown skyline—an exceptional setting for sunset gatherings. Additional features include Crestron-controlled lighting, shades, and audio, integrated speakers, five Luma security cameras with remote access, and two climate-controlled garages for up to six vehicles with epoxy floors, storage, and a gym opening to the pool terrace. A rare architectural statement offering elevated design, privacy, and location just minutes from downtown Sarasota and the Bayfront.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Kim Ogilvie (941-951-6660)
783 BIRDSONG LN, SARASOTA, FL 34242
$999,900179 Days on yellowkey MLS ID: A4670796
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1905 Built: 1973 Tax: $11,733 (2025)Community: Siestas Bayside Waterside SouthSpa: NoSingle Family
Taxes:$11,733
Remarks: Experience Coastal Living at its finest in this turnkey-furnished, three-bedroom, two-bath retreat tucked away on a quiet cul-de-sac in a private community just minutes from the beach! This home features the ULTIMATE OUTDOOR living space with numerous updates offering the perfect blend of style, comfort, and low-maintenance lifestyle. As you step through the front door, you’re greeted by a bright open floor plan enhanced by tasteful coastal décor and tile flooring. Multiple dining and entertaining spaces flow effortlessly into the spacious family room, ideal for relaxing or hosting guests, with direct access to the stunning pavered pool area. The beautifully appointed kitchen features stainless steel appliances, abundant counter space, and a convenient breakfast bar for additional seating. Retire to the serene primary suite which offers a walk-in closet and a well-designed bath with dual sinks, and opens directly to the INCREDIBLE new 21' x 24' covered lanai—an inviting extension of your living space. This IMPRESSIVE private outdoor oasis features pavers, remote-controlled ceiling fans, sconce lighting, and a remarkable sunset overlooking the relaxing pool complete with dramatic lighting for that special ambience. Enjoy privacy and seclusion in your backyard retreat which is fully enclosed with a 7 foot vinyl fence. An outdoor shower adds convenience after a day at the beach. The exterior has been expertly refreshed with new hardiplank siding, fresh paint, and attractive stone accents. A premium landscaping package includes full irrigation, shell for low maintenance, and landscape lighting to set the perfect atmosphere. Additional upgrades elevate peace of mind and efficiency: a 2024 roof, hurricane-rated windows and doors, new pool pump, attic insulation, new garage door and opener, and a newly pavered front walkway and driveway with a charming sitting area and extra parking. This beautiful home reflects pride of ownership and detail with so many updates and most important no flooding during the storms! Ideally located close to Siesta Key Village, just one mile from world-renowned Siesta Key Beach, and near shopping, dining, and ODA school, this home is perfectly suited as a primary residence, vacation retreat, or exceptional rental opportunity!
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Lori Lockhart, Pa (941-724-0595)
2848 WEBBER PL, SARASOTA, FL 34232
$359,90072 Days on yellowkey MLS ID: A4681884
0 Days Off yellowkey (back on 3/7/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1184 Built: 1976 Tax: $2,021 (2025)Community: Webber Heights SubSingle Family
Taxes:$2,021
Elementary School: Brentwood Elementary
Middle School: McIntosh Middle
Remarks: Under contract-accepting backup offers. Looking for Land?? Rare opportunity to own 1/3 acre West of 75 with NO DEED RESTRICTIONS and a private POOL! Located on a quiet dead end street, this 3-bedroom, 2-bath home offers 1,184 square feet of living space, and is perfectly positioned on a generous .33-acre lot along Lake Tern. Already equipped with a detached workshop/shed adding valuable flexibility for hobbies, storage, or a dedicated workspace. Enjoy the privacy of a large screen enclosed, partially covered patio surrounding the pool with fountain that provides the perfect place to cool off and entertain, while the large yard offers plenty of additional space for pets, gardening, or future improvements. Inside, the home features a comfortable living area, dining space, and functional kitchen ready for your personal updates. The primary bedroom includes an en-suite bath with garden tub and step in shower, with two additional bedrooms and a second full bathroom. The expansive backyard is a rare find, offering endless possibilities for outdoor living, expansion, or storing your toys without HOA limitations. Needs a little elbow grease so bring your tools and toys!
Listing is courtesy of: MAPP REALTY & INVESTMENT CO (941-379-2448)
Listing Agent: Mandy Mapp (941-650-6009)
2829 WILFRED REID CIR, SARASOTA, FL 34240
$2,475,00060 Days on yellowkey MLS ID: A4683188
1 Days Off yellowkey (back on 3/17/2026)
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 6573 Built: 1999Monthly Fee: $369 Tax: $15,482 (2025)Community: Laurel Oak EstatesSpa: YesSingle Family
Taxes:$15,482
Elementary School: Tatum Ridge Elementary
Remarks: Under contract-accepting backup offers. PERFECTLY POSITIONED ON 2 LOTS PROVIDING YOU A VERY PRIVATE SETTING ON 1.33 ACRES * QUALITY BUILT BY William McGinnis Custom Homes and BUILT TO LAST with a TIMELESS OLD WORLD DESIGN * This is NOT a cookie cutter home * Ideal for the discerning buyer who will appreciate the SPACIOUS LIVING, QUALITY CRAFTSMANSHIP & ENDURING ELEGANCE * Pride of ownership shows * The MAIN HOUSE features a Formal Living Room and Formal Dining Room, a Library/Den/Office with Custom Built-ins * The Gourmet Kitchen is a Chef’s delight with Graber Wood Cabinets, Granite Counter-tops, Sub-Zero Refrigerator, Viking Gas Stove, Double Ovens, Warming Drawer and Triple Sinks * Your Kitchen is open to the SPACIOUS Family Room with Coffered Ceilings, Wood Beams, Crown Molding and a BEAUTIFUL FIREPLACE * The Primary Suite is a true retreat featuring a Sitting Room, Custom Walk-in Closets, Marble Flooring and a Spa-style Bath * The ONLY UPSTAIRS Living Space is the 2nd En-suite Bedroom with a Walk-in Closet & Balcony * The GUEST CASITA has 2 En-suite Bedrooms with Walk-in Closets & a Full Sauna – perfect for your guest's privacy. All of this wraps your OUTDOOR OASIS showcasing a LARGE, CAGED POOL & SPA PLUS AN OUTDOOR KITCHEN and an ABUNDANCE OF COVERED LANAI * This is the perfect home for entertaining family & friends or for simply relaxing in your slice of paradise * OVERSIZED Gated Motor Court with 4 Garage Bays – one is detached, air conditioned and ideal as a Flex-space * Quiet side street * LARGE Circular Driveway * 6573-/- sqft a/c INCLUDES the Main House & Guest House & the 4th Detached Garage or Flex-space * A special opportunity behind the gates of Laurel Oak Estates, an outstanding Country Club community where nature and elegance abound. Offering 800+ acres of beauty and serenity, it is easy to see why some of the most discerning homeowners call Laurel Oak home. Optional club with outstanding facilities including 2 championship courses, 12 Har-Tru tennis courts, Junior Olympic-sized heated pool, & beautiful clubhouse, golf shop and attended locker rooms. Enjoy reciprocity with the Bird Key Yacht Club (boating, tennis, fitness, dining & social events) and quick easy access to I-75, downtown, UTC Mall, World Famous Siesta Key beach and our other beautiful beaches * One look & you'll fall in love * Golf is optional, but if you want a golf membership, BUY THIS HOME AND GO TO THE FRONT OF THE LINE FOR A GOLF MEMBERSHIP. One look & you'll fall in love *
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Glenn Brown (941-342-6464)
4726 OLD FARM RD, SARASOTA, FL 34233
$649,00080 Days on yellowkey MLS ID: A4681786
0 Days Off yellowkey (back on 4/17/2026)
Bed: 3 Bath: 2.0 Gar: 3 Liv Area Sq Ft: 2192 Built: 1999Monthly Fee: $55 Tax: $4,932 (2025)Community: OakleafSpa: NoSingle Family
Taxes:$4,932
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: Under contract-accepting backup offers. From the natural preserve-style entrance to Oakleaf, featuring large estate-sized lots, playground, and a community filled with families who take pride in ownership, this home offers an exceptional Sarasota lifestyle. The sense of place is highlighted by the community’s iconic mosaic mermaid riding a sea turtle and a tropical vacation-style mural, welcoming you home each day. Quality built by Todd Johnston Homes, this move-in ready, immaculate pool home features a 3-bedroom, 2-bath split floor plan plus a den/office, volume ceilings, and an open-concept layout designed for both comfort and entertaining. The chef’s kitchen showcases granite countertops, new cabinet doors, a breakfast bar, and opens seamlessly to the spacious family room. The private owner’s suite offers a walk-in shower, garden tub, dual vanities, and a large walk-in closet. Living areas and bedrooms wrap around a private screened pool with an oversized lanai, delivering true indoor-outdoor Florida living. The fully fenced backyard provides a peaceful wooded view, mature custom landscaping, and a private yard well. Additional features include a 3-car garage with extra-high garage doors and ceilings, custom garage floor finish, and beautiful curb appeal. Recent major upgrades include a new tile roof installed July 2025 and a new Trane XR14 14.3 SEER2 4-ton single-stage heat pump system installed August 2025. Why wait or compare to new construction? This home delivers everything buyers seek in a new build, including open layout, modern finishes, high ceilings, a pool, and a premium lot, without construction delays, change-order costs, or uncertainty, and to mirror new construction peace of mind, a one-year American Home Warranty is included with purchase.
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Alan Macloughlin (941-780-8628)
1915 TULIP DR, SARASOTA, FL 34239
$2,649,999151 Days on yellowkey MLS ID: A4673707
REDUCED by $50,000 (1.9%) on 04/03/2026
Bed: 4 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 2935 Built: 2025 Tax: $6,145 (2025)Community: Hartland ParkSpa: YesSingle Family
Taxes:$6,145
Remarks: Under contract-accepting backup offers. Welcome to 1915 Tulip Drive – a beautiful Single Story home you will love! This new construction Modern Coastal Single Story home is located West of the Trail in the preferred Zone X (unshaded) with elevated storm protection and easy access to Siesta Key beaches, Southside Village and Downtown Sarasota. Built strong and stylish by Majestik Homes, this 4 bedroom 4 bathroom residence blends architectural elegance with energy efficiency and storm-ready construction. From the moment you enter through the grand 9-foot doors, you’re greeted by soaring ceilings, expansive glass, and a seamless indoor-outdoor flow that captures Florida living at its finest. The open floor plan centers around a designer great room, a chef’s kitchen outfitted with premium Thermador gas appliances and a dining room that is perfect for intimate dinners and larger gatherings. Designed with both performance and sustainability in mind, this home features energy-efficient lighting, appliances, and insulation systems that reduce consumption without sacrificing comfort. With 2 efficient air conditioning units and a tankless gas water heating system you will enjoy energy efficient heating and cooling year-round. Built with an emphasis on strength and safety, this residence offers peace of mind with a finished floor height of 26’ above sea level and materials selected to withstand Florida’s toughest storms. Every detail—from the block construction to the impact-rated windows—has been thoughtfully engineered to provide long-lasting security and a safe haven for your family. Beautifully staged and thoughtfully designed, this home showcases artwork from some of the local area’s most inspiring artists. Easy to show – you won’t want to miss this exceptional opportunity.
Listing is courtesy of: MAJESTIK REALTY, INC (941-363-6080)
Listing Agent: Michael Hankin (941-504-4337)
407 OHIO PL, SARASOTA, FL 34236
$1,000,000206 Days on yellowkey MLS ID: A4667604
1 Days Off yellowkey (back on 3/3/2026)
Bed: 5 Bath: 0.0 Liv Area Sq Ft: 1826 Built: 1940 Tax: $11,173 (2023)Community: Rhodes & Hale SubApartment
Taxes:$11,173
Middle School: Booker Middle
Remarks: Under contract-accepting backup offers. 3 UNITS in Laurel Park! This income-producing opportunity is in the coveted Downtown Historic District of Laurel Park, Sarasota. This beautifully renovated and meticulously maintained triplex blends timeless character with proven financial performance, offering the perfect combination of lifestyle and investment potential. Currently operating as an established Airbnb with Superhost status and professional management in place, this property provides steady, verifiable income with strong year-over-year performance and the flexibility to continue as a high-yield short-term rental or transition to long-term tenants for predictable cash flow. The triplex features three charming, fully furnished units—two front units with two bedrooms and one bathroom each, and a one-bedroom, one-bathroom rear unit. Each includes private driveways, off-street parking, patios, and either in-unit or shared laundry. Situated on an exceptional flag lot with dual frontage on both Laurel Street and Ohio Place, this property offers rare privacy, accessibility, and redevelopment potential. The lot’s size and configuration make it ideal for a future custom residence, offering one of the most desirable build opportunities within Sarasota’s downtown core. Financially, the property has a consistent and transparent performance record, generating $111,599 in 2023, $106,893 in 2024, and a projected $103,000 in 2025. Importantly, these figures already reflect reduced occupancy, as the owners reserve the property multiple times per year for family use. Without that usage, the income potential is expected to reach or exceed $120,000 annually, offering clear upside for an investor focused on maximizing returns. With stronger marketing, repeat-guest programs, and continuous availability, this property’s income could grow substantially while remaining a largely hands-off investment. This triplex stands out not only for its returns but also for its flexibility. Investors can enjoy immediate passive income with management and future bookings already in place, or occupy one unit and rent the others to offset ownership costs. The property’s prime location within the National Historic District of Laurel Park enhances its long-term value, offering walkable access to Sarasota’s Bayfront, Selby Gardens, Main Street dining, shopping, and the city’s renowned arts and theater venues. Laurel Park’s historic charm, walkability, and strong rental demand make it one of Sarasota’s most stable and appreciating neighborhoods for both investors and homeowners alike. With its combination of proven rental history, turnkey condition, desirable lot, and premier downtown location, this property represents a rare opportunity to own an asset that delivers reliable income today and exceptional upside tomorrow. Whether held as a passive income generator, a personal retreat with investment benefits, or the site of a future luxury home, this triplex embodies the best of Sarasota’s lifestyle, history, and growth potential. Don’t miss your chance to own this exceptional property in one of Sarasota’s most sought-after neighborhoods—where historic character meets lasting investment value.
Listing Agent: Ryan Skrzypkowski (941-328-8307)
1614 STAFFORD LN #1206, SARASOTA, FL 34232
$234,900106 Days on yellowkey MLS ID: TB8464986
5 Days Off yellowkey (back on 3/19/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1456 Built: 1971Monthly Fee: $620 Tax: $1,059 (2024)Community: Village Green Forest Lake 12Spa: NoVilla
Taxes:$1,059
Remarks: Under contract-accepting backup offers. Rare Opportunity in a 55+ Community Welcome to 1614 Stafford Lane in beautiful Sarasota! While this vibrant neighborhood is designed for 55+ living, this particular home offers a unique exception open to residents under 55. This spacious property combines the best of both worlds: the comfort and serenity of a well-maintained 55+ community, paired with the freedom to enjoy it at a younger age. Whether you’re looking for a seasonal retreat, a peaceful full-time residence, or a smart investment, this is a rare chance to step into a sought-after lifestyle ahead of time. Enjoy access to the community’s inviting amenities, beautifully landscaped surroundings, and a welcoming atmosphere all while being close to Sarasota’s world-class beaches, dining, and cultural attractions. Don’t miss this opportunity to be part of a community that usually isn’t available unless you're 55+.
Listing is courtesy of: FLORIDA EXECUTIVE REALTY (813-327-7807)
Listing Agent: Eva Flores Espinoza (619-451-7997)
1313 SIESTA BAYSIDE DR #1313D, SARASOTA, FL 34242
$639,000101 Days on yellowkey MLS ID: A4678960
REDUCED by $30,000 (4.5%) on 04/17/2026
Bed: 1 Bath: 1.5 Gar: 1 Liv Area Sq Ft: 959 Built: 1988 Tax: $6,865 (2025)Community: Gulf & Bay Club BaysideCondo
Taxes:$6,865
Remarks: Welcome to 1313 Siesta Bayside Drive in Gulf & Bay Club Bayside, a beautifully updated 2-bedroom, 1.5-bath condo offered turnkey furnished and ideally suited as a personal beach retreat or high-performing investment property with weekly rental flexibility and consistent future bookings already in place. This light-filled residence features tasteful coastal updates and a serene pond waterview, complemented by a private single-car garage, driveway parking, and additional guest parking conveniently located across the street. Enjoy deeded beach access to world-famous Siesta Beach, renowned for its bright white quartz sand and crystal-blue Gulf waters, just a short walk away, while the Siesta Key Village shops and restaurants are an easy drive, bike, or golf cart ride. Gulf & Bay Club Bayside is a gated, resort-style community offering two heated pools, tennis and pickleball courts, walking paths, a fishing pier, fitness center, clubhouse, BBQ and picnic areas, and lush tropical landscaping, delivering the perfect blend of relaxed island living and strong income potential in one of Siesta Key?s most desirable communities.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Shane Lewis (941-685-3252)
5830 MIDNIGHT PASS RD #705, SARASOTA, FL 34242
$1,240,000151 Days on yellowkey MLS ID: TB8451655
0 Days Off yellowkey (back on 4/6/2026)
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1285 Built: 1976 Tax: $10,763 (2024)Community: Jamaica Royale Tower IiSpa: NoCondo
Taxes:$10,763
Remarks: Under contract-accepting backup offers. Welcome to your beachfront oasis! VIDEO WALK THROUGH AVAILABLE UPON REQUEST. Discover your perfect getaway in this beautifully refreshed 7th-floor condo, offering stunning balcony views of the Gulf of Mexico. With 1,285 square feet of living space, this fully furnished property features 2 bedrooms and 2 full bathrooms—all you need to bring is your bathing suit and toothbrush! The light-filled great room seamlessly connects the kitchen, living area, and dining space, making it ideal for relaxation and entertaining. Recent upgrades include new HVAC (3/2026), elegant touches like solid surface countertops, a stylish backsplash, and pendant lighting in the kitchen, along with a freshly painted interior and new lighted ceiling fans, The primary bathroom boasts a new solid surface vanity, a backlit mirror, a glass shower door, and designer tiled flooring, just to name a few. After a day at the beach, take a refreshing dip in the pool or unwind on your spacious balcony while watching the sunset. With an onsite management team, your beach retreat promises to be both profitable and hassle-free. This condo has a robust rental history, making it a fantastic investment opportunity for vacation rentals. Residents and guests of Jamaica Royal benefit from deeded assigned parking and access to private beach chairs. Located in a prime area, you can easily explore local restaurants and enjoy live music, all just a trolley or bike ride away. Don’t miss your chance to own this incredible piece of paradise!
Listing is courtesy of: PLUMLEE GULF BEACH REALTY (727-595-7586)
Listing Agent: Beverly Schroeder (727-422-5779)
1825 PAR PL, SARASOTA, FL 34240
$447,500284 Days on yellowkey MLS ID: A4659448
0 Days Off yellowkey (back on 4/16/2026)
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2269 Built: 1969 Tax: $2,697 (2024)Community: Sarasota Golf Club Colony 4Single Family
Taxes:$2,697
Remarks: Under contract-accepting backup offers. PRICED TO SELL! Bring your decorative touches to this beautiful home. You will love the mother in-law suite which includes a bathroom with a slide in shower, access to the laundry room and close to the main kitchen as well. It has it's own portable A/C unit. Was converted from garage in 2011. The house comes with New A/C 2023, new roof in 2020, electric panel in 2021, lanai & pool rescreened, hurricane windows 2008 and the New septic tank has been installed! Swim in the heated pool and enjoy the large beautiful fenced back yard and fruit trees. No HOA or CDD fees!
Listing is courtesy of: SHOWTIME REALTY (941-822-0890)
Listing Agent: Sherri Urfer (941-320-7849)
5362 SHADOW LAWN DR, SARASOTA, FL 34242
$4,950,000178 Days on yellowkey MLS ID: A4667008
REDUCED by $445,000 (8.2%) on 04/04/2026
Bed: 3 Bath: 4.0 Gar: 3 Liv Area Sq Ft: 4294 Built: 2023Monthly Fee: $17 Tax: $36,494 (2024)Community: Siesta IslesSpa: YesSingle Family
Taxes:$36,494
Remarks: Under contract-accepting backup offers. Experience elevated coastal living in this award-winning “Marlin Model” by Nutter Custom Construction, perfectly positioned on Siesta Key’s coveted Grand Canal. Completed in 2023 and showcased as the builder’s signature home, this completely custom Yacht-Modern residence blends refined elegance, contemporary design, and exceptional waterfront functionality. With 4,294 sq. ft. under air and 6,405 total sq. ft., this home offers 3 ensuite bedrooms (please note gym can be converted into 4th bedroom), 3 full baths, 2 half baths—including a dedicated pool bath—plus multiple flexible indoor and outdoor living spaces ideal for relaxed luxury and entertaining. Floor-to-ceiling glass doors reveal sweeping water views and seamless indoor-outdoor flow. Elevated construction and smart-home technology offer modern security and peace of mind. No water intrusion or damage during recent hurricanes. The chef’s kitchen is a standout, featuring a 10-ft waterfall island, European white dolomite counters, hidden walk-in pantry, Wolf appliances, built-in coffee system, under-cabinet toe lighting, and formal dining with wine cooler and ice maker. The primary suite is a private retreat with dual walk-in closets, hidden entry doors, freestanding soaking tub, oversized designer shower and steam room, and private outdoor shower garden. Outside, enjoy resort-style living with a multi-level pool and raised spa with infinity spillover, expansive lounging deck, covered living and dining with motorized screens, full outdoor kitchen, turf backyard with putting green, and multiple terraces. For boating enthusiasts, the property offers 104 ft of waterfront, a new concrete seawall, 104 ft of composite dock, two Golden Gear boat lifts with remotes (20,000lb & 5,000lb), water and shore power. Hop on your boat and be in the Gulf in less than 15 minutes. This property has received prestigious recognition, earning Best Custom Home, Best Kitchen, and Best Staircase in the Parade of Homes awards — reflecting exceptional craftsmanship and design distinction. The oversized 2.5-car garage provides excellent storage and functionality, offering space for a golf cart or the option to create a golf simulator setup. Located in Siesta Isles with a voluntary HOA, less than one mile to Siesta Key Beach and moments to Siesta Village by golf cart or bike. Click on the Virtual Tour Link to get a behind the scenes look! ** Furniture negotiable
Listing is courtesy of: NCC PROPERTIES LLC (941-924-1868)
Listing Agent: Morgan Marziali (941-806-7214)
139 S WASHINGTON DR, SARASOTA, FL 34236
$14,950,000263 Days on yellowkey MLS ID: A4661401
Bed: 5 Bath: 6.5 Gar: 3 Liv Area Sq Ft: 7817 Built: 1936 Tax: $158,866 (2025)Community: Saint Armands Div John Ringling EstatesSpa: YesSingle Family
Taxes:$158,866
Remarks: Where HISTORY Meets MODERN LUXURY @ "Casa del Carnevale," an exquisite waterfront estate, situated in the prestigious St. Armands Key, the neighborhood of John Ringling Estates. This home seamlessly blends history with modern luxury, offering views of the Sarasota Waterway and Bay with a historic designation. Casa del Carnevale presents a rare opportunity to own an esteemed historical property. Offered for only the fifth time in its storied history, this exceptional estate combines Old World architectural charm with contemporary opulence. The home underwent an extensive renovation, with meticulous attention to detail and craftsmanship, utilizing top-tier materials and artisanship. Expanded from 4,000 to nearly 10,000 square feet under roof, and featuring over 7,800 square feet of air-conditioned space, Casa del Carnevale preserves its original charm while offering a reimagined layout that exceeds modern luxury standards. Set on three sprawling lots, 30,000+ square feet, the estate boasts 171 feet of waterfrontage, a private dock lift, a floating lift for jet skis and kayaks, and breathtaking views of Sarasota Waterway. The lush, meticulously designed tropical landscaping creates a private oasis that feels like you are walking in Selby Gardens on St. Armands. The residence includes five bedrooms and six and a half baths across two spacious levels with an elevator. Multiple terraces provide perfect outdoor retreats and entertaining areas, all complemented by stunning garden water vistas, a central courtyard, and an elegant 65' saltwater pool and spa with arched spraying fountains and iridescent glass tiles. Other luxury features include a three-car garage, elevator, nanny’s quarters, walk-in wine room, billiards room, office, and custom impact-glass arched windows designed to maximize unobstructed views. The chef’s kitchen boasts premium finishes, top-of-the-line appliances, a 5-Star La Cornue range and hood from France, featuring gas or electric ovens (kitchen art). Sub-Zero refrigerators, a Bosch dishwasher, a Miele microwave, a Miele built-in coffee machine, a stand-alone beverage refrigerator, and a stand-alone ice maker. Throughout the home, exposed beams, warm wood tones, natural stone, custom ironwork, Pecky Cypress wood throughout, and curated artwork create an inviting, sophisticated atmosphere. Offering furniture (negotiable under separate contract), and instant enjoyment to create everlasting memories, Casa del Carnevale is a rare and exquisite blend of history, elegance, and modern comfort on one of Sarasota’s most coveted waterfront estates. EASY TO SHOW. CASA DEL CARNEVALE IS A MUST-SEE IN PERSON TO FULLY APPRECIATE.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Judy Kepecz-Hays (941-587-1700)
825 OSPREY AVE #108, SARASOTA, FL 34236
$495,00057 Days on yellowkey MLS ID: A4684762
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1985 Tax: $5,113 (2025)Community: Central ParkCondo
Taxes:$5,113
Remarks: Welcome to Central Park I in the heart of downtown Sarasota, where sophisticated design meets an exceptional location. This beautifully renovated 2-bedroom, 2-bath residence presents an effortless, move-in-ready opportunity in one of Sarasota’s most desirable boutique buildings. Inside, the thoughtfully reimagined interior features a bright, open-concept layout complemented by refined finishes and curated upgrades throughout. The designer kitchen is both striking and functional, showcasing elegant quartzite countertops and backsplash paired with premium Italian appliances by Bertazzoni and Fulgor Milano—a space equally suited for everyday living and stylish entertaining. The kitchen flows seamlessly into the main living and dining areas, creating an inviting atmosphere filled with natural light. Just beyond, a sunlit alcove provides a serene place to relax and unwind after a day enjoying all that downtown Sarasota has to offer. The living space opens to a southern-facing terrace overlooking Hudson Bayou and the community pool, while a covered portion allows for comfortable year-round outdoor enjoyment. The spacious primary suite serves as a private retreat, featuring elegant French doors leading to a bright east and south-facing terrace. The renovated en-suite bath offers a spa-like experience with a walk-in shower, stone vanity and a generous walk-in closet. A split guest bedroom and full bath provide ideal privacy and flexibility for visiting guests, a home office, or additional living space. Ideally situated in the sought-after Central Park I building, residents enjoy a coveted downtown lifestyle just moments from Southside Village, Palm Avenue’s renowned galleries, Marina Jack, Selby Gardens, and walking distance to the vibrant Sarasota Bayfront. Whether as a full-time residence or a refined seasonal retreat, this fully furnished, impeccably renovated condominium offers a rare blend of luxury, comfort, and walkable coastal living.
Listing Agent: Bibi-Ann Allard, Pa (941-685-0422)
679 NORSOTA WAY, SARASOTA, FL 34242
$7,500,00032 Days on yellowkey MLS ID: A4687909
1 Days Off yellowkey (back on 4/16/2026)
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3788 Built: 1926 Tax: $23,415 (2025)Community: Bay IslandSingle Family
Taxes:$23,415
Remarks: Tucked away on highly sought-after Bay Island, just over the North Siesta Key Bridge, 679 Norsota Way is a rare and extraordinary opportunity to own a piece of Sarasota’s architectural history or create something entirely new. Built in 1926, this Mediterranean Revival estate with Spanish Colonial influences sits gracefully on an expansive 2/3-acre lot, offering timeless character, generous scale, and unmatched potential. With 150 feet of deep water bayfront, the homesite is one of the largest on Bay Island's coveted northern edge. The 3,788 sqft two-story residence features 4 bedrooms, 3.5 bathrooms, a dedicated office, and a flexible bonus room, with all bedrooms thoughtfully positioned on the second level. The primary suite is exceptionally spacious and captures breathtaking views overlooking Sarasota Bay, the Ringling Bridge, and the downtown skyline, a daily backdrop that defines true coastal living. Original details and soft historic charm are present throughout, providing a warm and inviting foundation ready to be reimagined. The home has been flood remediated but not remodeled, offering a clean slate for restoration or renovation while preserving its architectural integrity. Importantly, the property is not historically designated, presenting a rare level of flexibility. For those seeking new construction, this exceptional 2/3-acre homesite offers the opportunity to start fresh without the constraints of an HOA or significant building restrictions, an increasingly uncommon advantage in such a premier location. No deed restritions or grand oaks constrain construction. Beyond the main residence, a secondary structure provides a two-car garage and hobby space, ideal for storage, creative pursuits, or future customization. Perfectly positioned just 10 minutes to downtown Sarasota and 5 minutes to the beach, this property blends privacy, proximity, and prestige in one of the area’s most coveted neighborhoods.
Listing is courtesy of: COLDWELL BANKER REALTY (941-388-3966)
Listing Agent: Nick Gard (941-500-4273)
5661 MIDNIGHT PASS RD #401, SARASOTA, FL 34242
$469,90099 Days on yellowkey MLS ID: A4678954
REDUCED by $5,100 (1.1%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1012 Built: 1975 Tax: $4,629 (2025)Community: White Sands VillageCondo
Taxes:$4,629
Remarks: Welcome to coastal living at its best in White Sands Village, a desirable waterfront community ideally located in the middle of Siesta Key and 1 mile from The Village. This charming 2-bedroom, 2-bath end-unit condominium (no flood damage), offering added peace of mind and ease of ownership. The community is surrounded by lush tropical landscaping and features a clubhouse and sparkling community pool, creating a relaxed island atmosphere. White Sands Village offers water access with Gulf-front amenities and boat slips available via waitlist, perfect for boating enthusiasts. This property may be used as a rental or income-producing investment with a minimum 2-week rental period, making it an excellent option for seasonal use or short-term rental opportunities. Ideally located across the street from world-famous Siesta Key Beach, along with nearby restaurants, shopping, and entertainment, plus convenient on-and-off island access. Whether you’re looking for a full-time residence, vacation retreat, or rental investment, this property delivers the best of the Siesta Key lifestyle.
Listing Agent: Lisa Blakeney (616-795-6545)
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