Location: Sarasota
Do Not Show Listings
1021 CRESCENT ST, SARASOTA, FL 34242
$1,699,000129 Days on yellowkey MLS ID: A4681826
REDUCED by $46,000 (2.6%) on 05/12/2026
Bed: 3 Bath: 0.0 Gar: 3 Liv Area Sq Ft: 2780 Built: 2015 Tax: $17,389 (2025)Community: Siesta/RocksMulti-Family 5+
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$17,389
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: ***Potential for $150k+ gross income. Zoned for weekly rentals. ONE UNIT IN CONDO COMMUNITY*** Escape to the ultimate Siesta Key lifestyle with this rarely available, coastal contemporary condo—offering the perfect blend of luxury, privacy, and convenience with direct access to the sugar-white sands of world-renowned Siesta Key Beach and Crescent Beach. Known for its quartz-crystal sand and turquoise waters, this top-rated beach offers stunning sunsets, gentle waves, and vibrant coastal charm, all just a short stroll from your door. Nestled in a boutique enclave of only five residences, this exclusive unit has fresh interior paint, lives like a single-family home and is one of only two in its building. This unit encompasses the entire floor and shares no walls with other units. With five private patios, a built-in outdoor grill, tall ceilings and windows, and plantation shutters throughout, the light-filled layout offers an open flow between living, dining, and kitchen spaces—accented by custom cabinetry, upscale finishes throughout. The spacious primary suite provides a private retreat, while the entire home is thoughtfully designed on one level for effortless living. A private elevator offers direct access from your oversized ground-level garage, which is nearly 1,000 square feet and accommodates three vehicles plus storage, along with a private driveway for guest parking — a rare find on the Key. This property is zoned for short-term, weekly rentals and boasts a strong rental history, making it an exceptional opportunity for both personal enjoyment and possibility to earn over $150,000 in investment income. Enjoy walkable access to beachside boutiques, island restaurants, and boat rentals, plus quick and easy access on and off the island, making it ideal for both full-time living and a low-maintenance vacation home. Shared amenities include a serene pool, private owner's clubhouse, and common area used by only five residences, ensuring a peaceful and private setting. Whether you're searching for a serene retreat or a stylish beach escape with income potential, this home offers a unique opportunity to live in the heart of Siesta Key’s coastal paradise. Furnishings optional - not included in list price.
Listing is courtesy of: HARTMAN REAL ESTATE & COMPANY (941-500-4547)
Listing Agent: Zain Hartman (941-735-6415)
659 MALDIVES TRL, SARASOTA, FL 34234
$1,096,498113 Days on yellowkey MLS ID: A4683422
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3227 Built: 2026Monthly Fee: $250 Tax: $4,792 (2025)Community: GracewaterSingle Family
Taxes:$4,792
Elementary School: None
High School: None
Middle School: None
Remarks: Under Construction. Under Construction with anticipated completion date of April 2026. (Pictures current as of 5/12/26) Experience elevated living in the Grand Bay Haven at Gracewater, one of Sarasota’s most exciting new resort-style communities, with a projected completion date of mid-to-late April 2026. This stunning two-story residence offers over 3,200 square feet of thoughtfully designed living space, featuring 4 bedrooms, 3.5 baths, a private study, and an expansive loft/bonus room that provides flexibility for a media space, playroom, or additional guest retreat. Designed for both everyday comfort and effortless entertaining, the open-concept great room flows seamlessly into a chef-inspired kitchen appointed with quartz countertops, natural gas appliances, impact-rated windows and sliders, 8-foot interior doors, and elevated coastal finishes that create a bright, sophisticated ambiance throughout. The spacious primary suite serves as a private sanctuary with a spa-like bath and generous proportions, while three additional bedrooms and two full baths are ideally situated upstairs around the versatile loft area. Step outside to your covered lanai and enjoy your own private inground pool, creating the perfect setting for relaxing afternoons, weekend gatherings, and year-round Florida outdoor living. Located within the gated Gracewater community, residents enjoy a true lifestyle experience with a resort-style zero-entry pool and cabanas, elegant clubhouse, state-of-the-art fitness center, pickleball courts, dedicated dog park, and an on-site lifestyle manager coordinating social events and activities. Just minutes from downtown Sarasota’s dining, arts, and entertainment scene, world-renowned Gulf beaches, SRQ Airport, and convenient access to I-75, this exceptional new construction opportunity blends luxury, comfort, and location—allowing you to secure your place now and move into your brand-new Grand Bay Haven just in time to enjoy spring 2026 in style. (Builder has chosen finishes for the kitchen and bathrooms but different selections can be made if buyer goes under contract prior to installation)
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Richard Tyson (941-999-1179)
4689 PINE HARRIER DR, SARASOTA, FL 34231
$1,599,50042 Days on yellowkey MLS ID: A4692523
1 Days Off yellowkey (back on 5/12/2026)
Bed: 4 Bath: 3.5 Gar: 3 Liv Area Sq Ft: 3103 Built: 1986Monthly Fee: $29 Tax: $7,212 (2025)Community: The LandingsSpa: NoSingle Family
Taxes:$7,212
High School: Riverview High
Remarks: Under contract-accepting backup offers. Multiple Offers. Seller requests highest and best offers by 8pm on May 10. Nestled behind the gates of The Landings, one of the only gated communities "West of the Trail", this custom Florida-style home offers the perfect blend of timeless elegance, spacious living, and an exceptional Sarasota lifestyle. Situated on a desirable corner lot with easy access to the members-only gate, this beautifully updated home spans more than 3,100 square feet and features four bedrooms, three-and-a-half baths, a three-car garage, bonus room, and an upstairs loft area ideal for flexible living. Designed with an open, airy feel and soaring high ceilings, the home is filled with natural light and inviting living spaces perfect for both everyday comfort and entertaining. The expansive screened lanai showcases two separate sitting areas, an outdoor kitchen, a large heated pool with recent resurfacing, and views of the spacious backyard, the benefits of being a corner lot, creating a true private retreat. Inside, the thoughtfully designed floor plan features a rare first-floor primary suite, a highly sought-after feature for a two-story home in The Landings. The updated kitchen is the heart of the home, complete with a large center island perfect for gathering with family and friends while creating lasting memories. Updated bathrooms, a cozy fireplace in the living room, fresh interior and exterior paint, further enhance the move-in-ready appeal of this exceptional property. Residents of The Landings enjoy tree-canopied streets, a private nature trail leading to Roberts Bay, and optional membership to the Landings Racquet Club, featuring tennis, pickle ball, a heated pool, fitness center, and clubhouse. This prestigious gated community of 702 residences borders the Intracoastal Waterway and spans 280 acres with stand-alone homes, villas, and town-homes surrounded by 75 acres of protected mangroves, nature preserves, walking trails, a gazebo, kayak launch, and butterfly garden. Take your golf cart to the Landings Shopping Center which features, Publix grocery store, Starbucks, and numerous dining options from breakfast hot spots to outstanding seafood options. Ideally located near A-rated schools, Southside Village, Sarasota Memorial Hospital, and Sarasota’s renowned dining, arts, and waterfront attractions, this is a rare opportunity to own a beautifully updated home in one of Sarasota’s most desirable gated communities. Located in flood zone X, the highest zone, no flood insurance required.
Listing is courtesy of: PREMIER SOTHEBY'S INTERNATIONAL REALTY (941-364-4000)
Listing Agent: Thomas Hedge, Jr (941-587-6660)
2630 WOODGATE LN #G3, SARASOTA, FL 34231
$189,000266 Days on yellowkey MLS ID: TB8431315
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1100 Built: 1981 Tax: $1,248 (2024)Community: Pinewood Village ViCondo
Taxes:$1,248
Tax Year: 2024
Remarks: $$ 10,000.00 in closing cost's paid for by the SELLER. Like new and upgraded gorgeous condo. Minutes from world famous Siesta Key Beach and safely located in flood zone X. All new vinyl plank flooring in living areas and new carpet in bedrooms. Both bathrooms are newly renovated, freshly painted inside and out, along with a total makeover of the kitchen in 2025. Located in the rear of the development this condo is very quiet and secure. New washer and dryer, make this as good as a new unit. Ceiling fans and skylights keep it light and bright inside. Community heated pool and fitness center are open to the residents at their leisure. Clubhouse includes kitchen, fitness center, pool table and rest rooms with showers. Lanai features fully enclosed glass windows with screens, new storm doors front and rear. Gardener's paradise in the rear with lush tropical plants. In front enjoy your reserved private parking spot. Close to shopping and some of the best restaurants in Sarasota.
Listing is courtesy of: DENNIS REALTY & INV. CORP. (813-949-7444)
Listing Agent: John Pinta (813-390-4918)
1740 ASSISI DR, SARASOTA, FL 34231
$1,370,00065 Days on yellowkey MLS ID: A4689889
Bed: 5 Bath: 4.5 Gar: 2 Liv Area Sq Ft: 3357 Built: 2027Monthly Fee: $320 Tax: $2,045 (2025)Community: Portofino On The BaySpa: YesSingle Family
Taxes:$2,045
Elementary School: Gulf Gate Elementary
Remarks: Pre-Construction. To be built. Located in the highly sought-after Portofino on the Bay neighborhood in Sarasota, this cleared homesite presents a rare opportunity to build your dream home in one of the area’s most desirable coastal communities. The property has already been cleared and is ready for construction, offering a smooth and convenient start for your custom build. A builder of your choice can be selected, however plans have been made for this lot - an option of a 3,357 sq. ft. home, providing the opportunity to streamline the building process with a thoughtfully designed home. Buyers may choose to utilize the existing plans or customize them to suit their vision and lifestyle. Building plans must be approved by the board group of the community. The property is also located within the district for the highly regarded Pine View School, along with other highly rated public and private schools nearby. This private and gated neighborhood is great for boaters, offering community deeded access to the bay and a community day dock, that is available upon reservation. Enjoy direct access to the Intracoastal Waterway. Boat slips could potentially become available for purchase if a community member is selling. Located just 2 miles from downtown Sarasota, residents enjoy quick access to vibrant dining, shopping, and entertainment while still enjoying the privacy and tranquility of this waterfront-friendly community.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
6703 MIDNIGHT PASS RD #101, SARASOTA, FL 34242
$439,90038 Days on yellowkey MLS ID: A4693235
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 964 Built: 1974 Tax: $4,605 (2025)Community: Sea WindsCondo
Taxes:$4,605
Remarks: LOCATION, LOCATION, LOCATION – Live the “beach life” and a wonderful investment opportunity in beautiful Siesta Key, Florida! Enjoy your own piece of paradise at Sea Winds Condominium, Unit 101. This inviting first-floor, turnkey- “fully furnished”condo offers 2 bedrooms, 2 bathrooms, and beautiful views, all within a short walk to the world-famous beaches of Siesta Key. Meticulously decorated and thoughtfully designed, this charming condo features a comfortable living space with easy first-floor access. The unit comfortably sleeps 7 guests. The spacious primary bedroom includes a queen bed, tv, and dedicated workspace, making it ideal for remote work or extended stays. The second bedroom features a trundle bed with an additional matching twin bed, along with its own television. The living room offers additional sleeping accommodations with a queen-size sleeper sofa. The fully-equipped kitchen provides everything needed for everyday living and entertaining, while the dining area seats 6 comfortably. An adjustable coffee table offers seating for two additional guests. The unit includes a designated parking space directly in front of the condo, along with additional guest parking. Cable, water, and sewer are included in the Condo fee. Step outside to your own large, fully fenced private patio oasis featuring a Weber grill, a dining table with umbrella seating for six, and a relaxing conversation area with chairs— perfect for enjoying the Florida sunshine or entertaining guests outdoors. Residents of Sea Winds Condominium enjoy access to a heated community pool with lounge chairs, umbrellas, outdoor shower, and bathrooms for year-round enjoyment. Additional amenities include bicycle storage room, a social room for gatherings, barbeque grill and two shared laundry facilities. For added convenience, the condo also includes beach chairs, beach towels, and a rolling beach storage cart and a large storage unit on the 2nd floor. Beyond the comfort of the condominium, you are only a five-minute walk from the pristine quartz sands of Siesta Key Beach, consistently ranked among the top beaches in the United States. Spend your days soaking up the sun, strolling along the shoreline, or enjoying the spectacular sunsets for which Siesta Key is famous. Leave the light on in the condo, because when you walk back from the beach at night, it feels like a beacon calling you back. Just a short walk away, you’ll find the South Village area featuring restaurants, boutiques, beach bars, ice cream shops, and rental companies offering fishing equipment, boats, kayaks, bicycles, and passenger golf carts. A daily trolley service with stops directly in front of the Sea Winds complex provides convenient access to Siesta Key Village and other island attractions. Being well built all above Sea Level, this inviting two level complex has enjoyed being water free from any storm or hurricane since it was built. Recent community improvements include:• New roof (2024)• Newly renovated swimming pool (2025)• New storm drainage and sewer lines (2025)• Newly paved and striped parking area (2026)Do not miss this incredible opportunity to enjoy coastal living at its finest. This Sea Winds Condominium offers the perfect combination of relaxation, convenience, and adventure in one of Florida’s most sought-after beach destinations. More important though, to truly appreciate this little gem, come and see it for yourself. This unit is precious and deserves to be loved.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Sean Hickey (941-587-4244)
6901 BOCHI CIR, SARASOTA, FL 34242
$2,675,00038 Days on yellowkey MLS ID: A4692713
Bed: 4 Bath: 4.0 Gar: 4 Liv Area Sq Ft: 2729 Built: 2026Monthly Fee: $389 Tax: $4,640 (2025)Community: Coronas ParkSingle Family
Taxes:$4,640
Remarks: Under Construction. Discover La Linda, an exclusive collection of eight custom-built, modern homes offering breathtaking Gulf views just off Ocean Boulevard. Nestled in the highly sought- after Siesta Key, these elevated residences are crafted to the highest standards, featuring solid block construction on all levels, impact-resistant windows and doors, and private elevators for ultimate safety, security, and convenience. Perfectly situated, La Linda is just 5 minutes from Siesta Village and 8 minutes from the world-famous, sugar sands of Siesta Key Beach, providing the ideal balance of privacy and accessibility. Each four- bedroom, fourand-a-half-bathroom home is a masterpiece of refined design, boasting luxury finishes, impeccable craftsmanship, and modern aesthetics throughout. Designed for Comfort, Elegance & Entertainment - First Level: A spacious four-car garage leads to a beautifully designed lanai and pool deck, creating a private outdoor retreat. Second Level: The serene primary suite features a walk-in closet and spa-like bathroom with a freestanding tub, frameless glass shower, and double vanity. Two additional guest bedrooms, and additional living space, balcony access, and a dedicated laundry room complete this level. Third Level: The heart of the home, the open-concept great room, is designed for seamless indooroutdoor living. High ceilings and wraparound balconies maximize the Gulf views, while the chef’s kitchen impresses with a premium Viking appliance package, solid wood cabinetry, and stunning Calacatta Quartz countertops. A guest suite/office adds versatility to the space. Step outside to your own private oasis, where lush landscaping surrounds a sparkling pool and patio area—ideal for relaxation or entertaining. With its prime location, unparalleled craftsmanship, and luxury amenities, La Linda offers an exceptional opportunity to own a modern coastal masterpiece on Siesta Key. Don’t miss your chance to experience the pinnacle of island living—schedule your private tour today!
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Jeremy Hartmark (941-807-0740)
6907 BOCHI CIR, SARASOTA, FL 34242
$2,800,00038 Days on yellowkey MLS ID: A4692735
Bed: 4 Bath: 4.5 Gar: 4 Liv Area Sq Ft: 2970 Built: 2026Monthly Fee: $389 Tax: $4,814 (2025)Community: Coronas ParkSingle Family
Taxes:$4,814
Remarks: Under Construction. Discover La Linda, an exclusive collection of eight custom-built, modern homes offering breathtaking Gulf views just off Ocean Boulevard. Nestled in the highly sought-after Siesta Key, these elevated residences are crafted to the highest standards, featuring solid block construction on all levels, impact-resistant windows and doors, and private elevators for ultimate safety, security, and convenience. Perfectly situated, La Linda is just 5 minutes from Siesta Village and 8 minutes from the world-famous, sugar-white sands of Siesta Key Beach, providing the ideal balance of privacy and accessibility. Each four-bedroom, four- and-a-half-bathroom home is a masterpiece of sophisticated design, boasting luxury finishes, impeccable craftsmanship, and modern aesthetics throughout. Designed for Comfort, Elegance & Entertainment - First Level: A spacious four-car garage leads to a beautifully designed lanai and pool deck, creating a private outdoor retreat. Second Level: The serene primary suite features a walk-in closet and spa-like bathroom with a freestanding tub, frameless glass shower, and double vanity. Two additional guest bedrooms, and additional living space, balcony access, and a dedicated laundry room complete this level. Third Level: The heart of the home, the open-concept great room, is designed for seamless indoor- outdoor living. High ceilings and wraparound balconies maximize the Gulf views, while the chef’s kitchen impresses with a premium Viking appliance package, solid wood cabinetry, and stunning Calacatta Quartz countertops. A guest suite/office adds versatility to the space. Step outside to your own private oasis, where lush landscaping surrounds a sparkling pool and patio area—ideal for relaxation or entertaining. With its prime location, unparalleled craftsmanship, and luxury amenities, La Linda offers an exceptional opportunity to own a modern coastal masterpiece on Siesta Key. Don’t miss your chance to experience the pinnacle of island living—schedule your private tour today!
3706 80TH DR E, SARASOTA, FL 34243
$950,000216 Days on yellowkey MLS ID: A4671730
0 Days Off yellowkey (back on 5/11/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2920 Built: 2007Monthly Fee: $160 Tax: $11,775 (2025)Community: Residences At University GrovesSpa: YesSingle Family
Taxes:$11,775
Elementary School: Kinnan Elementary
High School: Southeast High
Middle School: Braden River Middle
Remarks: Under contract-accepting backup offers. Welcome to one of the most distinctive homes in The Residences at University Groves — a builder’s model home thoughtfully designed with upgraded finishes and architectural details rarely found in comparable homes. Offering nearly 3,000 square feet of living space, this residence is among the larger homes in the community and showcases the enhanced craftsmanship and design features typically reserved for showcase model properties. Recently freshly painted and meticulously maintained, the home is bright, current, and completely move-in ready.From the moment you enter, the home reveals the design touches that set a model residence apart: soaring ceilings, generous living spaces, and elegant architectural details that create a sense of openness and sophistication. The floor plan flows seamlessly between the main living areas, making the home ideal for both everyday living and entertaining. The kitchen serves as the heart of the home, with abundant cabinetry, generous workspace, and easy connection to the surrounding living and gathering areas. Whether hosting guests or enjoying quiet evenings at home, the layout supports a comfortable Florida lifestyle. The primary suite provides a spacious private retreat, while the additional bedrooms offer flexibility for guests, home offices, or extended family. Each room benefits from the thoughtful design and upgrades typically included in a builder’s model home. Situated on a generous .27-acre homesite, the property offers both space and privacy within a peaceful residential setting. Mature landscaping enhances the outdoor environment, creating an inviting backdrop for enjoying Sarasota’s year-round sunshine. The location offers exceptional convenience, placing residents just minutes from: University Town Center (UTC) shopping and dining, Sarasota-Bradenton International Airport (SRQ), Downtown Sarasota’s cultural district, Lakewood Ranch, World-renowned Gulf Coast beaches. Homes with this level of space, upgraded design, and location in the University corridor are increasingly difficult to find. For buyers seeking a move-in-ready Sarasota home with model-home upgrades and exceptional square footage, this property represents a compelling opportunity
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Lee Brewer (941-724-3448)
4252 BOSWELL PL, SARASOTA, FL 34241
$774,900217 Days on yellowkey MLS ID: A4670812
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2533 Built: 1993Monthly Fee: $27 Tax: $5,951 (2025)Community: Bent Tree VillageSingle Family
Taxes:$5,951
Elementary School: Lakeview Elementary
Middle School: Sarasota Middle
Remarks: WOW! This stunning 4-bedroom, 3-bath, 3-car garage split-plan pool home is perfectly situated near the end of a quiet cul-de-sac. Completely remodeled from top to bottom and beautifully designed in a modern contemporary style! Enjoy exceptional living space with a formal living and dining area, plus a gorgeous new kitchen that opens to a large family room with a modern electric fireplace and casual dinette area. The spacious master suite offers a luxurious bath with a freestanding tub, oversized walk-in shower with dual rain heads, and double vanities. Bedroom 2 includes its own ensuite bath that also serves as the pool bath, while Bedrooms 3 and 4 share a well-appointed bath. Step outside to your private backyard with a refinished pool and rescreened pool cage, perfect for relaxing or entertaining. The 3-car garage provides plenty of room for vehicles and storage. Newer roof AC and irrigation system. Located near top-rated schools, golf course views. This home truly checks all the boxes!
Listing is courtesy of: DALTON WADE INC (888-668-8283)
Listing Agent: Sylvia Munia (914-400-4761)
3642 DOVER DR, SARASOTA, FL 34235
$289,00069 Days on yellowkey MLS ID: A4689634
Bed: 4 Bath: 2.0 Liv Area Sq Ft: 1417 Built: 1958 Tax: $3,031 (2025)Community: Kensington ParkSingle Family
Taxes:$3,031
Remarks: This 4-bedroom, 2-bath block home with 1,417 sq ft offers great potential with its sparkling pool, cozy wood-burning fireplace, and spacious layout featuring both a living room and family room. Vaulted ceilings add an open, airy feel, while the indoor laundry room provides everyday convenience. The fenced backyard is perfect for privacy and outdoor enjoyment. Bring your decorative ideas and bring the sparkle back. Ideally situated near the interstate, shopping, and dining for easy access to everything you need.
Listing is courtesy of: ALLEGIANT REAL ESTATE GROUP (941-685-3958)
Listing Agent: Lori Campbell (941-685-3958)
5420 CICERNONE ST #203, SARASOTA, FL 34238
$465,00048 Days on yellowkey MLS ID: A4691603
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1526 Built: 2019Monthly Fee: $384 Tax: $4,116 (2025)Community: Esplanade On Palmer RanchCondo
Taxes:$4,116
Elementary School: Laurel Nokomis Elementary
High School: Venice Senior High
Middle School: Laurel Nokomis Middle
Remarks: One or more photo(s) has been virtually staged. Perfectly suited as either a vacation getaway or full-time residence, this beautifully maintained second-floor condo is located in the highly sought-after, resort-style community of Esplanade on Palmer Ranch. Built in 2019, this 2-bedroom, 2-bathroom condo with a den showcases numerous upgrades throughout, including plantation shutters, Hunter Douglas window treatments, new carpet in the primary bedroom, and all-new light fixtures. The property also includes a single-car detached garage along with a designated parking space. Residents of Esplanade on Palmer Ranch enjoy an impressive array of resort-style amenities, including the on-site Bahama Bar restaurant, resort-style pool with spa, resistance pool, fitness center offering studio classes, 8 pickleball courts, 2 tennis courts, 3 dog parks, and scenic nature trails. The community also provides direct access to the Legacy Trail and is located in close proximity to Oscar Scherer State Park. More than just a home, this property offers a lifestyle centered around comfort, activity, and relaxation. Schedule your private showing today!
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Mark Quire (941-993-5706)
50 CENTRAL AVE #15A, SARASOTA, FL 34236
$1,290,000131 Days on yellowkey MLS ID: A4681474
REDUCED by $40,000 (3.0%) on 05/11/2026
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1595 Built: 2005Monthly Fee: $1,754 Tax: $9,029 (2024)Community: Plaza At Five PointsSpa: YesCondo
Taxes:$9,029
Elementary School: Southside Elementary
Middle School: Booker Middle
Remarks: New Price- for this PRISTINE residence on Central Ave, a rare opportunity to live at the HEART of downtown Sarasota while enjoying the calm, privacy, and personal service of a boutique luxury building, only 49 units. A quality of life can be found at the residence 15A Plaza Five Points. Plan to visit; this residence is located in the city’s historic "Five Points"—long recognized as the cultural and social crossroads of downtown—this address is adjacent to the park, the bayfront, library, theaters, nearby galleries, restaurants, breakfast stops, the farmers markets, Whole Foods, and signature Sarasota events at the Opra House all just steps from your door. See our photos. This 15th-floor residence provides city views and is a healthy 1,595 square feet. This offering includes two bedrooms, two bathrooms, and a well-appointed kitchen with European-style wood cabinetry that delivers a clean, warm, modern look, paired with consistent, full-height cabinet runs that signal storage, symmetry, and design discipline. An efficient open layout and higher elevated city views from the corner lanai. The floor plan balances interior openness with privacy; see the 3D plan in the photo display. This offering is ideal for full-time living or a refined lock-and-leave retreat. Secure parking and dedicated storage enhance day-to-day convenience. Plaza Five Points is intentionally uniquely different. AGAIN, only 49 residences, the building offers a quiet, uncrowded atmosphere rarely found in downtown high-rises. Residents frequently note the sense of calm, privacy, and personal service while still enjoying an active, welcoming community. An added benefit is that the building is self-managed, with long-tenured on-site leadership and staff who know the property well, so you can expect consistent care, cleanliness, and service. Amenities are designed for real living: a heated pool with full-sun exposure, a spa, a beautifully updated clubroom overlooking the pool, a full guest suite is available for your visitors with step-out access to the pool area, concierge services, secure package handling, and a well-equipped fitness center. Optional social engagement includes organized gatherings and group outings, while still preserving a respectful, low-key environment. Built in 2005 to modern hurricane standards, Plaza Five Points has long been admired for its construction quality, intimate scale, and enduring appeal. Market appeal reinforces the long-term value of residences at this address—particularly when offered in alignment with market expectations. A rare downtown Sarasota offering where location, culture, privacy, and warmth come together—Residence 15A delivers not just a home, but a lifestyle rooted in connection, walkability, and quiet sophistication. Schedule a private showing today.
Listing Agent: Andy Scherer (315-264-0944)
1201 E PEPPERTREE DR #234, SARASOTA, FL 34242
$799,000142 Days on yellowkey MLS ID: A4679932
3 Days Off yellowkey (back on 5/11/2026)
Bed: 3 Bath: 2.5 Liv Area Sq Ft: 1686 Built: 1972 Tax: $4,526 (2025)Community: Peppertree Bay ITownhouse
Taxes:$4,526
Remarks: Under contract-accepting backup offers. Private end-unit residence at Peppertree Bay with outdoor patio space, lush tropical landscaping, and an easy stroll to the bayside community pool from the back door. Inside, you’ll find extensive renovations and updates throughout, including new flooring, doors, fans and fixtures, walls, baseboards, and cabinetry. Major system improvements have also been completed, including waste lines, A/C, appliances and washer, dryer. Both the primary and guest baths have been updated along with a major enhancement to the kitchen. The 1st and 2nd floor lanai windows have been recently replaced—bringing in light while providing enhancing comfort and extended living space. A rare combination of privacy, thoughtful upgrades, and that classic Peppertree Bay lifestyle on Siesta Key. Must see and easy to show.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Camille Buck (941-894-4771)
1289 42ND ST, SARASOTA, FL 34234
$289,99944 Days on yellowkey MLS ID: A4691601
Bed: 3 Bath: 1.0 Liv Area Sq Ft: 1232 Built: 1997 Tax: $720 (2025)Community: SunnybrookSingle Family
Taxes:$720
Elementary School: Tuttle Elementary
High School: Booker High
Remarks: **This is the One!** Welcome to this inviting Sarasota home, an ideal location that is growing and close to everything you need! Close proximity to Ringling College, Bayfront Park, SRQ International Airport, Downtown Sarasota and more! **New Roof in 2024** This property offers a comfortable layout with bright living spaces and plenty of natural light throughout. Recently remodeled kitchen with granite countertops and stainless steel appliances! Whether you're a first-time homebuyer, seasonal resident, or investor, this property presents a fantastic opportunity to own in an area with strong potential and continued growth. Located in city limits, weekly rentals are allowed with a 7-day minimum! Don’t miss your chance to make this Sarasota home your own! **THIS PROPERTY QUALIFIES FOR A 1% LENDER INCENTIVE IF USING PREFERRED LENDER. INQUIRE FOR MORE DETAILS.**
Listing is courtesy of: HARRY ROBBINS ASSOC INC (941-924-8346)
Listing Agent: Ryan Miller (941-954-6925)
412 PHEASANT WAY, SARASOTA, FL 34236
$2,995,000265 Days on yellowkey MLS ID: A4666317
REDUCED by $100,000 (3.2%) on 05/06/2026
Bed: 4 Bath: 3.0 Gar: 3 Liv Area Sq Ft: 2677 Built: 2018Monthly Fee: $110 Tax: $29,755 (2025)Community: Bird Key SubSpa: YesSingle Family
Taxes:$29,755
Remarks: Under contract-accepting backup offers. Stunning value for newer build Garden Home on Bird Key! Welcome to Bird Key, Sarasota’s premier island neighborhood perfectly nestled between the heartbeat of downtown Sarasota and the allure of St. Armands Circle. This newer custom-built residence combines elevated design with impact-rated windows as well as newer construction and thoughtful upgrades throughout. Step inside and be captivated by the open great room, which features wide-plank hardwood flooring, tray ceilings with wood beams, custom wall treatments, and automated blinds. The chef’s kitchen is crafted with quartz counters, Bosch stainless steel appliances, a center island with bar seating, walk-in pantry, and a beautifully tiled backsplash. The primary suite is a private sanctuary with direct pool access, dual custom walk-in closets, and a spa-inspired bath with a free-standing soaking tub and dual-entry shower. Guests are treated to two additional stylish en-suite bedrooms, while the versatile fourth bedroom is currently used as a office. Enjoy entertaining in the lush outdoor backyard space, which includes a heated saltwater pool and spa with LED lighting, pavered deck, wood-accent ceiling, and a full summer kitchen with refrigeration and a plumbed-in gas grill. Additional features include a concrete tile roof, tankless gas water heater, irrigation system, custom exterior trim work, and a 3-car garage. Lightly lived in as a seasonal retreat, this home is available with an optional furniture package for effortless move-in. Bird Key living comes with the option to join the Bird Key Yacht Club for an additional fee. The club is currently being rebuilt into a beautiful state-of-the-art facility — just moments from your doorstep. This is more than a home – it’s the Bird Key lifestyle. Schedule your private showing today and claim your place in one of Sarasota’s most coveted addresses.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Drew Russell (941-993-3739)
3328 TOBERO LN, SARASOTA, FL 34235
$729,00050 Days on yellowkey MLS ID: A4691639
Bed: 4 Bath: 3.0 Gar: 2 Liv Area Sq Ft: 2438 Built: 1982 Tax: $2,976 (2025)Community: Tobero WoodsSpa: YesSingle Family
Taxes:$2,976
Elementary School: Gocio Elementary
Remarks: One or more photo(s) has been virtually staged. Welcome to your private country retreat—where comfort, charm, and space come together to create the perfect place to call home. Nestled on a quiet dead-end road and set on over half an acre, this inviting two-story residence offers the peace and privacy you’ve been searching for, surrounded by lush greenery and natural beauty. A warm and welcoming front porch sets the tone, ideal for morning coffee or unwinding at sunset. Inside, you’ll find a thoughtfully designed layout featuring three spacious bedrooms upstairs and the primary suite with separate rooms which could be converted to create an ideal private space for family. There is an additional office or den space on the first level which could easily accommodate a 4th bedroom with large closet and storage. The home is perfectly suited for both everyday living and entertaining. The beautifully updated kitchen is the heart of the home, showcasing granite countertops, stainless steel appliances, and crisp white cabinetry with convenient pull-out drawers. It flows seamlessly into the family and dining areas, highlighted by rich engineered oak wood flooring that adds both style and durability. Practical touches like an upstairs laundry chute leading to the lower-level laundry room make daily living effortless, while major updates—including a new roof (2023), hot water heater (2025), and dual A/C units (2019)—offer peace of mind for years to come. Step outside and discover your own fenced backyard oasis with ample space and lighting. Designed for entertaining, the expansive brick-paver patio and soaring screened lanai create the perfect setting for gatherings. The private heated pool—with a new heat pump, outdoor hot/cold shower, fire pit, and fully fenced yard—delivers a true resort-style experience right at home. Additional highlights include a spacious garage with a hurricane-rated door, ample storage, a whole-house attic fan, and on the opposite side of the home a private outdoor area complete with its own porch with dedicated power for future self-contained spa and shell deck. The well on the property has a new tank and services 6 water bibs around the exterior. Lovingly maintained by its original owners, this home combines tranquil country living with everyday convenience—just minutes from shopping, dining, an organic farm, and walking distance to Gocio Elementary School. Don’t miss the opportunity to experience this exceptional property—be sure to explore the 3D and aerial tours.
Listing is courtesy of: GENEROUS PROPERTY (941-275-9399)
Listing Agent: Joyce Sacco (941-445-3937)
2544 ORSOVA WAY, SARASOTA, FL 34231
$495,00042 Days on yellowkey MLS ID: A4692439
0 Days Off yellowkey (back on 5/8/2026)
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1545 Built: 1964 Tax: $4,594 (2025)Community: Phillippi Gardens 14Spa: NoSingle Family
Taxes:$4,594
Remarks: Tucked away in one of South Sarasota's most coveted neighborhoods, this exceptional property offers the rare combination of tranquil privacy and unbeatable convenience. Nestled just off Constitution Boulevard south of Phillippi Creek, the setting feels like a retreat — yet world-class dining, boutique shopping, and the pristine shores of Siesta Key's award-winning beach are all within a mile from your front door. Inside, every detail has been thoughtfully curated for effortless, modern living. Sleek wall-to-wall ceramic tile flows throughout the home, while a fully upgraded second bathroom showcases premium finishes with no detail overlooked. The master bath has also been beautifully refreshed with new tile and cabinetry, delivering a spa-like feel you'll love coming home to. Step outside to your own private oasis — a spacious heated pool, recently resurfaced and encased in a brand-new screen enclosure, perfect for year-round entertaining. Host effortlessly, unwind completely, and create lasting memories in a backyard built for both. Peace of mind comes standard here. A brand-new roof (Fall 2025) backed by a 15-year warranty, new hurricane-impact windows (Fall 2025), fresh exterior paint, and manicured landscaping mean this home is truly move-in ready from day one. An oversized two-car garage rounds out the package with the storage and functionality today's buyers demand. BEST OF ALL— NO HOA, NO DEED RESTICTIONS, and NO CDD. This is the freedom to live on your terms, in a home that has it all.
Listing is courtesy of: KELLER WILLIAMS SUBURBAN TAMPA (813-684-9500)
Listing Agent: Aaron Wittenstein (941-299-1151)
800 N TAMIAMI TRL #103, SARASOTA, FL 34236
$620,000119 Days on yellowkey MLS ID: A4682840
Bed: 1 Bath: 3.0 Gar: 1 Liv Area Sq Ft: 1684 Built: 2007 Tax: $7,240 (2025)Community: AlinariSpa: YesCondo
Taxes:$7,240
Elementary School: Alta Vista Elementary
Remarks: Welcome to Unit 103 at Alinari at Rosemary Place, a distinguished residence within one of downtown Sarasota’s premier luxury condominium addresses. Positioned in the vibrant Rosemary District, this spacious first-floor garden-style home offers the rare combination of elegant design, generous scale and desirable ground-level access, delivering comfort of a private residence with the ease of maintenance-free condominium living. Encompassing 1,684 square feet of heated living space and 1,936 total square feet including the outdoor patio, this one-bedroom plus loft residence with three full baths lives exceptionally large. High volume ceilings, expansive glass windows, and sliding doors flood the interiors with natural light, creating an airy ambiance and seamless indoor-outdoor flow. The open and flexible floor plan offers well-proportioned living and dining areas ideal for everyday living and effortless entertaining. The thoughtfully designed layout allows versatility to suit your lifestyle, whether designing a refined lounge, home office, guest retreat or creative loft space. The kitchen integrates beautifully with the main living areas, encouraging intimate evenings and casual gatherings. Multiple full baths provide exceptional convenience and privacy for residents and visitors alike. With building no stairs or elevators required to access your residence, this distinctive residence delivers accessibility and discretion. Alinari elevates daily living with an exceptional suite of resort-style amenities, including 24-hour concierge and security, a heated pool and spa, state-of-the-art fitness center, club room, theater, wine room, business center, library, grilling area, and guest suites for visiting family and friends. The 18-story reinforced concrete high-rise features refined plazas, fountains, a private recreational parcel, redesigned lobby and full front-desk services. Recent 2025 enhancements include upgrades to the pool area, planters, theater, game room and catering kitchen. In Flood Zone X and outside the floodplain, Alinari’s lobby and guest parking are elevated approximately 17 feet above base sea level, with residential garage parking positioned more than 30 feet above sea level. This residence includes a secured garage parking space and a climate-controlled assigned storage unit. The association maintains strong reserves with no current or upcoming assessments. Moments from Bayfront Park, Sarasota’s waterfront promenade, world-class dining, cultural venues, boutiques and evolving Sarasota Bay Park project, this residence captures the essence of downtown Sarasota luxury living with coastal accessibility. Unit 103 represents a rare opportunity for refined ground-level living in one of Sarasota’s established and architecturally distinguished condominium communities, where comfort, convenience and elevated Florida living converge.
Listing Agent: Moriah Taliaferro (941-504-9910)
5476 SWIFT RD #19, SARASOTA, FL 34231
$147,90064 Days on yellowkey MLS ID: A4689984
REDUCED by $7,000 (4.5%) on 05/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1095 Built: 1981 Tax: $2,164 (2025)Community: Imperial PlaceCondo
Taxes:$2,164
Remarks: Live the Florida lifestyle you’ve been dreaming of—just minutes from the powdery white sands of Siesta Key Beach. This rarely available ground-floor, two-bedroom, two-bath end-unit condo combines location, upgrades, and effortless living in one exceptional package. From the moment you step inside, you’ll notice the light-filled, airy feel enhanced by extra windows—an exclusive perk of end-unit living—and a desirable south-facing position. This home features newer luxury vinyl flooring, newer appliances, impact windows (2019), AC (2020), and a brand-new roof (2025), offering true peace of mind. The open-concept layout seamlessly connects the living, dining, and kitchen areas—perfect for entertaining or simply relaxing after a day at the beach. Step outside through sliding glass doors to your oversized screened-in patio, where morning coffee and evening breezes become part of your daily routine. Located in Imperial Place, residents enjoy a community pool and convenient access to nearby attractions all while being just minutes from shopping, dining, and everyday essentials at Detwiler's Farm Market and the nearby Costco. Plus, you’re within easy reach of Downtown Sarasota, Venice, Sarasota-Bradenton International Airport, The Mall at University Town Center, and the natural beauty of Myakka River State Park. Whether you’re searching for a full-time residence, seasonal escape, or income-producing investment, this is the kind of opportunity that doesn’t last.
Listing Agent: Daniel Jasmer (941-284-9893)
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