Location: Sarasota
Keyword(s): Booker Middle
Keyword(s) Middle School: Booker Middle
Do Not Show Listings
435 S GULFSTREAM AVE #403, SARASOTA, FL 34236
$649,500245 Days on yellowkey MLS ID: A4667640
REDUCED by $500 (0.1%) on 05/21/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1424 Built: 1972Monthly Fee: $1,393 Tax: $8,165 (2024)Community: Regency HouseCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$8,165
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Booker Middle
Remarks: Wake up to Sarasota Bay. Walk to everything else. This is the one you've been waiting for — a fully renovated 2-bedroom, 2-bath residence at The Regency House, where downtown Sarasota's most coveted address meets the shimmering waters of Sarasota Bay. Unit #403 has been thoughtfully reimagined from the inside out, featuring a stunning new kitchen, beautifully appointed bathrooms, and fresh flooring throughout — move-in ready and magazine-worthy. The Regency House is having its moment. A brand-new community pool has been approved, and the seller is covering the assessment in full — so you inherit all the upside with none of the hassle. Step outside and you're already living your best life. Bayfront Park, the vibrant energy of Main Street, world-class dining, arts, and the Saturday Farmers Market — all of it is right here, on foot. This isn't just a home. It's a front-row seat to everything that makes Sarasota one of the most sought-after cities in Florida. For the buyer who refuses to compromise — on location, on lifestyle, or on quality — 435 S Gulfstream Ave #403 is the answer. Schedule your private showing today. Opportunities like this don't wait.
Listing is courtesy of: MEDWAY REALTY (941-375-2456)
Listing Agent: Kim Donahue (941-724-2587)
1040 VILLAGIO CIR #201, SARASOTA, FL 34237
$220,000121 Days on yellowkey MLS ID: A4680583
REDUCED by $10,000 (4.3%) on 05/03/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 2002 Tax: $3,051 (2025)Community: VillagioCondo
Taxes:$3,051
Elementary School: Tuttle Elementary
High School: Booker High
Tax Year: 2025
Remarks: Located in the popular Villagio community, this two-bedroom, two-bath second-floor corner condominium offers a functional split floor plan. The unit has been freshly painted in neutral tones and features brand-new carpet throughout. The kitchen includes all-wood cabinetry, a breakfast bar, pantry, and a built-in desk. Both bathrooms have been updated with brand-new shaker-style vanities and granite countertops. The primary bedroom includes an en-suite bathroom and a walk-in closet. An additional office or den provides flexible space for remote work or everyday use. This light and bright second-floor unit features tray ceilings in the main living area and no neighbors above! A covered balcony offers west-facing exposure with sunset views. The unit also includes a covered carport – not all do! Villagio offers maintenance-free, resort-style living with amenities that include a heated pool, clubhouse, fitness center, tennis court, putting green, picnic area, dog park, and playground, all with a low HOA fee. Centrally located with convenient access to Ed Smith Stadium, Mote Marine, and downtown Sarasota shopping, dining, waterfront, and beaches. Suitable as an investment property, seasonal residence, or starter home.
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Rachel Harvey (941-726-9300)
4391 WOODMANS CHART #155, SARASOTA, FL 34235
$349,00023 Days on yellowkey MLS ID: A4694064
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1535 Built: 1977 Tax: $3,452 (2025)Community: Woodmans ChartVilla
Taxes:$3,452
Elementary School: Gocio Elementary
Remarks: Nestled in the highly sought after community of Woodmans Chart, this 2 bedroom/2 bath villa combines architectural character, abundant natural light, and a resort style lifestyle just 15 minutes from downtown Sarasota and about 30 minutes from world-renown Siesta Key Beach. Soaring vaulted ceilings with striking wood beams create warmth and charm throughout most of the home, while recent interior paint and new plank-style tile flooring add a fresh, modern touch. The spacious living area also has a sun room adjoining it with a large skylight that basks the area in light, and creates a bright and welcoming gathering space. A spacious primary suite features a row of French doors that open to the main living area, enhancing the home's airy, open feeling. What was most likely once an open atrium has been thoughtfully enclosed to create a stunning sunroom featuring three skylights set into the vaulted ceiling. Bathed in natural light and surrounded by two walls of French doors, this inviting space would make an exceptional art studio, reading room, or extra sleeping area for guests. The entire rear of the home is designed to bring the outdoors in, with walls of glass featuring dual four-paneled sliding glass doors and a large picture window overlooking the expansive 35-foot screened lanai-perfect for entertaining, relaxing, or enjoying peaceful garden views. Just off the dining room, a door leads to a private outdoor patio finished with charming brick pavers-an ideal setting for relaxing outdoors in complete privacy, enjoying morning coffee, or soaking up the Florida sunshine. From the patio, you have direct access to the spacious two-car garage, offering both convenience and ample storage. Residents of Woodmans Chart enjoy access to two community pools as well as a private tennis court tucked away among mature trees and lush landscaping, adding to the peaceful, resort-style that makes The Meadows such a sought-after community. The 1600 acres of The Meadows offers 14 miles of scenic trails and optional memberships to a fitness center, tennis and pickleball courts, a Junior Olympic pool, and golf. Everyday conveniences are close at hand, with easy access to premium shopping, dining, and entertainment including The Fresh Market, Whole Foods, UTC Mall, the new Mote Marine Laboratory & Aquarium, and the popular Waterside district in Lakewood Ranch. This central location places the very best of the Sarasota lifestyle right at your doorstep. There is a One Time $1000.00 Capital Improvement fee at Closing.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Stacy Liljeberg (941-544-6103)
4668 OAK HILL LN #40, SARASOTA, FL 34232
$280,000105 Days on yellowkey MLS ID: A4683176
REDUCED by $10,000 (3.4%) on 05/06/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1024 Built: 1985Monthly Fee: $559 Tax: $3,287 (2025)Community: Village Oaks Sec ASpa: NoVilla
Taxes:$3,287
Remarks: Your Private Sarasota Sanctuary Awaits! Discover true Florida living in this beautiful end unit villa situated on a quiet street. This 2 BR/2BA gem located in the Village Oaks Community is a breath of fresh air. Enjoy morning coffee on your screened front porch or sunsets drinks on the large rear lanai. Inside, the home features vaulted ceilings in living/dining areas and luxury vinyl plank flooring flowing throughout the main living space and bedrooms. The split-bedroom floor plan ensures maximum privacy for owners and visitors alike. The bright kitchen features stainless appliances and an eat-in nook filled with natural light. Best of all, the community pool and tennis court are just steps away from your front door! Perfectly located near UTC shopping and beautiful beaches nearby - this is the Florida lifestyle you've been searching for!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Laura Flood (941-725-2500)
365 OAK HILL WAY #32, SARASOTA, FL 34232
$280,000146 Days on yellowkey MLS ID: A4677958
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1174 Built: 1985Monthly Fee: $559 Tax: $570 (2025)Community: Village Oaks Sec BSpa: NoVilla
Taxes:$570
Remarks: One or more photo(s) has been virtually staged. Nestled in the quiet, pet friendly community of Village Oaks features this Immaculate updated 2-bedroom, 2 bathroom Condo/Villa that offers a move-in-ready retreat. This fully updated unit features a new hot water heater installed in January 2026 and boasts a freshly repainted interior throughout. The modernized kitchen offers a pass-through to the dining area. Updated Master Bath with dual sinks, and walk in shower. Enjoy the look of luxury vinyl that flows seamlessly through every room. The open-concept living room boasts of high ceilings, while an enclosed Florida room (lanai) provides a private space to enjoy the lush surroundings. The villa features a convenient in unit laundry area with a washer and dryer tucked into a dedicated laundry closet.Enjoy the convenience of a private one car garage with remote access, plus two dedicated exterior parking spots right outside your villa. Community pool overlooking lake along with tennis/pickleball court for outdoor activities. Ideally situated between I-75 and downtown Sarasota, offering quick access to the University Town Center Mall (UTC), local dining and world-class beaches.
4481 ASCOT CIR N, SARASOTA, FL 34235
$285,000295 Days on yellowkey MLS ID: A4662740
REDUCED by $13,000 (4.4%) on 05/27/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1376 Built: 1994Monthly Fee: $894 Tax: $3,753 (2025)Community: Longwood VillasVilla
Taxes:$3,753
Elementary School: Emma E. Booker Elementary
Remarks: Welcome to Tivoli Village—an exclusive, private community of just 100 residences nestled among mature trees and lush landscaping. This beautifully maintained 2-bedroom, 2-bath villa with a den/office and 2-car garage offers the perfect blend of tranquility and convenience. Step inside this home peacefully knowing the major concerns have been upgraded a NEWER ROOF, A/C 2023, WATER HEATER 2023, EXTERIOR PAINT IN 2023 AND NEW BACKFLOW METER IN 2026. Seller is offering a $3000 CREDIT for HOA fees! Ideally located near UTC shopping and dining, I-75, Nathan Benderson Park, Sarasota-Bradenton International Airport (SRQ), and just a short drive to downtown Sarasota and Gulf Coast beaches. Step inside to an open-concept floor plan featuring soaring cathedral ceilings, abundant natural light, and seamless flow between the kitchen, dining, and living areas—perfect for both everyday living and entertaining. The updated kitchen showcases newer stainless steel appliances, ample cabinetry with slide-out shelving, a breakfast nook, and an extended breakfast bar overlooking the main living space. Sliding glass doors lead to an enclosed lanai, with additional paver patio space extending into a private, tropical outdoor retreat complete with native Florida landscaping and a custom tiled table and seating area. The spacious primary suite is privately situated at the rear of the home and features an updated en-suite bath with dual vanities, granite countertops, and a walk-in shower with built-in bench. A split-bedroom layout ensures privacy for guests, with a secondary bedroom and full bath located at the front of the villa. The versatile den/office includes a skylight and closet, making it ideal for a home office or potential third bedroom. Tivoli Village residents enjoy a scenic setting with four spring-fed lakes, fishing opportunities, majestic oak trees, and a tranquil nature trail. The HOA provides exceptional value, covering major expenses such as property insurance, exterior maintenance (including power washing and painting), roof replacement and repairs, as well as lawn care and irrigation—delivering low-maintenance, worry-free living. Don’t miss this opportunity to own a move-in-ready villa in one of Sarasota’s most charming and conveniently located communities!
Listing is courtesy of: EXP REALTY LLC (888-883-8509)
Listing Agent: Diane Goodwin (941-706-6620)
401 QUAY COMMONS #1501, SARASOTA, FL 34236
$7,250,000145 Days on yellowkey MLS ID: A4678497
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3798 Built: 2021 Tax: $70,210 (2025)Community: Ritz Carlton ResidencesCondo
Taxes:$70,210
Elementary School: Alta Vista Elementary
Remarks: This fully bespoke designer corner residence at the Ritz-Carlton Residences Sarasota offers enduring, world-class luxury for buyers accustomed to the best. A clean, modern interior hand-finished by local artisans, panoramic bay-to-Gulf views, fully integrated home automation and legendary Ritz service sets the highest standard for an urban resort lifestyle. In downtown Sarasota’s flourishing Quay District, life here is centered on ease and access. It’s an easy distance to The Bay, Bayfront Park and Marina Jack. Downtown restaurants, boutiques, galleries, groceries, cinemas and farmers market are within a mile, while SRQ International Airport, Sarasota Memorial Hospital, St. Armands Circle and Lido Beach are all within three miles. A flow-through layout is framed by floor-to-ceiling glass and luminous vistas. Wake up each day to this amazing view when the shades automatically go up at the appointed time. Three balconies extend the sunny disposition, highlighted by a 31-by-12-foot main terrace with a built-in electric grill. Distinctive details include a built-in lounge bench with automated pop-up table, an elegant wet bar with leather-clad cabinetry, custom textured metal accent walls, Aku wood-slat acoustic panels and genuine crushed-pearl textured paint. A standout feature of this three-bedroom, three-and-a-half-bath residence is the expansive primary bath. Wrapped in marble stone, it features dual vanities, a micro-jetted soaking tub and a double shower with ceiling rain showers, adjustable sprays and in-wall body sprays. Dual walk-in closets are equally considered, with integrated lighting and custom wardrobe organizers designed to keep everything neatly within reach. Amenities reflect the Ritz-Carlton gold standard of care, led by 24-hour dedicated staff and concierge service, along with room service from Jack Dusty's. On-site property management, waterfront pool, lap pool, fitness room, game room and gathering spaces complete the lifestyle. This is The Ritz-Carlton at its most personal, bespoke, beautifully finished and fully integrated, with clear bay-to-Gulf views and three-balcony outdoor living. For buyers accustomed to the best, it’s a rare chance to claim a signature residence in downtown Sarasota’s Quay District.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Andrew Tanner (941-539-0998)
2702 HIDDEN LAKE DR S #A, SARASOTA, FL 34237
$189,0003 Days on yellowkey MLS ID: C7527047
Bed: 3 Bath: 2.0 Liv Area Sq Ft: 1189 Built: 1974 Tax: $2,214 (2025)Community: Hidden Lake VillageCondo
Taxes:$2,214
Remarks: Spacious 3-bedroom, 2-bath first-floor end-unit condo in Hidden Lake Village! Featuring nearly 1,200 sq. ft. of living space, ceramic tile flooring, walk-in closets, ceiling fans, and a screened patio. Enjoy resort-style amenities including 2 community pools, fitness center, clubhouse, sauna, tennis courts, billiards room, picnic areas, and playgrounds. Conveniently located near Downtown Sarasota, Ed Smith Stadium, Lido Beach, St. Armands Circle, shopping, dining, and public transportation. A fantastic opportunity to own in one of Sarasota's most convenient locations!
Listing is courtesy of: MARINA PARK REALTY LLC (941-205-0888)
Listing Agent: Chun-Yi Bittner (941-380-0422)
401 QUAY #1004, SARASOTA, FL 34236
$4,900,0001 Day on yellowkey MLS ID: A4696417
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2984 Built: 2021 Tax: $50,751 (2025)Community: Block 6 CondoSpa: YesCondo
Taxes:$50,751
Remarks: Seldomly available impeccable condominium residence in Sarasota’s most desirable building, The Ritz Carlton Residences, Sarasota. Offering all the quality and impeccable 24-hour service that the Ritz name evokes, along with great public spaces/amenities (two pools, gym, morning room, etc.) and gated private access to The Ritz Carlton Hotel and services. This 10th-floor residence seamlessly combines a sleek modern aesthetic with a comfortable design conducive to relaxed living or stylish entertaining. Enjoy direct water views from inside or while relaxing on the large, covered terrace with a grill. Recharge in the spa-like primary bath, prepare your favorite recipes in the chef's kitchen or settle down in the light-filled great room with a good book. Two en-suite guest suites make it easy to accommodate family or friends. Conveniently moments from most of Sarasota’s many cultural venues, fine restaurants, beaches, museums, galleries and airport. An exciting opportunity for the discerning.
Listing Agent: Steve Wexler (941-586-1124)
1064 N TAMIAMI TRL #1425, SARASOTA, FL 34236
$535,00077 Days on yellowkey MLS ID: A4687230
3 Days Off yellowkey (back on 4/30/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1352 Built: 2007 Tax: $5,881 (2025)Community: Broadway PromenadeCondo
Taxes:$5,881
High School: Riverview High
Remarks: Discover the ultimate blend of upscale downtown living and exceptional affordability at Broadway Promenade! This spacious 3-bedroom, 2-bath residence features a separate dining area one of the largest floor plans available. With natural tones throughout, it creates a warm & inviting atmosphere. Prepare to be captivated by arguably the best views in the building, facing north & overlooking Pioneer Park with peek-a-boo vistas of the Intracoastal Waterway. Enjoy the convenience of two designated parking spaces in the secure under-building garage. Abundant amenities include 24-hour concierge, library, billiards room, fitness center, saunas, heated pool & spa, and outdoor dining areas, all at the most competitive condo fees in downtown Sarasota. Guest suites, pets welcome too! Conveniently located next to Publix Plaza, near chic Rosemary District, with trendy cafes, restaurants, yoga studios, & shopping options. Plus, just moments away from downtown Sarasota, St. Armands Circle, and Lido Beach. Just a stones throw away is The Bay, a breathtaking 53-acre city-owned park featuring exciting amenities including a new performing arts center, public boat launch, array of dining experiences, & scenic green spaces including a restored Mangrove Bayou & Fountain Garden. Experience the luxury of Broadway Promenade where upscale living meets incredible value. Make it yours today!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Nancie Kalin (941-928-8833)
640 N OSPREY AVE, SARASOTA, FL 34236
$1,295,000206 Days on yellowkey MLS ID: A4672346
Bed: 3 Bath: 3.0 Liv Area Sq Ft: 1738 Built: 2005 Tax: $7,718 (2025)Community: Gillespie Park SubSpa: NoSingle Family
Taxes:$7,718
Remarks: Welcome to this unique custom offering of blended versatility, which includes 3 bedrooms with 3 baths. A concrete block custom build in 2005. Directly across the road from Gillespie Park, a dazzling 10-acre monitored park. Ideal for extended family, visitors, artist studio, and/or additional rental income, so just let your imagination run wild. High-impact hurricane windows and a newly installed roof in 2024 with hurricane tie-downs. The freshly painted main house features a double sided gas fireplace, stained acid-washed floors, a common feature throughout the compound, newly installed granite-honed countertops, new subway tiles in the kitchen and freshly painted solid wood cabinets. If it is purity you want, try the Apec Reverse Osmosis dispenser at the newly installed kitchen sink. Bosch gas cooktop, dishwasher and convection wall oven, Whirlpool refrigerator with Electrolux washer and dryer. Tankless on-demand hot water, gas for the main house, and an additional electric unit for the guest suites. A well for irrigation, EV 220-volt 50-amp charging station, storage bins and racks for kayaks, two driveways, private hedging with magnolia, holly, black bamboo and hibiscus, or if it's the fruit you want, mango, avocado, lemon, papaya and banana trees. An outdoor shower, brick pavers throughout the inspiring courtyard with hanging lights, and a fire pit to capture those spectacular starry evenings. One guest suite was built with the original house with a kitchenette, while the second was built in 2022, complete with a full kitchen and washer/dryer combo. Both suites come complete with mini-split heat pumps, one installed in 2023, and are turnkey furnished. Gillespie Park, which is directly across the street, features grand oaks, recreational trails, a lake, tennis courts, a pickleball court, a gazebo, a dog park and a basketball court. Centrally located and within short distance of Sprouts, Whole Foods, restaurants and local shopping, this neighborhood offers a vibrant and ever-evolving downtown neighborhood.
Listing Agent: Dennis Girard (941-809-0041)
800 N TAMIAMI TRL #312, SARASOTA, FL 34236
$690,000121 Days on yellowkey MLS ID: A4682076
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1323 Built: 2007 Tax: $7,012 (2025)Community: AlinariSpa: NoCondo
Taxes:$7,012
Remarks: All the luxury of new construction in this fully remodeled and fully furnished residence in Alinari featuring high-end finishes without the new-build price. It’s the best value in downtown Sarasota. Located in the Rosemary District, you’re moments from downtown’s premier dining, shopping and cultural attractions. Cross the street to the Quay and The Bay waterfront park or take a quick drive over the Ringling Bridge to St. Armands Circle and the powder-soft sands of Lido Beach. Urban energy and coastal tranquility, all within reach. The split two-bedroom, two-bath residence offers 1,323 square feet of open living space appointed with today’s most sought-after finishes, including luxury vinyl plank flooring in white oak, solid-wood cabinetry, quartz countertops, LED lighting with dimmers, premium fixtures and hardware, Lutron automated window shades and stone accent walls in the foyer and dining room. The great room opens to a private balcony overlooking Alinari’s expansive green space. The kitchen features soft-close solid-wood shaker cabinets with designer brass hardware, Cambria quartz countertops, an Elysium glass backsplash and under-cabinet lighting. The primary suite offers a generous walk-in closet, a dedicated coffee bar and an en-suite bath with a dual-sink vanity, honed marble tile and a frameless glass walk-in shower. Alinari is a well-run association with an active social community. Resort-style amenities include concierge service, a heated pool and spa with a sun deck, a private park, a fitness center, a sauna, a theater room, a social room, a billiards room, a business center, indoor bicycle storage and guest suites for visiting family and friends. Wine enthusiasts will appreciate the climate-controlled wine room with personal storage lockers. See it, love it and nothing to do but move right in.
Listing Agent: Peter Laughlin (941-356-8428)
5515 ASHTON WAY #5515, SARASOTA, FL 34231
$250,000105 Days on yellowkey MLS ID: A4683535
REDUCED by $25,000 (9.1%) on 05/29/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1232 Built: 1993Monthly Fee: $315 Tax: $2,155 (2025)Community: Ashton Lakes 08Condo
Taxes:$2,155
Elementary School: Gulf Gate Elementary
Remarks: Price Improvement!! Motivated sellers!! Bring Offers!! Location! Location! Location! Only 3.5 miles to the world-famous Siesta Key Beach. Experience the unique fine quartz sand from the Appalachian Mountains. Close to I-75, rte. 41, shopping, schools, hospitals and restaurants. This 2-bedroom 2 bath walk-up unit has high ceiling, attic space, bright and airy. Unfurnished. Assigned new carport and screened lanai with lake view. Relax on the lanai watching our flora & fauna. Ashton Lakes Community is located on 33 acres of luscious greenery, with 4 lakes, a combination of 2 tennis courts & 4 pickleball courts,2 heated pools, one large with lap lane, shuffleboard, clubhouse, grilling stations, and other amenities. Our complex is connected by a foot bridge to Merchants Mart shopping center. Shops include CVS, ace hardware, liquor, Dollar store and the famous Detwiller's farm market for your shopping convenience. Come, make this slice of heaven your paradise in the sun. Roof 2020. See attachments for disclosures and updates. Welcome to Ashton Lakes...a well-kept secret location!!
Listing is courtesy of: ASHTON LAKES REALTY INC (941-924-4832)
Listing Agent: Philip Abraham (941-441-6958)
1350 5TH ST #402, SARASOTA, FL 34236
$695,00023 Days on yellowkey MLS ID: A4691938
Bed: 1 Bath: 1.0 Gar: 1 Liv Area Sq Ft: 784 Built: 2019Monthly Fee: $724 Tax: $5,936 (2025)Community: Risdon On 5ThSpa: NoCondo
Taxes:$5,936
Remarks: Stunning one bedroom penthouse in the heart of the Rosemary District, one of downtown Sarasota’s most vibrant and sought after neighborhoods, featuring an exclusive private garage, an exceptionally rare offering in luxury condo living. Positioned on a private penthouse level with only four residences, this sophisticated urban retreat combines privacy, security, contemporary design, and unmatched walkability. Filled with natural light, the residence features soaring ceilings, impact rated windows and doors, electric blinds, and refined modern finishes throughout. The open concept layout is complemented by a beautifully appointed kitchen with a premium appliance package, sleek cabinetry, and an oversized single cell sink designed for both style and functionality. Designed by Halflants + Pichette Studio for Modern Architecture, Risdon on 5th showcases striking contemporary architecture and an elevated downtown Sarasota lifestyle. Step outside your door to enjoy the rooftop pool and observation lounges, offering resort style amenities and an elevated atmosphere perfect for relaxing or entertaining. The gated community provides peace of mind while placing you in the center of downtown Sarasota’s thriving arts and entertainment scene. Residents enjoy unbeatable walkability to the Sarasota Opera House, theaters, acclaimed dining, rooftop bars, art galleries, boutique shopping, coffee shops, nightlife, and waterfront attractions. The private one car garage is a true rarity for downtown Sarasota penthouse living, adding convenience and long term value rarely found in the Rosemary District. Ideal as a full time residence, seasonal retreat, or investment opportunity, this exceptional penthouse offers the perfect lock and leave lifestyle in one of Sarasota’s most desirable urban locations.
Listing is courtesy of: THE KEYES COMPANY - SARASOTA (941-362-4100)
Listing Agent: Joseph Mcdonald, Llc (941-375-9646)
1306 GRANTHAM DR, SARASOTA, FL 34234
$330,00052 Days on yellowkey MLS ID: N6143979
Bed: 3 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1769 Built: 2020Monthly Fee: $268 Tax: $2,949 (2025)Community: Bradford Manor TwnhmsTownhouse
Taxes:$2,949
Remarks: FREE home warranty included. Located in the gated community of Bradford Manor, this home offers a LOW HOA fee of $268 per month with NO CDD FEES, covering exterior maintenance, community pool, basic cable, high-speed fiber internet, and trash removal for easy, low maintenance living. Recent enhancements thoughtfully elevate the home, bringing added comfort, efficiency, and peace of mind, including a DuroMax Dual Fuel XP4850EH hook up generator that will be included with the purchase, a water softener system installed in the garage, a UV (UVC) air purification system for the HVAC, a Level 2 EV charging (240V) outlet in the garage, and beautifully upgraded quartz countertops in all bathrooms. Step inside to discover a bright, open concept layout enhanced by high ceilings throughout. The main living areas feature tile flooring and a seamless flow ideal for both everyday living and entertaining. The kitchen is equipped with granite countertops, wood cabinetry, and an oversized breakfast bar that opens to the living and dining spaces. A first floor half bath and two entryway storage closets add convenience, while the screened lanai and paved patio offer a private outdoor retreat with no rear neighbors. The second level offers a well-designed layout with all three bedrooms and a conveniently placed laundry area enhancing everyday functionality. The spacious primary suite features a generous walk in closet and an ensuite bath with dual sinks and a walk in shower. The guest bathroom is designed with functionality in mind, offering a split layout with a dual sink vanity separate from the shower and toilet area, allowing for simultaneous use and enhanced privacy. Additional highlights include a spacious one car garage that not only accommodates a vehicle but also provides valuable extra storage space for tools, beach gear, and seasonal items, hurricane shutters for added protection and peace of mind during storm season, and ample guest parking conveniently located throughout the community, making it easy to host family and friends. Perfectly positioned in a prime Sarasota location, this home is just minutes from downtown, University Parkway, UTC shopping and dining, Sarasota Airport, top rated schools, and the area’s renowned beaches, offering the ideal combination of convenience and lifestyle. This home is perfect for a first time homeowner or as a vacation property, offering low maintenance living, strong lock and leave convenience, and proximity to key amenities, making it easy to enjoy full time living or seasonal escapes with ease. Schedule your private showing today and experience all this home has to offer.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Rick Tritschler, Jr. (941-928-1292)
417 N OSPREY AVE, SARASOTA, FL 34236
$1,795,000239 Days on yellowkey MLS ID: A4667626
REDUCED by $55,000 (3.0%) on 06/10/2026
Bed: 4 Bath: 4.5 Liv Area Sq Ft: 3154 Built: 2025 Tax: $3,873 (2024)Community: Central ParkSingle Family
Taxes:$3,873
Remarks: Experience elevated downtown living in this 2025 NEW CONSTRUCTION home just steps from Main Street. Built on 16-gauge steel framing, this 3,154 sq ft residence sits 23 FEET ABOVE SEA LEVEL and more than 10 feet above the floodplain in coveted ZONE X, a rare combination of elevation and location in downtown Sarasota. The open-concept layout features 10-foot ceilings and a chef’s kitchen with polished marble countertops, 10-foot island, 48” Thor gas range, Miele dishwasher, dual Electrolux refrigerator and freezer, walk-in pantry, reverse osmosis, and whole-home water filtration. The first-floor primary suite opens to a private patio overlooking the HEATED SALTWATER POOL and includes a spa-style bath with freestanding tub, walk-in shower, dual sinks, and dual closets. Upstairs, three en-suite bedrooms provide flexibility for guests or family, including one with a private balcony. The fully fenced backyard is designed for privacy and entertaining, with architectural plans available for a FUTURE GARAGE OR ADU, offering flexibility rarely found in downtown new construction. Additional features include hurricane-rated impact windows, standing seam metal roof, and hard-wired Arlo video entry. Located in Gillespie Park with walkable access to DOWNTOWN SARASOTA, The Bay, Marina Jack, Payne Park, and the beaches of Lido and Siesta Key.
Listing is courtesy of: CATALIST REALTY LLC (386-871-4600)
Listing Agent: Vannesa Poole (407-538-1030)
125 S BLVD OF PRESIDENTS, SARASOTA, FL 34236
$2,999,000129 Days on yellowkey MLS ID: A4680622
REDUCED by $101,000 (3.3%) on 04/15/2026
Bed: 5 Bath: 6.0 Gar: 2 Liv Area Sq Ft: 3043 Built: 1956 Tax: $37,828 (2025)Community: Saint Armands Div John Ringling EstatesSpa: YesSingle Family
Taxes:$37,828
Remarks: Experience luxury island living in this beautifully appointed 5-bedroom, 5.5-bath retreat located just moments from the world-famous St. Armands Circle and Lido Beach. Designed for both relaxation and entertaining, this spacious home offers an exceptional blend of elegant interiors and resort-style outdoor living. The heart of the home is the stunning gourmet kitchen, featuring premium appliances, custom cabinetry, expansive quartz countertops, a gas cooktop, wine refrigeration, and 2 large center islands perfect for gathering with family and friends. The open-concept living area boasts soaring ceilings, abundant natural light, and walls of sliding glass doors that seamlessly connect indoor and outdoor spaces. Step outside to your private tropical oasis, complete with a heated screened pool and spa, covered lanai, comfortable outdoor lounge seating, dining area, and a fully equipped outdoor kitchen and grill station. Whether you're enjoying morning coffee poolside, hosting an evening barbecue, or unwinding after a day at the beach, this home is designed to make every moment memorable. Located near the shops, restaurants, and vibrant atmosphere of St. Armands Circle, and just minutes from the white sand beaches of Lido Key, this exceptional property offers the perfect Sarasota vacation experience.
Listing is courtesy of: PRECISE REALTY CORP (941-400-0374)
Listing Agent: Jennifer Le Blanc (941-400-0374)
1900 BENJAMIN FRANKLIN DR #V12, SARASOTA, FL 34236
$549,900211 Days on yellowkey MLS ID: A4671208
REDUCED by $25,000 (4.3%) on 06/10/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1242 Built: 1967Monthly Fee: $1,217 Tax: $7,227 (2024)Community: Lido HarbourVilla
Taxes:$7,227
Remarks: One or more photo(s) has been virtually staged. Situated on the serene southern tip of Lido Key within the coveted First Lido community, Villa 12 delivers a coastal living experience that is increasingly rare—blending the privacy of a single-family home with the effortless, maintenance-free lifestyle of a ground-level villa. With 2 bedrooms, 2 full baths, and a versatile enclosed Florida room, this residence is ideal for those seeking a quiet island retreat with the vibrant energy of Lido Key just moments away. The villa has been significantly updated from the studs out, providing a fresh and clean interior canvas. The open-concept floor plan features porcelain tile flooring throughout and a modern kitchen appointed with brand-new appliances and sleek finishes—offering a bright, functional space for everyday living and hosting. While the core renovation work has been completed, the home remains a "living canvas," providing a unique opportunity for a new owner to add their own custom refinements and personal style to a high-potential space. Practicality is built-in with rare amenities, including a private attached carport for door-front parking and a dedicated in-unit laundry room. The enclosed Florida room adds valuable square footage, serving as a flexible den, office, or guest space. Just steps from your door, enjoy private beach access and a gulf-front pool where residents gather for sunset views. Positioned just minutes from St. Armand’s Circle and South Lido Park, the location is truly peerless. With a highly motivated seller ready to move, this property is priced to reflect its current condition and presents a significant opportunity for a buyer looking to secure a renovated Lido Key address at a competitive value. Whether you’re looking for a seasonal escape or a high-potential investment, Villa 12 offers a solid foundation in a premier beachside setting.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-907-9595)
Listing Agent: Anthony Rechul (248-930-6638)
1750 BENJAMIN FRANKLIN DR #10G, SARASOTA, FL 34236
$1,175,000129 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)
4018 PRADO DR, SARASOTA, FL 34235
$454,00069 Days on yellowkey MLS ID: A4688500
REDUCED by $5,000 (1.1%) on 06/10/2026
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1842 Built: 1969 Tax: $2,873 (2025)Community: De Soto LakesSingle Family
Taxes:$2,873
Remarks: PRICE IMPROVEMENT! Welcome to this spacious 4-bedroom, 2-bath home featuring an open floor plan that seamlessly connects the kitchen, dining, and living areas—perfect for entertaining or relaxing with family. The large kitchen offers plenty of workspace and storage, while the bonus/family room adds flexibility for a playroom, home office, or media space. The primary suite includes a walk-in shower and an upgraded closet system for extra organization. Throughout the home, you’ll find ceiling fans, ceramic tile and vinyl floors (no carpet), and an inside laundry room. Major updates bring peace of mind: HVAC (2024), water heater (2019), roof (2015), and a new garbage disposal. Step outside to a fully fenced, oversized backyard—ideal for pets, outdoor living, or adding a pool. A large storage shed provides additional space for tools and toys. With no HOA restrictions, you’ll have the freedom to make this property truly your own. Conveniently located near shops, restaurants, the airport, and Sarasota’s world-famous beaches, this move-in-ready home offers comfort, functionality, and a prime location for your Florida lifestyle.
Listing is courtesy of: BETTER HOMES AND GARDENS REAL ESTATE ATCHLEY PROPE (941-556-9100)
Listing Agent: Lynda Ellinger, Pa (941-228-2430)
Please select an email frequency other than None since you have chosen for us to email you with changes that match your search.