Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
340 JACKSON DR, SARASOTA, FL 34236
$4,250,000391 Days on yellowkey MLS ID: A4653979
Bed: 6 Bath: 5.5 Gar: 2 Liv Area Sq Ft: 3470 Built: 2019 Tax: $39,852 (2024)Community: Saint Armands Div John Ringling EstatesSpa: YesSingle Family
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$39,852
Elementary School: Southside Elementary
High School: Sarasota High
Tax Year: 2024
Middle School: Booker Middle
Remarks: STUNNING ESTATE ON LIDO KEY!!! WELCOME TO YOUR COASTAL DREAM HOME!!! This 6 bedroom 5 1/2 bath property is TURNKEY FURNISHED, has an ELEVATOR to all levels, and boasts vaulted ceilings. The owner spared no expense when building this home. High end designer finishes and attention to detail are evident throughout. The master bedroom is a tranquil oasis and offers a private balcony providing breathtaking views. You will also find a large walk in closet and an oversized bathroom featuring double vanities, free standing bath tub, and a walk in shower. The additional four bedrooms are all en-suite and are laid out perfectly. The chef's kitchen has high end wood cabinets, quartz countertops, stainless steel appliances and a large center island. The great room floor plan is expansive and features high ceilings with wood beams. Step into your outdoor oasis with a private heated pool with a sun shelf, perfect for both kids and adults to soak up the Florida sun. A covered spa ensures year-round enjoyment. The expansive covered patio extends nearly the entire space beneath the home, ample bar-top seating, dining, TVs, and gaming areas, including a pool table and foosball. Convenience is key as you're just a short stroll to Lido Key Beach and or to St. Armand's Circle with wonderful shops and restaurants. With a 2-car garage and space for up to four cars in the driveway, you have ample parking options. This is the ultimate vacation home for you and your family. Currently a successful vacation rental with forward bookings in place.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
4136 ROBERTS POINT CIR, SARASOTA, FL 34242
$4,900,000230 Days on yellowkey MLS ID: A4670896
Bed: 6 Bath: 6.0 Gar: 10 Liv Area Sq Ft: 7099 Built: 2008 Tax: $49,708 (2024)Community: Roberts Point 2Spa: YesSingle Family
Taxes:$49,708
Elementary School: Phillippi Shores Elementary
Middle School: Brookside Middle
Remarks: Discover waterfront living on the coveted north end of Siesta Key. Set along South Coconut Bay with access to Roberts Bay and the Intracoastal Waterway, this sprawling estate offers exceptional privacy, water views, and over 7,000 square feet of refined living space. Soaring ceilings and walls of glass fill the home with natural light, while the open-concept layout and contemporary design create an ideal setting for both everyday living and entertaining. A cylindrical glass elevator serves as a subtle architectural feature within the home’s modern design. The gourmet kitchen is appointed with custom cabinetry, premium appliances, and Sub-Zero refrigeration, complemented by a built-in coffee system, 140-bottle wine cooler, and an oversized island designed for gathering. Multiple fireplaces add warmth throughout the home, while the private home theater with refreshment bar offers an elevated entertainment experience. Outdoor living includes expansive terraces, an infinity-edge pool and spa, and peaceful bayfront surroundings. The primary suite features a private waterfront terrace, fireplace, sitting area, dual walk-in closets, and morning bar. Built with reinforced concrete construction and Anderson hurricane casement windows, the home blends luxury with durability. Additional highlights include a 10-car garage, gym, office, and generously sized guest accommodations. Meticulously maintained, the home also features a freshly painted exterior. A rare opportunity on one of Siesta Key’s most sought-after streets.
Listing is courtesy of: KELLER WILLIAMS ON THE WATER S (941-803-7522)
Listing Agent: Nina Bayan (941-716-5622)
838 NORSOTA WAY, SARASOTA, FL 34242
$4,190,00085 Days on yellowkey MLS ID: A4688144
0 Days Off yellowkey (back on 5/14/2026)
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 3001 Built: 2026 Tax: $11,779 (2025)Community: Bay IslandSingle Family
Taxes:$11,779
Tax Year: 2025
Remarks: Under contract-accepting backup offers. Pre-Construction. To be built. Discover timeless coastal elegance in this upcoming traditional-style new construction home, perfectly situated in the highly coveted Bay Island neighborhood on Siesta Key. Designed to blend modern sophistication with classic charm, this residence offers an extraordinary lifestyle of luxury and tranquility. Set on a 13,815 sqft. homesite, this 3,001 sqft. masterpiece features 5 spacious bedrooms, 5 full bathrooms, 2 half baths, and an office. There is opportunity for a private fitness studio, and there are 3 garage spaces. Thoughtfully curated interiors showcase refined finishes, soaring ceilings, and abundant natural light that capture lush landscaping views throughout. At the heart of the home lies a gourmet chef’s kitchen—a showpiece of design and functionality. A striking quartz waterfall island anchors the open-concept layout, framed by elegant pendant lighting, custom cabinetry, and top-of-the-line stainless steel appliances. Perfectly suited for entertaining or relaxed coastal living, the adjoining living and dining areas flow seamlessly to the outdoors. Step into your private tropical retreat, where a resort-style pool with a champagne spa is surrounded by lush landscaping and swaying palms. Host the family or guests with the covered outdoor kitchen and the dinning space. The outdoor living space is designed for serenity and sophistication, offering the ideal backdrop for gatherings or quiet moments alike. Located in one of Sarasota’s most desirable neighborhoods, this remarkable new construction home offers privacy, convenience, and effortless access to world-class beaches, fine dining, and vibrant cultural attractions. A rare opportunity to own a brand-new luxury residence on Bay Island—where coastal beauty meets timeless design.
Listing is courtesy of: PHAM REALTY GROUP LLC (941-260-0709)
Listing Agent: Faith Stutzman (941-260-0709)
3700 S OSPREY AVE #214, SARASOTA, FL 34239
$299,000261 Days on yellowkey MLS ID: A4667426
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 991 Built: 1979 Tax: $2,282 (2025)Community: Plaza GardensCondo
Taxes:$2,282
Remarks: Perfect Investment Property! Discover Your Ideal Retreat at Plaza Gardens in Sarasota! Welcome to this beautifully remodeled, fully furnished two-bedroom condo situated in the heart of Sarasota! Surrounded by lush tropical greenery and well-kept gardens, this boutique-style residence is the perfect escape for those seeking a serene beach getaway. Located just southeast of Siesta Key’s North Bridge, you're only minutes away from stunning Siesta Key beaches for sun-soaked relaxation. Enjoy the convenience of nearby shopping with Morton’s Market and Publix just around the corner. Downtown Sarasota, known for its vibrant shopping, dining, and cultural experiences, is also a short drive away. This thoughtfully designed condo features an open floor plan that maximizes space and comfort. The modern kitchen comes equipped with new stainless steel appliances, stylish cabinetry, and sleek quartz countertops, perfect for meal preparation. With easy-to-maintain wood laminate flooring and a spacious bathroom accessible from both bedrooms, this unit ensures privacy and comfort. The primary suite includes a cozy alcove with a built-in cabinet and chic quartz countertop for a washer and dryer, blending style with functionality. This turn-key condo is an excellent opportunity for seasonal rentals! With low association fees and a prime location, it’s ideal for vacationers looking to experience the charm of Sarasota and its beautiful beaches. Don't miss out on this exceptional chance to own a piece of paradise at Plaza Gardens. Experience the perfect blend of relaxation, convenience, and investment potential today!
Listing is courtesy of: COLDWELL BANKER REALTY (941-366-8070)
Listing Agent: Andrea Cohen (786-773-0370)
800 BENJAMIN FRANKLIN DR #509, SARASOTA, FL 34236
$999,00051 Days on yellowkey MLS ID: A4691604
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1150 Built: 1978 Tax: $13,735 (2025)Community: Lido AmbassadorCondo
Taxes:$13,735
Remarks: WELCOME to the Lido Ambassador where a true beachfront residence with a NEW A/C unit becomes your everyday reality. PERFECTLY positioned directly on the sands of Lido Beach, this exceptional offering captures unobstructed, panoramic views of the Gulf of Mexico. There are no angles, no interruptions, just an uninterrupted horizon of turquoise water and unforgettable sunsets. This is coastal living in its purest, most elevated form. THIS two-bedroom, two-bathroom residence is thoughtfully designed, with water views from every room, including the primary suite, guest bedroom, and main living areas. Even from the kitchen, the gentle rhythm of the waves becomes part of your daily experience. Situated on an upper floor, the vantage point enhances both the depth of the Gulf views and the drama of Sarasota’s celebrated sunsets. THE layout offers a seamless canvas, perfectly livable as is, yet equally compelling for a bespoke redesign tailored to your personal vision. For the discerning buyer, it presents a rare opportunity to curate a refined beachfront retreat in one of Sarasota’s most coveted locations. THE community itself has been thoughtfully refreshed, with a newly enhanced poolside environment and updated outdoor spaces designed to feel both inviting and serene. WHILE amenities include a fitness room and meeting space, the true luxury lies just beyond your door with the sand beneath your feet and the sound of the Gulf as your constant backdrop. LOCATION here is effortless. Ideally positioned on Lido Key, you are moments from the charm and sophistication of St. Armands Circle, known for its boutiques, fine dining, and vibrant social scene. Nearby, Ted Sperling Park offers a more natural escape with kayaking and mangrove trails, while the neighboring Lido Beach Resort provides the added luxury of a beachfront dining experience at its iconic tiki bar or fine dining at The Drift Kitchen and Bar. THIS is a place where mornings begin with tranquil walks along the shoreline and evenings are defined by the glow of the setting sun over the Gulf. It is a setting that must be experienced to be fully appreciated—serene, rare, and undeniably captivating. PRIVATE showings are encouraged.
Listing is courtesy of: DOUGLAS ELLIMAN (941-867-6199)
Listing Agent: Lisa Otte (941-281-5472)
253 GOLDEN GATE PT #303, SARASOTA, FL 34236
$3,195,00042 Days on yellowkey MLS ID: A4693541
0 Days Off yellowkey (back on 5/13/2026)
Bed: 3 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 3068 Built: 2025Monthly Fee: $3,084 Tax: $19,307 (2025)Community: Peninsula SarasotaCondo
Taxes:$19,307
Middle School: Sarasota Middle
Remarks: Newly completed, Peninsula Sarasota is ideally positioned in the coveted Golden Gate Point neighborhood, offering a peaceful residential retreat just moments from the vibrancy of downtown Sarasota. Designed by Blu Interiors, each residence showcases contemporary modern elegance with calming, sophisticated palettes, soaring ceilings, and expansive wraparound terraces that seamlessly blend indoor and outdoor living. Every element reflects a thoughtful commitment to refined luxury. State-of-the-art kitchens feature sleek European cabinetry, gas cooktops, and quartz countertops, complemented by premium Wolf and Sub-Zero appliances. Additional highlights include hardwood flooring throughout, floor-to-ceiling windows that flood the home with natural light, and a private terrace equipped with a gas grill—perfect for effortless entertaining. The spacious owner’s retreat serves as a true sanctuary, complete with generous walk-in closets, dual vanities, a soaking tub, and an oversized walk-in shower for spa-like relaxation. Residents enjoy on-site concierge services and secure, access-controlled underground parking for two vehicles, including an EV charging station. A private foyer and dedicated elevator provide direct access to exceptional amenities such as a resort-style pool and state-of-the-art fitness center, while the elegant owner’s club room offers private wine storage for each residence. The communal rooftop terrace sets the stage for unforgettable gatherings, boasting sweeping panoramic and sunset views. Peninsula Sarasota delivers a truly elevated lifestyle within a lush, tropical setting—just minutes from Sarasota’s celebrated arts, culture, dining, and award-winning beaches. A rare opportunity to experience sophisticated coastal living.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Georgia Salaverri (954-661-8968)
5151 SAINT ALBANS AVE, SARASOTA, FL 34242
$1,095,000267 Days on yellowkey MLS ID: A4666929
Bed: 4 Bath: 3.5 Liv Area Sq Ft: 2314 Built: 1963 Tax: $8,056 (2025)Community: Siesta BeachSpa: YesSingle Family
Taxes:$8,056
Remarks: Under contract-accepting backup offers. Charming Coastal Oasis in the Heart of Siesta Key Nestled on a serene, tree-lined property, this inviting 4-bedroom, 3.5-bath beach-style home offers the perfect blend of tranquility, charm, and central location. Step into a spacious, light-filled living area with an open kitchen layout—ideal for hosting friends and making family memories. Freshly updated with new paint, gleaming quartz countertops, and stainless steel appliances, this move-in-ready home is designed for easy, coastal living. The open floor plan includes a spacious upstairs primary suite with French doors leading to a private balcony—your own quiet retreat. Three additional guest bedrooms are thoughtfully located on the first floor, including a separate guest suite with its own private entrance, offering comfort and flexibility. Step outside into your private backyard oasis featuring a beautiful pool and spa, fully enclosed with a lovely paver deck—perfect for relaxing, entertaining, or enjoying sunny Florida days in peace and privacy. There's still plenty of yard space to garden or play. Slip on your sandals for a short stroll to the world-famous Siesta Key Beach, ranked #1 in the U.S. by TripAdvisor, or bike to the charming Siesta Key Village with its eclectic mix of shops, restaurants, and entertainment. Don’t miss this peaceful, spacious retreat—your own slice of paradise on Siesta Key.
Listing Agent: Dianne Anderson (941-350-3513)
3550 SARASOTA GOLF CLUB BLVD, SARASOTA, FL 34240
$4,500,000215 Days on yellowkey MLS ID: N6141577
Bed: 5 Bath: 6.0 Gar: 3 Liv Area Sq Ft: 9018 Built: 2004 Tax: $24,425 (2024)Community: Palmer Farms 3RdSpa: YesSingle Family
Taxes:$24,425
Elementary School: Tatum Ridge Elementary
Middle School: McIntosh Middle
Remarks: Set behind a private gated entrance and approached by a sweeping drive that curves around the front pond, this 5.6-acre Sarasota estate offers privacy, size and distinction, along with a long list of high-end improvements. upgrades include a 2025 roof, brand-new whole-home generator, comprehensive smart-home systems, a new pool deck with pavers and turf, 4-hole putting green, new outdoor kitchen, refreshed irrigation well (2024), reverse-osmosis well system, 5 AC units, 2 gas tankless water heaters, 2 in-ground propane tanks, 500 Gallon RO Tank, a 1450 aeroator tank, and refined interior details such as Venetian plaster walls and custom cherry wood in-lay flooring in the game room loft area. The result is a property that feels both luxurious and exceptionally well cared for. Beyond the upgrades, the home offers more than enough space for large-scale living and entertaining. The main living areas are anchored by a 24-foot high ceiling in the great room, a dedicated theater room, and an expansive game room/loft area with full bar, balcony, and additional loft space. Smart-home features include a phone-controlled gate system, whole-property cameras, Sonos audio, smart garage access, and an integrated alarm system. The primary suite occupies its own wing, designed with two oversized walk-in closets, a private exercise room with sauna, and a spa-like bathroom featuring a jacuzzi tub, dual sinks, and a large shower with double heads and body sprays. Four additional en-suite bedrooms include features such as private balconies, outdoor entrances, oversized closets, and a convenient laundry chute. Each bedroom offers generous square footage, giving guests or family members plenty of room to spread out comfortably. Two additional flex rooms offer options for an office, studio, homework area, or additional sleeping space. The kitchen is equipped with GE Monogram built-ins, a Bosch espresso machine, wine cooler, mini fridge, two sinks, and an adjacent formal dining room. Additional interior features include a 3-car garage with specialty flooring and storage systems plus an EV Charger, a dedicated dog spa room, homework/craft/sewing room, separate fenced run, extensive cabinet storage, two staircases, and a spacious laundry room with desk nook. Outdoor living has been fully modernized with a redesigned pool area, electric and gas heaters, pool bath and changing area, and outdoor shower. The property also offers the rare ability to add two additional structures, along with a scenic pond, mature landscaping, and abundant wildlife. Location is another standout feature. While the estate feels tucked away and exceptionally private, it sits just minutes from I-75, offering quick access to the greater Sarasota region. Downtown Sarasota is an easy drive at roughly 10–12 miles, Siesta Key Beach is about 15 miles away, and travel is convenient with SRQ Airport approximately 15–20 miles and Tampa International Airport about 55–60 miles from the propertyThis blend of privacy, acreage, and proximity to everything is truly rare—allowing you to feel worlds away while staying connected to the best of Sarasota. Call for a private tour today.
Listing is courtesy of: KELLER WILLIAMS ISLAND LIFE REAL ESTATE (941-254-6467)
Listing Agent: Michelle Hupp (941-773-5464)
385 AVENIDA MADERA, SARASOTA, FL 34242
$949,000378 Days on yellowkey MLS ID: A4653809
1 Days Off yellowkey (back on 5/13/2026)
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1094 Built: 1958 Tax: $10,923 (2024)Community: Siesta Manor Sec 1Single Family
Taxes:$10,923
Remarks: Under contract-accepting backup offers. Beaches, Boating & Bistros!!! Excellent Investment, 2nd Home or Build new. Island Style Canal Front Home on Siesta Key, steps to World Famous Siesta Village & the cool quartz sands of Siesta Beach. This Island Style 2 bed, 2 bath home in close proximity to all the food & exciting nightlife that Siesta Key has to offer. 1 car garage. This home on a Cul de sac is light & bright with Terrazzo floors for the laid-back Island lifestyle. New roof in 2022. Excellent rental potential with its ideal location makes this property a solid investment. Out back is a huge deck on the Canal that is perfect for waterfront get togethers. Updated kitchen with stainless steel appliances that opens up for entertaining with family & friends. Separate laundry room and a potting shed & workshop. After spending the day on your boat, either cook up your catch or stroll to your favorite Siesta Village establishment. Or, better yet, take a stroll on the Beach & enjoy Sunset.
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Dan Miller (941-376-7442)
98 DADE AVE, SARASOTA, FL 34232
$539,90082 Days on yellowkey MLS ID: TB8491097
REDUCED by $20,000 (3.6%) on 04/19/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 1691 Built: 1978 Tax: $6,124 (2025)Community: Grerrs Homeland RepSingle Family
Taxes:$6,124
Elementary School: Brentwood Elementary
Remarks: Welcome to your private poolside retreat in desirable Sarasota, 5 minutes away from the Gulf Coast beaches. No CDD or HOA. This beautifully updated 3-bedroom, 2-bath home offers a seamless blend of comfort, style and Florida outdoor living. The 1,751 square feet home features an open floor plan designed for everyday living and entertaining. The fully fenced backyard is a true oasis; a setting that creates both privacy and serenity. Floors are wood-look porcelain tile throughout giving this home a modern, easy-care style providing a clean and low maintenance interior with no carpet. The kitchen features newer stainless-steel appliances with ample cabinet storage. The primary suite offers the convenience of an ensuite bath and spacious walk-in closet with custom organizer shelves. On the opposite side of the home, two guest bedrooms and a full bath provide comfort and privacy for family or visitors. Additional features include a 2-car garage with indoor laundry (Newer washer and dryer included) and extra storage. Step outdoors to a living area highlighted with a covered lanai including a New Outdoor Fan (2026), providing shaded seating overlooking the refreshing pool. The backyard offers space for gardening, recreation, or the future addition of an outdoor kitchen and dining area. Major updates include a Roof Replacement (2021), Air Conditioner (2021), Air Handler (2024), Tankless Water Heater (2025), Fresh interior paint (2026), Updated design to baseboards/window casings (2026), Concrete Driveway (2026), New Pool Filter (2026). This could be yours-A well-maintained pool home in a convenient Sarasota location. Ideally located just minutes from shopping, dining, downtown Sarasota, the Legacy Trail, and world-renowned Gulf Coast beaches. This is more than a home—it’s a lifestyle.
Listing is courtesy of: ROGER G KING (916-300-1134)
Listing Agent: Roger King (916-300-1134)
111 S PINEAPPLE AVE #719, SARASOTA, FL 34236
$1,195,000161 Days on yellowkey MLS ID: A4677833
Bed: 2 Bath: 2.5 Gar: 1 Liv Area Sq Ft: 1498 Built: 2019 Tax: $11,001 (2025)Community: Mark Sarasota CondoSpa: YesCondo
Taxes:$11,001
Remarks: Exquisite, elegant, and serene living in the heart of splendid downtown Sarasota! Enjoy the morning on your balcony with your coffee in hand as you enjoy the bird’s eye views, and evenings relishing the Gulf breezes. This gorgeous condo is impeccable with European cabinetry, quartz countertops, custom woodworking, porcelain tiles, refreshing, subtle color palette, California Closets, and more! The open, expansive floor plan boasts natural light galore inspiring a cheery, light-hearted ambiance. The split bedroom layout allows for privacy and generous breathing space when entertaining guests. The primary bedroom is spacious and delightfully opens to the balcony for fresh air, complete with a thoughtfully designed walk-in closet, and a pristine en suite bathroom with dual vanities. The airy guest bedroom and en suite are perfect for hosting family and friends. There is a den for work or hobbies, and a powder room for guests. Spend afternoons by the glorious 65-foot infinity pool with peek-a-boo views of the Gulf! Enjoy all of the splendid, convenient amenities that The Mark offers to compliment your lifestyle: fire pit lounge, cabanas, outdoor grills, fitness center, spin room, clubroom with catering kitchen, pool table, café-style office space, 24-hour staffed reception, pet-friendly, security, an assigned parking space, and a separate secured storage unit. Saunter around downtown Sarasota, shop at the Saturday Farmers' Market, savor the authentic lemon tarts at C’est La Vie, attend the Sarasota Ballet or Orchestra, the lush gardens of Selby, and dozens of delightful restaurants and cafes! Enjoy sunny beach days at Lido Key and powdered sugar-soft beach walks. Evening strolls at the marina only a few blocks away, boutique shopping and street musicians at St. Armand’s Circle, or pop out for a last-minute cocktail at sunset with friends. The Mark is the epitome of downtown easy, breezy, luxury living!
Listing is courtesy of: ROSEBAY INTERNATIONAL REALTY, INC (941-366-7673)
Listing Agent: Autumn Beckett (941-376-6983)
1021 CRESCENT ST, SARASOTA, FL 34242
$1,699,000135 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+
Taxes:$17,389
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)
4252 BOSWELL PL, SARASOTA, FL 34241
$774,900223 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
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)
50 CENTRAL AVE #15A, SARASOTA, FL 34236
$1,290,000137 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
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)
1423 HILLVIEW DR, SARASOTA, FL 34239
$13,900,00096 Days on yellowkey MLS ID: A4686188
Bed: 6 Bath: 8.0 Gar: 8 Liv Area Sq Ft: 11588 Built: 2006Monthly Fee: $21 Tax: $184,274 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$184,274
Remarks: Welcome to a home that lives like a resort in Sarasota’s premier neighborhood, Harbor Acres. With 134 feet of water, this nearly 12,000-square-foot estate is crafted for laid-back luxury and everyday ease, designed for entertaining against breathtaking views of Sarasota Bay, the Ringling Causeway, and the downtown skyline. A paver driveway winds through mature palms to a stone exterior with travertine steps, a porte cochere, and an expansive porch, all setting the tone for within. Solid wood doors open to a soaring foyer with wood columns, intricate millwork, and custom archways that reflect the home’s detailed character. Designed for easy living, the main spaces flow effortlessly, highlighted by a family room with zero-corner sliders, a wall of windows overlooking the water, a coffered wood ceiling, and a stone fireplace that anchors the room. Detailed trim, crown molding, and wood wainscoting add depth and highlight craftsmanship throughout. The kitchen is anchored by a large island with storage, prep space, and a sink, and equipped with top-tier appliances including Dacor double ovens and range, Sub-Zero refrigerator and freezer, dual Bosch dishwashers, a warming drawer, and a Scottsman ice maker. A walk-in pantry with custom shelving keeps everything organized, while the adjacent butler’s or catering kitchen, with its own cooktop, refrigerator, microwave, and desk area, makes entertaining effortless. An eat-in area with an aquarium window and bar-height counter seating keeps it functional and inviting. A wine room with wood-paneled walls and a separate entertaining bar with an oversized wine cooler make this home ideal for gatherings of any scale. The theatre offers the ultimate at-home viewing experience with custom wall and ceiling treatments, tiered seating, blackout glass windows and door, and a built-in bar with sink and additional seating. Outside is an extension of the home’s lifestyle, offering resort-style features meant for everyday use. The pool features a sun shelf, stone accents, and cascading water features paired with a raised spa, while the outdoor kitchen, with grill, refrigerator, and bar seating, makes entertaining effortless. A dedicated pool bath adds convenience, and nearby, the turf yard, fire pit, and hammock invite easy relaxation. A spiral staircase connects the primary suite terrace to the outdoor amenities, and a private dock completes the experience. Back inside, the home offers a thoughtful blend of privacy and flexibility. The primary suite is a retreat with incredible views, French doors to a private terrace, a coffee bar, and a sitting room with a fireplace. Its spa-inspired bath features a jetted tub, multi-head shower, custom dual vanity, and dual walk-in closets. A separate in-law suite provides full independence with its kitchenette, living room, laundry, and terrace. Guests enjoy four additional suites with private baths, a bonus room with a terrace, a fitness room, a built-in homework area, and easy access across all levels via dual staircases and a three-stop elevator. Abundant garage and storage space complete the estate. This Harbor Acres residence delivers the ultimate Sarasota lifestyle, just minutes from downtown, Southside Village, and Gulf beaches. The adjacent vacant lot at 1435 Hillview is currently offered separately, with the opportunity to purchase both together. Bank signoff on the sale of this property may be required. The gate and driveway would need to be reconfigured.
Listing Agent: Joel Schemmel (941-587-4894)
1423 & 1435 HILLVIEW DR, SARASOTA, FL 34239
$17,350,000385 Days on yellowkey MLS ID: A4653958
Bed: 6 Bath: 8.0 Gar: 8 Liv Area Sq Ft: 11588 Built: 2006Monthly Fee: $21 Tax: $238,008 (2025)Community: Harbor AcresSpa: YesSingle Family
Taxes:$238,008
Remarks: Welcome to a home that lives like a resort, set on two lots consisting of 1.8 lush, waterfront acres in Sarasota’s premier neighborhood, Harbor Acres. Crafted for laid-back luxury and everyday ease, this nearly 12,000-square-foot estate offers 249 waterfront feet and is designed for entertaining, all set against views of Sarasota Bay, Ringling Causeway and the downtown skyline. An expansive paver driveway winds through mature palms to a stone exterior with travertine steps, a porte cochere and an expansive porch, all setting the tone for within. Solid wood doors open to a soaring foyer with wood columns, intricate millwork and custom archways that reflect the home’s detailed character. Designed for easy living, the main spaces flow effortlessly, highlighted by a family room with zero-corner sliders, a wall of windows overlooking the water, a coffered wood ceiling, and a stone fireplace that anchors the room. Detailed trim, crown molding, and wood wainscoting add depth and highlight craftsmanship throughout. The kitchen is anchored by a large island with storage, prep space and a sink, and equipped with top-tier appliances including Dacor double ovens and range, Sub-Zero refrigerator and freezer, dual Bosch dishwashers, a warming drawer and a Scottsman ice maker. A walk-in pantry with custom shelving keeps everything organized, while the adjacent butler’s or catering kitchen—with its own cooktop, refrigerator, microwave and desk area—makes entertaining easy. An eat-in area with an aquarium window and bar-height counter seating keeps it functional and inviting. A wine room with wood-paneled walls and a separate entertaining bar with an oversized wine cooler make this home ideal for gatherings of any scale. The theatre offers the ultimate at-home viewing experience with custom wall and ceiling treatments, tiered seating, blackout glass windows and door, and a built-in bar with sink and more seating, ideal for movie nights, game days or entertaining. Outside is an extension of the home’s lifestyle, offering resort-style features meant for everyday use. The pool features a sun shelf, stone accents, and cascading water features paired with a raised spa, while the outdoor kitchen, with grill, refrigerator and bar seating, makes entertaining effortless. A dedicated pool bath adds convenience, and nearby, the turf yard, fire pit and hammock invite easy relaxation. A spiral staircase connects the primary suite terrace to it all, while a versatile sport court and two private docks for 75-plus-foot yachts complete the experience. Back inside, the home offers a thoughtful blend of privacy and flexibility. The primary suite is a retreat with incredible views, French doors to a private terrace, a coffee bar and a sitting room with a fireplace. Its spa-inspired bath features a jetted tub, multi-head shower, custom dual vanity and dual walk-in closets. A separate in-law suite provides full independence with its kitchenette, living room, laundry and terrace. Guests enjoy four more suites with private baths, a bonus room with a terrace, a fitness room, a built-in homework area, and easy access across all levels via dual staircases and a three-stop elevator. Abundant garage and storage space complete the estate. This Harbor Acres home delivers the ultimate Sarasota lifestyle, just minutes from downtown, Southside Village and Gulf beaches. The vacant lot at 1435 Hillview can be separated and the list price reduced accordingly.
825 OSPREY AVE #108, SARASOTA, FL 34236
$495,000111 Days on yellowkey MLS ID: A4684762
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1260 Built: 1985 Tax: $5,113 (2025)Community: Central ParkCondo
Taxes:$5,113
Remarks: Welcome to Central Park I in the heart of downtown Sarasota, where sophisticated design meets an exceptional location. This beautifully renovated 2-bedroom, 2-bath residence presents an effortless, move-in-ready opportunity in one of Sarasota’s most desirable boutique buildings. Offered partially furnished, the thoughtfully reimagined interior features a bright, open-concept layout complemented by refined finishes and curated upgrades throughout. The designer kitchen is both striking and functional, showcasing elegant quartzite countertops and backsplash paired with premium Italian appliances by Bertazzoni and Fulgor Milano—a space equally suited for everyday living and stylish entertaining. The kitchen flows seamlessly into the main living and dining areas, creating an inviting atmosphere filled with natural light. Just beyond, a sunlit alcove provides a serene place to relax and unwind after a day enjoying all that downtown Sarasota has to offer. The living space opens to a southern-facing terrace overlooking Hudson Bayou and the community pool, while a covered portion allows for comfortable year-round outdoor enjoyment. The spacious primary suite serves as a private retreat, featuring elegant French doors leading to a bright east and south-facing terrace. The renovated en-suite bath offers a spa-like experience with a walk-in shower, stone vanity and a generous walk-in closet. A split guest bedroom and full bath provide ideal privacy and flexibility for visiting guests, a home office, or additional living space. Ideally situated in the sought-after Central Park I building, residents enjoy a coveted downtown lifestyle just moments from Southside Village, Palm Avenue’s renowned galleries, Marina Jack, Selby Gardens, and walking distance to the vibrant Sarasota Bayfront. Whether as a full-time residence or a refined seasonal retreat, this fully furnished, impeccably renovated condominium offers a rare blend of luxury, comfort, and walkable coastal living.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Dave Hall (646-256-6524)
161 S POLK DR, SARASOTA, FL 34236
$5,750,000220 Days on yellowkey MLS ID: A4672276
1 Days Off yellowkey (back on 5/11/2026)
REDUCED by $249,000 (4.2%) on 04/30/2026
Bed: 5 Bath: 5.0 Gar: 2 Liv Area Sq Ft: 4617 Built: 2013 Tax: $88,251 (2024)Community: Lido BeachSpa: YesSingle Family
Taxes:$88,251
Remarks: Under contract-accepting backup offers. In a world where more is usually never enough……. 161 S. Polk Drive is JUST ENOUGH and MORE OF EVERYTHING YOUR DREAMS ARE MADE OF! Positioned waterfront between St. Armands Circle and Lido Beach, you can start your day walking just one block to put your toes in the sand and soak up the morning sun and then head straight to your favorite lunch spot on the circle. Upon returning home, take up lounging in the split-level, salt water pool and relax to the sounds of the water as it crests the infinity edge OR you can choose one of the many decks, from rooftop on down, canal to Gulf, to savor the sun, the breeze, the views and the peacefulness all around you. Once evening arrives, hop on the boat for a pleasant ride to your waterfront dining of choice or enjoy a glass of wine as you unwind with soothing music, the gentle movement of the water and savor the setting sun. This privately gated, coastal contemporary home encompasses over 4,600 square feet of interior living space with an open plan from living to dining to kitchen and on to the outdoor patio with a full wall of pocketing sliders. The acacia wood floor will be the first to grab your eye, but you will then be drawn to the unlimited other features of this home. From the many windows offering abundant natural light, to the built-ins, wet bars, oversized kitchen island, 3 en-suite bedrooms all with private balconies (includes first and 2nd floor owner suites), elevator, outdoors showers, sauna, ‘hidden’ oversized laundry room with 2 sets of washers and dryers, oversized boat dock with 2 lifts……. Shall I go on?? The well thought out configuration of this home rationalizes JUST ENOUGH of comfortably elegant entertaining mixed with intimate peace and privacy. Recent improvements include A/C handlers and compressors, tankless water heater and pump, flat tile roof decking, refinished exterior wood railings, pool pumps and actuators, in-ground drainage system, refreshed landscaping, exterior pressure washing, recent elevator service completed
Listing Agent: Cindy Schatzle (941-587-7556)
6144 MIDNIGHT PASS RD #2N, SARASOTA, FL 34242
$1,699,000247 Days on yellowkey MLS ID: A4668144
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1204 Built: 1967 Tax: $8,388 (2025)Community: Island HouseCondo
Taxes:$8,388
Remarks: It's all about THE VIEW and the Direct Beach Access!!! This first floor condominium has a Full Gulf View from the living room and glassed-in lanai. The water views are amazing, and the sunsets are gorgeous! You will walk out your front door right down to the sand to enjoy the warm Gulf water in minutes. There was no water intrusion and no water damage to this unit in past storms, as there are enough steps up from the level of the beach sand to make it elevated! Or use the ramp for easy luggage access. The windows and doors are all wind and impact-rated, so you'll have peace of mind and a quieter home. All the floors are tile for easy care. The kitchen and bathrooms have been updated, including solid surface/granite counters and the elegant tiled showers. Furnishings and appliances have been updated in the past year. This unit is move-in ready, or you can continue to rent it with a 3-night minimum for instant income (over $58,000 income after paying rental mgmt expenses in the first 9 months of 2025). On-site management is available for all your needs. The landscaping has been refreshed, there are new tables and chairs for outdoor dining or games, and beach chairs and chase lounges are provided, as well as shade under the condo's cabanas on the beach. Shuffleboard and corn-hole games await in the center greenway. The community pool is heated for your year-round enjoyment. On the occasional rainy day, you'll enjoy the games in the club room (billiards, foosball, board games and puzzles). If you want to explore the Siesta Key Village shops, restaurants or nightlife, or explore Turtle Beach, just hop on the free trolley or other free ride-share vans. A 20-minute drive will take you to downtown Sarasota, including shops, restaurants, access to off-shore fishing or tour boats, opera, symphony, art museum, ballet, and live theater. With easy access to I-75, airport, colleges, Lifelong Learning, wine and spirits-tastings, and multiple parks and the Legacy Trail for biking, jogging, or skating, Sarasota and Siesta Key have it all! This condo is your key to the fun, so bring your toothbrush and swim suit and ENJOY IT ALL!
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Susan Keal (941-320-1689)
2613 TEMPLE ST, SARASOTA, FL 34239
$1,199,000212 Days on yellowkey MLS ID: A4673045
0 Days Off yellowkey (back on 5/10/2026)
Bed: 3 Bath: 4.0 Gar: 2 Liv Area Sq Ft: 3308 Built: 1997 Tax: $5,102 (2025)Community: Highland Park 2Spa: NoSingle Family
Taxes:$5,102
Elementary School: Alta Vista Elementary
Remarks: Under contract-accepting backup offers. PRICED TO SELL AT $1,199,000 , this is your chance to own a home with incredible value. A NEW METAL ROOF IS SCHEDULED FOR APRIL -giving buyers instant peace of mind and long-term savings from day one. A rare offering with architectural character and privacy, this property presents exceptional value for buyers seeking a truly special one-of-a-kind retreat. Welcome to Storybook — a treetop sanctuary where architecture, nature, and artistry meet! Tucked away in Arlington park at the end of a private canopied road and surrounded by native Florida landscaping and protected wetlands, this extraordinary 3-bedroom, 4-bathroom residence with a custom library/den feels like a hidden world all its own. Designed by renowned Sarasota architect Richard G. Allen, known for his sustainable and expressive style, Storybook lives up to its name — enchanting, serene, and timeless. Soaring ceilings, exposed wood beams, and maple floors create a warm, open-concept living space that flows effortlessly to the outdoors. Clerestory windows invite natural light, while the wraparound porch and treetop pool immerse you in the surrounding canopy. A spiral staircase ascends to a light filled loft offering both inspiration and a tranquil retreat above it all. This home's heart resides in a custom library/den, a quiet sanctuary where books, ideas, and conversation gather. Beyond the cozy den lies an en suite bedroom, a serene space inspired by Zen simplicity. Sliding glass doors open to the wraparound patio, a haven for morning coffee and quiet reflection. On the same floor, a second primary suite welcomes you through an intricately hand carved door. Inside, an expansive bedroom and private sitting area rests quietly among the treetops, wrapped in peaceful seclusion. The ground floor includes a private guest suite and entrance, spacious laundry room, ample storage, oversized two-car garage ,and EV charging station. From the hand-carved Tibetan gates to the tranquil pond and water feature, every detail of Storybook reflects a reverence for Sarasota’s natural beauty and a deep sense of peace and privacy. This is more than a home — it’s a place to breathe, reflect, and feel fully connected to the world around you.
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