Location: Sarasota
Keyword(s): Sarasota High
Keyword(s) High School: Sarasota High
Do Not Show Listings
6312 MIDNIGHT PASS RD #305S, SARASOTA, FL 34242
$775,000144 Days on yellowkey MLS ID: A4684866
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 894 Built: 1968 Tax: $5,871 (2025)Community: Crescent ArmsCondo
Market Analysis: For SaleFor RentSoldRented
Nearby Properties: For SaleFor RentSoldRented
Taxes:$5,871
Elementary School: Phillippi Shores Elementary
High School: Sarasota High
Tax Year: 2025
Middle School: Brookside Middle
Remarks: Positioned directly on the sands of world-famous Siesta Key, this 2-bedroom, 2-bath en-suite condominium offers the perfect blend of personal getaway and income-producing investment. Fully furnished and thoughtfully configured for vacation living, this residence is already an active vacation rental with proven historical returns, making it an ideal opportunity for buyers seeking a property that can help offset ownership costs while providing their own beachfront retreat. Inside, tile flooring throughout creates an easy-care coastal interior designed for high-traffic vacation use, while the split layout with two en-suite bedrooms provides privacy and comfort for guests. A large storage closet dedicated to beach gear and recreational “toys” makes it simple to keep everything needed for effortless days on the sand. From the residence, enjoy views of the Gulf of Mexico and the convenience of direct walk-out access to Siesta Key’s powdery white beach, where beach chairs are available for guests, perfect for owners and vacation renters alike. The location places you in one of the most desirable areas of the island, within walking distance to nearby restaurants, shops, and local favorites, or simply hop on the Siesta Key trolley for easy access up and down the island. With its prime beachfront setting, turnkey furnishings, and established rental performance, this property presents a compelling opportunity to own a slice of Siesta Key that can generate income while serving as your personal coastal escape.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-951-6660)
Listing Agent: Ryndie Brusco (941-809-6913)
4442 HOLLYBROOK WAY, SARASOTA, FL 34233
$663,00069 Days on yellowkey MLS ID: A4694025
0 Days Off yellowkey (back on 6/14/2026)
REDUCED by $22,000 (3.2%) on 06/08/2026
Bed: 4 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2310 Built: 1994Monthly Fee: $80 Tax: $4,542 (2025)Community: GreenfieldSpa: NoSingle Family
Taxes:$4,542
Elementary School: Ashton Elementary
Middle School: Sarasota Middle
Remarks: Beautifully updated and move-in ready 4-bedroom, 2-bath home in the highly desirable community of Greenfield, centrally located within top-rated school districts including Ashton Elementary School, Sarasota Middle School, and Sarasota High School. Greenfield offers low HOA fees and a peaceful setting with plenty of convenient shopping and dining amenities nearby and within short proximity to the white sand beaches of Sarasota. This meticulously maintained home is tucked along a quiet section of the neighborhood on an oversized quarter-acre lot. From the moment you arrive, you’ll appreciate the freshly painted exterior accented by timeless brick details and inviting curb appeal. Inside, the easy-living split floor plan offers 2,310 square feet under air with generous living spaces designed for both comfort and entertaining. This home is loaded with quality upgrades and recent improvements, including impact windows and sliders throughout (2025), luxury vinyl plank flooring, newer HVAC (2022), a fully updated kitchen (2022), recessed LED lighting, new ceiling fans (2026), and an impact-rated garage door (2020). The stunning gourmet kitchen features quartz countertops, stylish white shaker soft-close all-wood cabinetry with rollout drawers, stainless steel appliances, a large single-basin stainless sink, pantry storage, and both countertop seating and a dining area overlooking the pool. Just off the kitchen, the cozy living room centers around a charming wood-burning brick fireplace, creating the perfect gathering space for family and friends. The three guest bedrooms share a bathroom with convenient pool access, while the spacious primary suite offers privacy and comfort. Step outside to the generously sized screened lanai, an ideal outdoor retreat with ample shaded space for dining, relaxing, and grilling. The sparkling pool was resurfaced with a pebble finish in 2022 and features a newer Pentair pool pump, plus an outdoor shower for added convenience.The beautifully landscaped backyard is truly special, showcasing native Florida plants and flowering gardens designed for low-maintenance living. Enjoy Sunshine Mimosa ground cover, Mulberry trees, Elderberry, and a magnificent mature oak tree that provides natural shade and character. Additional exterior features include full irrigation and a new side fence installed in 2026. Every detail of this home reflects thoughtful design, exceptional upkeep, and high-quality craftsmanship, creating a stylish and worry-free property ready to be enjoyed for years to come.
Listing is courtesy of: COLDWELL BANKER REALTY (941-383-6411)
Listing Agent: Heather Gehan (941-893-0213)
2138 HAWTHORNE ST, SARASOTA, FL 34239
$2,200,00049 Days on yellowkey MLS ID: A4696176
Bed: 5 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2596 Built: 2022 Tax: $18,420 (2025)Community: La Linda TerraceSpa: NoSingle Family
Taxes:$18,420
Elementary School: Alta Vista Elementary
Remarks: Experience modern luxury at its finest in this exceptional 5-bedroom, 3.5-bath residence which redefines modern luxury through innovative design, advanced technology, and uncompromising construction. Thoughtfully designed and constructed in 2022, built of concrete and protected by impact-rated hurricane windows and doors, this home offers outstanding durability, efficiency, and peace of mind. Ideally situated in a premier location, offering convenient access to highly rated hospitals, top-performing schools, exceptional dining destinations, and a vibrant cultural arts scene. Inside, nearly 2,600 square feet of thoughtfully designed living space unfolds beneath soaring two-story ceilings and dramatic glass windows creating a breathtaking sense of openness flooding the main living spaces with natural light and picturesque views of the surrounding landscape. Clean architectural lines, minimalist linear slot vents, and carefully curated finishes create a sophisticated contemporary aesthetic. The main level features three well-appointed bedrooms, while the upper floor offers two spacious bedrooms connected by a full Jack and Jill bathroom-an ideal layout for private guests' accommodations, home offices, or flexible living space. Designed for effortless living, the fully integrated smart home system provides remote access to programable lighting, surround sound, security, climate control, motorized window treatments, and a concealed drop-down projector screen that transforms the main living area into a private theater experience. Foam-insulated walls provide enhanced sound attenuation and energy efficiency, while dual-zoned HVAC systems with UV filtration ensure personalized year-round comfort and superior indoor air quality. The chef’s kitchen showcases premium Thermador appliances, a built-in island microwave, elegant white quartz countertops, and an expansive breakfast bar ideal for entertaining and everyday living. Additional practical features include generous under-stair storage, whole-house water filtration, integrated surround sound with AirPlay connectivity, and a dedicated washer and dryer within the primary suite in addition to the main laundry area. The home is also equipped with interior and exterior power infrastructure for high-voltage EV charging, providing convenience for current and future electric vehicle owners. The luxurious primary retreat is designed as a private sanctuary, complete with a built-in white noise system and spa-inspired amenities. All three full bathroom features walk in showers, heated towel rails and under-vanity air heaters, elevating everyday comfort to a resort-like experience. Outdoor living is equally impressive. A spacious covered patio overlooks a stunning screened lap pool with panoramic screening that maximizes views while maintaining comfort and privacy. The pool area includes an outdoor shower, underwater sound system and lighting, while the fully built-in outdoor kitchen creates the perfect setting for entertaining year-round. The home is fully fenced with low-maintenance landscaping, complemented by a minimalist garden design and premium artificial turf, provides beauty without the upkeep. Combining architectural excellence, cutting-edge technology, energy-efficient construction, an unbeatable location, and exceptional indoor-outdoor living, this remarkable home offers a rare opportunity to enjoy modern luxury without compromise.
Listing Agent: Wendy Leventhal (941-376-4894)
1320 MOONMIST DR #B-11, SARASOTA, FL 34242
$1,200,000184 Days on yellowkey MLS ID: A4679270
REDUCED by $100,000 (7.7%) on 04/13/2026
Bed: 2 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 1790 Built: 1968 Tax: $5,819 (2025)Community: Polynesian GardensCondo
Taxes:$5,819
Remarks: Rarely available direct bayfront 2/2 maintenance free villa in Polynesian Gardens. Magnificent views of the Intracoastal/Little Sarasota Bay. Watch the manatees and boats go by from your paved patio directly on the water. Spacious 2 bedrooms/2 full baths with very large great room. Updated kitchen and baths with new cabinetry, granite and stainless-steel appliances. Plenty of closet space. Garage with plenty of storage plus an extra driveway allows for 2 parking spaces. Newer washer/dryer in garage. Beautiful landscaping. Community has a heated pool, clubhouse and fishing pier. Close to shops, dining and America's #1 Beach - Siesta Key. Free trolley stops directly in the front of the community on Midnight Pass Road. Two pets allowed any size.
Listing is courtesy of: COLDWELL BANKER REALTY (941-349-4411)
Listing Agent: Helene Hyland (941-685-2274)
140 S BLVD OF THE PRESIDENTS, SARASOTA, FL 34236
$2,350,000150 Days on yellowkey MLS ID: A4683280
Bed: 3 Bath: 2.0 Gar: 1 Liv Area Sq Ft: 2206 Built: 1951 Tax: $19,449 (2025)Community: Saint Armands Div John Ringling EstatesSpa: NoSingle Family
Taxes:$19,449
Elementary School: Southside Elementary
Middle School: Booker Middle
Remarks: Welcome to an extraordinary opportunity on Lido Key, where refined coastal elegance meets exceptional investment potential. This beautifully appointed three-bedroom, two-bath pool home is being offered fully turnkey furnished and has an established history as a successful income-producing rental property, making it as smart as it is stunning. Nestled beneath mature shade trees on an oversized 10,285 square foot lot, the property offers rare privacy just moments from the beach. Lush tropical landscaping surrounds the home, creating a serene island setting that feels worlds away while remaining close to everything that makes Lido Key so desirable. Inside, soaring ceilings and expansive windows flood the home with natural light, enhancing the open-concept layout designed for effortless entertaining and everyday comfort. Warm wood floors, thoughtfully curated finishes, and a soft coastal palette create a relaxed yet sophisticated ambiance throughout. Every space feels intentional, welcoming, and ready to enjoy from day one. The chef’s kitchen is a true centerpiece, featuring rich custom cabinetry, granite countertops, stainless steel appliances, double ovens, a wine fridge, and an extended breakfast bar perfect for hosting family and guests. The adjacent dining area opens seamlessly through sliding glass doors to the outdoor living space, blurring the lines between indoor comfort and Florida sunshine. The spacious primary suite serves as a private retreat, complete with vaulted ceilings and a spa-inspired bath offering dual vanities, custom cabinetry, and a walk-in shower. Two additional guest bedrooms provide flexibility for visitors or vacation renters, while a full-size laundry area, built-in workspace, and generous storage add convenience to the home’s thoughtful design. Step outside and discover your own private resort. The sparkling pool and expansive patio create the ultimate backdrop for entertaining, relaxing, and soaking in the year-round Florida lifestyle. Covered dining areas and multiple lounging spaces make this backyard oasis ideal for everything from quiet mornings with coffee to lively sunset gatherings. Location is everything, and this home delivers. Just minutes from the pristine sands of Lido Beach and the iconic boutiques and dining of St. Armands Circle, you’ll enjoy immediate access to world-class shopping, waterfront restaurants, boating, and the vibrant arts and culture of downtown Sarasota. Lido Key continues to be one of the Gulf Coast’s most coveted destinations, prized for its laid-back luxury and strong vacation rental demand. Whether you are searching for a sophisticated island residence, a luxury vacation retreat, or a high-performing investment property with proven income history, this exceptional Lido Key home offers the rare combination of lifestyle, location, and long-term value. This is more than a home — it is the island dream realized.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-758-7777)
Listing Agent: Christy Travis (941-545-5284)
3838 FLORES AVE, SARASOTA, FL 34239
$1,545,000343 Days on yellowkey MLS ID: A4661399
0 Days Off yellowkey (back on 6/13/2026)
Bed: 5 Bath: 4.5 Liv Area Sq Ft: 3033 Built: 1926 Tax: $16,879 (2025)Community: GranadaSingle Family
Taxes:$16,879
Remarks: A premier West of Trail address in Granada. A property rarely duplicated in Sarasota. Casa de Flores is a 1920s Spanish Revival compound designed for modern flexibility — multi-generational living, private guest quarters, and exceptional indoor-outdoor entertaining — all set within one of Sarasota’s most coveted neighborhoods of Granada. The main residence offers two bedrooms and two baths, anchored by a charming, well-appointed kitchen that blends character and functionality. Equipped with a 6-burner Dacor gas range, double ovens, a Sub-Zero refrigerator, and artisan tile accents, the space is intimate yet efficient — perfectly suited for everyday living or hosting close friends. Formal and informal living areas provide architectural depth, while the spacious primary suite includes a walk-in closet and a dedicated sitting area, a rare feature for a home of this era. What truly distinguishes the property are the two detached guest residences, creating a private compound atmosphere. The two-story pool house features a balcony overlooking the courtyard, with a bedroom/office and 2nd laundry access on the first level, and an additional bedroom, full kitchen, and dining area upstairs — ideal for extended family, separated living, or income potential. A separate guest casita includes a bedroom, full bath, kitchenette, and offering flexibility for in-laws, visiting guests, a private office, or creative studio. The layout allows connection when desired and privacy when needed — a rare offering West of the Trail. Original architectural details — hand-carved wood doors, arched passageways, textured plaster walls, a clawfoot tub, parquet and tile floors, and built-in bookcases — preserve the romance of Spanish Mediterranean design while thoughtful updates support modern comfort. Outdoors, the walled courtyard creates a true retreat centered around a heated pool and spa, framed by lush tropical landscaping and a trellis-covered dining area. The front patio adds another inviting gathering space, and ample parking ensures effortless hosting. Other important features are new roofs in 2021, a whole-house generator, and hurricane shutters, offering confidence for year-round or seasonal use. Minutes to Siesta Key Beach and close to Southside Village, this is a rare opportunity to own a versatile Sarasota estate property in one of the city’s most enduring and desirable neighborhoods.
Listing is courtesy of: COMPASS FLORIDA LLC (941-279-3630)
Listing Agent: Pam Charron (941-993-3388)
1010 VILLAGIO CIR #106, SARASOTA, FL 34237
$249,9001263 Days on yellowkey MLS ID: A4560093
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1058 Built: 2002Monthly Fee: $329 Tax: $2,049 (2021)Community: Villagio CondominiumCondo
Taxes:$2,049
Elementary School: Tuttle Elementary
Tax Year: 2021
Remarks: WONDERFUL. UNIQUE SARASOTA CONDO ON A VERY CONVENIENT PLACE. NEAR DOWNTOWN, BEACHES, ST. ARMANDS CIRCLE SHOPPING-RESTAURANTS AND ORIOLES BASEBALL STADIUM. AFFORDABLE PRICE.
Listing is courtesy of: WHITE SANDS REALTY GROUP FL (941-260-3350)
Listing Agent: Gloria Insua Massa (941-302-8123)
SARASOTA, FL 34242
$2,895,00044 Days on yellowkey MLS ID: A4694972
Bed: 5 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2966 Built: 2021 Tax: $24,633 (2025)Community: Point Of Rocks TerraceSpa: YesApartment
Taxes:$24,633
Remarks: There Is Only One. Crescent Beach House was purpose-built for a different kind of ownership experience. One where beach days, family gatherings, and investment performance can coexist under the same roof. Positioned in one of Siesta Key's most enduring vacation corridors, this is the type of property people return to year after year, and increasingly, seek to own. Sited at the mouth of the Point of Rocks’ beach access located at the end of the street, Crescent Beach House is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, and expansive indoor-outdoor living spaces designed to accommodate large groups with ease. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment performance. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-349-3444)
Listing Agent: Rudy Dudon (941-234-3991)
4401 LITTLE JOHN TRL, SARASOTA, FL 34232
$529,00052 Days on yellowkey MLS ID: A4695906
Bed: 3 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 1894 Built: 1986Monthly Fee: $50 Tax: $4,285 (2025)Community: Sherwood ForestSpa: YesSingle Family
Taxes:$4,285
Elementary School: Fruitville Elementary
Middle School: McIntosh Middle
Remarks: Nestled beneath majestic oak trees in the established Sherwood Forest community, this beautifully maintained home offers the perfect blend of privacy, character, and convenience. Situated on a spacious homesite, the property welcomes you with mature landscaping, abundant shade, and a tranquil setting rarely found in such a central Sarasota location. Inside, you'll find a thoughtfully designed floor plan featuring generous living spaces, abundant natural light, and comfortable accommodations for everyday living and entertaining. Brand new stainless steel appliances with a natural gas range. The home's layout flows seamlessly from the main living areas to the outdoor spaces, creating an inviting atmosphere for gatherings with family and friends. Step outside to enjoy the expansive yard, offering plenty of room for outdoor activities, gardening, or simply relaxing beneath the canopy of mature trees. Whether you're seeking a primary residence, seasonal retreat, or investment opportunity, this property provides exceptional flexibility and value. Conveniently located just minutes from I-75, shopping, dining, top-rated schools, golf courses, and Sarasota's world-famous beaches, this home combines peaceful neighborhood living with easy access to everything the Gulf Coast lifestyle has to offer. Don't miss this opportunity to own a charming Sarasota property in one of the area's most established and desirable communities. New HVAC
Listing is courtesy of: OSIPOV GROUP REAL ESTATE (941-284-4237)
Listing Agent: Bogdan Osipov (941-500-5885)
4420 OAK VIEW DR, SARASOTA, FL 34232
$790,000121 Days on yellowkey MLS ID: A4687864
0 Days Off yellowkey (back on 6/12/2026)
REDUCED by $9,900 (1.2%) on 05/29/2026
Bed: 3 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 2253 Built: 1988Monthly Fee: $172 Tax: $2,990 (2025)Community: Lakes Estates 3 Of SarasotaSingle Family
Taxes:$2,990
Elementary School: Brentwood Elementary
Remarks: Under contract-accepting backup offers. Don’t miss this rare opportunity to own a BEAUTIFULLY RENOVATED AND PROFESSIONALLY DESIGNED HOME in the highly desirable Lakes Estates community of Sarasota. Ideally situated on a quiet street, this home offers stunning curb appeal, thoughtful design, and an exceptional blend of modern upgrades and timeless character. From the moment you arrive, you’ll be impressed by the attention to detail, high-end finishes, and inviting indoor/outdoor living spaces that make this property truly special.This spacious 2,253 sq ft home features 3 BEDROOMS, 2 BATHROOMS, and a 2-CAR GARAGE (with a BONUS 4TH BEDROOM not reflected in county records). At the heart of the home is an ALL NEW HIGH-END KITCHEN featuring MARBLE COUNTERTOPS AND BACKSPLASH, NEW DESIGNER APPLIANCES, a CUSTOM RANGE HOOD, breakfast nook, soft-close cabinetry, and HIGH-END DESIGNER LIGHTING AND FIXTURES—perfect for both everyday living and entertaining. Just off the kitchen, you’ll find an OVERSIZED LAUNDRY ROOM WITH CUSTOM CABINETS and a utility sink, providing both convenience and ample storage. The home’s SPLIT FLOOR PLAN offers privacy, with the master suite located off the great room, with two bedrooms and a bath tucked away on the opposite side of the home. The ALL NEW SPA-LIKE MASTER SUITE is a true retreat, featuring a CUSTOM GLASS-ENCLOSED SHOWER, DUAL SINKS, sleek cabinetry, designer lighting and fixtures, skylight, and a LARGE WALK-IN CLOSET WITH BUILT-IN STORAGE. Enjoy direct access to the lanai through a POCKET SLIDING DOOR, as well as a unique private outdoor seating area accessible from the master bath—perfect for quiet mornings or evening relaxation. The GREAT ROOM showcases VAULTED CEILINGS WITH AN EXPOSED BEAM, creating a bright and open atmosphere. A stunning ELECTRIC FIREPLACE WITH CUSTOM STONE FACADE AND WOOD MANTLE serves as the focal point, flanked by MATCHING ARCHED BUILT-IN BOOKSHELVES with custom cabinetry and marble countertops. Seamlessly blend indoor and outdoor living with TWO SETS OF OVERSIZED POCKET SLIDING DOORS that open to the covered and fully screened lanai—ideal for entertaining or enjoying Florida’s beautiful weather year-round. The LARGE, OPEN BACKYARD offers plenty of room to design your dream pool and outdoor oasis, while the front yard features NEW SOD and mature landscaping that enhances the home’s curb appeal. Additional upgrades include NEW FLOORS, NEW LIGHTING, CUSTOM TILE, and FRESH PAINT (interior and exterior), along with a FIVE ZONE IRRIGATION SYSTEM, NEW WINDOWS (2026), NEW ROOF (2023), AC (2012), and a 2-CAR GARAGE WITH NEW EPOXY FLOOR COATING. Residents enjoy access to community amenities including a CLUBHOUSE, FITNESS CENTER, POOL, AND TENNIS COURTS. Conveniently located just a short drive to downtown Sarasota, top-rated schools, dining, shopping, and the area’s WORLD-FAMOUS GULF BEACHES, this home offers the perfect combination of comfort, style, and location. Don’t miss your chance to own this MOVE-IN READY, ONE-OF-A-KIND PROPERTY in one of Sarasota’s most convenient and sought-after areas. Schedule your private showing today!
Listing is courtesy of: INTEGRA REALTY GROUP INC (941-527-8700)
Listing Agent: Tori Krebs (360-719-0781)
6910 MIDNIGHT PASS RD #B, SARASOTA, FL 34242
$2,895,00046 Days on yellowkey MLS ID: A4694978
Bed: 5 Bath: 0.0 Gar: 2 Liv Area Sq Ft: 2801 Built: 2021 Tax: $22,665 (2025)Community: Point Of Rocks TerraceSpa: YesApartment
Taxes:$22,665
Remarks: There Is Only One. Point of Rocks. Crescent Beach. Captain Curt's. For generations, this stretch of Siesta Key has attracted families, vacationers, and investors alike, and that demand has endured year after year for what seems to be one simple reason: people never seem to stop coming back. Positioned just moments from beach access located at the end of the street, Point of Rocks is a professionally designed luxury residence and high-performing short-term vacation rental offering five bedrooms, seven baths, an elevator, resort-style pool and spa, waterslide, and expansive indoor-outdoor living spaces designed to accommodate up to fourteen guests. Unlike traditional vacation homes, the property was intentionally engineered for the demands of luxury short-term rentals, blending resort-style living with commercial-grade durability and operational efficiency. Whether enjoyed as a private family retreat, an income-producing asset, or a combination of both, the property offers a rare blend of lifestyle and investment potential. Only one adjoining residence is attached, creating a boutique ownership environment, while the neighboring property is also available for purchase separately for those seeking a larger footprint, future family compound opportunity, or multi-generational ownership strategy. Financial performance, rental history, ADR and RevPAR data available upon request.
2369 BAHIA VISTA ST, SARASOTA, FL 34239
$820,000205 Days on yellowkey MLS ID: A4676532
REDUCED by $29,000 (3.4%) on 06/11/2026
Bed: 4 Bath: 2.5 Gar: 2 Liv Area Sq Ft: 2141 Built: 2023 Tax: $7,964 (2025)Community: Avon Heights 2Spa: NoSingle Family
Taxes:$7,964
Remarks: Discover the ultimate in luxury living just a short drive from downtown Sarasota, St. Armands Circle, and Lido Beach! Designed by Arrow Homes, this inviting custom-built 2 story residence offers 4 bedrooms and 21/2 baths. Don’t miss the elegant traditional design and exceptional craftsmanship. Enjoy impressive 9’-4” ceilings, spacious owners suite, bonus loft area, custom PGT Florida Impact Rated windows and doors, oversized 2 car garage, and immaculate wood flooring and beautiful crown molding throughout the home. The open airy gourmet kitchen boasts wood cabinetry, complete with an entertainer’s island, and elegant quartz countertops highlighting the custom feel. The spacious first floor owners suite is an oasis of calm with tray ceiling, crown molding, walk in closet and a custom attached bath featuring a glass enclosed shower and freestanding soaking tub. Upstairs is the loft area along with 3 additional bedrooms and a full bath. The loft area offers desirable extra space for an office, sitting room, or kids TV area. Outside the oversized raised lanai invites you to fully enjoy the Florida way of life with plenty of room for an outdoor kitchen, hot tub, and more! The exterior of the home offers a private backyard beautifully designed landscaping, St Augustine grass, a dedicated irrigation meter and system, and a paver drive and walkway. This fantastic location is in the Southside school district with quick access to high-end shopping, dining, and entertainment opportunities. There is also room for a pool should you wish to add to the property. LOCATION, LOCATION, LOCATION! Perfectly situated to enjoy all that Sarasota has to offer. You are just minutes from the vibrant energy of Downtown Sarasota, the exclusive shopping and dining of St. Armands Circle, and the iconic shores of Lido Beach. Enjoy a short drive to world-famous Siesta Beach and the charm of Pinecraft. Exceptional proximity to top-tier medical facilities, being only half a mile to Sarasota Memorial Hospital PLUS the interstate all within 3-5 miles or just steps to public transportation. This is the exceptional lifestyle and quality home you have been waiting for!
Listing is courtesy of: PREFERRED SHORE LLC (941-999-1179)
Listing Agent: Rory Mcdonald (941-961-7247)
5855 MIDNIGHT PASS RD #420, SARASOTA, FL 34242
$745,000256 Days on yellowkey MLS ID: A4671788
REDUCED by $20,000 (2.6%) on 06/11/2026
Bed: 2 Bath: 2.0 Liv Area Sq Ft: 1152 Built: 1976 Tax: $4,975 (2024)Community: Harbor Towers Y & RCondo
Taxes:$4,975
Tax Year: 2024
Remarks: Location, location & views! Enjoy and experience luxury living at the Harbor Towers located just steps away from the world-famous Siesta Key beach. Highly desirable 4th floor unit, 2BR/2BTH with spectacular Gulf of America views from every room. Fully updated unit with new windows, new pipes, quartz countertops, new kitchen cabinets doors, new bathrooms and luxury vinyl flooring throughout. This turnkey furnished condo features an open floor plan, two suites split plan bedrooms and provides one parking space & additional storage room. New electrical panel and new water heater. Delight yourself at the HT amenities including heated resort style pools, 3 Har-Tru tennis courts, fitness center, sauna, clubhouse and a superb Marina & seating along the intercoastal waterway. HT has newly renovated building facade, common area including the lobby, spa area and hallways. A fantastic investment opportunity to own a rental income while enjoying the unit whenever you wish. Two-week minimum rentals are allowed 26 times/ year. Buyer can use the on-site property management company for rentals, or others.
Listing is courtesy of: FINE PROPERTIES (941-782-0000)
Listing Agent: Mihaela Dragan (630-330-8903)
6157 MIDNIGHT PASS RD #F22, SARASOTA, FL 34242
$529,90058 Days on yellowkey MLS ID: A4692762
Bed: 2 Bath: 2.5 Liv Area Sq Ft: 1332 Built: 1974 Tax: $5,274 (2025)Community: Bay OaksSpa: YesCondo
Taxes:$5,274
Remarks: This property is a rare find, featuring two master suites upstairs, each with its own private balcony. The home is tastefully decorated and is being sold Turnkey, making it an excellent opportunity for immediate use or investment. Notably, the property already has a strong track record of rental income with several future bookings already in place. The Bay Oaks community offers a serene setting with mature landscaping and a wide array of amenities, including a heated pool, tennis courts, recreation room and a fishing pier. It also provides the convenience of on-site management and a picnic area with Barbeques for your enjoyment. Located less than a mile from Crescent Beach, the property offers easy access to the world-renowned powdery, quartz sand of Siesta Key, recently ranked as the #4 beach in the world by Tripadvisor in 2025. The area is a premier destination spot. Additionally, the trolley stops directly in front of the complex providing easy transportation to the various dining, shopping and nightlife options Siesta Key is famous for.
Listing is courtesy of: BECKMANN REAL ESTATE (941-346-3500)
Listing Agent: Josh Beckmann (941-321-3500)
41 S ADAMS DR, SARASOTA, FL 34236
$2,050,000254 Days on yellowkey MLS ID: A4672116
Bed: 2 Bath: 2.0 Gar: 2 Liv Area Sq Ft: 3913 Built: 1951 Tax: $10,104 (2024)Community: Saint Armands Div John Ringling EstatesSingle Family
Taxes:$10,104
Remarks: Virtually Staged. Hidden behind lush plantings is this beautifully redesigned and amazingly private two-story home boasting over 3900 sq ft of interior living space all moments away from the shops & cafes of St. Armands Circle, the beaches of Lido Key & downtown Sarasota. As you enter this hideaway of peace and tranquility you are greeted by a fountained courtyard garden through gates of aged iron. From there the interiors will call to the imagination as it evokes the visions of a bastide in Provence or a country home in the hills of Scotland. Imperfection is curated and intentional. Rooms flow easily enhanced by wide plank reclaimed wood floors, white ship lap walls framed with wood accents, reclaimed wood beams artfully placed throughout, thick roughhewn interior doors with patinaed hardware, an eclectic kitchen design with soap stone counters, side tables and oven backsplash, a double farm sink, a new 10- burner dual fuel gas range with two ovens, a Sub-Zero fridge with a glass door & four bottom draws to name just a few of the many appealing details. A grand front room leads to a beautiful staircase of wood and clay tiles with a landing at the center of the house leading you to the primary suite, encompassing the entire second floor. Here we have a library/seating room lined with bookshelves, roughhewn wide plank wood floors, a spacious bedroom with a Julliet balcony, two walk-in closets and bath with a tub, large quartz shower with horizontal subway tiles, dual shower heads & handheld and two vanities with surface mount sinks and quartz counters sitting on retrofitted antique cabinets. There is a loggia spanning the width of the house opening on to an exceptionally large backyard bursting with lush tropical foliage. The nearly 12,000 sq ft lot is 160 ft deep. Intricately laid clay tiles form multiple walkways and an extensive lounging area. Beautifully weathered custom wrought iron gates abound not only on the drive entry but also on the courtyard and on the arched window openings of the loggia. Aged clay tiles surround windows and doors, even the garage door. Custom crafted metal awnings adorn the windows. Exterior custom metal lanterns and sconces echo the same intentional aging. There are two tankless water heaters, a whole house water purifier and a well for the yard. This home will captivate you.
Listing is courtesy of: MICHAEL SAUNDERS & COMPANY (941-388-4447)
Listing Agent: Jenifer Schwell (941-780-0968)
3700 S OSPREY AVE #115, SARASOTA, FL 34239
$169,000106 Days on yellowkey MLS ID: A4689629
REDUCED by $10,000 (5.6%) on 06/11/2026
Bed: 2 Bath: 1.0 Liv Area Sq Ft: 991 Built: 1979 Tax: $2,512 (2025)Community: Plaza GardensCondo
Taxes:$2,512
Remarks: West of the Trail location with convenient access to downtown Sarasota and Siesta Key. Ground floor condo featuring a newly updated kitchen with new appliances and new carpet in the bedrooms. The enclosed lanai with vinyl windows opens directly to the parking area for easy access. Unit includes in-home washer and dryer and a Jack-and-Jill bathroom layout. Assigned parking space #56 located just steps from the condominium.
Listing is courtesy of: STRINGER MANAGEMENT INC (941-922-4959)
Listing Agent: Robin De Busk (941-922-4959)
2424 WOOD ST, SARASOTA, FL 34237
$958,00077 Days on yellowkey MLS ID: TB8507065
REDUCED by $40,000 (4.0%) on 06/09/2026
Bed: 4 Bath: 3.5 Gar: 2 Liv Area Sq Ft: 2566 Built: 2015 Tax: $9,947 (2025)Community: Hudson ParkSingle Family
Taxes:$9,947
Remarks: Virtually Staged. Welcome to this beautifully designed 4-bedroom, 3.5-bathroom two-story home located in the desirable Hudson Park community in Sarasota — with no HOA fees or restrictions. Built in 2015, this thoughtfully crafted home features modern finishes and an open-concept layout, offering the perfect blend of comfort, style, and functionality. To provide additional peace of mind, thoughtful upgrades include a new HVAC system (replaced in 2026), water softener, and newer water heater (2021). Step inside to discover ceramic tile flooring throughout the entire lower-level living spaces, designed to mimic the warmth and elegance of natural wood. High ceilings and expansive windows fill the living room and dining room combination with abundant natural light, creating a bright and airy atmosphere. Sliding glass doors seamlessly connect the indoor living space to the screened-in patio - which has been pre-wired for a hot tub installation- providing a perfect location for relaxing or entertaining guests. The spacious primary suite is conveniently located on the first floor and features a luxurious ensuite bathroom complete with a modern walk-in shower, dual-sink vanity, and a custom walk-in closet with built-in organization and exceptional storage space. A conveniently located half bathroom on the lower level provides added comfort for guests. At the heart of the home is the stunning modern kitchen, showcasing warm gray wood cabinetry, beautiful granite countertops, stainless steel appliances including a built-in oven, microwave, refrigerator, dishwasher, range hood, and an electric cooktop. The oversized kitchen island offers generous seating options, while the mosaic tile backsplash and recessed lighting add stylish finishing touches. Enjoy filtered water (filtered by reverse osmosis) directly from the kitchen sink. Just off the kitchen, the laundry room includes washer and dryer hookups for everyday convenience. Upstairs, a large loft provides flexible living space ideal for a media room, office, or play area. The second level also includes three generously sized bedrooms, all featuring plush carpeting, along with two full bathrooms designed to accommodate family and guests with ease. Enjoy Florida living year-round from the screened rear porch overlooking the fenced backyard — offering privacy and plenty of room for outdoor enjoyment. Conveniently located near restaurants, Sarasota Memorial, Legacy Trail, Pompano Trailhead, Pickleball Courts and shopping, this home also places you just minutes from Marie Selby Botanical Gardens, Bayfront Park, and several area golf courses. Spend your weekends enjoying the beautiful Gulf Coast beaches with South Lido Key Beach Park and other stunning Gulf of Mexico beaches just a short drive away. This exceptional home combines modern design, spacious living, an unbeatable location, and the added benefit of no HOA, making it the perfect place to call home.
Listing is courtesy of: LPT REALTY, LLC (877-366-2213)
Listing Agent: Golf Phuphanich (813-299-3320)
336 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,195,000123 Days on yellowkey MLS ID: A4687301
REDUCED by $200,000 (3.7%) on 06/11/2026
Bed: 8 Bath: 8.5 Gar: 2 Liv Area Sq Ft: 3811 Built: 2019 Tax: $25,684 (2024)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$25,684
Remarks: Experience refined seaside luxury in this extraordinary 8-bedroom, 8.5-bathroom residence just moments from Siesta Key Beach and Siesta Key Village. Currently operating as a successful vacation rental property, this home is thoughtfully designed to maximize both guest experience and income potential. Its expansive layout, high-end finishes, and prime location make it highly desirable for short-term rentals, with ample space to comfortably host large groups. Spanning four levels and serviced by a private elevator, the home is purpose-built for hosting. The layout includes two bedrooms on the second level, five well-appointed guest suites on the third floor—many with private baths and balconies—and a top-floor bedroom offering additional privacy. Two bunk-style rooms with a shared Jack-and-Jill bath further enhance its ability to accommodate larger parties. The primary suite provides a luxurious retreat with its own balcony and spa-inspired bathroom. The open-concept main living area serves as the heart of the home, featuring a designer kitchen with premium appliances, a large gathering island, and a dedicated bar area—ideal for entertaining. Multiple dining areas, both inside and out, create flexibility for group stays, while an upper-level flex room adds value as a game room, media space, or additional lounge area. Outdoors, guests can enjoy a private resort-style setting complete with a heated pool, sun shelf, built-in spa, and covered patio designed for comfort and entertainment. Multiple balconies and a rooftop deck offer additional gathering spaces, with sweeping Gulf views and unforgettable sunsets that consistently maximize the Florida experience. With its proven rental appeal, generous accommodations, and unbeatable location, this property presents a rare opportunity to own a **turnkey, income-producing investment** or a luxurious personal getaway in one of Florida’s most sought-after beach destinations.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-954-5454)
Listing Agent: Samantha Callaway (630-865-3189)
6548 SABAL DR, SARASOTA, FL 34242
$6,195,000111 Days on yellowkey MLS ID: A4688728
REDUCED by $100,000 (1.6%) on 06/11/2026
Bed: 9 Bath: 9.5 Gar: 2 Liv Area Sq Ft: 4944 Built: 2024 Tax: $40,057 (2025)Community: Sabal PalmsSpa: YesSingle Family
Taxes:$40,057
Middle School: None
Remarks: Discover the ultimate expression of luxury coastal living in the heart of Siesta Key. This extraordinary 9-bedroom, 9.5-bath property is a true architectural showpiece, offering unmatched space, style, and sophistication just moments from world-renowned beaches and vibrant island amenities. Designed with an emphasis on grand-scale living, the home features an expansive great room floor plan that blends effortless comfort with refined elegance. The chef’s kitchen is a standout centerpiece, showcasing a large center island, premium appliances, and an oversized walk-in pantry. Perfect for both everyday living and large-scale entertaining. The dining area is enhanced by custom lighting, creating an inviting ambiance for memorable gatherings. A private elevator provides seamless access to all levels, while the 3-car garage adds convenience and storage flexibility. On the third floor of the home find an additional open family living room space with a wet bar and separate outdoor patio. No detail has been missed including an incredible game room. Every inch of this turnkey furnished home is finished with high-end materials and thoughtful craftsmanship. With nine spacious en-suite bedrooms, this property is ideal for multigenerational living, hosting guests, or maximizing income potential as a luxury rental investment. Outdoor living reaches new heights with a resort-style pool and covered spa, a super fun waterslide, and a putt-putt green are all within the interior of lush tropical landscaping. There are also plenty of outdoor dining and lounging options throughout with several patios and porches including an impressive rooftop deck which offers a panoramic view of the famous Siesta sunsets. Top rated Siesta beach is just a short stroll away as well as shops, the marina and dining. Whether you’re seeking a full-time residence, a second home, or a premier investment opportunity, this Siesta Key BEACH HOUSE delivers an unparalleled blend of luxury, versatility, and island living at its finest.
Listing is courtesy of: RE/MAX ALLIANCE GROUP (941-778-7777)
Listing Agent: Sabrina Ullmann (203-300-8181)
332 AVENIDA DE MAYO, SARASOTA, FL 34242
$5,195,000124 Days on yellowkey MLS ID: A4687188
Bed: 9 Bath: 8.0 Gar: 4 Liv Area Sq Ft: 4055 Built: 2019 Tax: $26,520 (2025)Community: Sarasota BeachSpa: YesSingle Family
Taxes:$26,520
Remarks: ~Experience elevated coastal living in this fantastic BEACH HOUSE right in the heart of SIESTA KEY VILLAGE~ This beautiful home boasts 8 bedrooms + an additional bonus room = 9, plus 8 bathrooms, including 6 en-suite retreats, perfectly suited for a large primary residence or a high-performing luxury vacation rental. Ideally located and just steps from premier dining, boutique shopping, & vibrant nightlife, and only a short stroll or bike ride to the world-renowned Siesta Key Beach. This property offers the ultimate blend of convenience with the feel of a resort-style escape. Upon entering take the stairs or the convenient elevator up to the main living space. Here you will find an open chef's kitchen, large island, a beverage bar, along with the spacious living room and dining area. There are 2 bedrooms also on this level. Multiple balconies showcase great views of the village, while the home’s prime location places you moments from everything Siesta Key has to offer. It has been thoughtfully designed with high-end designer finishes and furnishings, every detail for both comfort and entertaining. The bonus room on the 4th level leads out to a spiral staircase and then up to the rooftop deck where both village and GULF VIEWS create a great backdrop for stunning SIESTA SUNSETS. Back on the 1st level, walk out to the covered patio and enjoy your private outdoor oasis with lush landscaping and the tranquil heated pool & spa designed for both relaxation and entertainment. It features an oversized sun shelf, wraparound lounge ledge and in-water bar seating. Whether you're hosting family and friends, a large group getaway or seeking a luxury investment property, this extraordinary beach house delivers unmatched living spaces throughout. It also comes beautifully turnkey furnished and ready for immediate enjoyment or rental income. THIS IS YOUR COASTAL ESCAPE...where luxury, location, and lifestyle all meet!
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