Location: Sarasota , 34236
Do Not Show Listings
1862 6TH ST, SARASOTA, FL 34236
$749,00071 Days on yellowkey MLS ID: O6380883
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1419 Built: 1925 Tax: $8,926 (2025)Community: Inwood Park First AdditionSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,926
Elementary School: Alta Vista Elementary
High School: Booker High
Tax Year: 2025
Middle School: Booker Middle
Remarks: One or more photo(s) has been virtually staged. Live, invest, and work in the heart of downtown Sarasota. This beautifully renovated 1925 triplex is located in Gillespie Park and offers exceptional flexibility with short-term rentals allowed. Fully updated inside and out, the property presents a rare turnkey opportunity in one of Sarasota’s most desirable and walkable neighborhoods. The exterior has been meticulously improved with new landscaping, stylish pavers, artificial turf, a new privacy fence, updated roof, updated electric meters, energy-efficient windows and doors, and a modern sand-finish exterior. These upgrades provide strong curb appeal and long-term durability. All three units have been completely remodeled and are offered fully furnished. Renovations include new drywall, new subflooring, updated electrical systems, newer HVAC units, modern flooring, new kitchen cabinets, sleek appliances, updated bathroom vanities, toilets, showers, and fresh interior paint throughout. Each unit is move-in ready and designed for low maintenance and operational efficiency. The location offers unmatched convenience. Ideal for investors seeking strong income potential, or for an owner-occupant looking to live in one unit while renting the others. One or more photo(s) have been virtually staged.
Listing is courtesy of: MILLENNIA REALTY (407-271-0754)
Listing Agent: Jordan Ruvalcaba (407-271-0754)
33 S PALM AVE #701, SARASOTA, FL 34236
$1,995,000202 Days on yellowkey MLS ID: A4666950
REDUCED by $200,000 (9.1%) on 04/14/2026
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2229 Built: 2024Community: The DemarcayCondo
Taxes:$0
Elementary School: None
High School: None
Tax Year: 2024
Middle School: None
Remarks: Situated in the cultural core of downtown Sarasota and completed in 2024, this 3-bedroom, 3.5-bath residence is impeccably maintained, and captures a rare blend of refined design and effortless downtown living. Bathed in natural light and defined by clean architectural lines, it’s a home that celebrates both art and simplicity, while placing the city’s vibrant rhythm at your doorstep. With 11-foot ceilings, expansive walls ideal for displaying artwork, and partial water views from the terrace, the main living space, and owner’s suite, the interiors feel open, tranquil, and beautifully composed. The chef’s kitchen—featuring Miele appliances, a gas cooktop, a waterfall island, custom Italian cabinetry, and a walk-in pantry—blends precision and beauty in equal measure. Windows above the sink welcome natural light and offer a serene view of tree-lined Palm Avenue, while the adjacent terrace is perfect for morning coffee or sunset cocktails. Well-curated fixtures, Lutron shades throughout, integrated surround sound, and a bespoke owner’s closet highlight the home’s thoughtful design. Included are two EV-ready parking spaces and a separate temperature-controlled storage space. Residents enjoy 24-hour staffed service and an 18th-floor rooftop amenity level with a fitness center, elegant club room, and saltwater pool—each with panoramic city and bay views, creating a peaceful oasis above the lively city below.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Lisa Allen (312-848-1636)
111 S PINEAPPLE AVE #1021, SARASOTA, FL 34236
$1,299,00013 Days on yellowkey MLS ID: A4688715
Bed: 2 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1575 Built: 2019 Tax: $18,357 (2025)Community: Mark Sarasota CondoSpa: YesCondo
Taxes:$18,357
Elementary School: Southside Elementary
High School: Sarasota High
Middle School: Brookside Middle
Remarks: Experience refined urban living in this beautifully updated residence, complete with two dedicated parking spaces, featuring two bedrooms, 2.5 baths, and a versatile bonus room. Thoughtfully designed with an open concept layout, the home seamlessly blends modern style and everyday functionality, enhanced by high end builder finishes and custom upgrades throughout. The flexible den, ideal as a library, media room, or home office, offers endless possibilities. At the heart of the home, the gourmet kitchen impresses with an induction cooktop, quartz countertops, custom backsplash, and under cabinet lighting, perfect for both everyday living and entertaining. The spacious owner’s suite serves as a private retreat, featuring direct terrace access, a large walk in closet, additional custom storage, and a spa inspired bathroom with dual vanities, an oversized countertop, and a glass enclosed walk in shower with a rain showerhead. Each bedroom includes its own en suite bath, and the additional half bath is both stylish and convenient for guests. Storage is thoughtfully maximized with custom built closets, cabinetry, and shelving throughout. Luxury upgrades include porcelain flooring, designer light fixtures, premium wireless ceiling fans, an Ecobee smart thermostat, and remote controlled Hunter Douglas window treatments. Residents also benefit from community EV charging stations. The expansive terrace offers ample room for outdoor dining and lounging, with sweeping views of downtown Sarasota and the bay, perfect for taking in stunning sunsets. Residents of The Mark enjoy exceptional amenities, including a stylish club room and lounge, a state of the art fitness center, and an outdoor entertaining area with grilling stations, fire pit, and a 65 foot heated saltwater pool and spa. Located in the heart of downtown Sarasota’s vibrant arts and dining district, the building offers 24 hour security and on site management. Built in 2019, The Mark is known for its sleek contemporary design and premier location just steps from Main Street’s boutiques, restaurants, and popular farmers market. Schedule your private showing today.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Mairead Smialek (847-334-4848)
555 QUAY CMNS #1101, SARASOTA, FL 34236
$7,199,0008 Days on yellowkey MLS ID: A4689860
Bed: 4 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 4223 Built: 2024Community: Ritz-Carlton Residences, Sarasota BaySpa: YesCondo
Remarks: One or more photo(s) has been virtually staged. Pre-Construction. To be built. With three exposures spanning Sarasota Bay to the downtown skyline, Residence A offers exceptional natural light from sunrise to sunset. The open-concept great room flows to three private terraces, including one with an outdoor kitchen, ideal for entertaining. A spacious kitchen with walk-in pantry, cozy den and well-appointed guest suites – two with terrace access and one with stunning corner water-to-skyline views – complete the layout. The primary suite features dual walk-in closets and a spa-inspired bath with soaking tub, double vanities and an oversized shower. In The Ritz-Carlton tradition, residents enjoy 24-hour concierge, valet, in-residence dining and exceptional amenities. Only two of these highly sought-after floor plans remain. Estimated completion: December 2026.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Julia Decastro (941-812-5176)
101 S GULFSTREAM AVE #12C, SARASOTA, FL 34236
$449,000174 Days on yellowkey MLS ID: A4668919
Bed: 1 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 985 Built: 1974 Tax: $5,464 (2025)Community: Dolphin TowerCondo
Taxes:$5,464
Remarks: Welcome to the 101 Condominium located in the heart of Sarasota. This 1 bedroom, 2 bathroom condo has spectacular views of Downtown Sarasota and views of the bay through the city skyline. Located on the 12th floor, this unit has been fully remodeled from the studs including all electrical and plumbing. As you enter the home you are greeted with ceramic tile flooring, a spacious living area, and hurricane resistant sliding glass doors that lead out to your private balcony with city views. The kitchen features granite countertops, stainless steel appliances, and elegant cabinetry. The master bedroom features engineered hardwood flooring with an updated bathroom attached. The unit comes with a private parking space that is covered underneath the building. The 101 Condominium is conveniently located in Downtown Sarasota just across the street from Marina Jack, O'Leary's Tiki Bar & Grill, and Bayfront Park along with all that Sarasota has to offer. St. Armand's Circle, Lido Key Beach, and Longboat Key are all within close proximity.
Listing is courtesy of: KW COASTAL LIVING III (941-900-4151)
Listing Agent: Laura Rode (941-724-9957)
301 S OSPREY AVE, SARASOTA, FL 34236
$1,099,00084 Days on yellowkey MLS ID: A4680127
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 3320 Built: 1914 Tax: $13,510 (2024)Community: Pos Sub Of Blks G & HApartment
Taxes:$13,510
Remarks: Prime Investment Opportunity in Laurel Park – Fabulous 4-Plex with Exceptional Income Potential! Discover your next smart investment in the heart of Laurel Park, one of Sarasota’s most desirable and historic neighborhoods. Just three blocks from vibrant Main Street and minutes from the city’s renowned Gulf Coast beaches, this charming 4-unit multifamily property offers a rare chance to own premium real estate in a high demand location. The property consists of two separate buildings, each featuring an upper and lower 1-bedroom, 1-bath apartment, with ample off-street parking for tenants. All units are currently leased to reliable annual tenants, ensuring immediate income. For investors seeking to maximize returns, this property offers significant upside as a short-term rental, with the potential to generate substantially higher income through weekly bookings in a vacation-friendly market.
Listing is courtesy of: QUEST PROPERTIES INC (941-504-1111)
Listing Agent: Timothy Bloch (941-504-1111)
1350 MAIN ST #1501, SARASOTA, FL 34236
$939,000188 Days on yellowkey MLS ID: A4668214
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1364 Built: 2007Monthly Fee: $1,424 Tax: $11,511 (2024)Community: 1350 Main ResidentialSpa: YesCondo
Taxes:$11,511
Remarks: Experience luxury living in the heart of downtown Sarasota at 1350 Main Street. This stunning 15th-floor residence offers sweeping views of the city skyline and Sarasota Bay, all just steps from world-class dining, shopping, and cultural attractions. This end unit is being sold turnkey, with high end finishes throughout. The open-concept layout is filled with natural light, featuring floor-to-ceiling impact windows, 2 balconies, a modern kitchen with premium finishes, and spacious living areas perfect for entertaining. Enjoy resort-style amenities including a rooftop pool on level 6, fitness center, club room, 24-hour concierge, and secure parking garage. Embrace the vibrant urban lifestyle with the elegance and comfort you deserve.
Listing is courtesy of: HORIZON REALTY INTERNATIONAL (941-238-0953)
Listing Agent: Bill Trier (941-586-6372)
1860 7TH ST, SARASOTA, FL 34236
$749,00042 Days on yellowkey MLS ID: A4685678
REDUCED by $20,000 (2.6%) on 04/14/2026
Bed: 4 Bath: 0.0 Liv Area Sq Ft: 1568 Built: 1969 Tax: $7,172 (2025)Community: Gillespie ParkApartment
Taxes:$7,172
Remarks: * Tremendous opportunity to own your own duplex in GILLESPIE PARK – LIVE IN ONE SIDE AND RENT OUT THE OTHER ! Or just rent out both of them ! * Fabulous opportunity to tear down and build your own New Single Family Home in the Downtown area with an Additional Dwelling unit for Income – Zoned DTN + During the time of preparing all the Architectural plans and going through the permitting process – you are collecting rent all along the way ! * You could even add a pool between the 2 New Buildings for Fun for all ! *Right across street from Sarasota’s Own 10 acre Wooded Oasis in the middle of Downtown Sarasota – GILLESPIE PARK ! Featuring Tennis Courts , walking trails , a pond that winds through the park , Wonderful playground and even a separate Dog Park ! * Rear unit has been staged and is quite beautiful ! Streetside unit has been leased by same tenant for last 20 years ! Do you think he likes it here ? And he would love to stay ! * 2 – 2 Bedroom /1 Bath units situated on an oversized 7500 square foot lot. 1568 sq. ft. with laundry out building with big Back yard to Roam & Play. *Both A/c units are new – 1 is 6 months old and the other is 18 months old * New Roof in 2018 ! and All new Sewer and Water lines to building within last 3 years! *To have access to all that Downtown Sarasota has to offer within just a few blocks is amazing ! You literally have 65 restaurants within a 10 block radius. Who needs a car anyway ? * The Bay Trolley is just a few blocks away as well taking you all the way to Lido Beach and back for Free without ever having to park a car! * And Don’t Forget the ever popular Legacy Walking and Bicycle Trail and Payne Park also just a few blocks away. * And One Last Huge Benefit - You are literally only 6 blocks from the Ultra Amazing new 53 acre Bay Park ! Which you just have to see and experience to believe. *YOU must experience the Downtown Lifestyle to really appreciate what our Great City has to offer !
Listing Agent: Frank Lambert (941-920-1500)
424 BOWDOIN CIR, SARASOTA, FL 34236
$14,750,000386 Days on yellowkey MLS ID: A4646393
1 Days Off yellowkey (back on 4/14/2026)
Bed: 5 Bath: 5.5 Gar: 3 Liv Area Sq Ft: 5882 Built: 2023Monthly Fee: $25 Tax: $131,499 (2024)Community: Lido ShoresSpa: YesSingle Family
Taxes:$131,499
Remarks: Under contract-accepting backup offers. Set against Sarasota’s coveted bayfront in Lido Shores, this extraordinary waterfront estate captures sweeping views of Sarasota Bay, the downtown skyline, Ringling Bridge, and City Island, offering an unparalleled luxury lifestyle with effortless access to boating, beaches, and downtown Sarasota. More than a residence, this is a statement property—an iconic example of West Indies–inspired architecture executed with exceptional craftsmanship and modern sophistication. A private gated entry introduces a home where over $1 million in enhancements and more than 2,000 hours of custom design are evident throughout. Advanced smart home automation allows seamless global control, blending innovation with refined living. The custom front door opens to a dramatic foyer and a great room defined by a coffered ceiling, media wall, linear fireplace, and expansive bay views. The dining space features a quartz-topped bar with wine storage and flows into a chef’s kitchen appointed with Thermador appliances, a large floating island with quartz waterfall edges, and a walk-in pantry with an additional Bosch refrigerator. The primary suite is a tranquil sanctuary with floor-to-ceiling glass, sliders, and breathtaking water views. Two custom walk-in closets complement a spa-inspired bath featuring floating vanities, a soaking tub, a custom multi-head shower, and sliders leading to a private Zen garden with an outdoor shower. A sculptural staircase and glass-enclosed wine wall lead to an upper-level loft with a wet bar and waterfront terrace. A refined office with custom built-ins and four en-suite guest bedrooms, each with custom closets, projector screens, and private balconies, ensure comfort and privacy throughout. Outdoors, the estate transforms into a resort-style waterfront retreat. An infinity-edge pool with sun shelf, in-pool table, and cascading spa anchors the setting, surrounded by multiple seating areas, a firepit, and an outdoor shower. The fully equipped outdoor kitchen—featuring a smoker, grill, wok, and side burner—makes alfresco entertaining effortless, while a spiral staircase leads to an upper terrace with panoramic views. The newer deepwater dock is designed for serious boating, offering a 20,000-pound boat lift, jet ski lift, water and power, ambient lighting, and a dedicated fishing area. With direct access to Sarasota Bay just steps from the backyard, this property delivers exceptional boating and waterfront living. Additional features include a three-car garage, two laundry rooms, an elevator, a garage drop zone, and a hidden utility closet. The home is fully integrated with Control4 automation, security cameras, a 48-kilowatt generator, 20-kilowatt battery backup, high-end audio-visual systems, automated shades, circadian lighting, outdoor theater, app-controlled pool and irrigation, Wi-Fi-enabled appliances, EV charger prewiring, Starlink backup internet, motion-activated lighting, and voice control via Josh AI. Lido Shores is one of Sarasota’s most sought-after and architecturally significant waterfront communities, offering residents exclusive access to the north end of Lido Beach and close proximity to St. Armands Circle, Longboat Key, City Island, and downtown Sarasota. This remarkable bayfront estate is an architectural triumph, designed for sophisticated entertaining, advanced living, and extraordinary waterfront luxury.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Joel Schemmel (941-587-4894)
1155 N GULFSTREAM AVE #306, SARASOTA, FL 34236
$1,749,00011 Days on yellowkey MLS ID: A4689553
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1770 Built: 2017 Tax: $13,593 (2025)Community: Vue Sarasota BaySpa: YesCondo
Taxes:$13,593
Remarks: Stunning Sarasota Bay and Marina Jack views, combined with newer construction, make this residence at The VUE a standout opportunity in downtown Sarasota. Ideally positioned, this luxury condominium offers exceptional walkability just steps from premier dining, shopping, and cultural attractions. Designed to live like a true three-bedroom home, the den has been thoughtfully enclosed with a door and custom Murphy bed—ideal for guests or a private office. A private elevator foyer welcomes you into a bright, open living space where expansive impact-rated sliders frame unobstructed water and city views along with spectacular sunsets. Immaculate interiors showcase porcelain tile throughout the main living areas, while engineered hardwood flooring adds warmth to the primary and second bedrooms. In the primary suite, a custom walk-in closet with built-ins is complemented by an additional reach-in closet, offering excellent storage and organization. The sleek, modern kitchen blends style and function with premium stainless-steel appliances, an induction cooktop, Nolte European cabinetry, and Culligan water treatment at the sink. Everyday convenience is enhanced by a utility room featuring an LG washer/dryer tower and additional storage. Residents enjoy a full suite of amenities including a resort-style pool and spa, state-of-the-art fitness center, rooftop dog park, concierge, valet service, and secure building access. Included with the residence are two garage parking spaces and a private storage unit. Sharing a coveted downtown location alongside the Ritz-Carlton and The Westin—home to its popular rooftop bar—this address offers unmatched access to Sarasota’s vibrant lifestyle. From here, the iconic Ringling Bridge is easily walkable without crossing major roads, making it simple to enjoy the scenic waterfront any time of day. An exceptional combination of luxury, location, and breathtaking views.
Listing Agent: Mackenzie Longueuil (941-961-4023)
1800 BENJAMIN FRANKLIN DR #B308, SARASOTA, FL 34236
$1,300,00012 Days on yellowkey MLS ID: A4689391
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1700 Built: 1996 Tax: $7,388 (2024)Community: L Elegance On Lido BeachCondo
Taxes:$7,388
Remarks: Discover the pinnacle of coastal elegance on Lido Beach! This stunning TURNKEY FURNISHED, 3-bedroom, 2.5-bath residence at L'Elegance is move-in perfect and showcases a sweeping 39-foot terrace with breathtaking views of South Lido Park, the iconic Ringling Bridge, and the Sarasota skyline. Gleaming new wood-look tile floors flow seamlessly throughout, adding a fresh, modern warmth to every room. The thoughtfully designed kitchen features crisp white cabinetry, gleaming granite countertops, a ceramic tile backsplash, and stainless steel appliances. The expansive primary suite serves as a true sanctuary, featuring a generous walk-in closet, an indulgent soaking tub, a separate glass shower, and dual vanities crafted for everyday luxury. The spacious second bedroom, currently enjoyed as a stylish den and study, offers the added bonus of direct terrace access — perfect for morning coffee or an inspiring work-from-home setting with stunning views. A versatile third bedroom with its own half bath provides ideal flexibility for guests or additional living needs. A dedicated interior laundry room with a full-size washer and dryer adds effortless practicality to daily living. L'Elegance sets the standard for resort-style community living, offering two lighted Har-Tru tennis courts, a heated Olympic-size pool perched above the pristine shoreline, and an elegant Gulf-view social lounge ideal for entertaining. A fully equipped fitness center with men's and women's saunas keeps wellness front and center, while around-the-clock security at the guard-gated entrance provides peace of mind. Secure under-building parking rounds out the convenience. Situated on 400 feet of exclusive Gulf of Mexico beachfront, pet-friendly and perfectly poised between luxury and nature, this residence embodies the very best of the Sarasota coastal lifestyle. St. Armands Circle, Longboat Key, and Downtown Sarasota are just minutes away, offering an unrivaled mix of acclaimed dining, boutique shopping, recreation, and cultural experiences. Don't miss this opportunity to call L'Elegance home — consistently recognized as Lido Beach's most coveted address.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Ann Martin (941-356-7717)
707 S GULFSTREAM AVE #602, SARASOTA, FL 34236
$799,000633 Days on yellowkey MLS ID: T3544842
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1247 Built: 1974 Tax: $7,976 (2023)Community: Essex HouseCondo
Taxes:$7,976
Tax Year: 2023
Remarks: Florida living at its finest! Fully renovated, turnkey 6th floor unit with views of the bay! No expense was spared: gourmet-style kitchen, sleek contemporary finishes and glazed porcelain plank tile throughout, spa inspired bathrooms, oversized closets, and new windows throughout. The enormous sun deck and pool provide resort-style amenities including a gazebo, grilling area, well equipped fitness center, and an entertainment room, which is available to rent. Covered, assigned parking. Steps from the water, and all the fine dining and entertainment that Sarasota has to offer. Schedule your showing today!
Listing is courtesy of: FITZ REAL ESTATE SERVICES (813-862-2045)
Listing Agent: Laura-Lee Hubert (631-764-8163)
540 N TAMIAMI TRL #1201, SARASOTA, FL 34236
$3,626,000197 Days on yellowkey MLS ID: A4667550
REDUCED by $373,000 (9.3%) on 04/13/2026
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3630 Built: 2020 Tax: $53,898 (2024)Community: The Blvd SarasotaCondo
Taxes:$53,898
Remarks: Welcome to BLVD Sarasota, a stunning downtown sanctuary in the sky where luxury living meets extraordinary views from every room. Perched in the desired corner stack of the building, this exclusive residence offers uninterrupted, floor-to-ceiling panoramas of Sarasota Bay and the vibrant city skyline — all from the comfort of each space in the home. Whether you're waking up in the primary suite, preparing a meal in the chef’s kitchen, or hosting guests in the expansive living and dining areas, you're surrounded by natural beauty at every turn. Exit your private elevator into over 5,000 square feet of exquisitely designed indoor-outdoor living. The open floor plan is drenched in natural light from walls of PGT impact-rated glass, ensuring every room becomes a front-row seat to Sarasota’s spectacular sunsets, coastal waters and sparkling city lights. The oversized, wrap-around terrace extends your living experience outdoors, offering multiple seating, lounging and dining areas — all designed to showcase the unrivaled, wrap-around water and city views. Offered turnkey furnished, this residence includes three spacious bedrooms with en-suite baths, a private office and two additional half baths, blending the space and comfort of a single-family home with the ease of elevated condominium living. Interior features include soaring 11-foot ceilings, Lutron-controlled lighting, motorized window shades, premium finishes, and designer-selected furnishings that elevate the elegance throughout. The gourmet kitchen is a showpiece with custom gray Irpinia cabinetry, quartz countertops and top-of-the-line appliances — all positioned to ensure you never miss a moment of the view. Entertain effortlessly with two oversized pantries, dual sinks and generous storage. The primary suite is a retreat, offering breathtaking vistas right from bed, along with dual custom walk-in closets and a spa-inspired bath with a soaking tub, frameless glass shower, and refined Kohler fixtures. BLVD Sarasota is a lifestyle unlike any other, offering residents top-tier amenities such as a rooftop infinity-edge pool, outdoor kitchen, wine cellar, state-of-the-art fitness center, golf simulator and a fifth-floor pet lawn with a grooming station. Enjoy two premium parking spaces, a private elevator entrance and a humidity-controlled storage locker. Just a short distance from the 53-acre Bay Park and Sarasota’s world-class dining, arts and marina scene, this is more than a home — it’s your front-row seat to the best of the Gulf Coast. Residence 1201 is not just a place to live — it’s a window to the world, where every room frames an unforgettable view.
Listing Agent: Katy Mcbrayer (941-400-2406)
1330 MAIN ST #3, SARASOTA, FL 34236
$3,845,000208 Days on yellowkey MLS ID: A4665421
REDUCED by $150,000 (3.8%) on 04/13/2026
Bed: 3 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 3954 Built: 1926 Tax: $32,958 (2025)Community: Orange Blossom TowerSpa: NoCondo
Taxes:$32,958
Remarks: Experience elevated downtown living in this exquisite residence at 1330 Main Street, Unit 3, ideally positioned in the vibrant heart of Sarasota. Blending timeless sophistication with effortless convenience, this exceptional property is located within Orange Blossom Tower—one of downtown’s most iconic and historically significant buildings—offering a rare opportunity to own a piece of the city’s rich architectural legacy. Importantly, the building’s Structural Integrity Reserve Study (SIRS) and Financial Reserve Study (FRS) were both completed in 2024, ensuring full compliance with current Florida regulations and giving buyers added peace of mind. Originally constructed in the 1920s during Sarasota’s early boom, Orange Blossom Tower stands as a testament to classic design and enduring charm, seamlessly paired with modern-day luxury. This unique blend of history and refinement sets the tone for a truly distinctive living experience. From the moment you enter the residence, you’re welcomed by an expansive, light-filled interior where thoughtful design and elegant finishes create a sense of understated luxury. The open-concept floor plan is perfectly curated for both intimate living and upscale entertaining, with seamless flow between the living, dining, and kitchen spaces. Generous windows bathe the home in natural light, enhancing the airy ambiance while showcasing the energy and charm of downtown just beyond your doorstep. The residence offers a tranquil retreat above it all—where comfort meets style in every detail. Whether hosting guests or enjoying a quiet evening in, the space is designed to feel both inviting and elevated. Every element has been carefully considered to deliver a low-maintenance, lock-and-leave lifestyle without compromising on sophistication. Step outside and immerse yourself in the very best of Sarasota living. Enjoy morning strolls to local cafés, afternoons exploring art galleries and boutiques, and evenings filled with world-class dining and waterfront sunsets along Sarasota Bay—all just moments away. The location places you at the center of it all, while the historic charm of Orange Blossom Tower provides a sense of character and prestige that is truly unmatched. Perfect as a full-time residence or an elegant seasonal retreat, Unit 3 at 1330 Main Street offers a rare blend of history, luxury, and walkability—delivering an unparalleled downtown Sarasota lifestyle.
Listing Agent: Kim Ogilvie (941-951-6660)
476 MEADOW LARK DR, SARASOTA, FL 34236
$4,495,00010 Days on yellowkey MLS ID: A4689563
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3336 Built: 1985Monthly Fee: $110 Tax: $41,567 (2025)Community: Bird Key SubSpa: NoSingle Family
Taxes:$41,567
Remarks: A Key West-inspired waterfront retreat in prestigious Bird Key, this residence blends timeless coastal design with extensive updates and exceptional indoor-outdoor living. Set along 101 feet of canal frontage with direct access to Sarasota Bay, the property offers a rare opportunity to enjoy a boating lifestyle in one of the area’s most sought-after neighborhoods. Manicured landscaping and inviting front porches introduce the home’s architectural charm, while inside, nearly 3,400 square feet of living space unfolds across two levels (furnishings may be purchased separately). Beautiful hardwood flooring connects the open layout, where vaulted ceilings, skylights, and impact-rated PGT windows and doors fill the interiors with natural light. The double glass and solid wood entry opens to a bright, contemporary living space that flows effortlessly into the formal dining area. At the heart of the home, the eat-in chef’s kitchen is thoughtfully designed with shaker-style cabinetry, quartz countertops, stainless steel appliances, a center island, and a breakfast bar peninsula. A dedicated cafe-style dining area is complemented by a wet bar featuring dual wine cooler/beverage refrigerator, and floating shelving. Impact sliding glass doors open to the covered outdoor entertaining area and pool deck beyond. This inviting space overlooks the family room. Upstairs, the oversized primary suite offers a private retreat with terrace access, a spacious en-suite bathroom, and a walk-in closet. A second en-suite bedroom also enjoys its own terrace, while two additional guest bedrooms share a third bath, providing flexibility for family and visitors. Outdoor living is designed for both relaxation and entertaining. The heated swimming pool is surrounded by a brick paver deck, with an additional open deck ideal for lounging. Just beyond, the extended dock and newly reinforced seawall (2025) create a seamless connection to the water, offering direct access to the waterway that flows out to Sarasota Bay, for boating and waterfront enjoyment. A long list of improvements enhances the home’s value and peace of mind, including a 2023 metal roof, impact PGT windows and doors, updated mechanical systems, and recent exterior upgrades such as new soffit, fascia, and gutters (2026). Bird Key is known for its central location between downtown Sarasota and St. Armands Circle, offering residents convenient access to waterfront dining, boutique shopping, and cultural venues. Just minutes away, Lido Beach and Longboat Key provide some of the region’s most celebrated Gulf-front shorelines, while nearby marinas and yacht clubs complement the boating lifestyle that defines this exceptional community.
Listing Agent: Roger Pettingell (941-387-1840)
750 N TAMIAMI TRL #314, SARASOTA, FL 34236
$439,900106 Days on yellowkey MLS ID: A4676869
Bed: 2 Bath: 1.0 Gar: 2 Liv Area Sq Ft: 1085 Built: 2001Monthly Fee: $1,117 Tax: $5,186 (2025)Community: Renaissance 1Spa: YesCondo
Taxes:$5,186
Remarks: Welcome to Renaissance residence 314, a blend of charm and modern luxury in this fully renovated condominium offering over 1,000 square feet of thoughtfully designed living space. This beautifully updated unit features an expansive family and dining room, an oversized primary bedroom, and a versatile den that can easily serve as a second bedroom. Completely renovated in 2024, this home is move-in ready with every detail meticulously updated for your convenience. The sleek kitchen boasts matching GE Profile appliances, an LG washer and dryer, and new cabinetry with built-in storage solutions, offering ample space for all your needs. Freshly repainted in a neutral palette and paired with new luxury vinyl flooring throughout, the space provides a timeless foundation for any design style you choose. The spacious primary bedroom includes custom built-in closets and offers plenty of room to craft your ideal Sarasota retreat, while the remodeled en-suite bath features elegant quartz countertops, new cabinetry and a stunning shower with dual showerheads, exuding style and comfort. Renaissance is more than just a residence, it’s a lifestyle. This 16-story condominium high-rise offers an impressive array of resort-style amenities, including beautifully landscaped plazas and fountains, 24-hour front desk service and keycard secured entry. The building’s proactive maintenance ensures peace of mind, with recent updates including a new roof and cleaned piping systems in 2024. Designed with durability in mind, Renaissance features reinforced concrete beams, fireproof materials, and elevated guest parking and lobby spaces, providing stability and security. Residents enjoy world-class amenities such as a clubroom, business center, fitness center, resident theater and concierge services. For hosting guests, the building offers two fully equipped guest suites available by reservation. This unit comes with two assigned parking spaces conveniently on the third floor of the secured garage, ensuring your vehicles are protected and elevated over 50 feet above sea level. In the heart of Sarasota’s vibrant cultural district, Renaissance places you near The Bay Park and the city’s dynamic social scene. Designed in the style of an Italian villa, the building's charm is matched by its prime location, where water views are preserved thanks to Renaissance's ownership of aerial rights over the park. Embrace the luxury, convenience and unmatched beauty of living in Renaissance Unit 314. Your Sarasota dream home awaits!
Listing Agent: Moriah Taliaferro (941-504-9910)
631 N ORANGE AVE #208, SARASOTA, FL 34236
$344,900165 Days on yellowkey MLS ID: A4671326
REDUCED by $10,000 (2.8%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 784 Built: 1982 Tax: $2,508 (2024)Community: Mentone CourtSpa: NoCondo
Taxes:$2,508
Remarks: One or more photo(s) has been virtually staged. Unit #208 is one of just five 2BR/2BA homes for sale under $500,000 in the entire SRQ downtown region – it’s the only one under $399,000 and it’s the closest to the downtown center. Located In the charming Mentone Court complex with just 16 residences in the heart of the Rosemary District, the entire complex is above the flood plain and #208 has assigned covered parking. Its HOA fees and taxes may be the lowest in city and the HOA pays for insurance on the building, a huge benefit. With a walkability score of 92 it’s a "Walker's Paradise” and four restaurants with outdoor dining are less than a block away in gorgeous Citrus Square which has its own Veo Public Scooter stand. Walk five-minutes to the Main Street dining scene, or a few blocks to Whole Foods. It’s all about affordable convenient city living. This bright, well laid-out 2nd floor corner unit feels spacious with high ceilings, an open floor plan and large-format porcelain tile, and five closets. Recessed ceiling lighting shows off a fresh tropical paint color palette, the plantation blinds on all windows and the 12’ slider’s vertical blinds are included. The kitchen’s refinished solid wood cabinetry complements granite countertops while under-cabinet lighting illuminates a striking pearlescent subway tile backsplash. The induction range, dishwasher and refrigerator are new (never used). Also new is the efficient HVAC system and four Hunter remote-control ceiling fans. Two updated baths feature a pristine cast iron tub in one and an oversized shower with classic white subway tile in the other. A stacked washer/dryer is included. The large primary bedroom can fit a king bed and has a California-style walk-in closet. The 12’ glass slider opens to an oversize screened-in lanai protected by a motorized 12’ roll-down Kevlar storm/sunshade rated for a Cat. 5 hurricane. This top-quality screen has a battery backup and its MagnaTrack keeps it taut – no sagging, ever. A remote control lets it double as a sunscreen to use the patio throughout the Summer. Master insurance on the structure, water, sewer, trash, reserve funding, landscaping and exterior maintenance are all included in the low $522 monthly HOA fee. The HOA is professionally managed and fully funded; no special assessments are planned. Minimum one-week rentals and small pets are allowed. Mentone Court is not in a flood zone has never had storm damage – block construction with a newer tile roof means it’s inexpensive to insure appliances and contents as the building is insured by the HOA for peace of mind. Under three stories it’s exempt from Milestone inspections, rules and high mandated reserves. The Legacy Trail starts in Payne Park, a one mile bike ride away. Longboat Key is a short drive or just grab the nearby free Bay Runner trolley that runs daily every twenty minutes 7am–11pm to St. Armands Circle, then to Lido Beach Park with its huge pool and amenities then on to unspoiled South Lido Beach with its nature walks, see the photos. It’s the same pristine white sand as Siesta Key 1000 feet to the south, but without the crowds, traffic and parking hassles. Unit #208 checks off every box for worry-free affordable downtown living with easy beach access. With its own covered parking spot and only 12-minutes by Uber to the airport, Unit #208 could be your seasonal 2nd home, investment property that pays for itself, or live full-time downtown and walk everywhere.
631 N ORANGE AVE #107, SARASOTA, FL 34236
$389,900273 Days on yellowkey MLS ID: A4659021
REDUCED by $10,000 (2.5%) on 04/13/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 784 Built: 1982 Tax: $2,713 (2024)Community: Mentone CourtCondo
Taxes:$2,713
Remarks: This beautifully renovated first-floor unit is one of just five 2BR/2BA homes for sale under $500,000 in the SRQ downtown region – and it’s the closest to the downtown center with a five-minute walk to the Main Street dining scene and shops, or a few blocks to Whole Foods. Located in the charming Mentone Court complex with just 16 residences in the heart of the Rosemary District, the entire complex is above the flood plain and #107 has assigned covered parking just 50 feet away. Its HOA fees and taxes may be the lowest in city and the HOA pays for insurance on the building. With a walkability score of 92 it’s a "Walker's Paradise” and four restaurants with outdoor dining are less than a block away in gorgeous Citrus Square which has its own Veo Public Scooter stand. The oversize lanai leads directly to private green space, then to a locking gate in the garden wall and on to four restaurants in Citrus Square just 400 feet away. Main Street’s cafes & shops are a five-minute walk, while Whole Foods is a few blocks away. #107 comes furnished with a 75" Frame TV, all the artwork and most of the furniture pictured. Gut-renovated and unoccupied since (new plumbing, paint, AC/heat, ceiling fans). The unit feels spacious with high ceilings, porcelain tile flooring, 5" baseboards, plantation blinds and four closets. The guest shower is oversized, and the primary bath has a 3/8” frameless glass shower door; both have high-end Kohler Awaken fixtures, Choreograph shower barres and gorgeous designer tile. The new LG heat pump washer/dryer is ready for your beach towels. The kitchen features new Samsung smart Wi-Fi appliances with an induction range and quiet dishwasher. Quartz countertops complement solid hickory dovetailed cabinets that will never delaminate. The backsplash and island are clad with chic hand-made Moroccan Zellige tile by Cle. The oversized 5'x13' lanai (with storage closet) is protected by a 12' motorized roll-down Kevlar storm/sunshade rated for a Cat. 5 hurricane; its MagnaTrack system keeps the screen taut – no sagging, ever. It doubles as a sunscreen so you can use the patio year-round. Master insurance on the structure, water, sewer, trash, reserve funding, landscaping and exterior maintenance are all included in the low $522 monthly HOA fee. All you pay is cable and electricity. The HOA is professionally managed and fully funded; no special assessments are planned. Minimum one-week rentals and small pets are allowed. Community is not in a flood zone has never had storm damage – block construction with a newer tile roof means it’s inexpensive to insure the contents. Under three stories it’s exempt from Milestone inspections, rules and high mandated reserves. The Legacy Trail starts in Payne Park, a one mile bike ride away. Longboat Key is a short drive or just grab the nearby free Bay Runner trolley that runs daily every twenty minutes 7am–11pm to St. Armands Circle, then to Lido Beach Park with its huge pool and amenities then on to unspoiled South Lido Beach with its nature walks, see the photos. Unit #107 checks off every box for worry-free elegant, but affordable, downtown living with easy beach access. With its own covered parking and only 12-minutes by Uber to the airport Unit #107 could be your elegant city pied-a-terre, investment property, or live full-time downtown and walk everywhere.
1022 S OSPREY AVE, SARASOTA, FL 34236
$1,599,000203 Days on yellowkey MLS ID: A4666624
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 2284 Built: 1922 Tax: $4,185 (2024)Community: Rigbys SubSingle Family
Taxes:$4,185
Remarks: Situated in the highly desirable West of Trail neighborhood of Hudson Bayou, this fully restored 1922 residence is the perfect blend of historic charm and modern conveniences. The property offers 2,284 square feet with two bedrooms and two bathrooms in the main house, plus a one-bedroom, one-bathroom guest house. Renovations include a 2006 conversion of the garage into a guest house with a stucco privacy wall and Chicago brick driveway. In 2018, a spacious primary suite with double closets, a large bath, and French doors to a screened lanai was added. High ceilings, oversized impact windows, and refinished hardwood floors (2024) add to the home’s appeal. Recent updates include a recoated roof with a 10-year transferable warranty (2025), A/C (2023), water heater (2024), encapsulated crawlspace with dehumidifier (2024), foundation reinforcement with new support jacks (2024/2025), and hurricane-rated windows. The kitchen and dining area were fully renovated, featuring custom Conestoga cabinetry and designer appliances (2024/2025). Additional features include recessed lighting, custom closets, a Murphy bed, and a natural gas fireplace. A wellness room with an infrared sauna (2025) completes the interior. Exterior highlights include enhanced landscaping, three all-weather sheds, a pergola with natural gas grill hookups, and a serene brick courtyard surrounded by mature landscaping for privacy. The location is unparalleled, with proximity to Southside Village, the downtown Sarasota bayfront, St. Armands Circle, and the world-famous beaches of Lido and Siesta Key.
Listing Agent: Barbara May (404-822-9264)
33 S PALM AVE #1601, SARASOTA, FL 34236
$3,950,000278 Days on yellowkey MLS ID: A4659041
2 Days Off yellowkey (back on 4/13/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3407 Built: 2024Community: DemarcayCondo
Remarks: Under contract-accepting backup offers. Penthouse Collection residence on the 16th floor of the newly built DeMarcay, capturing commanding vistas over downtown Sarasota, Sarasota Bay, Big Pass and the Gulf. Perfectly positioned at the corner of Main Street and Palm Avenue, this address places art galleries, acclaimed dining, boutiques, theaters, the farmers’ market, the city marina, wellness studios and live music within an easy stroll. Plus, St. Armands Circle and Lido Beach are just three miles across the Ringling Bridge. DeMarcay sets a new benchmark for downtown living with elevated, resort-inspired amenities crowned by an 18th-floor bi-level terrace with 360-degree views. Residents enjoy a state-of-the-art fitness center, club lounge, outdoor kitchen, and a spectacular pool terrace designed for sunset lounging and entertaining, supported by dedicated on-site staff available 24/7 for personalized service. This is the only condominium in downtown Sarasota with 24/7 valet parking service, offering a distinctive, space-saving parking configuration and the ease of round-the-clock attended vehicle access. Bayside on the 16th floor, this elegant 3,407-square-foot residence offers three private bedroom suites, a separate office/den, powder room, open-concept living, laundry facilities, and a private bayfront balcony. Volume ceilings and expansive glass invite natural light and frame the skyline and water views throughout. The gourmet kitchen features imported Italian cabinetry, quartz countertops, a Miele five-burner gas cooktop, and integrated Miele appliances. The primary suite is a true retreat with a spa-inspired bath showcasing designer Italian cabinetry, porcelain undermount sinks, a soaking tub and a spacious walk-in shower. An 18-story boutique condominium of only 39 residences, DeMarcay uniquely weaves modern architecture with Sarasota history, thoughtfully preserving and restoring the iconic facades of the original DeMarcay Hotel (1922) and the Roth Cigar Factory (1923–1938). A rare opportunity to live above it all: At the city’s most walkable crossroads surrounded by water, culture and coastal ease.
Listing Agent: Andrew Tanner (941-539-0998)
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